CN1693472A - New separation technology of vitamin E, sterol and sterol ester in vegetable oil deodorization distillate - Google Patents
New separation technology of vitamin E, sterol and sterol ester in vegetable oil deodorization distillate Download PDFInfo
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Abstract
A process for separating VE, sterol and sterolester from the deodored distillate of plant oil features that the sterol is separated out by directly dynamic crystallizing, the lipase is used to convert the fatty acid in oil and the neutral oil to methylester of fatty acid, and the molecular distillation is used to separate high-purity methylester of fatty acid and VE.
Description
Technical field
The present invention relates to the method for separating and processing of plant oil deodorizing distillate effective constituent, relate in particular to fatty acid methyl ester in the plant oil deodorizing distillate, sterol, the separating process of sterol ester and vitamin-E.
Background technology
Plant oil deodorizing distillate is the mixture of vegetables oil resulting each cut in deodorising process.Wherein mainly contain abundant fatty acid, tocopherol, sterol and sterol ester, glyceryl ester, vitamin-E and other components etc.
Natural VE has Green Tea Extract, anti-ageing, improve many important physical functions such as physical efficiency immunologic function of human body and animal, human body is had no side effect, the security of its life-time service is far above synthesising complex E, therefore, and at food, dietary supplements industry, natural VE are subjected to extensive favor.Sterol ester and sterol are the materials that a class has physiologically active, and curative effect such as have tangible decreasing cholesterol, anti-inflammatory, bring down a fever applies to industries such as medicine, food, makeup widely.And that sterol ester has than sterol is bigger fat-soluble, has expanded the use range of plant sterol greatly.Biofuel is with low-carbon alcohol synthetic fatty acid esters such as animal-plant oil or longer chain fatty acid and methyl alcohol, is a kind of substitute energy, and the grease after this modification has the physico-chemical property quite similar with diesel oil, and burning fully, non-pollution discharge.
The utilization of plant oil deodorizing distillate at present mainly concentrates on separating of natural VE and plant sterol.Based on vitamin-E, sterol and fatty acid monoester are easy to isolating characteristics, general all is that free fatty acid in the deodorization distillate and neutral grease are converted into fatty acid monoester, thereby realize separating of vitamin-E and sterol, its molecular distillation operational path is normally: with the plant oil deodorizing distillate is raw material, adopt the 2%-6% concentrated sulfuric acid catalyst, add a certain amount of methyl alcohol, under 40-60 ℃ of temperature, carry out esterification, the Crystallization Separation sterol, washing and drying can prepare the vitamin-E of purity 30% by the molecular distillation technology, and the rate of recovery is lower.Be the method in the open book of Chinese invention patent of CN1074217 as publication number, adopt vitriol oil esterification, alcoholysis, washing, technologies such as drying are carried out the vitamin-E that molecular distillation obtains 7-35% again.Although publication number is to have used enzyme esterification techniques and conventional distillation technique in the patent of invention book of CN1563399, the activeconstituents that does not relate in the deodorization distillate separates, and exists separated portion single.
The utilization of plant oil deodorizing distillate at present mainly concentrates on and uses the strong acid and strong base catalytic esterification, utilization molecular distillation or supercritical extraction technique separating VE and sterol, this technology exists ripe relatively, to characteristics such as equipment requirements are simple, but whole process unit operation is more, labour intensity is big, and environmental pollution is serious.And product purity is lower, the product simplification.
Summary of the invention
The present invention aims to provide and a kind ofly is catalyzer, adopts separating technology step by step with fat (Candida Rugosa), can obtain sterol respectively, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate of sterol ester, fatty acid methyl ester and vitamin-E.
