CN104830920B - A kind of production method of diglyceride - Google Patents
A kind of production method of diglyceride Download PDFInfo
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
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Abstract
The invention discloses a kind of production methods of diglyceride, comprising the following steps: (1) glycerolysis reaction is carried out in container I to grease using lipase；(2) step (1) reactants separate glycerol is mutually transported in container II with the oil after lipase, the temperature of grease is 60~150 DEG C in container II, residence time of the grease in container II is 1~12hr, then it is cooled to the temperature of glycerolysis reaction, it is back in container I, glycerol and lipase are added, the glycerolysis reaction of step (1) is continued；(3) above-mentioned reaction is repeated, so that 1~10 circulation occurs for grease, obtains the reaction product rich in diglyceride.The present invention carries out configuration conversion to the diglyceride in reaction product by the method for heating or chemical catalysis, to obtain the higher reaction product of diacylglycerol content.The method increase diglyceride conversion ratio, and it is easily operated.
Description
Technical field
The present invention relates to a kind of production technologies of diglyceride, which uses glycerol rhizolomy method, by reaction product
Alternating temperature make the transition operation, improve diglyceride conversion ratio, and easily operated.
Background technique
Diglyceride is a kind of fat molecule only having there are two fatty acid chain, and diglyceride can be used as emulsifier, fat
Plasticity modifier or matrix as food, drug, cosmetics etc..In recent years the study found that diglyceride and triglycerides
Absorption And Metabolism mode it is different, diglyceride has the characteristics that be easier to be converted to energy and utilize in vivo, and glycerol three
Ester is then easier to put aside in vivo.The edible grease containing diglyceride has the effect of inhibiting weight gain, therefore, glycerol two
It is edible that ester oil rouge can be used as a kind of healthy grease.
Diglyceride can be produced by kinds of processes, and related fields has had that many patents disclose corresponding producers
Method, as CN988083043C, CN028270940C, CN031138624C, CN200310112327C, CN200810205018C,
CN2004100153484C、CN2005101350520C、CN2006100357438C、CN2006100492425C、
CN2006100681944C, CN2007100302730C and CN2008801023446C etc..But most methods do not enter into work
Industry application.Currently, representative industry application method thereof is first by grease hydrolysis at fatty acid, then by lipase and glycerol 1,3
Synthetic triglyceride under the catalysis of position specific lipase.The process requirement is related to the hydrolysis of grease and the esterification of fatty acid.It is many
Well known, the enzymatic hydrolysis reaction of grease is not thorough, and generally to use the chemical hydrolysis of high temperature and pressure, energy consumption is high and exists secondary
React occurrence risk.And in the enzymatic clarification of diglyceride, the esterification of fatty acid and glycerol has been selected, esterification
Efficiency is not generally high, moreover, still containing a large amount of unreacted free fatty acids and monoglyceride pair in the reaction product after esterification
The separation removal of product, these by-products will spend cost.In spite of above-mentioned various shortcoming, people still use the technique to carry out
The production of diglyceride product, because the advantages of above-mentioned reaction being the diglyceride product that can obtain 80%.
Diglyceride can also be produced by glycerol rhizolomy technique, and glycerolysis reaction refers to the grease and glycerol of triglyceride type
Between reaction.It can be appreciated that glycerolysis reaction process is simple, it appears that be a kind of more preferably reaction method.However, to grease
Glycerolysis reaction is studies have shown that in solvent-free system, and diacylglycerol content is not high in enzyme process glycerolysis reaction product, also
It is that grease has that conversion rate is not high when glycerol rhizolomy produces diglyceride.
Summary of the invention
The present invention in view of the deficiencies of the prior art, it is sweet to develop a kind of grease enzyme process with more two ester conversion rate of high glycerine
Oily solution technique.
