CN106479682B - Oil and fat composition, preparation method and application thereof - Google Patents
Oil and fat composition, preparation method and application thereof Download PDFInfo
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- CN106479682B CN106479682B CN201510525353.8A CN201510525353A CN106479682B CN 106479682 B CN106479682 B CN 106479682B CN 201510525353 A CN201510525353 A CN 201510525353A CN 106479682 B CN106479682 B CN 106479682B
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Abstract
The present invention relates to an oil and fat composition, a method for producing the same, and use thereof. The method for producing the fat and oil composition of the present invention comprises a random transesterification step of subjecting a triglyceride to a random transesterification reaction, and is characterized in that a compound having a hydroxyl group is present in the random transesterification step. The invention relates to a grease composition with reduced content of dialkyl ketone.
Description
Technical Field
The present invention relates to an oil and fat composition, a method for producing the same, and use thereof. In particular, the invention relates to a 1, 3-dioleoyl-2-palmitoyl glyceride (OPO) composition with low dialkyl ketone (DAK) content and a preparation method thereof.
Background
1, 3-dioleoyl-2-palmitoyl glyceride (OPO) is a novel structural lipid simulating human breast milk oil, and researches show that the infant ingests the formula milk powder containing OPO to effectively improve the energy intake of the infant, soften the stool, promote the calcium absorption and reduce the crying frequency of the infant. Thus, the preparation of OPO has received extensive attention and research. Generally, an OPO oil and fat composition is prepared by subjecting triglyceride rich in palmitic acid and oleic acid to acidolysis reaction under the action of lipase. However, in order to increase the content of OPO as an active ingredient in the fat and oil composition, the one-step enzymatic reaction is often insufficient. It is necessary to increase the OPO content in combination with other processes.
CN101258230 discloses a process for preparing an OPO composition, which employs palm oil stearin having an iodine value of 2-12 and oleic acid to perform an enzymatic transesterification reaction, and increases the OPO content by dry fractionation.
CN101679909 discloses a method for producing an OPO composition by subjecting one or more glyceryl palmitostearate having an iodine value of 18 to 40 to a random transesterification reaction to increase the content of Sn-2 palmitic acid in the transesterified oil, thereby increasing the OPO content by an enzymatically directed transesterification reaction.
Compared with other processes, the method has the remarkable advantage of increasing the OPO content in the OPO composition through random ester exchange reaction. At present, the most commonly used catalyst for chemical transesterification is an alkali metal alkyl compound represented by sodium methoxide, which is cheap, easy to use, low in usage amount, and still has high activity at a low temperature. However, the transesterification reaction catalyzed by the chemical catalyst inevitably produces a byproduct such as dialkyl ketone (DAK). DAK, also known as di-fatty ketones (DFK), consists of a series of long chain fatty alkyl ketones whose basic structure is as follows: R-CO-R ', wherein R and R' represent saturated or unsaturated fatty alkyl. As early as the 70's of the 20 th century, some amount of DAK was found in margarines (Huyghebauert, R., et al (1970). "La pre sense des c toes des grandis rubbers lambtables au beer." Fette, Seifen, Anthrimitel 72(4): 289-.
DAK contained in fats and oils is reported to be difficult to remove by conching, and such substances can cause flavor instability of fats and oils, for example, bloom and crystal inhibition in chocolate applications. Therefore, studies for controlling the content of DAK in edible oils and fats have also been reported.
US5504231 discloses a process for the preparation of medium-long chain fatty acid triglycerides (MLCT) with low DAK content, which involves an esterification reaction between fatty acids and monoglycerides, the DAK content of the product being reduced by the addition of glycerol.
US6303777 discloses a process for the preparation of sucrose polyesters with low DAK content, involving a transesterification reaction between sucrose and fatty acid alcohol esters, the content of DAK in the product being controlled by controlling the reaction parameters.
WO2009012982 discloses a process for the preparation of a low DAK content OPO composition by reducing the water content of the oil and fat and the amount of sodium methoxide added and reaction time to reduce the DAK content of the product. However, these measures may result in incomplete transesterification and a reduced transesterification rate. Therefore, it is desired to reduce the content of DAK in the product as much as possible while ensuring the transesterification ratio.
Disclosure of Invention
An object of the present invention is to provide a method for producing an oil or fat composition, which comprises a random transesterification step of subjecting a triglyceride to a random transesterification reaction, characterized in that a compound having a hydroxyl group is present in the random transesterification step.
The preparation method of the grease composition further comprises the following steps of performing enzymatic oriented transesterification: a step of subjecting a triglyceride and a fatty acid or a derivative thereof to a directed transesterification reaction in the presence of a lipase.
The method for producing the fat or oil composition according to the present invention further comprises: a molecular distillation step, preferably performed before or after the enzymatic directional transesterification step.
According to the method for producing an oil and fat composition of the present invention, the triglyceride contains a triglyceride represented by the following general formula (1),
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear or branched saturated fatty acid having 8 to 30 carbon atoms.
According to the process for producing an oil or fat composition of the present invention, in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear saturated fatty acid having 16 to 18 carbon atoms.
According to the process for producing an oil or fat composition of the present invention, in the general formula (1), R1、R2And R3At least one of them represents a palmitic acid-derived group.
According to the process for producing an oil or fat composition of the present invention, in the general formula (1), R1、R2And R3And, similarly, both represent a palmitic acid derived group.
According to the method for producing the fat and oil composition of the present invention, the triglyceride is of vegetable origin.
According to the method for producing an oil and fat composition of the present invention, the triglyceride is at least one selected from the group consisting of vegetable oil stearin containing palmitic acid triglyceride, vegetable oil containing palmitic acid triglyceride, and random ester-exchanged oil and fat of vegetable oil containing palmitic acid triglyceride.
According to the method for producing the fat and oil composition of the present invention, the triglyceride is at least one selected from the group consisting of palm oil stearin, palm oil fractionated stearin, randomly transesterified palm oil, and randomly transesterified palm oil fractionated stearin.
According to the preparation method of the grease composition, the random ester exchange is chemical random ester exchange or enzymatic random ester exchange.
According to the method for preparing the grease composition, the catalyst used in the enzymatic random transesterification is non-specific lipase.
According to the preparation method of the grease composition, the non-specific lipase is Lipozyme TL IM.
According to the method for producing the fat and oil composition of the present invention, the compound having a hydroxyl group is at least one selected from the group consisting of ethylene glycol, propylene glycol, glycerin, glycerol monostearate, trimethylolethane, erythritol, pentaerythritol, sorbitol, and xylitol.
According to the method for producing an oil or fat composition of the present invention, the compound having a hydroxyl group is present in an amount of 0.01 to 1.5% by weight based on the total amount of the triglyceride.
According to the method for producing an oil or fat composition of the present invention, the compound having a hydroxyl group is present in an amount of 0.05 to 1.2 wt% based on the total amount of the triglyceride.
According to the method for producing an oil or fat composition of the present invention, the compound having a hydroxyl group is present in an amount of 0.1 to 1.0 wt% based on the total amount of the triglyceride.
According to the method for producing an oil or fat composition of the present invention, the compound having a hydroxyl group is present in an amount of 0.2 to 0.8 wt% based on the total amount of the triglyceride.
According to the method for producing an oil or fat composition of the present invention, the fatty acid is at least one selected from linear unsaturated fatty acids having 16 to 20 carbon atoms.
According to the method for producing an oil or fat composition of the present invention, the fatty acid derivative is at least one selected from esters of linear unsaturated fatty acids having 16 to 20 carbon atoms.
According to the method for producing the fat and oil composition of the present invention, the fatty acid or the derivative thereof is at least one selected from the group consisting of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower oil and high oleic palm oil.
According to the method for producing the fat and oil composition of the present invention, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, in terms of weight ratio, triglyceride: the fatty acid or derivative thereof is 1:2 to 5.
According to the method for producing the fat and oil composition of the present invention, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, in terms of weight ratio, triglyceride: the fatty acid or derivative thereof is 1:2 to 4.
According to the method for producing the fat and oil composition of the present invention, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, in terms of weight ratio, triglyceride: the fatty acid or derivative thereof is 1:2 to 3.
According to the method for producing the fat and oil composition of the present invention, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, in terms of weight ratio, triglyceride: the fatty acid or derivative thereof is 1: 2.
according to the method for producing the fat and oil composition of the present invention, the lipase is a 1, 3-specific lipase.
According to the method for producing an oil and fat composition of the present invention, the 1, 3-specific lipase is at least one selected from the group consisting of Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, candida lipase, lipase MC7, Novozym 435, candida antarctica lipase B, R275A lipase, porcine pancreatic lipase and lipase D.
The fat composition produced by the method for producing a fat composition according to the present invention.
According to the grease composition of the present invention, the content of dialkyl ketone in the composition is less than 10 ppm.
It is another object of the present invention to provide a method for preparing a fat substitute for breast milk, which comprises a random transesterification step of subjecting triglyceride to a random transesterification reaction, wherein a compound having a hydroxyl group is present in the random transesterification step.
