CN102408310A - Method for preparing high-purity solanesol by utilizing prepared opium paste - Google Patents
Method for preparing high-purity solanesol by utilizing prepared opium paste Download PDFInfo
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- CN102408310A CN102408310A CN2011103274086A CN201110327408A CN102408310A CN 102408310 A CN102408310 A CN 102408310A CN 2011103274086 A CN2011103274086 A CN 2011103274086A CN 201110327408 A CN201110327408 A CN 201110327408A CN 102408310 A CN102408310 A CN 102408310A
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Abstract
The invention discloses a method for preparing high-purity solanesol by utilizing prepared opium paste, which comprises the following steps of: (1) placing the prepared opium paste in acetylation reagent for reaction to obtain prepared opium paste acetylation product; (2) heating and refluxing the prepared opium paste acetylation product for dissolving in organic solvent, filtering the hot reaction solution to remove impurities, taking filter liquor, decompressing and evaporating to dryness to obtain oily matters; (3) adding ethanol and sodium hydroxide to the oily matters for heating, stirring and saponification reaction, after the saponification reaction, cooling the reaction solution, filtering, taking filter liquor, concentrating to obtain concentrated solution, freezing the concentrated solution at low temperature and filtering to obtain crystallized matters; and (4) decolorizing and recrystallizing the crystallized matters to obtain the high-purity solanesol. The method can increase content of free solanesol in the prepared opium paste, the used solvent has low toxicity and the solanesol has high extraction rate and high purity and is easy to realize industrialization production.
Description
Technical field
The concrete a kind of method of extracting eggplant Buddhist nun alcohol of the present invention is specifically related to a kind of method of utilizing prepared opium paste to prepare high-purity solanesol.
Background technology
Eggplant Buddhist nun alcohol is a kind of polyisoprene alcohol, and molecular structural formula is H (CH
2C (CH
3) CHCH
2)
9OH, relative molecular weight are 631, and pure article are white powdery solid, and fusing point is 41 ℃.Eggplant Buddhist nun alcohol is the Fatty Alcohol(C12-C14 and C12-C18) of long-chain, and low-pole is soluble in organic solvent, and is water insoluble, the certain solubleness of oil in alcoholic solvent.Eggplant Buddhist nun alcohol is synthesizing coenzyme Q 10 and vitamin K as a kind of important medicine intermediate
2Important source material, this external field of medicaments, its derived product also have the prevention and the treatment cardiovascular and cerebrovascular diseases effect.The existing way of eggplant Buddhist nun alcohol in tobacco leaf mainly is two kinds of free state and esterification attitudes, and wherein the eggplant Buddhist nun alcohol of free state accounts for 8%, and the eggplant Buddhist nun alcohol of esterification attitude accounts for 6%.
The method of being announced at present for preparing eggplant Buddhist nun alcohol is a lot; Described mode of production general expression adopts low polar organic solvent from tobacco leaf, to extract and obtains prepared opium paste, then handles multiple solvent or the extraction of polycomponent mixed solvent multistep through saponification; Recrystallization, column chromatography etc. obtain pure article.As number of patent application be 200510111768.7 and number of patent application be to use the resin column chromatography in two patent disclosed methods such as 2004100067949.X, reagent type is many, operation easier is big.Number of patent application is to have used multiple solvents such as hexanaphthene, acetone-alcohol in 200410040400.1 the disclosed method of patent in addition, has improved productive rate and content though used saponification process, and the organic solvent kind is numerous, causes difficult solvent recovery.
How to simplify technology, reduce solvent species, and can improve the purity that the extraction yield that extracts eggplant Buddhist nun alcohol in the raw material finally improves eggplant Buddhist nun alcohol and become the technical problem that needs to be resolved hurrily in this area.
Summary of the invention
The object of the present invention is to provide a kind of technology simple, use that solvent species is few, eggplant Buddhist nun ethanol-extracted rate high, the high prepared opium paste that utilizes of eggplant Buddhist nun alcohol purity prepares the method for high-purity solanesol.
Above-mentioned purpose of the present invention realizes through following technique means: a kind of method of utilizing prepared opium paste to prepare high-purity solanesol contains following steps:
(1) after placing acetylation reagent to react prepared opium paste the acetylate of prepared opium paste;
(2) with acetylate reflux dissolving in organic solvent of prepared opium paste, while hot with the reacting liquid filtering removal of impurities, get filtrating and obtain oily matter subsequently through evaporated under reduced pressure;
(3) adding ethanol and sodium hydroxide carry out the heated and stirred saponification reaction in oily matter, and saponification reaction finishes the reaction solution cooled and filtered, gets filtrating, get liquid concentrator after concentrating, and with liquid concentrator freezing after-filtration, get crystallisate;
(4) crystallisate promptly obtains highly purified eggplant Buddhist nun alcohol behind decolouring, recrystallization.
