CN101486951A - Method for separating oleate, linolic acid, oleate and linoleate - Google Patents
Method for separating oleate, linolic acid, oleate and linoleate Download PDFInfo
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- CN101486951A CN101486951A CNA2009100737731A CN200910073773A CN101486951A CN 101486951 A CN101486951 A CN 101486951A CN A2009100737731 A CNA2009100737731 A CN A2009100737731A CN 200910073773 A CN200910073773 A CN 200910073773A CN 101486951 A CN101486951 A CN 101486951A
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- oleic acid
- linoleate
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Abstract
The invention discloses a method separating oleic acid and linoleic acid, and oleate and linoleate, which uses silica gel, active carbon or alumina as a carrier, and dissolves the urea, the quality ratio of which and the carrier being 1: 0.1 to 10, by solvent and infuses the urea on the carrier; the loading-type urea obtained by removing the solvent serves as fixed phase and loaded into the chromatographic column; the mixture raw materials to be separated containing oleic acid and linoleic acid or oleate and linoleate are added into the upper column of the chromatographic column; elution is carried out by mobile phase, and the elution portions in different periods are collected; and through gas chromatography detection, the solvent is removed from the collected elution portions rich in oleic acid and linoleic acid or oleate and linoleate to obtain high-purity oleic acid and linoleic acid products or oleate and linoleate products. The method has the advantages of simple technology, low production cost, good separation effect, high collection rate, green environmental protection.
Description
Technical field
The invention belongs to field of grease chemical technology, relate in particular to the method for a kind of oleic acid and linoleic acid oil acid esters and linoleate.
Technical background
Oleic acid (oleic acid) also claim 18 monoenoic acids, is a kind of unsaturated fatty acids that contains two keys in the natural animal-plant grease, and molecular formula is C
17H
33COOH.Oleic acid is important grease fine chemical product, except that being widely used in chemical industry, mechanical industry, application at aspects such as medicine, daily use chemicals also has been subjected to attention, especially process is handled the high-purity oleic acid that obtains, and good stability is non-stimulated to skin, safe, having good physics, chemical property, is a kind of important chemical reagent, can be widely used in fields such as organic synthesis, biotechnology and medication preparation.
Linolic acid (linoleic acid) also claim octadecadienoic acid, is a kind of unsaturated fatty acids that contains two two keys in the natural animal-plant grease, and molecular formula is C
17H
31COOH.Linolic acid is an essential fatty acid, studies show that, it is complete that linolic acid can be kept the cells in vivo film, control cell metabolism, reducing cholesterol level, prevention and treatment cardiovascular and cerebrovascular diseases etc.Conjugated linolic acid is linoleic isomer, a large amount of conjugated linolic acids that studies show that can suppress skin carcinoma, cancer of the stomach, mammary cancer and colorectal carcinoma, have anti-mutation, improve immunologic function, prevent arteriosclerosis, physiological functions such as fat-reducing, anti-diabetic and promotion growth.
Because the difference of just two key numbers in oleic acid, Witconol 2301, ethyl oleate, linolic acid, methyl linoleate, the ethyl linoleate molecular structure, structural similitude, character is close, for example boiling point differs in 1 ℃, condensation point and polarity are all extremely approaching, also effectively do not separate the purification way at present.
Summary of the invention
The purpose of this invention is to provide a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate.
Concrete operations step of the present invention is as follows:
(1) selecting silica gel, gac or aluminum oxide for use is carrier, will be that the urea of 1:0.1～10 is impregnated on the carrier by dissolution with solvents with the carrier mass ratio, removes loading type urea that solvent obtains as stationary phase, the chromatography column of packing into;
(2) column chromatography: the mixture material that will isolatingly contain oleic acid and linoleic mixture or oleic acid ester and linoleate adds the chromatography column upper prop, carries out wash-out with moving phase, collects the elution fraction of different periods;
(3) desolventizing: by gas chromatographic detection, be rich in oleic acid and linoleic elution fraction or be rich in oleic acid ester and the elution fraction of linoleate, remove solvent, obtain high-purity oleic acid, linolic acid product or oleic acid ester and linoleate product with what collect.
As described in (1) step, solvent for use is the mixing solutions of water-alcoholic solution, alcohol or various alcohol, and described alcohol refers to carbonatoms less than 4 monohydroxy-alcohol, particular methanol, ethanol or Virahol.
As described in (2) step, used moving phase is any dissolves fat acid or the fatty acid ester not solvent or the solution of dissolved urea, or the urea saturated solution of any dissolves fat acid or fatty acid ester.
