JPS63191899A - Dewaxing of triglyceride oil - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of the Invention The present invention relates to a method for degumming triglyceride oils.

BACKGROUND OF THE INVENTION Edible oils are triglycerides extracted from animals, seafood or plants. Oils of marine or vegetable origin contain, in addition to triglycerides of fatty acids, extraneous substances such as, for example, free fatty acids, colored bodies, sterol-type compounds and phosphorus-containing compounds. Phosphorus-containing compounds are known as phosphatides, phospholipids or gums. When refining triglyceride oil, it is necessary to remove one or more of these components. In particular, the amount of phospholipids (in terms of phosphorus group ratio) is about 50
It is desirable to reduce the initial concentration from 0 to 3000 ppn+ to less than about 3 ppm. Oils containing more than 1 to 2 ppm phosphorus are unstable in odor and color. Also, the presence of phosphorus compounds above this level will interfere with further processing of the oil, such as hydrogenation of the oil.

It is generally believed that there are two types of phosphatides present in triglycerides: hydratable phosphatides and hydrolyzable phosphatides. Hydrable phosphatides can be easily removed by treatment with water to hydrate it and then remove it, for example by centrifugation. Extraction of triglycerides is often carried out by this initial degumming method, producing an oil that is partially degummed or referred to as industrial degummed oil or degummed oil. This industrial degumming process can reduce the phosphorus content of oils to as low as 20 ppm.

However, even this level of phosphorus content is too high for practical applications.
It is therefore necessary to further purify industrial degummed oils to remove residual phospholipids present in hydrolyzable form.

The conventional industrial method for degumming triglycerides is
The oil is treated with phosphoric acid or citric acid at a temperature of 6'O to 90°C for about 20 minutes to hydrolyze and hydrate the phosphatides, and then the oil is neutralized with caustic soda to remove free fatty acids, phospholipids and soaps. Consists of removing. This neutralization process produces what is called soap stock, which is a combination of free fatty acids and caustic soda. Soap stock and phospholipids are removed by centrifugation. Following this step, the oil is bleached using bleaching clay to remove color bodies and then deodorized by steam treatment to remove odors, aromas and free fatty acids.

Problem to be Solved by the Invention This conventional method has a major drawback in that soap stock is produced. This soap stock is an unwanted waste product that requires further treatment before disposal.

Soap stocks also carry undesirable amounts of contaminant oils.

Despite this major drawback, this method remains one of the most widely used industrial methods for producing triglycerides because the phosphorus content can be suppressed to less than about 3 ppm. .

Many efforts have been made to improve this process, but none have been able to reduce the content to acceptable levels.

The usual approach to solving the above industrial method problem is to
The purpose is to omit the neutralization step by performing the initial degumming step more intensively. For this purpose, for more than an hour,
Treat the oil with phosphoric acid or citric acid at a temperature of about 90-100°C. The gum is then removed by centrifugation and then
The oil is processed by passing it through a bleaching and deodorizing process.

This intensive degumming method is unsatisfactory in that it cannot reduce the phosphorus content to acceptable levels for most triglyceride oils;
The phosphorus content of the oil after the intensive degumming process is approximately 20-50 pρ
It is m. Even after the subsequent bleaching and deodorizing steps, the oil content is, for example, about 15-20 ppm. As mentioned earlier, the phosphorus content is less than 3 ppm, more preferably ipp
It is preferable to suppress it to less than m.

Canadian Patent No. 1.060.041 (August 7, 1979)
(Japan, Unilever Ltd.) discloses a method for degumming triglyceride oils. 65-90
After dispersing the acid or acid anhydride, preferably citric acid, in the oil at a suitable temperature of °C, the oil is dispersed with water and the oil.
The water/acid mixture is maintained at a temperature below 40° C. for a short period of time.

After this, the oil can be subjected to neutralization, bleaching and/or deodorization steps and treated to remove phosphorus, color bodies and free fatty acids. In the case of this initial degumming step, only an acid contacting step carried out at a very high temperature, for example 70° C., is exemplified. Even after washing, bleaching and deodorization, or after undesirable neutralization steps, phosphorus removal is always: 3 p.
It was not at an acceptable level below pm. None of the conditions illustrated have been able to reduce content levels below 1 ppm.