For convenience of statement, it is diglyceride index that we, which define diglyceride/(diglyceride+triglycerides), below, should
Index is the ratio of diglyceride and diglyceride total amount in the amount and reaction product of diglyceride in reaction product.Because in life
When producing diglyceride product, the substances such as monoglyceride, fatty acid for including in reaction product are intended to remove, and residue is mainly glycerol
The mixture of diester and triglycerides, the mixture are exactly our obtained diglyceride products.It follows that diglyceride
Index represents the substantially content of reaction product diglyceride in final finished after separation processing, improves the sweet of reaction
Oily diester index has very important significance for the production of diglyceride.Usual enzyme process glycerolysis reaction reaches sweet when balance
The ratio of oily diester index is usually no more than 0.55, moreover, diglyceride index is frequently present of fluctuation.Refer to finding diglyceride
When number cause of fluctuation, this seminar analyzes reaction product, finds to mainly generate 1,2- glycerol when enzyme process glycerolysis reaction
The production quantity of diester and 2,3- diglyceride, 1,3-DAG is very low.Cause this phenomenon related with the catalysis specificity of enzyme.
Lipase is often divided into 1,3 specific rouge according to the catalysis specificity to glyceride positions, people by lipase
Fat enzyme and nonspecific lipid enzyme are described lipase in this way in many documents.Ironically, we are carrying out glycerol
All lipase tested when solution reaction show 1,3 specificity, and complete non-specific lipase is not yet found at present, no
With the only difference of specific size between enzyme.We are solved with enzyme process glycerol rhizolomy of the catalytic selectivity phenomenon of enzyme to grease
It releases, is just readily appreciated that and mainly generates 1,2- diglyceride and 2 when why reacting, 3- diglyceride.Because lipase is all
More or less 1 or 3 fatty acid of preferential selection triglycerides is catalyzed, these fatty acid are transferred on glycerol,
Triglycerides is then become to non-1,3-DAG, glycerol combines fatty acid and primarily become monoglyceride and 1,3- glycerol two
Ester.By analyzing above, we can glycerolysis reaction process to grease carry out following finer description:
It is well known that the concentration of substance will affect reaction balance on the right of reaction equation.But in equation 1, equation
The 1,3-DAG on the right is mainly derived from 1,2- diglyceride and 2, the chemical conversion of 3- diglyceride, inhibit reaction to
Whether can 1,3-DAG be equal to 1,2- diglyceride and 2,3- diglyceride in the contribution moved right? studies have shown that
Answer is negative.1,3- diglyceride is less than non-1,3- diglyceride for the influence for inhibiting reaction to carry out to the right.
The above research, can explain why diglyceride index often fluctuates.This may exist with 1,3- diacylglycerol content
The fluctuation of proportion is related in diglyceride total amount, experiments have shown that 1,3-DAG accounts for always in enzyme process glycerolysis reaction product
30~50% or so of diacylglycerol content.
It has been reported that 1,3-DAG and non-1,3-DAG be there is thermodynamical equilibrium, when balance, 1,3- glycerol
Diester accounts for 70% of total triglyceride or so.Obviously, thermodynamics has not yet been reached in the enzyme process glycerolysis reaction product under usual conditions
Equilibrium state, we can generate the method for higher 1,3-DAG by certain technology to improve diglyceride index.Base
In principles above, this seminar develops a kind of diglyceride production method of high conversion, method includes the following steps:
(1) glycerolysis reaction is carried out to grease in container I using lipase；
(2) step (1) reactants separate glycerol is mutually transported in container II with the oil after lipase, grease in container II
Temperature be 60~150 DEG C, residence time of the grease in container II be 1~12hr, be then cooled to the temperature of glycerolysis reaction
Degree, is back in container I, adds glycerol and lipase, continues the glycerolysis reaction of step (1)；
(3) above-mentioned reaction is repeated, so that 1~10 circulation occurs for grease, obtains the reaction product rich in diglyceride.
The first step of the method for the present invention is lipase-catalyzed glycerolysis reaction.As previously mentioned, the glycerolysis reaction of grease
Product is monoglyceride and a variety of diglycerides.The grease of all triglyceride types can carry out glycerol rhizolomy method production glycerol two
Ester, such as rapeseed oil, soybean oil, palm oil, sunflower oil, corn oil, peanut oil, camellia oil, olive oil, rice bran oil and cottonseed oil
Deng.Lipase, that is, Lipase, it is catalyzed natural substrate grease hydrolysis, generates fatty acid, glycerol and glycerol
Monoesters or diester.Lipase be from one of root enzyme category, aspergillus, hair enzyme category, bacterium, saccharomycete, animal pancreas or
More than one mixture.The dosage of lipase determines reaction speed, and the glycerolysis reaction of grease has lot of documents report,
The enzyme concentration being referred in document, as lipase additive amount can choose as 5~100IU/g grease.Point about enzyme activity
Analysis, using potentiometric titration, with reference to national standard GB/T 23535-2009.Lipase activity does substrate using emulsification olive oil.Enzyme process
The reaction temperature of glycerol rhizolomy it is different according to the kind of enzyme and can difference, generally select 30~50 DEG C, temperature is too low, reaction speed
Degree is slow, and temperature is excessively high, is unfavorable for the stability of enzyme.
