CN104479883A - Preparation method for fatty glyceride - Google Patents
Preparation method for fatty glyceride Download PDFInfo
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- CN104479883A CN104479883A CN201410660183.XA CN201410660183A CN104479883A CN 104479883 A CN104479883 A CN 104479883A CN 201410660183 A CN201410660183 A CN 201410660183A CN 104479883 A CN104479883 A CN 104479883A
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- ester
- fatty acid
- glycerin fatty
- preparation
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Classifications
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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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
-
- 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
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
- C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the fields of food, chemical engineering, medicines and the like, and particularly relates to a preparation method of fatty glyceride. The preparation method of the fatty glyceride comprises the following steps: mixing fatty acid low alcohol ester with glycerol in a molar ratio of 1:2 to 6:1 by taking low alcohol sodium or low alcohol potassium as a catalyst, and reacting for 1-60 hours in vacuum at 100-170 DEG C, thereby obtaining a glyceride crude product; and processing and treating the glyceride crude product subsequently, thereby preparing the corresponding product. The preparation method for fatty glyceride disclosed by the invention can be used for preparing a mixture of monooleoyl glycerol, diacyl glycerol and triglyceride, and has an obvious effect in increasing the yield and improving the product quality.
Description
Technical field
The technology of the present invention relates to food, chemical industry, medicine and other fields, is specially a kind of preparation method of glycerin fatty acid ester.
Background technology
Glyceride product is a kind of primarily of mono-glycerides, triglyceride and triglyceride level composition mixture, be all widely used in food, chemical industry and medicine and other fields.Such as: 1) ministry of Health of China announces triglyceride oil in No. 12 bulletin in 2008 is new resource food, and its composition comprises triglyceride >=40%, triglyceride level≤58%, mono-glycerides≤1.5%, free fatty acids≤0.5%.Triglyceride oil, as a kind of novel healthy grease, is identified as generally recognized as safe material in the U.S., and licensed in Japan is specific food for health care, in Canada by new food safety certification, all assert that it is new food in Australia, New Zealand, European Union.Triglyceride oil at reduction blood fat, prevent artery thrombosis, reduce body fat, etc. in all have obvious effect, and it is assessed as safety, the nontoxic new food of health.2) ministry of Health of China announces conjugated linoleic acid glyceride in No. 12 bulletin in 2009 is new resource food, its specification of quality content of triglyceride 77%-83%, diglyceride content 17%-23%, content of monoglyceride <1%.It can at milk and milk products (except pure breast); Fat, edible oil and emulsified fats-prepd; Beverage class; Frozen; Cocoa products, chocolate and chocolate and candy; Coarse cereal powder and goods thereof; Apply in ready-to-eat cereal, bakery product, coffee.Conjugated linolic acid has the functions such as hypotensive, reducing blood-fat, fat-reducing, immunity moderation power and in widespread attention, the conjugated linolic acid that market is sold is mainly conjugated linolic acid free fatty acids and ethyl ester thereof, but conjugated linoleic acid glyceride has stronger oxidative stability than conjugated linolic acid, also there is the health care characteristics of triglyceride oil simultaneously.Conjugated linoleic acid glyceride absorption more readily digested than conjugated linolic acid in addition, tg cla after consumption 16h appears at blood, occur maximum level, and free fatty acids wants 24 hours just can reach maximum value in liver and organ.
Existing technological method has: 1, glycerine solution, and namely glycerine and triglyceride level mix by a certain percentage, adopts lipase-catalyzedly to prepare mono-glycerides and triglyceride.But while this method manufacture order acyl glyceride and DG ester, have by product free fatty acids and generate, productive rate is lower.2, lipase-catalyzed lipid acid and dehydrating glycerin Reactive Synthesis glyceride product; the application of this method is comparatively extensive; namely be this kind of method in the preparation method of the conjugated linoleic acid glyceride of Ministry of Health's announcement, though it is not there are some advantages, such as strict to substrate requirements; reaction conditions is gentle; there is specificity etc., but its defect is obvious, as lipase is expensive; and reaction time is oversize, all affect its large-scale production all the time.3, United States Patent (USP) PROCESSES FOR THEPRODUCTION OF TRIGLYCERIDES OF CONJUGATED LINOLEIC ACID (patent No.: US007067684B2) discloses a kind of method of synthesis of conjugated linoleic acid glyceryl ester, carry out transesterification reaction with conjugated linolic acid low-carbon-ester (alcohol contains 1-5 carbon atom) and glycerine triacetate, generate conjugated linoleic acid glyceride.Employing transesterification reaction production glyceryl ester can introduce the composition in former glyceryl ester, and such as this patent introduces acetic acid molecule, has the residual of acetic acid molecule, reduce quality product in product.4, United States Patent (USP) (patent No. 6124486) is mentioned and is used fatty acid soaps as catalyzer at 200-260 DEG C, and with lipid acid and glycerine triacetate Reactive Synthesis glyceryl ester, this method is higher due to temperature, can make unsaturated fatty acids acid cleavage, affect productive rate.
