KR102520377B1 - Method for preparing triglyceride with high purity by using short path distillation or wet fractionation - Google Patents

Abstract

The present invention relates to a method for producing triglyceride, and more particularly, in producing triglyceride through an enzymatic esterification reaction in which an acyl group of a triacylglyceride is exchanged for another acyl group, the reaction product is subjected to short path distillation , SPD) or wet fractionation, thereby producing high-purity triglycerides in high yield.

Description

Method for preparing triglyceride with high purity by using short path distillation or wet fractionation {Method for preparing triglyceride with high purity by using short path distillation or wet fractionation}

The present invention relates to a method for producing triglyceride, and more particularly, in producing triglyceride through an enzymatic esterification reaction in which an acyl group of a triacylglyceride is exchanged for another acyl group, the reaction product is subjected to short path distillation , SPD) or wet fractionation, thereby producing high-purity triglycerides in high yield.

Triacylglyceride fats and oils are widely used in the food industry, among which 1,3-dioleoyl-2-palmitoyl glyceride (OPO) is As an important component of , a lot of research has been conducted nutritionally.

Fat compositions containing the major fatty acids that make up human milk fat are found in many oils and fats of plant origin, but almost all glycerides of plant origin do not have saturated fatty acids at the 2-position. In contrast, in human milk fat, a significant amount of the saturated fatty acid palmitic acid occupies the 2-position of the glycerides.

Recently, as people's interest in infant health increases, the demand for foods similar to breast milk and ingredients is increasing.

Innis (Adv. Nutr., 2:275-283, 2011) describes the structural role of triacylglycerols in infant diet.

However, normal milk powder is a mixture of powdered milk and vegetable oil, and hardly contains palmitic acid at the 2-position when the oil component of powdered milk is analyzed.

Accordingly, application of high-quality breast milk fat substitute paper for adding 1,3-dioleoyl-2-palmitoyl glyceride (OPO) containing palmitic acid at the 2-position, which is similar in composition to breast milk fat, to powdered milk this is increasing

OPO is a type of USU (Unsaturated-Saturated-Unsaturated) triglyceride, and Mohamad, et al (Lipase-catalyzed interesterification reactions for human milk fat substitutes production, 2013, 115, 270-285) reported that when using lipase, It shows that studies on synthesizing 1,3-dioleoyl-2-palmitoyl glyceride by substituting the 1,3-position of acyl glyceride have been mainly conducted. The provision of a glyceride backbone containing a saturated fatty acid at the 2-position of the triacylglyceride fat by the 1,3-position-specific reaction nature of the triacylglyceride of lipase is 1,3-dioleoyl-2-palmy It is important in the synthesis of toyl glycerides (OPO).

However, there is a problem in that the purity of 1,3-dioleoyl-2-palmitoyl glyceride (OPO) is low to commercially use the product of such an enzymatic esterification reaction.

Therefore, in preparing 1,3-dioleoyl-2-palmitoyl glyceride (OPO) using an enzymatic esterification reaction, development of a new method capable of maintaining excellent overall yield while increasing the purity of the target product is required. being requested

The present invention is a triglyceride (eg, 1,3-dioleo) through an enzymatic esterification reaction in which an acyl group of a triacylglyceride (eg, tripalmitoylglyceride (PPP)) is exchanged for another acyl group (eg, an oleyl group). In preparing 1-2-palmitoyl glyceride (OPO), it is a technical task to provide a method capable of maintaining an excellent overall yield while increasing the purity of the target product.

According to one aspect of the present invention, (1) an enzymatic esterification reaction is performed on a reactant mixture including triacylglycerides and a fatty acid having an acyl group different from the acyl group in the triacylglycerides to reduce the acyl groups of the triacylglycerides. exchanging the acyl group of the fatty acid; and (2) distilling the resultant mixture of the enzymatic esterification reaction obtained in step (1), wherein the distillation is carried out under conditions of a pressure of 0.1 mbar or less and 200 A process for producing triglycerides is provided comprising distillation in a short path still under temperature conditions of -240°C.

