CN109055447A - A kind of supercritical CO2The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides - Google Patents
A kind of supercritical CO2The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides Download PDFInfo
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- CN109055447A CN109055447A CN201810985475.9A CN201810985475A CN109055447A CN 109055447 A CN109055447 A CN 109055447A CN 201810985475 A CN201810985475 A CN 201810985475A CN 109055447 A CN109055447 A CN 109055447A
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- 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
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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Abstract
The invention belongs to biocatalysis technology fields, are related to a kind of supercritical CO2The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides.The method that immobilized enzyme catalysis of the present invention prepares 1,3 diglycerides specifically: imidazoles dressing agent and N,N'-carbonyldiimidazole are added in anhydrous dimethyl sulfoxide, magnetic agitation；Active body is added in fatty enzyme solution, the lipase after being modified is reacted；Zinc nitrate is add to deionized water；By after 2-methylimidazole, modification lipase and polyvinylpyrrolidone be dissolved in deionized water；Above-mentioned solution is mixed, immobilized lipase is obtained；Fatty acid is mixed with glycerol, obtains reactant, immobilized lipase is added, is placed in reaction kettle, CO is added2Medium obtains 1,3 diglycerides.Reaction condition of the invention is mild, easy to operate, and raw material availability is high, high conversion rate, purity is high, and enzyme catalyst is reusable, and selectivity is high, and environmental pollution is small, and production cost is low, is expected to carry out industrialized production.
Description
Technical field
The invention belongs to biocatalysis technology fields, are related to a kind of supercritical CO2Technique immobilized enzyme catalysis preparation 1,3
The method of diglyceride.
Background technique
With the improvement of people ' s living standards, the formation of bad life habits, obesity, cardiovascular disease, fatty liver etc.
Rich people's disease is more and more common, has seriously threatened the health of the mankind at present.1,3 diglyceride can not only improve flavour of food products, extend
Storage period, and be the main additive of functional food, it can be reduced intracorporal fat accumulation, prevent and treat hyperlipidemia and correlation
Disease.1,3 diglyceride is the natural component of grease, is the intermediate product of fat metabolic.1,3 diglyceride is highly-safe,
U.S. FDA certification is passed through, has been the food composition of " universally acknowledged safety (GRAS) ".In conclusion 1,3 diglycerides of preparation
Very necessary, and select a kind of mode of green high-efficient prepare 1,3 diglycerides be again one very it is worth we explore with
The project of research.
Substrate glycerol and fatty acid acid in current 1,3 diglyceride preparation process be not lipase in nature
Natural substrate, organic solvent system are also not lipase-catalyzed natural surroundings, significantly limit lipase selectivity and
Activity expression causes 1,3 diglyceride yields generally relatively low, and a large amount of use of organic solvent is not only polluted in current process
Environment has great security risk simultaneously for fatty foods.
There are much patents in terms of preparing 1,3 diglycerides at present.Such as related patents report is a kind of
Using graphene immobilized lipase, it is catalyzed the method that grease reaction generates 1,3 diglycerides, belongs to food chemistry technology neck
Domain.This method carries out as follows: (1) being placed in free-fat enzyme solutions in the phosphate buffer solution that pH is 8.0, quality point
Number is 5%~50%, collects upper layer enzyme solutions, and the graphene oxide based on free-fat enzyme quality 30%~200%, control is added
Temperature processed is 45 DEG C, and isothermal vibration adsorbs 6~12h, and filtering is rinsed until no albumen washes out with phosphate buffer solution, is made
Graphene immobilized lipase；(2) grease and graphene immobilized lipase based on oil quality 1~20% are placed in and are suitable for
Be uniformly mixed in any biochemical device of enzyme reaction, being placed in revolving speed is under 500r/min in constant temperature oscillator, temperature control 30~
65 DEG C, 1~10h is reacted, reaction product is obtained；(3) immobilized lipase is recycled, gained reaction product in step (2) is steamed
Purifying is evaporated, 1,3 diglycerides are made.This method can be easily separated with catalyst, realize recyclable advantage, but grease is made
For reaction substrate, realizes that grease 2- hydrolysing activity is low, be unfavorable for industrialized production.
