CN111593045A - Immobilized magnetoenzyme preparation method of OPO grease in supercritical state - Google Patents
Immobilized magnetoenzyme preparation method of OPO grease in supercritical state Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/14—Enzymes or microbial cells immobilised on or in an inorganic carrier
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- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
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- C12N11/00—Carrier-bound or immobilised enzymes; Carrier-bound or immobilised microbial cells; Preparation thereof
- C12N11/02—Enzymes or microbial cells immobilised on or in an organic carrier
- C12N11/10—Enzymes or microbial cells immobilised on or in an organic carrier the carrier being a carbohydrate
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/14—Hydrolases (3)
- C12N9/16—Hydrolases (3) acting on ester bonds (3.1)
- C12N9/18—Carboxylic ester hydrolases (3.1.1)
- C12N9/20—Triglyceride splitting, e.g. by means of lipase
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- 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
- C12P7/6454—Glycerides by esterification
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- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Y—ENZYMES
- C12Y301/00—Hydrolases acting on ester bonds (3.1)
- C12Y301/01—Carboxylic ester hydrolases (3.1.1)
- C12Y301/01003—Triacylglycerol lipase (3.1.1.3)
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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
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- 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 relates to a preparation method of immobilized magnetoenzyme of OPO grease in a supercritical state. The method firstly uses nano-scale Fe3O4Preparing a novel magnetic carrier from the particles, and adhering the esterified synthetase and the Sn-1,3 position specific lipase to the magnetic carrier to respectively obtain the immobilized esterified synthetic lipase and the immobilized Sn-1,3 position specific lipase. Then, immobilized magnetozyme catalysis is adopted in a two-step supercritical state to prepare the OPO structure grease. Firstly, using palmitic acid and glycerol as raw materials, using immobilized esterification synthetic lipase as a catalyst, and performing supercritical CO2High quality palmitic acid triglyceride is obtained in this state. Secondly, the palmitic acid triglyceride and the oleic acid are used as raw materialsIn supercritical CO2Under the state, the crude product of OPO grease is prepared by the catalysis of immobilized Sn-1,3 position specific lipase. And finally, purifying the product by utilizing molecular distillation to obtain the grease with high content of OPO structure. The invention is helpful for further promoting the development of OPO structure grease, and achieves the purposes of improving the synthesis efficiency and improving the OPO content.
Description
Technical Field
The invention relates to a preparation method of immobilized magnetoenzyme of OPO grease in a supercritical state.
Background
Breast milk is the primary source of nutrition for infants in the early stages of birth to meet the growing physiological needs of infants in the first month after birth. Approximately 50% of the energy in breast milk is supplied by triglycerides in the milk, which are esterified from 3 fatty acids and a trihydroxy glycerol backbone, the structural differences of which include the specific localization effects of the fatty acids (Sn-1 and Sn-3, located on the outer side of triacylglycerols, and the middle Sn-2). Palmitic acid is now known to be the most important saturated fatty acid in breast milk, with about 70% being esterified at the Sn-2 position of the triglyceride molecule. The digestion and absorption of the breast milk fat of the infant are higher than those of the infant formula milk powder, and are closely related to the position distribution of the breast milk fatty acid in the triglyceride. Saturated fatty acids in the vegetable oil are distributed at Sn-1 and Sn-3 positions, and unsaturated fatty acids are distributed at Sn-2 position. In the production of infant formula, if a product with a fatty acid composition close to that of breast milk fat can be obtained by mixing several vegetable fats, the structure type cannot reach a level close to that of breast milk fat. The result difference has great influence on the digestion, absorption and metabolism of infants, and can easily cause energy intake insufficiency, calcium element loss and constipation of infants. With the gradual and deep understanding of human milk fat and infant nutrition absorption, the application of the structural oil with Sn-2 orientation effect in the infant formula milk powder industry is gradually expanded, and the application of the structural oil is an important component of the breast emulsification process of the infant formula milk powder.
The structural oil 1, 3-dioleoyl-2-palmitic acid triglyceride (OPO) is a novel infant food nutrition enhancer (oleic acid is on the Sn-1 and 3 positions, and palmitic acid is on the Sn-2 position), is also an important component of breast milk structural fat, can enable infants to absorb and utilize calcium and energy to the maximum extent, and obviously reduces the possibility of constipation, abdominal pain and intestinal obstruction of the infants. As early as the 80's of the 20 th century, research on the preparation of structural oils and fats in which palmitic acid is mainly located at the Sn-2 position has been conducted. At present, a plurality of companies are dedicated to researching the OPO structure grease for years, and the production process adopts lipase to catalyze ester exchange so as to rearrange the position of fatty acid on glycerol molecule. At present, the problems of the OPO grease are that the content of OPO is low, the production cost is high, and the production efficiency of products needs to be further improved.
