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WO2013062114A1 - Cooking oil - Google Patents

Cooking oil Download PDF

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Publication number
WO2013062114A1
WO2013062114A1 PCT/JP2012/077802 JP2012077802W WO2013062114A1 WO 2013062114 A1 WO2013062114 A1 WO 2013062114A1 JP 2012077802 W JP2012077802 W JP 2012077802W WO 2013062114 A1 WO2013062114 A1 WO 2013062114A1
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WO
WIPO (PCT)
Prior art keywords
oil
weight
reaction
parts
palm
Prior art date
Application number
PCT/JP2012/077802
Other languages
French (fr)
Japanese (ja)
Inventor
晃生 榊
章弘 菊田
Original Assignee
株式会社カネカ
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 株式会社カネカ filed Critical 株式会社カネカ
Publication of WO2013062114A1 publication Critical patent/WO2013062114A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
    • C11B7/0075—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of melting or solidifying points
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/10—Ester interchange

Definitions

  • the present invention relates to cooking oil used for frying and the like.
  • Oxidation stability and thermal stability are listed as characteristics required for frying fats and oils, but in recent years, frying fats and oils that have a good flavor and are not odorous, making use of the flavors of the ingredients of fried foods, are desired. .
  • soybean oil and rapeseed oil are easy to use because they are highly liquid and do not generate crystals, but when used as frying oil, they have low oxidative stability, fats and oils deteriorate, and the flavor deteriorates, so it can withstand long-term use. I can't.
  • palm olein When palm olein is used for frying fats and oils, it has high oxidation stability and is less likely to deteriorate in flavor and can withstand long-term use, but crystals are generated at low temperatures and are difficult to use.
  • high oleic sunflower oil or high oleic rapeseed oil is used, the liquidity and oxidation stability are good, but there is a problem that the price is high.
  • oils for frying using cheap palm oil as raw material oils such as soybean oil, rapeseed oil, high oleic rapeseed oil, corn oil, safflower oil, sunflower oil, cottonseed oil, flaxseed oil, etc. are used at 10 ° C. ⁇ 90% by mass, 9.9 to 89.9% by mass of the oil obtained by subjecting the palm oil and fat and the liquid oil at 0 ° C.
  • triglyceride having palmitic acid bonded to ⁇ -position (2nd position) is known to exhibit much higher absorbability than triglyceride having palmitic acid bonded to ⁇ -position (1,3rd position) (patent) Reference 2).
  • the solid fat and liquid oil that are filtered out when producing a liquid oil using palm oil as a raw material have a large amount of palmitic acid as a constituent fatty acid, but most of them are bonded to the 1st and 3rd positions. It does not show high absorbency.
  • the present invention is resistant to bad taste when fried and can withstand long-term use, and crystals are not generated at low temperatures.
  • An object is to provide cooking oil that is easy to use at low cost.
  • the inventors of the present invention have palm oils and fats as a main raw material, the SU2 / UUU weight ratio is 1.9 or less, and the SSS content is 2% by weight or less.
  • a palm oil-derived liquid oil containing 10-30% by weight of glyceride to which palmitic acid is bound in the whole liquid oil expensive high oleic sunflower oil and high oleic rapeseed oil were used from inexpensive palm oil. Degradation of oil and fat during frying is suppressed, the flavor is hardly deteriorated, it can be used for a long time, and crystals are not generated during low-temperature storage, so that cooking oil that is easy to use can be obtained. As a result, the present invention has been completed.
  • glyceride containing palm oil and fat as a main raw material having a SU2 / UUU weight ratio of 1.9 or less and an SSS content of 2% by weight or less and having palmitic acid bonded in the second position is 10 to 30 in the whole liquid oil.
  • the present invention relates to a cooking oil containing 40% to 100% by weight of a palm oil-derived liquid oil containing 40% by weight of the whole cooking oil.
  • a preferred embodiment relates to the cooking oil as described above, wherein the cloud point of the palm oil-derived liquid oil is 0 to -12 ° C.
  • a preferable embodiment relates to the cooking oil described above, wherein the palm oil-derived liquid oil has a CDM value of 5 hours or more.
  • deterioration of fats and oils at the time of frying is suppressed, the flavor is hardly deteriorated, and it can be used for a long time, and since no crystal is generated at low temperature storage, a cooking oil that is easy to use can be obtained. .
  • cooked cooking oil with good absorbability can also be obtained.
  • the cooking oil according to the present invention uses glyceride in which the palm oil is the main raw material, the SU2 / UUU weight ratio is 1.9 or less, the SSS content is 2% by weight or less, and palmitic acid is bonded to the 2-position in the whole liquid oil.
  • the palm oil-derived liquid oil containing 10 to 30% by weight is preferably contained in an amount of 40 to 100% by weight in the whole cooking oil.
  • the fatty acid composition of triglyceride in the present invention is abbreviated as follows.
  • S saturated fatty acid
  • U unsaturated fatty acid
  • SSS trisaturated fatty acid glyceride
  • SU2 monosaturated fatty acid diunsaturated fatty acid glyceride
  • S2U disaturated fatty acid monounsaturated fatty acid glyceride
  • UUU triunsaturated fatty acid glyceride
  • the method for measuring each triglyceride content is as follows. ⁇ Measurement of each triglyceride content in fats and oils> Each triglyceride content in fats and oils is determined using AOCS Official using HPLC. It was measured according to Method Ce 5c-93 and calculated from the retention time and area ratio of each peak. The analysis conditions are described below. Eluent: Acetonitrile: Acetone (70:30, volume ratio) Flow rate: 0.9 ml / min Column: ODS Column temperature: 36 ° C Detector: Differential refractometer
  • the method for measuring the fatty acid composition in the fat is as follows. ⁇ Measurement of fatty acid composition in fats and oils>
  • the fatty acid composition in the fat / oil can be measured by the FID constant temperature gas chromatograph method.
  • the FID constant temperature gas chromatograph method is a method described in “2.4.2.1 Fatty acid composition” of “Standard oil analysis test method” (issue year: 1996) edited by Japan Oil Chemistry Association.
  • the palm oil-derived liquid oil used in the present invention is made of palm oil and fat, preferably palm oil and fat having an iodine value of 55 or more as a main raw material, has a specific fatty acid composition, and has low liquidity and high oxidation stability.
  • Liquid oil is not particularly limited as long as it is derived from palm oil, and examples thereof include palm refined oil, unrefined crude oil, and fractionated oil and fat such as palm olein obtained by one or more fractionations. .
  • the palm oil-derived liquid oil used in the present invention can be produced by a direct transesterification reaction of palm oil.
  • the saturated fatty acid content in the total constituent fatty acids of the palm oil used as a raw material is preferably 70% by weight or less, more preferably 3 to 70% by weight, still more preferably 3 to 52% by weight, particularly preferably 30 to 52% by weight. If the saturated fatty acid content is more than 70% by weight, there will be too many hard parts during direct transesterification, and it will be difficult to obtain crystals with good separability. It may be difficult to obtain. However, if the saturated fatty acid content is less than 3% by weight, the raw material becomes expensive, and the obtained liquid oil becomes expensive, which may increase the cost too much.
  • a preferred embodiment of palm oil is palm olein.
  • the said palm olein in this invention refers to the thing obtained by isolate
  • the content of fats and oils other than palm-based fats and oils is preferably as small as possible, preferably 50% by weight or less, more preferably 30% by weight or less, and still more preferably 10%. % By weight or less, most preferably 0% by weight. If the content of fats and oils other than palm-based fats and oils is more than 50% by weight, the raw material becomes expensive, and the obtained liquid oil becomes expensive, which may increase the cost too much.
  • the SU2 / UUU weight ratio in the finally obtained liquid oil is 1.9 or less, more preferably 1.1 or less, and the SSS content is There is no particular limitation as long as it is an edible oil and fat of 2% by weight or less.
  • Examples of such fats are soybean oil, rapeseed oil, sunflower oil, olive oil, sesame oil, canola oil, cottonseed oil, rice bran oil, safflower oil, palm oil, palm kernel oil, shea fat, monkey fat, lippe Fats, cacao butter, beef fat, pork fat, milk fat, fractionated fats and oils of these fats, hardened fats and oils, transesterified fats and the like, and the like.
  • soybean oil and rapeseed oil having a saturated fatty acid content of less than 20% by weight in the total constituent fatty acids are preferable because the effects of the present invention are easily exhibited.
  • the saturated fatty acid content in the entire constituent fatty acids of the fats and oils other than the palm-based fats and oils is preferably 70% by weight or less, more preferably 3 to 70% by weight, for the same reason as described for the palm-based fats and oils. More preferably, it is 3 to 52% by weight.
  • the SU2 / UUU weight ratio is preferably 1.9 or less, more preferably less than 1.3, and still more preferably 1.1 or less.
  • the SU2 / UUU weight ratio is preferably 1.0 or less, more preferably 0.95 or less, 0.9 or less, 0.8 or less, 0.7 or less, Hereinafter, the smaller the value, 0.5 or less, the more preferable.
  • the lower limit of the SU2 / UUU weight ratio is preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.65 or more, and 7 or more is particularly preferable.
  • the SU2 / UUU weight ratio is preferably in the range of 1.1 to 0.5, more preferably 1.0 to 0.6, and 0.95 to 0. .65 is more preferable, and 0.9 to 0.7 is most preferable.
  • the SSS content in the palm oil-derived liquid oil used in the present invention is preferably as small as possible, and the SSS content of the liquid oil is preferably 2% by weight or less, and 0.5% by weight or less. Is more preferably 0.3% by weight or less, particularly preferably 0.1% by weight or less, extremely preferably 0.05% by weight or less, and 0.03% by weight or less. Most preferred. When the SSS content of the liquid oil exceeds 2% by weight, the liquid oil may not be used as a substitute for a commonly used liquid oil.
  • the S2U content is preferably 0.5 to 10% by weight in the entire liquid oil.
  • the S2U content is more preferably 1.0 to 10.0% by weight, still more preferably 2.0 to 9.5% by weight, particularly preferably 3.0 to 9.0% by weight, and 4.0 to 8.%. 5% by weight is most preferred.
  • the UUU content is preferably 12% by weight or more, more preferably 25% by weight or more, further preferably 35% by weight or more, and 40% by weight or more. Is most preferred.
  • the palm oil-derived liquid oil used in the present invention has a high content of glyceride bound to palmitic acid at the 2-position, which is generally said to be highly absorbent, considering the absorbability of oil impregnated in food during frying. However, considering the liquidity, it is preferably 10 to 30% by weight, more preferably 13 to 30% by weight, still more preferably 16 to 30% by weight, particularly preferably 16 to 25% by weight, and 16 to 20% by weight. Most preferred.
  • the content of polyunsaturated fatty acids in the palm oil-derived liquid oil used in the present invention is preferably as low as possible from the viewpoint of oxidation stability, preferably 22% by weight or less, more preferably 21% by weight or less, and 20% by weight or less. More preferred is 19% by weight or less, particularly preferred is 18% by weight or less, and most preferred is 17% by weight or less.
  • the timing for stopping the direct transesterification described later may be advanced or the fractionation temperature may be increased.
  • the cloud point of the palm oil-derived liquid oil used in the present invention is not particularly problematic as long as the liquid oil composition is satisfied, but from the viewpoint of liquidity, 0 ° C. to ⁇ 12 ° C. is preferable, and ⁇ 2 ° C. to ⁇ 12 ° C. is more preferable, ⁇ 2.5 ° C. to ⁇ 12 ° C. is further preferable, and from the viewpoint of ease of production and oxidation stability, 0 ° C. to ⁇ 10 ° C. is preferable, and 0 ° C. to ⁇ 9 ° C. is more preferable. .
  • the palm oil-derived liquid oil used in the present invention preferably has a CDM value of 5 hours or more, more preferably 6 hours or more, and still more preferably 7 hours or more (CDM: Conductometric Determination Method, “Standard Oil Analysis Test Method”. Refer to “2.5.1.2-1996 CDM test”).
  • CDM Conductometric Determination Method, “Standard Oil Analysis Test Method”. Refer to “2.5.1.2-1996 CDM test”).
  • the palm oil-derived liquid oil used in the present invention has a high CDM value and excellent oxidation stability as described above.
  • the first production method is characterized in that the direct transesterification reaction is stopped in order to obtain a composition in which crystals with high separability are likely to be generated during crystallization.
  • the second production method is characterized in that crystals having good separability are produced during the direct transesterification reaction, and thereafter fractionation is performed without dissolving all the crystals.
  • the raw oil and fat is used, and as the SSS / S2U in the fat and oil increases, crystals with high separability are more likely to be generated and the separation efficiency increases, so that the SSS / S2U becomes 0.5 or more.
  • the direct transesterification reaction is performed until the reaction is stopped, and then the hard part is separated and removed.
  • SSS / S2U in the oil / fat is preferably as high as 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, and SSS / S2U in the oil / fat becomes 2.0 or more. It is most preferable to carry out the direct transesterification reaction.
