CN1030763C - Method for obtaining a mixture of higher aliphatic alcohols from sugar cane wax - Google Patents
Method for obtaining a mixture of higher aliphatic alcohols from sugar cane wax Download PDFInfo
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- CN1030763C CN1030763C CN 92100246 CN92100246A CN1030763C CN 1030763 C CN1030763 C CN 1030763C CN 92100246 CN92100246 CN 92100246 CN 92100246 A CN92100246 A CN 92100246A CN 1030763 C CN1030763 C CN 1030763C
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Abstract
The present invention relates to an aliphatic alcohol containing 24 to 34 carbon atoms, particularly to straight chain aliphatic alcohols containing 24, 26, 27, 28, 29, 30, 32 and 34 carbon atoms with mutual specificity correlation in mixture, which belongs to the field of chemistry. The alcohol mixture has specific biological properties, and can be used as the active ingredient of medicine for treating hypercholesterolemia and type II hyperlipoproteinemia of patients and reducing sexual act disorders. In addition, the alcohol mixture can be used as a systemic invigorator.
Description
The present invention relates to chemical field, particularly relate to by the method that makes the higher primary aliphatic alcohols mixture that contains 24 to 34 carbon atoms in the sugar-cane wax, the fatty alcohol that wherein contains different carbon atoms is that particular association is arranged each other in said mixture.
The method according to this invention, resulting higher primary aliphatic alcohols mixture has specific biological property, and its formula of medicine that can suffer from the II type patient of hypercholesterolemia and hyperlipoproteinemia and be used for reducing the sexual behaviour obstacle in treatment is as activeconstituents (patent application CU185/90).It also can be used as general tonic.
Sugar-cane wax and its natural origin-filter mud are interesting materials always, and this is not only the industrial application because of them, and are based on their chemical constitution.
According to the difference of kind, the content of wax is between 0.1% to 0.3% in the sugarcane.In the agro-industry course of processing, have only 40% wax to be diluted in the juice, rest part is then lost in bagasse.This is in 40%, has 95% to be absorbed by filter mud, and crude tallow is promptly by making in the filter mud.This wax is by ester, aldehyde, and ketone, hydro carbons, lipid acid and free alcohol constitute, and wherein the amount of each composition is because of the kind and the source of sugarcane plants and to produce the employed technology of wax different.
Existing several article authors have studied the straight-chain fatty alcohol that obtains by in the sugarcane byproduct, have studied their composition and main character.Therefore people such as J.A.Lamberton proposes to separate these pure different methods and uses gas-chromatography to identify their method at Australian Journal ofChemistry13 from cuticular among the 261-8 (1959).
Have and related to the method for from various waxes, separating the inhomogeneity compound in several pieces of articles, for example, Hcrn and Martic are at Journalof Science Food and Agriculture 10, proposed from sugarcane epidermis wax, to make the method for Fatty Alcohol(C12-C14 and C12-C18) in 571 (1957), the spirituous solution that this method is based on potassium hydroxide carries out the homogeneous saponification, and the nonsaponifiable material of esterification step of going forward side by side is carried out molecular distillation then.
Another kind of method of separating alcohol mixture is by efficient high vacuum post.Be to produce alcohol more at last with potassium hydroxide.
In another work of being finished by people such as J.A.Lamberton, they have proposed the method for saponification similar to aforementioned person, and after isolating unsaponified material, separates from sugarcane epidermis wax by the alumina column chromatography method pure, thereby obtain three parts:
-a spot of hydrocarbon part
-another part contains the carboxyl and the carbonyl compound of mixing, and the both is with the mixture wash-out of normal hexane/toluene,
Three parts of-Di are to contain alcohol moiety (40%) with the chloroform wash-out.
The different means of another that mention in this article are the distillation of high vacuum wax, chemical separation carbonyl compound and use the remaining wax of Petroleum ether extraction.After carrying out solvent evaporation and the rest part acetylize handled, further separate by alumina column chromatography.At last, obtain isolating alcohol, show behind the recrystallization that in ethanol its fusing point is 80～82 ℃ by basic hydrolysis.
People such as Z.H.Kranz are at Australian Journal ofChemistry13, proposed among the 498-505 (1960) to change into acid and pass through the further isolating method of column chromatography based on the formoxy-that will be contained in the sugar-cane wax, they have isolated the alcohol (25%) that similar productive rate is arranged to aforementioned person by this method.Wherein used gas-chromatography to identify these products.
