CN1297873A - Method of preparing high-purity octacosyl alcohol with sugar-cane wax - Google Patents
Method of preparing high-purity octacosyl alcohol with sugar-cane wax Download PDFInfo
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- CN1297873A CN1297873A CN 99117253 CN99117253A CN1297873A CN 1297873 A CN1297873 A CN 1297873A CN 99117253 CN99117253 CN 99117253 CN 99117253 A CN99117253 A CN 99117253A CN 1297873 A CN1297873 A CN 1297873A
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- sugar
- cane wax
- octacosanol
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- cerosin
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Abstract
The process of preparing high purity octacosyl alcohol with sugar cane wax includes the steps of: addition of polar solvent to sugar cane wax and hydrolysis and saponification with base solution at 60-100 deg.C for 3-10 hr; addition of metal salt precipitant and filtering off solvent insoluble fatty acid and resinate while the solution is still hot; filtering the fully cooled filtrate mother liquid to obtain mixed fatty alcohol; stoving the mixed fatty alcohol before vacuum fractionation at 1-100 Pa; collecting 180-250 deg.c fraction, gas phase chromatic test, merging oxtacosyl alcohol fraction, fractionation for 1-3 times to obtain octacosyl alcohol product with purity higher than 90 %. The process is simple, short in reaction period, high in product yield and purity.
Description
The present invention relates to a kind of method of producing the high purity octacosanol by sugar-cane wax.
Octacosanol is a kind of straight chain high fatty alcohol that contains 28 carbon atoms, and is main to be present in the epidermis of fruit such as wheatgerm oil, Rice pollard oil and sugarcane, apple and grape with lipid acid bonded form.Common and the C of natural octacosanol
22To C
36Fatty Alcohol(C12-C14 and C12-C18) exist simultaneously.As octacosanol in the rice bran wax at C
24Only account in～C36 the mixed fatty alcohol about 12%, these Fatty Alcohol(C12-C14 and C12-C18) have similar chemical property, are difficult to extract highly purified octacosanol by general method.In various animals and plants waxes, cerosin is to obtain one of optimal raw material of octacosanol.The content of octacosanol accounts for 30%～70% in the cerosin in mixed fatty alcohol.According to reports, in Cuba's cerosin, the content of octacosanol accounts for 50%～70% in mixed fatty alcohol.The octacosanol of homemade cerosin only accounts for 25%～40%.From cerosin, extract the method for octacosanol (being actually a kind of mixed fatty alcohol), existing many articles and patent report.
Horn etc. have proposed to produce the method for Fatty Alcohol(C12-C14 and C12-C18) from cerosin in Journal of Science Food and Agriculture 10,571 (1957).This method adopts alcoholic potash to carry out the homogeneous saponification, separate and remove saponified (mainly being lipid acid and resinous acid), with unsaponifiables (mainly being Fatty Alcohol(C12-C14 and C12-C18), hydrocarbon etc.) esterification, obtain the mixing-in fat alcohol ester with the molecular distillation method, obtain mixed fatty alcohol again with the potassium hydroxide saponification at last.This method shortcoming is that step is long, and the product that obtains remains alcohol mixture, and octacosanol content is not improved significantly.
R.K Gupta etc. have reported the method for extracting alcohol mixture from smart cerosin at Reserach Industry 30 on the 95-101 (1985).This method is the sugar-cane wax that melts in advance with dense sodium hydroxide solution homogeneous phase saponification, and what obtain is saponified with benzene azeotropic distillation and drying.Dried material is easy to become powder, and the benzole soln with ethylene dichloride extracts alcohol mixture then.
A.L. the method to Gupta in Chinese patent CN1074435A such as Ge Lanijia has been done improvement.This patent adopts the method for saponification identical with Gupta, and the cured article that obtains after the saponification directly extracts alcohol mixture with hexane, acetone, benzene or methylene dichloride equal solvent.From Cuba's cerosin, can isolate octacosanol content in this way and be 55%～80% alcohol mixture.
Though the separation method that above-mentioned A.L. Ge Lanijia is adopted is fit to extract mixed fatty alcohol from sugar-cane wax, and is not suitable for the extraction of high purity octacosanol.Someone once separated homemade cerosin with this method, and what obtain is that octacosanol content only is 35～45% mixed fatty alcohol.
The purpose of this invention is to provide and a kind ofly reach method more than 90% by producing octacosanol purity in the sugar-cane wax, this method is applicable to the cerosin of any quality, is not subjected to the restriction of the place of production, kind.
