CN111187800A - Method for efficiently synthesizing phytosterol ester by enzyme method - Google Patents
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- CN111187800A CN111187800A CN202010145635.6A CN202010145635A CN111187800A CN 111187800 A CN111187800 A CN 111187800A CN 202010145635 A CN202010145635 A CN 202010145635A CN 111187800 A CN111187800 A CN 111187800A
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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
- C12P33/00—Preparation of steroids
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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
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- 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 the technical field of synthesis, and discloses a method for efficiently synthesizing phytosterol ester by an enzyme method. The method for efficiently synthesizing phytosterol ester by using the enzyme method comprises the following steps: (1) adding an organic solvent, an alkaline ionic liquid and immobilized lipase into a reactor, heating, adding fatty acid and phytosterol under the condition of heat preservation, and carrying out ultrasonic radiation under stirring to carry out esterification reaction; (2) and after the reaction is finished, filtering to remove the immobilized lipase, adding a decolorizing agent into the filtrate, stirring for decolorizing, filtering to remove the decolorizing agent, extracting and recovering the organic solvent and the alkaline ionic liquid, and then adding a neutralizing agent to remove unreacted fatty acid to obtain the phytosterol ester. The method is simple and efficient, the yield is up to 95%, the reaction temperature is low, the residual quantity of the organic solvent is low, and the purity of the obtained phytosterol ester is up to 98%.
Description
Technical Field
The invention relates to the technical field of synthesis, and discloses a method for efficiently synthesizing phytosterol ester by an enzyme method.
Background
Phytosterols are naturally occurring substances that are present in food as trace components of vegetable oils. The effect of phytosterols in plants is similar to that of cholesterol in mammals, such as the formation of cell membrane tissue. For human body, phytosterol has a remarkable hypolipidemic effect, which has been proved by a great deal of research. However, since phytosterols are insoluble in water, their solubility in the oil phase is also quite limited, which limits their use. For many years, attempts have been made to modify phytosterols to expand their range of application. Since the early 90 s abroad, approaches for applying the phytosterol have been explored, and various phytosterol products have been developed through purification and modification. Among the most important modification means to esterify phytosterols to steryl esters, the common foods containing phytosterol esters that can be obtained are mainly oils, margarines and certain dairy products. In addition to these applications, the combination of phytosterol esters with nutritional products is also of great importance, for example to provide a dietary alternative for the prophylactic treatment of hypercholesterolemia in the early stages of the normal population, and in the case of severe hypercholesterolemia in combination with statins, for the prophylactic treatment of serum cholesterol lowering.
To date, several attempts have been made to convert phytosterols to phytosterol esters in an attempt to expand their production and use. For example, US20020098536 discloses a method for producing mixed fatty acid sterol ester by using soybean oil deodorizer as raw material (deodorizer can be directly used as reaction raw material without separation, and pure sterol and fatty acid are not used as raw material), and lipase catalyzes transesterification of phytosterol and triglyceride to produce mixed fatty acid sterol ester, wherein the method has low raw material cost, but the catalytic activity is low, the inactivation is easy, and the industrial requirement cannot be met; for another example, CN101235067 discloses a method for synthesizing sterol ester by directly esterifying fatty acid and phytosterol, wherein the catalyst is calcium oxide, magnesium oxide, lanthanum oxide, etc., wherein the calcium oxide and the magnesium oxide react with the fatty acid to form soap, which results in complex subsequent processes.
Generally, the current methods for preparing phytosterol esters fall into two broad categories, chemical and biological. The chemical method has the advantages of multiple reaction steps, high energy consumption, poor selectivity, easy damage of beneficial components in a high-temperature environment, easy generation of metal ion residues in the preparation process, easy darkening of the prepared sterol ester, generation of harmful oxidation byproducts, and environmental pollution caused by a large amount of generated waste liquid. Although the biological enzyme method has mild reaction environment, simple and controllable process, higher regioselectivity and fewer byproducts, an organic solvent system needs to be adopted, and the use of the organic solvent is accompanied by a plurality of disadvantages, such as: is easy to volatilize, is easy to pollute the environment, has poor safety, and the residual organic solvent can also reduce the quality of the product, etc.
Disclosure of Invention
The invention aims to overcome the defects of the background technology and provide a novel method for efficiently synthesizing phytosterol ester by an enzyme method, wherein the method is simple and efficient, the yield is as high as 95%, the reaction temperature is low, the residual quantity of organic solvent is low, and the purity of the obtained phytosterol ester is as high as 98%.
