JP5161465B2 - Method for producing highly liquid palm oil and highly liquid palm oil - Google Patents

Description

  The present invention relates to a method for producing a highly liquid palm oil and a highly liquid palm oil, in which a highly liquid oil is obtained from palm-based fats and oils by repeating enzymatic transesterification and fractionation.

  Rapeseed oil such as canola is the mainstream as household salad oil. However, recently, due to the rapid spread of biodiesel in Europe and the like, the price of rapeseed oil has soared and the production cost of salad oil has increased. In addition, rapeseed oil is expected to tighten in the future. Therefore, it is extremely meaningful if salad oil can be produced using palm oil and fat which is inexpensive and stable in supply.

  As a method for obtaining highly liquid oil from palm-based fats and oils, there is a chemical transesterification method using an alkali catalyst. In directed transesterification disclosed in Non-Patent Document 1, palm oil is transesterified at around 30 ° C. using an alkali catalyst. It is described that a highly liquid oil can be obtained by crystallizing trisaturated fatty acid glycerides and allowing the reaction to proceed while removing them from the reaction system. However, in this method, catalyst removal is complicated and the yield is poor. In order to improve the yield, solvent fractionation is required, and the work becomes more complicated.

  Non-Patent Document 2 discloses a multistage dry fractionation method. In this method, dry fractionation is performed three times from palm oil to obtain a highly liquid palm oil having an iodine value of 70. The obtained highly liquid palm oil alone clears the salad oil cooling test, but the yield is low and the production time is also long.

Non-Patent Document 3 describes performing chemical transesterification and fractionation. Transesterification of palm oil is performed using an alkali catalyst, and after removing the catalyst, the high melting point portion is removed by separation to obtain a liquid portion. However, this method also requires complicated catalyst removal, yields are poor, and liquidity is not sufficient.
JP-A 61-293389 JP-A-8-38190 Regina C.I. A. Lago and Leopold Hartman, J.A. Sci. Food Agric, 37, pp. 689-693 (1986) Dry multiple fractionation: trends in products and applications, Lipid Technology, 7, pp. 34-38 (1995.3) U.S. Pat. No. 2,442,531

  As described above, in the chemical transesterification method, catalyst removal is complicated and the yield is poor. In order to improve the yield, solvent fractionation is required, and the work becomes more complicated. Moreover, even if it refine | purifies by the influence which uses an alkali catalyst, the flavor of oil is bad and a color also becomes dark. In the multistage fractionation method, the yield is low and the production time is long. Furthermore, the liquidity is not sufficient.

  In order to solve the above problems, there is a method of obtaining high-liquid palm oil by enzymatic transesterification of palm oil (Patent Documents 1 and 2). However, the conventional method still does not have sufficient liquidity, and a product suitable for use in salad oil or the like that requires particularly high liquidity has not been obtained. In addition, conventionally, a mixture of palm-based fats and other highly liquid oils is used as a raw material, and a high-liquid oil is obtained in a high yield using palm-based fats alone. Was still difficult.

  The present invention has been made in view of the above circumstances, and provides a method for producing palm oil with improved liquidity and high liquid palm oil by a simple operation with high yield.

According to the present invention, (A) a step of transesterifying palm oil fat using a lipase having random transesterification ability ;
(B) The step of separating the transesterified oil and fat obtained in the step of transesterification to remove SSS (S means saturated fatty acid, SSS means triglyceride composed of three saturated fatty acids);
In the manufacturing method of the palm oil containing A, the manufacturing method of the highly liquid palm oil which repeats the series of processes which consist of the said process (A) and (B) twice or more is provided.