The method of producing the high purity octacosanol by sugar-cane wax that the present invention proposes comprises the following steps:
(1) in sugar-cane wax, adds polar solvent, use alkaline solution 60～100 ℃ of following hydrolysis saponification 3～10 hours;
(2) add metallic compound precipitator after the hydrolysis in saponification liquor, the lipid acid and the resinate that will be insoluble to solvent while hot remove by filter;
(3) after the mother liquor that filtration is obtained fully cools off, filter again and obtain mixed fatty alcohol;
(4) high-vacuum fractionation is carried out in the mixed fatty alcohol oven dry back that above-mentioned steps is obtained under 1～100 handkerchief;
(5) collect 180～250 ℃ of fractions, check each fraction with gas-chromatography, merge the octacosanol fraction, fractionation is 1～3 time again, until obtaining the octacosanol product of purity more than 90%.
Sugar-cane wax of the present invention is crude cane wax or the smart cerosin of fusing point between 65～82 ℃, the preferred smart cerosin of fusing point between 76～82 ℃.
Polar solvent of the present invention can be methyl alcohol, ethanol, acetone or butanone, and consumption is 3～20 times of cerosin weight, and wherein particular methanol or concentration are 95% ethanol, and consumption is 5～10 times of cerosin weight.
Alkaline solution of the present invention is sodium hydroxide or potassium hydroxide solution, and consumption is 10～30% of a cerosin weight.
Metallic compound precipitator of the present invention is divalence or polyvalent metal salt, calcium chloride preferably, consumption is 10～30% of a cerosin weight, its objective is the sodium salt of lipid acid and resinous acid or sylvite changed into and be insoluble to the alcoholic acid calcium salt, and Fatty Alcohol(C12-C14 and C12-C18) still dissolves in the ethanol or methyl alcohol of heat, by heat filtering they is separated.
Be preferably in after the mixed fatty alcohol oven dry of the present invention and carry out high-vacuum fractionation under 1～20 handkerchief.
The octacosanol product that adopts the present invention to produce has following specific composition:
1-tetracosa carbon alcohol 0.0-1.5%
1-26 carbon alcohol 0.5-30%
1-octacosanol 90.0-98.0%
1-29 carbon alcohol 0.0-0.5%
1-30 carbon alcohol 1.0-5.5%
1-32 carbon alcohol 0.5-2.0%
1-30 four carbon alcohols 0.0-0.5%
Compare with other currently known methodss, the present invention propose by the method for producing the high purity octacosanol in the sugar-cane wax, it is simple to have technology, the reaction times is short, the advantage that productive rate and purity are high.
Octacosanol is universally acknowledged antifatigue material.Foreign study shows, at C
24～C
36In the Fatty Alcohol(C12-C14 and C12-C18), has only C
28Alcohol has significant antifatigue effect.Present commercial octacosanol great majority are that content is the alcohol mixture of 12-30%.By comparing the animal anti-fatigue test that octacosanol content is respectively three kinds of products of 20% (deriving from rice bran wax), 41% (deriving from cerosin) and 94% (deriving from the present invention), find that the octacosanol that adopts the inventive method to obtain has very significant antifatigue effect, and the test-results of all the other two kinds of octacosanol products and unsatisfactory.This may be because by the pure product purity height of the C28 of the present invention's acquisition, it is unique to form, the easier result who is absorbed by the body and is brought.
Mouse swimming with a load attached to the body test: choose 84 of Kunming kind male white mouses about body weight 19g, be divided into 4 groups at random: the I group is control group (physiological saline), and II-IV group is respectively that purity is the C of 20% (deriving from rice bran wax), 41% (deriving from cerosin) and 94% (deriving from the present invention)
28The alcohol group (is dispersed in octacosanol in the distilled water with ultrasonic wave, obtain suspension liquid), each organizes the per os gastric infusion, once a day, successive administration 21 days, after the last administration 30 minutes, put mouse and in the swimming cylinder, swim 25 ± 0.5 ℃ of water temperatures, the mouse tail 5% body weight sheet lead of loading, the record mouse begins to the dead time from swimming, but as the mouse swimming time, the results are shown in Table 1.
Table 1 mouse swimming with a load attached to the body test (x ± s)
| Group | Number of mice (only) | Dosage (mg/kg) is (with C 28The alcohol meter) | Between swimming (min) | The P value |
| ????Ⅰ | ????12 | ????-- | ????14.25±7.28 | ????-- |
| ????Ⅱ | ????12 | ????0.5 | ????16.18±6.48 | ????-- |
| ????12 | ????5 | ????15.18±7.34 | ????-- | |
| ????Ⅲ | ????12 | ????0.5 | ????17.49±8.01 | ????-- |
| ????12 | ????5 | ????21.58±6.12 | ????＜0.05 | |
| ????Ⅳ | ????12 | ????0.5 | ????29.91±5.96 | ????＜0.01 |
| ????12 | ????5 | ????28.41±6.33 | ????＜0.01 |
The data declaration of table 1, the octacosanol of picked-up low-purity is little to the influence of mouse swimming time, has only the III group when dosage is 5mg/kg, and significant difference (P＜0.05) is just arranged.And by the pure product (IV group) of the C28 of the present invention's acquisition, above-mentioned two dosage all can prolong the mouse swimming time, compare with control group, and highly significant difference (P＜0.01) is arranged.
