CN109082345A - A kind of method of step conversion high phospholipid crude oil production fatty acid - Google Patents
A kind of method of step conversion high phospholipid crude oil production fatty acid Download PDFInfo
- Publication number
- CN109082345A CN109082345A CN201811112970.5A CN201811112970A CN109082345A CN 109082345 A CN109082345 A CN 109082345A CN 201811112970 A CN201811112970 A CN 201811112970A CN 109082345 A CN109082345 A CN 109082345A
- Authority
- CN
- China
- Prior art keywords
- lipase
- crude oil
- fatty acid
- phase
- liquid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/04—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis
- C11C1/045—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by hydrolysis using enzymes or microorganisms, living or dead
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention belongs to bioengineering and food technology field, the method of specifically a kind of step conversion high phospholipid crude oil production fatty acid, the following steps are included: the enzyme solution that (1) configuration phosphatidase and lipase concentration are 1-5000U/mL, soluble-salt, hydrophilic solvent and high phospholipid crude oil are added into enzyme solution, are made into more liquid-phase systems；(2) configured more liquid-phase systems are subjected to enzymic catalytic reaction under agitation, after reaction, stands or is centrifuged to being divided into four layers, collecting top layer is fatty acid.The present invention provides the characteristic at differential responses interface using more liquid-phase system synchronous high-efficiency separating and extracting different materials and for different interfacial reactions, and differential responses is avoided to interfere with each other, and greatly improves its catalytic efficiency.This method has many advantages, such as to be greatly reduced that separation costs, energy consumption are small, raw material availability is high, process is simple simultaneously.
Description
Technical field
The invention belongs to bioengineering and food technology field, are related to the separation and application technology of enzyme, are related specifically to
Utilize the method for enzyme process pretreatment high phosphorus grease production fatty acid.
Background technique
Fatty acid is widely used in surfactant, food and doctor as the most important basic material in oil and fat chemical field
The fields such as medicine.Currently, the annual output of fatty acid is more than 3,500,000 tons, main industrial production approach is produced by grease hydrolysis
Raw.In recent years, using the interfacial enzymes hydrolysate oil such as lipase production fatty acid due to mild condition, low energy consumption, side reaction is few
Etc. advantages, it has also become the hot spot of industry.
In recent years, can industrialize unedible oil rouge production fatty acid using rice bran oil etc. becomes industry new lover.However, usually
Contain a large amount of phosphatide in this quasi-grease, and phosphatide belongs to surfactant, during grease hydrolysis, is primarily present in oil
It is easy to wrap up the lipase for being in oil-water interfaces together at water termination, seriously affect hydrolysis efficiency.In addition, phosphatide can also cause oil
Rancid and inverse, therefore in order to guarantee oil product stablize, it is necessary to except the phosphatide for the middle overwhelming majority of deoiling.Therefore, by industrial
It needs a series of complex technologies such as washing, pickling and phosphatide enzyme hydrolysis to remove most phosphatide in oil, then could
Associated fat enzymatic hydrolysis reaction is carried out, qualified fatty acid is produced.It can be with the characteristic of hydrolytic phosphatide, by phosphatide using phosphatidase
Enzyme and lipase are added in reaction system simultaneously, make its synchronous hydrolysis, being expected to have the function that mutually promote is one relatively good
Thinking.However, this method is but rarely reported in practical application.It is primarily due in traditional oils aqueous systems, two kinds of enzymes
It is in same interface with substrate, causes two kinds of reactions to interfere with each other, conditions each other, reduce its enzymatic efficiency instead, lead
Cause entire enzymatic process time-consuming too long, efficiency is extremely low.
Summary of the invention
The purpose of the present invention is being industrially difficult to direct hydrolysis for current high phospholipid crude oil, need to pass through complicated technology
Most phosphatide are removed, then just can be carried out associated fat enzymatic hydrolysis reaction, cause the process side reaction more, energy consumption is high,
The problems such as time is long, at high cost provides a kind of utilization immobilized double enzymes of more liquid-phase systems simultaneous removing phosphorus from high phospholipid crude oil
The method of rouge and preparing fatty acid by hydrolyzing, is simplified technique, short processing time, and cost reduces, economically feasible.