The concrete processing method that realizes the foregoing invention purpose is as follows:
1, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate is characterized in that: comprise following four procedures:
A, plant oil deodorizing distillate is dissolved in acetone-methanol mixed solvent, dynamic crystallization is removed sterol;
B, the solution that will remove sterol carry out molecular distillation, obtain light constituent and heavy constituent respectively;
C, lipase hydrolysis is carried out in heavy constituent, obtain sterol ester;
D, light constituent is carried out lipase transesterificationization and molecular distillation, obtain vitamin-E and fatty acid methyl ester.
2, according to vitamin-E, sterol and sterol ester separating technology in the above-mentioned 1 described plant oil deodorizing distillate, it is characterized in that:
A, the plant oil deodorizing distillate of getting about 200g are dissolved in 500-600ml acetone-methanol mixed solvent, begin from 45-50 ℃ of temperature, slowly decrease temperature crystalline is extremely about-5 ℃, crystallization time 20 hours, take out suction filtration and separate thick sterol, repeated as above crystallization operation once more 4 hours; After filtered liquid boiled off solvent, solvent carried out recycle;
B, the solution that will boil off behind the solvent carry out molecular distillation, and distillation temperature 220-240 ℃, working pressure 0.01-0.02torr, feeding temperature 80-90 ℃, obtain the weight component under the rotating speed 140-180r/min condition, heavy constituent mainly contain sterol ester, sweet three esters and the sweet diester of part; Light constituent mainly contains lipid acid, vitamin-E, mono-glycerides, the sweet diester of part and a small amount of sterol;
C, get the heavy constituent of the 20g left and right sides, 20-24ml water, the lipase of 400u/g 33 ℃ of-37 ℃ of following hydrolysis, adds the sodium hydroxide washing of the 0.5mol/1 of 20ml-35ml, removes lipid acid, the distillation washing ,-55 ℃ of frozen dryings separate obtaining sterol ester.
D, get 20g left and right sides light constituent, 3ml-5ml water, 300-500u/g lipase was at 33 ℃ of-37 ℃ of following hydrolysis reaction 12-16 hours; Add 2ml methyl alcohol, 300-500u lipase transesterification 18-24 hour, reaction times 30-40 hour altogether.The reactant layering is anhydrated,-55 ℃ of frozen dryings, carry out molecular distillation, distillation temperature 100-130 ℃, feeding temperature 60-80 ℃, working pressure 0.03-0.04torr, the light constituent that distills out is fatty acid methyl ester, residual solution is carried out repeatedly according to above-mentioned transesterification condition, can get 50% vitamin-E and 90% fatty acid methyl ester by molecular distillation.
3, according to vitamin-E, sterol and sterol ester separating technology in the above-mentioned 2 described plant oil deodorizing distillates, it is characterized in that: the volumetric mixture ratio of described acetone-methanol mixed solvent is 4: 1v/v.
4, according to vitamin-E, sterol and sterol ester separating technology in the above-mentioned 2 described plant oil deodorizing distillates, it is characterized in that: described lipase is lipase from candida sp (Candida rugosa lipase).
Though the wide material sources of lipase, its catalysis characteristics of the lipase of different sources is different with range of application.Lipase from candida sp (Candida rugosa) can keep vigor preferably in water and organic system.It is also relatively more rare at home to use relevant report for lipase from candida sp (Candida rugosa) at present.The best pH value of this kind lipase effect: 7.0; 37 ℃ of optimum tempss, enzyme are lived: 760U/mg (enzyme activity unit is defined as about 37 ℃, during PH7.2, and the amount of 1 micromole's lipid acid in the hydrolysis sweet oil in 1 hour).What we used is the thick enzyme of the commercial enzyme type VII of U.S. sigma company.
5, according to vitamin-E, sterol and sterol ester separating technology in the above-mentioned 2 described plant oil deodorizing distillates, it is characterized in that: the thick sterol that will obtain utilizes the acetone soln dynamic crystallization, promptly from about 50 ℃, slowly drop to-5 ℃, repeat crystallization operation, can obtain the sterol of purity 95%.