Octacosanol is tested the influence of Mouse Liver glycogen content: choose 84 of Kunming kind 2.5-3 month male mices, divide 4 groups at random, I is a control group, and II, III, IV group are that octacosanol content is respectively 20%, 41% and 94% octacosanol group, and administering mode and number of times are with aforesaid swimming test, after the administration 21 days, put to death immediately, get liver and after the physiological saline rinsing, blot, accurately take by weighing liver 200mg with filter paper, press anthrone method and survey hepatic glycogen content, the results are shown in Table 2.
Table 2 octacosanol is to the influence of Mouse Liver glycogen content (x ± s)
| Group | Number of mice (only) | Dosage (mg/kg) is (with C 28The alcohol meter) | Liver starch (mg/100g tissue) | The P value |
| ????Ⅰ | ????12 | ????-- | ????2.36±0.81 | ????-- |
| ????Ⅱ | ????12 | ????1.0 | ????2.26±0.92 | ????-- |
| ????12 | ????5.0 | ????2.91±0.81 | ????-- | |
| ????Ⅲ | ????12 | ????1.0 | ????2.76±0.65 | ????-- |
| ????12 | ????5.0 | ????3.91±1.31 | ????＜0.05 | |
| ????Ⅳ | ????12 | ????1.0 | ????4.81±0.92 | ????＜0.01 |
| ????12 | ????5.0 | ????4.72±1.01 | ????＜0.01 |
Table 2 test-results is consistent with table 1 result.Compare with control group, IV group hepatic glycogen content has highly significant difference (P＜0.01), and low-purity C
28In the alcohol group (II, III group), have only when dosage is increased to 5mg/kg (III group), liver starch just has significant difference.
Specify the present invention below by embodiment.
Embodiment 1
Adopting fusing point is 76-82 ℃ of homemade smart cerosin 5kg, adding 25kg concentration is 95% alcohol and 0.5kg sodium hydroxide, after the reflux 8 hours, add 10 liters of spirituous solutions that contain calcium chloride 600g in the above-mentioned saponification liquor, reflux 1 hour, filtered while hot, throw out divides secondary washing with the alcohol of 20 liters of heat, and filtrate is merged, and is cooled to the room temperature after-filtration, get Fatty Alcohol(C12-C14 and C12-C18) 1.1kg after the oven dry, its composition of gas chromatographic analysis is: C
244%, C
268%, C
2841%, C
293%, C
3024%, C
328%, C
343%.
With the vacuum fractionation 3 times under 10 handkerchiefs of above-mentioned 1.1kg alcohol mixture, collect 210-215 ℃ of fraction, product 260g, it consists of gas chromatographic analysis: C
261.2%, C
2894.1%, C
302.6%, C
321.1%.
Embodiment 2
Adopting fusing point is 76-80 ℃ of homemade smart cerosin 5kg, add 40kg methyl alcohol and 0.5kg potassium hydroxide, after heating in water bath refluxed 10 hours, adding contained 10 liters of the methanol solutions of calcium chloride 600g, reflux 1 hour in the above-mentioned saponification liquor, filtered while hot, throw out is 50 ℃ a methyl alcohol branch secondary washing with 20 intensification degree, with the filtrate platform also, is chilled to the room temperature after-filtration, get Fatty Alcohol(C12-C14 and C12-C18) 1.4kg after the oven dry, its composition of gas chromatographic analysis is: C
243%, C
269%, C
2839%, C
292%, C
3026%, C
326%, C
343%, C
362%.
With the vacuum fractionation 3 times under the 10-15 handkerchief of above-mentioned 1.4kg alcohol mixture, collect 213-218 ℃ of fraction, product 310g, it consists of gas chromatographic analysis: C
262.5%, C
2891.2%, C
304.9%, C
320.5%.
Embodiment 3
Adopting fusing point is 66-73 ℃ of homemade cerosin 10Kg, add 100Kg acetone and 1.4Kg potassium hydroxide, after the reflux 8 hours, in above-mentioned saponification liquor, add 1.7Kg calcium chloride, reflux 2 hours, filtered while hot, throw out is 45 ℃ an acetone branch secondary washing with 20 intensification degree, and filtrate is merged, and is chilled to the room temperature after-filtration, get Fatty Alcohol(C12-C14 and C12-C18) crude product 2.1Kg after the oven dry, its Fatty Alcohol(C12-C14 and C12-C18) of gas chromatographic analysis consists of: C
242%, C
267%, C
2828%, C
291%, C
3018%, C
326%, C
344%, C
361%.