In order to achieve the purpose of the invention, the method for efficiently synthesizing the phytosterol ester by the enzyme method comprises the following steps:
(1) adding an organic solvent, an alkaline ionic liquid and immobilized lipase into a reactor, heating, adding fatty acid and phytosterol under the condition of heat preservation, and carrying out ultrasonic radiation under stirring to carry out esterification reaction;
(2) and after the reaction is finished, filtering to remove the immobilized lipase, adding a decolorizing agent into the filtrate, stirring for decolorizing, filtering to remove the decolorizing agent, extracting and recovering the organic solvent and the alkaline ionic liquid, and then adding a neutralizing agent to remove unreacted fatty acid to obtain the phytosterol ester.
Further, the phytosterol is one or more of sitosterol, stigmasterol, campesterol and brassicasterol.
Preferably, the total plant sterol content in the plant sterol is above 90%.
Further, the fatty acid is one or more of myristic acid, caproic acid, caprylic acid, lauric acid, palmitic acid, oleic acid, linoleic acid, docosahexaenoic acid or stearic acid.
Further, the molar ratio of the fatty acid to the phytosterol is 1.5-2: 1.
further, the immobilized lipase is one or more of Lipozyme435 and Novozyme 435.
Further, the mass of the immobilized lipase is 3-6% of that of the phytosterol and is 1.5-3% of that of the alkaline ionic liquid.
Generally, increasing the temperature of the esterification reaction system is beneficial to improving the reaction efficiency and promoting the enzyme catalysis reaction, but too high temperature in the esterification reaction can lead to dehydration of alcohol, hydrolysis of ester, more by-products (phytosterol is easily oxidized at the temperature higher than 85 ℃), and the like, and too high temperature is not suitable for industrial mass production, so that the resource consumption is high, and the requirements on equipment are also high, and the organic solvent of the reaction system in the invention is preferably one or more of tert-amyl alcohol, tert-butyl alcohol, isobutyl alcohol and n-hexyl alcohol; in the reaction system, the temperature for preparing the phytosterol by the enzyme method can be 30-50 ℃, and preferably 30-40 ℃.
The esterification is a reversible reaction, so that the concentration of a reaction substrate is improved, the reaction is favorably carried out in a forward direction, and the product yield is improved. And (3) continuing the reaction after the ultrasonic radiation lasts for 0.5-3h at the temperature of 30-50 ℃, wherein the reaction time is 3-6h, the stirring is maintained in the whole reaction process, and the stirring speed is 200-350 rpm.
Preferably, the ultrasonic generator of the ultrasonic radiation has a frequency of 15-30kHz and a power of 80-200W.
Further, the alkaline ionic liquid is one or more of 1-ethyl-3-methyl-imidazole acetate ionic liquid, 1-butyl-3-methyl-imidazole carbonate ionic liquid or 1-butyl-3-methyl-imidazole bicarbonate ionic liquid.
Further, the volume ratio of the basic ionic liquid to the organic solvent is 3: 1-2.
Compared with the prior art, the method for efficiently synthesizing phytosterol ester by the enzyme method avoids the defects of high energy consumption and more byproducts of a chemical method. In the organic solvent and the alkaline ionic liquid, the ultrasonic radiation is carried out while the enzymatic catalysis is carried out, the reaction condition is mild, but the efficiency is high, the energy consumption is low, the purity of the obtained phytosterol ester product is high, the solvent used in the reaction process can be recycled, the immobilized lipase can be recycled for multiple batches, and the method is economical and environment-friendly.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. Additional aspects and advantages of the invention will be set forth in part in the description which follows and, in part, will be obvious from the description, or may be learned by practice of the invention. It is to be understood that the following description is only illustrative of the present invention and is not to be construed as limiting the present invention.
The indefinite articles "a" and "an" preceding an element or component of the invention are not intended to limit the number requirement (i.e., the number of occurrences) of the element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural unless the number clearly indicates the singular. If not specifically stated, the total phytosterol content in the phytosterol is more than 90%, the frequency of an ultrasonic generator of the ultrasonic radiation is 15-30kHz, and the power is 80-200W.