The method for preparing a breast milk fat substitute according to the invention further comprises an enzymatic directed transesterification step: a step of subjecting a triglyceride and a fatty acid or a derivative thereof to a directed transesterification reaction in the presence of a lipase.
The method for preparing the breast milk fat substitute further comprises the following steps: a molecular distillation step, preferably performed before or after the enzymatic directional transesterification step.
The method for producing a breast milk fat substitute according to the present invention comprises a step of preparing a triglyceride represented by the following general formula (1),
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear or branched saturated fatty acid having 8 to 30 carbon atoms.
The method for preparing the breast milk fat substitute has the general formula (1) in which R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear saturated fatty acid having 16 to 18 carbon atoms.
Female according to the inventionA process for the preparation of a milk fat substitute, of the general formula (1), R1、R2And R3At least one of them represents a palmitic acid-derived group.
The method for preparing the breast milk fat substitute has the general formula (1) in which R1、R2And R3And, similarly, both represent a palmitic acid derived group.
According to the method for preparing a breast milk fat substitute of the present invention, the triglycerides are of vegetable origin.
According to the method for preparing a human milk fat substitute of the present invention, the triglyceride is at least one selected from the group consisting of vegetable oil stearin containing palmitic acid triglyceride, vegetable oil containing palmitic acid triglyceride, and random ester-exchanged oil and fat of vegetable oil containing palmitic acid triglyceride.
According to the method for preparing a human milk fat substitute of the present invention, the triglyceride is selected from at least one of palm oil stearin, palm oil stearin, randomly interesterified palm oil, or randomly interesterified palm oil stearin.
According to the method for preparing the breast milk fat substitute, the random transesterification is chemical random transesterification or enzymatic random transesterification.
According to the preparation method of the breast milk fat substitute, the catalyst used in the enzymatic random transesterification is non-specific lipase.
According to the preparation method of the breast milk fat substitute, the non-specific lipase is Lipozyme TL IM.
According to the method for preparing the breast milk fat substitute of the present invention, the compound having a hydroxyl group is selected from at least one of ethylene glycol, propylene glycol, glycerin, glycerol monostearate, trimethylolethane, erythritol, pentaerythritol, sorbitol, or xylitol.
According to the method for preparing the breast milk fat substitute, the compound with the hydroxyl group is present in an amount of 0.01-1.5 wt% based on the total amount of the triglyceride.
According to the method for preparing the breast milk fat substitute, the compound with the hydroxyl group is present in an amount of 0.05-1.2 wt% based on the total amount of the triglyceride.
According to the method for preparing the breast milk fat substitute, the compound having the hydroxyl group is present in an amount of 0.1 to 1.0 wt% based on the total amount of the triglycerides.
According to the method for preparing the breast milk fat substitute, the compound with the hydroxyl group is present in an amount of 0.2-0.8 wt% based on the total amount of the triglyceride.
According to the preparation method of the breast milk fat substitute, the fatty acid is at least one selected from linear chain unsaturated fatty acids with 16-20 carbon atoms.
According to the preparation method of the breast milk fat substitute, the fatty acid derivative is at least one selected from esters of linear unsaturated fatty acids with 16-20 carbon atoms.
According to the method for preparing the breast milk fat substitute, the fatty acid or the derivative thereof is at least one selected from oleic acid, ethyl oleate, methyl oleate, high oleic sunflower oil or high oleic palm oil.
According to the preparation method of the breast milk fat substitute, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, by weight, triglyceride: the fatty acid or derivative thereof is 1:2 to 5.
According to the preparation method of the breast milk fat substitute, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, by weight, triglyceride: the fatty acid or derivative thereof is 1:2 to 4.
According to the preparation method of the breast milk fat substitute, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, by weight, triglyceride: the fatty acid or derivative thereof is 1:2 to 3.
According to the preparation method of the breast milk fat substitute, the addition ratio of the triglyceride to the fatty acid or the derivative thereof is, by weight, triglyceride: the fatty acid or derivative thereof is 1: 2.
according to the preparation method of the breast milk fat substitute, the lipase is a 1,3 specific lipase.
According to the preparation method of the breast milk fat substitute, the 1,3 specific lipase is selected from at least one of Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida lipase, lipase MC7, Novozym 435, Candida antarctica lipase B, R275A lipase, porcine pancreatic lipase or lipase D.
The breast milk fat substitute is prepared by the preparation method of the breast milk fat substitute.
It is another object of the present invention to provide a composition comprising the above fat composition or the above breast milk fat substitute.
It is another object of the present invention to provide a food product comprising the above fat composition or the above breast milk fat substitute.
It is another object of the present invention to provide an infant formula comprising the above fat composition or the above breast milk fat substitute.
It is another object of the present invention to provide an infant formula comprising the above fat composition or the above breast milk fat substitute.
It is another object of the present invention to provide a substitute human milk fat composition comprising the above fat composition or the above human milk fat substitute.
It is another object of the present invention to provide a dietary ingredient comprising the above-described fat composition or the above-described breast milk fat substitute.
It is another object of the present invention to provide the use of the above-mentioned fat composition or the above-mentioned breast milk fat substitute for the preparation of infant formula.
It is another object of the present invention to provide the use of the above-described fat composition or the above-described breast milk fat substitute for the preparation of infant formula.
It is another object of the present invention to provide use of the above-mentioned fat composition or the above-mentioned breast milk fat substitute for preparing a breast milk fat substitute.
It is another object of the present invention to provide the use of the above-mentioned fat composition or the above-mentioned breast milk fat substitute for the preparation of a dietary ingredient.
Effects of the invention
According to the preparation method of the invention, the content of DAK in the obtained composition is obviously reduced. The preparation method of the invention does not influence the reaction process of random ester exchange. The preparation method has the advantages of simple operation process, easy realization, safe additives and low cost. The process of the present invention can also be used for other chemical transesterification products.
Detailed Description
Method for producing fat composition
The method for producing the fat and oil composition of the present invention comprises a random transesterification step of subjecting a triglyceride to a random transesterification reaction, and is characterized in that a compound having a hydroxyl group is present in the random transesterification step.
In a preferred embodiment of the production method of the present invention, the triglyceride contains a triglyceride represented by the following general formula (1),
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear or branched saturated fatty acid having 8 to 30 carbon atoms. Preferably in the formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear saturated fatty acid having 16 to 18 carbon atoms. More preferably, in the general formula (1), R1、R2And R3At least one of them represents a palmitic acid-derived group. Further preferably, in the general formula (1), R1、R2And R3And, similarly, both represent a palmitic acid derived group.
In the present invention, the fatty acid-derived group refers to a residue obtained by removing a hydroxyl group from a fatty acid.
In a preferred embodiment of the preparation process of the present invention, the triglycerides are of vegetable origin. The triglyceride derived from plant is at least one selected from vegetable oil stearin containing palmitic acid triglyceride, vegetable oil containing palmitic acid triglyceride, and random ester-exchanged oil and fat of vegetable oil containing palmitic acid triglyceride. Preferably, the vegetable-derived triglyceride is at least one selected from the group consisting of palm oil stearin, palm oil stearin, randomly interesterified palm oil, and randomly interesterified palm oil stearin.
In the present invention, the triglyceride may also be obtained by subjecting vegetable fats and oils to conventional random transesterification in the presence of a catalyst to obtain a randomized fat and oil. The vegetable oil is at least one selected from rice oil, sunflower seed oil, rape oil, palm kernel oil, peanut oil, rapeseed oil, soybean oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, olive oil, cocoa bean oil, Chinese tallow tree seed oil, almond oil, tung seed oil, rubber seed oil, corn oil, wheat germ oil, sesame seed oil, castor bean seed oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, glass chicory seed oil, sea buckthorn seed oil, tomato seed oil, macadamia nut oil, coconut oil, cocoa butter, algae oil and the like, and palm oil is preferred.
In the present invention, the randomized transesterification is a chemical random transesterification or an enzymatic random transesterification.
In a preferred embodiment of the invention, the randomized transesterification is a chemical random transesterification, the chemical catalyst used in the chemical random transesterification being an acidic catalyst or a basic catalyst; preferably, the chemical catalyst is NaOH, KOH, NaOCH3Sodium ethoxide, organic base, solid base catalyst, sulfuric acid, sulfonic acid, or solid acid catalyst; more preferably, the chemistry is catalyticThe agent is NaOH, KOH or NaOCH3Sulfuric acid or sulfonic acid.
In the embodiment of the present invention, the chemical transesterification reaction can be carried out, for example, by mixing the starting fats and oils according to a conventional method, adding 0.05 to 0.4 wt%, preferably 0.05 to 0.2 wt%, and particularly preferably 0.08 to 0.1 wt% of a catalyst to the total amount of the triglycerides, and stirring the mixture at 80 to 160 ℃ for 20 to 90 minutes under reduced pressure. After the ester exchange reaction is finished, the catalyst is passivated by hot water (the water temperature is higher than the melting point of the grease) or citric acid or phosphoric acid aqueous solution, and the ester exchange reaction is stopped. Continuing to increase the amount of chemical catalyst significantly increases the DAK content.