The production method for 1,3 diglycerides that related patents illustrate is: being carried out in container I using lipase to grease sweet
Oil solution reaction；Then 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 glycerolysis reaction；Above-mentioned reaction is repeated, so that grease occurs 1~10
Secondary circulation obtains the reaction product rich in 1,3 diglycerides.The invention produces reaction by the method for heating or chemical catalysis
1 in object, 3 diglycerides carry out configuration conversion, so that 1 is obtained, the higher reaction product of 3 diacylglycerol contents.This method mentions
High 1,3 diglyceride conversion ratios, and it is easily operated, but free lipase is unfavorable for serialization in industry and quickly produces.
Related patents are related to the preparation method of 1,3-DAG pork fat, and the invention is by pork fat, glycerol and lipase
Concussion reaction is catalyzed in a mild condition using enzyme and generates 1,3-DAG；It is centrifugated at normal temperature, discards glycerol and rouge
Fat enzyme obtains the pork fat rich in 1,3-DAG；Wherein triglycerides be converted into the amount of 1,3- diglyceride 44% with
On, this method reaction condition is mild, but the reaction time is longer, and the glycerol that solvent carries out reinforcing mass transfer, therefore reaches is not added
Diester yield is relatively low.White solid-state under pork fat room temperature rich in 1,3- diglyceride；The more common pork fat of fusing point is slightly higher,
Between 36 DEG C~48 DEG C.Pork fat rich in 1,3-DAG maintains the distinctive fragrance of pork fat itself and mouthfeel, makees
For a kind of prevention and improvement obesity, hyperlipemia and the new type functional grease for inhibiting diabetes abnormal metabolism, it is rich in 1,
The pork fat of 3- diglyceride can be used for modulating the nutritious food of special population, and it is a variety of to can be used for meat products, bakery product, moon cake etc.
Food industry ingredient, also can be used for conventional culinary.
Summary of the invention
It is an object of the invention to overcome technological deficiency existing in the prior art, such as: yield is lower, and the reaction time is long,
The problems such as lipase active is low and cannot reuse, the present invention provide a kind of new side of 1,3 diglycerides of green high-efficient preparation
Method, especially a kind of supercritical CO2The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides.
Specifically, the technical solution adopted by the present invention is that:
(1) lipase is modified:
Imidazoles dressing agent and N,N'-carbonyldiimidazole are added in anhydrous dimethyl sulfoxide, magnetic agitation, room temperature reaction obtains activity
Body；Active body is added in fatty enzyme solution, magnetic agitation reaction, dialysis, the lipase after being modified；
(2) immobilized lipase is prepared:
Zinc nitrate is add to deionized water, solution A is obtained；By the lipase and polyethylene pyrrole after 2-methylimidazole, modification
Pyrrolidone (PVP) is dissolved in deionized water, obtains solution B；Solution A is mixed with solution B, is stirred, centrifugation, washing obtain
Immobilized lipase；
(3) 1,3 diglycerides are prepared:
Fatty acid is mixed with glycerol, obtains reactant, immobilized lipase is added, is placed in reaction kettle, CO is added2Medium, instead
It answers, filters, obtain 1,3 diglycerides.