Glycerolysis reaction can occur in the presence of water, can also it is anhydrous under the conditions of occur.Generally there is water bar
Under part, glycerolysis reaction speed will more faster, and the amount of water of glycerol rhizolomy can have very wide range, such as selection oil quantity
0.1~100%, still, too low amount of water is little to the increase rate of reaction speed, and it is secondary that excessively high amount of water will lead to hydrolysis
Reaction aggravation.Comprehensively consider, selects the 0.5~3% of the grease weight requirement for being more conform with most production applications as amount of water.
Glycerolysis reaction is general technology, which kind of glycerol rhizolomy condition not to be main points of the invention using.
The purpose of second step of the present invention be diglyceride in enzyme process glycerolysis reaction product is made the transition, as previously mentioned,
1,3-DAG is weaker to the inhibiting effect of glycerolysis reaction, it is intended that non-1,3-DAG is converted 1,3- glycerol
Diester.One of the method for carrying out the conversion most convenient is exactly to improve temperature, and transition carries out in container II.Studies have shown that high temperature
Be conducive to diglyceride and reach chemical balance, but also will increase energy consumption and increase Oxidation of Fat and Oils risk, diglyceride in the present invention
Transition temperature takes 60~150 DEG C, preferably 70~100 DEG C.The transition of diglyceride is also positively correlated with the time, and it is advantageous to extend the time
In its transition, the present invention, limiting grease, the residence time, the residence time was when representing transition as 1~12hr in container II
Between.Be readily appreciated that, grease, which is transferred to container II from container I, can be batch-type, be also possible to it is continuous, no matter which kind of grasp
Make form, the diglyceride in reaction product can be made to be made the transition in effect.Since temperature is between container I and II
It is different, when grease is back to container I from container II, temperature adjusting can be related to, temperature adjusting can occur grease from
When container II comes out, it can also occur in container I.In the present invention, grease enzyme process glycerolysis reaction needs specific reaction item
Part, as enzymatic reaction system, temp regulating function is basic function, and no longer temperature regulation mechanism etc. is specifically described herein
And restriction.
Carry out the conversion of diglyceride configuration another way be using chemical catalyst be catalyzed, studies have shown that solid acid,
The substance of the acidity active group such as acid-exchange resin and carclazyte can promote the configuration of diglyceride to convert, still,
From easy to operate angle, it is preferable to use acid-exchange resin and solid acid.When this method is employed, corresponding operation side
Method becomes:
(1) glycerolysis reaction is carried out in containment system to grease using lipase；
(2) by step (1) reactants separate glycerol and lipase, glycerol and enzyme return step (1) container, oil is mutually and solid
Catalyst is back in step (1) container after contacting 10~120min, continues the reaction of step (1)；
(3) above-mentioned reaction is repeated, so that 1~10 circulation occurs for grease, obtains the reaction product rich in diglyceride.
Third step of the present invention is to repeat the operation of the first step and second step, so that multiple circulation has occurred in grease.Herein, one
The connotation of secondary circulation, which refers to have, has occurred primary disengaging in container I with the grease of volume same in reactant.It is clear that circulation
Number is more, and the smaller but excessive cycle-index of the component difference between container I and container II will increase operating cost, the present invention
In with 1~10 time circulation for appropriateness.By operating above, so that it may obtain the reaction product rich in diglyceride, product has
Higher diglyceride index.In addition, the present invention is for the purpose of producing diglyceride product, if to be processed into adaptable
Product, reaction product will be by separation toward contact.The purpose of product separation is to separate low-boiling point material, these low-boiling point materials
Including monoglyceride and fatty acid.Molecular distillation method is usually used in isolated method, for the general side of diglyceride production
Method.By separation, the product rich in diglyceride is obtained.