The purpose of the present invention is achieved through the following technical solutions:
A kind of method of step conversion high phospholipid crude oil production fatty acid, comprising the following steps:
(1) enzyme solution that phosphatidase and lipase concentration are 1-5000U/mL is configured, soluble-salt, hydrophilic is added into enzyme solution
Property solvent and high phospholipid crude oil, are made into more liquid-phase systems；The soluble-salt, hydrophilic solvent and high phospholipid crude oil and enzyme solution
Mass ratio is respectively 0.03-1,0.02-1 and 0.02-8；
(2) configured more liquid-phase systems are subjected to enzymic catalytic reaction under agitation, after reaction, stand or from
To being divided into four layers, (upper layer is fatty acid phase to the heart；The second layer is the solid phase rich in phosphatide, and third layer and the 4th layer are respectively rich alcohol phase
Or rich salt phase, enzyme focus primarily upon a rear two-phase wherein phase), collecting top layer is fatty acid.
Preferably, step (1) hydrophilic solvent is hydrophilic organic solvent, is selected from polyethylene glycol, ethyl alcohol, poly- third
One or more of alcohol, isopropanol, the tert-butyl alcohol, ethylene glycol and n-butanol.
Preferably, step (1) hydrophilic solvent is hydrophilic ionic-liquid, is selected from [BMIM] Br, [BMIM] BF4、
[DMIM]Cl、[EMIM]ETSO4One or more of [OMIM] Cl.
Preferably, step (1) described soluble-salt is sodium citrate, ammonium sulfate, sodium sulphate, potassium carbonate, potassium phosphate, phosphoric acid
One or more of potassium dihydrogen and dipotassium hydrogen phosphate.
Preferably, the mass ratio of step (1) soluble-salt, hydrophilic solvent, high phospholipid crude oil and enzyme solution is respectively
0.1-0.6,0.1-0.8 and 0.5-50.
Preferably, the condition of step (2) enzymic catalytic reaction are as follows: speed of agitator is 100-1500 revs/min, and reaction temperature is
10-40 DEG C, reaction time 0.1-10h.
Preferably, the reaction time is 0.5-5h.
It is highly preferred that the reaction time is 1-2h.
Operation generally lower than solvent it is volatile at a temperature of carry out.In order to reach concentration effect as far as possible most
Good, the pH value of adjustable system, the pH value of three liquid-phase system is 2-12.
Preferably, pH value 3.5-9.5.
Preferably, step (1) lipase and phospholipase concentration are 10-500U/mL.
Preferably, the mass ratio of the soluble-salt, hydrophilic solvent, high phospholipid crude oil and enzyme solution is respectively 0.1-0.6,
0.1-0.8 and 0.5-5.
Preferably, step (2) centrifugal condition is that 5000rpm is centrifuged 5min.
Preferably, the phosphatidase is phosphatidase Ultra (Lecitase ultra), and the lipase is lipase ay S
(Candida rugosa lipase), lipase PL20000L (Rhizomucormiehei lipase).
Rich enzyme layer obtained by collection step (2) retrieves addition reactor, new high phospholipid crude oil is supplemented, in reactor
Reaction, stands or centrifugation is to being layered, and recycles rich enzyme phase, can be used as repeating to react；The repetitive process is to repeat 1~500 time；It is excellent
Selection of land, repetitive process are to repeat 3~100 times.
In above-mentioned phosphatidase and lipase-catalyzed reaction, phosphatidase and lipase can come from that naturally, people can also be passed through
Work fermentation generates.It can be fermentation liquid, can be the thick enzyme after simple purification, can also be purified rear pure enzyme.