Useful technique effect of the present invention is embodied in following aspect:
1, the present invention utilizes lipase to replace conventional strong acid and strong base, utilization lipase technology is converted into fatty acid methyl ester with lipid acid in the grease and neutral grease, make to be reflected under the gentle environment and carry out, help the recovery and the utilization of vitamin-E, simplified reactions steps greatly, the vitamin-E loss is little, does not have environmental pollution, and also more convenient for follow-up separation.And be easy to from reaction system, separate as the lipase of catalyzer, can repeatedly recycle.
2, the present invention combines molecular distillation and lipase technology, and lipid acid in the grease and neutral grease are converted into fatty acid methyl ester, reaches 80% according to this processing condition sterol ester purity, has expanded the use range of sterol.Distillatory light constituent-biofuel (fatty acid methyl ester) is analyzed by GC-MS, and purity reaches more than 90%, and part character is similar to 0 diesel oil of China, can be used as one of source of China's biofuel.Distillatory vitamin-E purity can reach more than 50%, and the rate of recovery is more than 80%.
3, the inventive method is applicable to the separating treatment of the deodorization distillate effective constituent of rapeseed oil, soybean oil, wheatgerm oil and corn wet goods vegetables oil.
Description of drawings
Fig. 1 is a process route chart of the present invention.
Embodiment
Below in conjunction with accompanying drawing, the present invention is further described by embodiment:
Embodiment:
Referring to Fig. 1, with the rapeseed oil deodorization distillate is raw material, by the direct sterols separated of crystallization in motion, normal temperature and pressure adopts the lipase technology generation for strong acid and strong base catalysis down then, is separation method sterols separated ester crude product with the molecular distillation technique, and lipid acid and neutral grease in the distillation distillate are converted into fatty acid methyl ester, and then utilize molecular distillation to obtain biofuel, vitamin-E, the green sub that realizes the grease byproduct is from, comprehensive utilization.
Concrete processing step is as follows:
The first step, got the 500-600ml acetone that the rapeseed oil deodorization distillate about 200g is dissolved in-methanol mixed solvent (4: 1, v/v) in, begin 45-50 ℃ of temperature, slowly decrease temperature crystalline is to about-5 ℃, crystallization time 20 hours, take out suction filtration and separate thick sterol, repeat as above crystallization operation 4 hours once more to separate fully as far as possible.After filtered liquid boiled off solvent, solvent carried out recycle.The thick sterol that obtains utilizes the acetone soln dynamic crystallization, and temperature condition repeats crystallization operation for slowly to drop to-5 ℃ from about 50 ℃, can obtain highly purified sterol.
Second solution that goes on foot, will boil off behind the solvent carries out molecular distillation, and distillation temperature 220-240 ℃, working pressure 0.01-0.02torr, feeding temperature 80-90 ℃, obtain the weight component under the rotating speed 140-180r/min condition, heavy constituent mainly contain sterol ester, sweet three esters and the sweet diester of part.Light constituent mainly contains lipid acid, vitamin-E, mono-glycerides, the sweet diester of part and a small amount of sterol.
The 3rd step, heavy constituent utilization lipase technical point are from sterol ester, get the heavy constituent of the 20g left and right sides, 20-24ml water, (enzyme activity unit is defined as about 37 ℃, during PH7.2 the lipase of 300-400u/g, the amount of 1 micromole's lipid acid in the hydrolysis sweet oil in 1 hour), 33 ℃ of-37 ℃ of following hydrolysis, the sodium hydroxide that adds the 0.5mol/l of 20ml-35ml is removed lipid acid, the distillation washing,-55 ℃ of frozen dryings separate obtaining sterol ester.