In step (1), the molar ratio of the imidazoles dressing agent and N,N'-carbonyldiimidazole is 1:1；The imidazoles dressing agent is
2- methyl 4- carboxylic acid imidazoles or 2- methyl 4,5- dicarboxylic acid imidazole；The time of the room temperature reaction is 2-10h；The active body with
The volume ratio of fatty enzyme solution is 90 μ L:5-15mL, and the concentration of the lipase is 30-150 μm of ol/L；The temperature of the magnetic agitation
Degree is 0-4 DEG C, and the time of the magnetic agitation is 4-12h；
In step (1), it is described fat enzyme solution in lipase be candida rugosa lipase, antarctic candidia lipase,
Porcine pancreatic lipase, Aspergillus oryzae lipase, lipase from Aspergillus Niger, rice black wool mould bacterium lipase, Pseudomonas cepacia lipase or
One kind of thermus thermophilus lipase；
In step (2), the amount ratio of the zinc nitrate, deionized water and 2-methylimidazole is 10-400mg:1-5mL:
410.0mg；The amount ratio of lipase and polyvinylpyrrolidone after the 2-methylimidazole, modification is 410.0mg:5mL:
50.0mg；The temperature of the dissolution is 42 DEG C；The time of the stirring is 5-10min；
In step (3), the molar ratio of the fatty acid and glycerol is 2:1, and the dosage of immobilized lipase accounts for reaction-ure mixture
0.5-10 wt%；The temperature of the reaction is 20-90 DEG C, and the pressure of the reaction is 5-40MPa, and the time of the reaction is 2-
15 hours；The source of the fatty acid is rapeseed oil, soybean oil, peanut oil, corn oil, castor oil, cottonseed oil, tung oil, Chinese tallow tree
One of oil, fish oil, lard or more than one mixture.
Compared with prior art, beneficial effects of the present invention embody as follows:
(1) general 1,3 diglycerides can by catalysis prepare, enzyme is a kind of biocatalyst, it is advantageous that efficiently, nothing
Malicious and mild reaction condition.Enzyme process prepares 1,3 diglycerides, and key is exactly the selection to enzyme, which needs to have high sweet
Oil solution and low in hydrolysis activity.The present invention focuses on lipase-catalyzed dose using a kind of reaction condition mildly, and lipase is consolidated
It is scheduled on carrier, does not contact noxious material secondly, being resolved into the production processes of 1,3 diglycerides with lipase-catalyzed glycerol,
And immobilized lipase is reusable, is very suitable to the industrial production of 1,3 diglycerides, is a kind of producer of green low-carbon
Formula has utility value.
(2) present invention uses supercritical fluid process, when a kind of fluid is in the temperature and pressure higher than its critical point,
Be referred to as supercritical fluid (SCFs), it not only had with the physical property such as density, viscosity, diffusion coefficient as gas phase, but also have concurrently
It is the substance in the intermediate state between gaseous state and liquid with characteristic similar in liquid.Fluid CO under supercriticality2Simultaneously
Play the role of solvent and catalyst, due to CO2It is nonpolar molecule, can avoid other methods and occur being poisoned and catalyst inactivation
The phenomenon that.In addition, glycerol rhizolomy back reaction can be prevented under the reaction environment, have a good application prospect.
(3) present invention realizes enzymatic under supercritical process and prepares 1,3 diglycerides, and the reaction condition is mild, operation
Simply, raw material availability is high, high conversion rate, purity is high, and enzyme catalyst is reusable, and selectivity is high, environmental pollution
It is small, advantageously reduce production cost.Medium of the supercritical carbon dioxide as enzymic catalytic reaction has many other media can not
The advantages of analogy, can change its own characteristic by simple adjustment temperature, pressure, entrainment agent content, promote substrate trigalloyl sweet
The dissolubility of grease in the reaction system, and spread rapidly, recyclable and regeneration small to the activity influence of enzyme.
Specific embodiment
The present invention is further illustrated combined with specific embodiments below, but protection scope of the present invention is not limited to
This.
Embodiment 1:
(1) lipase is modified:
2- methyl 4- carboxylic acid imidazoles (imidazoles dressing agent), the 1 mmol N,N'-carbonyldiimidazole of 1 mmol is taken to be added to anhydrous the two of 2 mL
In first sulfoxide, magnetic agitation stops after reacting at room temperature 2 h, obtains active body；The active body of 90 μ L is added to 5 mL concentration
In candida rugosa lipase liquid for 150 μm of ol/L, stop reaction after 8 h of magnetic agitation at 0 DEG C, it is anti-by what is obtained
Answer liquid 10KD bag filter 24 h of dialysis, the candida rugosa lipase after being modified.