Canadian Patent No. 1.157.883 (November 29, 1983, United Oilseed Product
ts Ltd, ) has Canadian Patent No. 1.060.
An improvement to a method similar to that of No. 041 is disclosed.

In this improved process, the temperature of all steps of acid contact, water contact and centrifugation is above 40°C, preferably between 45°C and 5°C.
It is set within a range of 5°C. Exemplary methods control phosphorus to levels varying between 6 ppm and 1100 ppm, but typically less than 50 ppm.

Means for Solving the Problems According to the present invention, an organic acid or acid anhydride is dispersed in triglyceride oil at a temperature not exceeding about 40°C, and then, while maintaining this temperature, water is added to the kernel oil. It has been found that triglyceride oils can be efficiently and economically degummed by dispersing the gums in the oil and then separating the gum-containing sludge from the oil. This method is effective in reducing phosphorus content to less than about 15 ppm at this stage of purification.

Further surprisingly, the inventors have discovered that the oil product of the degumming process of the present invention, when further subjected to a bleaching step and processed, always yields a refined oil product with a phosphorus content of substantially less than 3 ppm. I found that it can be done.

After bleaching, the phosphorus content is reduced to, for example, less than about 1 ppm, usually less than about 0.5 ppm.

The degumming method of the present invention is performed at lower temperatures than conventional methods, resulting in conditioning of phosphorus compounds in oil.
It is thought that since the compound can be easily adsorbed onto the bleaching clay, it can be completely removed in the subsequent bleaching operation, but the present inventors do not adhere to this idea. Furthermore, once phospholipids in oil are hydrolyzed and hydrated by this method, they are more completely removed than when carried out at higher temperatures due to the reduced oil solubility at the lower temperature conditions of this method. It is considered possible.

Thus, while the process of the present invention, when carried out in conjunction with a bleaching step, can reduce phosphorus content to at least the same level as conventional alkaline refined and bleached oils, the process of the present invention reduces undesirable soap stocks. This result can be achieved without producing oil and without introducing oil into the soap stock. Additionally, this result can be achieved without the need to maintain high temperatures during the acid contacting step. Additionally, the oil product obtained by the process of the invention leaves the free fatty acids in a relatively stable form so that they can be removed and recovered in a subsequent deodorization and fatty acid stripping step consisting of steam distillation.

That is, the present invention generally comprises (a) dispersing an organic acid or acid anhydride in a triglyceride oil at a temperature of about 40° C. or less;
) Next, while maintaining the temperature at about 40°C or less,
dispersing water in the kernel oil and then (c) separating the gum-containing sludge from the kernel oil to produce an oil product substantially reduced in phosphorus-containing compounds at about 40°C. The present invention provides a method for degumming liquid triglyceride oil.

WORKING The triglyceride oils normally used as feedstock oils in this process include press extraction or solvent extraction of properly produced oil seeds, or solvent extraction of residual oil from the press operation.
Includes edible oils of vegetable and aquatic sources obtained by any known extraction method. The oil may be wholly or partly produced by pressing or solvent extraction of marine species. Such feedstock oils may be in their crude form, but are typically obtained by industrial extraction of these oils and are partially degummed (industrial degumming) in which hydratable phospholipids have been substantially removed. is used. Raw material oil is approximately 4
It is substantially liquid at the temperatures applied in the process of the invention, which are below 0°C.

To achieve the above advantages of the process of the invention, the step of contacting the oil with the organic acid or acid anhydride is carried out at a temperature of about 40°C or less. At temperatures above 40°C, the phosphorus removal rate achieved by the method decreases considerably. Generally, the lower limit temperature in these steps is determined by the physical properties of the raw material oil.

The feedstock is liquid at the process temperatures of the present invention. For economic reasons, the preferred temperature of the process is in the range of about 20-25°C. In this room temperature range, the feedstock does not need to be heated or cooled throughout the process.

Certain triglyceride oils, such as corn oil and sunflower oil, precipitate undesirable waxes upon cooling. These waxes precipitate and give the oil a cloudy appearance. Also, waxes deteriorate due to high temperature processing, which adversely affects the stability of the final product.

Typically, such oils are cooled to crystallize the waxes and then cold filtered to remove the waxes.

