CN1686988A - Method for preparing high pure solanesol - Google Patents
Method for preparing high pure solanesol Download PDFInfo
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- CN1686988A CN1686988A CN 200510063053 CN200510063053A CN1686988A CN 1686988 A CN1686988 A CN 1686988A CN 200510063053 CN200510063053 CN 200510063053 CN 200510063053 A CN200510063053 A CN 200510063053A CN 1686988 A CN1686988 A CN 1686988A
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Abstract
The present invention adopts solanesol extract whose purity is greater than 10% as raw material, does not make saponification treatment, uses solvent to dissolve, and adds adsorbing agent to make mixing, concentration and adsorption, and adopts indstrial solid-liquid phase column chromatographic separation technique, uses polar and low-polar or mixed solvent to make elution to remove impurities, and makes the section richly-containing solenesol undergo the processes of removing impurity, concentration, freeze-crystallization and vacuum-drying so as to obtaain the high-purity solanesol fine product whose purity is greater than 96%.
Description
The English name of technical field eggplant Buddhist nun alcohol is Solanesol, and chemical name is 3,7,11,15,19,23,27,31,35-nine methyl-2,6,10,14,18,22,26,30, and 34-hexatriacontane nine rare-1-alcohol, molecular formula is H[CH
2C (CH
3) CHCH
2]
9OH, molecular weight is 631, is the essential raw material of synthesizing coenzyme Q 10 and multiprenylmenaquinone.Studies show that in recent years, ubiquinone 1 is having unique curative effect aspect the cardiovascular and cerebrovascular diseases in treatment, and in treatment vitamin C deficiency, duodenal ulcer and stomach ulcer, gangrenosum acne periodontitis, viral hepatitis aspect have apparent curative effect.Therefore the extraction and purification process of eggplant Buddhist nun alcohol is also more and more paid close attention to by people, particularly highly purified eggplant Buddhist nun alcohol elaboration.
Background technology eggplant Buddhist nun alcohol is present in animal viscera and some plant leafs, and is wherein the highest with the content in the tobacco leaf.That patent CN 1056486A, CN 1094705A, CN 1087076A, CN 1108641A, spy open is clear 52139711, to open clear 63190840 etc. be raw material to pulverize tobacco leaf to the spy, with normal hexane or No. 6 solvent oil continuous extractions or interrupted extraction, get solanesol extract after concentrating, product purity reaches about 20%.Patent CN 1094920C, CN 1302568A adopt supercutical fluid and select to add the different solvent extractions of paying and obtain containing eggplant Buddhist nun alcohol crude product, and content reaches about 40%.CN1400300A is raw material with the tobacco extract, adopts hight atmospheric molecular distillation and minor axis distillation, and staging treating obtains eggplant Buddhist nun alcohol enriched substance, and content reaches 10-20%.CN1534008A filters tobacco leaf and solvent making beating, and filter cake adopts the extraction of ethanol cavitation, filter, filtrate merging concentrates, saponification, n-hexane extraction, washing, adsorbents adsorb is filtered, and filtrate concentrates, the normal hexane crystallization, the acetonitrile recrystallization obtains purity greater than the pure product of 90% eggplant Buddhist nun, and yield is 0.4-0.5%.Patent CN 1345711A is a raw material with the alcohol of the eggplant Buddhist nun more than 70% crude product, adopt the silica gel adsorption chromatography method, with normal hexane-1,2-ethylene dichloride-acetone is eluent, collects to be rich in eggplant Buddhist nun alcohol section, adopts gel permeation chromatography again, with normal hexane is eluent, eggplant Buddhist nun alcohol section is rich in collection, concentrates, and freezing and crystallizing gets purity greater than the pure product of 90% eggplant Buddhist nun.
Aforesaid method has the following disadvantages:
1, above invention is mainly the production technology of solanesol extract and crude product, obtain high-purity solanesol and still need adopt other technology to carry out deep processing.
Operation cost was very high when 2, the distillation of supercritical extraction and hight atmospheric molecular was used for eggplant Buddhist nun alcohol industrial production, did not reach the cost performance that meets market demands, was difficult to realize industrialization.
3, complicated component in the tobacco extract, alkaline saponification or add acid neutralization or washing not only makes whole flow process very long, and solvent consumption increases, and reaction generates unknown at present impurity, and when being purified to the product of 90% purity, quality product and purity there is no improvement.