The 4th step, light constituent utilization lipase technology are carried out transesterigfication, get 20g left and right sides light constituent, 3ml-5ml water, and 300-500u/g lipase was at 33 ℃ of-37 ℃ of following hydrolysis reaction 12-16 hours; Then add 2ml methyl alcohol, 300-500u lipase transesterification 18-24 hour, reaction times 30-40 hour altogether.The reactant layering is anhydrated,-55 ℃ of frozen dryings, carry out molecular distillation, distillation temperature 100-130 ℃, feeding temperature 60-80 ℃, working pressure 0.03-0.04torr, the light constituent that distills out is fatty acid methyl ester, residual solution is carried out repeatedly according to above-mentioned transesterification condition, can get vitamin-E about 50% and 90% fatty acid methyl ester by molecular distillation.
Claims (5)
1, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate is characterized in that:
Comprise following four procedures:
A, plant oil deodorizing distillate is dissolved in acetone-methanol mixed solvent, dynamic crystallization is removed sterol;
B, the solution that will remove sterol carry out molecular distillation, obtain light constituent and heavy constituent respectively;
C, lipase hydrolysis is carried out in heavy constituent, obtain sterol ester;
D, light constituent is carried out lipase transesterificationization and molecular distillation, obtain vitamin-E and fatty acid methyl ester.
2, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate according to claim 1 is characterized in that:
A, the plant oil deodorizing distillate of getting about 200g are dissolved in 500-600ml acetone-methanol mixed solvent, begin from 45-50 ℃ of temperature, slowly decrease temperature crystalline is extremely about-5 ℃, crystallization time 20 hours, take out suction filtration and separate thick sterol, repeated as above crystallization operation once more 4 hours; After filtered liquid boiled off solvent, solvent carried out recycle;
B, the solution that will boil off behind the solvent carry out molecular distillation, and distillation temperature 220-240 ℃, working pressure 0.01-0.02torr, feeding temperature 80-90 ℃, obtain the weight component under the rotating speed 140-180r/min condition, heavy constituent mainly contain sterol ester, sweet three esters and the sweet diester of part; Light constituent mainly contains lipid acid, vitamin-E, mono-glycerides, the sweet diester of part and a small amount of sterol;
C, get the heavy constituent of the 20g left and right sides, 20-24ml water, the lipase of 400u/g 33 ℃ of-37 ℃ of following hydrolysis, adds the sodium hydroxide washing of the 0.5mol/l of 20ml-35ml, removes lipid acid, the distillation washing ,-55 ℃ of frozen dryings separate obtaining sterol ester.
D, get 20g left and right sides light constituent, 3ml-5ml water, 300-500u/g lipase was at 33 ℃ of-37 ℃ of following hydrolysis reaction 12-16 hours; Add 2ml methyl alcohol, 300-500u lipase transesterification 18-24 hour, reaction times 30-40 hour altogether.The reactant layering is anhydrated,-55 ℃ of frozen dryings, carry out molecular distillation, distillation temperature 100-130 ℃, feeding temperature 60-80 ℃, working pressure 0.03-0.04torr, the light constituent that distills out is fatty acid methyl ester, residual solution is carried out repeatedly according to above-mentioned transesterification condition, can get 50% vitamin-E and 90% fatty acid methyl ester by molecular distillation.
3, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate according to claim 2, it is characterized in that: the volumetric mixture ratio of described acetone-methanol mixed solvent is 4: 1v/v.
4, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate according to claim 2, it is characterized in that: described lipase is lipase from candida sp.
5, vitamin-E, sterol and sterol ester separating technology in the plant oil deodorizing distillate according to claim 2, it is characterized in that: the thick sterol that will obtain utilizes the acetone soln dynamic crystallization, promptly from about 50 ℃, slowly drop to-5 ℃, repeat crystallization operation, can obtain the sterol of purity 95%.