According to another aspect of the present invention, (1) an enzymatic esterification reaction is performed on a reactant mixture including triacylglycerides and a fatty acid having an acyl group different from the acyl group in the triacylglycerides, so that the acyl groups of the triacylglycerides are exchanging the acyl group of the fatty acid; and (2) wet-fractionating the resultant mixture of the enzymatic esterification reaction obtained in step (1), wherein the wet fractionation is performed by mixing the mixture resulting from the reaction of step (1) with an organic solvent in a ratio of 1:10. Or, there is provided a method for producing triglyceride comprising mixing and dissolving at a volume ratio (reaction resultant mixture: organic solvent) greater than or equal to, and then allowing the solution to stand for 30 minutes or more under a temperature condition of -5°C or lower.

According to another aspect of the present invention, (1) an enzymatic esterification reaction is performed on a reactant mixture including triacylglycerides and a fatty acid having an acyl group different from the acyl group in the triacylglycerides to obtain acyl groups of the triacylglycerides. exchanging a group for an acyl group of the fatty acid; (2) distilling the resultant mixture of the enzymatic esterification reaction obtained in step (1); and (3) wet-fractionating the resultant mixture of the enzymatic esterification reaction obtained in step (2), wherein the distillation is carried out under conditions of a pressure of 0.1 mbar or less and Including distillation in a short path still under a temperature condition of 200 to 240 ° C., wherein the wet fractionation is performed by distilling the distillation residue from step (2) with an organic solvent at a volume ratio of 1:10 or greater (reaction resultant mixture: organic A method for producing triglyceride comprising mixing and dissolving in a solvent) and then allowing the solution to stand for 30 minutes or more under a temperature condition of -5°C or lower is provided.

According to the present invention, in preparing a triglyceride (eg, 1,3-dioleoyl-2-palmitoyl glyceride (OPO)) in which an acyl group of a triacylglyceride is exchanged with another acyl group through an enzymatic transesterification reaction, the target product It is possible to maintain excellent overall yield while increasing the purity of .

Hereinafter, the present invention will be described in detail.

In the present invention, triacylglycerides used as reactants of the enzymatic esterification reaction may be edible fats and oils.

As the edible oil, any vegetable or animal fat, liquid or solid, hydrogenated oil or transesterified oil of the fat, liquid oil obtained by fractionating the fat, solid fat, etc. can be used as long as it is suitable for food.

Specific examples of the vegetable oil include those selected from corn oil, rapeseed oil, soybean oil, cottonseed oil, palm oil, palm oil, rice bran oil, sesame oil, cacao fat, olive oil, and combinations thereof, and specific examples of the animal oil include fish oil, and those selected from pork fat, tallow (bovine fat), chicken fat, and combinations thereof. These edible fats and oils can be used alone or in combination of two or more.

In one embodiment, the triacylglyceride may be fractionated palm oil obtained by fractionation of palm oil among vegetable oils.

In one embodiment, the acyl groups present in the triacylglyceride are saturated or unsaturated independently having 4 to 24 carbon atoms, more specifically 12 to 22 carbon atoms, and even more specifically 14 to 20 carbon atoms. It may be selected from linear aliphatic acyl groups of For example, the acyl group present in the triacylglyceride may be independently selected from a palmitoyl group, a stearoyl group, an oleoyl group, and a linoleoyl group, and preferably may be a palmitoyl group, but is not limited thereto.

In one embodiment, at least one of the acyl groups present in the triacylglyceride is a palmitoyl group, preferably two, more preferably all three palmitoyl groups. That is, in the most preferred embodiment, the starting material triacylglyceride is tripalmitoylglyceride (PPP).

In the present invention, the fatty acid used as a reactant of the enzymatic esterification reaction has an acyl group different from the acyl group in the triacylglyceride.

In one embodiment, the fatty acid is selected from saturated or unsaturated straight-chain fatty acids having 4 to 24 carbon atoms, more specifically 12 to 22 carbon atoms, and even more specifically 14 to 20 carbon atoms. More than one may be used. More specifically, the fatty acid may be selected from the group consisting of palmitic acid, stearic acid, oleic acid, linoleic acid, and combinations thereof, and may preferably be oleic acid, but is not limited thereto.

In the triglyceride production method of the present invention, the mixing ratio of triacylglyceride to fatty acid included in the reactant mixture of the enzymatic esterification reaction may be 1:1.1 or more, 1:1.2 or more, or 1:1.3 or more in volume ratio, It may also be 1:2 or less, 1:1.95 or less, or 1:1.9 or less.