The production method of the present invention is characterized by repeating a series of cycles in which high-melting triglycerides are removed by fractionation after transesterification using lipase in order to enhance the liquidity of palm-based fats and oils. By performing the transesterification of palm oil and fat, the saturated fatty acid in the oil and fat is converted to a high-saturation tri-saturated fatty acid glyceride, which is then separated and removed. By repeating this series of steps twice or more, the saturated fatty acid in the oil and fat can be remarkably reduced, and the liquidity is improved.
Further, in the present invention, enzymatic transesterification using lipase is performed, so that a catalyst removal step such as water washing is unnecessary and the operation is simple and the yield is good as compared with the case of using chemical transesterification. Even the separation does not require a particularly complicated operation, and the time required is also relatively short. Moreover, since an alkali catalyst is not used, the flavor of the obtained liquid oil is favorable and a color does not become dark.

Moreover, according to this invention, the manufacturing method of highly liquid palm oil which repeats a series of operation which performs a process (B) after a process (A) 3 times or more is provided .
Et al is, according to the present invention, in the step (B), a fractionated by dry fractionation, the method of producing a high liquid resistance palm oil is provided.

Furthermore, according to the present invention, high-liquid palm oil obtained by the production method of the present invention ,
(I) PPP (P means palmitic acid, PPP means tripalmitin composed of three palmitic acids) content is 0.2 mass% or less,
(Ii) P ₂ O (O means oleic acid, P ₂ O means triglyceride composed of two palmitic acids and one oleic acid) content of 16% by mass or less,
(Iii) POP / (POP + PPO) (POP means triglyceride composed of 1 and 3 positions palmitic acid, 2 position oleic acid, PPO 1 and 2 position palmitic acid, 3 position composed of oleic acid The triglyceride and the triglyceride composed of palmitic acid at positions 2 and 3 and oleic acid at position 1)
(Iv) iodine value is 70 or more,
A highly liquid palm oil is provided.

Furthermore, according to this invention, the salad oil obtained by mixing the high-liquid palm oil in the said this invention individually or with another liquid oil is provided.
In this invention, heat resistance improves by using highly liquid palm oil for salad oil. Therefore, it lasts longer than normal salad oil mainly composed of rapeseed oil, and from the viewpoint of environment, considering waste oil treatment and the like.

  According to the present invention, a highly liquid palm oil suitable for salad oil having a high liquidity and a good flavor can be obtained in a high yield using a simple method. Furthermore, since high-liquid palm oil is used, it can last longer than normal rapeseed oil-based salad oil, and can provide environmentally friendly salad oil in consideration of waste oil treatment.

  Embodiments of the present invention will be described below. In the description of the present invention, S means saturated fatty acid, P means palmitic acid, O means oleic acid, and L means linoleic acid. SSS means triglyceride composed of three saturated fatty acids, PPP means tripalmitin composed of three palmitic acids, and OOO means triolein composed of three oleic acids. Further, POP is a triglyceride composed of palmitic acid at positions 1 and 3 and oleic acid at position 2, PPO is a triglyceride composed of palmitic acid at positions 1 and 2, and 3 and 3 with oleic acid. It includes both palmitic acid at the position and triglyceride composed of oleic acid at the position 1. PLP is a triglyceride composed of palmitic acid at positions 1 and 3 and linoleic acid at position 2, PLO is a triglyceride composed of palmitic acid at position 1, linoleic acid at position 2, oleic acid at position 3, and 3 It includes both triglycerides composed of palmitic acid at position 2, linoleic acid at position 2, and oleic acid at position 1.

  A process flow of the manufacturing method of the present invention is shown in FIG. The method of the present invention comprises a series of cycles in which high melting point triglycerides are removed by separating the solid part and the liquid part after transesterification using lipase in order to enhance the liquid property of the palm-based fats and oils. Repeated twice or more.

FIG. 2 is a diagram conceptually showing random transesterification of palm-based fats and oils. By carrying out random transesterification of palm oil and fat, high melting point trisaturated fatty acid glycerides (SSS) such as PPP increase in the oil and fat. Palm oils and fats contain a large amount of POP, and PPO, OOP, PLP, POL, OOO, etc. are mixed as other components.
The POP ratio based on the sum of POP and PPO in palm-based fats and oils is usually about 0.9 to about 0.8. By performing random transesterification, PPP, PPO, OOO, and the like are formed, and the ratio of POP decreases (see FIG. 2). Thereafter, trisaturated fatty acid glycerides (SSS) such as PPP are removed by separation, and the liquidity can be improved by reducing the saturated fatty acids in the fats and oils. Furthermore, by repeating this series of steps, liquidity can be further enhanced.