With the tobacco extract is raw material, alkaline saponification, after washing or the neutralization again through repeatedly crossing silica gel column chromatography and gel chromatography, though can obtain eggplant Buddhist nun alcohol elaboration, but long flow path, yield are low, silica gel and gel consuming cost height, product stability are poor, are difficult to control when being used for synthesizing coenzyme Q 10.
Summary of the invention the purpose of this invention is to provide a kind of stable, industrialization, purifies and obtain the method for high-purity solanesol at low cost.The present invention adopts purity to make raw material greater than 10% solanesol extract, not doing saponification handles, use dissolution with solvents, add sorbent material and mix concentrated absorption, adopt industrial solid-liquid phase column chromatography separation technology, use polarity, weak polar solvent or mixed solvent wash-out, segmentation is removed and the eggplant Buddhist nun alcohol impurity that polarity is different or molecular weight difference is bigger, to be rich in eggplant Buddhist nun alcohol section through removal of impurities, concentrate, freezing and crystallizing, obtain highly purified eggplant Buddhist nun alcohol elaboration after the vacuum-drying, purity meets medicinal and the synthesis technique requirement greater than 96%, calculates by eggplant Buddhist nun alcohol meter, the direct yield of product is greater than 70%, and total recovery is greater than 85%.Details are as follows for its special process step:
A. system is expected with the eggplant Buddhist nun raw polyol of dissolution with solvents more than 10%, eggplant Buddhist nun raw polyol: solvent=1: 10 (W/V), be heated to 65 ℃, naturally cooling left standstill 12 hours, discard the lower black thick liquid, supernatant liquid is heated with stirring to 60 ℃, add sorbent material, eggplant Buddhist nun raw polyol: sorbent material=1: 2.3 (W/V) concentrates at 70 ℃ of normal pressures.Above-mentioned solvent is Jia Chun Yi Chun Yi Bingchun Yi Jing Shu Dingchun Bing Tong Lv Fang Si Lvhuatan Er Lvjiawan 1,2-Er Lvyiwan Shi Youmi Zheng Jiwan Huan Jiwan solvent oils etc.; Sorbent material be gac diatomite atlapulgite silica gel aluminum oxide ion exchange resin polymeric adsorbent etc.
B. solid-liquid chromatographic separation material that step a the is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, carry out gradient elution with polar solvent and weak polar solvent, wash-out is collected liquid and is carried out staging treating by TLC and HPLC detection.Above-mentioned polar solvent is a methyl alcohol: ethanol Virahol acetonitrile the trimethyl carbinol the linear gradient of acetone=10: 90～60: 40; Above-mentioned weak polar solvent is Lv Fang Si Lvhuatan Er Lvjiawan 1, the constant gradient of 2-Er Lvyiwan Shi Youmi Zheng Jiwan Huan Jiwan solvent oils etc.Above-mentioned pre-column is the steel column of 500mm diameter * 1000mm length; Above-mentioned separator column is the steel column of 300mm diameter * 2000mm length, in the post for silica gel bonded octadecyl filler or with silica gel zirconium white be matrix coat polystyrene polystyrene-divinylbenzene polyhutadiene polyacrylic ester polyacrylonitrile polyethylene oxide polyethers polyacrylamide the filler of agarose etc.
C. concentrate the collection concentrating under reduced pressure that will be rich in eggplant Buddhist nun alcohol section.Thickening temperature is controlled at 80 ± 5 ℃, under this temperature with≤-be concentrated into solvent under the 0.07MPa negative pressure not go out.
D. freezing and crystallizing will be collected the stage casing concentrated solution with 10 times dissolution with solvents, filter, and filtrate stirred crystallization under 5 ℃～-10 ℃ conditions is separated out eggplant Buddhist nun alcohol, filters, and obtain eggplant Buddhist nun alcohol filter cake, and mother liquor reclaims.Above-mentioned solvent be methyl alcohol ethanol sherwood oil acetone normal hexane.
E. drying obtains highly purified eggplant Buddhist nun alcohol elaboration with eggplant Buddhist nun alcohol filter cake drying under reduced pressure under 15--40 ℃ of temperature, 0.01MPa condition of negative pressure, and purity is greater than 96%, and directly yield is greater than 65%.
F. low collection liquid and the steps d gained that contains eggplant Buddhist nun alcohol section of step b gained reclaimed the mother liquor concentrating under reduced pressure, repeating step a～e continues to obtain highly purified eggplant Buddhist nun alcohol elaboration, and purity is greater than 96%, and total recovery is greater than 85%.