In the present invention, the reaction temperature of the enzymatic esterification reaction may be determined according to the type of enzyme used, and specifically, may be 40 ° C or higher, 45 ° C or higher, 50 ° C or higher, 55 ° C or higher, or 60 ° C or higher, and It may be 85°C or less, 80°C or less, 75°C or less, 70°C or less, or 65°C or less, but is not limited thereto. In order to optimize the effect of the reaction and the efficiency of the process, the reaction temperature may preferably be 40°C to 80°C, more preferably 45°C to 70°C.

The reaction time of the enzymatic esterification reaction in the present invention may be, for example, 0.5 hours or more, 1 hour or more, 2 hours or more, 3 hours or more, or 4 hours or more, and also 12 hours or less, 10 hours or less, 8 hours or less, or It may be 6 hours or less, but is not limited thereto.

In the present invention, known enzymes may be used as enzymes for the enzymatic esterification reaction without particular limitation. Specifically, Candida Antarctica B , Thermomyces lanuginose , Rhizomucour miehei , Rhizopus delemar , Mucormiehei , Alkaligenes ( Alcaligenes sp. ), Aspergillus niger ( Aspergillus niger ), Candida cylindraces ( Candida cylindraces ), Bucolderia Cepacia ( Burkholderia cepacia ), Candidum ( Geotricum candidum ), and a microorganism selected from the group consisting of combinations thereof An esterification enzyme derived from can be used, but is not limited thereto.

In one embodiment, 100 parts by weight to 3000 parts by weight, or 100 parts by weight to 2000 parts by weight, or 100 parts by weight to 1000 parts by weight of the reactant mixture per 1 part by weight of the enzyme may be continuously treated without replacing the enzyme, and the activity of the enzyme As long as this is maintained, more quantities can continue to be processed. For example, if the enzyme activity is appropriate, 500 parts by weight or more, 1000 parts by weight or more, 2000 parts by weight or more, or 3000 parts by weight or more of the reactant mixture per 1 part by weight of the enzyme can be continuously treated without replacement of the enzyme, and there are no special restrictions on the upper limit. No, even, 10000 parts by weight or more can be treated. According to a preferred embodiment, the treatment amount of the reactant mixture per 1 part by weight of the enzyme may be 1000 parts by weight to 3000 parts by weight.

In one embodiment, the enzymatic transesterification reaction can be carried out continuously. That is, while continuously introducing a reactant mixture containing triacylglycerides as a starting material and a fatty acid having an acyl group different from the acyl group in the triacylglyceride into a continuous reactor in which an enzyme exists at a constant flow rate using a metering pump, the enzymatic reaction is performed. Enzymatic transesterification can be carried out in such a way that an esterification reaction is performed, and the product after the reaction exits the reactor and is collected in a tank. Here , the flow rate of the reaction mixture may have an SV of 0.05 to 2.0, more specifically 0.1 to 1.5, and more specifically 0.2 to 1.0, but is not necessarily limited thereto.

In one embodiment, the triglyceride prepared according to the above method may be dioleoyl monopalmitoyl glyceride, and more specifically, 1,3-dioleoyl-2-palmitoyl glyceride (OPO).

The method for producing triglyceride according to the first aspect of the present invention includes the step of distilling the mixture resulting from the enzymatic esterification reaction, wherein the distillation is performed to distill the mixture resulting from the reaction of step (1) at 0.1 mbar or less. It is characterized in that it comprises distilling in a short path still under pressure conditions and temperature conditions of 200 to 240 ° C.

The distillation of the enzymatic esterification reaction product is for removing by-products generated after the enzymatic esterification reaction and fatty acids remaining in the reaction product, which is a short path distillator, more specifically, an internal condenser. type) It is carried out under pressure conditions of 0.1 mbar or less and temperature conditions of 200 ~ 240 ℃ in a short path still. In the case of the short-path distillation, if the pressure condition exceeds 0.1 mbar or the temperature condition is less than 200° C., the purity of the target product may be insufficiently improved. In addition, when the temperature condition during the short path distillation exceeds 240° C., the target material may be rather decomposed due to the high temperature.

More specifically, in the case of the short-path distillation, the pressure condition may be 0.09 mbar or less, 0.08 mbar or less, or 0.07 mbar or less. The lower limit of the pressure condition is not particularly limited, and may be, for example, 0.01 mbar or more, 0.03 mbar or more, or 0.05 mbar or more, but is not limited thereto.