From the viewpoint of analyzing, all these methods all are valuable, but realize producing in enormous quantities owing to using uneconomic means such as column chromatography and molecular distillation to be difficult to.
As from Research Industry 30, can see on the 95-101 (1985), people such as R.K.Gupta solve these problems to a certain extent, wherein they have studied from refining sugar-cane wax and have extracted these pure methods, during this method is based on all one by one mutually by in temperature being 100 ℃ to 120 ℃ fusing waxes down, and add the sodium hydroxide be dissolved in 10% (weight) in the similar body ponding and carry out saponification, finished saponification in 1.5 hours through being interrupted to stir; The product that the cooling reaction obtains under room temperature is poured content furnace pot into and is almost evaporated remaining water fully.
The product that will so obtain and benzene azeotropic distillation at last and drying.Dried material is easy to powder, and uses the benzole soln of ethylene dichloride (DCE) to extract then, obtains the acid of salt form.
Another improvement of this technology is based on use benzene/ethanol and makes solvent, uses 18.5N potassium hydroxide to refining wax saponification 10 to 26 hours.Underpressure distillation saponified material in vapor bath removes and desolvates, and it is Powdered that products therefrom during drying is transformed at an easy rate, therefrom extracts alcohol by preceding method then.Under two kinds of situations, productive rate is 7.5%, and the inconvenience of this method is to use toxic organic solvent.
Having proposed for Japanese Patent JP119514 number a kind of is the method that obtains the higher primary aliphatic alcohols mixture the sugar-cane wax from animal and vegetable wax, and this method is based on saponified fat family ester, uses enough solvents then, is 60～300kg/cm at pressure
2With temperature be under 25～100 ℃ of conditions, by at subcritical and supercritical state CO
2In the fluid extraction alcohol mixture, the result shows and can carry out selective extraction according to solubleness and low temperature and pressure change.Be applied to the method for sugarcane according to this, might obtain C20～C36 alcohol mixture of 5%.
Proposed a kind of very similar methods that is used to extract wax for Japanese Patent JP87-87537 number, generally speaking, this method is based on by subcritical and supercritical state CO
2Fluid extract with ethene.Also be situated between among the Japanese Patent JP79-10539 and begun by in subcritical method of from its mixture, separating organic compound with the fluid of supercritical state.
Method of the present invention is based on this technology of sugar-cane wax that melts in advance with spissated sodium hydroxide, potassium hydroxide or the saponification of aqua calcis homogeneous phase.The concentration of hydroxide solution must make corresponding oxyhydroxide and treat that the part by weight of saponified wax is 10～25%; The saponification process should under agitation be carried out 3 to 10 hours.
Resulting solids is added the solid-liquid extractor, be selected from hexane, acetone, methyl, ethyl ketone, ethanol, methyl alcohol or Virahol, chloroform, methylene dichloride, 1 with q.s, the organic solvent of 2-ethylene dichloride, normal heptane, benzene, toluene or its mixture optionally extracts alcohol mixture.This leaching process carried out 10 to 20 hours.
Should at room temperature cool off resulting extract, thereby crystallization goes out to contain the solids of impure mixture of higher alcohols.Use then above-mentioned solvent or its mixture successfully crystallization go out required product.Productive rate reaches 20～30%, and the purity of mixture of higher aliphatic alcohols is 90～95%.
The higher primary aliphatic alcohols mixture that so obtains is made up of the alcohol that contains 24 to 34 carbon atoms.This is a kind of mixture of non-standard white, and its fusing point is 78.5 to 82.5 ℃.
For in the fused silica capillary column by these alcohol of gas chromatographic analysis, must by N-methyl-N-TMS-trichloroacetamide (MSTFA) make alcohol derivative.Table 1 has shown the composition of this higher primary aliphatic alcohols mixture.
Table 1: form by the qualitative and quantitative of the higher primary aliphatic alcohols mixture that makes in the sugar-cane wax
The percentage of component in mixture
1-tetracosanol 0.5-5.0%
1-hexacosyl alcohol 5.0-15.0%
1-Heptacosanol 0.5-5.0%
1-octacosanol 55.0-80.0%
1-nonacosanol 0.5-3.0%
1-triacontanol 6.0-20.0%
The percentage of component in mixture
1-laccerol 1.0-10.0%
1-inearnatyl alcohol 0.0-2.5%
Compare with other currently known methodss, the present invention propose by the method for producing the higher primary aliphatic alcohols mixture in the sugar-cane wax, have the advantage that reaction times, productive rate and purity all are improved significantly.