Summary of the invention
The object of the invention is to the shortcoming overcoming above-mentioned art methods, provide a kind of under solvent-free system, to improving production capacity, improving the preparation method that quality has the glycerin fatty acid ester of obvious effect.Be made up of following steps:
(1) receive with lower alcohol or rudimentary potassium alcoholate is catalyzer, lipid acid low-carbon-ester and glycerine in molar ratio 1:2-6:1 mix, and under 100-170 DEG C of condition, vacuum reaction 1-60h obtains glycerin fatty acid ester crude product;
(2) use the 30%-60% of glycerin fatty acid ester crude product weight, aqueous citric acid solution washing glycerin fatty acid ester crude product that massfraction is 1.5%-10% once, add the 80-100 DEG C of hot water of glycerin fatty acid ester crude product weight 10%-50% again, stir, stratification, is separated upper strata oil, then uses the hot water of 80-100 DEG C, wash 3 times, heating removed under reduced pressure moisture;
(3) at temperature 160-220 DEG C, under the condition of vacuum tightness 0.1-150pa, the product of step (2) described in molecular distillation, obtains glycerin fatty acid ester product.
Further, described lower alcohol is received as C1-C4 alcohol is received; Described rudimentary potassium alcoholate C1-C4 potassium alcoholate.
Further, described lower alcohol is received as sodium methylate, sodium ethylate; Described rudimentary potassium alcoholate is potassium methylate, potassium ethylate.
Further, described catalyst levels is the 0.2%-8% of lipid acid low-carbon-ester weight.
Further, lipid acid described in described lipid acid low-carbon-ester includes but not limited to sad, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, elaidic acid, linolic acid, conjugated linolic acid, linolenic acid, one or more mixture of AA, EPA, DHA.
Further, in described lipid acid low-carbon-ester, the number of the carbon of alcohol is 1-5.
Further, described lipid acid low-carbon-ester is one or both in fatty acid methyl ester, fatty-acid ethyl ester.
Further, the reaction vacuum tightness of described vacuum reaction is 0-10000pa.
Further, the reaction vacuum tightness of described vacuum reaction is 0-1000pa.
Preparation method's tool of glycerin fatty acid ester of the present invention has the following advantages: 1, this reaction is under solvent-free system, has obvious effect to raising production capacity, raising quality.2, compared with other method, by catalyze fatty acetoacetic ester, direct and glycerine reaction, does not have the introducing of acetic acid molecule impurity, compares Production by Enzymes production capacity high; Compare glycerol rhizolomy, during its subsequent disposal, as the raw material of next batch reaction, can there is not fatty acid by-products in unreacted lipid acid low-carbon-ester and glycerine.
Embodiment
Embodiment 1
A kind of preparation method of glycerin fatty acid ester, be made up of following steps: in reaction flask, add methyl stearate 1000g, glycerine is added by the mol ratio 8:10 of methyl stearate and glycerine, be heated to 120 DEG C, 1h is vacuumized under the condition of vacuum tightness 8000pa, add material gross weight 6% sodium ethylate solid catalyst, vacuumize reaction immediately, after being 100pa to vacuum tightness, continue reaction 0.5 hour stopped reaction, when being cooled to 95 DEG C, adding massfraction is that 2.5% aqueous citric acid solution washs once, the mol ratio 1:1 that addition presses sodium ethylate and citric acid adds.
After stratification, isolate upper strata oil, and with the water washing 3 times of 85 DEG C, heating removed under reduced pressure moisture.