The method of above-mentioned purifying solanesol adopts industrial solid-liquid phase column chromatography separation technology, sorbent material in its pre-column and the separator column and filler pair have different absorption and distribution constant with the impurity of pure opposed polarity of eggplant Buddhist nun and different molecular weight, carry out selective elution with different solvents, in separator column, form the successive different spectral bands, meet the requirements of separating effect.
The method of above-mentioned purifying solanesol adopts large-scale pre-column and separator column, does not need saponification to handle, and only a post separation can obtain expected volume and specification of quality.Post is imitated and have been surpassed tens times of common low-pressure opening stratographic and reach high isolating effect, and has kept high pressure, changes advantage efficiently, fast and automatically.Single-column output reaches several kilograms to tens kilograms.The leacheate flow velocity can reach 1500ml/min, and separation cycle is short, and is simple to operate, manually expends and lacks, and production cost is low, and output is big, and the purity height meets industrial production requirement.
Appended drawings 1 is a process flow sheet of the present invention, and accompanying drawing 2 is the connection diagram of pre-column of the present invention and separator column.
Embodiment embodiment 1: adopt efficient industrial solid-liquid chromatographic column, pre-column (400mmI.D. * 1000mm), separator column (interior dress silica matrix coats the polyacrylonitrile filler for 300mmI.D. * 2000mm, stainless steel)
1. system is expected
From Raw material pail, take out 10% eggplant Buddhist nun raw polyol 60kg, add acetone, eggplant Buddhist nun raw polyol: acetone=1: 10.0 (W/V), normal pressure is heated with stirring to 60 ℃, naturally cooling left standstill 12 hours, bled off lower floor, and the upper strata is added sorbent material diatomite, eggplant Buddhist nun raw polyol: diatomite=1: 2.3 (W/V) concentrates at 70 ℃ of normal pressures.After later stage, the solvent speed of distillating slowed down to system material, begin 70 ℃, to be evaporated to material dried.
2. dress post
To concentrate the gained siccative with methyl alcohol disperse (material: solvent=1: 1 (W/V)), slowly add natural subsidence in the pre-column, be filled to height apart from capital 10cm, after sedimentation is real surface layer, capping.
3. wash-out
Pre-column is connected with separator column, use methyl alcohol: ethanol=0: 100～70: 30 (V/V), sherwood oil divide gradient elution, are eluted to major product concentration＜0.4mg/ml, control flow velocity 600ml/min in the collection process, and the post pressure-controlled is less than 30.0Mpa.Wash-out is collected liquid and is carried out staging treating by the HPLC detection, and major product concentration＜0.2mg/ml is divided into leading portion, major product concentration＞0.2mg/ml, and rear impurity peak area≤8% is divided into the stage casing, and rear impurity peak area＞8% is a back segment.
4. concentrate
Eggplant Buddhist nun alcohol is collected liquid just be divided into each section, respectively concentration by purity.Thickening temperature is controlled at 80 ± 5 ℃, under this temperature with≤-be concentrated into solvent under the 0.07MPa negative pressure not go out.
5. freezing and crystallizing
To collect the stage casing concentrated solution with 10 times of dissolve with ethanol, and filter, filtrate is stirred crystallization under-5 ℃～-10 ℃ conditions, and eggplant Buddhist nun alcohol was separated out in ageing in 8 hours, through centrifuging, obtains eggplant Buddhist nun alcohol filter cake.
6. dry
With eggplant Buddhist nun alcohol filter cake drying under reduced pressure 12 hours under 35 ℃ of temperature, 0.01MPa condition of negative pressure, obtain highly purified eggplant Buddhist nun alcohol elaboration, purity 96.7%, directly yield is greater than 74.1%.
Embodiment 2: the dress silica matrix coats the polyacrylamide filler in the separator column, from Raw material pail, take out 10% eggplant Buddhist nun raw polyol 60kg, add methyl alcohol, eggplant Buddhist nun raw polyol: methyl alcohol=1: 10.0 (W/V), normal pressure are heated with stirring to 60 ℃, and naturally cooling left standstill 12 hours, bleed off lower floor, the upper strata is added sorbent material silica gel, eggplant Buddhist nun raw polyol: silica gel=1: 2.3 (W/V) concentrates at 70 ℃ of normal pressures.After later stage, the solvent speed of distillating slowed down to system material, begin 70 ℃, to be evaporated to material dried.Other technological process is fully identical with embodiment 1, gained eggplant Buddhist nun alcohol elaboration 96.2%, directly yield 75%.