By embodiment the present invention is described in further detail below, these embodiment do not constitute limitation of the scope of the invention.
Embodiment 1
At the 100-110 ℃ of following refining wax that obtains in by sugarcane of fusing 1000g, add 200g again and be dissolved in potassium hydroxide in the 150ml water.This process under agitation continues 5 hours.In the solid-liquid extraction system, use and melt by extracting alcohol mixture in the gained solids, extracted altogether 12 hours.Cooling is extract obtained under room temperature, thereby at first in heptane, crystallization goes out the mixture of higher primary aliphatic alcohols in acetone then.The result obtains 245 gram alcohol mixtures, and its purity reaches 94.44%, and the about 79.0-81.5 of fusing point ℃, table 2 has shown the qualitative and quantitative composition of gained alcohol mixture.
Table 2: the qualitative and quantitative composition of gained higher primary aliphatic alcohols
The percentage of the composition alcohol of identifying
Tetracosanol 2.81
Hexacosyl alcohol 7.57
Heptacosanol 2.81
Octacosanol 73.79
Nonacosanol 0.50
The percentage of the composition alcohol of identifying
Triacontanol 5.43
Laccerol 1.35
Inearnatyl alcohol 0.18
Amount to 94.44
Embodiment 2
At the 85-100 ℃ of following waxy stone that make in by sugarcane of fusing 2kg, be dissolved in sodium hydroxide in the 200ml water to wherein adding people 300g, the saponification process was carried out 4 hours under stirring.In conventional solid-liquid extraction system, use chloroform extraction alcohol mixture meter 10 hours, the resulting extract of cooling under room temperature, in sherwood oil (50-70 ℃) then, the resulting cured article of recrystallization in chloroform/methylethyl alcohol/ketone mixtures at last.The result obtains 405g purity and reaches 90.12% said alcohol mixture.This mixture fusing point is 77.5-79.5 ℃.Table 3 has shown the qualitative and quantitative composition of gained alcohol mixture.
Table 3: the qualitative and quantitative composition of gained higher fatty alcohol
The percentage of the composition alcohol of having identified
Tetracosanol 4.17
Hexacosyl alcohol 9.04
Heptacosanol 1.08
Octacosanol 60.92
Nonacosanol 3.50
Triacontanol 10.66
Laccerol 0.65
Inearnatyl alcohol 0.10
Amount to 90.12
Embodiment 3
The calcium hydroxide that 8kg is dissolved in 7 premium on currency is added to 50kg in advance in 100-120 ℃ of rough sugar-cane wax that melts down.The saponification process was carried out 7.5 hours under stirring.In the solid-liquid extraction system, use sherwood oil (50-70 ℃) to extract alcohol mixture, extracted altogether 12 hours.At room temperature cool off resulting extract.Then in the mixture of chloroform and heptane, and further 1, this solids of recrystallization in the 2-ethylene dichloride.It is 93.97% 10.7kg alcohol mixture that the result obtains purity.The fusing point of this mixture is 79.5-81. ℃.Table 4 shows the qualitative and quantitative composition of gained alcohol mixture.
Table 4: the qualitative and quantitative composition of resulting alcohol mixture
The percentage of the composition alcohol of having identified
Tetracosanol 2.11
Hexacosyl alcohol 9.88
Heptacosanol 3.06
Octacosanol 68.30
Nonacosanol 0.52
Triacontanol 8.51
Laccerol 1.39
Inearnatyl alcohol 0.20
Amount to 93.97
Embodiment 4
The calcium hydroxide adding that 8.6kg is dissolved in 4.5 premium on currency is pre-prior in the 100-120 ℃ of rough sugar-cane wax of 50kg that melts down, carried out continuously 3 hours under stirring in the saponification process.In the solid-liquid extractor, use methylene dichloride to make the solvent extraction alcohol mixture after 12 hours.At room temperature place cooling with extract obtained, and first in the mixture of chloroform and acetone, and again at methyl, recrystallization goes out the solids of gained in the ethyl ketone.It is 90.5% alcohol mixture that the result obtains 9.8kg purity.The fusing point of this mixture is 78.5-80.5 ℃.Table 5 has shown the qualitative and quantitative composition of gained alcohol mixture.