  • the direct transesterification reaction using palm-based fats and oils having a saturated fatty acid content of 70% by weight or less in the whole constituent fatty acids as a main raw material, and at least 31% by weight of the SSS content in the oil / fat composition during the reaction. It is preferable to carry out until the S2U content is 14% by weight or less and the reaction is stopped without exceeding. If the above is satisfied, any number of direct transesterification reactions may be performed. However, considering the cost, it is preferable to stop the transesterification immediately if the above is satisfied.
  • the direct transesterification reaction is performed while flowing the fats and oils by applying force from the outside, and then the solid fat content is separated without making it 1% or less. .
  • the direct transesterification reaction is performed until the SSS / S2U in the fat becomes 0.5 or more.
  • SSS / S2U in the oil / fat is preferably as high as 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, and SSS / S2U in the oil / fat becomes 2.0 or more. It is most preferable to carry out the direct transesterification reaction.
  • the SSS content in the oil and fat composition during the direct transesterification reaction does not exceed 31% by weight, and it is even more preferable that the S2U content be 14% by weight or less.
  • crystallization is performed after the direct transesterification reaction and before the fractionation treatment.
  • the condition for raising the temperature is to prevent the solid fat content from becoming 1% by weight or less. If the temperature is raised until the solid fat content is 1% by weight or less, the heating cost increases, and the effect as a seed crystal may be lost when crystallization is performed.
  • the crystallization rate is preferably 0.01 ° C./min to 5 ° C./min, more preferably 0.1 ° C./min to 2 ° C./min. If the crystallization rate is out of the above range, the separation of the generated crystals may be poor.
  • the direct transesterification reaction in the present invention is a reaction in which transesterification is carried out while generating fat crystals under a catalyst having transesterification ability.
  • the direct transesterification method in the present invention may be either a batch type or a continuous type.
  • the direct transesterification reaction may be cyclic.
  • SSS and SS diglyceride composed of two saturated fatty acids precipitated in the palm oil and fat deposited in the raw material oil tank A adjusted to a specific temperature are precipitated, and the supernatant liquid is obtained.
  • the direct transesterification reaction is performed until the SSS / S2U in the fats and oils in the raw material oil tank A becomes 0.5 or more. More preferably, the SSS / S2U in the fat is 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, most preferably, the SSS / S2U in the fat is 2 Direct transesterification reaction is carried out until it becomes 0 or more.
  • the direct transesterification reaction is carried out until the S2U content is 14% by weight or less without the SSS content in the oil or fat exceeding 31% by weight. Thereafter, the reaction fats and oils in the raw material oil tank A are separated into liquid oil (soft part) and solid fat (hard part).
  • the catalyst used for the direct transesterification reaction is not particularly limited, and any catalyst such as a chemical catalyst or an enzyme catalyst may be used as long as it has transesterification ability.
  • a chemical catalyst potassium sodium alloy is preferable because of its high activity at low temperatures, and sodium methylate is more preferable because of economy and ease of handling.
  • the amount of the chemical catalyst used is not particularly limited, and may be an amount used in ordinary transesterification, but is preferably 0.01 to 1 part by weight with respect to 100 parts by weight of the raw oil and fat in view of reaction efficiency and economy. .
  • Sodium methylate is preferably 0.05 to 0.5 parts by weight, preferably 0.1 to 0.3 parts by weight with respect to 100 parts by weight of the raw oil and fat, from the viewpoint of reaction efficiency and fractionation efficiency, and yield of liquid oil. Part by weight is more preferred.
  • the enzyme catalyst is not particularly limited as long as it is a lipase having transesterification ability, and may be a random transesterase having no positional specificity or a transesterase having 1,3-position specificity. However, depending on the desired amount of palmitic acid at the 2-position, it is preferable to use a random transesterification reaction or a regiospecific transesterification reaction.
  • the amount of the enzyme catalyst used is not particularly limited as long as the transesterification reaction proceeds, but is preferably 0.5 to 20 parts by weight with respect to 100 parts by weight of the raw material fats and oils from the viewpoint of reaction efficiency and economy.
  • the direct transesterification reaction temperature is not particularly limited as long as it is a temperature at which the high melting point glyceride is crystallized, but a temperature at which the catalytic activity is the highest is preferable in order to perform the reaction efficiently at the start of the reaction.
  • sodium methylate it is preferably 50 ° C to 120 ° C
  • potassium sodium alloy it is preferably 25 ° C to 270 ° C.
  • an enzyme catalyst it is preferably 50 ° C to 70 ° C.
  • the direct transesterification temperature is preferably 0 ° C. to 40 ° C., more preferably 10 ° C. to 40 ° C.
  • the direct transesterification reaction temperature is preferably 0 ° C. to 40 ° C., more preferably 10 ° C. to 40 ° C. 1 to 18 hours after the start of the reaction.
  • the final reaction temperature is the direct transesterification reaction temperature.
  • stirring it is preferable to perform stirring at a speed of 1000 rpm or less, more preferably 600 rpm or less, more preferably from the viewpoint of imparting fluidity to fats and oils and producing excellent separable crystals. Preferably, it is 300 rpm to 1 rpm.
  • the final amount of crystals after the direct transesterification reaction is preferably 3% by weight to 60% by weight, more preferably 5% by weight to 40% by weight, based on the entire reaction fat and oil, from the viewpoint of fractionation efficiency.
  • the amount of crystals may be controlled by the reaction time, and the direct transesterification reaction at 0 ° C. to 40 ° C., preferably 10 ° C. to 40 ° C. is used for 1 to 48 hours when a chemical catalyst is used. In this case, it is preferable to carry out for 3 to 120 hours.
  • the method for stopping the direct transesterification reaction is not particularly limited as long as the reaction is stopped, but if it is a chemical catalyst, water or citric acid can be added, and it is acidic from the viewpoint of preventing deterioration of the equipment during fractionation. It is preferable to stop neutralization with the substance.
  • the addition amount of the terminator is preferably from 0.1 to 5 parts by weight, more preferably from 0.2 to 1 part by weight, based on 100 parts by weight of the reaction fat and oil from the viewpoint of fractionation efficiency. If the amount is more than 5 parts by weight, the filtration efficiency at the time of fractionation may deteriorate, and the yield of palm oil-derived liquid oil may decrease. On the other hand, when the addition amount of the terminator is less than 0.1 parts by weight, the color tone may deteriorate or the reaction may not stop.
  • the direct transesterification reaction was stopped from the viewpoint of the yield of palm oil-derived liquid oil until the SSS content in the fat composition during the reaction was 31 wt% or less and the S2U content was 14 wt% or less.
  • the latter is preferred. More preferably, from the viewpoint of the liquid property of the palm oil-derived liquid oil, it is preferable that the reaction is carried out until the SU2 / UUU (weight ratio) is 1.9 or less, further 1.1 or less.
  • the reaction is more preferably terminated when the SSS content is between 1% and 31% by weight, particularly preferably between 1% and 25% by weight, very particularly preferably between 1% and 20% by weight, and between 1% and 15% by weight. % Is most preferred.
  • the S2U content in the fat during the reaction decreases as the direct transesterification reaction continues, and from the viewpoint of the liquidity of the palm oil-derived liquid oil obtained by fractionation after the reaction, the S2U content in the fat during the reaction. It is preferable to stop the reaction until it is 14% by weight or less, more preferably 10% by weight or less, further preferably 7% by weight or less, and most preferably 5% by weight or less. .
  • the method for fractionating palm oil-derived liquid oil after the direct transesterification is not limited to solvent fractionation and dry fractionation. However, since solvent fractionation requires equipment costs and running costs due to the use of solvent, dry fractionation without using a solvent is preferred. . When using a solvent, hexane, acetone or the like can be used.
  • the fractionation temperature in the dry fractionation is preferably 0 ° C. to 45 ° C., preferably 30 ° C. or less, more preferably 20 ° C. or less, still more preferably 10 ° C. or less in order to obtain higher liquidity, and also the viewpoint of yield. Including 0 to 10 ° C is most preferable.
  • the cooking oil according to the present invention can be used, for example, rapeseed oil, soybean oil, palm olein, super palm olein, cottonseed oil, corn oil, safflower oil, rice, depending on various uses and materials.
  • At least one liquid oil selected from oil, sunflower oil, high oleic sunflower oil, high oleic rapeseed oil, fractionated oils thereof, and transesterified oil is blended in an amount of 60% by weight or less in the whole cooking oil.
  • the amount of the liquid oil exceeds 60% by weight and the amount of the palm oil-derived liquid oil is less than 40% by weight, the flavor deteriorates when fried and cannot be used for a long time, or at low temperatures. Sometimes crystals are generated.
  • the cooking oil of the present invention may contain an emulsifier, an antioxidant, silicone or the like as necessary.
  • the cooking oil of the present invention can be used for various fried foods such as deep-fried food, fried food, tempura, fried food, and stir-fried food, as with ordinary frying oil. Moreover, this cooking oil can be used for both non-frozen foods and frozen foods.
  • 0.05 g of the monoglyceride is dissolved in 5 ml of isooctane, 1 ml of 0.2 mol / L sodium methylate / methanol solution is added and reacted at 70 ° C. for 15 minutes to make methyl ester, and after neutralizing the reaction solution with acetic acid, an appropriate amount
  • the glyceride content having palmitic acid at the second position was determined based on the retention time and peak area area of the organic phase by gas chromatography (model number: 6890N, manufactured by Agilent).
  • liquid oils obtained by the production methods of Production Examples 1 to 10 were analyzed for fatty acid composition, triglyceride composition, cloud point, iodine value, and CDM value, and the results are summarized in Table 1.
  • the oil and fat temperature after decolorization is 1 ° C / min (set value) until 40 ° C and from 40 ° C to 0.2 ° C / min (set value), and when it reaches 10 ° C, the temperature is maintained. Then, crystallization was performed until 24 hours in total from the start of temperature drop. After crystallization, 3200 parts by weight (yield: 64%) of liquid oil was obtained by filtering using a filter press (pressurized to 3 MPa).
  • Examples 1 and 2 Comparative Examples 1 and 2 ⁇ Fly test> 1000 g of each type of fats and oils shown in Table 3 was put into an electric fryer, and while maintaining the oil temperature at 180 ° C., 50 g of frozen potato was added once every hour and fried for 5 minutes to make fries. This was performed for 8 hours a day for 4 consecutive days, and the flavor evaluation of the fries fried on the 4th day was performed in comparison with the fries fried on the 1st day. Evaluation was made by the following five-point method by eight panelists and rounded off to the second decimal place of the average score of the eight persons' evaluations to evaluate each oil and fat. 5 points: No deterioration odor similar to the flavor of French fries on the first day, and very good.
  • Table 3 shows the results of the above fly test and refrigeration test.
  • the cooking oil according to the present invention using a palm oil-derived liquid oil can be used for a long period of time, with less deterioration of oil and fat during frying, less likely to deteriorate in flavor, and at low temperatures. Preservability was also good.

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Abstract

By using a palm oil-derived liquid oil that uses a palm-type fat or oil as the main raw material therefor, has an SU2/UUU weight ratio of no more than 1.9, has an SSS content of no more than 2 wt%, and contains 10-30 wt%, relative to the total liquid oil, of a glyceride wherein palmitic acid is bonded to position 2, a cooking oil can be inexpensively obtained that, similar to expensive high oleic sunflower oil or high oleic canola oil, is easy to use due to having reduced oil deterioration during frying, being unlikely to have deterioration of flavor, being able to be used for a long period, and not crystallizing during storage. In addition, a cooking oil having good absorption can be obtained.

Description

加熱調理油Cooking oil
　本発明は、フライなどに使用される加熱調理油に関する。 The present invention relates to cooking oil used for frying and the like.
　フライ用油脂に必要な特性として酸化安定性と熱安定性が挙げられるが、特に近年は、フライ食品の素材自体の風味を活かした、油臭くなく良好な風味のフライ用油脂が望まれている。 Oxidation stability and thermal stability are listed as characteristics required for frying fats and oils, but in recent years, frying fats and oils that have a good flavor and are not odorous, making use of the flavors of the ingredients of fried foods, are desired. .
　従来、フライなどに使用される加熱調理油としては、大豆油やナタネ油、パームオレイン、ハイオレイックひまわり油、ハイオレイックナタネ油などの各種の液状油が使用されていた。しかしながら、大豆油やナタネ油は液状性が高く、結晶が発生しないため使用しやすいが、フライ油として使用すると酸化安定性が低く、油脂が劣化し、風味が悪くなるため長期間の使用に耐えられない。パームオレインをフライ用油脂に使用した場合は酸化安定性が高く、風味が悪くなりにくく、長期間の使用に耐えられるが、低温で結晶が発生し、使用しづらい。ハイオレイックひまわり油やハイオレイックナタネ油を使用すると液状性も酸化安定性も良好であるが、価格が高いという問題があった。 Conventionally, as cooking oil used for frying, various liquid oils such as soybean oil, rapeseed oil, palm olein, high oleic sunflower oil, high oleic rapeseed oil have been used. However, soybean oil and rapeseed oil are easy to use because they are highly liquid and do not generate crystals, but when used as frying oil, they have low oxidative stability, fats and oils deteriorate, and the flavor deteriorates, so it can withstand long-term use. I can't. When palm olein is used for frying fats and oils, it has high oxidation stability and is less likely to deteriorate in flavor and can withstand long-term use, but crystals are generated at low temperatures and are difficult to use. When high oleic sunflower oil or high oleic rapeseed oil is used, the liquidity and oxidation stability are good, but there is a problem that the price is high.