More specifically, in the case of the short path distillation, the temperature condition may be 205°C or higher, 210°C or higher, or 215°C or higher, and may also be 235°C or lower, 230°C or lower, or 225°C or lower.

In one embodiment, the feeding rate of the enzymatic esterification reaction product during the short-path distillation may be 20 to 40 g / h, more specifically 20 to 35 g / h, 25 to 35 g / h or 30 to 35 g / h can be

In one embodiment, the rotational speed of the distiller roller during the short path distillation may be 300 to 500 rpm, and more specifically, 300 to 480 rpm, 350 to 480 rpm, or 350 to 450 rpm.

In one embodiment, the cooling temperature of the distillation effluent during the short path distillation may be 10 to 30 °C, more specifically 15 to 25 °C, 18 to 25 °C, or 18 to 22 °C.

The product purified by the short-path distillation according to the first aspect of the present invention may be a triglyceride composition having a monoacylglyceride and diacylglyceride content of 20% by weight or less, and more specifically, the monoacylglyceride and diacylglyceride The content may be 18 wt% or less, 15 wt% or less, or 10 wt% or less.

According to the first aspect of the present invention, the product purified by the short-path distillation may be a triglyceride composition having a free fatty acid content of 4% by weight or less, and more specifically, a free fatty acid content of 3% by weight or less, 2% by weight or less than or equal to 1.5% by weight.

According to the first aspect of the present invention, the product purified by the short-path distillation is a neutral lipid (C52) having a total carbon number of 52 in the neutral lipid (eg, C18-C16-C18, C16-C18-C18, etc. For example, the content of SPS, SSP, OPO, OOP, LPL, LLP, OPL, etc. (where P = palmitoyl group, S = stearoyl group, O = oleoyl group, L = linoleoyl group) is 49% by weight or more, and more specifically, the C52 content may be 50% by weight or more, 51% by weight or more, or 52% by weight or more. The upper limit of the C52 content is not particularly limited, and may be, for example, 80% by weight or less, 70% by weight or less, or 60% by weight or less.

The method for producing triglyceride according to the second aspect of the present invention includes the step of wet fractionating the resulting mixture of the enzymatic esterification reaction, wherein the wet fractionation is carried out by mixing the resulting mixture with an organic solvent in a ratio of 1:10 or more. After mixing and dissolving in a volume ratio (reaction result mixture: organic solvent), the solution is characterized by including standing for 30 minutes or more under a temperature condition of -5 ° C or less.

The wet fractionation of the enzymatic esterification reaction product is for separating only a specific neutral lipid of interest from the resulting mixture of the enzymatic esterification reaction, wherein the reaction resulting mixture is mixed with an organic solvent at a volume ratio of 1:10 or greater. After that, it is allowed to stand for 30 minutes or more under temperature conditions of -5 ° C or less. During wet fractionation, if the mixing ratio of the reaction mixture to the organic solvent is less than 1:10 by volume, the purification yield may be low and the purity of the target product may be insufficiently improved. In addition, when the temperature condition during wet fractionation exceeds -5 ° C, improvement in purity of the target material may be insufficient. In addition, if the wet fractionation time is less than 30 minutes, the purification yield may be low, and the purity of the target product may be insufficiently improved.

More specifically, in the wet fractionation, the mixing ratio of the reaction mixture to the organic solvent may be 1:12 or more, 1:14 or more, or 1:16 or more in terms of volume ratio. In addition, there is no particular limitation on the upper limit of the mixing volume ratio of the reaction mixture to the organic solvent during wet fractionation, and may be, for example, 1:30 or less, 1:25 or less, or 1:20 or less in terms of volume ratio. If the amount of the organic solvent used is excessively greater than the above level, subsequent concentration may become difficult.

More specifically, during the wet fractionation, the temperature conditions may be -10 °C or less, -12 °C or less, -15 °C or less, or -18 °C or less. In addition, there is no particular limitation on the lower limit of the temperature condition during wet fractionation, and may be, for example, -30 ° C or higher, -28 ° C or higher, -26 ° C or higher, or -25 ° C or higher. If the temperature during wet fractionation is too low than the above level, process efficiency may be lowered.