Find that more liquid-phase systems can promote phosphatidase and lipase-catalyzed efficiency in the research of early period.However, recent
It has been surprisingly found that, two kinds of enzymes is added in the system simultaneously, additionally it is possible to play the role of mutually promoting, this is derived from the body in research
Under system, two kinds are reacted while betiding different interfaces, greatly improve the efficiency of enzyme.
Effect and benefit of the invention:
The present invention provides difference using more liquid-phase system synchronous high-efficiency separating and extracting different materials and for different interfacial reactions
The characteristic of reaction interface opens up second " battlefield " for phospholipid hydrolysis, differential responses is avoided to interfere with each other, and greatly improves its catalysis effect
Rate.In the system, hydrolysate fatty acid can be distributed in upper phase, it is solid that the more hydrophilic colloid of phospholipid conversion is enriched in the second layer
Phase, and enzyme is enriched in another phase, convenient for purifying and recycling, so that separation costs be greatly reduced.This method has energy consumption small, former
Expect the advantages that utilization rate is high, process is simple, during solving high phospholipid crude oil preparing fatty acid by hydrolyzing, there are complex process,
Side reaction is more, and energy consumption is high, the technical problem of time length.
Specific embodiment
The present invention is more specifically described in detail combined with specific embodiments below, but embodiments of the present invention are unlimited
Routine techniques progress can refer to for not specifically specified technological parameter in this.
Phosphatidase used in the present embodiment, Ultra, PL20000L are purchased from Novozyme company, and AYS is purchased from Amano company.
Embodiment 1
Take the thick enzyme phosphate mixed liquor of 6.2g Ultra containing phosphatidase (70U/mL) and lipase ay S (100U/mL)
The sodium sulphate of 1.1g is added in (0.1Mm, pH 7.0), and 2.5g polyethylene glycol 400 and 2g high phospholipid crude oil (phosphatide are added after mixing
Content 2%), it is fitted into triangular flask and is uniformly mixed, be made into more liquid-phase systems；It reacts, is controlled 37 under 200rpm stirring
10min is reacted at DEG C.After reaction, setting 5000rpm revolving speed is centrifuged 5min, is divided into four phases, and liquid phase product is fatty acid
Phase, the second layer are the phosphatide solid phase rich in colloid, and third layer and the 4th layer are respectively that rich alcohol phase or rich salt phase, enzyme focus primarily upon
Third layer.
Separately 6.2g is taken to contain only the crude enzyme liquid of lipase ay S (100U/mL), the sodium sulphate of 1.1g is added, is added after mixing
2.5g polyethylene glycol 400 and 2g high phospholipid crude oil (2%), react as a control group under the same conditions.
It takes more liquid phase upper, middle and lower mutually to measure its content of fatty acid, enzyme activity and phosphorus content respectively, phosphatide in oily phase can be obtained and gone
It is 66.8% and 55.24% except rate and content of fatty acid have respectively reached, and the content of fatty acid of control group is only 33.71%,
In addition, its lipase and phosphatidase are mainly allocated in middle phase, in the distribution coefficient of lower phase be respectively 32.64 and 25.00, two kinds of enzymes
The rate of recovery be more than 98%.
Embodiment 2
The thick enzyme mixation of 6.5g Ultra containing phosphatidase (70U/mL) and lipase TL-100L (100U/mL) are taken, is added
2g polyethylene glycol 400 and 2g high phospholipid crude oil (2%) is added in the ammonium sulfate of 2g after mixing, be fitted into triangular flask and mix
It is even, it is made into more liquid-phase systems；It is reacted under 200rpm stirring, control reacts 2h at 37 DEG C.After reaction, it sets
5000rpm revolving speed is centrifuged 5min, is divided into four phases, and liquid phase product is fatty acid phase, and the second layer is the phosphatide solid phase rich in colloid,
Third layer and the 4th layer of respectively rich alcohol phase or rich salt phase, enzyme focus primarily upon third layer.
6.5g is separately taken to contain only the crude enzyme liquid of lipase TL-100L (100U/mL), it is poly- that 2g is added in the ammonium sulfate of 2g after mixing
Ethylene glycol 400 and 2g high phospholipid crude oil (2%), react as a control group under the same conditions.