The enzyme is widely researched and applied in the field of biochemistry as a catalyst, and has the remarkable advantages of mild catalytic conditions, strong specificity, simple reaction equipment, low energy consumption, less environmental pollution and the like. At present, enzymes are widely applied in the fields of medicine, food production, chemical industry, agriculture and the like. The Sn-1, 3-specific lipase is a key biocatalyst in OPO synthesis, and after the Sn-1, 3-specific lipase is immobilized, the recycling frequency and specific activity of the Sn-1, 3-specific lipase can be improved, the specificity of the Sn-1, 3-specific lipase is ensured, and the production cost and market price of OPO structure grease are obviously reduced.
The enzyme is immobilized on a carrier, so that the enzyme has high stability and can be repeatedly used, and the application of the enzyme is greatly promoted due to the immobilized enzyme. Among a wide variety of immobilized enzyme carriers, a magnetic carrier becomes an important immobilized carrier due to its unique magnetic characteristics. The magnetic carrier, as a composite material recently developed, not only has the magnetic responsiveness of a magnetic material, but also has many characteristics of a polymer material. Due to higher magnetic effect, the magnetic immobilized carrier can realize rapid separation and positioning under the action of a magnetic field, and is a hotspot of lipase carrier research in recent years.
Supercritical CO2The extraction is the most advanced internationally at presentPhysical extraction techniques, with a strong gas-like penetration and a greater density like liquids. CO in supercritical state2Is a nonpolar reaction solvent, has good solubility, and can replace fat-soluble organic solvent to carry out enzyme catalytic reaction. Dissolving fat-soluble reactant in supercritical CO2The material has gas-like diffusion coefficient, can realize rapid mass transfer of solute at lower temperature, and promotes chemical reaction. The immobilized enzyme does not dissolve CO in supercritical state2In addition, the biological activity of some enzymes is improved under the supercritical condition, so that the reaction rate can be doubly improved, and the separation and the refining of products are facilitated. CO 22Is safe, nontoxic and cheap liquid, and is supercritical CO2The extraction has the characteristics of high efficiency, difficult oxidation, pure nature, no chemical pollution and the like.
The invention uses supercritical CO2The oil with the OPO structure is used as a solvent, and is synthesized by adopting a magnetic immobilized lipase oriented catalysis method, so that the aims of improving the synthesis efficiency and improving the OPO content are finally fulfilled.
Disclosure of Invention
The technical scheme adopted by the invention is summarized as follows:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, edible polysaccharide is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion of a cross-linking agent to prepare the novel magnetic carrier. Then, the esterification synthetic enzyme and the Sn-1,3 position specific lipase are adhered to a magnetic carrier under the action of a cross-linking agent to respectively obtain the immobilized esterification synthetic lipase and the immobilized Sn-1,3 position specific lipase.
Wherein the edible polysaccharide is sodium alginate, dialdehyde starch, carboxymethyl chitosan or a compound mixture thereof; the cross-linking agent is glutaraldehyde, polydopamine, 3, 4-dihydroxy benzaldehyde or their mixture.
(2) Adding 1 mol of palmitic acid into a supercritical extractor, adding glycerol with a molar ratio (1.1-2.0):1, and adding immobilized esterification synthetic lipase with a molar number of palmitic acid of 3-8%. Screwing the sealing cover of the extractor to keep the extractor constantGradually pumping liquid CO at 42-60 deg.C2The pressure of the extractor is kept constant at 24-32MPa, the pressure of the separator is kept constant at 2-5MPa, and the reaction is carried out for 4-6 hours under the conditions. After the reaction is finished, stopping the liquid CO2The valve of the separator is opened to collect the reaction products until the pressure in the separator and the extractor is zero, and the collected products are the palmitic acid triglyceride with high quality.
(3) Adding 1 mol of palmitic acid triglyceride into a supercritical extractor, adding oleic acid with a molar ratio (1.1-1.8) to the palmitic acid triglyceride of 1, and adding immobilized Sn-1, 3-position specific lipase with a molar number of the palmitic acid triglyceride of 2.5-6.5%. Screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 42-60 ℃, and gradually pumping in liquid CO2The pressure of the extractor is kept constant at 24-32MPa, the pressure of the separator is kept constant at 2-5MPa, and the reaction is carried out for 4-6 hours under the conditions. After the reaction is finished, stopping the liquid CO2The valve of the separator is opened to collect the reaction product until the pressure in the separator and the extractor is zero, and the collected product is the crude product of the OPO structure grease. And controlling the temperature of the reaction product at 115-135 ℃ under the vacuum condition, and removing free oleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPO grease with the content of 65-85%.
The specific implementation mode is as follows:
the first embodiment is as follows:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, edible polysaccharide is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion of a cross-linking agent to prepare the novel magnetic carrier. Then, the esterification synthetic enzyme and the Sn-1,3 position specific lipase are adhered to a magnetic carrier under the action of a cross-linking agent to respectively obtain the immobilized esterification synthetic lipase and the immobilized Sn-1,3 position specific lipase.
Wherein the edible polysaccharide is sodium alginate, dialdehyde starch, carboxymethyl chitosan or a compound mixture thereof; the cross-linking agent is glutaraldehyde, polydopamine, 3, 4-dihydroxy benzaldehyde or their mixture.
(2) Adding 1 mol of palmitic acid into a supercritical extractor,then, glycerol with the molar ratio of 1.2:1 to the palmitic acid is added, and immobilized esterified synthetic lipase with the mole number of the palmitic acid of 6% is added. Screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 45 ℃, and gradually pumping in liquid CO2The pressure of the extractor was kept constant at 28MPa, and the pressure of the separator was kept constant at 4MPa, under which conditions the reaction was carried out for 5 hours. After the reaction is finished, stopping the liquid CO2The valve of the separator is opened to collect the reaction products until the pressure in the separator and the extractor is zero, and the collected products are the palmitic acid triglyceride with high quality.
(3) 1 mol of palmitic acid triglyceride is added into a supercritical extractor, oleic acid with the mol ratio of 1.5:1 to the palmitic acid triglyceride is added, and immobilized Sn-1, 3-position specific lipase with the mol ratio of the palmitic acid triglyceride of 5.5% is added. Screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 50 ℃, and gradually pumping in liquid CO2The pressure in the extractor was kept constant at 27MPa, and the pressure in the separator was kept constant at 4MPa, under which conditions the reaction was carried out for 5 hours. After the reaction is finished, stopping the liquid CO2The valve of the separator is opened to collect the reaction product until the pressure in the separator and the extractor is zero, and the collected product is the crude product of the OPO structure grease. And (3) controlling the temperature of the reaction product to 125 ℃ under the vacuum-pumping condition, and removing free oleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPO grease with the content of 75%.
The second embodiment is as follows:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, edible polysaccharide is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion of a cross-linking agent to prepare the novel magnetic carrier. Then, the esterification synthetic enzyme and the Sn-1,3 position specific lipase are adhered to a magnetic carrier under the action of a cross-linking agent to respectively obtain the immobilized esterification synthetic lipase and the immobilized Sn-1,3 position specific lipase.
Wherein the edible polysaccharide is sodium alginate, dialdehyde starch, carboxymethyl chitosan or a compound mixture thereof; the cross-linking agent is glutaraldehyde, polydopamine, 3, 4-dihydroxy benzaldehyde or their mixture.
(2) Adding 1 mol of palmitic acid into a supercritical extractor, then adding glycerol with the mol ratio of 1.5:1 to the palmitic acid, and adding immobilized esterification synthetic lipase with the mol ratio of 5% of the palmitic acid. Screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 50 ℃, and gradually pumping in liquid CO2The pressure of the extractor was kept constant at 30MPa, and the pressure of the separator was kept constant at 4MPa, under which conditions the reaction was carried out for 6 hours. After the reaction is finished, stopping the liquid CO2The valve of the separator is opened to collect the reaction products until the pressure in the separator and the extractor is zero, and the collected products are the palmitic acid triglyceride with high quality.
(3) Adding 1 mol of palmitic acid triglyceride into a supercritical extractor, adding oleic acid with the mol ratio of the palmitic acid triglyceride to the palmitic acid triglyceride being 1.6:1, and adding immobilized Sn-1,3 position specific lipase with the mol number of the palmitic acid triglyceride being 6%. Screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 50 ℃, and gradually pumping in liquid CO2The pressure of the extractor was kept constant at 30MPa, and the pressure of the separator was kept constant at 4MPa, under which conditions the reaction was carried out for 5 hours. After the reaction is finished, stopping the liquid CO2The valve of the separator is opened to collect the reaction product until the pressure in the separator and the extractor is zero, and the collected product is the crude product of the OPO structure grease. And (3) controlling the temperature of the reaction product to 130 ℃ under the vacuum-pumping condition, and removing free oleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain OPO grease with the content of 72%.