In above-mentioned steps:
Acetylation reagent described in the step of the present invention (1) is diacetyl oxide, Acetyl Chloride 98Min. or acetate, and the temperature of acetylization reaction is that 60 ℃-80 ℃, reaction times are 3-5 hour, and the consumption of acetylation reagent accounts for the 10-15% of prepared opium paste quality.
In the step of the present invention (2) with the acetylate of prepared opium paste in organic solvent in 60 ℃ of-80 ℃ of reflux dissolvings, and the saponification reaction 2 ~ 3 hours of refluxing.
Organic solvent of the present invention is an aqueous ethanolic solution, and wherein the alcoholic acid volumn concentration is 50 ~ 70%, and the consumption of aqueous ethanolic solution is 8 ~ 10 times of prepared opium paste total mass.
In oily matter, add ethanol in the step of the present invention (3) and sodium hydroxide carried out the heated and stirred saponification reaction 3 ~ 4 hours in 70 ℃ of-80 ℃ of oil baths.
Consumption of ethanol according to the invention accounts for 10-20 times of oily matter total mass, and its volumn concentration is 90 ~ 95%, and the consumption of said sodium hydroxide accounts for 4 ~ 7% of oily matter total mass.
In the step of the present invention (3) after the saponification reaction with reaction solution in 5 ~ 8 hours after-filtration of-5 ℃ ~ 0 ℃ cooling, filtrating is concentrated into after half of original volume liquid concentrator; Liquid concentrator in-20 ℃ ~-25 ℃ freezing 8 ~ 10 hours after-filtration, is got crystallisate.
The process of crystallisate decolouring is in the step of the present invention (4): crystallisate is placed aqueous ethanolic solution, and the adjusting temperature of reaction is 80 ℃ and carried out heating reflux reaction 1 ~ 1.5 hour under the effect of gac.
The volumn concentration of wherein said aqueous ethanolic solution is preferably 90%, and its consumption preferably accounts for 8 ~ 15 times of crystallisate total mass, and the consumption of gac preferably accounts for 4% ~ 6% of crystallisate quality.
In the step of the present invention (4) during crystallization-20 ℃ ~-25 ℃ freezing and crystallizings 8 ~ 10 hours, promptly get purity, to be higher than 90% eggplant Buddhist nun pure.
Compared with prior art, the present invention has following beneficial effect:
(1) yield and the content of prepared opium paste removal of impurities after acetylize is handled after purification is handled in saponification, can the raising again eggplant Buddhist nun alcohol among the present invention;
(2) solvent species that adopts among the present invention is less, and it is simple to reclaim reagent;
(3) integrated artistic of the present invention is simple, and is with short production cycle;
(4) preparing method's of the present invention production technique cost is low, is easy to realize suitability for industrialized production, and the pure purity of eggplant Buddhist nun that adopts the inventive method to prepare reaches more than 90%.
Embodiment
Below the present invention is described further, but embodiment of the present invention is not limited to following embodiment introduction, all variation that is equal to or flexible categories of doing according to method of the present invention that all should be regarded as the present invention's protection.Below raw materials used, except that special indicating, be commercially available.
Embodiment 1
Will be by tobacco leaf through No. six solvent extractions and concentrate prepared opium paste 100 that dried solvent obtains and restrain in the acetylation reagent diacetyl oxide and react, the temperature of reaction is that 60 ℃, reaction times are 3.5 hours, the consumption of diacetyl oxide is 11 grams.Reaction finishes the back and adds the ethanolic soln of 900 grams 55% in the acetylate and dissolve in 60 ℃ of reflux, and return time is 2 hours.Filtered while hot removal of impurities subsequently, last evaporated under reduced pressure filtrating obtains oily matter 78.6 grams.Add 1200 gram concentration in the oily matter and be 90% ethanolic soln and 4.7 gram sodium hydroxide, mixture was in 70 ℃ of heated and stirred saponification of oil bath 3 hours, and reaction finishes afterreaction liquid in-5 ℃ of coolings 6 hours; Filtering and impurity removing; Mother liquid obtained be evaporated to half volume with liquid concentrator after-20 ℃ of freezing 9 hours after-filtration obtain light yellow crystallisate 15.6 grams, the crystallisate heating is dissolved in 165 grams, 90% ethanolic soln, add 0.7 gram gac subsequently; 80 ℃ of 1.5 hours after-filtration that reflux; Filtrate in-20 ℃ freezing 8 hours, filter and to obtain 11.3 gram eggplant Buddhist nuns alcohol, measuring eggplant Buddhist nun alcohol content through HPLC is 92.12%.