Compared with prior art, the present invention has the advantage that
(1) present invention uses enzyme process glycerol rhizolomy method, by the method for heating or chemical catalysis in reaction product
Diglyceride carries out configuration conversion, promotes reaction and moves right, so that the higher reaction product of diacylglycerol content is obtained, it is sweet
Oily diester index is improved to 0.60 or more, the method increase the conversion ratio of diglyceride, and also it is easily operated.
(2) traditional solvent-free system glycerolysis reaction method generally requires 30h or more, and due to the feedback inhibition of product
Effect, diglyceride index is generally not more than 0 when reaction reaches balance.55.And the present invention can improve diglyceride index
To 0.60 or more, therefore, faster, conversion ratio is higher for reaction rate of the invention.
Specific embodiment
Embodiment 1
Canola rapeseed oil 500g is added the glycerol of grease 10% and 0.5% water, then presses as in boiling flask I
Lipozyme RM liquid enzymes (Novozymes Products) are added according to 5IU/g grease, magnetic stirrer reaction,
Reaction temperature control is 30 DEG C.After reacting 3hr, the reactant in flask I is centrifugated, upper layer is grease, lower layer be glycerol,
The mixture of lipase and water.The oil for reacting upper layer is mutually warming up to 60 DEG C, is placed in flask II after keeping the temperature 3hr the return that cools down again
In flask I, it is added the mixture of glycerol, enzyme and water that previous step is centrifugally separating to obtain the reaction was continued 3hr.It is repeated 10 times above-mentioned incite somebody to action
Grease is transferred to the operation that flask II returns again to flask I from flask I, and the grease for being equivalent to all participation reactions has occurred 10 times and follows
Ring obtains reaction product, and the diglyceride index for measuring reaction product is 0.57.
Embodiment 2
10% glycerol of grease and 3% water is added as in round-bottomed flask I in Canola rapeseed oil 500g, then according to
Lipozyme RM liquid enzymes (Novozymes Products) are added in 100IU/g grease, are stirred to react, reaction temperature is
40℃.After reacting 3hr, 56g (10% reactant) is taken to be centrifugated from reaction system, upper layer is grease, and lower layer is aqueous glycerol
With the mixture of enzyme.The oil that upper layer will be reacted mutually is warming up to 150 DEG C, is placed in flask II after heat preservation 1hr to cool down again and returns to flask I
In, it is added the mixture of aqueous glycerol and enzyme that previous step is centrifugally separating to obtain the reaction was continued 3hr.It is repeated 10 times above-mentioned by grease
It is transferred to the operation that flask II returns again to flask I from flask I, the grease for all participating in reacting is equivalent to and 1 circulation has occurred, obtain
To reaction product, the diglyceride index for measuring reaction product is 0.59.
Embodiment 3
As in boiling flask I 10% glycerol of grease and 1% water is added, then according to 50IU/ in Canola rapeseed oil 500g
Lipozyme RM liquid enzymes (Novozymes Products) are added in g grease, magnetic stirrer reaction, reaction temperature
Degree control is 45 DEG C.After reacting 3hr, the reactant in flask I is centrifugated, upper layer is grease, and lower layer is glycerol, enzyme and water
Mixture.The oil that upper layer will be reacted mutually is warming up to 100 DEG C, is placed in flask II after heat preservation 12hr to cool down again and returns in flask I,
It is added the mixture of glycerol, enzyme and water that previous step is centrifugally separating to obtain the reaction was continued 3hr.Be repeated 3 times it is above-mentioned by grease from burning
Bottle I is transferred to the operation that flask II returns again to flask I, is equivalent to the grease for all participating in reacting and 3 circulations have occurred, obtain anti-
Product is answered, the diglyceride index for measuring reaction product is 0.64.
Embodiment 4
As in boiling flask I 10% glycerol of grease and 1% water is added, then according to 50IU/ in Canola rapeseed oil 500g
Lipozyme RM liquid enzymes (Novozymes Products) are added in g grease, magnetic stirrer reaction, reaction temperature
Degree control is 50 DEG C.After reacting 5hr, the reactant in flask I is centrifugated, upper layer is grease, and lower layer is glycerol, enzyme and water
Mixture.The oil that upper layer will be reacted mutually is warming up to 70 DEG C, is placed in flask II after heat preservation 6hr to cool down again and returns in flask I, adds
Enter mixture the reaction was continued the 5hr of glycerol, enzyme and water that previous step is centrifugally separating to obtain.Be repeated 5 times it is above-mentioned by grease from flask I
It is transferred to the operation that flask II returns again to flask I, the grease for all participating in reacting is equivalent to and 5 circulations has occurred, reacted
Product, the diglyceride index for measuring reaction product is 0.65.