  In the present invention, since the enzymatic transesterification is performed, a highly liquid palm oil having a higher yield and a better flavor than a system using chemical transesterification can be obtained. In addition, the method using enzymatic transesterification does not require complicated work for removing the catalyst, reduces the amount of waste water, and is excellent in terms of environment. Therefore, since the operation is simple, the equipment cost and utility cost can be greatly reduced.

  The term palm oil and fat used as a raw material in the present invention includes refined and unrefined palm oil and palm olein obtained by one or more fractionations. As a raw material, it may be used alone or mixed with other fats and oils. However, in the present invention, high-liquid palm oil can be obtained from the palm-based oil / fat raw material without mixing other high-liquid oil / fat. Therefore, when palm fats and oils occupy most of the raw material, for example, when palm fats and oils are used alone or substantially alone, or when the mixing ratio of other fats and oils is 10% by mass or less, The effect of the present invention becomes remarkable.

  The lipase used for the enzymatic transesterification is not particularly limited. However, since those having 1,3-position specificity may not exhibit sufficient effects, those having random transesterification ability are preferred.

  The enzymatic transesterification reaction conditions are not particularly limited as long as the conditions reach equilibrium (particularly randomization). The reaction form may be a column packing type, a batch type, or other forms.

  For the fractionation, dry fractionation or solvent fractionation can be used. However, it is preferable to use dry fractionation because solvent fractionation is expensive and the operation is complicated. In the present invention, even when dry fractionation is used, a liquid part having high quality can be obtained with high yield.

  Although the conditions for fractionation are not particularly limited, the separation is performed under conditions for separating the transesterified oil and fat and removing SSS. Since the separation is performed a plurality of times, the conditions may be changed in the first and subsequent separations and the last separation. Preferably, except for the last fractionation, it is carried out under conditions that remove only tri-saturated fatty acid glycerides (SSS) such as PPP. At this stage, it is not always necessary to completely remove SSS, and about 2 to 3% by mass may remain. Rather, when considering the fractionation time and the yield other than the last fractionation, it is better to carry out under conditions such that about 2 to 3% by mass of SSS remains. As such a separation condition, for example, the separation temperature is preferably about 25 to 35 ° C. and about 30 minutes to 2 hours.

On the other hand, in the last fractionation, it is preferable to remove SSS almost completely and to remove P ₂ O, which is a medium melting point, to some extent in order to improve liquidity. As such a separation condition, for example, the final temperature of the separation is preferably about 0 to 10 ° C. and about 30 minutes to 3 hours.

When the final liquid part (oil composition) has a PPP of 0.2% by mass or less and a P ₂ O content of 16% by mass or less, the rapeseed oil and 50% blending clear the cooling test of the salad oil standard. Furthermore, PPP is less than 0.05 wt%, to clear the cooling test salad oil standards alone when the _{P 2} O is 12 wt% or less.
Except for the last fractionation, when the separation is performed under conditions that are not so severe that a little SSS remains, complication of the process can be avoided while maintaining a high yield.

The series of operations of enzymatic transesterification-fractionation is repeated twice or more, preferably three or more times. By such a method, highly liquid palm oil which can prepare salad oil by high mixing | blending is obtained. Even when a series of operations of enzymatic transesterification-fractionation is performed once, it is possible to obtain the oil composition corresponding to the above, but a palm-based oil with a high yield and a small amount of PPP can be obtained by a single operation. It is difficult. That is, if the PPP is completely removed by only one series of operations described above, the separation conditions become strict and the yield deteriorates. On the other hand, if the yield is to be improved, the obtained oil / fat composition may depart from the preferred PPP and P ₂ O ranges described above, and sufficient liquidity may not be obtained.