　安価なパーム油を原料とするフライ用油脂として、大豆油、ナタネ油、ハイオレイックナタネ油、とうもろこし油、サフラワー油、ひまわり油、綿実油、アマニ油等などの０℃で液状の油を１０～９０質量％、パーム系油脂と０℃で液状の油とを、エステル交換反応し、さらに得られたエステル交換油脂を乾式分別処理することにより得られる油を９．９～８９．９質量％、全構成脂肪酸中の炭素数２２の飽和脂肪酸含量（ベヘン酸含量）が２０～６０質量％であるナタネ極度硬化油からなる油脂を０．１～５質量％含有し、２５℃において流動性を有するフライ用油脂組成物が提案されている（特許文献１）。しかしながら、このフライ用油脂組成物においても、パームオレインと同様に、低温で結晶が発生し、使いづらい。 As oils for frying using cheap palm oil as raw material, oils such as soybean oil, rapeseed oil, high oleic rapeseed oil, corn oil, safflower oil, sunflower oil, cottonseed oil, flaxseed oil, etc. are used at 10 ° C. ~ 90% by mass, 9.9 to 89.9% by mass of the oil obtained by subjecting the palm oil and fat and the liquid oil at 0 ° C. to a transesterification reaction, and then subjecting the obtained transesterified oil to a dry fractionation treatment And 0.1 to 5% by mass of fat and oil consisting of rapeseed extremely hardened oil having a saturated fatty acid content of 22 carbon atoms (behenic acid content) of 20 to 60% by mass in all the constituent fatty acids and having fluidity at 25 ° C. An oil composition for frying has been proposed (Patent Document 1). However, in this oil composition for frying, crystals are generated at low temperatures and are difficult to use, like palm olein.
　以上のように、これまで、パーム系油脂を原料とし、フライ油として使用した場合に長期間の使用に耐えられ、低温で結晶が発生せず、使用しやすい油脂はなかった。 As described above, until now, when palm oils and fats were used as raw materials and used as frying oils, they could withstand long-term use, did not generate crystals at low temperatures, and were not easy to use.
　また、β位（２位）にパルミチン酸が結合したトリグリセライドは、α位（１，３位）にパルミチン酸が結合したトリグリセライドにくらべ、はるかに高い吸収性を示すことが知られている（特許文献２）。しかしながら、パ－ム油を原料として液状油を作製する際にろ別される固体脂及び該液状油は、構成脂肪酸としてパルミチン酸は多いものの、その殆どが１，３位に結合しており、高い吸収性を示すものではない。 In addition, triglyceride having palmitic acid bonded to β-position (2nd position) is known to exhibit much higher absorbability than triglyceride having palmitic acid bonded to α-position (1,3rd position) (patent) Reference 2). However, the solid fat and liquid oil that are filtered out when producing a liquid oil using palm oil as a raw material have a large amount of palmitic acid as a constituent fatty acid, but most of them are bonded to the 1st and 3rd positions. It does not show high absorbency.
特開２００５－１６０４５３号公報JP 2005-160453 A 特開平６－７０７８６号公報JP-A-6-70786
　本発明は、上記のような従来のフライ用油脂などの加熱調理用油脂における問題点に鑑み、フライした際に風味が悪くなりにくく長期間の使用に耐えられるとともに、低温時に結晶が発生せず使用しやすい加熱調理油を安価に提供することを目的とする。 In view of the problems in the cooking oils and fats such as the conventional frying fats and oils as described above, the present invention is resistant to bad taste when fried and can withstand long-term use, and crystals are not generated at low temperatures. An object is to provide cooking oil that is easy to use at low cost.
　本発明者らは上記課題を解決するために鋭意研究を重ねた結果、パーム系油脂を主原料とし、ＳＵ２／ＵＵＵ重量比が１．９以下且つＳＳＳ含量が２重量％以下であり、２位にパルミチン酸が結合したグリセライドを液状油全体中１０～３０重量％含有するパーム油由来液状油を使用することで、安価なパーム油から、高価なハイオレイックひまわり油やハイオレイックナタネ油を使用した場合と同等の、フライ時の油脂の劣化が抑制され、風味が悪くなりにくく、長期間使用することが出来、また低温保存時に結晶が発生しないため、使用しやすい加熱調理油を得ることが出来ることを見出し、本発明を完成させるに至った。 As a result of intensive studies to solve the above problems, the inventors of the present invention have palm oils and fats as a main raw material, the SU2 / UUU weight ratio is 1.9 or less, and the SSS content is 2% by weight or less. By using a palm oil-derived liquid oil containing 10-30% by weight of glyceride to which palmitic acid is bound in the whole liquid oil, expensive high oleic sunflower oil and high oleic rapeseed oil were used from inexpensive palm oil. Degradation of oil and fat during frying is suppressed, the flavor is hardly deteriorated, it can be used for a long time, and crystals are not generated during low-temperature storage, so that cooking oil that is easy to use can be obtained. As a result, the present invention has been completed.
　即ち、本発明は、パーム系油脂を主原料とし、ＳＵ２／ＵＵＵ重量比が１．９以下且つＳＳＳ含量が２重量％以下で２位にパルミチン酸が結合したグリセライドを液状油全体中１０～３０重量％含有するパーム油由来液状油を、加熱調理油全体中４０～１００重量％含有する加熱調理油に関する。好ましい実施態様は、前記パーム油由来液状油の曇点が０～－１２℃である上記記載の加熱調理油に関する。また、好ましい実施態様は、前記パーム油由来液状油のＣＤＭ値が５時間以上である上記記載の加熱調理油に関する。 That is, in the present invention, glyceride containing palm oil and fat as a main raw material, having a SU2 / UUU weight ratio of 1.9 or less and an SSS content of 2% by weight or less and having palmitic acid bonded in the second position is 10 to 30 in the whole liquid oil. The present invention relates to a cooking oil containing 40% to 100% by weight of a palm oil-derived liquid oil containing 40% by weight of the whole cooking oil. A preferred embodiment relates to the cooking oil as described above, wherein the cloud point of the palm oil-derived liquid oil is 0 to -12 ° C. Moreover, a preferable embodiment relates to the cooking oil described above, wherein the palm oil-derived liquid oil has a CDM value of 5 hours or more.
　本発明によれば、フライ時の油脂の劣化が抑制され、風味が悪くなりにくく長期間使用することが出来、また低温保存時に結晶が発生しないため、使用しやすい加熱調理油を得ることが出来る。また、本発明によれば、吸収性の良い加熱調理油も得ることが出来る。 According to the present invention, deterioration of fats and oils at the time of frying is suppressed, the flavor is hardly deteriorated, and it can be used for a long time, and since no crystal is generated at low temperature storage, a cooking oil that is easy to use can be obtained. . In addition, according to the present invention, cooked cooking oil with good absorbability can also be obtained.
　本発明に係る加熱調理油は、パーム系油脂を主原料とし、ＳＵ２／ＵＵＵ重量比が１．９以下且つＳＳＳ含量が２重量％以下で２位にパルミチン酸が結合したグリセライドを液状油全体中１０～３０重量％含有するパーム油由来液状油を、加熱調理油全体中４０～１００重量％含有することが好ましい。 The cooking oil according to the present invention uses glyceride in which the palm oil is the main raw material, the SU2 / UUU weight ratio is 1.9 or less, the SSS content is 2% by weight or less, and palmitic acid is bonded to the 2-position in the whole liquid oil. The palm oil-derived liquid oil containing 10 to 30% by weight is preferably contained in an amount of 40 to 100% by weight in the whole cooking oil.
　以下、本発明の加熱調理油に用いるパーム油由来液状油について説明する。 Hereinafter, the palm oil-derived liquid oil used for the cooking oil of the present invention will be described.
　本発明におけるトリグリセライドの脂肪酸組成は、以下のように略記する。
　　Ｓ：飽和脂肪酸、Ｕ：不飽和脂肪酸
　　ＳＳＳ：トリ飽和脂肪酸グリセライド
　　ＳＵ２：モノ飽和脂肪酸ジ不飽和脂肪酸グリセライド
　　Ｓ２Ｕ：ジ飽和脂肪酸モノ不飽和脂肪酸グリセライド
　　ＵＵＵ：トリ不飽和脂肪酸グリセライド The fatty acid composition of triglyceride in the present invention is abbreviated as follows.
S: saturated fatty acid, U: unsaturated fatty acid SSS: trisaturated fatty acid glyceride SU2: monosaturated fatty acid diunsaturated fatty acid glyceride S2U: disaturated fatty acid monounsaturated fatty acid glyceride UUU: triunsaturated fatty acid glyceride
　また、本発明において、前記各トリグリセライド含量を測定する方法は、以下のとおりである。
　＜油脂中の各トリグリセライド含量の測定＞
　油脂中の各トリグリセライド含量は、ＨＰＬＣを用いて、ＡＯＣＳ　Ｏｆｆｉｃｉａｌ
　Ｍｅｔｈｏｄ　Ｃｅ　５ｃ－９３に準拠して測定し、各ピークのリテンションタイムおよびエリア比から算出した。以下に、分析の条件を記す。
　　　溶離液　　：アセトニトリル：アセトン（７０：３０、体積比）
　　　流速　　　：０．９ｍｌ／分
　　　カラム　　：ＯＤＳ
　　　カラム温度：３６℃
　　　検出器　　：示差屈折計 In the present invention, the method for measuring each triglyceride content is as follows.
<Measurement of each triglyceride content in fats and oils>
Each triglyceride content in fats and oils is determined using AOCS Official using HPLC.
It was measured according to Method Ce 5c-93 and calculated from the retention time and area ratio of each peak. The analysis conditions are described below.
Eluent: Acetonitrile: Acetone (70:30, volume ratio)
Flow rate: 0.9 ml / min Column: ODS
Column temperature: 36 ° C
Detector: Differential refractometer
　更に、本発明において、油脂中の脂肪酸組成を測定する方法は、以下のとおりである。
＜油脂中の脂肪酸組成の測定＞
　油脂中の脂肪酸組成の測定は、ＦＩＤ恒温ガスクロマトグラフ法により行うことができる。ＦＩＤ恒温ガスクロマトグラフ法とは、社団法人日本油化学協会編「基準油脂分析試験法」（発行年：１９９６年）の「２．４．２．１　脂肪酸組成」に記載された方法である。 Furthermore, in the present invention, the method for measuring the fatty acid composition in the fat is as follows.
<Measurement of fatty acid composition in fats and oils>
The fatty acid composition in the fat / oil can be measured by the FID constant temperature gas chromatograph method. The FID constant temperature gas chromatograph method is a method described in “2.4.2.1 Fatty acid composition” of “Standard oil analysis test method” (issue year: 1996) edited by Japan Oil Chemistry Association.
　本発明で用いるパーム油由来液状油は、パーム系油脂、好ましくはヨウ素価５５以上のパーム系油脂を主原料とし、特定の脂肪酸組成を有し、高い液状性と酸化安定性を兼ね備えた安価な液状油である。前記パーム系油脂としては、パーム油由来であれば特に限定はなく、パーム精製油、未精製のクルード油、一回以上の分別によって得られたパームオレインなどの分画油脂、などが例示される。 The palm oil-derived liquid oil used in the present invention is made of palm oil and fat, preferably palm oil and fat having an iodine value of 55 or more as a main raw material, has a specific fatty acid composition, and has low liquidity and high oxidation stability. Liquid oil. The palm oil and fat is not particularly limited as long as it is derived from palm oil, and examples thereof include palm refined oil, unrefined crude oil, and fractionated oil and fat such as palm olein obtained by one or more fractionations. .
　本発明で用いるパーム油由来液状油は、パーム系油脂のダイレクトエステル交換反応により製造することができる。 The palm oil-derived liquid oil used in the present invention can be produced by a direct transesterification reaction of palm oil.