Table 5: the quantitative and qualitative composition of resulting mixture of higher aliphatic alcohols
The percentage of the composition alcohol of having identified
Tetracosanol 3.15
Hexacosyl alcohol 11.88
Heptacosanol 4.14
Octacosanol 60.60
Nonacosanol 1.52
Triacontanol 7.93
Laccerol 1.09
Inearnatyl alcohol 0.18
Amount to 90.49
Embodiment 5
Earlier the refining sugar-cane wax of 20kg is melted under 100-110 ℃ temperature, add 3.7kg then and be dissolved in KOH in 3.0 premium on currency, the saponification process under agitation continues 5 hours.Use heptane to make solvent, extract alcohol mixture in the Soxhlet extractor, meter extracted 14 hours.At room temperature cool off extract.Elder generation is in the mixture of sherwood oil (50-70 ℃) and chloroform then, and again 1, recrystallization goes out the said extracted thing in the 2-ethylene dichloride.The result obtains purity and reaches 92.56% the said alcohol mixture of 3.8kg, and the fusing point of this mixture is 77.5-79.0 ℃.Table 6 has shown the qualitative and quantitative composition of gained alcohol mixture.
Table 6: the qualitative and quantitative composition of resulting mixture of higher aliphatic alcohols
The percentage of the composition alcohol that identifies
Tetracosanol 3.05
Hexacosyl alcohol 9.06
Heptacosanol 3.10
Octacosanol 62.10
Nonacosanol 1.22
Triacontanol 8.18
Laccerol 5.71
Inearnatyl alcohol 0.14
Amount to 92.56
Claims (1)
1. from sugar-cane wax, make the method for high grade primary alcohol mixture with 24-34 carbon atom, said alcohol mixture has following composition: the 0.5%-5.0%1-tetracosanol, the 5.0-15.0%1-hexacosyl alcohol, the 0.5-5.0%1-Heptacosanol, the 55.0-80.0%1-octacosanol, the 0.5-3.0%1-nonacosanol, the 6.0-20.0%1-triacontanol, 1.0-10.0%1-laccerol and 0.0-2.5%1-inearnatyl alcohol, the method is characterized in that and make the sugar-cane wax fusing, in homogeneous phase, use sodium hydroxide, calcium hydroxide or potassium hydroxide carry out saponification, wherein the concentration of oxyhydroxide is 10-20g/100g wax, saponification step is lasted 3 to 10 hours, uses following extraction solvent then: aliphatic hydrocrbon, acetone, methyl ethyl ketone, methyl alcohol, ethanol or Virahol, chloroform, methylene dichloride, 1, the 2-ethylene dichloride, benzene, toluene and their mixture extract higher primary aliphatic alcohols in solid-liquid extraction system, coextraction 15-20 hour, when needing, with above-mentioned solvent and/or its mixture recrystallization crude product.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 92100246 CN1030763C (en) | 1992-01-15 | 1992-01-15 | Method for obtaining a mixture of higher aliphatic alcohols from sugar cane wax |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 92100246 CN1030763C (en) | 1992-01-15 | 1992-01-15 | Method for obtaining a mixture of higher aliphatic alcohols from sugar cane wax |
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| CN1074435A CN1074435A (en) | 1993-07-21 |
| CN1030763C true CN1030763C (en) | 1996-01-24 |
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| CN 92100246 Expired - Lifetime CN1030763C (en) | 1992-01-15 | 1992-01-15 | Method for obtaining a mixture of higher aliphatic alcohols from sugar cane wax |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187677A (en) * | 2016-07-19 | 2016-12-07 | 北京颐方生物科技有限公司 | A kind of method and application preparing senior fat primary alcohol mixture with cerosin |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1091093C (en) * | 1999-12-30 | 2002-09-18 | 广东省食品工业研究所 | Higher fatty alcohol aliphatic ester and use thereof |
| CN103439451B (en) * | 2013-08-16 | 2015-06-17 | 山东师范大学 | Extraction and thin-layer chromatographic scanning detection method for octacosanol from Antarctic krill |
| CN105348042A (en) * | 2015-11-25 | 2016-02-24 | 南方医科大学 | Method for preparing higher aliphatic alcohol from bagasse |
-
1992
- 1992-01-15 CN CN 92100246 patent/CN1030763C/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106187677A (en) * | 2016-07-19 | 2016-12-07 | 北京颐方生物科技有限公司 | A kind of method and application preparing senior fat primary alcohol mixture with cerosin |
| CN106187677B (en) * | 2016-07-19 | 2019-03-26 | 北京颐方生物科技有限公司 | A kind of method and application preparing senior fat primary alcohol mixture with cerosin |
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| Publication number | Publication date |
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| CN1074435A (en) | 1993-07-21 |
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Expiration termination date: 20120115 Granted publication date: 19960124 |