The solvent of described not dissolved urea be sherwood oil, normal hexane, chloroform, ethyl acetate, methyl acetate one or more,
The solution of described not dissolved urea be urea saturated solution, the ethyl acetate alcoholic solution of urea saturated solution, the alcoholized chloroform solution of urea saturated solution, the normal hexane alcoholic solution of sherwood oil alcoholic solution urea saturated solution, methyl acetate alcoholic solution urea saturated solution one or more.
The urea saturated solution of described dissolves fat acid or fatty acid ester be urea saturated solution, the ethyl acetate alcoholic solution of urea saturated solution, the alcoholized chloroform solution of urea saturated solution, the normal hexane alcoholic solution of methyl alcohol urea saturated solution, ethanol urea saturated solution or sherwood oil alcoholic solution urea saturated solution, methyl acetate alcoholic solution urea saturated solution one or more.
Alcohol in the described alcoholic solution is methyl alcohol or ethanol.
As the described oleic acid ester of (2) step is oleic methyl esters, ethyl ester, propyl ester or butyl ester, and linoleate is linoleic methyl esters, ethyl ester, propyl ester or butyl ester.
As described in (2) step, usedly contain oleic acid, linoleic mixture material is the hydrolysate that contains oleic acid and linolic acid grease
As the mixture material that contains oleic acid ester and linoleate as described in (2) step is any alcoholysis product that contains oleic acid and linolic acid grease methyl alcohol, ethanol, propyl alcohol or butanols.
Containing oleic acid and linolic acid grease as mentioned above is soybean oil, peanut oil, sesame oil, rapeseed oil, Trisun Oil R 80, Semen Maydis oil, barbadosnut seed oil, Fructus Maydis oil, Prunus amygdalus oil, safflower oil and sewer oil or its mixture.But be not limited to above-mentioned grease.
Characteristics of the present invention
The present invention has following characteristics:
1. technology is simple, and production cost is low;
2. good separating effect, the yield height; Difference according to raw material can obtain
3. can while high purity oleic acid or its methyl/ethyl ester, high purity linolic acid or its methyl/ethyl ester product.
Utilize loading type urea to be stationary phase,, can well separate oleic acid, linolic acid or its methyl/ethyl ester by the moving phase wash-out.This method has that technology is simple, purity is high, yield is high, cost is low, pollute less, be easy to characteristics such as industrialization.
Embodiment
Embodiment 1:
Take by weighing 20g urea, be dissolved in the solution of moisture 20wt% methyl alcohol, add the 40g alumina supporter, decompression rotation evaporate to dryness is produced the stationary phase that load has urea; Prepare the ethanolic soln that contains sherwood oil 8wt%, as moving phase; With the soybean oil methyl alcohol alcoholysate of pipette, extract 2ml, last sample, column chromatography, by gas chromatographic detection, collect the elution fraction that is rich in Witconol 2301 and methyl linoleate respectively, obtain the Witconol 2301 of content 88wt% and the methyl linoleate of content 86wt%.
Embodiment 2:
Take by weighing 40g urea, be dissolved in the ethanolic soln that contains methyl alcohol 60wt%, be made into saturated solution, add the 20g silica-gel carrier, freezing stirred crystallization is filtered, and produces the stationary phase that load has urea; With sherwood oil as moving phase; With sample on the pipette, extract 3ml rapeseed oil hydrolyzate, column chromatography, by gas chromatographic detection, collect respectively and be rich in oleic acid and linoleic elution fraction, obtain the oleic acid of content 91wt% and the linolic acid of content 90wt%.
Embodiment 3:
Take by weighing 50g urea, be dissolved in the anhydrous methanol, be made into saturated solution, add the 10g silica-gel carrier, slowly add dehydrated alcohol, allow urea slowly separate out, load on the silica gel, filter, produce the stationary phase that load has urea; With normal hexane as moving phase; With the ethanol alcoholysate of pipette, extract 2ml Trisun Oil R 80, last sample, column chromatography, by gas chromatographic detection, collect the elution fraction that is rich in ethyl oleate and ethyl linoleate respectively, obtain the ethyl oleate of content 85wt% and the ethyl linoleate of content 87wt%.
Embodiment 4:
Take by weighing 55g urea, be dissolved in the 85wt% Virahol, be made into saturated solution, add the 10g absorbent charcoal carrier, decompression rotation evaporate to dryness allows urea load on the gac, filters, and produces the stationary phase that load has urea; Be made into the ethanolic soln that contains 1wt% methyl alcohol, as moving phase; With the hydrolysate of pipette, extract 2ml oleum lini, last sample, column chromatography, by gas chromatographic detection, collect respectively and be rich in oleic acid and linoleic elution fraction, obtain the oleic acid of content 95wt% and the linolic acid of content 93wt%.
