CN108841880B - Preparation method of 1, 3-dioleoyl-2-palmitic acid triglyceride - Google Patents
Preparation method of 1, 3-dioleoyl-2-palmitic acid triglyceride Download PDFInfo
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Abstract
The invention provides a preparation method of 1, 3-dioleic acid-2-palmitic acid triglyceride. The method comprises the steps of mixing palm stearin and palmitic acid, carrying out nitrogen protection, and carrying out catalysis on S of the palm stearin under solid superacidn-2-position palmitic acid is enriched; then acidolysis is carried out on the mixture and oleic acid in a fixed bed reactor under the catalysis of complex enzyme, and crystallization is carried out at low temperature, so as to obtain the high-purity 1, 3-dioleic acid-2-palmitic acid triglyceride. The method has the advantages of cheap and easily-obtained raw materials, simple process, green and environment-friendly catalyst, recycling, low preparation cost, high yield and suitability for industrial production.
Description
Technical Field
The invention belongs to the technical field of grease, and particularly relates to a preparation method of 1, 3-dioleic acid-2-palmitic acid triglyceride.
Background
Breast milk is considered the most nutritious food for newborns, providing the energy, necessary nutrients and immune conditions required for the healthy growth of infants. The breast milk contains 3-5% of fat, more than 98% of the breast milk is triglyceride, 18-25% of the breast milk is 1, 3-dioleoyl-2-palmitoyl triglyceride (1, 3-dioleoyl-2-palmitylglycol, hereinafter referred to as OPO), and the sn-2 position of the OPO is palmitic acid. The OPO is added into the infant formula milk powder to ensure the infant formula milk powder to be 'mother emulsified', so that the healthy growth of the infant can be better ensured. The 2008 Chinese ministry of health approves that the OPO product can be used as a nutrition enhancer in infant formula milk powder, and the content of OPO and PPP is specified.
The palmitic acid in the triglycerides that make up lard is mainly distributed at the Sn-2 position, and the OPO content in the triglyceride composition is significantly higher than other animal fats, similar to the human milk fat composition. Therefore, the presently reported method for preparing OPO mainly uses refined lard as a raw material, and adopts a solvent method to carry out fractionation and enrichment, the lard is melted at 60 ℃, then mixed with acetone according to a ratio of 1:2(w/v), heated at 60 ℃ to become a uniform system, then placed at 10 ℃ for maintaining 24h to crystallize the lard, vacuum filtration is carried out after the crystallization is completed, and the filtrate is decompressed and evaporated to obtain acetone to obtain liquid fat, wherein the OPO purity in the liquid fat is only 30% ("Property analysis of fractionation products by lard solvent method", Zhang Xiaopeng et al, China fat, volume 39, No. 2, pages 37-41, published as 20140220). The method is improved, namely a dry coupling solvent method fractionation process is adopted, and the OPO purity can only reach 43 percent (the physical properties of lard OPO enrichment and lard fractionation components are researched, Zhang Hui and the like, in the grain and food industry, Vol.22, No. 1, published Japanese 20150215). The existing method for extracting and enriching 1, 3-dioleic acid-2-palmitic acid triglyceride (OPO) from lard has the problems of low OPO yield and low purity. In addition, because the popular habit and religion are not suitable for problems, the lard is not used in infant formula in other countries and regions besides the infant formula in individual Japanese brand, so that the market potential of OPO products produced by using the lard is far less than that of products produced by using vegetable oil as a raw material.
Palm oil is an edible vegetable oil widely used in the world, mainly produced in Malaysia, Indonesia, and the like. The palm oil is fractionated to obtain palm liquid oil, palm super liquid oil and palm stearin with different melting points. The content and distribution of fatty acid in different palm oil are greatly different, wherein the content of palmitic acid in palm stearin is the highest and can reach 48-74%, and the palm stearin has high utilization value for synthesizing OPO. Currently, only Swedish Advanced Lipid company and Malaysia Loders Croklaan company produce OPO, and domestic OPO basically depends on import and is high in price.
Disclosure of Invention
The invention aims to provide a novel method for green chemical synthesis of 1, 3-dioleoyl-2-palmitic acid triglyceride, which has the advantages of simple process, low cost, high purity of the synthesized product, high yield and important application value.
The technical scheme adopted by the invention for solving the technical problems is as follows:
a preparation method of 1, 3-dioleoyl-2-palmitic acid triglyceride comprises the following steps:
s1: adding palm stearin and palmitic acid into a three-neck flask, stirring and mixing uniformly at 50-100 ℃ under the protection of nitrogen, then adding a catalyst, and reacting for 4-6h at the reaction temperature of 160-200 ℃;
s2: cooling to room temperature, filtering and recovering the catalyst to obtain a light yellow viscous oily liquid A;
s3: adding a complex enzyme into a fixed bed reactor, adding the liquid A, the oleic acid and the normal hexane obtained in the step S2 into a bottle with a plug connected with the fixed bed reactor, uniformly mixing, starting a peristaltic pump, setting the flow rate to be 10ml/min, setting the temperature to be 45-55 ℃, and carrying out a cyclic reaction for 10-14 hours;
s4: and (2) recovering normal hexane and palmitic acid by reduced pressure distillation, then adding absolute ethyl alcohol, collecting crystalline solid at the temperature of 15-20 ℃, washing the crystalline solid once by using the ethyl alcohol at the temperature of less than or equal to 10 ℃, and drying under reduced pressure to obtain white solid 1, 3-dioleate-2-palmitic acid triglyceride.
The Novozym 435 enzyme is a heat-stable lipase, shows special 1,3 positioning and can hydrolyze triglyceride into glycerol and fatty acid. Pancreatic lipase is an enzyme capable of decomposing fats, hydrolyzing triglycerides into glycerol and fatty acids. The invention adopts a double-enzyme mixing method, and the prepared 1, 3-dioleic acid-2-palmitic acid triglyceride has better yield and higher purity.
Preferably, in the step S1, the mass ratio of the palm stearin to the palmitic acid to the catalyst is 1:0.5-1.5:0.01-0.05, the catalyst is HND-580 solid super acid, the reaction temperature is 160-.
More preferably, in the step S1, the temperature is 180 ℃ and the reaction time is 5 h.
Preferably, in the step S3, the liquid A, the oleic acid and the n-hexane are subjected to cyclic reaction for 10-14h at the temperature of 45-55 ℃ in a mass ratio of 1:7-9: 1.
More preferably, in the step S3, the liquid a, the oleic acid and the n-hexane are cyclically reacted for 12 hours at a temperature of 50 ℃ at a mass ratio of 1:8: 1.
Preferably, in step S3, the composite catalyst is a mixed enzyme composed of dextran glyoxyl-crosslinked Novozyme435 lipase and pancreatic lipase, the mass ratio of the dextran glyoxyl-crosslinked Novozyme435 lipase to the pancreatic lipase is 1:0.5-2.5, and the amount of the composite catalyst is 5-7% of the mass of the liquid a.
More preferably, in step S3, the amount of the composite catalyst is 6% by mass of the liquid a.
Preferably, in step S4, the mass of the absolute ethyl alcohol is 0.5 times the mass of the liquid a.
Preferably, in step S4, the washing is performed by ethanol at a temperature of less than or equal to 10 ℃, and the amount of the ethanol is 0.3 times of the mass of the liquid A.
The Novozyme435 enzyme is Candida antarctica lipase B (namely lipase CAL-B), is immobilized enzyme prepared by adsorption of macroporous adsorption resin, and can generate an enzyme molecule shedding phenomenon in the reaction process, so that the recovery amount of the enzyme is reduced, and the reuse effect of the enzyme is influenced. Therefore, the invention adopts glucan acetaldehyde to combine with amino in enzyme molecules to immobilize the enzyme molecules, thereby improving the stability of the enzyme, and the specific method is as follows:
adding Novozyme435 lipase into glucan diacetal solution with the mass concentration of 0.6-9% in an adding amount of 12-18 g/L, carrying out chemical crosslinking for 15-20min at 25-45 ℃ and 50-200rpm, fully washing unreacted glucan diacetal with distilled water after the crosslinking reaction is finished, and drying to obtain the glucan diacetal crosslinking modified lipase Novozyme435 lipase.
The invention has the beneficial effects that:
1. the synthesis process only needs two steps of reaction, the reaction route is simple, and the reaction yield is high;
2. the used catalyst can be completely recycled, and is economical and environment-friendly;
3. the invention adopts a double-enzyme mixing method, the product purity is higher than 93 percent, and the yield is higher than 94 percent;
4. the method fully utilizes the palmitic acid on the Sn-2 position in the palm stearin to prepare the OPO, has the advantages of common raw materials, low cost and simple process, and is suitable for industrial production.
Detailed Description
The present invention is further explained with reference to the following examples, which are not intended to limit the present invention in any way.
Example 1
(1) Adding 10g of palm stearin and 10g of palmitic acid into a three-neck flask, stirring and mixing uniformly at 70 ℃ under the protection of nitrogen, then adding 0.02g of catalyst, and reacting for 4 hours at 160 ℃;
(2) cooling to room temperature, filtering and recovering the catalyst to obtain a light yellow viscous oily liquid A;
(3) adding 1g of complex enzyme (0.4 g of Novozyme435 lipase containing glucan and diacetal after cross-linking) into a fixed bed reactor, adding 20g of liquid A, 140g of oleic acid and 20g of n-hexane into a bottle with a plug, uniformly mixing, starting a peristaltic pump, setting the flow rate to be 10ml/min and the temperature to be 45 ℃, and carrying out a circular reaction for 10 hours;
(4) distilling under reduced pressure to recover n-hexane and palmitic acid, adding anhydrous ethanol, collecting crystalline solid at a temperature of more than or equal to 15 ℃ and less than or equal to 20 ℃, washing with ethanol at a temperature of less than or equal to 10 ℃, and drying under reduced pressure to obtain white solid. The OPO content by HPLC analysis was 93.6%, yield 94%.
The preparation method of the Novozyme435 lipase after crosslinking of glucan and diacetal comprises the following steps:
adding 15g/L of Novozyme435 lipase into 5% dextran-diacetal solution, carrying out chemical crosslinking at 30 ℃ and 180rpm for 20min, after the crosslinking reaction is finished, sufficiently washing unreacted glutaraldehyde with distilled water, and drying to obtain the dextran-diacetal crosslinking modified lipase Novozyme 435.
Example 2
(1) Adding 10g of palm stearin and 10g of palmitic acid into a three-neck flask, stirring and mixing uniformly at 70 ℃ under the protection of nitrogen, then adding 0.02g of catalyst, and reacting for 5 hours at 180 ℃;
(2) cooling to room temperature, filtering and recovering the catalyst to obtain a light yellow viscous oily liquid A;
(3) adding 0.2 g of complex enzyme (0.08 g of Novozyme435 lipase after crosslinking containing glucan and diacetal) into the fixed bed reactor, adding 20g of liquid A20g, 160g of oleic acid and 20g of n-hexane into a bottle with a plug, uniformly mixing, starting a peristaltic pump, setting the flow rate to be 10ml/min and the temperature to be 50 ℃, and carrying out cyclic reaction for 12 hours;
(4) distilling under reduced pressure to recover n-hexane and palmitic acid, adding anhydrous ethanol, collecting crystalline solid at a temperature of more than or equal to 15 ℃ and less than or equal to 20 ℃, washing with ethanol at a temperature of less than or equal to 10 ℃, and drying under reduced pressure to obtain white solid OPO. The OPO content by HPLC analysis was 96.72% with a yield of 96.11%.
The preparation method of the Novozyme435 lipase after crosslinking of glucan and diacetal comprises the following steps:
adding the Novozyme435 lipase into a glucan diacetal solution with the mass concentration of 0.6% in an adding amount of 12g/L, carrying out chemical crosslinking for 15min at 45 ℃ and 55rpm, after the crosslinking reaction is finished, sufficiently washing off unreacted glutaraldehyde by using distilled water, and drying to obtain the glucan diacetal crosslinking modified lipase Novozyme435 enzyme.
Example 3
(1) Adding 10g of palm stearin and 10g of palmitic acid into a three-neck flask, stirring and mixing uniformly at 70 ℃ under the protection of nitrogen, then adding 0.02g of catalyst, and reacting for 6 hours at 200 ℃;
(2) cooling to room temperature, filtering and recovering the catalyst to obtain a light yellow viscous oily liquid A;
(3) adding 0.4g of complex enzyme (0.16 g of Novozyme435 lipase after crosslinking containing glucan and diethyl aldehyde) into a fixed bed reactor, adding 20g of liquid A, 180g of oleic acid, 20g of n-hexane and 1.4g of complex catalyst into a bottle with a plug, uniformly mixing, starting a peristaltic pump, setting the flow rate to be 10ml/min and the temperature to be 55 ℃, and carrying out cyclic reaction for 14 hours;
(4) distilling under reduced pressure to recover n-hexane and palmitic acid, adding anhydrous ethanol, collecting crystalline solid at a temperature of more than or equal to 15 ℃ and less than or equal to 20 ℃, washing with ethanol at a temperature of less than or equal to 10 ℃, and drying under reduced pressure to obtain white solid OPO. The OPO content by HPLC analysis was 96.67%, yield 96.12%.
The preparation method of the Novozyme435 lipase after crosslinking of glucan and diacetal comprises the following steps:
adding the Novozyme435 lipase into a glucan-diacetal solution with the mass concentration of 5% at the addition of 18g/L, carrying out chemical crosslinking at 25 ℃ for 18min at 150rpm, fully washing unreacted glutaraldehyde by using distilled water after the crosslinking reaction is finished, and drying to obtain the glucan-diacetal crosslinked and modified lipase Novozyme435 enzyme.
The above is merely an illustration of the preferred embodiments of the invention, and the scope of the invention is not limited thereto, and any modifications made by those skilled in the art within the scope of the claims of the invention fall within the scope of the invention.
Claims (8)
1. A preparation method of 1, 3-dioleic acid-2-palmitic acid triglyceride is characterized in that: the preparation method comprises the following steps:
s1, adding the palm stearin and the palmitic acid into a three-neck flask, stirring and mixing the materials uniformly at 50-100 ℃ under the protection of nitrogen, then adding a catalyst, and reacting for 4-6h at the reaction temperature of 160-200 ℃;
s2, cooling to room temperature, filtering and recovering the catalyst to obtain a light yellow viscous oily liquid A;
s3, adding complex enzyme into a fixed bed reactor, adding liquid A, oleic acid and n-hexane into a bottle with a plug connected with the fixed bed reactor, mixing uniformly, starting a peristaltic pump, and performing a cyclic reaction for 10-14h at a set flow rate of 5-15ml/min and a temperature of 45-55 ℃;
s4, carrying out reduced pressure distillation to recover n-hexane and palmitic acid, adding absolute ethyl alcohol, collecting crystalline solids at the temperature of 15-20 ℃, washing the crystalline solids once with the ethyl alcohol at the temperature of less than or equal to 10 ℃, and drying under reduced pressure to obtain 1, 3-dioleate-2-palmitic acid triglyceride;
wherein, in the step S1, the catalyst is HND-580 solid super acid;
in the step S3, the complex enzyme is a mixed enzyme consisting of Novozyme435 lipase and pancreatic lipase after cross-linking of glucan and acetaldehyde.
2. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein: in the step S1, the mass ratio of the palm stearin to the palmitic acid to the catalyst is 1:0.5-1.5:0.01-0.05, the reaction temperature is 180 ℃, and the reaction time is 5 hours.
3. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein: in the step S3, the mass ratio of the liquid A to the oleic acid to the n-hexane is 1:7-9:1, the temperature is 45-55 ℃, and the cyclic reaction time is 10-14 h.
4. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 3, wherein: the mass ratio of the liquid A to the oleic acid to the n-hexane is 1:8:1, the temperature is 50 ℃, and the cyclic reaction time is 12 hours.
5. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein: in the step S3, the mass ratio of the Novozyme435 lipase to the pancreatic lipase after crosslinking and crosslinking of the glucan and the diacetal is 1:0.5-2.5, and the dosage of the composite catalyst is 5-7% of the mass of the liquid A.
6. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 5, wherein: the Novozyme435 lipase after glucan and diacetal crosslinking is prepared by the following method:
adding Novozyme435 lipase into glucan diacetal solution with the mass concentration of 0.6-9% in an adding amount of 12-18 g/L, carrying out chemical crosslinking for 15-20min at 25-45 ℃ and 50-200rpm, fully washing unreacted glucan diacetal with distilled water after the crosslinking reaction is finished, and drying to obtain the glucan diacetal crosslinking modified lipase Novozyme435 lipase.
7. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 5, wherein: the dosage of the composite catalyst is 6 percent of the mass of the liquid A.
8. The process for producing 1, 3-dioleoyl-2-palmitoyl triglyceride according to claim 1, wherein: in step S4, the mass of absolute ethyl alcohol is 0.5 times the mass of liquid a, and the amount of ethyl alcohol is 0.3 times the mass of liquid a.
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