(2) immobilized lipase is prepared:
It weighs 371.3mg zinc nitrate to be added in 3.0mL deionized water, obtains solution A；(referred to as by 410.0mg 2-methylimidazole
It is dissolved at 42 DEG C for candida rugosa lipase liquid, the 50.0mg polyvinylpyrrolidone PVP after 2-mIm), 5mL modification
In 25mL deionized water, solution B is obtained；Then two kinds of solution A, solution B solution are mixed, are stirred after five minutes,
Immobilised enzymes product is collected by centrifugation in 4800rpm, is washed with excessive deionized water, obtains metal-organic framework materials immobilization
Candida rugosa lipase.
(3) 1,3 diglycerides are prepared:
Fatty acid after peanut oil is hydrolyzed mixes (molar ratio 2:1) with 5g glycerol, obtains reactant, and addition accounts for reactant gross weight
The immobilized lipase of 2.5 wt%, is placed in reaction kettle, and CO is added2Medium, is warming up to 64 DEG C, and control reaction pressure is
10MPa is at supercriticality, and reaction was down to room temperature after 7 hours, and it is normal for slowly releasing carbon dioxide to reactor pressure
Immobilized lipase reuse is recovered by filtration in pressure；Filtering, obtains 1,3 diglyceride of product, product is through high performance liquid chromatography
Analysis, with this condition, the mass fraction for obtaining 1,3 diglycerides in reaction product is 68.6%.Go out by steam treatment
Glycerol and fatty acid are removed, 1,3 diglycerides of available content 96wt% are commercialized oil and fat product.
Embodiment 2:
(1) lipase is modified:
The 2- methyl 4 of 1 mmol is taken, the nothing of 2 mL is added in 5- dicarboxylic acid imidazole (imidazoles dressing agent), 1 mmol N,N'-carbonyldiimidazole
In water dimethyl sulfoxide, under magnetic agitation effect, stops after reacting at room temperature 5h, obtain active body；The active body of 90 μ L is added
In the antarctic candidia lipase liquid for being 30 μm of ol/L to 15 mL concentration, at 4 DEG C, stop reaction after magnetic agitation 4h,
Antarctic candidia lipase by obtained reaction solution 10KD bag filter 24 h of dialysis, after being modified.
(2) immobilized lipase is prepared:
It weighs 371.3mg zinc nitrate to be added in 3.0mL deionized water, obtains solution A；(referred to as by 410.0mg 2-methylimidazole
It is dissolved in 25mL deionized water at 42 DEG C for enzyme solution, the 50.0mg polyvinylpyrrolidone PVP after 2-mIm), 5mL modification,
Obtain solution B；Then two kinds of solution A, solution B solution are mixed, after ten minutes, fixation is collected by centrifugation in 4800rpm for stirring
Change enzyme product, is washed with excessive deionized water, obtain the antarctic candidia lipase of metal-organic framework materials immobilization.
(3) 1,3 diglycerides are prepared:
Fatty acid mixes (molar ratio 2:1) with 5g glycerol after rapeseed oil is hydrolyzed, and obtains reactant, and addition accounts for reactant gross weight
The immobilized lipase of 0.5 wt%, is placed in reaction kettle, and CO is added2Medium, at 20 DEG C, control reaction pressure is 5MPa, is made
Its is in a supercritical state, and reaction was down to room temperature after 2 hours, and slowly releasing carbon dioxide to reactor pressure is normal pressure, filtering
Immobilized lipase is recycled to reuse；Filtering, obtains 1,3 diglyceride of product, product through efficient liquid phase chromatographic analysis,
Under this condition, the mass fraction for obtaining 1,3 diglycerides in reaction product is 67.7%.It goes out glycerol by steam treatment
And fatty acid, 1,3 diglycerides of available content 95wt% are commercialized oil and fat product.