At 190 DEG C, under vacuum tightness 15pa condition, molecular distillation removes the stearic acid of unreacted methyl stearate and generation, and detect its index according to the method in GB15612-1995, result is as following table:
| Interventions Requested | Assay |
| Sense organ | Oyster white waxy solid, odorless, tasteless |
| Glyceryl monostearate content, % | 94.5 |
| Iodine number | 2.4 |
| Zero pour, DEG C | 66.4 |
| Free acid (in stearic acid), % | 0.8 |
Embodiment 2
A kind of preparation method of glycerin fatty acid ester, be made up of following steps: in reaction flask, add methyl linoleate 1000g, glycerine is added by the mol ratio 2:0.8 of methyl linoleate and glycerine, be heated to 120 DEG C, under the condition of vacuum tightness 7000pa, vacuumize 30min, add the sodium methylate of 2% of methyl linoleate weight, vacuumize reaction immediately, after reducing to 700pa to vacuum tightness, continue reaction 1 hour, stopped reaction is also cooled to 96 DEG C.Add 2kg95 DEG C of hot water, stir, stratification, be separated upper strata oil, with 95 DEG C of hot water, wash 3 times, heating removed under reduced pressure moisture.
At 190 DEG C, under vacuum tightness 15pa condition, molecular distillation removes unreacted methyl linoleate, and obtain linoleic acid diester oil, detected result is as following table.
| Interventions Requested | Assay |
| Outward appearance | Pale yellow transparent oily liquids |
| Diglyceride content, % | 51.8 |
| Content of triglyceride, % | 46.8 |
| Content of monoglyceride, % | 1.3 |
| Free fatty acid content, % | 0.1 |
Embodiment 3
A kind of preparation method of glycerin fatty acid ester, be made up of following steps: in reactor, add ethyl linoleate 80kg, add glycerine by the mol ratio 2:1 of ethyl linoleate and glycerine, be heated to 140 DEG C, under the condition of vacuum tightness 8500pa, vacuumize 30min, add the sodium ethylate of 1% of ethyl linoleate weight, vacuumize reaction immediately, vacuum tightness slowly can decline, after being down to 650pa to vacuum tightness from a normal atmosphere, continue reaction 1 hour, stopped reaction is also cooled to 94 DEG C.Add 160kg95 DEG C of hot water, stir, stratification, be separated upper strata oil, wash 3 times with 95 DEG C of hot water, heating removed under reduced pressure moisture.
At 190 DEG C, under vacuum tightness 15pa condition, molecular distillation removes unreacted ethyl linoleate, and obtain linoleic acid diester, detected result is as following table.
| Interventions Requested | Assay |
| Outward appearance | Pale yellow transparent oily liquids |
| Diglyceride content, % | 47.2 |
| Content of triglyceride, % | 51.5 |
| Content of monoglyceride, % | 1.1 |
| Free fatty acid content, % | 0.2 |
Embodiment 4
A kind of preparation method of glycerin fatty acid ester, be made up of following steps: in reactor, add CLA methyl esters 120g, glycerine is added by the mol ratio 3.7:1 of CLA methyl esters and glycerine, be heated to 140 DEG C, 1 hour is vacuumized under the condition of vacuum tightness 500pa, add the sodium methylate of 1.5% of CLA methyl esters weight, vacuumize reaction immediately, vacuum tightness slowly can decline from a normal atmosphere, after being down to 130pa to vacuum tightness, continue reaction 3 hours, stopped reaction is also cooled to 96 DEG C.Add 240g 95 DEG C of hot water, stir, stratification, be separated upper strata oil, wash 3 times with 95 DEG C of hot water, heating removed under reduced pressure moisture.Detected result is as following table:
| Interventions Requested | Assay |
| Outward appearance | Colourless transparent oil liquid |
| Content of triglyceride, % | 38.1 |
| Diglyceride content, % | 6.4 |
| Content of monoglyceride, % | 1.2 |
| CLA methyl esters content, % | 55.6 |
Embodiment 5
A kind of preparation method of glycerin fatty acid ester, be made up of following steps: in reactor, add conjugated linoleic acid ethyl ester 200kg, glycerine is added by the mol ratio 4:1 of CLA methyl esters and glycerine, be heated to 140 DEG C, 1 hour is vacuumized under the condition of vacuum tightness 600pa, add the sodium methylate of 0.5% of CLA methyl esters weight, vacuumize reaction immediately, vacuum tightness slowly can decline from a normal atmosphere, after being down to 60pa to vacuum tightness, continue reaction 4 hours, stopped reaction is also cooled to 93 DEG C.Add the aqueous citric acid solution 100kg of 2.5%, mix stratification, be separated upper strata oil, wash 3 times with 95 DEG C of hot water, heating removed under reduced pressure moisture.