　原料として使用するパーム系油脂の構成脂肪酸全体中の飽和脂肪酸含量は７０重量％以下であることが好ましく、より好ましくは３～７０重量％、更に好ましくは３～５２重量％、特に好ましくは３０～５２重量％である。飽和脂肪酸含量が７０重量％より多いと、ダイレクトエステル交換中に硬質部が多くなり過ぎ、分離性の良い結晶を得ることが困難になり、液状性の高いパーム油由来液状油を高収率で得ることが困難な場合がある。しかし、飽和脂肪酸含量が３重量％より少ないと、原料が高価になり、得られた液状油も高価なものになるため、コストが上がりすぎる場合がある。パーム系油脂の好ましい実施態様はパームオレインである。本発明における前記パームオレインとは、パームの果肉から採取した油脂を分離して得られ、ヨウ素価が５５以上のものを指す。 The saturated fatty acid content in the total constituent fatty acids of the palm oil used as a raw material is preferably 70% by weight or less, more preferably 3 to 70% by weight, still more preferably 3 to 52% by weight, particularly preferably 30 to 52% by weight. If the saturated fatty acid content is more than 70% by weight, there will be too many hard parts during direct transesterification, and it will be difficult to obtain crystals with good separability. It may be difficult to obtain. However, if the saturated fatty acid content is less than 3% by weight, the raw material becomes expensive, and the obtained liquid oil becomes expensive, which may increase the cost too much. A preferred embodiment of palm oil is palm olein. The said palm olein in this invention refers to the thing obtained by isolate | separating the fats and oils extract | collected from the pulp of palm, and an iodine number is 55 or more.
　本発明で用いるパーム油由来液状油を製造する際には、原料油脂として、パーム系油脂に加えて、パーム系油脂以外の油脂を更に用いても良い。但し、本発明の効果をより享受するためにはパーム系油脂以外の油脂の含有量は少ない程良く、原料油脂全体中５０重量％以下が好ましく、より好ましくは３０重量％以下、更に好ましくは１０重量％以下、最も好ましくは０重量％である。パーム系油脂以外の油脂の含有量が５０重量％より多いと、原料が高価になり、得られた液状油も高価なものになるため、コストが上がりすぎる場合がある。 When manufacturing the palm oil origin liquid oil used by this invention, in addition to palm type fats and oils, you may further use fats and oils other than palm type fats and oils as raw material fats and oils. However, in order to further enjoy the effects of the present invention, the content of fats and oils other than palm-based fats and oils is preferably as small as possible, preferably 50% by weight or less, more preferably 30% by weight or less, and still more preferably 10%. % By weight or less, most preferably 0% by weight. If the content of fats and oils other than palm-based fats and oils is more than 50% by weight, the raw material becomes expensive, and the obtained liquid oil becomes expensive, which may increase the cost too much.
　パーム油由来液状油の製造に用いるパーム系油脂以外の油脂としては、最終的に得られる液状油中のＳＵ２／ＵＵＵ重量比が１．９以下、より好ましくは１．１以下、且つＳＳＳ含量が２重量％以下となる食用油脂であれば特に限定はない。そのような油脂の例としては、大豆油、ナタネ油、ひまわり油、オリーブ油、ごま油、キャノーラ油、綿実油、こめ油、サフラワー油、やし油、パーム核油、シア脂、サル脂、イリッぺ脂、カカオ脂、牛脂、豚脂、乳脂、これらの油脂の分別油脂、硬化油脂、エステル交換油脂などが挙げられる。これらの中でも、構成脂肪酸全体中の飽和脂肪酸含量が２０重量％よりも低い大豆油、ナタネ油などが本発明の効果を発現し易いために好ましい。 As fats and oils other than palm-based fats and oils used for the production of palm oil-derived liquid oil, the SU2 / UUU weight ratio in the finally obtained liquid oil is 1.9 or less, more preferably 1.1 or less, and the SSS content is There is no particular limitation as long as it is an edible oil and fat of 2% by weight or less. Examples of such fats are soybean oil, rapeseed oil, sunflower oil, olive oil, sesame oil, canola oil, cottonseed oil, rice bran oil, safflower oil, palm oil, palm kernel oil, shea fat, monkey fat, lippe Fats, cacao butter, beef fat, pork fat, milk fat, fractionated fats and oils of these fats, hardened fats and oils, transesterified fats and the like, and the like. Among these, soybean oil and rapeseed oil having a saturated fatty acid content of less than 20% by weight in the total constituent fatty acids are preferable because the effects of the present invention are easily exhibited.
　前記パーム系油脂以外の油脂の構成脂肪酸全体中の飽和脂肪酸含量は、パーム系油脂について述べたのと同様の理由により、７０重量％以下であることが好ましく、より好ましくは３～７０重量％、更に好ましくは３～５２重量％である。 The saturated fatty acid content in the entire constituent fatty acids of the fats and oils other than the palm-based fats and oils is preferably 70% by weight or less, more preferably 3 to 70% by weight, for the same reason as described for the palm-based fats and oils. More preferably, it is 3 to 52% by weight.
　本発明で用いるパーム油由来液状油のトリグリセライド組成は、ＳＵ２／ＵＵＵ重量比が１．９以下が好ましく、１．３未満がより好ましく、更に好ましくは１．１以下である。前記ＳＵ２／ＵＵＵ重量比は、更に高い液状性を求めると、１．０以下がより好ましく、０．９５以下が更に好ましく、０．９以下、０．８以下、０．７以下、０．６以下、０．５以下と、小さくなるほど好ましい。一方、製造のし易さと酸化安定性を考慮すると、前記ＳＵ２／ＵＵＵ重量比の下限値は、０．５以上が好ましく、０．６以上がより好ましく、０．６５以上が更に好ましく、０．７以上が特に好ましい。液状性と製造のし易さのバランスを考慮すると、前記ＳＵ２／ＵＵＵ重量比は、１．１～０．５の範囲が好ましく、１．０～０．６がより好ましく、０．９５～０．６５が更に好ましく、０．９～０．７が最も好ましい。 In the triglyceride composition of the palm oil-derived liquid oil used in the present invention, the SU2 / UUU weight ratio is preferably 1.9 or less, more preferably less than 1.3, and still more preferably 1.1 or less. The SU2 / UUU weight ratio is preferably 1.0 or less, more preferably 0.95 or less, 0.9 or less, 0.8 or less, 0.7 or less, Hereinafter, the smaller the value, 0.5 or less, the more preferable. On the other hand, in view of ease of production and oxidation stability, the lower limit of the SU2 / UUU weight ratio is preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.65 or more, and 7 or more is particularly preferable. In consideration of the balance between liquidity and ease of production, the SU2 / UUU weight ratio is preferably in the range of 1.1 to 0.5, more preferably 1.0 to 0.6, and 0.95 to 0. .65 is more preferable, and 0.9 to 0.7 is most preferable.
　また、本発明で用いるパーム油由来液状油中におけるＳＳＳ含量をできるだけ少なくすることが好ましく、該液状油のＳＳＳ含量は、２重量％以下であることが好ましく、０．５重量％以下であることがより好ましく、０．３重量％以下であることが更に好ましく、０．１重量％以下であることが特に好ましく、０．０５重量％以下であることが極めて好ましく、０．０３重量％以下が最も好ましい。該液状油のＳＳＳ含量が２重量％を超えると、通常用いられている液油の代替として使用できない場合がある。 The SSS content in the palm oil-derived liquid oil used in the present invention is preferably as small as possible, and the SSS content of the liquid oil is preferably 2% by weight or less, and 0.5% by weight or less. Is more preferably 0.3% by weight or less, particularly preferably 0.1% by weight or less, extremely preferably 0.05% by weight or less, and 0.03% by weight or less. Most preferred. When the SSS content of the liquid oil exceeds 2% by weight, the liquid oil may not be used as a substitute for a commonly used liquid oil.
　更に、本発明で用いるパーム油由来液状油の液状性を維持するためには、Ｓ２Ｕ含量が液状油全体中０．５～１０重量％であることが好ましい。Ｓ２Ｕ含有量は、１．０～１０．０重量％がより好ましく、２．０～９．５重量％が更に好ましく、３．０～９．０重量％が特に好ましく、４．０～８．５重量％が最も好ましい。また、上記と同様の理由でＵＵＵ含量は１２重量％以上であることが好ましく、２５重量％以上であることがより好ましく、３５重量％以上であることが更に好ましく、４０重量％以上であることが最も好ましい。 Furthermore, in order to maintain the liquidity of the palm oil-derived liquid oil used in the present invention, the S2U content is preferably 0.5 to 10% by weight in the entire liquid oil. The S2U content is more preferably 1.0 to 10.0% by weight, still more preferably 2.0 to 9.5% by weight, particularly preferably 3.0 to 9.0% by weight, and 4.0 to 8.%. 5% by weight is most preferred. For the same reason as above, the UUU content is preferably 12% by weight or more, more preferably 25% by weight or more, further preferably 35% by weight or more, and 40% by weight or more. Is most preferred.
　本発明で用いるパーム油由来液状油は、フライ時に食品中に含浸した油分の吸収性を考慮すると、一般的に吸収性が高いといわれている２位にパルミチン酸が結合したグリセライドの含量が多いほど好ましいが、液状性も考慮すると１０～３０重量％が好ましく、１３～３０重量％がより好ましく、１６～３０重量％が更に好ましく、１６～２５重量％が特に好ましく、１６～２０重量％が最も好ましい。 The palm oil-derived liquid oil used in the present invention has a high content of glyceride bound to palmitic acid at the 2-position, which is generally said to be highly absorbent, considering the absorbability of oil impregnated in food during frying. However, considering the liquidity, it is preferably 10 to 30% by weight, more preferably 13 to 30% by weight, still more preferably 16 to 30% by weight, particularly preferably 16 to 25% by weight, and 16 to 20% by weight. Most preferred.
　本発明で用いるパーム油由来液状油中の多価不飽和脂肪酸含量は、酸化安定性の観点からは少ないほど良く、２２重量％以下が好ましく、２１重量％以下がより好ましく、２０重量％以下が更に好ましく、１９重量％以下が特に好ましく、１８重量％以下が極めて好ましく、１７重量％以下が最も好ましい。多価不飽和脂肪酸量を減らすには、後述のダイレクトエステル交換反応を停止するタイミングを早めるか、分別温度を高くすればよい。 The content of polyunsaturated fatty acids in the palm oil-derived liquid oil used in the present invention is preferably as low as possible from the viewpoint of oxidation stability, preferably 22% by weight or less, more preferably 21% by weight or less, and 20% by weight or less. More preferred is 19% by weight or less, particularly preferred is 18% by weight or less, and most preferred is 17% by weight or less. In order to reduce the amount of polyunsaturated fatty acids, the timing for stopping the direct transesterification described later may be advanced or the fractionation temperature may be increased.
　また、本発明で用いるパーム油由来液状油の曇点は、前記液状油組成を満たしていれば特に問題はないが、液状性の観点からは０℃～－１２℃が好ましく、－２℃～－１２℃がより好ましく、－２．５℃～－１２℃が更に好ましく、製造のし易さと酸化安定性の観点からは０℃～－１０℃が好ましく、０℃～－９℃がより好ましい。 Further, the cloud point of the palm oil-derived liquid oil used in the present invention is not particularly problematic as long as the liquid oil composition is satisfied, but from the viewpoint of liquidity, 0 ° C. to −12 ° C. is preferable, and −2 ° C. to −12 ° C. is more preferable, −2.5 ° C. to −12 ° C. is further preferable, and from the viewpoint of ease of production and oxidation stability, 0 ° C. to −10 ° C. is preferable, and 0 ° C. to −9 ° C. is more preferable. .
　また、本発明で用いるパーム油由来液状油は、ＣＤＭ値が５時間以上が好ましく、より好ましくは６時間以上、更に好ましくは７時間以上である（ＣＤＭ：Conductometric Determination Method、「基準油脂分析試験法 2.5.1.2-1996 ＣＤＭ試験」参照。）。本発明で用いるパーム油由来液状油は、前記のようにＣＤＭ値が高く、酸化安定性に優れる。 The palm oil-derived liquid oil used in the present invention preferably has a CDM value of 5 hours or more, more preferably 6 hours or more, and still more preferably 7 hours or more (CDM: Conductometric Determination Method, “Standard Oil Analysis Test Method”. Refer to “2.5.1.2-1996 CDM test”). The palm oil-derived liquid oil used in the present invention has a high CDM value and excellent oxidation stability as described above.
　本発明で用いるパーム油由来液状油の製造方法としては２つある。第一の製造方法は、晶析時に分離性の高い結晶が発生しやすい組成にするためにダイレクトエステル交換反応をどこで停止させるかに特徴がある。また、第二の製造方法は、ダイレクトエステル交換反応中に分離性の良い結晶を生成させ、その後、その結晶を全て溶解させず分別を行なうことに特徴がある。 There are two methods for producing the palm oil-derived liquid oil used in the present invention. The first production method is characterized in that the direct transesterification reaction is stopped in order to obtain a composition in which crystals with high separability are likely to be generated during crystallization. In addition, the second production method is characterized in that crystals having good separability are produced during the direct transesterification reaction, and thereafter fractionation is performed without dissolving all the crystals.