Embodiment 5:
Take by weighing 60g urea, be dissolved in the anhydrous methanol, be made into saturated solution, add the 15g alumina supporter, decompression rotation evaporate to dryness is produced the stationary phase that load has urea; With normal hexane as moving phase; With the hydrolyzate of pipette, extract 3ml sesame oil, last sample, column chromatography, by gas chromatographic detection, collect respectively and be rich in oleic acid and linoleic elution fraction, obtain the oleic acid of content 85wt% and the linolic acid of content 80wt%.
Embodiment 6:
Take by weighing 50g urea, in the solution 95wt% methyl alcohol, be made into saturated solution, add the 20g absorbent charcoal carrier, decompression rotation evaporate to dryness is produced the stationary phase that load has urea; Be made into the urea methanol saturated solution, as moving phase; With the propyl alcohol alcoholysate of pipette, extract 3ml sewer oil, last sample, column chromatography, by gas chromatographic detection, collect the elution fraction that is rich in oleic acid propyl ester and linolic acid propyl ester respectively, obtain the oleic acid propyl ester of content 76wt% and the linolic acid propyl ester of content 78wt%.
Embodiment 7:
Take by weighing 40g urea, be dissolved in and contain in the 20wt% alcoholic acid methyl alcohol, be made into saturated solution, add the 30g silica-gel carrier, freezing stirred crystallization is filtered, and produces the stationary phase that load has urea; Be made into 95wt% alcoholic acid urea saturated solution, as moving phase; With the alcoholic acid alcoholysis product of pipette, extract 4ml Semen Maydis oil, last sample, column chromatography, by gas chromatographic detection, collect the elution fraction that is rich in ethyl oleate and ethyl linoleate respectively, obtain the ethyl oleate of content 91wt% and the ethyl linoleate of content 95wt%.
Embodiment 8:
Take by weighing 50g urea, be dissolved in the anhydrous methanol, be made into saturated solution, add 50g silica gel, decompression rotation evaporate to dryness makes the stationary phase that load has urea; Be made into and contain methyl alcohol 5wt% chloroformic solution, as moving phase; With the hydrolyzate of pipette, extract 3ml barbadosnut seed oil, last sample, column chromatography, by gas chromatographic detection, collect respectively and be rich in oleic acid and linoleic elution fraction, obtain the oleic acid of content 90wt% and the linolic acid of content 90wt%.
Embodiment 9:
Take by weighing 50g urea, be dissolved in the methanol solution that contains the 10wt% Virahol, add the 50g aluminum oxide, decompression rotation evaporate to dryness makes the stationary phase that load has urea; Be made into the ethanolic soln that contains ethyl acetate 50wt%, as moving phase; With the hydrolyzate of pipette, extract 2ml Semen Maydis oil, last sample, column chromatography, by gas chromatographic detection, collect respectively and be rich in oleic acid and linoleic elution fraction, obtain the oleic acid of content 87wt% and the linolic acid of content 89wt%.
Embodiment 10:
Take by weighing 40g urea, be dissolved in the anhydrous methanol, add 30g silica gel, decompression rotation evaporate to dryness makes the stationary phase that load has urea; Be made into the petroleum ether solution that contains ethyl acetate 50wt%, as moving phase; With the alcoholysis product of the butanols of pipette, extract 3ml peanut oil, last sample, column chromatography, by gas chromatographic detection, collect the elution fraction that is rich in butyl oleate and linolic acid butyl ester respectively, obtain the butyl oleate of content 97wt% and the linolic acid butyl ester of content 89wt%.
Claims (13)
1, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate is characterized in that comprising the steps:
(1) being carrier with silica gel, gac or aluminum oxide, will be that the urea of 1:0.1～10 is impregnated on the carrier by dissolution with solvents with the carrier mass ratio, remove loading type urea that solvent obtains as stationary phase, the chromatography column of packing into;
(2) column chromatography: the mixture material that will isolatingly contain oleic acid and linoleic mixture or oleic acid ester and linoleate adds the chromatography column upper prop, carries out wash-out with moving phase, collects the elution fraction of different periods;
(3) desolventizing: by gas chromatographic detection, be rich in oleic acid and linoleic elution fraction or be rich in oleic acid ester and the elution fraction of linoleate, remove solvent, obtain high-purity oleic acid, linolic acid product or oleic acid ester and linoleate product with what collect.
2, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 1 is characterized in that step (1) solvent for use is the mixing solutions of water one alcoholic solution, alcohol or various alcohol.
3, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 2 is characterized in that described alcohol is carbonatoms less than 4 monohydroxy-alcohol.
4, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 3 is characterized in that described carbonatoms is methyl alcohol, ethanol or Virahol less than 4 monohydroxy-alcohol.
5, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 1, it is characterized in that the used moving phase of step (2) is any dissolves fat acid or the fatty acid ester not solvent or the solution of dissolved urea, or the urea saturated solution of any dissolves fat acid or fatty acid ester.
6, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 5, the solvent that it is characterized in that described not dissolved urea be sherwood oil, normal hexane, chloroform, ethyl acetate, methyl acetate one or more,
7, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 5, the solution that it is characterized in that the not dissolved urea stated be urea saturated solution, the ethyl acetate alcoholic solution of urea saturated solution, the alcoholized chloroform solution of urea saturated solution, the normal hexane alcoholic solution of sherwood oil alcoholic solution urea saturated solution, methyl acetate alcoholic solution urea saturated solution one or more.
8, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 5, the urea saturated solution that it is characterized in that described dissolves fat acid or fatty acid ester be urea saturated solution, the ethyl acetate alcoholic solution of urea saturated solution, the alcoholized chloroform solution of urea saturated solution, the normal hexane alcoholic solution of methyl alcohol urea saturated solution, ethanol urea saturated solution or sherwood oil alcoholic solution urea saturated solution, methyl acetate alcoholic solution urea saturated solution one or more.
9, as claim 7 or 8 described a kind of methods of separating oleic acid and linolic acid, oleic acid ester and linoleate, it is characterized in that the alcohol in the described alcoholic solution is methyl alcohol or ethanol.
10, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 1, it is characterized in that the described oleic acid ester of step (2) is oleic methyl esters, ethyl ester, propyl ester or butyl ester, linoleate is linoleic methyl esters, ethyl ester, propyl ester or butyl ester.
11, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 1 is characterized in that step (2) describedly contains oleic acid, linoleic mixture is the hydrolysate that contains oleic acid and linolic acid grease
12, a kind of method of separating oleic acid and linolic acid, oleic acid ester and linoleate as claimed in claim 1 is characterized in that the described mixture that contains oleic acid ester and linoleate of step (2) is the alcoholysis product that contains oleic acid and linolic acid grease methyl alcohol, ethanol, propyl alcohol or butanols.
13,, it is characterized in that describedly containing oleic acid and the linolic acid grease is soybean oil, peanut oil, sesame oil, rapeseed oil, Trisun Oil R 80, Semen Maydis oil, barbadosnut seed oil, Fructus Maydis oil, Prunus amygdalus oil, safflower oil and sewer oil or its mixture as claim 11 or 12 described a kind of methods of separating oleic acid and linolic acid, oleic acid ester and linoleate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009100737731A CN101486951A (en) | 2009-02-11 | 2009-02-11 | Method for separating oleate, linolic acid, oleate and linoleate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009100737731A CN101486951A (en) | 2009-02-11 | 2009-02-11 | Method for separating oleate, linolic acid, oleate and linoleate |
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|---|---|
| CN101486951A true CN101486951A (en) | 2009-07-22 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058866A (en) * | 2011-10-20 | 2013-04-24 | 中国科学院兰州化学物理研究所 | Preparation method of high-purity linoleic acid triglyceride in gardenia |
| WO2016041506A1 (en) * | 2014-09-19 | 2016-03-24 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high-content conjugated linoleic acid through purification of vegetable oil as raw material |
| CN108179054A (en) * | 2018-01-12 | 2018-06-19 | 广东瑞邦日化有限公司 | The extracting method of pecan tree seed oil and its application in hair dye |
| CN111117772A (en) * | 2019-11-15 | 2020-05-08 | 青海大学 | Method for extracting medlar oil from medlar leftovers or residues |
-
2009
- 2009-02-11 CN CNA2009100737731A patent/CN101486951A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058866A (en) * | 2011-10-20 | 2013-04-24 | 中国科学院兰州化学物理研究所 | Preparation method of high-purity linoleic acid triglyceride in gardenia |
| WO2016041506A1 (en) * | 2014-09-19 | 2016-03-24 | 浙江医药股份有限公司新昌制药厂 | Method for preparing high-content conjugated linoleic acid through purification of vegetable oil as raw material |
| US10011550B2 (en) * | 2014-09-19 | 2018-07-03 | Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory | Method for preparing high-content conjugated linoleic acid with vegetable oil |
| CN108179054A (en) * | 2018-01-12 | 2018-06-19 | 广东瑞邦日化有限公司 | The extracting method of pecan tree seed oil and its application in hair dye |
| CN108179054B (en) * | 2018-01-12 | 2023-12-05 | 广东瑞邦日化有限公司 | Extraction method of American hickory seed oil and application of American hickory seed oil in hair dye |
| CN111117772A (en) * | 2019-11-15 | 2020-05-08 | 青海大学 | Method for extracting medlar oil from medlar leftovers or residues |
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Open date: 20090722 |