According to the method of the present invention, triglyceride oils containing waxes can be simultaneously dewaxed and degummed by maintaining the temperature in the range of about 0-10° C. throughout the gumming process. In this way, the organic acid and then the water are dispersed in the oil and the sludge is separated from the oil at a temperature of about 0-10°C. The sludge removed from the oil contains a large portion of phosphorus-containing gums and waxes.

In the first step of the invention, ie, the phosphorus contacting step, the acid-oil mixture is preferably maintained with stirring for a period sufficient to hydrolyze the majority of the hydrolyzable phospholipid. The time required for this step varies with each oil and application temperature, but is usually less than about 1 hour, preferably 10
~20 minutes.

The organic acid or acid anhydride used in the method is optimally citric acid or maleic anhydride and is preferably of food grade quality. Other acids comparable to citric acid and maleic anhydride and suitable for use in the present process include maleic acid, lactic acid, oxalic acid and acetic anhydride. Preferably, the acid is added as an aqueous solution containing up to the saturation point. A 50% by weight aqueous solution of the acid is preferred.

The amount of acid to be added to the oil will vary depending on the type of oil being treated, the amount and type of impurities in the oil, and other processing conditions. As a representative example, the process of the present invention may include approximately 1.000 to 10.000 g of oil, calculated on a dry acid basis.
ppm (0.1 to 1.0% by weight) is sufficient.

Once the oil is treated with acid to hydrolyze the phospholipids, water is dispersed in the oil while maintaining the temperature at about 40° C. or less. The amount of water required in this step varies depending on the amount of phospholipid in the oil, but usually an amount of 0.1 to 3% by weight of the oil is sufficient.

In the second step of the method, the oil-acid-water mixture is preferably maintained with stirring for a sufficient period of time to hydrate most of the phospholipid. Similarly, this time will vary with the type of oil and application temperature, but is typically less than about 1 hour, preferably about 20-30 minutes.

Once hydrated, phospholipids become oil-insoluble;
Precipitates from the oil in the form of an aqueous sludge. This sludge is
It is separated from the oil, preferably by centrifugation in a well-known manner. For practical reasons, centrifugation is approximately 35
Preferably, the reaction is carried out at a temperature below .degree. After separation, the oil product is typically found to have a phosphorus content of less than about 15 ppm.

The method of the invention can be carried out either batchwise or continuously.

The oil product obtained by this process is in a form suitable for further processing by known methods of bleaching, deodorization and free fatty acid IJpping. As previously explained, after subsequent bleaching, the oil products obtained from the process of the invention have very low levels of residual phosphorus, to exemplify:
less than lppm.

If desired, the oil product can be neutralized by known neutralization methods, but it is preferable to omit this step to avoid the formation of undesirable soap stocks.

The method will now be illustrated by the following examples which illustrate the operability and preferred conditions of the method, but the scope of the invention is in no way limited by these examples.

EXAMPLES Example ■ This example illustrates the effect of temperature on the method of the present invention.

At the temperatures given in Table 1, the following initial properties, namely color (LOV
IBONXD 25rnm cell >25'Y+ 3.5
Industrially degummed soybean oil with 0.27 wt% free fatty acids as R, oleic acid and 129 ppm phosphorus content was contacted with a 50 wt% aqueous solution of citric acid giving a dry acid group content of 5000 ppm.

(LOVIBOND is The Tintometer Limmeter, Salisbury, UK, for a visual colorimeter with a generally accepted colorimetric scale.
d trademark). The above soybean oil and citric acid were vigorously stirred for 15 minutes. Then, 1.0% by weight of water was added to the soybean oil while maintaining the same temperature as in the acid contacting step. The oil mixture was stirred for an additional 30 minutes. The gum-containing sludge was removed by filtration. Table 1 shows the analysis results of the degummed oil.

Thereafter, the degummed oil was bleached using bleaching clay and then deodorized according to the following procedure.

Decolorization (adding chemicals at room temperature) Addition of phosphoric acid Added as 85% aqueous solution 300 ppm
(As dry matter) Addition of citric acid 300 ppm added as a 50% aqueous solution
(As dry matter) Addition of bleaching clay 2.0% by weight Processing conditions 110°C, 10 minutes, atmospheric pressure Removal of clay Filtration and deodorizing temperature 250°C Pressure 0.6mΩHg Time 60 minutes Steam spray 2.4% by weight/hour Decolorization and The deodorization analysis results are shown in Table 1.