  Here, the POP / PPO ratio is changed by enzymatic random transesterification. The ratio of POP in palm-based fats and oils is about 0.9 to about 0.8 when the total of POP and PPO is used as a reference. On the other hand, when random transesterification is performed, the POP ratio based on the sum of POP and PPO is about 0.33. The POP ratio based on the sum of POP and PPO in the finally obtained highly liquid palm oil is preferably 0.3 or more and 0.6 or less, more preferably 0.4 or more and 0.55. It is as follows.

FIG. 3 shows the relationship between the POP / PPO ratio and the melting point. According to the phase diagram of POP / PPO, a molecular compound is formed when POP / PPO is 50/50, and P ₂ O has the lowest melting point. Therefore, when the ratio of POP of the finally obtained oil and fat composition is about 0.5 on the basis of the sum of POP and PPO, the composition having the same P ₂ O content is most liquid. A high one is obtained. It can be seen from the phase diagram that the temperature of precipitation as P ₂ O is lower when random transesterification is performed. Therefore, since the difference between the melting points of PPP and P ₂ O increases when random transesterification is performed, the temperature at the time of fractionation can be increased, PPP can be easily removed, and the yield is improved.

  The number of repetitions of the series of operations is preferably about 2 to 4 times in consideration of manufacturing costs and the like.

Palm oil produced by the method of the present invention has high liquidity. Specifically, the highly liquid palm oil of the present invention has a PPP content of 0.2% by mass or less and a P ₂ O content of 16% by mass or less. Within this range, the high-liquid palm oil can clear the cooling test of the salad oil standard when the rapeseed oil content is 50% by mass or less.
More preferably, the PPP content is less than 0.05% by mass, and the P ₂ O content is 12% by mass or less.

Furthermore, in the highly liquid palm oil of the present invention, the POP ratio is 0.3 or more and 0.6 or less based on the total of POP and PPO, and POP relative to PPO compared to normal palm oil and fat. The ratio is small. More preferably, the ratio of POP is 0.4 or more and 0.55 or less on the basis of the sum of POP and PPO. On the other hand, the ratio of POP of the palm-based fat raw material that has not been transesterified is usually about 0.9 to about 0.8 on the basis of the total of POP and PPO. As described above, if the composition has the same P ₂ O content, the POP / PPO ratio is about 50/50, that is, the POP ratio is about 0.5 based on the sum of POP and PPO. In addition, it has the highest liquidity. Since the POP ratio with respect to PPO is reduced, the highly liquid palm oil of the present invention has higher liquidity than a composition having the same P ₂ O content not transesterified.

  The highly liquid palm oil of the present invention has an iodine value of 70 or more and high liquidity. The iodine value is an index indicating the amount of unsaturated bonds. The higher the iodine value, the higher the amount of unsaturated fatty acid, and the higher the liquidity, which is preferable.

  Furthermore, since the highly liquid palm oil of this invention is manufactured without using an alkali catalyst in the transesterification, it has a good flavor and low chromaticity. Moreover, compared with transesterification oil using rapeseed oil or an alkali catalyst, it is excellent in heat resistance and has a low coloring increase rate.

  Therefore, the highly liquid palm oil of the present invention has high liquidity and is suitable for use in salad oil. Moreover, compared with the conventional rapeseed oil-based salad oil, the salad oil prepared by blending the high-liquid palm oil of the present invention with a high blending is excellent in heat resistance and also lasts long when used as a frying oil. In addition, rapeseed oil is expected to increase in price due to the spread of biodiesel in the future, and the supply side will be tight, but in the present invention, by using palm oil, salad oil that is relatively stable in price and supply side can be obtained. It becomes possible to supply.

  As mentioned above, although embodiment of this invention was described, these are illustrations of this invention and various structures other than the above are also employable.