It takes more liquid phase upper, middle and lower mutually to measure its content of fatty acid, enzyme activity and phosphorus content respectively, phosphatide in oily phase can be obtained and gone
It is 94.3% and 57.68% except rate and content of fatty acid have respectively reached, and the content of fatty acid of control group is only 36.68%,
In addition, its lipase and phosphatidase are mainly allocated in middle phase, in the distribution coefficient of lower phase be respectively 182.91 and 15.00, fat
The rate of recovery of enzyme has been more than 99%, and the rate of recovery of phosphatidase has reached 97.5%.
Embodiment 3
The thick enzyme mixation of 6.5g Ultra containing phosphatidase (70U/mL) and lipase ay S (100U/mL) are taken, 1.5g is added
Sodium sulphate, after mixing be added 2g [BMIM] BF4With 2g high phospholipid crude oil (2%), it is fitted into triangular flask and is uniformly mixed, match
At more liquid-phase systems；It is reacted under 200rpm stirring, control reacts 2h at 37 DEG C.After reaction, 5000rpm revolving speed is set
It is centrifuged 5min, is divided into four phases, liquid phase product is fatty acid phase, and the second layer is the phosphatide solid phase rich in colloid, third layer and the
Four layers are respectively that rich alcohol phase or rich salt phase, enzyme focus primarily upon the 4th layer.
Separately 6.5g is taken to contain only the crude enzyme liquid of lipase ay S (100U/mL), the sodium sulphate of 1.5g is added, 2g is added after mixing
[BMIM]BF4With 2g high phospholipid crude oil (2%), react under the same conditions as a control group.
It takes more liquid phase upper, middle and lower mutually to measure its content of fatty acid, enzyme activity and phosphorus content respectively, phosphatide in oily phase can be obtained and gone
It is 94.26% and 38.73% except rate and content of fatty acid have respectively reached, and the content of fatty acid of control group is only 33.71%,
In addition, its lipase and phosphatidase are mainly allocated in lower phase, the rate of recovery has respectively reached 99.25% and 95.21%.
Embodiment 4
The thick enzyme mixation of 6.2g Ultra containing phosphatidase (35U/mL) and lipase ay S (100U/mL) are taken, 1.1g is added
Sodium sulphate, 2.5g polyethylene glycol 400 and 2g high phospholipid crude oil (2%) are added after mixing, is fitted into triangular flask mixing
It is even, it is made into more liquid-phase systems；It is reacted under 200rpm stirring, control reacts 1h at 37 DEG C.After reaction, it sets
5000rpm revolving speed is centrifuged 5min, is divided into four phases, and liquid phase product is fatty acid phase, and the second layer is the phosphatide solid phase rich in colloid,
Third layer and the 4th layer of respectively rich alcohol phase or rich salt phase, enzyme focus primarily upon third layer.
Taking-up is added to new rich salt phase and high phospholipid crude oil containing enzyme with third layer, repeats above-mentioned reaction totally 7 times.7 weights
After multiple reaction, the vigor of lipase and phosphatidase keeps the 92.85% and 92.70% of first vigor, phosphatide removal rate in oily phase
86.07% and 88.13% have been respectively reached with content of fatty acid.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, other any changes, modifications, substitutions, combinations, simplifications made without departing from the spirit and principles of the present invention,
It should be equivalent substitute mode, be included within the scope of the present invention.
Claims (10)
1. a kind of method of step conversion high phospholipid crude oil production fatty acid, which comprises the following steps:
(1) phosphatidase and lipase concentration are configured as the enzyme solution of 1-5000U/mL, it is molten that soluble-salt, hydrophily are added into enzyme solution
Agent and high phospholipid crude oil, are made into more liquid-phase systems；The quality of the soluble-salt, hydrophilic solvent and high phospholipid crude oil and enzyme solution
Than being respectively 0.03-1,0.02-1 and 0.02-8；
(2) configured more liquid-phase systems are subjected to enzymic catalytic reaction under agitation, after reaction, stands or is centrifuged extremely
It is divided into four layers, collecting top layer is fatty acid.