In an embodiment of the invention, the randomized transesterification is an enzymatic random transesterification reaction including, but not limited to, the use of a lipase as a catalyst. As the lipase, lipase powder or immobilized lipase obtained by immobilizing lipase powder on a carrier such as diatomaceous earth or ion exchange resin can be used. Lipases used in randomized transesterification reactions are transesterification reactions lacking site specificity, including but not limited to: lipases derived from Alcaligenes, lipases derived from Candida, and the like.
In the embodiment of the present invention, the enzymatic transesterification reaction may be carried out, for example, by adding 0.02 to 10% by weight of lipase powder or immobilized lipase to the raw material oil and then stirring the mixture at 40 to 80 ℃ for 0.5 to 48 hours. After the transesterification reaction is completed, the lipase powder or immobilized lipase is removed by filtration or the like.
Preferably, the catalyst used in the enzymatic random transesterification is a non-specific lipase. The non-specific lipase is Lipozyme TL IM.
After the reaction in the random transesterification step, the reaction mixture may be washed, desponmed, dried, decolorized, and filtered by a conventional method to obtain refined oils and fats.
In a preferred embodiment of the present invention, the compound having a hydroxyl group is selected from at least one of ethylene glycol, propylene glycol, glycerin, glycerol monostearate, trimethylolethane, erythritol, pentaerythritol, sorbitol, or xylitol.
In a preferred embodiment of the present invention, the compound having a hydroxyl group is present in an amount of 0.01 to 1.5% by weight, preferably 0.02 to 1.4% by weight, more preferably 0.05 to 1.2% by weight, still more preferably 0.1 to 1.0% by weight, and particularly preferably 0.2 to 0.8% by weight, based on the total amount of the triglyceride.
In a specific embodiment of the present invention, the compound having a hydroxyl group is present in an amount of 0.1 wt%, 0.2 wt%, 0.4 wt%, 0.5 wt%, 1 wt% based on the total amount of the triglyceride.
In a preferred embodiment of the present invention, the fatty acid is at least one selected from linear unsaturated fatty acids having 16 to 20 carbon atoms. Examples thereof include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, and eicosapentaenoic acid, and at least one of palmitoleic acid, oleic acid, linoleic acid, and linolenic acid is preferable.
In a preferred embodiment of the present invention, the fatty acid derivative is at least one selected from esters of linear unsaturated fatty acids having 16 to 20 carbon atoms. The ester may be an alkyl ester having 1 to 20 carbon atoms, an alkenyl ester having 2 to 20 carbon atoms, an aryl ester having 6 to 20 carbon atoms, an aralkyl ester having 7 to 20 carbon atoms, or the like of the fatty acid of the present invention.
Examples of the alkyl ester include methyl ester, ethyl ester, propyl ester, butyl ester, pentyl ester, hexyl ester, heptyl ester, octyl ester, nonyl ester, decyl ester, undecyl ester, dodecyl ester, hexadecyl ester, and octadecyl ester. Examples of the alkenyl ester include vinyl ester, propenyl ester, butenyl ester, pentenyl ester, hexenyl ester, heptenyl ester, octenyl ester, nonenyl ester, decenyl ester, undecenyl ester, dodecenyl ester, hexadecenyl ester, octadecenyl ester, and the like. Examples of the aryl ester include phenyl ester and naphthyl ester. Examples of the aralkyl ester include benzyl ester and the like. Methyl or ethyl esters are preferred.
In a preferred embodiment of the invention, the fatty acid or derivative thereof is selected from at least one of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower oil or high oleic palm oil.
In the present invention, the fatty acid or the derivative thereof is sometimes referred to as "the fatty acid or the derivative thereof of the present invention".
The addition ratio of the triglyceride to the fatty acid or the derivative thereof of the invention is, by weight ratio, triglyceride: the fatty acid or derivative thereof of the present invention is 1: 2-5, preferably 1: 2-4, more preferably 1: 2-3, more preferably 1: 2.
in a preferred embodiment of the preparation process according to the invention, an enzymatically directed transesterification step is also included: a step of subjecting a triglyceride and a fatty acid or a derivative thereof to a directed transesterification reaction in the presence of a lipase.
In a preferred embodiment of the invention, the directed transesterification is a 1, 3-directed transesterification of triglycerides.
The lipase is a 1,3 specific lipase. The 1, 3-specific lipase is at least one selected from Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida lipase, lipase MC7, Novozym 435, Candida antarctica lipase B, R275A lipase or porcine pancreatic lipase or lipase D (e.g., lipase D produced by Nippon Temminck & amp, Inc.).
The esterification reaction is preferably carried out under heating, and the heating temperature is not particularly limited as long as the object of the present invention is not impaired, and is, for example, 50 to 80 ℃, preferably 60 ℃.
The time for the esterification reaction is particularly limited as long as the object of the present invention is not impaired, and is, for example, 0.5 to 20 hours, preferably 1 to 10 hours.
In a preferred embodiment of the preparation process of the present invention, the process further comprises: a molecular distillation step, preferably performed before the enzymatic directed transesterification step, or after the enzymatic directed transesterification step, further after the enzymatic directed transesterification step. Preferably, the step of enzymatically directed transesterification is followed by a step of molecular distillation.
The distillation pressure of the molecular distillation is 0.2-3 Pa, preferably 0.5-2 Pa. The distillation temperature is 130-200 ℃, preferably 150-190 ℃.
In a preferred embodiment of the method for producing an oil or fat composition of the present invention, the method further comprises: and (3) separating the reaction product from the unreacted raw material after the transesterification. The separation method is not particularly limited, and examples thereof include filtration separation and centrifugation.
In one embodiment of the method for producing the fat and oil composition of the present invention, the random transesterification is performed by adding 1 wt% of glycerin to the palm oil stearin, based on the palm oil stearin, wherein 0.4 wt% of sodium methoxide is added, based on the palm oil stearin.
In one embodiment of the method for producing the fat and oil composition of the present invention, the random transesterification is performed by adding 0.4 wt% of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.24 wt% of sodium ethoxide is added to the palm oil stearin.
In one embodiment of the method for producing the fat and oil composition of the present invention, the random transesterification is performed by adding 0.5 wt% of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.2 wt% of sodium hydroxide is added to the palm oil stearin.
In one embodiment of the method for producing the fat and oil composition of the present invention, 1, 2-propanediol is added to palm oil in an amount of 0.1 wt% based on the palm oil, and random transesterification is performed, wherein sodium methoxide is added in an amount of 0.1 wt% based on the palm oil, and the iodine value of the palm oil is 52.
In one embodiment of the method for producing a fat and oil composition according to the present invention, 0.2 wt% of monoglyceride, based on palm oil, which has an iodine value of 52, is added to the palm oil, and random transesterification is performed, wherein 0.1 wt% of sodium methoxide, based on palm oil, is added thereto.
In one embodiment of the method for preparing the fat and oil composition of the present invention, the random transesterification step is performed by adding 1 wt% of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.4 wt% of sodium methoxide is added, based on the palm oil stearin; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation oil to obtain refined oil, mixing the refined oil and ethyl oleate according to the weight ratio of 1:2, and adding lipase D accounting for 5 wt% of the total amount of the mixed oil to perform an enzymatic directional ester exchange step; then, the oil and fat composition is subjected to molecular distillation at an evaporation temperature of 180 ℃ under an absolute pressure of 2 pa.
In one embodiment of the method for preparing the grease composition according to the present invention, the random transesterification step is performed by adding 0.1 wt% of 1, 2-propanediol to palm oil based on the palm oil, wherein 0.1 wt% of sodium methoxide is added to the palm oil based on the palm oil, and the iodine value of the palm oil is 52; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation grease to obtain refined grease, mixing the refined grease and oleic acid according to the weight ratio of 1:2, and adding Lipozyme RM IM accounting for 5 wt% of the total weight of the mixed grease to perform an enzymatic directional transesterification step; then, the oil and fat composition is subjected to molecular distillation at an evaporation temperature of 180 ℃ under an absolute pressure of 2 pa.
Oil and fat composition
The fat or oil composition of the present invention can be produced by the above-described production method of the fat or oil composition of the present invention. The composition has a reduced content of dialkyl ketones, preferably below 300ppm, more preferably below 10 ppm.
Preparation method of breast milk fat substitute
The method for producing a fat substitute for breast milk of the present invention includes a random transesterification step of subjecting triglycerides to a random transesterification reaction, and is characterized in that a compound having a hydroxyl group is present in the random transesterification step.
In a preferred embodiment of the production method of the present invention, the triglyceride contains a triglyceride represented by the following general formula (1),
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear or branched saturated fatty acid having 8 to 30 carbon atoms. Preferably in the formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear saturated fatty acid having 16 to 18 carbon atoms. More preferably, in the general formula (1), R1、R2And R3At least one of them represents a palmitic acid-derived group. Further preferably, in the general formula (1), R1、R2And R3And, similarly, both represent a palmitic acid derived group.