Example 1
Nitrogen bubbling of palm olein with an iodine value of 57 at 60 ° C. under reduced pressure was performed at a flow rate of 1.3 kg / h through a 10 cm diameter column packed with about 4 kg of Lipozyme TL IM (Novozymes) with a residual water content of 50 ppm or less. The solution was transesterified. The obtained transesterified oil and fat had a PPP content of 11% by mass, a P ₂ O content of 28% by mass, and a POP / (POP + PPO) ratio of 0.3, which was almost randomized. 10 kg of this transesterified oil / fat was completely dissolved at 70 ° C. using Lab Pilot Fraction Unit (10 kg, the following fractionation was also performed using the same equipment) manufactured by De Smet, and then rapidly cooled to 28 ° C. and then 90 ° C. at 32 ° C. Perform crystallization, filter with a filter press (pressurize up to 12 bar), and remove the liquid part with an iodine value of 62, a PPP content of 3% by mass, a P ₂ O content of 30% by mass, and a POP / (POP + PPO) ratio of 0.33. Yield was 80% (first cycle). This liquid part was subjected to nitrogen bubbling under reduced pressure at 60 ° C. to reduce the residual moisture to 50 ppm or less, and transesterification was performed under the same conditions to obtain a transesterified oil and fat having a PPP content of 9% by mass and a P ₂ O content of 24% by mass. . 10 kg of this transesterified fat / oil is completely dissolved at 70 ° C. and then rapidly cooled to 26 ° C., followed by crystallization at 32 ° C. for 40 minutes, 30 ° C. for 30 minutes, and 28 ° C. for 40 minutes, and filter press (pressurized to 12 bar) And a liquid part having an iodine value of 66, a PPP content of 2% by mass and a P ₂ O content of 25% by mass was obtained in a yield of 85% (second cycle). The obtained liquid part was subjected to nitrogen bubbling under reduced pressure at 60 ° C. to reduce the residual moisture to 50 ppm or less, and transesterification was performed again under the same conditions. The PPP content was 6% by mass, the P ₂ O content was 22% by mass, and POP / ( A transesterified oil with a POP + PPO ratio of 0.26 was obtained. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C., then rapidly cooled to 19 ° C., and then crystallized at 25 ° C. for 45 minutes, 20 ° C. for 30 minutes, 15 ° C. for 90 minutes, 10 ° C. for 90 minutes, and 5 ° C. for 120 minutes. The liquid part having an iodine value of 75, a PPP content of 0.1% by mass, a P ₂ O content of 14% by mass, and a POP / (POP + PPO) ratio of 0.47 is separated by a filter press (pressurized up to 12 bar). The yield was 66% (third cycle). The yield from palm olein was 45%. The POP / (POP + PPO) ratio was determined by liquid chromatography. First, an ODS column (for example, LiChrosorb RP-18 5 μm / GL-Pack, manufactured by GL Sciences) was used to fractionate triglyceride species to obtain P ₂ O. After fractionation, the P ₂ O fraction was fractionated from POP and PPO using a silver ion column (for example, ChromSpher 5 Lipids, manufactured by Varian), and the ratio was measured.

(Example 2)
The transesterified oil (PPP content 6% by mass, P ₂ O content 22% by mass, POP / (POP + PPO) ratio 0.26) before fractionation in the third cycle of Example 1 was completely dissolved at 70 ° C. and then 1200 g in a 2000 ml beaker. The sample was sampled and rapidly cooled to 12 ° C. while stirring with a stirrer (20 rpm), followed by crystallization at 25 ° C. for 60 minutes, 20 ° C. for 30 minutes, 15 ° C. for 30 minutes, and 10 ° C. for 30 minutes. The pressure was reduced to 12 bar, and a liquid part having an iodine value of 76, a PPP content of 0% by mass, a P ₂ O content of 16% by mass, and a POP / (POP + PPO) ratio of 0.48 was obtained in a yield of 64%. The yield from palm olein was 44%.