2. the method according to claim 1, wherein step (1) hydrophilic solvent is polyethylene glycol, second
One or more of alcohol, poly- propyl alcohol, isopropanol, the tert-butyl alcohol, ethylene glycol and n-butanol；Or the hydrophilic solvent is
[BMIM]Br、[BMIM]BF4、[DMIM]Cl、[EMIM]ETSO4One or more of [OMIM] Cl.
3. the method according to claim 1, wherein step (1) described soluble-salt is sodium citrate, sulfuric acid
One or more of ammonium, sodium sulphate, potassium carbonate, potassium phosphate, potassium dihydrogen phosphate and dipotassium hydrogen phosphate.
4. method according to claim 1 or 2 or 3, which is characterized in that the condition of step (2) enzymic catalytic reaction are as follows: stirring
Revolving speed is 100-1500 revs/min, and reaction temperature is 10-40 DEG C, reaction time 0.1-10h, pH value 2-12.
5. according to the method described in claim 4, it is characterized in that, the reaction time is 0.5-5h, pH value 3.5-9.5.
6. according to the method described in claim 5, it is characterized in that, the reaction time is 1-2h.
7. method according to claim 1 or 2 or 3, which is characterized in that step (1) lipase and phospholipase concentration
It is 10-500U/mL.
8. method according to claim 1 or 2 or 3, which is characterized in that the soluble-salt, hydrophilic solvent, high phospholipid
The mass ratio of crude oil and enzyme solution is respectively 0.1-0.6,0.1-0.8 and 0.5-5.
9. method according to claim 1 or 2 or 3, which is characterized in that step (2) centrifugal condition be 5000rpm from
Heart 5min.
10. method according to claim 1 or 2 or 3, which is characterized in that the phosphatidase is phosphatidase Ultra
(Lecitase ultra), the lipase are lipase ay S (Candida rugosa lipase), lipase PL20000L
(Rhizomucormiehei lipase)。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811112970.5A CN109082345B (en) | 2018-09-25 | 2018-09-25 | Method for producing fatty acid by one-step conversion of high-phospholipid crude oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811112970.5A CN109082345B (en) | 2018-09-25 | 2018-09-25 | Method for producing fatty acid by one-step conversion of high-phospholipid crude oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109082345A true CN109082345A (en) | 2018-12-25 |
| CN109082345B CN109082345B (en) | 2021-06-08 |
Family
ID=64842513
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811112970.5A Active CN109082345B (en) | 2018-09-25 | 2018-09-25 | Method for producing fatty acid by one-step conversion of high-phospholipid crude oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109082345B (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109234007A (en) * | 2018-10-16 | 2019-01-18 | 华南理工大学 | A kind of fish oil degumming discoloration method |
| CN112359073A (en) * | 2020-10-16 | 2021-02-12 | 华南理工大学 | Method for preparing high-purity conjugated linoleic acid isomer by double-enzyme method resolution |
| CN113234762A (en) * | 2021-05-28 | 2021-08-10 | 华南理工大学 | Method for modifying euphausia superba oil by multiphase enzyme method system |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103184245A (en) * | 2013-03-01 | 2013-07-03 | 华南理工大学 | Method for producing fatty acid by hydrolyzing lipid through three liquid-phase lipase catalytic systems |
| CN105316368A (en) * | 2015-11-06 | 2016-02-10 | 华南理工大学 | Method for enriching polyunsaturated fatty acids by virtue of enzyme method |
| CN105349255A (en) * | 2015-11-06 | 2016-02-24 | 华南理工大学 | Enzyme method degumming method |
| CN108048212A (en) * | 2017-12-08 | 2018-05-18 | 东北农业大学 | A kind of method of phosphatidase degumming depickling synchronous with lipase |
-
2018