More specifically, the wet fractionation time may be 40 minutes or more, 50 minutes or more, or 60 minutes or more. In addition, the upper limit of the wet fractionation time is not particularly limited, and may be, for example, 180 minutes or less, 160 minutes or less, 140 minutes or less, or 120 minutes or less. Process efficiency may be reduced if the wet fractionation time is excessively longer than the above level.

As the organic solvent for the wet fractionation, acetone, hexane, isopropyl alcohol, methanol, or a combination thereof may be used, preferably acetone.

According to the second aspect of the present invention, the product purified by the wet fractionation may be a triglyceride composition in which the content of neutral lipids (C52) having a total carbon number of 52 in the neutral lipid is 63% by weight or more, and more specifically, the C52 The content may be 64% or more, 65% or more, or 66% or more. The upper limit of the C52 content is not particularly limited, and may be, for example, 85% by weight or less, 80% by weight or less, or 75% by weight or less.

According to the second aspect of the present invention, the product purified by the wet fractionation may be a triglyceride composition having a neutral lipid content of 43% by weight or more in the form of unsaturated-saturated-unsaturated (USU). More specifically, the USU content is 44 wt% or more, 45 wt% or more or 46 wt% or more. The upper limit of the USU content is not particularly limited, and may be, for example, 70% by weight or less, 65% by weight or less, or 60% by weight or less.

In the present invention, the above-described short-path distillation step and wet fractionation step may be performed independently or in combination in this order.

Therefore, according to the third aspect of the present invention, (1) an enzymatic esterification reaction is performed on a reactant mixture comprising triacylglycerides and a fatty acid having an acyl group different from the acyl group in the triacylglycerides to obtain the triacylglycerides exchanging the acyl group of the acyl group of the fatty acid; (2) distilling the resultant mixture of the enzymatic esterification reaction obtained in step (1); and (3) wet-fractionating the resultant mixture of the enzymatic esterification reaction obtained in step (2), wherein the distillation is carried out under conditions of a pressure of 0.1 mbar or less and Including distillation in a short path still under a temperature condition of 200 to 240 ° C., wherein the wet fractionation is performed by distilling the distillation residue from step (2) with an organic solvent at a volume ratio of 1:10 or greater (reaction resultant mixture: organic A method for producing triglyceride comprising mixing and dissolving in a solvent) and then allowing the solution to stand for 30 minutes or more under a temperature condition of -5°C or lower is provided.

In the triglyceride production method according to the third aspect of the present invention, the specific details of the triacylglyceride, the fatty acid having an acyl group different from the acyl group in the triacylglyceride, the enzymatic esterification reaction, short path distillation and wet fractionation are As described above.

Hereinafter, the present invention will be described in more detail through examples. However, this is only provided to aid understanding of the present invention, and the scope of the present invention is not limited thereto.

[Example]

Preparation Example 1

A 1:1.8 mixture by volume of tripalmitoylglyceride (PPP, superstearin (SS)) to oleic acid (OA) was prepared.

The prepared reaction mixture was continuously introduced at a constant flow rate (28.8 mL/h, SV = 0.2) into a continuous reactor in which an enzyme (Novozym 40086, an enzyme derived from Rhizomucour miehei) exists using a metering pump while enzymatic A red transesterification reaction was performed. The reaction temperature was maintained at 60°C.

Monoacylglyceride and diacylglyceride (MAG/DAG) content of the continuous reaction product was 24.4% by weight, free fatty acid content was 62.7% by weight, and C52 content in neutral lipid was 53.4% by weight.

Thereafter, the reaction product was put into a short path distiller (SPD) (KDL 1 Basic with option B, UIC) with an internal pressure set to 5.0 to 7.0Х10 ^-2 mbar and an internal temperature set as shown in Table 1 below. The mixture was introduced at a feeding speed of 32 g/h and distilled under conditions of a roller speed of 400 rpm and a cooling temperature of 20° C. to remove by-products and residual fatty acids generated after the enzyme reaction.

Monoacylglyceride and diacylglyceride (MAG/DAG) content, free fatty acid content, and C52 content in neutral lipids of the residue obtained as a result of the distillation were analyzed, and the results are shown in Table 1 below.

[Table 1]

Preparation Example 2

The product of the continuous enzymatic transesterification reaction obtained in Preparation Example 1 was subjected to wet fractionation under the conditions of temperature, time, and amount of solvent (amount of solvent compared to reaction product in volume ratio) shown in Table 2 below. Acetone was used as a solvent for wet fractionation. That is, in the media bottle, the continuous reaction result was mixed with acetone in the ratio shown in Table 2, completely melted, put in a circulator set at the temperature shown in Table 2, taken out after the time shown in Table 2, and filtered through a membrane. Then, the filtrate was concentrated under reduced pressure to remove the solvent.