With the vacuum fractionation 3 times under 10 handkerchiefs of above-mentioned 2.1Kg crude product, collect 210-215 ℃ of fraction, product 240g, it consists of gas chromatographic analysis: C
261.2%, C
2891.7%, C
302.1%, C
321.0%.
Claims (9)
1, produced the method for high purity octacosanol by sugar-cane wax, this method comprises the following steps:
(1) in sugar-cane wax, adds polar solvent, use alkaline solution 60～100 ℃ of following hydrolysis saponification 3～10 hours;
(2) add metallic compound precipitator after the hydrolysis in saponification liquor, the lipid acid and the resinate that will be insoluble to solvent while hot remove by filter;
(3) after the mother liquor that filtration is obtained fully cools off, filter again and obtain mixed fatty alcohol;
(4) high-vacuum fractionation is carried out in the mixed fatty alcohol oven dry back that above-mentioned steps is obtained under 1～100 handkerchief;
(5) collect 180～250 ℃ of fractions, check each fraction with gas-chromatography, merge the octacosanol fraction, fractionation is 1～3 time again, until obtaining the octacosanol product of purity more than 90%.
2, as claimed in claim 1ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described sugar-cane wax is crude cane wax or the smart cerosin of fusing point between 65～82 ℃.
3, as claimed in claim 2ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described sugar-cane wax is the smart cerosin of fusing point between 76～82 ℃.
4, as claimed in claim 1ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described polar solvent is methyl alcohol, ethanol, acetone or butanone, and consumption is 3～20 times of cerosin weight.
5, as claimed in claim 4ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described polar solvent is that methyl alcohol or concentration are 95% ethanol, and consumption is 5～10 times of cerosin weight.
6, as claimed in claim 1ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described alkaline solution is sodium hydroxide or potassium hydroxide solution, and consumption is 10～30% of a cerosin weight.
7, as claimed in claim 1ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described metallic compound precipitator is divalence or polyvalent metal salt, and consumption is 10～30% of a cerosin weight.
8, as claimed in claim 6ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: described metallic compound precipitator is a calcium chloride.
9, as claimed in claim 1ly produce the method for high purity octacosanol by sugar-cane wax, it is characterized in that: high-vacuum fractionation is carried out in mixed fatty alcohol oven dry back under 1～20 handkerchief.
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|---|---|---|---|
| CN99117253A CN1098242C (en) | 1999-11-30 | 1999-11-30 | Method of preparing high-purity octacosyl alcohol with sugar-cane wax |
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|---|---|---|---|
| CN99117253A CN1098242C (en) | 1999-11-30 | 1999-11-30 | Method of preparing high-purity octacosyl alcohol with sugar-cane wax |
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| CN1098242C CN1098242C (en) | 2003-01-08 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249847A (en) * | 2011-08-03 | 2011-11-23 | 中国林业科学研究院资源昆虫研究所 | Method for refining octacosanol |
| CN109651089A (en) * | 2018-12-26 | 2019-04-19 | 杭州余杭博士达油脂有限公司 | A method of using rice bran hair wax as waste n-octacosanol |
| CN110724031A (en) * | 2019-10-23 | 2020-01-24 | 广东省生物工程研究所（广州甘蔗糖业研究所） | Method for extracting octacosanol from sugarcane peel cane wax |
-
1999
- 1999-11-30 CN CN99117253A patent/CN1098242C/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102249847A (en) * | 2011-08-03 | 2011-11-23 | 中国林业科学研究院资源昆虫研究所 | Method for refining octacosanol |
| CN109651089A (en) * | 2018-12-26 | 2019-04-19 | 杭州余杭博士达油脂有限公司 | A method of using rice bran hair wax as waste n-octacosanol |
| CN110724031A (en) * | 2019-10-23 | 2020-01-24 | 广东省生物工程研究所（广州甘蔗糖业研究所） | Method for extracting octacosanol from sugarcane peel cane wax |
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| CN1098242C (en) | 2003-01-08 |
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Owner name: GUANGDONG GUANG YE QING YI FOOD TECHNOLOGY CO., L Free format text: FORMER OWNER: GUANGDONG PROV. INST. OF FOOD INDUSTRY Effective date: 20080118 |
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Effective date of registration: 20080118 Address after: Guangzhou, Guangdong Province, Panyu District City, South Village, new base village industrial zone, 303 Jin Xin Avenue Patentee after: Guangdong Guangye Swiss food science & Technology Co Ltd Address before: No. 6, Xingang East Road, Guangdong, Guangzhou Patentee before: Guangdong Prov. Food Industry Inst. |
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