The results in Table 1 show that the phosphorus content of soybean oil can be significantly reduced by the degumming process of the present invention. From the initial removal of the sludge, even after bleaching the degummed oil, an oil product is obtained with a higher than desired phosphorus content, but with a very low phosphorus content. However, the temperature of the initial degumming step was below about 40°C. The best results with respect to phosphorus removal were obtained when the degumming step was carried out at a temperature below 35°C.

Example ■ Industrially produced solvent extracted rapeseed oil (300 ppm) containing 1.078 ppm phosphorus and 1.35 wt.
g) was heated to 35° C. with gentle stirring. This is supplemented with a 50% aqueous solution of citric acid to give a concentration of 2.500 ppm on a dry acid basis, or 1.500 ppm of rapeseed oil.
Powdered maleic anhydride was added at level. The oil and acid mixture was stirred vigorously while maintaining a temperature of 35°C. Next, 3.0% by weight of water was added and an additional 2.0% of water was added at the same temperature.
The mixture was stirred for 0 minutes. The mixture was then filtered to remove the gum-containing sludge. Oil products were analyzed for phosphorus and free fatty acid content.

For comparative purposes, the same rapeseed oil was degummed using only water (3.0% by weight) while stirring for 30 minutes at 60°C. Table 2 shows the analysis results of the three types of filtrate.

EXAMPLE ■ To investigate the effect of scaling up the method of the invention, the procedure of Experiments 11 and 12 was repeated using 2.700 g and 3.000 g of the same oil. The treatment conditions and results are shown in Table 3. After degumming, the oil product was decolorized using bleaching clay with addition of acid and then steam refined. The conditions for these two steps were as follows.

Addition of decolorizing phosphoric acid 500 ppm added to oil as 85% aqueous solution at 30°C Addition of citric acid 50 (lppm) added to oil as 50% aqueous solution at 30°C Addition of bleaching clay 30% by weight added at 90°C Processing conditions
110°C, 15 minutes, atmospheric pressure, stirring Steam purification temperature: 225°C Time: 60 minutes Example ■ In order to examine the reproducibility of the method of the present invention, pressed oil and extracted oil that had been industrially degummed in advance by a conventional method were used. The mixed feedstock was processed. In each experiment, 40Y+3, OR+0.5
Initial color of B (LQVIB [lN015mm cell), 23
3000 g of oil with an initial phosphorus content of 0 ppm and an initial free fatty acid content of 0.88%, on a dry basis
)ffl of citric acid was brought into contact with an aqueous solution of citric acid.

The oil and acid were stirred vigorously for 30 minutes. Degumming was more difficult because the oil was partially degummed. For this reason, the amount of citric acid added and the stirring time were increased and extended over those used in the previous example. Thereafter, 2.0% by weight of water was added and the mixture was stirred for an additional 60 minutes.

The gum-containing sludge was removed by filtration. The analysis results of the degummed oil are shown in Table 4.

The degummed oil was then bleached using acid addition and bleaching clay and then deodorized using the following procedure.

Decolorization (degummed oil 2.500 g) Addition of phosphoric acid Added to oil as 85% aqueous solution at 30 °C 500 ppm Addition of citric acid Added to oil as 50% aqueous solution at 30 °C Addition of bleaching clay Added at 105 °C 3.0 Weight% treatment conditions 110-112°C, 15 minutes atmospheric pressure, high speed stirring Clay removal Vacuum filtration U (decolorizing oil 1.200 g) Equipment cAMPRO stainless steel deodorizer (cAMPRO is manufactured by Cambrian Processes, Mississauga, Ontario, Canada) cambrian Processes Li
Temperature: 225°C Pressure: 0.5 to 1. Q mm Hg Time 60 minutes Steam spray 3% by weight of oil Cooling The results of the vacuum analysis are shown in Table 4.

From this result, the degumming method lowers the phosphorus level by approximately 10
It can be seen that the content was reduced to ~24 ppm. The reproducibility of phosphorus removal, color, free fatty acid removal and aroma was excellent.