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| WO2007068137A1 (en) * | 2005-11-17 | 2007-06-21 | The Chinese University Of Hong Kong | The process for preparing biodiesel |
| CN101845473A (en) * | 2010-06-03 | 2010-09-29 | 江南大学 | Method for effectively synthesizing phytosterol ester |
| CN102703557A (en) * | 2012-06-14 | 2012-10-03 | 华南理工大学 | Preparation method for phytosterol acetate formed by catalytic synthesis through enzymic method |
| CN102807547A (en) * | 2012-07-14 | 2012-12-05 | 淮北志强油脂有限公司 | New process for extracting vitamin E and sterol from soybean oil deodorization distillate |
| CN105315254A (en) * | 2015-11-25 | 2016-02-10 | 新疆百禾晶生物科技有限公司 | Method for extracting Vitamin E from tomato seed oil deodorized distillate based on enzymic method |
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| CN107012177A (en) * | 2017-03-31 | 2017-08-04 | 福建省格兰尼生物工程股份有限公司 | A kind of method of low-temperature catalyzed deodorization distillate esterification |
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| CN1418877A (en) * | 2002-12-06 | 2003-05-21 | 武汉凯迪精细化工有限公司 | Process for extracting vitamin E from plant-oil debrominated distillate |
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| CN101845473A (en) * | 2010-06-03 | 2010-09-29 | 江南大学 | Method for effectively synthesizing phytosterol ester |
| CN102703557A (en) * | 2012-06-14 | 2012-10-03 | 华南理工大学 | Preparation method for phytosterol acetate formed by catalytic synthesis through enzymic method |
| CN102807547A (en) * | 2012-07-14 | 2012-12-05 | 淮北志强油脂有限公司 | New process for extracting vitamin E and sterol from soybean oil deodorization distillate |
| CN102807547B (en) * | 2012-07-14 | 2015-03-04 | 淮北志强油脂有限公司 | New process for extracting vitamin E and sterol from soybean oil deodorization distillate |
| CN107249343A (en) * | 2015-02-17 | 2017-10-13 | 酶学技术有限公司 | Oil mixture, its preparation method and its application in formula milk |
| WO2016132354A1 (en) * | 2015-02-17 | 2016-08-25 | Enzymotec Ltd. | Oil blends, processes for the preparation thereof and their use in formulas |
| US10993456B2 (en) | 2015-02-17 | 2021-05-04 | Enzymotec Ltd. | Oil blends, processes for the preparation thereof and their use in formulas |
| CN105315254A (en) * | 2015-11-25 | 2016-02-10 | 新疆百禾晶生物科技有限公司 | Method for extracting Vitamin E from tomato seed oil deodorized distillate based on enzymic method |
| CN107012177A (en) * | 2017-03-31 | 2017-08-04 | 福建省格兰尼生物工程股份有限公司 | A kind of method of low-temperature catalyzed deodorization distillate esterification |
| CN108530507A (en) * | 2018-04-11 | 2018-09-14 | 江苏科鼐生物制品有限公司 | A kind of method and system of saponifiable extraction phytosterol |
| CN108530507B (en) * | 2018-04-11 | 2021-03-16 | 江苏科鼐生物制品有限公司 | Method and device for preparing phytosterol |
| CN108771881A (en) * | 2018-06-21 | 2018-11-09 | 江苏科鼐生物制品有限公司 | The multistage steam stripped method and system of vitamin E accessory substance aliphatic acid solvent low-residual |
| CN108912089A (en) * | 2018-06-21 | 2018-11-30 | 江苏科鼐生物制品有限公司 | A kind of method and its crystallization filtering association system of 50VE and sterol centrifuge separation |
| CN108771881B (en) * | 2018-06-21 | 2021-03-16 | 江苏科鼐生物制品有限公司 | Method and system for low-residue multistage steam stripping of vitamin E byproduct fatty acid solvent |
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| CN110257445A (en) * | 2019-06-28 | 2019-09-20 | 中粮天科生物工程(天津)有限公司 | Biodiesel, the method for natural VE and phytosterol are prepared from plant oil deodorizing distillate |
| CN115747266A (en) * | 2023-01-05 | 2023-03-07 | 苏州丰倍生物科技股份有限公司 | Method for producing fatty acid methyl ester by lipase catalysis |
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