At 190 DEG C, under vacuum tightness 15pa condition, molecular distillation removes unreacted conjugated linoleic acid ethyl ester, obtains conjugated linoleic acid glyceride, and detected result is as following table:
| Interventions Requested | Assay |
| Outward appearance | Pale yellow transparent oily liquids |
| Content of triglyceride, % | 81.8 |
| Diglyceride content, % | 17.6 |
| Content of monoglyceride, % | 0.6 |
Embodiment 6
A kind of preparation method of glycerin fatty acid ester, be made up of following steps: in reactor, add fish oil ethyl ester 10kg, glycerine is added by the weight ratio 100:12 of fish oil ethyl ester and glycerine, be heated to 100 DEG C, 1 hour is vacuumized under the condition of vacuum tightness 8000pa, add the sodium methylate of 1% of fish oil ethyl ester weight, vacuumize reaction immediately, vacuum tightness slowly can decline from a normal atmosphere, after being down to 10pa to vacuum tightness, continue reaction 4 hours, stopped reaction and add 2.5% aqueous citric acid solution 3kg, mix rear stratification, separation upper strata oil, 3 times are washed with 95 DEG C of hot water, heating removed under reduced pressure moisture.
At 190 DEG C, under vacuum tightness 15pa condition, molecular distillation removes unreacted fish oil ethyl ester and lipid acid, obtains product, and detected result is as following table:
| Interventions Requested | Assay |
| Outward appearance | Pale yellow transparent oily liquids |
| Content of triglyceride, % | 71.2 |
| Diglyceride content, % | 27.2 |
| Content of monoglyceride, % | 1.6 |
Below the present invention be described in detail, the above, be only the preferred embodiment of the present invention, when not limiting the scope of the present invention, namely allly does impartial change according to the application's scope and modify, all should still belong in covering scope of the present invention.
Claims (9)
1. the preparation method of glycerin fatty acid ester, is characterized in that being made up of following steps:
(1) receive with lower alcohol or rudimentary potassium alcoholate is catalyzer, lipid acid low-carbon-ester and glycerine in molar ratio 1:2-6:1 mix, and under 100-170 DEG C of condition, vacuum reaction 1-60h obtains glycerin fatty acid ester crude product;
(2) use the 30%-60% of glycerin fatty acid ester crude product weight, aqueous citric acid solution washing glycerin fatty acid ester crude product that massfraction is 1.5%-10% once, add the 80-100 DEG C of hot water of glycerin fatty acid ester crude product weight 10%-50% again, stir, stratification, separation upper strata oil, use the hot water of 80-100 DEG C again, wash 3 times, heating removed under reduced pressure moisture;
(3) at temperature 160-220 DEG C, under the condition of vacuum tightness 0.1-150pa, the product of step (2) described in molecular distillation, obtains glycerin fatty acid ester product.
2. the preparation method of glycerin fatty acid ester as claimed in claim 1, is characterized in that: described lower alcohol is received as C1-C4 alcohol is received; Described rudimentary potassium alcoholate C1-C4 potassium alcoholate.
3. the preparation method of glycerin fatty acid ester as claimed in claim 1 or 2, is characterized in that: described lower alcohol is received as sodium methylate, sodium ethylate; Described rudimentary potassium alcoholate is potassium methylate, potassium ethylate.
4. the preparation method of glycerin fatty acid ester as claimed in claim 1, is characterized in that: described catalyst levels is the 0.2%-8% of lipid acid low-carbon-ester weight.