Embodiment 2
Will be by tobacco leaf through No. six solvent extractions and concentrate prepared opium paste 100 that dried solvent obtains and restrain in acetylation reagent and react, the temperature of acetylization reaction is that 70 ℃, reaction times are 4 hours, the consumption of diacetyl oxide is 13 grams.Reaction finishes the back and adds the ethanolic soln of 800 grams 70% in the acetylate and dissolve in 70 ℃ of reflux, and return time is 2.5 hours.Filtered while hot removal of impurities subsequently, last evaporated under reduced pressure filtrating obtains oily matter 80.7 grams.Past oily matter adding 1200 gram concentration are 90% ethanolic soln and 4.8 gram sodium hydroxide, and mixture reacts the afterreaction liquid that finishes and cooled off 6 hours in-5 ℃ in 75 ℃ of heated and stirred saponification of oil bath 3.5 hours; Filtering and impurity removing; Mother liquid obtained be evaporated to half volume with liquid concentrator after-20 ℃ of freezing 8 hours after-filtration obtain light yellow crystallisate 16.4 grams, the crystallisate heating is dissolved in 160 grams, 90% ethanolic soln, add 0.8 gram gac subsequently; 80 ℃ of 1 hour after-filtration that refluxes; Filtrate in-20 ℃ freezing 8 hours, filter and to obtain 10.2 gram eggplant Buddhist nuns alcohol, measuring eggplant Buddhist nun alcohol content through HPLC is 91.23%.
Embodiment 3
Will be by tobacco leaf through No. six solvent extractions and concentrate prepared opium paste 100 that dried solvent obtains and restrain in acetylation reagent and react, the temperature of acetylization reaction is that 80 ℃, reaction times are 5 hours, the consumption of diacetyl oxide is 15 grams.Reaction finishes the back and adds the ethanolic soln of 1000 grams 60% in the acetylate and dissolve in 80 ℃ of reflux, and return time is 3 hours.Filtered while hot removal of impurities subsequently, last evaporated under reduced pressure filtrating obtains oily matter 76.7 grams.Past oily matter adding 1534 gram concentration are 90% ethanolic soln and 4.7 gram sodium hydroxide, and mixture reacts the afterreaction liquid that finishes and cooled off 8 hours in-4 ℃ in 80 ℃ of heated and stirred saponification of oil bath 4 hours; Filtering and impurity removing; Mother liquid obtained be evaporated to half volume with liquid concentrator after-10 ℃ of freezing 10 hours after-filtration obtain light yellow crystallisate 15.8 grams, the crystallisate heating is dissolved in 237 grams, 90% ethanolic soln, add 0.8 gram gac subsequently; 80 ℃ of 1.5 hours after-filtration that reflux; Filtrate in-25 ℃ freezing 10 hours, filter and to obtain 10.9 gram eggplant Buddhist nuns alcohol, measuring eggplant Buddhist nun alcohol content through HPLC is 92.43%.
The foregoing description is a preferred implementation of the present invention; But embodiment of the present invention is not restricted to the described embodiments; Other any do not deviate from change, the modification done under spirit of the present invention and the principle, substitutes, combination, simplify; All should be the substitute mode of equivalence, be included in protection scope of the present invention.
Claims (10)
1. method of utilizing prepared opium paste to prepare high-purity solanesol is characterized in that containing following steps:
(1) after placing acetylation reagent to react prepared opium paste the acetylate of prepared opium paste;
(2) with acetylate reflux dissolving in organic solvent of prepared opium paste, while hot with the reacting liquid filtering removal of impurities, get filtrating and obtain oily matter subsequently through evaporated under reduced pressure;
(3) adding ethanol and sodium hydroxide carry out the heated and stirred saponification reaction in oily matter, and saponification reaction finishes the reaction solution cooled and filtered, gets filtrating, get liquid concentrator after concentrating, and with liquid concentrator freezing after-filtration, get crystallisate;
(4) crystallisate promptly obtains highly purified eggplant Buddhist nun alcohol behind decolouring, recrystallization.
2. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 1; It is characterized in that: the acetylation reagent described in the step (1) is diacetyl oxide, Acetyl Chloride 98Min. or acetate; The temperature of acetylization reaction is that 60 ℃-80 ℃, reaction times are 3-5 hour, and the consumption of acetylation reagent accounts for the 10-15% of prepared opium paste quality.
3. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 1 is characterized in that: in the step (2) with the acetylate of prepared opium paste in organic solvent in 60 ℃ of-80 ℃ of reflux dissolvings, and the saponification reaction 2 ~ 3 hours of refluxing.
4. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 3 is characterized in that: described organic solvent is an aqueous ethanolic solution, and wherein the alcoholic acid volumn concentration is 50 ~ 70%, and the consumption of aqueous ethanolic solution is 8 ~ 10 times of prepared opium paste total mass.
5. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 1 is characterized in that: in oily matter, add ethanol in the step (3) and sodium hydroxide carried out the heated and stirred saponification reaction 3 ~ 4 hours in 70 ℃ of-80 ℃ of oil baths.
6. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 5; It is characterized in that: said consumption of ethanol accounts for 10-20 times of oily matter total mass; Its volumn concentration is 90 ~ 95%, and the consumption of said sodium hydroxide accounts for 4 ~ 7% of oily matter total mass.
7. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 1 is characterized in that: in the step (3) after the saponification reaction with reaction solution in 5 ~ 8 hours after-filtration of-5 ℃ ~ 0 ℃ cooling, filtrating is concentrated into after half of original volume liquid concentrator; Liquid concentrator in-20 ℃ ~-25 ℃ freezing 8 ~ 10 hours after-filtration, is got crystallisate.
8. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 1; It is characterized in that: the process of crystallisate decolouring is in the step (4): crystallisate is placed aqueous ethanolic solution, and the adjusting temperature of reaction is 80 ℃ and carried out heating reflux reaction 1 ~ 1.5 hour under the effect of gac.
9. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 8 is characterized in that: the volumn concentration of said aqueous ethanolic solution is 90%, and its consumption accounts for 8 ~ 15 times of crystallisate total mass, and the consumption of gac accounts for 4% ~ 6% of crystallisate quality.
10. the method for utilizing prepared opium paste to prepare high-purity solanesol according to claim 1 is characterized in that: in the step (4) during crystallization-20 ℃ ~-25 ℃ freezing and crystallizings 8 ~ 10 hours, promptly get purity, to be higher than 90% eggplant Buddhist nun pure.
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| CN 201110327408 CN102408310B (en) | 2011-10-25 | 2011-10-25 | Method for preparing high-purity solanesol by utilizing prepared opium paste |
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| CN 201110327408 CN102408310B (en) | 2011-10-25 | 2011-10-25 | Method for preparing high-purity solanesol by utilizing prepared opium paste |
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| CN102408310A true CN102408310A (en) | 2012-04-11 |
| CN102408310B CN102408310B (en) | 2013-10-30 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013731A (en) * | 1969-04-24 | 1977-03-22 | Nisshin Flour Milling Co., Ltd. | Process for the manufacture of solanesol |
| CN1676502A (en) * | 2004-04-03 | 2005-10-05 | 杨群力 | Solanesol refining method |
| CN101284766A (en) * | 2008-06-04 | 2008-10-15 | 云南瑞升烟草技术（集团）有限公司 | Process for finely purifying high-purity solanesol form coarse cream of solanesol |
| CN101935269A (en) * | 2010-09-30 | 2011-01-05 | 长安大学 | Method for precipitating, separating and purifying solanesol |
| CN101940361A (en) * | 2010-10-11 | 2011-01-12 | 广东中烟工业有限责任公司 | Processing method of waste tobacco |
| CN101979613A (en) * | 2010-10-28 | 2011-02-23 | 西北师范大学 | Ultrasound enzyme-assisted solanesol extracting method |
-
2011
- 2011-10-25 CN CN 201110327408 patent/CN102408310B/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4013731A (en) * | 1969-04-24 | 1977-03-22 | Nisshin Flour Milling Co., Ltd. | Process for the manufacture of solanesol |
| CN1676502A (en) * | 2004-04-03 | 2005-10-05 | 杨群力 | Solanesol refining method |
| CN101284766A (en) * | 2008-06-04 | 2008-10-15 | 云南瑞升烟草技术（集团）有限公司 | Process for finely purifying high-purity solanesol form coarse cream of solanesol |
| CN101935269A (en) * | 2010-09-30 | 2011-01-05 | 长安大学 | Method for precipitating, separating and purifying solanesol |
| CN101940361A (en) * | 2010-10-11 | 2011-01-12 | 广东中烟工业有限责任公司 | Processing method of waste tobacco |
| CN101979613A (en) * | 2010-10-28 | 2011-02-23 | 西北师范大学 | Ultrasound enzyme-assisted solanesol extracting method |
Non-Patent Citations (1)
| Title |
|---|
| 王超杰等: "二元酸茄呢醇乳糖和麦芽糖糖酯合成及生理活性测试研究", 《有机化学》, vol. 23, no. 10, 25 October 2003 (2003-10-25), pages 1102 - 1106 * |
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