In the present invention, the fatty acid-derived group refers to a residue obtained by removing a hydroxyl group from a fatty acid.
In a preferred embodiment of the preparation process of the present invention, the triglycerides are of vegetable origin. The triglyceride derived from plant is at least one selected from vegetable oil stearin containing palmitic acid triglyceride, vegetable oil containing palmitic acid triglyceride, and random ester-exchanged oil and fat of vegetable oil containing palmitic acid triglyceride. Preferably, the vegetable-derived triglyceride is at least one selected from the group consisting of palm oil stearin, palm oil stearin, randomly interesterified palm oil, and randomly interesterified palm oil stearin.
In the present invention, the triglyceride may also be obtained by subjecting vegetable fats and oils to conventional random transesterification in the presence of a catalyst to obtain a randomized fat and oil. The vegetable oil is at least one selected from rice oil, sunflower seed oil, rape oil, palm kernel oil, peanut oil, rapeseed oil, soybean oil, cottonseed oil, safflower seed oil, perilla seed oil, tea seed oil, olive oil, cocoa bean oil, Chinese tallow tree seed oil, almond oil, tung seed oil, rubber seed oil, corn oil, wheat germ oil, sesame seed oil, castor bean seed oil, evening primrose seed oil, hazelnut oil, pumpkin seed oil, walnut oil, grape seed oil, glass chicory seed oil, sea buckthorn seed oil, tomato seed oil, macadamia nut oil, coconut oil, cocoa butter, algae oil and the like, and palm oil is preferred.
In the present invention, the randomized transesterification is a chemical random transesterification or an enzymatic random transesterification.
In a preferred embodiment of the invention, the randomized transesterification is a chemical random transesterification, the chemical catalyst used in the chemical random transesterification being an acidic catalyst or a basic catalyst; preferably, the chemical catalyst is NaOH, KOH, NaOCH3Sodium ethoxide, organic base, solid base catalyst, sulfuric acid, sulfonic acid, or solid acid catalyst; more preferably, the chemical catalyst is NaOH, KOH, NaOCH3Sulfuric acid or sulfonic acid.
In the embodiment of the present invention, the chemical transesterification reaction can be carried out, for example, by mixing the starting fats and oils according to a conventional method, adding 0.05 to 0.4 wt%, preferably 0.05 to 0.2 wt%, and particularly preferably 0.08 to 0.1 wt% of a catalyst to the total amount of the triglycerides, and stirring the mixture at 80 to 160 ℃ for 20 to 90 minutes under reduced pressure. After the ester exchange reaction is finished, the catalyst is passivated by hot water (the water temperature is higher than the melting point of the grease) or citric acid or phosphoric acid aqueous solution, and the ester exchange reaction is stopped. Continuing to increase the amount of chemical catalyst significantly increases the DAK content.
In an embodiment of the invention, the randomized transesterification is an enzymatic random transesterification reaction including, but not limited to, the use of a lipase as a catalyst. As the lipase, lipase powder or immobilized lipase obtained by immobilizing lipase powder on a carrier such as diatomaceous earth or ion exchange resin can be used. Lipases used in randomized transesterification reactions are transesterification reactions lacking site specificity, including but not limited to: lipases derived from Alcaligenes, lipases derived from Candida, and the like.
In the embodiment of the present invention, the enzymatic transesterification reaction may be carried out, for example, by adding 0.02 to 10% by weight of lipase powder or immobilized lipase to the raw material oil and then stirring the mixture at 40 to 80 ℃ for 0.5 to 48 hours. After the transesterification reaction is completed, the lipase powder or immobilized lipase is removed by filtration or the like.
Preferably, the catalyst used in the enzymatic random transesterification is a non-specific lipase. The non-specific lipase is Lipozyme TL IM.
After the reaction in the random transesterification step, the reaction mixture may be washed, desponmed, dried, decolorized, and filtered by a conventional method to obtain refined oils and fats.
In a preferred embodiment of the present invention, the compound having a hydroxyl group is selected from at least one of ethylene glycol, propylene glycol, glycerin, glycerol monostearate, trimethylolethane, erythritol, pentaerythritol, sorbitol, or xylitol.
In a preferred embodiment of the present invention, the compound having a hydroxyl group is present in an amount of 0.01 to 1.5% by weight, preferably 0.02 to 1.4% by weight, more preferably 0.05 to 1.2% by weight, still more preferably 0.1 to 1.0% by weight, and particularly preferably 0.2 to 0.8% by weight, based on the total amount of the triglyceride.
In a specific embodiment of the present invention, the compound having a hydroxyl group is present in an amount of 0.1 wt%, 0.2 wt%, 0.4 wt%, 0.5 wt%, 1 wt% based on the total amount of the triglyceride.
In a preferred embodiment of the present invention, the fatty acid is at least one selected from linear unsaturated fatty acids having 16 to 20 carbon atoms. Examples thereof include palmitoleic acid, oleic acid, linoleic acid, linolenic acid, eicosatrienoic acid, stearidonic acid, arachidonic acid, and eicosapentaenoic acid, and at least one of palmitoleic acid, oleic acid, linoleic acid, and linolenic acid is preferable.
In a preferred embodiment of the present invention, the fatty acid derivative is at least one selected from esters of linear unsaturated fatty acids having 16 to 20 carbon atoms. The ester may be an alkyl ester having 1 to 20 carbon atoms, an alkenyl ester having 2 to 20 carbon atoms, an aryl ester having 6 to 20 carbon atoms, an aralkyl ester having 7 to 20 carbon atoms, or the like of the fatty acid of the present invention.
Examples of the alkyl ester include methyl ester, ethyl ester, propyl ester, butyl ester, pentyl ester, hexyl ester, heptyl ester, octyl ester, nonyl ester, decyl ester, undecyl ester, dodecyl ester, hexadecyl ester, and octadecyl ester. Examples of the alkenyl ester include vinyl ester, propenyl ester, butenyl ester, pentenyl ester, hexenyl ester, heptenyl ester, octenyl ester, nonenyl ester, decenyl ester, undecenyl ester, dodecenyl ester, hexadecenyl ester, octadecenyl ester, and the like. Examples of the aryl ester include phenyl ester and naphthyl ester. Examples of the aralkyl ester include benzyl ester and the like. Methyl or ethyl esters are preferred.
In a preferred embodiment of the invention, the fatty acid or derivative thereof is selected from at least one of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower oil or high oleic palm oil.
In the present invention, the fatty acid or the derivative thereof is sometimes referred to as "the fatty acid or the derivative thereof of the present invention". .
The addition ratio of the triglyceride to the fatty acid or the derivative thereof of the invention is, by weight ratio, triglyceride: the fatty acid or derivative thereof of the present invention is 1: 2-5, preferably 1: 2-4, more preferably 1: 2-3, more preferably 1: 2.
in a preferred embodiment of the preparation process according to the invention, an enzymatically directed transesterification step is also included: a step of subjecting a triglyceride and a fatty acid or a derivative thereof to a directed transesterification reaction in the presence of a lipase.
In a preferred embodiment of the invention, the directed transesterification is a 1, 3-directed transesterification of triglycerides.
The lipase is a 1,3 specific lipase. The 1, 3-specific lipase is at least one selected from Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida lipase, lipase MC7, Novozym 435, Candida antarctica lipase B, R275A lipase or porcine pancreatic lipase or lipase D (e.g., lipase D produced by Nippon Temminck & amp, Inc.).
The esterification reaction is preferably carried out under heating, and the heating temperature is not particularly limited as long as the object of the present invention is not impaired, and is, for example, 50 to 80 ℃, preferably 60 ℃.
The time for the esterification reaction is particularly limited as long as the object of the present invention is not impaired, and is, for example, 0.5 to 20 hours, preferably 1 to 10 hours.
In a preferred embodiment of the preparation process of the present invention, the process further comprises: a molecular distillation step, preferably performed before the enzymatic directed transesterification step, or after the enzymatic directed transesterification step, further after the enzymatic directed transesterification step. Preferably, the step of enzymatically directed transesterification is followed by a step of molecular distillation.
The distillation pressure of the molecular distillation is 0.2-3 Pa, preferably 0.5-2 Pa. The distillation temperature is 130-200 ℃, preferably 150-190 ℃.
In a preferred embodiment of the method for preparing a breast milk fat substitute of the present invention, the method further comprises: and (3) separating the reaction product from the unreacted raw material after the transesterification. The separation method is not particularly limited, and examples thereof include filtration separation and centrifugation.
In one embodiment of the method for preparing a fat substitute for breast milk of the present invention, the random transesterification is performed by adding 1 wt% of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.4 wt% of sodium methoxide is added, based on the palm oil stearin.
In one embodiment of the method of preparing a human milk fat substitute of the present invention, the random transesterification is performed by adding 0.4 wt% of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.24 wt% of sodium ethoxide is added, based on the palm oil stearin.
In one embodiment of the method of preparing a human milk fat substitute of the present invention, the random transesterification is performed by adding 0.5% by weight of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.2% by weight of sodium hydroxide is added, based on the palm oil stearin.
In one embodiment of the method for preparing a fat substitute for breast milk of the present invention, 1, 2-propanediol is added to palm oil in an amount of 0.1 wt% based on palm oil, and random transesterification is performed, wherein sodium methoxide is added in an amount of 0.1 wt% based on palm oil, and the iodine value of the palm oil is 52.
In one embodiment of the method for preparing a fat substitute for breast milk of the present invention, 0.2 wt% of monoglyceride, based on palm oil, to which 0.1 wt% of sodium methoxide, based on palm oil, having an iodine value of 52, is added, is randomly transesterified.
In one embodiment of the method for preparing a breast milk fat substitute of the present invention, a random transesterification step is performed by adding 1 wt% of glycerin to palm oil stearin, based on the palm oil stearin, wherein 0.4 wt% of sodium methoxide is added, based on the palm oil stearin; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation oil to obtain refined oil, mixing the refined oil and ethyl oleate according to the weight ratio of 1:2, and adding lipase D accounting for 5 wt% of the total amount of the mixed oil to perform an enzymatic directional ester exchange step; then, the oil and fat composition is subjected to molecular distillation at an evaporation temperature of 180 ℃ under an absolute pressure of 2 pa.
In one embodiment of the method for preparing a fat substitute for breast milk of the present invention, 1, 2-propanediol is added to palm oil in an amount of 0.1 wt% based on the palm oil, and a random transesterification step is performed, wherein sodium methoxide is added in an amount of 0.1 wt% based on the palm oil, and the iodine value of the palm oil is 52; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation grease to obtain refined grease, mixing the refined grease and oleic acid according to the weight ratio of 1:2, and adding Lipozyme RM IM accounting for 5 wt% of the total weight of the mixed grease to perform an enzymatic directional transesterification step; then, the oil and fat composition is subjected to molecular distillation at an evaporation temperature of 180 ℃ under an absolute pressure of 2 pa.
Breast milk fat substitute
The human milk fat substitute of the present invention can be prepared by the above-described method for preparing a human milk fat substitute of the present invention. The milk fat substitute has a reduced content of dialkyl ketones, preferably a DAK content of less than 300ppm, more preferably less than 10 ppm.
Food product
The present invention provides a food product comprising the fat or oil composition or breast milk fat substitute of the present invention. The food product may be selected from infant formula and infant formula, bakery products including bread, especially biscuits and pastries, dairy products including milk and milk drinks, ice cream, cereal products, sauces, spreads including margarine, oils and fats, soy products, meat products, fried foods, confectionery, candy bars, candies and chocolates, snacks, drinks and shake-mix beverages, ready-to-eat beverage products, prepared foods for infants and young children and for adults including prepared purees and/or purees, sauces, cooking oils and fats and meat products.
The food products of the present invention include, but are not limited to, dairy products, fried and baked goods, meat products, sauces, beverages and the like, such as infant formulas such as milk, yogurt, ice cream, milkshakes, cheese, milk powder, cream, sterilized milk, recombined milk, fermented milk, condensed milk, milk powder, whey protein powder, cheese, processed cheese, infant formula and the like; potato chips and fried dough twists; cake, bread, battercake, snow cake, flaky pastry, moon cake, sesame seed cake, pie, toast, egg roll puff, baked pudding, egg milk sauce, biscuit, waffle, egg tart, instant noodles, instant rice, pizza, buttered tea, caramel treats, rice cake and rice dumpling; meat products: ham, roast sausage, bacon, barbecued pork, luncheon meat, jerky, dried pork slice, salted pork, preserved pork and sausage; salad sauce, crunchy candy, milk tea, coffee and tea beverage. Infant formula is preferred. In a particular embodiment of the invention, infant formula is preferred.
The food product of the present invention can be prepared by contacting the fat composition or breast milk fat substitute with a food-acceptable carrier according to a conventional method.
In the present invention, the food-acceptable carrier includes, but is not limited to, for example, starch, cellulose, dextrin, milk fat, animal and vegetable oils and fats such as sesame oil, soybean oil, peanut oil, palm oil, olive oil, corn oil, rapeseed oil, lard, beef tallow and the like, edible gums such as gum arabic, gelatin, carrageenan, xanthan gum, guar gum, sodium alginate and the like, phospholipids such as lecithin, cephalin and the like, baking powder and the like.
In the present invention, the term "infant formula" means: a milk-based infant formula or a soy-based infant formula.
Milk-based infant formula: it is a liquid or powder product made up by using milk and milk protein product as main raw material, adding proper quantity of vitamins, minerals and/or other components and adopting physical method. The energy and nutrient components of the infant formula feed are suitable for normal infants, and the energy and nutrient components of the infant formula feed can meet the normal nutritional requirements of the infants with the age of 0-6 months.
Soy-based infant formula: the soybean protein product is liquid or powder product prepared with soybean and soybean protein product as main material and proper amount of vitamins, minerals and/or other components and through physical process. The energy and nutrient components of the infant formula feed are suitable for normal infants, and the energy and nutrient components of the infant formula feed can meet the normal nutritional requirements of the infants with the age of 0-6 months.
In the present invention, the term "older infant and toddler formula" means: the milk and milk protein product and/or soybean and soybean protein product are used as main raw materials, a proper amount of vitamins, minerals and/or other auxiliary materials are added, and the liquid or powder product is prepared by only using a physical method, is suitable for being eaten by older infants and young children, and the nutritional ingredients of the product can meet the partial nutritional requirements of the older infants (6-12 months old) and the young children (12-36 months old).
The fat composition or breast milk fat substitute of the present invention can be mixed with cow's milk, goat's milk, milk powder, milk fat, etc. according to the formula design requirements when applied to infant formula food or infant formula food.
In the present invention, "infant" also refers to infants, or older infants and young children, and "infant formula" also refers to infant formula, or older infant and young child formula.
Use of
The grease composition or the breast milk fat substitute can be used for preparing infant formula milk powder.
The grease composition or breast milk fat substitute can be used for preparing infant formula food.
The fat composition or the breast milk fat substitute can be used for preparing the breast milk fat substitute.
The fat composition or breast milk fat substitute of the present invention can be used for preparing dietary ingredients.
The fat composition or breast milk fat substitute of the present invention can be used for preparing food. The features mentioned above with reference to the invention, or the features mentioned with reference to the embodiments, can be combined arbitrarily. All the features disclosed in this specification may be combined in any combination, and each feature disclosed in this specification may be replaced by alternative features serving the same, equivalent or similar purpose. Thus, unless expressly stated otherwise, the features disclosed are merely generic examples of equivalent or similar features.
The invention will be further illustrated with reference to the following specific examples. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. The experimental procedures, in which specific conditions are not noted in the following examples, are generally carried out according to conventional conditions or according to conditions recommended by the manufacturers. All percentages, ratios, proportions, or parts are by weight unless otherwise specified.
The weight volume percentage units in the present invention are well known to those skilled in the art and refer to, for example, the weight of solute in a 100 ml solution.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art. In addition, any methods and materials similar or equivalent to those described herein can be used in the methods of the present invention. The preferred embodiments and materials described herein are intended to be exemplary only.
"monoglyceride" is also referred to herein as "glyceryl monostearate". "SFC" refers to solid fat content.
Examples
Both the reactants and the catalyst in the examples of the invention are commercially available. Palm oil and palm oil stearin are from Jiali special oil (Shanghai) Co., Ltd, oleic acid is from Jiali oil chemical industry (Shanghai) Co., Ltd, sodium methoxide and sodium ethoxide are from Sigma Aldrich, lipase D and lipase Lipozyme RM IM are from Novoxil, and other chemical reagents such as glycerol are from national medicine group chemical reagent Co., Ltd.
The detection method of the DAK content in the product in the embodiment of the invention is disclosed in the patent WO 2009012982.
The product ester exchange rate in the embodiment of the invention is calculated by detecting the change of solid-fat content of raw materials and products:
transesterification rate = (SFC raw material-SFC product)/(SFC raw material-SFC equilibrium) × 100%
Wherein the SFC equilibrium is obtained by determining the products of a completely random transesterification: heating the raw oil to 105 ℃, and dehydrating for 1h under the control of a vacuum degree of 2 mbar; adding 0.4% sodium methoxide, and reacting at 105 deg.C under vacuum degree of 2mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 ℃, stirring in vacuum for 30min, dehydrating and drying to obtain a transesterification product as a sample of completely random transesterification.
Example 1
Adding 1% glycerol into 500g palm oil stearin, heating to 105 deg.C, and dehydrating at 10mbar for 1 h; adding 0.4% sodium methoxide, and reacting at 105 deg.C under vacuum degree controlled at 30mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester exchange oil 1, sampling and analyzing DAK content and ester exchange rate, and the results are shown in Table 1.