- 2018-09-25 CN CN201811112970.5A patent/CN109082345B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103184245A (en) * | 2013-03-01 | 2013-07-03 | 华南理工大学 | Method for producing fatty acid by hydrolyzing lipid through three liquid-phase lipase catalytic systems |
| CN105316368A (en) * | 2015-11-06 | 2016-02-10 | 华南理工大学 | Method for enriching polyunsaturated fatty acids by virtue of enzyme method |
| CN105349255A (en) * | 2015-11-06 | 2016-02-24 | 华南理工大学 | Enzyme method degumming method |
| CN108048212A (en) * | 2017-12-08 | 2018-05-18 | 东北农业大学 | A kind of method of phosphatidase degumming depickling synchronous with lipase |
Non-Patent Citations (3)
| Title |
|---|
| YANGYANG JIANG ET AL: "Enzymatic Hydrolysis of Penicillin for 6-APA Production in Three-Liquid-Phase System", 《APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY》 * |
| 赵余庆: "《中药及天然产物提取制备关键技术》", 31 January 2012, 中国医药科技出版社 * |
| 陈华等: "三液相酶催化体系水解橄榄油的研究", 《中国油脂》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109234007A (en) * | 2018-10-16 | 2019-01-18 | 华南理工大学 | A kind of fish oil degumming discoloration method |
| CN112359073A (en) * | 2020-10-16 | 2021-02-12 | 华南理工大学 | Method for preparing high-purity conjugated linoleic acid isomer by double-enzyme method resolution |
| CN113234762A (en) * | 2021-05-28 | 2021-08-10 | 华南理工大学 | Method for modifying euphausia superba oil by multiphase enzyme method system |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109082345B (en) | 2021-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109295030B (en) | Method for enriching DHA and EPA in fish oil based on liquid immobilized enzyme | |
| CN105316368B (en) | A kind of method of enzyme process enriching polyunsaturated fatty acid | |
| CN103184245B (en) | Method for producing fatty acid by hydrolyzing lipid through three liquid-phase lipase catalytic systems | |
| AU2021201921B2 (en) | Polyunsaturated fatty acid triglyceride and preparation and uses thereof | |
| CN109777606B (en) | Method for extracting DHA (docosahexaenoic acid) crude oil | |
| CN109082345A (en) | A kind of method of step conversion high phospholipid crude oil production fatty acid | |
| CN105821088A (en) | Method for preparing glyceride rich in EPA and DHA through enzyme catalysis | |
| CN105349255A (en) | Enzyme method degumming method | |
| CN104046662B (en) | Transesterification preparation method for 1,3-dioleic acid-2-triglyceride palmitate | |
| CN106566658A (en) | Enzymatic deacidifying method for high-acid-value oil | |
| EP1809755B1 (en) | Biodiesel production from soapstock | |
| CN113234762B (en) | Method for modifying euphausia superba oil by multiphase enzyme method system | |
| US20220017935A1 (en) | A Method for Enzymatic Resolution of Chiral Substances | |
| CN101313075A (en) | Fermentative production of organic compounds using substances containing dextrin | |
| CN106318985A (en) | Microbial lipid | |
| CN102618609B (en) | Method for comprehensively utilizing degreased rice bran | |
| CN113621657B (en) | Method for catalyzing grease hydrolysis decarboxylation by cell-like multiphase emulsion optical enzyme system | |
| CN111172209B (en) | Method for preparing monoglyceride type n-3PUFA by enzyme method | |
| CN113684126A (en) | Device and method for continuously synthesizing diglyceride by holoenzyme method in multi-liquid-phase system | |
| CN105441494A (en) | Method for synthesizing 1,2-diglyceride with an enzymic method | |
| CN107338274A (en) | A kind of method for preparing fatty glyceride | |
| CN115261148B (en) | Application of eutectic solvent in grease dehydration | |
| CN105087686A (en) | Method for preparing biodiesel through lipase catalysis | |
| CN115232675B (en) | Production method of waste oil bioenzyme re-esterified biodiesel | |
| JP2011182741A (en) | Method for producing alcohol |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |