CN102965404A - Preparation method of high-purity diglyceride - Google Patents
Preparation method of high-purity diglyceride Download PDFInfo
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Abstract
The invention discloses a preparation method of high-purity diglyceride, which comprises the following steps: 1) under the catalytic action of partial glyceride lipase, reacting a fatty acid donor and glycerol to synthesize a mixture containing diglyceride and monoglyceride, performing centrifugal separation on the mixture, and recovering the supernatant oil phase; 2) under the catalytic action of monoglyceride lipase, reacting the monoglyceride in the oil phase obtained in the step 1) and a hydroxyl donor, thus converting to obtain non-glyceride; 3) separating the non-glyceride component in the mixture obtained in the step 2) from the diglyceride, thus obtaining the high-purity diglyceride. According to the invention, the monoglyceride in the mixture is selectively removed through an enzyme method, the separation process is simplified, the energy consumption of the separation process is reduced, and the problem on the separation of MAG in the mixture is well solved. Meanwhile, the diglyceride content in the prepared product is up to 98% or above.
Description
Technical field
The present invention relates to a kind of preparation method of high purity of diglycerides.
Background technology
Triglyceride (be called for short DAG) is by the product that obtains behind glycerol (glycerine) and two fatty acid esterifications, is the natural component of grease, also is the intermediate product of fat metabolic.The functional edible oil of triglyceride is the new oil that forms take natural edible oil as raw material, by enzyme process or chemical method modification, have clear and definite function and the edible safeties such as obesity, reducing blood-fat of preventing, regeneration product as oil with common edible, can fundamentally alleviate because the present situation of the chronic disease increased popularity such as the caused obesity of diet formula of high grease, high calorie, high blood ester, diabetes is regulated generation and the development of human-body sub-health level and the relevant chronic disease of containment under the prerequisite that does not change existing food habits.The source of the relative content Main Basis edible oil of DAG in the natural fats and oils and difference contains 5.5% triglyceride such as sweet oil is 9.5% in the Oleum Gossypii semen.
Since lipase can be under the condition of gentleness the catalysis oil modification, quality and the unsaturated fatty acids of grease had good provide protection, therefore caused more and more widely about the research of investigation on enzymatic synthesis of diglyceride in recent years and paid close attention to.Highly purified triglyceride product is the important raw and processed materials of proceeding triglyceride physico-chemical property and physiological function research, also is one of developing direction of triglyceride production technique.Lipase-catalyzed lipid acid and glycerine or lipid acid low-carbon alkyl and glycerine are the important channel of synthetic triglyceride by esterification or transesterification reaction; also be to be used at present mass-producing to prepare the unique channel of higher degree triglyceride; compare with additive method; the feasibility that the method is accomplished scale production is large, and the purity of the triglyceride that obtains is higher.The triglyceride level that produces in the control esterification reaction process is the key that improves DAG purity in the product.
Generally contain triglyceride level and direactive glyceride (MAG) in the existing triglyceride synthesis technique, because triglyceride level and triglyceride are difficult to effective separation, so that the purity of DAG is lower in the product; Utilize lipase to the specificity of glyceryl ester substrate; can at first utilize partial glyceride lipase that acry radical donor is changed into the mixture that contains DAG and MAG, then by techniques such as molecular distillations the MAG in the reaction mixture be separated with unreacted acry radical donor and remove.This seminar studies show that, utilizes the mode of distillation to remove the vaporization temperature that MAG need to be higher, and this has just caused the energy consumption of technique to improve, and is not suitable for the product that some contain the lipid acid of the easy oxidation of being heated.
Summary of the invention
For overcoming the not segregative defective of MAG in traditional high purity of diglycerides synthesis technique, the invention provides a kind of preparation method of high purity of diglycerides.In the present invention, adopt the synthetic mixture that contains DAG and MAG of partial glyceride lipase catalysis lipid acid donor and glycerine reaction, recycling direactive glyceride lipase changes into the nonglyceride form with the MAG in the mixture, obtains highly purified triglyceride product finally by crossing separating technology.
Technical scheme of the present invention is as follows:
A kind of preparation method of high purity of diglycerides may further comprise the steps:
1) utilizes the synthetic mixture that contains triglyceride and direactive glyceride of partial glyceride lipase catalysis lipid acid donor and glycerine reaction, said mixture is carried out centrifugation, reclaim upper oil phase;
2) utilizing the lipase-catalyzed step 1 of direactive glyceride) direactive glyceride and hydroxyl in the oil phase that obtains change into nonglyceride for precursor reactant;
3) with step 2) in the mixture that obtains the nonglyceride composition separate with triglyceride, obtain highly purified triglyceride.Through above reaction, comprise triglyceride, lipid acid or lipid acid low-carbon alkyl in the reaction product, for this product system, generally be to adopt the mode of molecular distillation or short-path distillation to separate, difference according to the boiling point of material is separated above each component, obtain the high temperature cut take triglyceride as main ingredient, be the purpose product.