Example 1
Adding n-hexanol, 1-ethyl-3-methyl-imidazole acetate ionic liquid and immobilized lipase Novozyme435 into a reaction container, heating to 30 ℃, adding 320g of phytosterol and 285g of oleic acid under the condition of heat preservation, carrying out ultrasonic radiation under stirring, keeping the reaction for 5h after 1h of ultrasonic radiation, and keeping stirring in the whole reaction process at the stirring speed of about 250 rpm. Wherein the mass of the immobilized lipase Novozyme435 is 4% of that of the phytosterol, the immobilized lipase Novozyme is 2% of that of the 1-ethyl-3-methyl-imidazole acetate ionic liquid, and the volume ratio of the 1-ethyl-3-methyl-imidazole acetate ionic liquid to isobutanol is 2: 1. after the reaction is finished, filtering to remove immobilized lipase, adding a decolorizing agent into the filtrate, stirring and decolorizing, filtering to remove the decolorizing agent, extracting and recovering n-hexanol and 1-ethyl-3-methyl-imidazole acetate ionic liquid, adding a neutralizing agent to remove unreacted fatty acid to obtain phytosterol ester, wherein the conversion rate of the phytosterol is 91%, and the purity of the phytosterol ester reaches 98.2% by GC-MS (gas chromatography-mass spectrometry).
Example 2
Adding n-hexanol, 1-ethyl-3-methyl-imidazole acetate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 35 ℃, and obtaining phytosterol ester by the same reaction conditions as in example 1, wherein the conversion rate of the phytosterol is 96%, and the purity of the phytosterol ester reaches 98.7% by GC-MS (gas chromatography-Mass Spectrometry).
Example 3
Adding n-hexanol, 1-ethyl-3-methyl-imidazole acetate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 40 ℃, and obtaining phytosterol ester by the same reaction conditions as in example 1, wherein the conversion rate of the phytosterol is 96%, and the purity of the phytosterol ester reaches 98.9% by GC-MS (gas chromatography-Mass Spectrometry).
Example 4
Adding n-hexanol, 1-ethyl-3-methyl-imidazole acetate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 45 ℃, and performing other reaction conditions in the same way as in example 1 to finally obtain the phytosterol ester, wherein the conversion rate of the phytosterol is 95%, and the purity of the phytosterol ester reaches 96.8% as determined by GC-MS.
Example 5
Adding n-hexanol, 1-ethyl-3-methyl-imidazole acetate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 50 ℃, and performing other reaction conditions in the same way as in example 1 to finally obtain the phytosterol ester, wherein the conversion rate of the phytosterol is 92%, and the purity of the phytosterol ester is 91.2% by GC-MS (gas chromatography-Mass spectrometer).
Example 6
Adding tert-amyl alcohol, 1-octyl-3-methylimidazolium hexafluorophosphate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 35 ℃, and obtaining phytosterol ester by the same reaction conditions as in example 2, wherein the conversion rate of the phytosterol is 89%, and the purity of the phytosterol ester reaches 96.1% by GC-MS.
Example 7
Adding 1-ethyl-3-methyl-imidazole acetate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 35 ℃, and obtaining phytosterol ester by other reaction conditions in the same way as in example 2, wherein the conversion rate of phytosterol is 78%, and the purity of the phytosterol ester reaches 96.7% by GC-MS (gas chromatography-Mass Spectrometry).
Example 8
Adding 1-octyl-3-methylimidazolium hexafluorophosphate ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 35 ℃, and performing other reaction conditions in the same way as in example 2 to finally obtain the phytosterol ester, wherein the conversion rate of the phytosterol is 71%, and the purity of the phytosterol ester reaches 95.2% by GC-MS.
Example 9
Adding n-hexanol, 1-ethyl-3-methylimidazole hydroxide ionic liquid and immobilized lipase Novozyme435 into a reaction vessel, heating to 35 ℃, and performing other reaction conditions in the same way as in example 2 to finally obtain the phytosterol ester, wherein the conversion rate of the phytosterol is 88%, and the purity of the phytosterol ester reaches 96.1% by GC-MS (gas chromatography-Mass Spectrometry).
It will be understood by those skilled in the art that the foregoing is only exemplary of the present invention, and is not intended to limit the invention, which is intended to cover any variations, equivalents, or improvements therein, which fall within the spirit and scope of the invention.
Claims (10)
1. A method for efficiently synthesizing phytosterol ester by an enzyme method is characterized by comprising the following steps:
(1) adding an organic solvent, an alkaline ionic liquid and immobilized lipase into a reactor, heating, adding fatty acid and phytosterol under the condition of heat preservation, stirring, and performing ultrasonic radiation to perform esterification reaction;
(2) and after the reaction is finished, filtering to remove the immobilized lipase, adding a decolorizing agent into the filtrate, stirring for decolorizing, filtering to remove the decolorizing agent, extracting and recovering the organic solvent and the alkaline ionic liquid, and then adding a neutralizing agent to remove unreacted fatty acid to obtain the phytosterol ester.
2. The method for efficiently synthesizing phytosterol ester by using the enzyme method according to claim 1, wherein the phytosterol is one or more of sitosterol, stigmasterol, campesterol and brassicasterol.