Comparative example 1a
Heating 500g of palm oil stearin to 105 ℃, and dehydrating for 1h under the condition of controlling the vacuum degree at 10 mbar; adding 0.4% sodium methoxide, and reacting at 105 deg.C under vacuum degree controlled at 30mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 2, sampling and analyzing DAK content and ester-exchanged rate, and the results are shown in Table 1.
Comparative example 1b
Heating 500g of palm oil stearin to 105 ℃, and dehydrating for 1h under the control of a vacuum degree of 10 mbar; adding 0.4% sodium methoxide, and reacting at 105 deg.C under vacuum degree controlled at 30mbar for 30 min; adding 1% glycerol, heating to 170 deg.C, reacting under vacuum for 10min to obtain ester-exchanged oil 3, sampling and analyzing DAK content and ester-exchange rate, and the results are shown in Table 1.
Comparative example 1c
500g of palm oil stearin is heated to 170 ℃, the vacuum degree is controlled at 10mbar, after 1 hour of maintenance, grease 4 is obtained, and the DAK content and the ester exchange rate are sampled and determined, and the results are shown in Table 1.
Comparative example 1d
Heating 500g palm oil stearin to 170 ℃, controlling the vacuum degree to be 10mbar, keeping the vacuum degree for 1h, adding 1% glycerol, keeping the temperature and the vacuum degree, reacting for 10min to obtain grease 5, sampling and measuring the DAK content and the ester exchange rate of the grease 5, and the results are shown in Table 1.
TABLE 1
| Numbering | DAK content (ppm) | Ester exchange ratio (%) |
| Transesterified fat 1 | 682.5 | 102.3 |
| Transesterified fat 2 | 973.2 | 99.1 |
| Transesterified fat 3 | 946.4 | 99.5 |
| Oil 4 | Not detected out | 0 |
| Oil 5 | Not detected out | 0 |
The above examples show that DAK is mainly derived from side reactions during transesterification catalyzed by a chemical catalyst such as sodium methoxide. If no catalyst is present in the system, DAK is hardly produced under high temperature conditions, and transesterification is not caused. In addition, addition of a substance such as glycerin before the start of the reaction is effective in suppressing the amount of DAK produced during the reaction. However, addition of glycerol after the end of the transesterification reaction had little effect on the reduction of DAK by the high temperature reaction.
Example 2
Adding 0.4% glycerol into 500g palm oil stearin, heating to 105 deg.C, and dehydrating at 10mbar for 1 h; adding 0.2% sodium ethoxide, and reacting at 90 deg.C under vacuum degree of 10mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 6, sampling and analyzing DAK content and ester-exchanged rate, and the results are shown in Table 2.
Comparative example 2
Heating 500g of palm oil stearin to 105 ℃, and dehydrating for 1h under the condition of controlling the vacuum degree at 10 mbar; adding 0.2% sodium ethoxide, and reacting at 90 deg.C under vacuum degree of 10mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 7, sampling and analyzing DAK content and ester-exchange rate, and the results are shown in Table 2.
Example 3
Adding 0.5% glycerol into 500g palm oil stearin, heating to 105 deg.C, and dehydrating at 10mbar for 1 h; adding 0.2% sodium hydroxide, and reacting at 120 deg.C under vacuum degree of 10mbar for 60 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 8, sampling and analyzing DAK content and ester-exchanged rate, and the results are shown in Table 2.
TABLE 2
| Numbering | DAK content (ppm) | Ester exchange ratio (%) |
| Transesterified fat 6 | 122.5 | 103 |
| Transesterified fat 7 | 231.3 | 100.7 |
| Transesterified fat 8 | 68.6 | 96.8 |
Example 4
Adding 0.1% 1, 2-propylene glycol into 500g palm oil (iodine value IV =52), heating to 105 deg.C, and dehydrating at 10mbar for 1 h; adding 0.1% sodium methoxide, and reacting at 80 deg.C under vacuum degree of 10mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 9, sampling and analyzing DAK content and ester-exchanged rate, and the results are shown in Table 3.
Example 5
Adding 0.2% monoglyceride into 500g palm oil (iodine value IV =52), heating to 105 deg.C, and dehydrating at 10mbar for 1 h; adding 0.1% sodium methoxide, and reacting at 80 deg.C under vacuum degree of 10mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 10, sampling and analyzing DAK content and ester-exchanged rate, and the results are shown in Table 3.
Comparative example 4
Heating 500g palm oil (iodine value IV =52) to 105 deg.C, and dehydrating at 10mbar for 1 h; adding 0.1% sodium methoxide, and reacting at 80 deg.C under vacuum degree of 10mbar for 30 min; a20% by weight aqueous solution of citric acid (concentration: 8%) was added to the mixture, and the mixture was stirred for 20min to terminate the reaction. The reaction was washed repeatedly with hot water until pH =7, desquamated. Heating to 105 deg.C, vacuum stirring for 30min, dehydrating and drying to obtain ester-exchanged oil 11, sampling and analyzing DAK content and ester-exchanged rate, and the results are shown in Table 3.
TABLE 3
| Numbering | DAK content (ppm) | Ester exchange ratio (%) |
| Transesterified fat 9 | 20.7 | 106.4 |
| Transesterified fat or oil 10 | 25.2 | 97 |
| Transesterified fat 11 | 50.5 | 98.6 |
Example 6
The transesterified fat 1 of example 1 was subjected to molecular distillation at an evaporation temperature of 200 ℃, a heat exchanger temperature of 40 ℃, a rotation speed of 250rpm and an absolute pressure of 2 pa. The heavy phase was collected to give molecular distilled oil 1, and the DAK content was measured, the results of which are shown in Table 4.
Adding activated clay 2 wt% into the molecular distillation oil 1, maintaining at 110 deg.C for 30min for decolorizing, and filtering to obtain decolorized oil. Heating the oil to 240 ℃, deodorizing for 3h under the blowing of 2mbar and nitrogen gas to obtain refined oil 1. 200g of refined oil 1 and ethyl oleate are mixed according to a ratio of 1:2, lipase D accounting for 5% of the total amount of the mixed oil is added for enzymatic directional ester exchange, the reaction temperature is 60 ℃, the enzyme is filtered and removed after 5 hours of reaction, and an oil composition is obtained, and molecular distillation is carried out on the oil composition, wherein the evaporation temperature is 180 ℃, the temperature of a heat exchanger is 50 ℃, the rotating speed is 250rpm, and the absolute pressure is 2 pa. The heavy phase was collected to give OPO composition 1 and the DAK content was determined and the results are shown in Table 4.
Comparative example 5
The ester-exchanged fat 2 of comparative example 1a was added with 2% by weight of activated clay, and kept at 110 ℃ for 30min for decolorization, and filtered to obtain a decolorized fat. Heating the oil to 240 ℃, deodorizing for 3h under the blowing of 2mbar and nitrogen gas to obtain refined oil 2. 200g of refined oil 2 and ethyl oleate are mixed according to the proportion of 1:2, lipase D accounting for 5 percent of the weight of the mixed oil is added for enzymatic directional ester exchange, the reaction temperature is 60 ℃, the enzyme is filtered and removed after 5 hours of reaction, and the oil composition is obtained and subjected to molecular distillation, the evaporation temperature is 180 ℃, the temperature of a heat exchanger is 50 ℃, the rotation speed is 250rpm, and the absolute pressure is 2 pa. The heavy phase was collected to give OPO composition 2 and the DAK content was determined and the results are shown in Table 4.
TABLE 4
| Numbering | DAK content (ppm) |
| Transesterified fat 1 | 682.5 |
| Molecular distillation of oil and fat 1 | 457.8 |
| Refined fat 1 | 435.7 |
| OPO composition 1 | 278.1 |
| Transesterified fat 2 | 973.2 |
| Refined fat 2 | 922.5 |
| OPO composition 2 | 654.3 |
Example 7
The transesterified fat 9 of example 4 was subjected to molecular distillation at an evaporation temperature of 200 ℃, a heat exchanger temperature of 40 ℃, a rotation speed of 250rpm and an absolute pressure of 2 pa. The heavy phase was collected to give molecular distilled oil 2, and the DAK content was measured, the results of which are shown in Table 5.
Adding activated clay 2 wt% into the above molecular distilled oil, decolorizing at 110 deg.C for 30min, and filtering to obtain decolorized oil. Heating the oil to 240 ℃, deodorizing for 3 hours under the blowing of 2mbar and nitrogen gas to obtain refined oil 3. 200g of the refined oil and oleic acid are mixed according to the proportion of 1:2, Lipozyme RM IM accounting for 5 percent of the total amount of the mixed oil is added for enzyme-method oriented transesterification, the reaction temperature is 60 ℃, the enzyme is filtered and removed after 5 hours of reaction, the oil composition is obtained, the residual fatty acid is removed by molecular distillation, the evaporation temperature is 180 ℃, the temperature of a heat exchanger is 50 ℃, the rotating speed is 250rpm, and the absolute pressure is 2 pa. The heavy phase was collected to give OPO composition 3 and the DAK content was determined and the results are shown in Table 5.