Embodiment 3:
(1) lipase is modified:
The 2- methyl 4,5- dicarboxylic acid imidazole (imidazoles dressing agent) of 1 mmol, 1 mmol N,N'-carbonyldiimidazole is taken to be added to the nothing of 2 mL
In water dimethyl sulfoxide, magnetic agitation stops after reacting at room temperature 10 h, obtains active body；The active body of 90 μ L is added to 10
ML concentration is to stop reaction after 12 h of magnetic agitation at 2 DEG C in the porcine pancreatic lipase liquid of 100 μm of ol/L, anti-by what is obtained
Answer liquid 10KD bag filter 24 h of dialysis, the porcine pancreatic lipase after being modified.
(2) immobilized lipase is prepared:
It weighs 371.3mg zinc nitrate to be added in 3.0mL deionized water, obtains solution A；(referred to as by 410.0mg 2-methylimidazole
25mL is dissolved at 42 DEG C for porcine pancreatic lipase enzyme solution, the 50.0mg polyvinylpyrrolidone PVP after 2-mIm), 5mL modification
In deionized water, solution B is obtained；Then two kinds of solution A, solution B solution are mixed, stirring 7 minutes after, 4800rpm from
The heart collects immobilised enzymes product, is washed with excessive deionized water, obtains the pig pancreas fat of metal-organic framework materials immobilization
Enzyme.
(3) 1,3 diglycerides are prepared:
Fatty acid mixes (molar ratio 2:1) with 5g glycerol after soybean oil is hydrolyzed, and obtains reactant, and addition accounts for reactant gross weight 10
The immobilized lipase of wt%, is placed in reaction kettle, and CO is added2Medium is warming up to 90 DEG C, and control reaction pressure is 40MPa, is made
Its is in a supercritical state, and reaction was down to room temperature after 15 hours, and slowly releasing carbon dioxide to reactor pressure is normal pressure, filtering
Immobilized lipase is recycled to reuse；Filtering, obtains 1,3 diglyceride of product, product through efficient liquid phase chromatographic analysis,
Under this condition, the mass fraction for obtaining 1,3 diglycerides in reaction product is 64.8%, is gone out glycerol by steam treatment
And fatty acid, 1,3 diglycerides of available content 93wt% are commercialized oil and fat product.
In addition, the lipase in the present invention in fatty enzyme solution equally can be Aspergillus oryzae lipase, lipase from Aspergillus Niger, rice
One kind of black wool mould lipase, Pseudomonas cepacia lipase or thermus thermophilus lipase；Fatty acid equally can be
After one of corn oil, castor oil, cottonseed oil, tung oil, stillingia oil, fish oil, lard or more than one mixture hydrolysis
Fatty acid.The carrier that the present invention uses is metal-organic framework materials.
The embodiment is a preferred embodiment of the present invention, but present invention is not limited to the embodiments described above, not
In the case where substantive content of the invention, any conspicuous improvement that those skilled in the art can make, replacement
Or modification all belongs to the scope of protection of the present invention.
Claims (10)
1. a kind of supercritical CO2The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, which is characterized in that including following step
It is rapid:
(1) lipase is modified:
Imidazoles dressing agent and N,N'-carbonyldiimidazole are added in anhydrous dimethyl sulfoxide, magnetic agitation, room temperature reaction obtains activity
Body；Active body is added in fatty enzyme solution, magnetic agitation reaction, dialysis, the lipase after being modified；
(2) immobilized lipase is prepared:
Zinc nitrate is add to deionized water, solution A is obtained；By the lipase and polyethylene pyrrole after 2-methylimidazole, modification
Pyrrolidone is dissolved in deionized water, obtains solution B；Solution A is mixed with solution B, is stirred, centrifugation, washing obtain immobilization
Lipase；
(3) 1,3 diglycerides are prepared:
Fatty acid is mixed with glycerol, obtains reactant, immobilized lipase is added, is placed in reaction kettle, CO is added2Medium, instead
It answers, filters, obtain 1,3 diglycerides.
2. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, feature
It is, in step (1), the molar ratio of the imidazoles dressing agent and N,N'-carbonyldiimidazole is 1:1；The time of the room temperature reaction is 2-
10h。
3. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, feature
It is, in step (1), the imidazoles dressing agent is 2- methyl 4- carboxylic acid imidazoles or 2- methyl 4,5- dicarboxylic acid imidazole.
4. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, feature
It is, in step (1), the volume ratio of the active body and fatty enzyme solution is 90 μ L:5-15mL, and the concentration of the lipase is
30-150μmol/L。
5. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, it is special
Sign is, in step (1), the temperature of the magnetic agitation is 0-4 DEG C, and the time of the magnetic agitation is 4-12h.
6. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, feature
Be, in step (1), it is described fat enzyme solution in lipase be candida rugosa lipase, antarctic candidia lipase,
Porcine pancreatic lipase, Aspergillus oryzae lipase, lipase from Aspergillus Niger, rice black wool mould bacterium lipase, Pseudomonas cepacia lipase or
One kind of thermus thermophilus lipase.
7. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, it is special
Sign is, in step (2), the amount ratio of the zinc nitrate, deionized water and 2-methylimidazole is 10-400mg:1-5mL:
410.0mg；The amount ratio of lipase and polyvinylpyrrolidone after the 2-methylimidazole, modification is 410.0mg:5mL:
50.0mg；The temperature of the dissolution is 42 DEG C；The time of the stirring is 5-10min.
8. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, it is special
Sign is, in step (3), the molar ratio of the fatty acid and glycerol is 2:1, and the dosage of immobilized lipase accounts for reaction-ure mixture
0.5-10 wt%.
9. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, feature
It is, in step (3), the temperature of the reaction is 20-90 DEG C, and the pressure of the reaction is 5-40MPa, the time of the reaction
It is 2-15 hours.
10. supercritical CO according to claim 12The method that technique immobilized enzyme catalysis prepares 1,3 diglycerides, it is special
Sign is, in step (3), the source of the fatty acid be rapeseed oil, soybean oil, peanut oil, corn oil, castor oil, cottonseed oil,
One of tung oil, stillingia oil, fish oil, lard or more than one mixture.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110195052A (en) * | 2019-05-31 | 2019-09-03 | 浙江工业大学 | A kind of photosynthetic bacteria immobilization particle and the preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101555500A (en) * | 2009-05-22 | 2009-10-14 | 天津大学 | Method for preparing diglyceride by enzyme catalysis in supercritical fluids system |
| CN104087572A (en) * | 2014-07-01 | 2014-10-08 | 清华大学 | Protein and metal organic skeleton compound composite material and preparation method thereof |
-
2018
- 2018-08-28 CN CN201810985475.9A patent/CN109055447A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101555500A (en) * | 2009-05-22 | 2009-10-14 | 天津大学 | Method for preparing diglyceride by enzyme catalysis in supercritical fluids system |
| CN104087572A (en) * | 2014-07-01 | 2014-10-08 | 清华大学 | Protein and metal organic skeleton compound composite material and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| FABRÍCIO M. GOMES: "DETERMINAÇÃO DAS PROPRIEDADES CATALÍTICAS EM MEIO AQUOSO E ORGÂNICO DA LIPASE DE Candida rugosa IMOBILIZADA EM CELULIGNINA QUIMICAMENTE MODIFICADA POR CARBONILDIIMIDAZOL", 《DETERMINAÇÃO DAS PROPRIEDADES CATALÍTICAS EM MEIO AQUOSO》 * |
| RU JIA: "Enhancing Catalytic Performance of Porcine Pancreatic Lipase by Covalent Modification Using Functional Ionic Liquids", 《ACS CATAL.》 * |
| 唐苏苏: "功能化离子液体修饰的 SBA-15 固定化 Burkholderia cepacia 脂肪酶", 《催化学报》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110195052A (en) * | 2019-05-31 | 2019-09-03 | 浙江工业大学 | A kind of photosynthetic bacteria immobilization particle and the preparation method and application thereof |
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