3. The method for efficiently synthesizing phytosterol ester by using enzyme according to claim 1, wherein the fatty acid is one or more of myristic acid, caproic acid, caprylic acid, lauric acid, palmitic acid, oleic acid, linoleic acid, docosahexaenoic acid or stearic acid.
4. The method for efficiently synthesizing phytosterol ester by using the enzyme method according to claim 1, wherein the molar ratio of the fatty acid to the phytosterol is 1.5-2: 1.
5. the method for efficiently synthesizing phytosterol ester by using the enzyme method according to claim 1, wherein the immobilized lipase is one or more of Lipozyme435 and Novozyme 435.
6. The method for efficiently synthesizing phytosterol ester by using the enzyme method according to claim 5, wherein the mass of the immobilized lipase is 3-6% of that of the phytosterol and is 1.5-3% of that of the alkaline ionic liquid.
7. The method for efficiently synthesizing phytosterol ester by using the enzyme method according to claim 1, wherein the organic solvent is one or more of tertiary amyl alcohol, tertiary butyl alcohol, isobutyl alcohol and n-hexyl alcohol.
8. The method for efficiently synthesizing phytosterol ester by enzyme method according to claim 1, wherein the heating is carried out to the temperature of 30-50 ℃, preferably 30-40 ℃.
9. The method for efficiently synthesizing phytosterol ester by the enzyme method according to claim 1, wherein the reaction is continued after the ultrasonic radiation lasts for 0.5-3h, the reaction time is 3-6h, the stirring is maintained in the whole reaction process, and the stirring speed is 200-350 rpm; preferably, the ultrasonic generator of the ultrasonic radiation has a frequency of 15-30kHz and a power of 80-200W.
10. The method for efficiently synthesizing phytosterol ester by using the enzyme method according to claim 1, wherein the alkaline ionic liquid is one or more of 1-ethyl-3-methyl-imidazole acetate ionic liquid, 1-butyl-3-methyl-imidazole carbonate ionic liquid or 1-butyl-3-methyl-imidazole bicarbonate ionic liquid; preferably, the volume ratio of the basic ionic liquid to the organic solvent is 3: 1-2.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111848715A (en) * | 2020-09-07 | 2020-10-30 | 广州善合化工有限公司 | Preparation method and application of phytosterol isostearate |
| CN113150055A (en) * | 2021-03-31 | 2021-07-23 | 右江民族医学院 | High-efficiency synthesis method of stigmasterol ester |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040105931A1 (en) * | 2000-04-04 | 2004-06-03 | Sobhi Basheer | Enzymatic modification of sterols using sterol-specific lipase |
| CN102618615A (en) * | 2012-04-06 | 2012-08-01 | 中国农业科学院油料作物研究所 | Enzymatic synthesis method of phytosterol ester/phytostanol ester by utilizing ultrasonic enhancement |
| CN104372059A (en) * | 2014-11-11 | 2015-02-25 | 华南理工大学 | Catalytic synthesis method of sterol ester in ionic liquid microemulsion phase enzymatic catalytic system |
| CN107937470A (en) * | 2017-12-12 | 2018-04-20 | 江南大学 | A kind of method of enzymatic clarification phytosterin ester in ion liquid system |
-
2020
- 2020-03-05 CN CN202010145635.6A patent/CN111187800B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040105931A1 (en) * | 2000-04-04 | 2004-06-03 | Sobhi Basheer | Enzymatic modification of sterols using sterol-specific lipase |
| CN102618615A (en) * | 2012-04-06 | 2012-08-01 | 中国农业科学院油料作物研究所 | Enzymatic synthesis method of phytosterol ester/phytostanol ester by utilizing ultrasonic enhancement |
| CN104372059A (en) * | 2014-11-11 | 2015-02-25 | 华南理工大学 | Catalytic synthesis method of sterol ester in ionic liquid microemulsion phase enzymatic catalytic system |
| CN107937470A (en) * | 2017-12-12 | 2018-04-20 | 江南大学 | A kind of method of enzymatic clarification phytosterin ester in ion liquid system |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111848715A (en) * | 2020-09-07 | 2020-10-30 | 广州善合化工有限公司 | Preparation method and application of phytosterol isostearate |
| CN113150055A (en) * | 2021-03-31 | 2021-07-23 | 右江民族医学院 | High-efficiency synthesis method of stigmasterol ester |
| CN113150055B (en) * | 2021-03-31 | 2023-04-25 | 右江民族医学院 | Efficient synthesis method of stigmasterol ester |
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