TABLE 5
| Numbering | DAK content (ppm) |
| Transesterified fat 9 | 20.7 |
| Molecular distillation of oil 2 | 11.8 |
| Refined fat 3 | 10.5 |
| OPO composition 3 | 3.1 |
The treatment described in example 8 was carried out on the transesterified fat 10, and the OPO composition 4 obtained also had a DAK content of less than 10 ppm.
The above examples show that the addition of high boiling point materials containing hydroxyl groups, such as glycerol, propylene glycol, monoglycerides, etc., during chemical transesterification, significantly reduces the DAK content of the product and ensures that the transesterification reaction is not affected. In addition, DAK substances generated during the chemical transesterification process are difficult to remove by the conventional refining process, but the molecular distillation can remove the formed DAK to a greater extent. The method provided by the invention is adopted to prepare OPO composition, the DAK content of which can be obviously reduced, preferably the DAK content of which is reduced by more than half, preferably the DAK content of which is lower than 300ppm, and more preferably the DAK content of which is lower than 10 ppm. Meanwhile, the method of the invention can be suitable for chemical ester exchange reactions of different raw materials, and the content of DAK in the product can be controlled.
The foregoing is merely a preferred embodiment of the invention and is not intended to limit the scope of the invention, which is defined by the claims appended hereto, and any other technical entity or method that is encompassed by the claims as broadly defined herein, or equivalent variations thereof, is contemplated as being encompassed by the claims.
Claims (60)
1. A process for producing an oil or fat composition, which comprises a random transesterification step of subjecting triglycerides to a random transesterification reaction, characterized in that a compound having a hydroxyl group is present in the random transesterification step, the compound having a hydroxyl group is added before the start of the chemical random transesterification reaction,
the compound with hydroxyl is at least one of propylene glycol, glycerol or glyceryl monostearate,
the random transesterification is a chemical random transesterification,
an acidic catalyst or a basic catalyst is used in the chemical random transesterification reaction.
2. The method for producing a fat or oil composition according to claim 1, further comprising an enzymatically-directed transesterification step of: a step of subjecting a triglyceride and a fatty acid or a derivative thereof to a directed transesterification reaction in the presence of a lipase.
3. The method for producing the grease composition according to claim 2, further comprising: a molecular distillation step, which is performed before or after the enzymatic directional transesterification step.
4. The method for producing an oil and fat composition according to claim 1 or 2, wherein the triglyceride contains a triglyceride represented by the following general formula (1),
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear or branched saturated fatty acid having 8 to 30 carbon atoms.
5. The method for producing an oil or fat composition according to claim 4, wherein R in the general formula (1)1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear saturated fatty acid having 16 to 18 carbon atoms.
6. The method for producing an oil or fat composition according to claim 5, wherein R in the general formula (1)1、R2And R3At least one of them represents a palmitic acid-derived group.
7. The method for producing an oil or fat composition according to claim 4, wherein R in the general formula (1)1、R2And R3And, similarly, both represent a palmitic acid derived group.
8. The method for producing an oil or fat composition according to claim 1 or 2, wherein the triglyceride is of vegetable origin.
9. The method for producing a fat and oil composition according to claim 8, wherein the triglyceride is at least one selected from the group consisting of vegetable oil stearin containing palmitic triglyceride, vegetable oil containing palmitic triglyceride, and random ester-exchanged fat and oil of vegetable oil containing palmitic triglyceride.
10. The method for producing a fat and oil composition according to claim 9, wherein the triglyceride is at least one selected from the group consisting of palm oil stearin, palm oil stearin, randomly transesterified palm oil, and randomly transesterified palm oil stearin.
11. The method for producing an oil or fat composition according to claim 1 or 2, wherein the compound having a hydroxyl group is present in an amount of 0.01 to 1.5 wt% based on the total amount of the triglyceride.
12. The method for producing an oil or fat composition according to claim 1 or 2, wherein the compound having a hydroxyl group is present in an amount of 0.05 to 1.2 wt% based on the total amount of the triglyceride.
13. The method for producing an oil or fat composition according to claim 1 or 2, wherein the compound having a hydroxyl group is present in an amount of 0.1 to 1.0 wt% based on the total amount of the triglyceride.
14. The method for producing an oil or fat composition according to claim 1 or 2, wherein the compound having a hydroxyl group is present in an amount of 0.2 to 0.8 wt% based on the total amount of the triglyceride.
15. The method for producing an oil or fat composition according to claim 2, wherein the fatty acid is at least one selected from linear unsaturated fatty acids having 16 to 20 carbon atoms.
16. The method for producing an oil or fat composition according to claim 2, wherein the fatty acid derivative is at least one selected from esters of linear unsaturated fatty acids having 16 to 20 carbon atoms.
17. The method for producing an oil or fat composition according to claim 2, wherein the fatty acid or the derivative thereof is at least one selected from the group consisting of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower oil and high oleic palm oil.
18. The method for producing a fat or oil composition according to claim 2, wherein the triglyceride and the fatty acid or a derivative thereof are added in a ratio of triglyceride: the fatty acid or derivative thereof is 1:2 to 5.
19. The method for producing a fat or oil composition according to claim 2, wherein the triglyceride and the fatty acid or a derivative thereof are added in a ratio of triglyceride: the fatty acid or derivative thereof is 1:2 to 4.
20. The method for producing a fat or oil composition according to claim 2, wherein the triglyceride and the fatty acid or a derivative thereof are added in a ratio of triglyceride: the fatty acid or derivative thereof is 1:2 to 3.
21. The method for producing a fat or oil composition according to claim 2, wherein the triglyceride and the fatty acid or a derivative thereof are added in a ratio of triglyceride: the fatty acid or derivative thereof is 1: 2.
22. the method for producing an oil or fat composition according to claim 2, wherein the lipase is a 1, 3-specific lipase.
23. The method for producing an oil or fat composition according to claim 22, wherein the 1, 3-specific lipase is at least one selected from Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida lipase, lipase MC7, Novozym 435, Candida antarctica lipase B, R275A lipase, porcine pancreatic lipase or lipase D.
24. A method for preparing a fat substitute for breast milk, which comprises a random transesterification step of subjecting triglycerides to a random transesterification reaction, characterized in that a compound having a hydroxyl group is present in the random transesterification step, the compound having a hydroxyl group is added before the start of the chemical random transesterification reaction,
the compound having a hydroxyl group is selected from at least one of propylene glycol, glycerin and glyceryl monostearate,
the random transesterification is a chemical random transesterification,
an acidic catalyst or a basic catalyst is used in the chemical random transesterification reaction.
25. The method of preparing a human milk fat substitute according to claim 24, further comprising the step of enzymatically directing transesterification: a step of subjecting a triglyceride and a fatty acid or a derivative thereof to a directed transesterification reaction in the presence of a lipase.
26. The method of preparing a breast milk fat substitute according to claim 25, further comprising: a molecular distillation step, which is performed before or after the enzymatic directional transesterification step.
27. The method for producing a human milk fat substitute according to claim 24 or 25, wherein the triglyceride contains a triglyceride represented by the following general formula (1),
in the general formula (1), R1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear or branched saturated fatty acid having 8 to 30 carbon atoms.
28. The method for producing a human milk fat substitute according to claim 27, wherein R is represented by general formula (1)1、R2And R3Each being the same or different, R1、R2And R3At least one of the (a) and (b) represents a group derived from a linear saturated fatty acid having 16 to 18 carbon atoms.
29. The method for producing a human milk fat substitute according to claim 28, wherein R is represented by general formula (1)1、R2And R3At least one of them represents a palmitic acid-derived group.
30. The method for producing a human milk fat substitute according to claim 29, wherein R is represented by general formula (1)1、R2And R3And, similarly, both represent a palmitic acid derived group.
31. The method of preparing a breast milk fat substitute according to claim 24 or 25, said triglycerides being of vegetable origin.
32. The method of preparing a human milk fat substitute according to claim 31, wherein the triglyceride is at least one selected from the group consisting of vegetable oil stearin containing palmitic triglyceride, vegetable oil containing palmitic triglyceride, and random interesterified oil of vegetable oil containing palmitic triglyceride.
33. The method of preparing a human milk fat substitute according to claim 31, wherein the triglyceride is selected from at least one of palm oil stearin, palm oil stearin, randomly interesterified palm oil, or randomly interesterified palm oil stearin.
34. The method of preparing a human milk fat substitute according to claim 24 or 25, wherein said compound having a hydroxyl group is present in an amount of 0.01 to 1.5 wt.% based on the total amount of said triglycerides.
35. The method of preparing a human milk fat substitute according to claim 24 or 25, wherein said compound having a hydroxyl group is present in an amount of 0.05 to 1.2 wt.% based on the total amount of said triglycerides.