Preferably, the lipid acid donor described in the step 1) is one or more the mixture in lipid acid, lipid acid low-carbon alkyl or the raw material that contains lipid acid, lipid acid low-carbon alkyl; Step 2) donor of hydroxyl described in is one or both the mixture in water and the short chain alcohol.
Preferably, described lipid acid is for having one or more the mixture in the lipid acid of 6 ~ 22 carbon atoms.
Preferably, described lipid acid low-carbon alkyl is one or both the mixture in methyl esters, ethyl ester, propyl ester, butyl ester, the pentyl ester.
Preferably, the mixture of one or more in described short chain alcohol methyl alcohol, ethanol, propyl alcohol, butanols, the amylalcohol.
Preferably, adopt the method for programmed cooling, with step 2) in the temperature of enzyme reaction to be controlled at the fusing point of direactive glyceride (MAG) mixture interval.
Preferably, the method for described programmed cooling is down to 30 ℃ and is continued 1 hour for per hour reducing by 5 ~ 10 ℃.
Preferably, the mol ratio 1:(0.3 of the donor of lipid acid described in the step 1) and glycerine ~ 4); The mol ratio 1:(4 of direactive glyceride step 2) (MAG) and hydroxyl donor ~ 10).
Preferably, the addition of described partial glyceride lipase is based on step 1) reaction mixture total mass 120 ~ 240U/g; The addition of described direactive glyceride lipase is based on step 2) reaction mixture total mass 100 ~ 200U/g.
Preferably, the partial glyceride lipase described in the step 1) is one or both among LipaseSMG1, the LipaseG50; Step 2) the direactive glyceride lipase described in is one or both among direactive glyceride lipase MGL, the direactive glyceride lipase bMGL.
Utilize the product specificity of partial glyceride lipase; the acry radical donor of lipid acid can be changed into the glyceride mixture as leading take DAG and MAG; do not contain TAG in the mixture, can obtain purity after the DAG separation and purification in the product at the triglyceride product more than 90%.But well-known, MAG is a kind of common nonionic emulsifier, has stronger emulsifying property, can not utilize the mode of alkali neutralization to remove, and generally is to separate by the mode of molecular distillation.But because the molecular weight of direactive glyceride is larger, vaporization temperature required by molecular distillation the time is higher, and the lipid acid of easy oxidation is damaged easily so that some are heated, and has increased the weight of burden and difficulty that later separation is extracted.Step 2 of the present invention) be on the reaction basis of step 1), get the oil phase of step 1) reactant, the alcohol that adds entry or short chain, this mixture is lipase-catalyzed through direactive glyceride, optionally the MAG in the step 1) product is changed into the low-carbon alkyl of lipid acid or lipid acid.This is just so that the composition of required separation is the mixture of the low-carbon alkyl of DAG and lipid acid or lipid acid, lipid acid can be removed by the technique of alkali neutralization, the low-carbon alkyl of lipid acid and lipid acid also can be removed under lower vaporization temperature by the technique of extraction process or molecular distillation, and the mode of preferred molecular distillation is removed lipid acid.
Utilize direactive glyceride lipase can optionally MAG be changed into the nonglyceride form, short chain alcohol ester such as lipid acid or lipid acid, this just can utilize lower distillation temperature that the DAG in the mixture is carried out separation and purification, reduced the energy consumption of separating technology, the damage that can avoid the acid of high temperature commute oxidation of fat to produce simultaneously.But the contriver studies show that, direactive glyceride lipase is when the MAG in the catalyzed oil lipoprotein mixture and hydroxyl are for precursor reactant under constant temp, exists reaction process slow or react halfway phenomenon.Further research is found, with hydroxyl during for precursor reactant, in the temperature range of direactive glyceride lipase non-inactivation, temperature more high reaction rate is faster at the lipase-catalyzed MAG of direactive glyceride, and still the removal degree of MAG is on the contrary less when reaction reaches balance; And when reacting under the temperature of the fusing point of MAG, speed of reaction is low, but the removal degree of MAG is high.Therefore, consider the removal effect of speed of reaction and MAG, the present invention adopts the mode of programmed cooling when utilizing the lipase-catalyzed MAG of direactive glyceride and hydroxyl donor to react, and temperature range is that the fusing point of MAG in the substrate is interval.
Compared with prior art, the present invention has following advantage:
(1) among the present invention, takes enzyme process optionally to remove direactive glyceride in the mixture, simplified separating technology, reduced the energy consumption of separating technology, solved well the problem that MAG separates in the mixture.