Embodiment 3: take out 10% eggplant Buddhist nun raw polyol 60kg from Raw material pail, eggplant Buddhist nun raw polyol: methyl alcohol=1: 10.0 (W/V) normal pressure is heated with stirring to 60 ℃, naturally cooling left standstill 12 hours, bleed off lower floor, the upper strata is added the adsorbent activity carclazyte, eggplant Buddhist nun raw polyol: atlapulgite=1: 2.0 (W/V) concentrates at 70 ℃ of normal pressures.After later stage, the solvent speed of distillating slowed down to system material, begin 70 ℃, to be evaporated to material dried.Its technological process is fully identical with embodiment 1, gained eggplant Buddhist nun alcohol elaboration 96.9%, directly yield 71.1%.
Claims (12)
1. the present invention adopts purity to make raw material greater than 10% solanesol extract, use dissolution with solvents, standing demix, the upper strata adds sorbent material and mixes concentrated absorption, adopt industrial solid-liquid phase column chromatography separation technology, use polarity, weak polar solvent or mixed solvent wash-out, segmentation is removed and the eggplant Buddhist nun alcohol impurity that polarity is different or molecular weight difference is bigger, to contain eggplant Buddhist nun alcohol section through removal of impurities, concentrate, freezing and crystallizing, obtain highly purified eggplant Buddhist nun alcohol elaboration after the vacuum-drying, purity meets medicinal and the synthesis technique requirement greater than 96%, calculates by eggplant Buddhist nun alcohol meter, the direct yield of product is greater than 70%, and total recovery is greater than 85%.Details are as follows for its processing step:
A. system is expected with the eggplant Buddhist nun raw polyol of dissolution with solvents more than 10%, eggplant Buddhist nun raw polyol: solvent=1: 10 (W/V), be heated to 65 ℃, naturally cooling left standstill 12 hours, discard the lower black thick liquid, supernatant liquid is heated with stirring to 60 ℃, add sorbent material, eggplant Buddhist nun raw polyol: sorbent material=1: 2.3 (W/V) concentrates at 70 ℃ of normal pressures.
B. solid-liquid chromatographic separation material that step a the is made pre-column of packing into, the free setting compacting.Pre-column is connected with separator column, carry out gradient elution with polar solvent and weak polar solvent, wash-out is collected liquid and is carried out staging treating by TLC and HPLC detection.Above-mentioned pre-column is the steel column of 400mm diameter * 1000mm length; Above-mentioned separator column is the steel column of 300mm diameter * 2000mm length.
C. concentrate the collection concentrating under reduced pressure that will be rich in eggplant Buddhist nun alcohol section.Thickening temperature is controlled at and is concentrated into solvent under 80 ± 5 ℃, 0.07MPa negative pressure and does not go out.
D. freezing and crystallizing will be collected the stage casing concentrated solution with 10 times dissolution with solvents, filter, and filtrate stirred crystallization under 5 ℃～-10 ℃ conditions is separated out eggplant Buddhist nun alcohol, filters, and obtain eggplant Buddhist nun alcohol filter cake, and mother liquor reclaims.
E. drying obtains highly purified eggplant Buddhist nun alcohol elaboration with eggplant Buddhist nun alcohol filter cake drying under reduced pressure under 15-40 ℃ of temperature, 0.01MPa condition of negative pressure, and purity is greater than 96%, and directly yield is greater than 70%.
Low collection liquid and the steps d gained that contains eggplant Buddhist nun alcohol section of step b gained reclaimed the mother liquor concentrating under reduced pressure, and repeating step a～e continues to obtain highly purified eggplant Buddhist nun alcohol elaboration, and purity is greater than 96%, and total recovery is greater than 85%.
Claim 1 indication greater than 10% solanesol extract raw material be by extract in tobacco leaf, leaf of potato, the animal viscera, concentrate, products therefrom after the crystallization.
3. the described solvent of the step a of claim 1 is Jia Chun Yi Chun Yi Bingchun Yi Jing Shu Dingchun Bing Tong Lv Fang Si Lvhuatan Er Lvjiawan 1,2-Er Lvyiwan Shi Youmi Zheng Jiwan Huan Jiwan solvent oils etc.
The described sorbent material of the step a of claim 1 be gac diatomite atlapulgite silica gel aluminum oxide ion exchange resin polymeric adsorbent etc.
5. the described polar solvent of the step b of claim 1 is a methyl alcohol: ethanol Virahol acetonitrile the trimethyl carbinol the linear gradient of acetone=10: 90～60: 40.
6. the described weak polar solvent of the step b of claim 1 is Lv Fang Si Lvhuatan Er Lvjiawan 1,2-Er Lvyiwan Shi Youmi Zheng Jiwan Huan Jiwan solvent oils etc.