36. The method of preparing a human milk fat substitute according to claim 24 or 25, wherein said compound having a hydroxyl group is present in an amount of 0.1 to 1.0 wt.% based on the total amount of said triglycerides.
37. The method of preparing a human milk fat substitute according to claim 24 or 25, wherein said compound having a hydroxyl group is present in an amount of 0.2-0.8 wt.% based on the total amount of triglycerides.
38. The method for producing a human milk fat substitute according to claim 25, wherein the fatty acid is at least one selected from linear unsaturated fatty acids having 16 to 20 carbon atoms.
39. The method for producing a human milk fat substitute according to claim 25, wherein the fatty acid derivative is at least one selected from esters of linear unsaturated fatty acids having 16 to 20 carbon atoms.
40. The method of claim 25, wherein the fatty acid or derivative is at least one selected from the group consisting of oleic acid, ethyl oleate, methyl oleate, high oleic sunflower oil and high oleic palm oil.
41. The method of preparing a human milk fat substitute according to claim 25, wherein said triglyceride is added to said fatty acid or derivative thereof in a ratio of triglyceride: the fatty acid or derivative thereof is 1:2 to 5.
42. The method of preparing a human milk fat substitute according to claim 25, wherein said triglyceride is added to said fatty acid or derivative thereof in a ratio of triglyceride: the fatty acid or derivative thereof is 1:2 to 4.
43. The method of preparing a human milk fat substitute according to claim 25, wherein said triglyceride is added to said fatty acid or derivative thereof in a ratio of triglyceride: the fatty acid or derivative thereof is 1:2 to 3.
44. The method of preparing a human milk fat substitute according to claim 25, wherein said triglyceride is added to said fatty acid or derivative thereof in a ratio of triglyceride: the fatty acid or derivative thereof is 1: 2.
45. the method of claim 25, wherein the lipase is a 1,3 specific lipase.
46. The method for producing a human milk fat substitute according to claim 45, wherein the 1, 3-specific lipase is at least one selected from Lipozyme RM IM, Lipozyme IM60, Lipozyme IM20, lipase SP435, lipase SP382, Candida lipase, lipase MC7, Novozym 435, Candida antarctica lipase B, R275A lipase, porcine pancreatic lipase or lipase D.
47. A method for producing an oil or fat composition, wherein 1 wt.% of glycerin based on palm oil stearin is added to palm oil stearin to carry out random transesterification, wherein 0.4 wt.% of sodium methoxide based on palm oil stearin is added, and the random transesterification is chemical random transesterification, and the glycerin is added before the start of the chemical random transesterification.
48. A method for producing an oil or fat composition, wherein 0.4% by weight of glycerin based on palm oil stearin is added to the palm oil stearin to carry out random transesterification, wherein 0.24% by weight of sodium ethoxide based on palm oil stearin is added, and the random transesterification is chemical random transesterification, and the glycerin is added before the start of the chemical random transesterification.
49. A method for producing an oil or fat composition, wherein 0.5% by weight of glycerin based on palm oil stearin is added to the palm oil stearin to carry out random transesterification, wherein 0.2% by weight of sodium hydroxide based on palm oil stearin is added, and the random transesterification is chemical random transesterification, and the glycerin is added before the start of the chemical random transesterification.
50. A method for producing an oil or fat composition, wherein 1, 2-propanediol is added to palm oil in an amount of 0.1 wt.% based on the palm oil, and a random transesterification is carried out, wherein sodium methoxide is added in an amount of 0.1 wt.% based on the palm oil, the palm oil has an iodine value of 52, and the random transesterification is a chemical random transesterification, and the 1, 2-propanediol is added before the start of the chemical random transesterification.
51. A method for producing an oil or fat composition, wherein a random transesterification is carried out by adding 0.2% by weight of monoglyceride to palm oil based on the amount of palm oil, wherein 0.1% by weight of sodium methoxide based on the amount of palm oil is added, the iodine value of the palm oil is 52, and the random transesterification is a chemical random transesterification, and wherein the monoglyceride is added before the start of the chemical random transesterification.
52. A method for preparing oil and fat composition comprises adding 1 wt% of glycerol into palm oil stearin based on palm oil stearin, and performing random transesterification, wherein 0.4 wt% of sodium methoxide based on palm oil stearin is added; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation oil to obtain refined oil, mixing the refined oil and ethyl oleate according to the weight ratio of 1:2, and adding lipase D accounting for 5 wt% of the total amount of the mixed oil to perform an enzymatic directional ester exchange step; and then carrying out molecular distillation on the grease composition, wherein the evaporation temperature is 180 ℃, the absolute pressure is 2pa, the random ester exchange is chemical random ester exchange, and the glycerol is added before the chemical random ester exchange reaction starts.
53. A method for preparing oil and fat composition comprises adding 0.1 wt% of 1, 2-propylene glycol into palm oil based on palm oil, and performing random transesterification, wherein 0.1 wt% of sodium methoxide is added based on palm oil, and iodine value of palm oil is 52; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation grease to obtain refined grease, mixing the refined grease and oleic acid according to the weight ratio of 1:2, and adding Lipozyme RM IM accounting for 5 wt% of the total weight of the mixed grease to perform an enzymatic directional transesterification step; and then carrying out molecular distillation on the grease composition, wherein the evaporation temperature is 180 ℃, the absolute pressure is 2pa, the random ester exchange is chemical random ester exchange, and the 1, 2-propylene glycol is added before the chemical random ester exchange reaction starts.
54. A method for preparing a fat substitute for human milk, wherein 1 wt.% of glycerin, based on palm oil stearin, is added to palm oil stearin to carry out random transesterification, wherein 0.4 wt.% of sodium methoxide, based on palm oil stearin, is added to the palm oil stearin, the random transesterification is chemical random transesterification, and the glycerin is added before the chemical random transesterification reaction is started.
55. A method for preparing human milk fat substitute comprises adding 0.4 wt% of glycerol to palm oil stearin based on palm oil stearin, and performing random transesterification, wherein 0.24 wt% of sodium ethoxide is added based on palm oil stearin, and the random transesterification is chemical random transesterification, and the glycerol is added before the chemical random transesterification reaction is started.
56. A method for preparing a fat substitute for human milk, wherein 0.5 wt.% of glycerin based on palm oil stearin is added to the palm oil stearin to carry out random transesterification, wherein 0.2 wt.% of sodium hydroxide based on palm oil stearin is added, and the random transesterification is chemical random transesterification, and the glycerin is added before the chemical random transesterification reaction is started.
57. A method for preparing a fat substitute for breast milk, wherein 1, 2-propanediol is added to palm oil in an amount of 0.1 wt% based on palm oil, and a random transesterification is performed, wherein sodium methoxide is added in an amount of 0.1 wt% based on palm oil, the palm oil has an iodine value of 52, and the random transesterification is a chemical random transesterification, and the 1, 2-propanediol is added before the start of the chemical random transesterification.
58. A method for preparing a fat substitute for human milk, wherein monoglyceride is added to palm oil in an amount of 0.2 wt.% based on the palm oil, and random interesterification is performed, wherein sodium methoxide is added in an amount of 0.1 wt.% based on the palm oil, the palm oil has an iodine value of 52, and the random interesterification is chemical random interesterification, and the monoglyceride is added before the start of the chemical random interesterification reaction.
59. A method for preparing breast milk fat substitute comprises adding 1 wt% of glycerol to palm oil stearin based on palm oil stearin, and performing random transesterification, wherein 0.4 wt% of sodium methoxide based on palm oil stearin is added; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation oil to obtain refined oil, mixing the refined oil and ethyl oleate according to the weight ratio of 1:2, and adding lipase D accounting for 5 wt% of the total amount of the mixed oil to perform an enzymatic directional ester exchange step; and then carrying out molecular distillation on the grease composition, wherein the evaporation temperature is 180 ℃, the absolute pressure is 2pa, the random ester exchange is chemical random ester exchange, and the glycerol is added before the chemical random ester exchange reaction starts.
60. A method for preparing breast milk fat substitute comprises adding 0.1 wt% of 1, 2-propylene glycol to palm oil based on palm oil, and performing random transesterification, wherein 0.1 wt% of sodium methoxide is added to palm oil based on palm oil, and iodine value of palm oil is 52; further carrying out a molecular distillation step, wherein the evaporation temperature is 200 ℃ and the absolute pressure is 2 pa; subsequently, refining the obtained molecular distillation grease to obtain refined grease, mixing the refined grease and oleic acid according to the weight ratio of 1:2, and adding Lipozyme RM IM accounting for 5 wt% of the total weight of the mixed grease to perform an enzymatic directional transesterification step; and then carrying out molecular distillation on the grease composition, wherein the evaporation temperature is 180 ℃, the absolute pressure is 2pa, the random ester exchange is chemical random ester exchange, and the 1, 2-propylene glycol is added before the chemical random ester exchange reaction starts.
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| US6121440A (en) * | 1998-01-29 | 2000-09-19 | The Procter & Gamble Company | Process for synthesis of polyol fatty acid polyesters |
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