(Example 3)
The transesterified oil (PPP content 6% by mass, P ₂ O content 22% by mass, POP / (POP + PPO) ratio 0.26) before fractionation in the third cycle of Example 1 was completely dissolved at 70 ° C. and then 1200 g in a 2000 ml beaker. The sample was sampled and rapidly cooled to 12 ° C. while stirring with a stirrer (20 rpm), and then crystallized at 25 ° C. for 60 minutes, 20 ° C. for 30 minutes, 15 ° C. for 30 minutes, 10 ° C. for 30 minutes, and 5 ° C. for 30 minutes. And filtered with a filter press (pressurized to 12 bar) to obtain a liquid part having an iodine value of 78, a PPP content of 0% by mass, a P ₂ O content of 12% by mass, and a POP / (POP + PPO) ratio of 0.49. %. The yield from palm olein was 41%.

(Comparative Example 1)
10 kg of transesterified oil and fat (PPP content 11% by mass, P ₂ O content 28% by mass, POP / (POP + PPO) ratio 0.30) before fractionation in the first cycle of Example 1 was supplied by De Smet Lab Pilot Fractionation Unit ( 10 kg), after complete dissolution at 70 ° C., rapidly cool to 28 ° C., then, 32 ° C. for 90 minutes, 25 ° C. for 45 minutes, 20 ° C. for 30 minutes, 15 ° C. for 90 minutes, 10 ° C. for 90 minutes, Crystallization is carried out at 5 ° C. for 120 minutes, and filtered with a filter press (pressurized up to 12 bar). The iodine value is 72, the PPP content is 0.5 mass%, the P ₂ O content is 18 mass%, and the POP / (POP + PPO) ratio is 0. .45 liquid part was obtained in 18% yield from palm olein. The filterability was very poor.

(Comparative Example 2)
1 kg of palm olein having an iodine value of 57 is charged into a reactor equipped with a stirrer, and nitrogen bubbling is performed at 60 ° C. under reduced pressure to reduce the residual moisture to 50 ppm or less, and then the catalyst is cooled to 20 ° C. under a nitrogen stream. 3 g of sodium methoxide was added. After stirring at 20 ° C. for 48 hours under a nitrogen stream, the precipitated crystals were filtered off with a filter press (pressurized to 12 bar) (filterability was very poor). In order to remove the catalyst from the obtained liquid reaction product, it was washed with water until neutral, and then water was removed under reduced pressure to obtain an oil and fat composition with a yield of 20% from palm olein. The obtained oil and fat composition had an iodine value of 69, a PPP content of 1.5% by mass, a P ₂ O content of 20% by mass, and a POP / (POP + PPO) ratio of 0.43.

(Comparative Example 3)
A reactor equipped with a stirrer was charged with 10 kg of palm olein having an iodine value of 57, subjected to nitrogen bubbling at 60 ° C. under reduced pressure to reduce the residual moisture to 50 ppm or less, and then 30 g of sodium methoxide as a catalyst under a nitrogen stream. Was added. The mixture was stirred at 60 ° C. for 2 hours under a nitrogen stream to perform transesterification. After washing with water until the catalyst became neutral in order to remove the catalyst, water was removed under reduced pressure to obtain a transesterified oil and fat with a yield of 93%. The obtained transesterified oil had a PPP content of 10% by mass, a P ₂ O content of 27% by mass, and a POP / (POP + PPO) ratio of 0.36, which was almost randomized. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C. using Lab Pilot Fraction Unit (10 kg) of De Smet, and then rapidly cooled to 28 ° C., followed by crystallization at 32 ° C. for 90 minutes, followed by filter press (up to 12 bar) Pressure), a liquid part having an iodine value of 62, a PPP content of 3% by mass, a P ₂ O content of 31% by mass and a POP / (POP + PPO) ratio of 0.33 was obtained in a yield of 77% (first cycle). . This liquid part was transesterified in the same manner as described above to obtain a transesterified oil and fat having a PPP content of 8% by mass and a P ₂ O content of 24% by mass in a yield of 94%. 10 kg of this transesterified fat / oil is completely dissolved at 70 ° C. and then rapidly cooled to 26 ° C., followed by crystallization at 32 ° C. for 40 minutes, 30 ° C. for 30 minutes, and 28 ° C. for 40 minutes, and filter press (pressurized to 12 bar) And a liquid part having an iodine value of 66, a PPP content of 2% by mass and a P ₂ O content of 24% by mass was obtained in a yield of 81% (second cycle). This liquid part was transesterified again in the same manner as described above, and a transesterified oil and fat having a PPP content of 6% by mass, a P ₂ O content of 22% by mass and a POP / (POP + PPO) ratio of 0.32 was obtained at a yield of 94%. Obtained. 10 kg of this transesterified oil / fat is completely dissolved at 70 ° C., then rapidly cooled to 19 ° C., and then crystallized at 25 ° C. for 45 minutes, 20 ° C. for 30 minutes, 15 ° C. for 90 minutes, 10 ° C. for 90 minutes, and 5 ° C. for 120 minutes. The liquid part having an iodine value of 75, a PPP content of 0.1% by mass, a P ₂ O content of 14% by mass, and a POP / (POP + PPO) ratio of 0.49 is filtered. The yield was 60% (third cycle). The yield from palm olein was 31%. Compared with Example 1, the yield was considerably inferior.