7. the described chromatographic process of the step b of claim 1 is that pre-column adds separator column, and the material to be separated and the pre-column of packing into after sorbent material mixes, raw material do not need saponification to handle.
In the described separator column of the step b of claim 1 filler be silica gel bonded octadecyl filler or with silica gel zirconium white be matrix coat polystyrene polystyrene-divinylbenzene polyhutadiene polyacrylic ester polyacrylonitrile polyethylene oxide polyethers the filler of agarose etc.
9. described pre-column of the step b of claim 1 and separator column material are carbon steel, stainless steel, glass, plastics, steel and plastic composite material etc.
10. the described Tc of the steps d of claim 1 is at 5 ℃～-10 ℃; Stirring velocity is 5 rev/mins～40 rev/mins.
11. the described solvent of the steps d of claim 1 be methyl alcohol ethanol sherwood oil acetone normal hexane.
12. the described drying conditions of the step e of claim 1 is a drying under reduced pressure under 15-40 ℃ of temperature, 0.01MPa condition of negative pressure.
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|---|---|---|---|
| CN 200510063053 CN1686988A (en) | 2005-04-05 | 2005-04-05 | Method for preparing high pure solanesol |
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| CN 200510063053 CN1686988A (en) | 2005-04-05 | 2005-04-05 | Method for preparing high pure solanesol |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100425530C (en) * | 2006-12-28 | 2008-10-15 | 广州有色金属研究院 | Method for recovering tellurium from bismuth telluride base semiconductor refrigeration material |
| CN105124740A (en) * | 2015-08-28 | 2015-12-09 | 湖北中烟工业有限责任公司 | Method for freezing and concentrating paper-making reconstituted tobacco refined liquid |
| TWI641585B (en) * | 2017-04-17 | 2018-11-21 | 義守大學 | Method of purifying solanesol |
| CN110465114A (en) * | 2019-08-23 | 2019-11-19 | 内蒙古金达威药业有限公司 | A kind of Simulation moving bed continuous chromatography chromatographic system and its application and the method for purifying Co-Q10 |
| CN111233630A (en) * | 2019-12-31 | 2020-06-05 | 常德市正阳生物科技股份有限公司 | Separation method of solanesol-containing eluent |
| CN111533643A (en) * | 2019-12-31 | 2020-08-14 | 常德市正阳生物科技股份有限公司 | Method for separating concentrated paste of tobacco leaf extracting solution |
| CN113307723A (en) * | 2021-05-15 | 2021-08-27 | 昆明理工大学 | Method for purifying solanesol by adopting temperature-controlled crystallization |
| CN114249632A (en) * | 2021-12-20 | 2022-03-29 | 贵州省烟草公司遵义市公司 | Novel process for purifying solanesol based on chemically modified diatomite |
-
2005
- 2005-04-05 CN CN 200510063053 patent/CN1686988A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100425530C (en) * | 2006-12-28 | 2008-10-15 | 广州有色金属研究院 | Method for recovering tellurium from bismuth telluride base semiconductor refrigeration material |
| CN105124740A (en) * | 2015-08-28 | 2015-12-09 | 湖北中烟工业有限责任公司 | Method for freezing and concentrating paper-making reconstituted tobacco refined liquid |
| TWI641585B (en) * | 2017-04-17 | 2018-11-21 | 義守大學 | Method of purifying solanesol |
| CN110465114A (en) * | 2019-08-23 | 2019-11-19 | 内蒙古金达威药业有限公司 | A kind of Simulation moving bed continuous chromatography chromatographic system and its application and the method for purifying Co-Q10 |
| CN111233630A (en) * | 2019-12-31 | 2020-06-05 | 常德市正阳生物科技股份有限公司 | Separation method of solanesol-containing eluent |
| CN111533643A (en) * | 2019-12-31 | 2020-08-14 | 常德市正阳生物科技股份有限公司 | Method for separating concentrated paste of tobacco leaf extracting solution |
| CN113307723A (en) * | 2021-05-15 | 2021-08-27 | 昆明理工大学 | Method for purifying solanesol by adopting temperature-controlled crystallization |
| CN113307723B (en) * | 2021-05-15 | 2024-05-28 | 昆明理工大学 | Method for purifying solanesol by adopting temperature-controlled crystallization |
| CN114249632A (en) * | 2021-12-20 | 2022-03-29 | 贵州省烟草公司遵义市公司 | Novel process for purifying solanesol based on chemically modified diatomite |
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Open date: 20051026 |