Embodiment 5
As in boiling flask I 10% glycerol of grease and 1% water is added, then according to 30IU/ in Canola rapeseed oil 500g
Lipozyme RM liquid enzymes (Novozymes Products) are added in g grease, magnetic stirrer reaction, reaction temperature
Degree control is 40 DEG C.After reacting 5hr, the reactant in flask I is centrifugated, upper layer is grease, and lower layer is glycerol, enzyme and water
Mixture.The oil that upper layer will be reacted mutually is warming up to 90 DEG C, is placed in flask II after heat preservation 6hr to cool down again and returns in flask I, adds
Enter mixture the reaction was continued the 5hr of glycerol, enzyme and water that previous step is centrifugally separating to obtain.Be repeated 5 times it is above-mentioned by grease from flask I
It is transferred to the operation that flask II returns again to flask I, the grease for all participating in reacting is equivalent to and 5 circulations has occurred, reacted
Product, the diglyceride index for measuring reaction product is 0.67.
Embodiment 6
As in boiling flask 10% glycerol of grease and 1% water is added, then according to 30IU/g in Canola rapeseed oil 500g
Lipozyme RM liquid enzymes (Novozymes Products) are added in grease, magnetic stirrer reaction, reaction temperature
Degree control is 40 DEG C.After reacting 5hr, the reactant in boiling flask is centrifugated, upper layer is grease, and lower layer is glycerol, enzyme
With the mixture of water.The oil for reacting upper layer is mutually conveyed with peristaltic pump by being filled with ion exchange resin AMBERLITE
Return again to boiling flask after the packed bed of FPC22 (Rohm&Hass company), the average contact time 120min of grease and resin,
It is added the mixture of glycerol, enzyme and water that previous step is centrifugally separating to obtain in flask the reaction was continued 5hr.It is equivalent to and all participates in instead
1 circulation has occurred in the grease answered, and obtains reaction product, and the diglyceride index for measuring reaction product is 0.60.
Embodiment 7
As in boiling flask 10% glycerol of grease and 1% water is added, then according to 30IU/g in Canola rapeseed oil 500g
Lipozyme RM liquid enzymes (Novozymes Products) are added in grease, magnetic stirrer reaction, reaction temperature
Degree control is 40 DEG C.After reacting 5hr, the reactant in boiling flask is centrifugated, upper layer is grease, and lower layer is glycerol, enzyme
With the mixture of water.By react upper layer oil mutually with peristaltic pump conveying by be filled with solid acid (solid acid preparation method:
ZrOCl2It is dissolved in distilled water, with concentrated ammonia liquor tune PH to 10.0, centrifugation is washed repeatedly repeatedly with distilled water, dry 3hr at 120 DEG C,
Then the H of 1mol/L is used2SO4Solution dipping r for 24 hours, centrifugation, with being returned again after the packed bed of 600 DEG C of Muffle furnace roasting 3hr) after drying
Return boiling flask, the average contact time of grease and solid acid is 10min, be added in flask previous step be centrifugally separating to obtain it is sweet
Mixture the reaction was continued the 5hr of oil, enzyme and water.Aforesaid operations are repeated 10 times, the grease for all participating in reacting is equivalent to and has occurred
10 circulations, obtain reaction product, and the diglyceride index for measuring reaction product is 0.61.
Comparative example 1
As in boiling flask I 10% glycerol of grease and 1% water is added, then according to 30IU/ in Canola rapeseed oil 500g
Lipozyme RM liquid enzymes (Novozymes Products) are added in g grease, magnetic stirrer reaction, reaction temperature
Degree control is 40 DEG C.After reacting 30hr, reaction product is obtained, the diglyceride index for measuring reaction product is 0.53.
Comparative example 2
10% glycerol of grease and 1% water is added as in boiling flask I in Canola rapeseed oil 500g, then according to
Lipozyme RM liquid enzymes (Novozymes Products) are added in 100IU/g grease, magnetic stirrer reaction,
Reaction temperature control is 40 DEG C.After reacting 30hr, reaction product is obtained, the diglyceride index for measuring reaction product is 0.55.