(2) the present invention is on the basis of step 1), by having increased step 2) operation, remedied the deficiency that step 1) is reacted, the direactive glyceride in the step 1) reaction product is changed into the nonglyceride composition, follow-up separating technology is simplified.
(3) reaction that enzyme process is optionally removed MAG step 2), the method for employing programmed cooling, temperature controlling range are that the fusing point of MAG is interval, can in the removal effect that guarantees MAG, improve speed of reaction.
(4) the synthetic triglyceride level of partial glyceride lipase used in the present invention, mono-glycerides lipase can only react by the catalysis direactive glyceride, so the content high (more than 98%) of triglyceride in the product of present method preparation.
Embodiment
Introduce in more detail by the following examples enforcement of the present invention.In described embodiment, all per-cents all in mass.
Embodiment 1
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 184g glycerine (mol ratio is 1:2) and 4.7g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the water with respect to 4 times of direactive glyceride (MAG) mole numbers in the oil phase that recovery obtains, direactive glyceride lipase MGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, (reacting initial temperature is 60 ℃ to programmed cooling, per hour reduces by 10 ℃, is down to 30 ℃, continue 1 hour at 30 ℃), the hydrolysis reaction product composition sees Table 1 behind the reaction 4h.The hydrolysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid of removing wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
Embodiment 2
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseG50 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the dehydrated alcohol with respect to 4 times of MAG mole numbers in the oil phase that recovery obtains, direactive glyceride lipase bMGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, (reacting initial temperature is 60 ℃ to programmed cooling, per hour reduces by 10 ℃, is down to 30 ℃, continue 1 hour at 30 ℃), the hydrolysis reaction product composition sees Table 1 behind the reaction 4h.The alcoholysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid removed wherein or fatty-acid ethyl ester and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
Embodiment 3
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the water with respect to 6 times of MAG mole numbers in the oil phase that recovery obtains, direactive glyceride lipase bMGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, (reacting initial temperature is 60 ℃ to programmed cooling, per hour reduces by 10 ℃, is down to 30 ℃, continue 1 hour at 30 ℃), the hydrolysis reaction product composition sees Table 1 behind the reaction 4h.The hydrolysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid of removing wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
Embodiment 4
(lipid acid consists of: 80% ethyl oleate to get the ethyl oleate of 295g, 10% ethyl linoleate, 2% Stearic ethyl stearate, 8% ethyl palmitate) and 368g glycerine (mol ratio is about 1:4) and 6.7g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the water with respect to 6 times of MAG mole numbers in the oil phase that recovery obtains, direactive glyceride lipase bMGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, (reacting initial temperature is 60 ℃ to programmed cooling, per hour reduces by 10 ℃, is down to 30 ℃, continue 1 hour at 30 ℃, the hydrolysis reaction product composition sees Table 1 behind the reaction 4h.The hydrolysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid of removing wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
The comparative example 1
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.The oil phase that recovery obtains carries out molecular distillation, separates the lipid acid remove wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
The comparative example 2
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.The oil phase that recovery obtains carries out molecular distillation, separates the lipid acid remove wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 170 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
The comparative example 3
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the water with respect to 2 times of MAG mole numbers in the oil phase that recovery obtains, direactive glyceride lipase bMGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, the control temperature of reaction is 60 ℃, reaction 24h, the hydrolysis reaction product composition sees Table 1.The hydrolysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid of removing wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
The comparative example 4
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the water with respect to 6 times of MAG mole numbers in the oil phase that recovery obtains, direactive glyceride lipase bMGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, the control temperature of reaction is 60 ℃ of constant temperature, and the hydrolysis reaction product composition sees Table 1 behind the reaction 4h.The hydrolysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid of removing wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
The comparative example 5
(lipid acid consists of: 80% oleic acid to get 285g oleic acid, 10% linolic acid, 2% stearic acid, 8% palmitinic acid) and 368g glycerine (mol ratio is about 1:4) and 6.5g distilled water, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the constant temperature blender with magnetic force of 400rpm, adds the partial glyceride lipase LipaseSMG1 based on reaction mixture total mass 240U/g, and the control temperature of reaction is 25 ℃; Behind the reaction 24h, the esterification products mixture is carried out centrifugation, reclaim upper oil phase, product composition sees Table 1.Add the water with respect to 6 times of MAG mole numbers in the oil phase that recovery obtains, direactive glyceride lipase bMGL based on reaction mixture total mass 200U/g, pack into and mix in the tool plug triangular flask, and to place rotating speed be to react on the magnetic stirring apparatus of 400rpm, the control temperature of reaction is 30 ℃ of constant temperature, and the hydrolysis reaction product composition sees Table 1 behind the reaction 24h.The hydrolysis reaction product is centrifugal to carry out molecular distillation afterwards to upper oil phase, separates the lipid acid of removing wherein and obtains product take triglyceride as main component.The main operating parameters of molecular distillation is 130 ℃ of vaporization temperatures, and vacuum pressure is 10Pa, and the DAG content behind the molecular distillation in the product sees Table 1.