Example V To illustrate the application of this method to an industrial installation, a 7001 baffled reactor equipped with a turbine agitator was
Industrially produced, non-degummed canola (canola)
) oil (mixture of pre-squeezed and extracted oils) 4501 was charged. The initial properties of this oil are 5Y+3, 3R (LOVI
BON025mm cell), free fatty acid content (as oleic acid) of 0.81%, and adjacent content of 541 ppm
Met. The oil was brought into contact with a 50% aqueous solution of citric acid resulting in citric acid of 2.5001] pm (on a dry acid basis). The temperature for this step was 35°C. 28Qrp
The mixture was stirred for 10 minutes at m. After this, 3% water by weight was added to the mixture and the mixture was heated at 28Q rpm for another 20 minutes.
It was stirred with The purified aqueous sludge was removed by centrifugation under the following conditions.

Centrifugal separator Westfalia Niss Aar (WBSTFAL)
IASA) -7-01576°, i.e. 69 disks (
Automatic discharge centrifuge with top diameter: 5.4 cm, bottom diameter: 16.2 cm). Sixty-five of the discs were liquid-liquid-plane separation discs, and four were clarification discs located at the 1st, 23rd, 46th, and 69th positions, respectively. (W
ESTFALIA is manufactured by Centrico Inc., North Vale, New Jersey, USA.
).

Angle: conical half angle 35° Bowl diameter 24.9cm Bowl speed 8.40Orpm The analysis results of the degummed oil are shown in Table 5.

Then in the reactor for 1 hour at 60-70°C under -27″Hg.
The degummed oil was dried. The degummed oil (recovered 1,5001) was pumped into a 2600 f jacketed reactor and 300β of this oil
PEMBINA VEGA) mixed with clay bleaching earth,
A slurry of 3% based on total oil was obtained. (PEMBINA
VBGA Canada, Pemb, Winpeg, Manitoba
ina MountainClays Incorporated
rated trademark). While mixing in the remaining oil,
Phosphoric acid and citric acid at 500 ppm each were added (in solution). The oil/acid mixture was heated to 100° C. under vacuum while stirring. The clay slurry was then added to this mixture, again at a temperature of 100°C. Total mixture to 110
Heat to ~115° C. and maintain at −27” Hg for 15 minutes. Cool the bleach oil to 60° using a heat exchanger and then
Filtered with a filter press. The analytical results of decolorization are shown in Table 5.

Thereafter, the bleach oil was decolorized using a CAMPRO pilot deodorizer under the following conditions.

Oil flow rate: 700-750 Ibs/hr Steam spray: 211 bs/hr Vacuum: 3 mmHg Temperature: 257-260°C The results are shown in Table 5.

Example ■ The following example illustrates the simultaneous degumming and dewaxing of triglyceride oils containing waxes.

The following initial characteristics, namely color power 30Y+1.5R (LOVI
BON025mm cell), 0.98% free fatty acids (as oleic acid) and 114 ppm phosphorus content.
Industrially produced degummed sunflower oil was degummed at two temperatures: 23°C and 8°C. For low temperature degumming, the oil was held at 8° C. for 42 hours prior to processing to promote wax crystallization. For degumming at both temperatures, the oil was contacted with a 50% aqueous solution of citric acid giving 2.000 ppm citric acid on a dry acid basis, followed by stirring for 15 minutes. Water (1%) was then added to the oil and the oil was mixed for an additional 30 minutes before being filtered. Water addition process and filtration process are 23
℃ and 8℃ temperatures.

The results are shown in Table 6.

Next, phosphoric acid and citric acid (500 ppm each) were added at room temperature.
After the addition of 3% by weight bleaching clay at 90° C., the degummed oil was decolorized. Bleaching treatment is carried out under reduced pressure at 110
-115°C for 15 minutes. The results are shown in Table 6.

After this, the bleached oil was deodorized for 60 minutes at 225°C. The steam spray rate in this step was approximately 3%/hour.

Deodorize to check wax removal rate.

A cold test was conducted on oil. The results are shown in Table 6.

As can be understood from these results, the method of the present invention
When carried out at 8° C., it produced an oil product with significantly reduced wax content and phosphorus content.