Claims (2)
1. A preparation method of immobilized magnetozyme of OPO grease in a supercritical state comprises the following steps:
(1) with nanoscale Fe3O4The particles are magnetic matrixes, edible polysaccharide is used as a carrier, and the magnetic nanoparticles are wrapped by the adhesion of a cross-linking agent to prepare a novel magnetic carrier; then, the esterification synthetic enzyme and the Sn-1,3 position specific lipase are adhered to a magnetic carrier under the action of a cross-linking agent to respectively obtain immobilized esterification synthetic lipase and immobilized Sn-1,3 position specific lipase;
(2) in the supercritical extractionAdding 1 mol of palmitic acid into the reactor, adding glycerol with a molar ratio (1.1-2.0) to 1 of the palmitic acid, and adding immobilized esterification synthetic lipase with a molar number of the palmitic acid of 3-8%; screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 42-60 ℃, and gradually pumping in liquid CO2The pressure of the extractor is kept constant at 24-32MPa, the pressure of the separator is controlled to be kept constant at 2-5MPa, and the reaction is carried out for 4-6 hours under the conditions; after the reaction is finished, stopping the liquid CO2The pump-in of (1) opens the valve of the separator to collect the reaction product until the pressure in the separator and the extractor is zero, and the collected product is the high-quality palmitic acid triglyceride;
(3) adding 1 mol of palmitic acid triglyceride into a supercritical extractor, adding oleic acid with a molar ratio (1.1-1.8) to the palmitic acid triglyceride of 1, and adding immobilized Sn-1, 3-position specific lipase with a molar number of the palmitic acid triglyceride of 2.5-6.5%; screwing the sealing cover of the extractor, keeping the constant temperature of the extractor at 42-60 ℃, and gradually pumping in liquid CO2The pressure of the extractor is kept constant at 24-32MPa, the pressure of the separator is controlled to be kept constant at 2-5MPa, and the reaction is carried out for 4-6 hours under the conditions; after the reaction is finished, stopping the liquid CO2The pump-in of (1) is carried out, a separator valve is opened to collect reaction products until the pressure in the separator and the pressure in the extractor are zero, and the collected products are crude products of OPO structure grease; and controlling the temperature of the reaction product at 115-135 ℃ under the vacuum condition, and removing free oleic acid and palmitic acid in the reaction system by molecular distillation to finally obtain the OPO grease with the content of 65-85%.
2. The edible polysaccharide of claim 1, which is sodium alginate, dialdehyde starch, carboxymethyl chitosan or a compound mixture thereof; the cross-linking agent is glutaraldehyde, polydopamine, 3, 4-dihydroxy benzaldehyde or their mixture.
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| CN202010299243.5A CN111593045A (en) | 2020-04-16 | 2020-04-16 | Immobilized magnetoenzyme preparation method of OPO grease in supercritical state |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113174384A (en) * | 2021-04-02 | 2021-07-27 | 仲恺农业工程学院 | Immobilized enzyme, preparation method thereof and application thereof in OPO preparation |
| CN113980951A (en) * | 2021-11-23 | 2022-01-28 | 东北农业大学 | Immobilized CALB preparation method based on nano dialdehyde starch carrier |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757988A (en) * | 2012-07-25 | 2012-10-31 | 浙江大学 | Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride |
| CN104313010A (en) * | 2014-11-05 | 2015-01-28 | 太原理工大学 | Preparation method of magnetic response composite lipase and application in biodiesel synthesis |
| CN105602931A (en) * | 2016-03-11 | 2016-05-25 | 东北农业大学 | Method for synthesizing carbon chain triacylglycerol under supercritical CO2 system based on magnetic immobilized enzyme method |
| CN109251943A (en) * | 2018-08-28 | 2019-01-22 | 江苏大学 | A kind of supercritical CO2Under the conditions of the enzymatic method for preparing OPO structured lipid |
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2020
- 2020-04-16 CN CN202010299243.5A patent/CN111593045A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102757988A (en) * | 2012-07-25 | 2012-10-31 | 浙江大学 | Preparation method of 1,3-dioleoyl-2-palmitoyl triglyceride |
| CN104313010A (en) * | 2014-11-05 | 2015-01-28 | 太原理工大学 | Preparation method of magnetic response composite lipase and application in biodiesel synthesis |
| CN105602931A (en) * | 2016-03-11 | 2016-05-25 | 东北农业大学 | Method for synthesizing carbon chain triacylglycerol under supercritical CO2 system based on magnetic immobilized enzyme method |
| CN109251943A (en) * | 2018-08-28 | 2019-01-22 | 江苏大学 | A kind of supercritical CO2Under the conditions of the enzymatic method for preparing OPO structured lipid |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113174384A (en) * | 2021-04-02 | 2021-07-27 | 仲恺农业工程学院 | Immobilized enzyme, preparation method thereof and application thereof in OPO preparation |
| CN113174384B (en) * | 2021-04-02 | 2023-02-03 | 仲恺农业工程学院 | Immobilized enzyme, preparation method thereof and application thereof in OPO preparation |
| CN113980951A (en) * | 2021-11-23 | 2022-01-28 | 东北农业大学 | Immobilized CALB preparation method based on nano dialdehyde starch carrier |
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