　第一の製造方法では、前記原料油脂を用い、油脂中のＳＳＳ／Ｓ２Ｕが大きくなるほど分離性の高い結晶が発生しやすくなり、分離効率が上がることから、ＳＳＳ／Ｓ２Ｕが０．５以上になるまでダイレクトエステル交換反応を行い、反応を停止させた後、硬質部を分別除去する。前記油脂中のＳＳＳ／Ｓ２Ｕが０．７５以上、１．０以上、１．２５以上、１．５以上、１．７５以上と大きくなるほど好ましく、油脂中のＳＳＳ／Ｓ２Ｕが２．０以上になるまでダイレクトエステル交換反応を行うことが最も好ましい。好ましい実施態様では、構成脂肪酸全体中の飽和脂肪酸含量が７０重量％以下であるパーム系油脂を主原料としたダイレクトエステル交換反応を、少なくとも反応中の油脂組成物中のＳＳＳ含量が３１重量％を超えることなく、Ｓ２Ｕ含量が１４重量％以下になり、反応を停止させるまで行うことが好ましく、その後、分別する。前記を満たせば、ダイレクトエステル交換反応はどれだけ行っても良いが、コストを考え、前記を満たせば直ぐに停止させることが好ましい。 In the first production method, the raw oil and fat is used, and as the SSS / S2U in the fat and oil increases, crystals with high separability are more likely to be generated and the separation efficiency increases, so that the SSS / S2U becomes 0.5 or more. The direct transesterification reaction is performed until the reaction is stopped, and then the hard part is separated and removed. SSS / S2U in the oil / fat is preferably as high as 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, and SSS / S2U in the oil / fat becomes 2.0 or more. It is most preferable to carry out the direct transesterification reaction. In a preferred embodiment, the direct transesterification reaction using palm-based fats and oils having a saturated fatty acid content of 70% by weight or less in the whole constituent fatty acids as a main raw material, and at least 31% by weight of the SSS content in the oil / fat composition during the reaction. It is preferable to carry out until the S2U content is 14% by weight or less and the reaction is stopped without exceeding. If the above is satisfied, any number of direct transesterification reactions may be performed. However, considering the cost, it is preferable to stop the transesterification immediately if the above is satisfied.
　また、第二の製造方法では、前記した原料油脂を用い、外部から力を加えることで油脂を流動させながらダイレクトエステル交換反応を行い、その後、固体脂含量を１％以下にすることなく分別する。好ましい実施態様では、油脂中のＳＳＳ／Ｓ２Ｕが０．５以上になるまでダイレクトエステル交換反応を行う。前記油脂中のＳＳＳ／Ｓ２Ｕが０．７５以上、１．０以上、１．２５以上、１．５以上、１．７５以上と大きくなるほど好ましく、油脂中のＳＳＳ／Ｓ２Ｕが２．０以上になるまでダイレクトエステル交換反応を行うことが最も好ましい。また、ダイレクトエステル交換反応中の油脂組成中のＳＳＳ含量が３１重量％を超えないことがより好ましく、且つ、Ｓ２Ｕ含量が１４重量％以下になることが更に好ましい。 In the second production method, the above-described raw material fats and oils are used, a direct transesterification reaction is performed while flowing the fats and oils by applying force from the outside, and then the solid fat content is separated without making it 1% or less. . In a preferred embodiment, the direct transesterification reaction is performed until the SSS / S2U in the fat becomes 0.5 or more. SSS / S2U in the oil / fat is preferably as high as 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, and SSS / S2U in the oil / fat becomes 2.0 or more. It is most preferable to carry out the direct transesterification reaction. Moreover, it is more preferable that the SSS content in the oil and fat composition during the direct transesterification reaction does not exceed 31% by weight, and it is even more preferable that the S2U content be 14% by weight or less.
　外部から力を加えて油脂を流動させるためには、攪拌する、反応管などにポンプなどの外圧で油脂を通す、高所から自然落下させるなど、各種の方法を採用しうる。具体的には、撹拌するには、攪拌翼を有しているタンクやピンマシンなどの装置を用いることにより、反応させる油脂を流動させる。反応管などにポンプなどの外圧で油脂を通すには、スタティックミキサーなどの手段により、反応させる油脂を流動させることができる。もし、反応開始時や途中で撹拌などによる外部からの力を加えず、油脂を流動させないでダイレクトエステル交換反応を行うと、分離性の悪い結晶が生成し、反応中の油脂が固形状になってしまい、分別が困難となる場合がある。 In order to apply the force from the outside to flow the oil and fat, various methods such as stirring, passing the oil and fat through a reaction tube or the like with an external pressure such as a pump, or letting it fall naturally from a high place can be adopted. Specifically, in order to stir, the oils and fats to be reacted are fluidized by using an apparatus such as a tank or a pin machine having a stirring blade. In order to pass fats and oils through a reaction tube or the like with an external pressure such as a pump, the fats and oils to be reacted can be flowed by means such as a static mixer. If direct transesterification is performed without applying external force such as stirring at the start of the reaction or in the middle of the reaction without causing the oil or oil to flow, crystals with poor separability will be produced, and the oil or fat during the reaction will be solid. And separation may be difficult.
　前記外部から力を加えて油脂を流動させてダイレクトエステル交換反応を行う第二の製造方法において、更に液状性を高めるためには、ダイレクトエステル交換反応後、分別処理するまでに、晶析することが好ましく、収率を高めるためには昇温することが好ましい。但し、晶析せずに昇温のみする場合は液状性が低くなる場合がある。昇温する場合の条件は、固体脂含量が１重量％以下にならないようにすることである。もし、固体脂含量が１重量％以下になるまで昇温すると、加熱のためのコストが高くなり、また晶析も行う場合に種晶としての効果がなくなる場合がある。晶析速度は０．０１℃／分～５℃／分が好ましく、０．１℃／分～２℃／分がより好ましい。晶析速度が前記範囲を外れると、生成する結晶の分離性が悪い場合がある。 In the second production method in which a direct transesterification reaction is performed by applying a force from the outside to cause the oil to flow, in order to further improve the liquidity, crystallization is performed after the direct transesterification reaction and before the fractionation treatment. In order to increase the yield, it is preferable to raise the temperature. However, when only raising the temperature without crystallization, the liquidity may be lowered. The condition for raising the temperature is to prevent the solid fat content from becoming 1% by weight or less. If the temperature is raised until the solid fat content is 1% by weight or less, the heating cost increases, and the effect as a seed crystal may be lost when crystallization is performed. The crystallization rate is preferably 0.01 ° C./min to 5 ° C./min, more preferably 0.1 ° C./min to 2 ° C./min. If the crystallization rate is out of the above range, the separation of the generated crystals may be poor.
　本発明における上記ダイレクトエステル交換反応とは、エステル交換能を有する触媒下で油脂結晶を発生させながらエステル交換を行う反応である。本発明におけるダイレクトエステル交換反応の方法は、バッチ式、連続式を問わない。更に、前記ダイレクトエステル交換反応は、循環式であってもよい。循環式のダイレクトエステル交換反応としては、例えば、特定の温度に調整した原料油タンクＡで析出したパーム系油脂中のＳＳＳ及びＳＳ（飽和脂肪酸２つで構成されるジグリセライド）を沈降させ、上澄み液をエステル交換装置Ｂに連続的に移送する工程（１）と、エステル交換装置Ｂにおいて、移送された上澄み液をリパーゼの至適温度でエステル交換反応し、その後、再び原料油タンクＡに移送する工程（２）を繰り返すことで、原料油タンクＡにある油脂中のＳＳＳ／Ｓ２Ｕが０．５以上になるまでダイレクトエステル交換反応を行う。より好ましくは、前記油脂中のＳＳＳ／Ｓ２Ｕが、０．７５以上、１．０以上、１．２５以上、１．５以上、１．７５以上、最も好ましくは前記油脂中のＳＳＳ／Ｓ２Ｕが２．０以上になるまでダイレクトエステル交換反応を行う。更に好ましくは、油脂中のＳＳＳ含量が３１重量％を超えることなく、Ｓ２Ｕ含量が１４重量％以下になるまでダイレクトエステル交換反応を行う。その後、原料油タンクＡ中の反応油脂を液状油（軟質部）と固体脂（硬質部）とに分別する。 The direct transesterification reaction in the present invention is a reaction in which transesterification is carried out while generating fat crystals under a catalyst having transesterification ability. The direct transesterification method in the present invention may be either a batch type or a continuous type. Furthermore, the direct transesterification reaction may be cyclic. As the cyclic direct transesterification reaction, for example, SSS and SS (diglyceride composed of two saturated fatty acids) precipitated in the palm oil and fat deposited in the raw material oil tank A adjusted to a specific temperature are precipitated, and the supernatant liquid is obtained. Is continuously transferred to the transesterification apparatus B (1), and in the transesterification apparatus B, the transferred supernatant is transesterified at the optimum temperature of the lipase and then transferred again to the feed oil tank A. By repeating the step (2), the direct transesterification reaction is performed until the SSS / S2U in the fats and oils in the raw material oil tank A becomes 0.5 or more. More preferably, the SSS / S2U in the fat is 0.75 or more, 1.0 or more, 1.25 or more, 1.5 or more, 1.75 or more, most preferably, the SSS / S2U in the fat is 2 Direct transesterification reaction is carried out until it becomes 0 or more. More preferably, the direct transesterification reaction is carried out until the S2U content is 14% by weight or less without the SSS content in the oil or fat exceeding 31% by weight. Thereafter, the reaction fats and oils in the raw material oil tank A are separated into liquid oil (soft part) and solid fat (hard part).
　前記ダイレクトエステル交換反応に使用する触媒は特に限定せず、エステル交換能を有していれば化学触媒、酵素触媒など何を使用しても良い。化学触媒の中でもカリウムナトリウム合金は低温での活性が高いことから好ましく、ナトリウムメチラートは経済性や扱い易さからより好ましい。化学触媒の使用量は特に限定されず、通常のエステル交換で使用される量で良いが、反応効率と経済性からは原料油脂１００重量部に対して０．０１重量部～１重量部が好ましい。ナトリウムメチラートでは、反応効率と分別効率、液状油の収率の観点から原料油脂１００重量部に対して０．０５重量部～０．５重量部が好ましく、０．１重量部～０．３重量部がより好ましい。 The catalyst used for the direct transesterification reaction is not particularly limited, and any catalyst such as a chemical catalyst or an enzyme catalyst may be used as long as it has transesterification ability. Among the chemical catalysts, potassium sodium alloy is preferable because of its high activity at low temperatures, and sodium methylate is more preferable because of economy and ease of handling. The amount of the chemical catalyst used is not particularly limited, and may be an amount used in ordinary transesterification, but is preferably 0.01 to 1 part by weight with respect to 100 parts by weight of the raw oil and fat in view of reaction efficiency and economy. . Sodium methylate is preferably 0.05 to 0.5 parts by weight, preferably 0.1 to 0.3 parts by weight with respect to 100 parts by weight of the raw oil and fat, from the viewpoint of reaction efficiency and fractionation efficiency, and yield of liquid oil. Part by weight is more preferred.
　酵素触媒は、エステル交換能を有するリパーゼであれば特に限定されず、位置特異性が全くないランダムエステル交換酵素でも、１，３位特異性を有するエステル交換酵素でも良い。但し、所望の２位のパルミチン酸量によっては、ランダムエステル交換反応を行うか、位置特異的エステル交換反応を行うかは、使い分けた方が好ましい。酵素触媒の使用量はエステル交換反応が進行する量であれば良く特に限定されないが、反応効率と経済性から原料油脂１００重量部に対して０．５重量部～２０重量部が好ましい。 The enzyme catalyst is not particularly limited as long as it is a lipase having transesterification ability, and may be a random transesterase having no positional specificity or a transesterase having 1,3-position specificity. However, depending on the desired amount of palmitic acid at the 2-position, it is preferable to use a random transesterification reaction or a regiospecific transesterification reaction. The amount of the enzyme catalyst used is not particularly limited as long as the transesterification reaction proceeds, but is preferably 0.5 to 20 parts by weight with respect to 100 parts by weight of the raw material fats and oils from the viewpoint of reaction efficiency and economy.
　本発明において、ダイレクトエステル交換反応温度は、高融点グリセライドが結晶化する温度であれば特に限定されないが、反応開始時は効率良く反応を行なうために触媒活性が最も高くなる温度が好ましい。具体的には、ナトリウムメチラートを使用する場合は５０℃～１２０℃が好ましく、カリウムナトリウム合金を使用する場合は２５℃～２７０℃が好ましい。また、酵素触媒を使用する場合は５０℃～７０℃が好ましい。また、化学触媒を使用する場合は、反応開始から５～２０分後に、ダイレクトエステル交換反応温度を０℃～４０℃にすることが好ましく、１０℃～４０℃にすることがより好ましい。酵素触媒を使用する場合は、反応開始から１～１８時間後に、ダイレクトエステル交換反応温度を０℃～４０℃にすることが好ましく、１０℃～４０℃にすることがより好ましい。なお、本発明では、最終的な反応温度をダイレクトエステル交換反応温度とする。 In the present invention, the direct transesterification reaction temperature is not particularly limited as long as it is a temperature at which the high melting point glyceride is crystallized, but a temperature at which the catalytic activity is the highest is preferable in order to perform the reaction efficiently at the start of the reaction. Specifically, when sodium methylate is used, it is preferably 50 ° C to 120 ° C, and when potassium sodium alloy is used, it is preferably 25 ° C to 270 ° C. When an enzyme catalyst is used, it is preferably 50 ° C to 70 ° C. When a chemical catalyst is used, the direct transesterification temperature is preferably 0 ° C. to 40 ° C., more preferably 10 ° C. to 40 ° C. 5 to 20 minutes after the start of the reaction. When an enzyme catalyst is used, the direct transesterification reaction temperature is preferably 0 ° C. to 40 ° C., more preferably 10 ° C. to 40 ° C. 1 to 18 hours after the start of the reaction. In the present invention, the final reaction temperature is the direct transesterification reaction temperature.
　上記ダイレクトエステル交換反応において、攪拌する場合は、油脂に流動性を与え、また分離性の良い結晶を生成させる観点から、１０００ｒｐｍ以下の速度で攪拌を行うことが好ましく、より好ましくは６００ｒｐｍ以下、更に好ましくは３００ｒｐｍ～１ｒｐｍである。 In the direct transesterification reaction, in the case of stirring, it is preferable to perform stirring at a speed of 1000 rpm or less, more preferably 600 rpm or less, more preferably from the viewpoint of imparting fluidity to fats and oils and producing excellent separable crystals. Preferably, it is 300 rpm to 1 rpm.
　ダイレクトエステル交換反応後の最終的な結晶量は、分別効率の観点からは反応油脂全体中、３重量％～６０重量％が好ましく、より好ましくは５重量％～４０重量％である。前記結晶量は、反応時間でコントロールすれば良く、前記０℃～４０℃、好ましくは１０℃～４０℃でのダイレクトエステル交換反応を、化学触媒使用の場合は１～４８時間、酵素触媒使用の場合は３～１２０時間行うことが好ましい。 The final amount of crystals after the direct transesterification reaction is preferably 3% by weight to 60% by weight, more preferably 5% by weight to 40% by weight, based on the entire reaction fat and oil, from the viewpoint of fractionation efficiency. The amount of crystals may be controlled by the reaction time, and the direct transesterification reaction at 0 ° C. to 40 ° C., preferably 10 ° C. to 40 ° C. is used for 1 to 48 hours when a chemical catalyst is used. In this case, it is preferable to carry out for 3 to 120 hours.
　ダイレクトエステル交換反応を停止する方法は、反応が停止しさえすれば特に問わないが、化学触媒であれば水やクエン酸水の添加などが挙げられ、分別時の機器の劣化を防ぐ観点から酸性物質で中和停止することが好ましい。停止剤の添加量は、分別効率の観点から反応油脂１００重量部に対して０．１重量部～５重量部が好ましく、０．２重量部～１重量部がより好ましい。５重量部より多いと、分別時のろ過効率が悪くなる場合があり、パーム油由来液状油の収率が低下する場合がある。一方、停止剤の添加量が０．１重量部より少ないと、色調が悪くなったり、反応が停止しない場合がある。 The method for stopping the direct transesterification reaction is not particularly limited as long as the reaction is stopped, but if it is a chemical catalyst, water or citric acid can be added, and it is acidic from the viewpoint of preventing deterioration of the equipment during fractionation. It is preferable to stop neutralization with the substance. The addition amount of the terminator is preferably from 0.1 to 5 parts by weight, more preferably from 0.2 to 1 part by weight, based on 100 parts by weight of the reaction fat and oil from the viewpoint of fractionation efficiency. If the amount is more than 5 parts by weight, the filtration efficiency at the time of fractionation may deteriorate, and the yield of palm oil-derived liquid oil may decrease. On the other hand, when the addition amount of the terminator is less than 0.1 parts by weight, the color tone may deteriorate or the reaction may not stop.
　ダイレクトエステル交換反応を停止するタイミングは、パーム油由来液状油の収率の観点からは、反応中の油脂組成中のＳＳＳ含量が３１重量％以下且つＳ２Ｕ含量が１４重量％以下になるまで反応した後が好ましい。より好ましくはパーム油由来液状油の液状性の観点から、ＳＵ２／ＵＵＵ（重量比）が１．９以下、更には１．１以下になるまで反応した後であることが好ましい。 The direct transesterification reaction was stopped from the viewpoint of the yield of palm oil-derived liquid oil until the SSS content in the fat composition during the reaction was 31 wt% or less and the S2U content was 14 wt% or less. The latter is preferred. More preferably, from the viewpoint of the liquid property of the palm oil-derived liquid oil, it is preferable that the reaction is carried out until the SU2 / UUU (weight ratio) is 1.9 or less, further 1.1 or less.
　一方、ダイレクトエステル交換反応を続けるほど反応中の油脂中のＳＳＳ含量が増えてゆくため、反応系中に固体脂が増えすぎて分別しにくくなる。従って、分別効率の観点からは、反応中の油脂中のＳＳＳ含量が５０重量％を超えることなく反応を停止することが好ましく、ＳＳＳ含量が３１重量％を超えることなく反応を停止することがより好ましく、ＳＳＳ含量が１重量％～３１重量％の間で反応を停止することが更に好ましく、１重量％～２５重量％が特に好ましく、１～２０重量％が極めて好ましく、１重量％～１５重量％が最も好ましい。 On the other hand, as the direct transesterification reaction continues, the SSS content in the oil and fat during the reaction increases, so that the solid fat increases in the reaction system and it becomes difficult to separate. Therefore, from the viewpoint of fractionation efficiency, it is preferable to stop the reaction without the SSS content in the oil and fat being reacted exceeding 50% by weight, and it is more preferable to stop the reaction without the SSS content exceeding 31% by weight. Preferably, the reaction is more preferably terminated when the SSS content is between 1% and 31% by weight, particularly preferably between 1% and 25% by weight, very particularly preferably between 1% and 20% by weight, and between 1% and 15% by weight. % Is most preferred.
　また、ダイレクトエステル交換反応を続けるほど反応中の油脂中のＳ２Ｕ含量が減ってゆき、反応後の分別で得られるパーム油由来液状油の液状性の観点からは、反応中の油脂中のＳ２Ｕ含量が１４重量％以下になるまで反応させてから停止することが好ましく、１０重量％以下になるまでがより好ましく、７重量％以下になるまでが更に好ましく、５重量％以下になるまでが最も好ましい。 In addition, the S2U content in the fat during the reaction decreases as the direct transesterification reaction continues, and from the viewpoint of the liquidity of the palm oil-derived liquid oil obtained by fractionation after the reaction, the S2U content in the fat during the reaction. It is preferable to stop the reaction until it is 14% by weight or less, more preferably 10% by weight or less, further preferably 7% by weight or less, and most preferably 5% by weight or less. .
　上記ダイレクトエステル交換後にパーム油由来液状油を分別する方法は、溶剤分別、乾式分別を問わないが、溶剤分別は溶剤の使用により設備費やランニングコストがかかるため、溶剤を使用しない乾式分別が好ましい。溶剤を使用する場合は、ヘキサン、アセトンなどを用いることができる。乾式分別の際の分別温度は、０℃～４５℃が好ましく、より高い液状性を得るために３０℃以下が好ましく、２０℃以下がより好ましく、１０℃以下が更に好ましく、収率の観点も含めると０℃～１０℃が最も好ましい。 The method for fractionating palm oil-derived liquid oil after the direct transesterification is not limited to solvent fractionation and dry fractionation. However, since solvent fractionation requires equipment costs and running costs due to the use of solvent, dry fractionation without using a solvent is preferred. . When using a solvent, hexane, acetone or the like can be used. The fractionation temperature in the dry fractionation is preferably 0 ° C. to 45 ° C., preferably 30 ° C. or less, more preferably 20 ° C. or less, still more preferably 10 ° C. or less in order to obtain higher liquidity, and also the viewpoint of yield. Including 0 to 10 ° C is most preferable.
　本発明の加熱調理油は、上記パーム油由来液状油に加えて、各種用途や素材に応じて、例えばナタネ油、大豆油、パームオレイン、スーパーパームオレイン、綿実油、コーン油、サフラワー油、米油、ヒマワリ油、ハイオレイックひまわり油、ハイオレイックナタネ油、それらの分別油、エステル交換油から選ばれた少なくとも１種の液状油を、加熱調理油全体中に６０重量％以下の量で配合することで、用途や嗜好に応じた風味を得ることができる。なお、前記液状油の量が６０重量％を超え、パーム油由来液状油の量が４０重量％未満になると、フライした際に風味が悪くなり、長時間の使用に耐えられなくなったり、又は低温時に結晶が発生したりする場合がある。 In addition to the above-mentioned palm oil-derived liquid oil, the cooking oil according to the present invention can be used, for example, rapeseed oil, soybean oil, palm olein, super palm olein, cottonseed oil, corn oil, safflower oil, rice, depending on various uses and materials. At least one liquid oil selected from oil, sunflower oil, high oleic sunflower oil, high oleic rapeseed oil, fractionated oils thereof, and transesterified oil is blended in an amount of 60% by weight or less in the whole cooking oil. Thus, it is possible to obtain a flavor according to the purpose and preference. When the amount of the liquid oil exceeds 60% by weight and the amount of the palm oil-derived liquid oil is less than 40% by weight, the flavor deteriorates when fried and cannot be used for a long time, or at low temperatures. Sometimes crystals are generated.
　また、本発明の加熱調理油には、必要に応じて乳化剤、抗酸化剤、シリコーン等を含有させても良い。 In addition, the cooking oil of the present invention may contain an emulsifier, an antioxidant, silicone or the like as necessary.
　本発明の加熱調理油は、通常のフライ油と同様に、例えば素揚げ、から揚げ、天ぷら、フライ等の各種フライ食品や炒め調理に用いることができる。また、この加熱調理油は、非冷凍食品、冷凍食品のどちらにも使用することができる。 The cooking oil of the present invention can be used for various fried foods such as deep-fried food, fried food, tempura, fried food, and stir-fried food, as with ordinary frying oil. Moreover, this cooking oil can be used for both non-frozen foods and frozen foods.
　以下に実施例を示し、本発明をより具体的に説明するが、本発明はこれらの実施例に何ら限定されるものではない。 Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples.
　＜脂肪酸組成の測定＞
　油脂中の脂肪酸組成は、既述の方法により測定した。 <Measurement of fatty acid composition>
The fatty acid composition in fats and oils was measured by the method described above.
　＜油脂中の各トリグリセライド含量の測定＞
　油脂中の各トリグリセライド含量は、既述の方法により測定した。 <Measurement of each triglyceride content in fats and oils>
Each triglyceride content in fats and oils was measured by the method described above.
　＜２位にパルミチン酸を有するグリセライド含量の測定＞
　分析対象の油脂７．５ｇとエタノール２２．５ｇを混合しノボザイム４３５（ノボザイムズジャパン社製）を１．２ｇ加えて３０℃で４時間反応させ、反応液を濃縮後、シリカゲルカラムクロマトグラフィー（型番：シリカゲル６０（０．０６３－０．２００ｍｍ）カラムクロマトグラフィー用、メルク社製）によりトリグリセライド、ジグリセライド、モノグリセライドの各成分に分離し、若干未反応で残るトリグリセライド成分及びジグリセライド成分を除去して、モノグリセライド成分を回収した。そのモノグリセライド０．０５ｇをイソオクタン５ｍｌに溶解し、０．２ｍｏｌ／Ｌナトリウムメチラート／メタノール溶液１ｍｌを加えて７０℃で１５分間反応させることによりメチルエステル化し、酢酸により反応液を中和した後に適量の水を加え、有機相をガスクロマトグラフ（型番：６８９０Ｎ、Ａｇｉｌｅｎｔ社製）によるリテンションタイム及びピークエリア面積により２位にパルミチン酸を有するグリセライド含有量を決定した。 <Measurement of glyceride content with palmitic acid at the 2-position>
7.5 g of analysis fat and oil and 22.5 g of ethanol are mixed, 1.2 g of Novozyme 435 (manufactured by Novozymes Japan) is added and reacted at 30 ° C. for 4 hours, and the reaction solution is concentrated, followed by silica gel column chromatography ( Model No .: Silica gel 60 (0.063-0.200 mm) for column chromatography, manufactured by Merck Ltd.) is separated into triglyceride, diglyceride and monoglyceride components, and the triglyceride component and diglyceride component remaining slightly unreacted are removed. The monoglyceride component was recovered. 0.05 g of the monoglyceride is dissolved in 5 ml of isooctane, 1 ml of 0.2 mol / L sodium methylate / methanol solution is added and reacted at 70 ° C. for 15 minutes to make methyl ester, and after neutralizing the reaction solution with acetic acid, an appropriate amount The glyceride content having palmitic acid at the second position was determined based on the retention time and peak area area of the organic phase by gas chromatography (model number: 6890N, manufactured by Agilent).
　＜曇点＞
　基準油脂分析試験法「２．２．７－１９９６　曇り点」に準じて行なった。 <Cloud point>
It was carried out in accordance with the standard fat and oil analysis test method “2.2.7-1996 Cloud point”.
　＜ＣＤＭ(Conductometric Determination Method)試験（酸化安定性）＞
　基準油脂分析試験法「２．５．１．２－１９９６　ＣＤＭ試験」に準じてＣＤＭ値を測定した。 <CDM (Conductometric Determination Method) test (oxidation stability)>
The CDM value was measured according to the standard fat analysis method “2.5.1.2-1996 CDM test”.
　＜ヨウ素価＞
　基準油脂分析試験法「３．３．３－１９９６　ヨウ素価（ウィイス－シクロヘキサン法）」に準じて測定を行なった。 <Iodine number>
The measurement was carried out according to the standard oil analysis method “3.3.3-1996 Iodine number (Wiis-cyclohexane method)”.
　（製造例１；液状油の作製）
　パームオレイン（ヨウ素価６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ１８重量％、１３．５重量％になったのを確認した後、反応停止剤として水を５０重量部添加して反応を停止した。その後、加熱して全ての結晶を溶解し、７０℃の温水を加え、静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加え、２０分間攪拌後、ろ過することで白土を除き、脱色を行なった。脱色後の温度を４０℃までは１℃／分（設定値）、４０℃から０．２℃／分（設定値）で下げ、１０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が１．１の液状油を３２００重量部（収率：６４％）得た。 (Production Example 1: Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was performed at 30 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 18% by weight and 13.5% by weight, respectively, the reaction was terminated. The reaction was stopped by adding 50 parts by weight of water as an agent. Thereafter, all the crystals were dissolved by heating, warm water at 70 ° C. was added, and the mixture was allowed to stand to separate the oil layer and the water layer, followed by warm water washing for draining and separating. After repeated washing with warm water until the pH of the separated aqueous layer is 8 or less, the oil in the oil layer is heated to 90 ° C., vacuum dewatered, 2 parts by weight of white clay is added, stirred for 20 minutes, and then filtered. Decolorization was performed except for the white clay. The temperature after decolorization is reduced to 1 ° C / min (set value) up to 40 ° C, decreased from 40 ° C to 0.2 ° C / min (set value), and when 10 ° C is reached, the temperature is maintained and measured from the start of temperature decrease. Crystallization continued until 24 hours. After crystallization, by filtering using a filter press (pressurized to 3 MPa), 3200 parts by weight (yield: 64%) of a liquid oil having a SU2 / UUU (weight ratio) of 1.1 in the triglyceride composition is obtained. It was.
　（製造例２；液状油の作製）
　パームオレイン（ヨウ素価５７）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３０℃でダイレクトエステル交換反応を約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２７重量％、１１．６重量％になったのを確認した後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が１．１の液状油を２７００重量部（収率：５４％）得た。 (Production Example 2: Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 57) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 27% by weight and 11.6% by weight, respectively, the reaction was stopped. The reaction was stopped by adding 50 parts by weight of water as an agent. Thereafter, in the same manner as in Production Example 1, 2700 parts by weight (yield: 54%) of a liquid oil having an SU2 / UUU (weight ratio) of 1.1 in the triglyceride composition was obtained.
　（製造例３；液状油の作製）
　パームオレイン（ヨウ素価６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間行った後、更に２５℃で約２４時間該反応を行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２２重量％、９．５重量％になったのを確認した後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．９の液状油を３１００重量部（収率：６２％）得た。 (Production Example 3; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, and further at 25 ° C. for about 24 hours. The SSS content and the S2U content were 22% by weight, respectively, in the total fats and oils during the reaction. After confirming that the amount became 5% by weight, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 3100 parts by weight (yield: 62%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.9 in the triglyceride composition was obtained.
　（製造例４；液状油の作製）
　パームオレイン（ヨウ素価５７）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間行った後、更に２５℃で約２４時間該反応を行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ３０重量％、９．４重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．９の液状油を２６４０重量部（収率：５３％）得た。 (Production Example 4: Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 57) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, and further at 25 ° C. for about 24 hours. The SSS content and the S2U content were 30% by weight in the total fats and oils in the reaction, respectively. After confirming that the amount became 4% by weight, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 2640 parts (yield: 53%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.9 in the triglyceride composition was obtained.
　（製造例５；液状油の作製）
　パームオレイン（ヨウ素価６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間、２７．５℃で約２時間、２５℃で約１２時間、２２．５℃で約２４時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２３重量％、１０．６重量％になったのを確認した後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．７の液状油を３０００重量部（収率：６０％）得た。 (Production Example 5; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, at 27.5 ° C. for about 2 hours, at 25 ° C. for about 12 hours, and at 22.5 ° C. for about 24 hours. After confirming that it became 23% by weight and 10.6% by weight in the whole oil and fat, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 3000 parts by weight (yield: 60%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.7 in the triglyceride composition was obtained.
　（製造例６；液状油の作製）
　パームオレイン（ヨウ素価５７）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間、２７．５℃で約２時間、２５℃で約１２時間、２２．５℃で約２４時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ３０重量％、８．０重量％になったのを確認した後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．７の液状油を２６００重量部（収率：５２％）得た。 (Production Example 6; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 57) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. The temperature was lowered and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, at 27.5 ° C. for about 2 hours, at 25 ° C. for about 12 hours, and at 22.5 ° C. for about 24 hours. After confirming that it became 30 wt% and 8.0 wt% respectively in the whole oil and fat, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 2600 parts by weight (yield: 52%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.7 in the triglyceride composition was obtained.
　（製造例７；液状油の作製）
　パームオレイン（ヨウ素価６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを１０重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間、２７．５℃で約２時間、２５℃で約２時間、２２．５℃で約５時間、１８℃で約１５時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ２９重量％、３．８重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．５の液状油を２７００重量部（収率：５４％）得た。 (Production Example 7; Production of liquid oil)
After adding 5000 parts by weight of palm olein (iodine value 64) to a separable flask and stirring at 100 rpm, vacuum dehydration was performed at 90 ° C., 10 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification was carried out at 30 ° C. for about 8 hours, 27.5 ° C. for about 2 hours, 25 ° C. for about 2 hours, 22.5 ° C. for about 5 hours, and 18 ° C. for about 15 hours. After confirming that the content and S2U content were 29% by weight and 3.8% by weight, respectively, in the total fat and oil during the reaction, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 2700 parts by weight (yield: 54%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.5 in the triglyceride composition was obtained.
　（製造例８；液状油の作製）
　パームオレイン（ヨウ素価６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３６℃で約８時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ１３重量％、１６．５重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が１．３の液状油を３２００重量部（収率：６４％）得た。 (Production Example 8; Production of liquid oil)
After 5000 parts by weight of palm olein (iodine value 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm, 5 parts by weight of sodium methylate was added and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification was carried out at 36 ° C. for about 8 hours. After confirming that the SSS content and the S2U content were 13% by weight and 16.5% by weight, respectively, the reaction terminator The reaction was stopped by adding 50 parts by weight of water. Thereafter, in the same manner as in Production Example 1, 3200 parts by weight (yield: 64%) of a liquid oil having a SU2 / UUU (weight ratio) of 1.3 in the triglyceride composition was obtained.
　（製造例９；液状油の作製）
　パーム油（ヨウ素価５２）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間行った後、更に２５℃で約２４時間該反応を行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ３３重量％、８．６重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．９の液状油を１８００重量部（収率：３６％）得た。 (Production Example 9; Production of liquid oil)
After 5000 parts by weight of palm oil (iodine value 52) was put into a separable flask and stirred at 100 rpm, vacuum dehydration was performed at 90 ° C., 5 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification reaction was carried out at 30 ° C. for about 8 hours, and further at 25 ° C. for about 24 hours. The SSS content and the S2U content were 33% by weight, respectively, in the total fats and oils during the reaction. After confirming that it became 6% by weight, the reaction was stopped by adding 50 parts by weight of water as a reaction terminator. Thereafter, in the same manner as in Production Example 1, 1800 parts by weight (yield: 36%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.9 in the triglyceride composition was obtained.
　（製造例１０；液状油の作製）
　パームオレイン（ヨウ素価５７）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを１０重量部加え、９０℃で２０分間保持した後、降温し、ダイレクトエステル交換反応を３０℃で約８時間、２７．５℃で約２時間、２５℃で約２時間、２２．５℃で約５時間、１８℃で約１５時間行い、ＳＳＳ含量及びＳ２Ｕ含量が反応中の油脂全体中それぞれ３７重量％、３．７重量％になったのを確認後、反応停止剤として水を５０重量部添加して反応を停止した。その後は製造例１と同様にして、トリグリセライド組成中のＳＵ２／ＵＵＵ（重量比）が０．５の液状油を８５０重量部（収率：１７％）得た。 (Production Example 10; Production of liquid oil)
After 5,000 parts by weight of palm olein (iodine number 57) was put into a separable flask and stirred at 100 rpm, vacuum dehydration was performed at 90 ° C., 10 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. The temperature was lowered, and the direct transesterification was carried out at 30 ° C. for about 8 hours, 27.5 ° C. for about 2 hours, 25 ° C. for about 2 hours, 22.5 ° C. for about 5 hours, and 18 ° C. for about 15 hours. After confirming that the content and S2U content were 37% by weight and 3.7% by weight, respectively, in the total fat and oil during the reaction, 50 parts by weight of water was added as a reaction terminator to stop the reaction. Thereafter, in the same manner as in Production Example 1, 850 parts by weight (yield: 17%) of a liquid oil having a SU2 / UUU (weight ratio) of 0.5 in the triglyceride composition was obtained.
　製造例１～１０の製造方法で得られた液状油について、脂肪酸組成、トリグリセライド組成、曇点、ヨウ素価、ＣＤＭ値について分析を行い、それらの結果を表１にまとめた。 The liquid oils obtained by the production methods of Production Examples 1 to 10 were analyzed for fatty acid composition, triglyceride composition, cloud point, iodine value, and CDM value, and the results are summarized in Table 1.
Figure JPOXMLDOC01-appb-T000001
Figure JPOXMLDOC01-appb-T000001
　（製造例１１；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３４℃でダイレクトエステル交換反応を２４時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２０重量％、１０．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、０．２℃／分で降温し、１０℃で１６時間晶析した後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３２００重量部（収率：６４％）得た。 (Production Example 11; production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 3200 parts by weight of liquid oil (yield: 64%). )Obtained.
　（製造例１２；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを１０重量部加え、９０℃で２０分間保持した後、降温し、３０℃到達後、トリパルミチン粉末（ナカライテスク社製）を２５重量部加え、ダイレクトエステル交換反応を４時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２０重量％、１１．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を３０重量部添加して反応を停止した。その後、０．２℃／分で降温し、１０℃で１６時間晶析した後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３２００重量部（収率：６４％）得た。 (Production Example 12; Production of liquid oil)
While adding 5000 parts by weight of palm olein (iodine value: 64) to a separable flask and stirring at 100 rpm, vacuum dehydration was performed at 90 ° C., 10 parts by weight of sodium methylate was added, and the mixture was held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and after reaching 30 ° C., 25 parts by weight of tripalmitin powder (manufactured by Nacalai Tesque) was added, and direct transesterification was performed for 4 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 20% by weight and 11.5% by weight, respectively, 30 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 3200 parts by weight of liquid oil (yield: 64%). )Obtained.
　（製造例１３；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて３００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３４℃でダイレクトエステル交換反応を２４時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２０重量％、１０．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、０．２℃／分で降温し、１０℃で１６時間晶析した後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３２００重量部（収率：６４％）得た。 (Production Example 13; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 300 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 3200 parts by weight of liquid oil (yield: 64%). )Obtained.
　（製造例１４；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて６００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３４℃でダイレクトエステル交換反応を２４時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２０重量％、１０．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、０．２℃／分で降温し、１０℃で１６時間晶析した後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３１５０重量部（収率：６３％）得た。 (Production Example 14; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was placed in a separable flask and stirred at 600 rpm, followed by vacuum dehydration at 90 ° C. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.2 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized up to 3 MPa) to obtain 3150 parts by weight of liquid oil (yield: 63%). )Obtained.
　（製造例１５；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３８℃でダイレクトエステル交換反応を１８時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ１６重量％、１３．０重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３８５０重量部（収率：７７％）得た。 (Production Example 15; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and a direct transesterification reaction was performed at 38 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 16% by weight and 13.0% by weight, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, 3850 parts by weight (yield: 77%) of liquid oil was obtained by filtering using a filter press (pressurized to 3 MPa).
　（製造例１６；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３２℃でダイレクトエステル交換反応を１６時間行なった後、更に降温し、１０℃でダイレクトエステル交換反応を１８時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２２重量％、９．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３１００重量部（収率：６２％）得た。 (Production Example 16; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered and the direct transesterification reaction was carried out at 32 ° C. for 16 hours, then the temperature was further lowered, and the direct transesterification reaction was carried out at 10 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 22% by weight and 9.5% by weight, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, 3100 parts by weight (yield: 62%) of liquid oil was obtained by filtration using a filter press (pressurized to 3 MPa).
　（製造例１７；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３２℃でダイレクトエステル交換反応を１６時間行なった後、更に降温し、１０℃でダイレクトエステル交換反応を１８時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２２重量％、９．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、３０℃まで昇温し、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３３５０重量部（収率：６７％）得た。 (Production Example 17; Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered and the direct transesterification reaction was carried out at 32 ° C. for 16 hours, then the temperature was further lowered, and the direct transesterification reaction was carried out at 10 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 22% by weight and 9.5% by weight, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, it heated up to 30 degreeC and obtained 3350 weight part (yield: 67%) of liquid oils by filter-separating using a filter press (pressurization to 3 Mpa).
　（製造例１８；液状油の作製）
　パームオレイン（ヨウ素価：５７）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３２℃でダイレクトエステル交換反応を１２時間行なった後、更に降温し、２５℃でダイレクトエステル交換反応を２０時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ３０重量％、８．０重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、０．１７℃／分で降温し、１０℃で１６時間晶析した後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を２７００重量部（収率：５４％）得た。 (Production Example 18; Production of liquid oil)
5000 parts by weight of palm olein (iodine number: 57) was placed in a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered and a direct transesterification reaction was carried out at 32 ° C. for 12 hours, then the temperature was further lowered, and a direct transesterification reaction was carried out at 25 ° C. for 20 hours. At that time, after confirming that the SSS content and S2U content in the whole fat and oil during the reaction were 30% by weight and 8.0% by weight, respectively, 15 parts by weight of 25% aqueous citric acid was added as a reaction terminator. The reaction was stopped. Thereafter, the temperature was lowered at 0.17 ° C./min, crystallized at 10 ° C. for 16 hours, and then filtered using a filter press (pressurized to 3 MPa) to obtain 2700 parts by weight of liquid oil (yield: 54%). )Obtained.
　（製造例１９；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、５０℃に降温してリパーゼ（ノボザイムズ社製「Ｌｉｐｏｚｙｍｅ　ＴＬ　ＩＭ」）を５００重量部加え、５０℃で４時間保持した後、降温し、３６℃でダイレクトエステル交換反応を３８時間行なった後、更に降温し、１０℃で１８時間ダイレクトエステル交換反応を行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２２重量％、９．５重量％になったのを確認した後、酵素を含んだまま１０℃でフィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を２８５０重量部（収率：５７％）得た。 (Production Example 19; Production of liquid oil)
While adding 5000 parts by weight of palm olein (iodine value: 64) to a separable flask and stirring at 100 rpm, vacuum dehydration was carried out at 90 ° C., and then the temperature was lowered to 50 ° C. and lipase (“Lipozyme TL IM” manufactured by Novozymes) ) Was added and held at 50 ° C. for 4 hours, the temperature was lowered, direct transesterification was performed at 36 ° C. for 38 hours, the temperature was further lowered, and direct transesterification was performed at 10 ° C. for 18 hours. At that time, after confirming that the SSS content and S2U content in the total fat and oil during the reaction were 22% by weight and 9.5% by weight, respectively, a filter press (pressurized up to 3 MPa) at 10 ° C. with the enzyme contained. ) To obtain 2850 parts by weight of liquid oil (yield: 57%).
　（製造例２０；液状油の作製）
　パームオレイン（ヨウ素価：６４）５０００重量部をセパラブルフラスコに入れて１００ｒｐｍで攪拌しながら、９０℃で真空脱水を行なった後、ナトリウムメチラートを５重量部加え、９０℃で２０分間保持した後、降温し、３４℃でダイレクトエステル交換反応を２４時間行なった。その時点で反応中の油脂全体中のＳＳＳ含量及びＳ２Ｕ含量がそれぞれ２０重量％、１０．５重量％になったのを確認した後、反応停止剤として２５％クエン酸水を１５重量部添加して反応を停止した。その後、加熱して全ての結晶を溶解し、７０℃の温水を加えてから静置して油層と水層を分離し、水を抜いて分離する温水洗浄を行った。分離した水層のｐＨが８以下になるまで該温水洗浄を繰り返した後、油層の油脂を９０℃に加熱し、真空脱水を行ない、白土を２重量部加えて２０分間攪拌した後、ろ過することで白土を除いて脱色を行なった。脱色後の油脂温度を、４０℃になるまでは１℃／分（設定値）で、４０℃からは０．２℃／分（設定値）で降温し、１０℃に到達したらその温度を保持し、降温開始時から計２４時間になるまで晶析した。晶析後、フィルタープレス（３ＭＰａまで加圧）を用いてろ別することで、液状油を３２００重量部（収率：６４％）得た。 (Production Example 20: Production of liquid oil)
5000 parts by weight of palm olein (iodine value: 64) was put into a separable flask and vacuum dehydrated at 90 ° C. while stirring at 100 rpm. Then, 5 parts by weight of sodium methylate was added and held at 90 ° C. for 20 minutes. Thereafter, the temperature was lowered, and direct transesterification was performed at 34 ° C. for 24 hours. At that time, after confirming that the SSS content and S2U content in the entire fat and oil during the reaction were 20 wt% and 10.5 wt%, respectively, 15 parts by weight of 25% citric acid water was added as a reaction terminator. The reaction was stopped. Then, all the crystals were dissolved by heating, and after adding 70 ° C. warm water, the mixture was allowed to stand to separate the oil layer and the aqueous layer, and the hot water washing was performed to remove the water and separate it. The hot water washing is repeated until the pH of the separated aqueous layer becomes 8 or less, and then the oil and fat in the oil layer is heated to 90 ° C., vacuum dehydration is performed, 2 parts by weight of white clay is added, and the mixture is stirred for 20 minutes and then filtered. In this way, decolorization was performed except for the white clay. The oil and fat temperature after decolorization is 1 ° C / min (set value) until 40 ° C and from 40 ° C to 0.2 ° C / min (set value), and when it reaches 10 ° C, the temperature is maintained. Then, crystallization was performed until 24 hours in total from the start of temperature drop. After crystallization, 3200 parts by weight (yield: 64%) of liquid oil was obtained by filtering using a filter press (pressurized to 3 MPa).
　上記製造例１１～２０で得られた液状油の分析値を表２にまとめた。 The analytical values of the liquid oil obtained in Production Examples 11 to 20 are summarized in Table 2.
Figure JPOXMLDOC01-appb-T000002
Figure JPOXMLDOC01-appb-T000002
（実施例１、２、比較例１、２）
　＜フライ試験＞
　表３に示す各種の油脂を１０００ｇずつ電気フライヤーに入れ、油温を１８０℃に保持したまま、１時間毎に１回、冷凍ポテト５０ｇを投入して５分間フライしてフライドポテトを作った。これを１日８時間、４日間連続して行い、１日目にフライしたフライドポテトと比較して、４日目にフライしたフライドポテトの風味評価を行った。
　評価は、パネラー８名により下記の５点法で評価し、８名の評価の平均点の小数点第２位を四捨五入して各油脂の評価とした。
　５点：１日目のフライドポテトの風味と同様に劣化臭がせず、極めて良好。
　４点：１日目のフライドポテトの風味とほぼ同様に劣化臭がせず、良好。
　３点：１日目のフライドポテトの風味と較べてやや劣化臭がし、やや劣る。
　２点：１日目のフライドポテトの風味と較べて劣化臭がし、劣る。
　１点：１日目のフライドポテトの風味と較べてかなり劣化臭がし、極めて劣る。 (Examples 1 and 2, Comparative Examples 1 and 2)
<Fly test>
1000 g of each type of fats and oils shown in Table 3 was put into an electric fryer, and while maintaining the oil temperature at 180 ° C., 50 g of frozen potato was added once every hour and fried for 5 minutes to make fries. This was performed for 8 hours a day for 4 consecutive days, and the flavor evaluation of the fries fried on the 4th day was performed in comparison with the fries fried on the 1st day.
Evaluation was made by the following five-point method by eight panelists and rounded off to the second decimal place of the average score of the eight persons' evaluations to evaluate each oil and fat.
5 points: No deterioration odor similar to the flavor of French fries on the first day, and very good.
4 points: No deterioration odor, almost the same as the flavor of French fries on the first day, good.
3 points: Slightly deteriorated smell and slightly inferior to the flavor of French fries on the first day.
2 points: Deteriorated smell and inferior to the flavor of French fries on the first day.
1 point: Compared with the flavor of French fries on the first day, it has a considerably deteriorated odor and is extremely inferior.
　＜冷蔵試験＞
　上記と同じ各油脂１００ｇを４℃の恒温槽に入れ、１週間後の油脂の状態を観察した。 <Refrigeration test>
100 g of each of the same fats and oils as described above was placed in a constant temperature bath at 4 ° C., and the state of the fats and oils after 1 week was observed.
　以上のフライ試験及び冷蔵試験の結果を表３に示す。 Table 3 shows the results of the above fly test and refrigeration test.
Figure JPOXMLDOC01-appb-T000003
Figure JPOXMLDOC01-appb-T000003
　表３に示すように、パーム油由来液状油を用いた本発明の加熱調理油は、フライ時の油脂の劣化が抑制され、風味が悪くなりにくく長期間使用することが出来るとともに、低温での保存性も良好であった。 As shown in Table 3, the cooking oil according to the present invention using a palm oil-derived liquid oil can be used for a long period of time, with less deterioration of oil and fat during frying, less likely to deteriorate in flavor, and at low temperatures. Preservability was also good.

Claims (3)

  1. 　パーム系油脂を主原料とし、ＳＵ２／ＵＵＵ重量比が１．９以下且つＳＳＳ含量が２重量％以下で２位にパルミチン酸が結合したグリセライドを液状油全体中１０～３０重量％含有するパーム油由来液状油を、加熱調理油全体中４０～１００重量％含有する加熱調理油。 Palm oil containing palm oil and fat as the main raw material, and having a SU2 / UUU weight ratio of 1.9 or less, an SSS content of 2 wt% or less, and 10-30 wt% of glyceride bonded with palmitic acid at the 2-position Cooking oil containing 40 to 100% by weight of liquid oil derived from the whole cooking oil.
  2. 　前記パーム油由来液状油の曇点が０～－１２℃である請求項１に記載の加熱調理油。 The cooking oil according to claim 1, wherein the cloud point of the palm oil-derived liquid oil is 0 to -12 ° C.
  3. 　前記パーム油由来液状油のＣＤＭ値が５時間以上である請求項１又は２に記載の加熱調理油。 The cooking oil according to claim 1 or 2, wherein the palm oil-derived liquid oil has a CDM value of 5 hours or more.
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JPS6214743A (en) * 1985-07-09 1987-01-23 ユニリ−バ−　ナ−ムロ−ゼ　ベンノ−トシヤ−プ Hard stock, fat blend containing hard stock and its production
JPH0686636A (en) * 1992-09-08 1994-03-29 Asahi Denka Kogyo Kk Production of oil and fat composition for confectionery
JPH07135901A (en) * 1993-11-18 1995-05-30 Asahi Denka Kogyo Kk Production of fat and oil composition for confectionery
JP2000282080A (en) * 1999-03-31 2000-10-10 Yoshihara Oil Mill Ltd Mixed edible oil and its use
JP2005160453A (en) * 2003-11-12 2005-06-23 Nisshin Oillio Group Ltd Oil and fat composition for frying and fried food
WO2011132734A1 (en) * 2010-04-22 2011-10-27 株式会社カネカ Liquid oil and fat, and production method therefor

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Publication number Priority date Publication date Assignee Title
JPS6214743A (en) * 1985-07-09 1987-01-23 ユニリ−バ−　ナ−ムロ−ゼ　ベンノ−トシヤ−プ Hard stock, fat blend containing hard stock and its production
JPH0686636A (en) * 1992-09-08 1994-03-29 Asahi Denka Kogyo Kk Production of oil and fat composition for confectionery
JPH07135901A (en) * 1993-11-18 1995-05-30 Asahi Denka Kogyo Kk Production of fat and oil composition for confectionery
JP2000282080A (en) * 1999-03-31 2000-10-10 Yoshihara Oil Mill Ltd Mixed edible oil and its use
JP2005160453A (en) * 2003-11-12 2005-06-23 Nisshin Oillio Group Ltd Oil and fat composition for frying and fried food
WO2011132734A1 (en) * 2010-04-22 2011-10-27 株式会社カネカ Liquid oil and fat, and production method therefor

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016089004A (en) * 2014-11-04 2016-05-23 日清オイリオグループ株式会社 Oil and fat composition

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