The C52 content and USU content of the wet fractionation product obtained in this way were analyzed, and the results are shown in Table 2 below.

[Table 2]

1) MAG/DAG content and free fatty acid content

It was analyzed using gas chromatography.

2) Neutral lipid carbon number analysis

Using gas chromatography, neutral lipids are separated by carbon number, and C52 (neutral lipids with a total carbon number of 52 (eg C18-C16-C18, C16-C18-C18, etc.), such as SPS, SSP, OPO, OOP , LPL, LLP, OPL, etc.) were analyzed.

3) Isomer analysis

The neutral lipid in the form of unsaturated-unsaturated-unsaturated (USU) was separated using liquid chromatography, and its concentration was analyzed. USU is mainly composed of OPO, and analysis was conducted to distinguish it from SUU including POO.

From Tables 1 and 2, it was confirmed that when the product of the enzymatic esterification reaction is purified by short-path distillation and / or wet fractionation according to the present invention, the purity of the target product can be increased while the overall yield can be maintained excellently .

Claims (11)

(1) exchanging at least one palmitoyl group of the tripalmitoyl glyceride with an oleyl group of the oleic acid by performing an enzymatic esterification reaction on a reactant mixture including tripalmitoyl glyceride and oleic acid; and
(2) distilling the resultant mixture of the enzymatic esterification reaction obtained in step (1);
The distillation comprises distilling the mixture resulting from the reaction of step (1) in a short path still under a pressure condition of 0.05 to 0.07 mbar and a temperature condition of 210 to 225 ° C.
A method for producing triglycerides. The method for producing triglyceride according to claim 1, wherein the feeding speed of the enzymatic esterification resultant mixture during short-path distillation is 20-40 g/h, and the rotational speed of the distiller roller is 300-500 rpm. The method of claim 1, wherein the monoacylglyceride and diacylglyceride content of the short path distillation residue is 20% by weight or less, the free fatty acid content is 4% by weight or less, and the total number of carbon atoms in the neutral lipid is 52. A method for producing a triglyceride having a content of 49% by weight or more. (1) exchanging at least one palmitoyl group of the tripalmitoyl glyceride with an oleyl group of the oleic acid by performing an enzymatic esterification reaction on a reactant mixture including tripalmitoyl glyceride and oleic acid; and
(2) wet fractionation of the resulting mixture of the enzymatic esterification reaction obtained in step (1);
In the wet fractionation, the reaction resultant mixture of step (1) is mixed with acetone in a volume ratio of 1:12 to 1:20 (reaction resultant mixture: acetone), and then the solution is dissolved at a temperature condition of -10 ° C. or less Including leaving for 40 minutes or more under
A method for producing triglycerides. The method of claim 4, wherein the content of neutral lipids (C52) having a total carbon number of 52 in the neutral lipids of the resultant wet fractionation is 63% by weight or more, and the content of neutral lipids in the form of unsaturated-saturated-unsaturated (USU) is 43% by weight or more , Methods for producing triglycerides. (1) exchanging at least one palmitoyl group of the tripalmitoyl glyceride with an oleyl group of the oleic acid by performing an enzymatic esterification reaction on a reactant mixture including tripalmitoyl glyceride and oleic acid; and
(2) distilling the resultant mixture of the enzymatic esterification reaction obtained in step (1); and
(3) wet fractionation of the mixture resulting from the enzymatic esterification reaction obtained in step (2);
The distillation includes distilling the mixture resulting from the reaction of step (1) in a short path still under a pressure condition of 0.05 to 0.07 mbar and a temperature condition of 210 to 225 ° C.,
In the wet fractionation, the reaction result mixture of step (1) is mixed with acetone at a volume ratio of 1:12 to 1:20 (reaction result mixture: acetone), and then the solution is dissolved at a temperature condition of -10 ° C. or less Including leaving for 40 minutes or more under
A method for producing triglycerides. 7. The process for producing a triglyceride according to any one of claims 1 to 6, wherein the triglyceride produced is dioleoyl monopalmitoyl glyceride. delete delete delete delete