(Test Example 1: Oil composition cooling test)
The oil and fat compositions obtained in Examples 1 to 3 and Comparative Examples 1 to 3 were subjected to normal purification (deoxidation / decolorization / deodorization). About the thing which mix | blended 50 mass% of the obtained oil-fat composition and rapeseed oil, respectively, and the obtained oil-fat composition alone, the cooling test (0 degreeC, 5.5 h) of the salad oil specification was done. The results are shown in Table 1.

  From the above results, the oil and fat compositions obtained in Examples 1 to 3 and Comparative Example 3 cleared the salad oil standard cooling test (0 ° C., 5.5 h) when blended with rapeseed oil at 50 mass%. Moreover, the oil and fat composition obtained in Example 3 cleared the cooling test alone (100%). However, when the oil and fat compositions obtained in Comparative Examples 1 and 2 were mixed with rapeseed oil in an amount of 50% by mass, the cooling test could not be cleared, and the liquid properties of the oil and fat compositions obtained in Comparative Examples 1 and 2 were sufficient. It was not satisfactory.

(Test Example 2: Chromaticity of oil composition)
The oil and fat compositions obtained in Examples 1 to 3 and Comparative Example 3 were subjected to normal purification (deacidification / decolorization / deodorization), and the chromaticity was measured using a Robibond colorimeter (manufactured by The Tintometer). . The results are shown in Table 2. The cell size used is 1 inch. In Table 2, R represents red and Y represents yellow.

  From the above results, the oil and fat composition obtained in Comparative Example 3 has a very high chromaticity as compared with the oil and fat compositions obtained in Examples 1 to 3, and other liquid oils based on the entire mixed oil. Even when 50% by mass was blended, it was unbearable to make a product as a salad oil.

(Test Example 3: Flavor test of oil and fat composition)
The oil / fat compositions obtained in Examples 1 to 3 and Comparative Example 3 were subjected to ordinary purification (deoxidation / decolorization / deodorization), and the taste was evaluated by 10 professional panelists. The evaluation was performed by a 5-point method, and 5 points: fresh and very delicious, 4 points: very delicious, 3 points: delicious, 2 points: slightly bad, 1 point: bad. The results are shown in Table 3. In addition, the score in Table 3 is an average score of the score of 10 people.

  From the above results, the oil and fat compositions obtained in Examples 1 to 3 had good flavor and could be used satisfactorily as salad oil. However, the oil and fat composition obtained in Comparative Example 3 had a bad flavor even immediately after purification and was not suitable for use as a salad oil.

(Test Example 4: Empty heating test of oil and fat composition)
The oil and fat compositions obtained in Examples 1 to 3 and Comparative Example 3 were subjected to normal purification (deoxidation / decolorization / deodorization), and then 2 ppm of silicone was added. Example 1 and 2 and Comparative Example 3 were mixed with 50% by mass of the oil / fat composition and rapeseed oil (containing 2 ppm of silicone), Example 3 was the same oil / fat composition, and a round bottom magnet having a diameter of 18 cm. 300 g was collected on a plate and heated by air at 180 ° C. for 5 hours. As a comparison object, an air heating test of rapeseed oil (containing 2 ppm of silicone) was also conducted. After returning to room temperature, the anisidine value, viscosity increase rate (comparison with before air heating) and coloring increase rate (comparison with before air heating) were compared. The results are shown in Table 4.