Claims (25)

[Claims] (1) (a) dispersing an organic acid or acid anhydride in a substantially liquid triglyceride oil at a temperature of 40°C, (b) maintaining the temperature below 40°C; (c) separating the gum-containing sludge from said oil to produce an oil product substantially reduced in phosphorus-containing compounds. A method for degumming liquid triglyceride oil. (2) The above process (
A method according to claim 1, characterized in that a) and (b) are carried out. (3) The above step (a) is performed at a temperature of 0°C or higher and lower than 40°C.
2. A method according to claim 2, characterized in that the steps (a) and (b) are carried out. (4) The oil to be treated contains a negligible amount of waxes, and the temperature of steps (a) and (b) is less than about 35°C. Method. (5) The oil to be treated contains waxes, and the above process (
Claim 1, characterized in that the waxes are removed together with the sludge in the separation step (c) by setting the temperatures in a) and (b) in a range of about 0 to 10°C. the method of. (6) The method according to claim 1, wherein the organic acid or acid anhydride is citric acid or maleic anhydride. (7) The method according to claim 1, wherein the acid is food grade citric acid. (8) Citric acid is added to the above oil as an aqueous solution, and the citric acid is contained in an amount of about 1,000 to 10,000 ppm in terms of dry acid. The method described in scope item 7. (9) The method according to claim 8, characterized in that citric acid is added to the oil as an aqueous solution, and the citric acid is contained in the aqueous solution at a concentration up to a saturation concentration. (10) The method according to claim 8, characterized in that citric acid is added to the oil as a 50% aqueous solution. (11) The amount of water added in the above step (b) is 0% of the above oil.
．． 2. A method according to claim 1, characterized in that the amount is in the range 1-3% by weight. (12) The amount of water added in the above step (b) is 0% of the above oil.
．． 10. A method according to claim 9, characterized in that the amount is in the range 1-3% by weight. (13) The amount of water added in the above step (b) is 1 of the above oil.
．． 10. A method according to claim 9, characterized in that the amount is in the range 5-2.5% by weight. (14) In step (a), the mixture of oil and citric acid is maintained with stirring for a sufficient time to hydrolyze the hydrolyzable phosphorus-containing compound. The method described in. (15) The method according to claim 1, wherein in step (a), the mixture of oil and citric acid is maintained for less than 1 hour while stirring. (16) The method according to claim 13, wherein in step (a), the mixture of oil and citric acid is maintained for a period of 10 to 20 minutes while stirring. (17) In step (b), the mixture of oil, citric acid, and water is maintained with stirring for a time sufficient to hydrate most of the phosphorus-containing compound. The method described in Section 1. (18) The method according to claim 1, wherein in step (b), the mixture of oil, citric acid, and water is maintained while stirring for no more than 1 hour. (19) The method according to claim 16, wherein in step (b), the mixture of oil, citric acid, and water is maintained for a period of 20 to 30 minutes while stirring. (20) The method according to claim 1, characterized in that the separation step (c) is carried out by centrifugation to remove the gum-containing sludge. (21) The method according to claim 20, characterized in that the centrifugation is carried out at a temperature of 35° C. or lower. (22) The triglyceride oil raw material is from a vegetable source or a marine product source, and the triglyceride oil raw material has been industrially degummed in advance. Method. (23) Claim 21, characterized in that the triglyceride oil base oil is from a vegetable source or a marine product source, and the triglyceride oil base oil has been industrially degummed in advance. the method of. (24) In the oil degumming method described above, which comprises degumming triglyceride oil that is substantially liquid at 40°C and then decolorizing it using bleaching clay, (a) substantially liquid triglyceride oil at 40°C or lower is decolored; An organic acid or acid anhydride is dispersed in triglyceride oil at a temperature below 40°C, and (b
) dispersing water in the above oil while maintaining a temperature below 40° C.; and (c) separating the gum-containing sludge from the above oil to obtain an oil with substantially reduced phosphorus-containing compounds. producing a product at 40° C., such that when the oil product is subsequently bleached, a bleached oil product having a phosphorus content of less than about 1 ppm is obtained. A method for degumming liquid toglyceride oil. (25) (a) dispersing an organic acid or acid anhydride in a triglyceride oil that is substantially liquid at 40°C at a temperature below 40°C; (b) dispersing the above oil while maintaining a temperature below 40°C; (c) separating the gum-containing sludge from the oil described above to produce an oil product having substantially reduced phosphorus-containing compounds, and then (d) dispersing water in step (c) above. A substantially liquid solution at 40° C. formed by contacting the oil product with a bleaching clay and then separating the clay from the oil to produce a decolorized bleach product having a phosphorus content of less than about 1 ppm. A method of degumming triglyceride oils.