According to Examples 1 to 5 result as it can be seen that diglyceride index is lower than 0.6 only in Examples 1 and 2, but it is higher than
0.55, other reactions are above 0.6, thus it is speculated that 1 diglyceride index of embodiment is low low with enzyme concentration related.From Examples 1 to 5 and
Comparative example 1~2 compares, and the diglyceride index for obtaining reaction product using the method for the present invention is higher.Embodiment 5 and right
Glycerolysis reaction than embodiment 1 is to carry out under the same conditions, primary difference is that the product of 5 reaction process of embodiment passes through
In the isothermal holding of flask II, the results showed that the diglyceride index of embodiment 5 is significantly higher than comparative example 1, illustrates anti-
It answers transition of the product in flask II to be conducive to reaction to carry out to the right.According to embodiment 6~7 and comparative example 1~2 as a result,
As it can be seen that carrying out configuration conversion to catalysate using solid acid also has the effect of improving diglyceride index in reaction product.
Comparative example 1 and comparative example 2 compare influence of the enzyme concentration to diglyceride index in reaction product, the results showed that,
Under the conditions of selected enzyme concentration, diglyceride index variation is little, shows that existing enzyme concentration is enough, increases enzyme
Diglyceride index substantially 0.55 when measuring no longer valid, also illustrate that above-mentioned reaction has had reached balance, and reaching balance
Within.
Claims (7)
1. a kind of production method of diglyceride, which comprises the following steps:
(1) glycerolysis reaction is carried out in container I using Lipozyme RM catalysis grease and glycerol；
(2) step (1) reactants separate glycerol is mutually transported in container II with the oil after lipase, the temperature of grease in container II
Degree is 60~150 DEG C, and residence time of the grease in container II is 1~12hr, is then cooled to the temperature of glycerolysis reaction, returns
It is back in container I, adds glycerol and lipase, continue the glycerolysis reaction of step (1)；
(3) above-mentioned reaction is repeated, so that 1~10 circulation occurs for grease, obtains the reaction product rich in diglyceride.
2. the method according to claim 1, wherein the temperature of grease is 70~100 DEG C in the container II.
3. method according to claim 1 or 2, which is characterized in that step (1) described glycerolysis reaction is in the condition for having water
Lower generation, amount of water are the 0.5~3% of grease weight；The temperature of the glycerolysis reaction is 30~50 DEG C.
4. method according to claim 1 or 2, which is characterized in that the additive amount of the lipase is 5~100IU/g oil
Rouge.
5. method according to claim 1 or 2, which is characterized in that residence time of the grease in container II be 6~
12hr。
6. a kind of production method of diglyceride, which comprises the following steps:
(1) glycerolysis reaction is carried out using Lipozyme RM catalysis grease and glycerol in a reservoir；
(2) by step (1) reactants separate glycerol and lipase, the container of glycerol and lipase return step (1) is oily mutually and solid
Body catalyst is back in step (1) container after contacting 10~120min, continues the reaction of step (1)；The solid catalysis
Agent is the mixture of one or both of acid-exchange resin, solid acid；
(3) above-mentioned reaction is repeated, so that 1~10 circulation occurs for grease, obtains the reaction product rich in diglyceride.
7. according to the method described in claim 6, it is characterized in that, step (1) described glycerolysis reaction in the presence of water
Occur, amount of water is the 0.5~3% of grease weight, and the temperature of glycerolysis reaction is 30~50 DEG C.
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| CN105639118A (en) * | 2015-12-30 | 2016-06-08 | 北京资源亚太饲料科技有限公司 | Compound fat and preparation method thereof |
| CN106148439A (en) * | 2016-09-08 | 2016-11-23 | 东北农业大学 | A kind of method that power ultrasonic pretreatment enzyme law catalysis Adeps Sus domestica glycerol rhizolomy prepares diglyceride |
| CN108676786B (en) * | 2018-05-31 | 2021-02-23 | 大连民族大学 | Culture medium for producing lipase by fermenting torticola terricola and culture method thereof |
| CN112322670B (en) * | 2020-11-06 | 2021-10-15 | 华南理工大学 | Method for synthesizing diglyceride |
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