  From the above results, the oil and fat composition obtained in Examples 1 and 2 and Comparative Example 3 and the oil and fat composition obtained in Example 3 and the oil and fat composition (single) containing 50% by mass of rapeseed oil were salad oil. The heat resistance was better than the rapeseed oil, which is the main component of Especially, it turned out that the oil-fat composition (single) obtained in Example 3 which also cleared the cooling test of salad oil has the heat resistance excellent as salad oil. What mix | blended 50 mass% of the oil-fat composition and rapeseed oil each obtained by the comparative example 3 is coloring rather than what mix | blended 50 mass% of the oil-fat composition and rapeseed oil each obtained in Examples 1-2. The rate of increase was quite inferior.

(Test Example 5: Tempura flavor test of oil and fat composition)
The oil and fat compositions obtained in Examples 1 and 2 and Comparative Example 3 were subjected to normal purification (deoxidation / decolorization / deodorization). 300 g of an oil / fat composition in which 50% by mass of rapeseed oil was blended with the oil / fat compositions of Examples 1 and 2 and Comparative Example 3 on the basis of the whole mixed oil was collected in a round bottom porcelain dish having a diameter of 18 cm. Tempura was made using the following materials at 170 ° C., and 10 professional panelists evaluated the flavor of tempura. In addition, the flavor test of rapeseed oil was also performed as a comparison object. The results are shown in Table 5.
Materials used: 2 shrimp, 2 slices of sea bream Batter composition: 50g egg, 150g water, 100g flour

  From the above results, the oil / fat composition containing 50% by mass of the oil / fat composition obtained in Examples 1 and 2 and rapeseed oil each had good flavor, and the maintenance of the flavor was also superior to the rapeseed oil. However, the oil and fat composition containing 50% by mass of the oil and fat composition and rapeseed oil obtained in Comparative Example 3 had a considerably poor flavor.

It is a process flow figure concerning the manufacturing method of the present invention. It is a conceptual diagram regarding the random transesterification of palm fats and oils. It is a phase diagram which shows the relationship between POP / PPO ratio and melting | fusing point.

Claims (5)

(A) A step of transesterifying the palm-based fats and oils using a lipase having random transesterification ability ;
(B) The step of separating the transesterified oil and fat obtained in the step of transesterification to remove SSS (S means saturated fatty acid, SSS means triglyceride composed of three saturated fatty acids);
The manufacturing method of the high-liquid palm oil which repeats the series of processes consisting of the said process (A) and (B) twice or more in the manufacturing method of the palm oil containing this.   The manufacturing method of Claim 1 which repeats a series of operation which performs a process (B) after the said process (A) 3 times or more. The manufacturing method according to claim 1 or 2 , wherein in the step (B), the fractionation is performed by dry fractionation. A highly liquid palm oil obtained by the production method according to any one of claims 1 to 3 ,
(I) PPP (P means palmitic acid, PPP means tripalmitin composed of three palmitic acids) content is 0.2 mass% or less,
(Ii) P ₂ O (O means oleic acid, P ₂ O means triglyceride composed of two palmitic acids and one oleic acid) content of 16% by mass or less,
(Iii) POP / (POP + PPO) (POP means triglyceride composed of 1 and 3 positions palmitic acid, 2 position oleic acid, PPO 1 and 2 position palmitic acid, 3 position composed of oleic acid The triglyceride and the triglyceride composed of palmitic acid at positions 2 and 3 and oleic acid at position 1)
(Iv) iodine value is 70 or more,
High liquid palm oil. Salad oil obtained by mixing the highly liquid palm oil according to claim 4 alone or with another liquid oil.

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