Table 1
Claims (10)
1. the preparation method of a high purity of diglycerides is characterized in that, may further comprise the steps:
1) utilizes the synthetic mixture that contains triglyceride and direactive glyceride of partial glyceride lipase catalysis lipid acid donor and glycerine reaction, said mixture is carried out centrifugation, reclaim upper oil phase;
2) utilizing the lipase-catalyzed step 1 of direactive glyceride) direactive glyceride and hydroxyl in the oil phase that obtains change into nonglyceride for precursor reactant;
3) with step 2) in the mixture that obtains the nonglyceride composition separate with triglyceride, obtain highly purified triglyceride.
2. preparation method according to claim 1 is characterized in that, the lipid acid donor described in the step 1) is one or more the mixture in lipid acid, lipid acid low-carbon alkyl or the raw material that contains lipid acid, lipid acid low-carbon alkyl; Step 2) donor of hydroxyl described in is one or both the mixture in water and the short chain alcohol.
3. preparation method according to claim 2 is characterized in that, described lipid acid is for having one or more the mixture in the lipid acid of 6 ~ 22 carbon atoms.
4. preparation method according to claim 2 is characterized in that, described lipid acid low-carbon alkyl is one or both the mixture in methyl esters, ethyl ester, propyl ester, butyl ester, the pentyl ester.
5. preparation method according to claim 2 is characterized in that, the mixture of one or more in described short chain alcohol methyl alcohol, ethanol, propyl alcohol, butanols, the amylalcohol.
6. according to claim 1 and 2 or 3 or 4 or 5 described preparation methods, it is characterized in that, adopt the method for programmed cooling, with step 2) in the temperature of enzyme reaction to be controlled at the fusing point of direactive glyceride mixture interval.
7. preparation method according to claim 6 is characterized in that, the method for described programmed cooling is down to 30 ℃ and is continued 1 hour for per hour reducing by 5 ~ 10 ℃.
8. according to claim 1 and 2 or 3 or 4 or 5 described preparation methods, it is characterized in that the mol ratio 1:(0.3 of the donor of lipid acid described in the step 1) and glycerine ~ 4); The mol ratio 1:(4 of direactive glyceride step 2) and hydroxyl donor ~ 10).
9. according to claim 1 and 2 or 3 or 4 or 5 described preparation methods, it is characterized in that the addition of described partial glyceride lipase is based on step 1) reaction mixture total mass 120 ~ 240U/g; The addition of described direactive glyceride lipase is based on step 2) reaction mixture total mass 100 ~ 200U/g.
10. according to claim 1 and 2 or 3 or 4 or 5 described preparation methods, it is characterized in that the partial glyceride lipase described in the step 1) is one or both among LipaseSMG1, the LipaseG50; Step 2) the direactive glyceride lipase described in is one or both among direactive glyceride lipase MGL, the direactive glyceride lipase bMGL.
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| CN110951796A (en) * | 2019-12-31 | 2020-04-03 | 华南理工大学 | Method for converting fatty acid ethyl ester into diglyceride |
| CN111996218A (en) * | 2020-08-31 | 2020-11-27 | 陕西科技大学 | Method for preparing diglyceride by enzyme method |
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| CN114920642A (en) * | 2022-06-02 | 2022-08-19 | 浙江工业大学 | Separation process for obtaining high-purity fatty acid monoglyceride and fatty acid diglyceride |
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| CN103060086B (en) * | 2012-12-17 | 2014-10-08 | 华南理工大学 | Method for removing metaglyceride from grease |
| CN103060086A (en) * | 2012-12-17 | 2013-04-24 | 华南理工大学 | Method for removing metaglyceride from grease |
| CN103627685A (en) * | 2013-11-20 | 2014-03-12 | 华南理工大学 | Higher-activity partial glyceride lipase mutant and application thereof |
| CN103627685B (en) * | 2013-11-20 | 2015-07-01 | 华南理工大学 | Higher-activity partial glyceride lipase mutant and application thereof |
| CN112513235B (en) * | 2018-06-05 | 2023-12-01 | 帝斯曼知识产权资产管理有限公司 | Process for producing diglyceride |
| CN112513235A (en) * | 2018-06-05 | 2021-03-16 | 帝斯曼知识产权资产管理有限公司 | Process for producing diglycerides |
| WO2020244315A1 (en) * | 2019-06-06 | 2020-12-10 | 广东省农业科学院蚕业与农产品加工研究所 | Glyceride mixture rich in polyunsaturated fatty acids, preparation method therefor and application thereof |
| CN110777170A (en) * | 2019-11-06 | 2020-02-11 | 华南理工大学 | Method for synthesizing diglyceride |
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