5. the preparation method of glycerin fatty acid ester as claimed in claim 1, is characterized in that: that lipid acid described in described lipid acid low-carbon-ester comprises is sad, capric acid, lauric acid, palmitinic acid, stearic acid, oleic acid, elaidic acid, linolic acid, conjugated linolic acid, linolenic acid, one or more mixture of AA, EPA, DHA.
6. the preparation method of glycerin fatty acid ester as claimed in claim 1, is characterized in that: in described lipid acid low-carbon-ester, the number of the carbon of alcohol is 1-5.
7. the preparation method of the glycerin fatty acid ester as described in claim 1 or 5, is characterized in that: described lipid acid low-carbon-ester is one or both in fatty acid methyl ester, fatty-acid ethyl ester.
8. the preparation method of glycerin fatty acid ester as claimed in claim 1, is characterized in that: the reaction vacuum tightness of described vacuum reaction is 0-10000pa.
9. the preparation method of the glycerin fatty acid ester as described in claim 1 or 8, is characterized in that: the reaction vacuum tightness of described vacuum reaction is 0-1000pa.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106748780A (en) * | 2016-12-09 | 2017-05-31 | 广州白云山汉方现代药业有限公司 | A kind of removal methods of injection Synthetic Oil metal residual |
| CN107459456A (en) * | 2016-06-02 | 2017-12-12 | 中国石化扬子石油化工有限公司 | A kind of method that methyl stearate is extracted in the benzoyl methane raffinate from stearic acid |
| WO2018028462A1 (en) * | 2016-08-09 | 2018-02-15 | 浙江医药股份有限公司新昌制药厂 | Fatty glyceride preparation method |
| CN107935851A (en) * | 2017-12-04 | 2018-04-20 | 广州星业科技股份有限公司 | A kind of Capmul MCM C8 and preparation method thereof |
| CN109053438A (en) * | 2018-06-28 | 2018-12-21 | 菏泽中禾健元生物科技有限公司 | A method of improving conjugated linoleic acid glyceride production efficiency |
| CN113264831A (en) * | 2021-06-04 | 2021-08-17 | 浙江皇马科技股份有限公司 | Preparation method of fatty acid monoglyceride |
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| CN103772196A (en) * | 2013-12-31 | 2014-05-07 | 广州星业科技股份有限公司 | Fatty glyceride as well as preparation method and application thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107459456A (en) * | 2016-06-02 | 2017-12-12 | 中国石化扬子石油化工有限公司 | A kind of method that methyl stearate is extracted in the benzoyl methane raffinate from stearic acid |
| WO2018028462A1 (en) * | 2016-08-09 | 2018-02-15 | 浙江医药股份有限公司新昌制药厂 | Fatty glyceride preparation method |
| CN107698447A (en) * | 2016-08-09 | 2018-02-16 | 浙江医药股份有限公司新昌制药厂 | The method for preparing fatty glyceride |
| US20190256448A1 (en) * | 2016-08-09 | 2019-08-22 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Fatty glyceride preparation method |
| US10844319B2 (en) * | 2016-08-09 | 2020-11-24 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Fatty glyceride preparation method |
| CN107698447B (en) * | 2016-08-09 | 2021-10-29 | 浙江医药股份有限公司新昌制药厂 | Method for preparing fatty glyceride |
| CN106748780A (en) * | 2016-12-09 | 2017-05-31 | 广州白云山汉方现代药业有限公司 | A kind of removal methods of injection Synthetic Oil metal residual |
| CN106748780B (en) * | 2016-12-09 | 2019-09-13 | 广州白云山汉方现代药业有限公司 | A kind of removal methods of injection Synthetic Oil metal residual |
| CN107935851A (en) * | 2017-12-04 | 2018-04-20 | 广州星业科技股份有限公司 | A kind of Capmul MCM C8 and preparation method thereof |
| CN107935851B (en) * | 2017-12-04 | 2021-02-19 | 广州星业科技股份有限公司 | Glyceryl monocaprylate and preparation method thereof |
| CN109053438A (en) * | 2018-06-28 | 2018-12-21 | 菏泽中禾健元生物科技有限公司 | A method of improving conjugated linoleic acid glyceride production efficiency |
| CN113264831A (en) * | 2021-06-04 | 2021-08-17 | 浙江皇马科技股份有限公司 | Preparation method of fatty acid monoglyceride |
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Application publication date: 20150401 |