CN100384797C - Method for extracting high-purity solanesol - Google Patents
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Abstract
The present invention discloses a method for extracting high-purity solanesol. With a high-effective separation purification method combined by supercritical CO2 fluid extraction and column chromatography, waste low-grade tobacco leaves are used as a raw material for extracting high-purity solanesol. The present invention solves the common problems of low purity, low efficiency, high cost, great environmental pollution, etc. in high-purity solanesol extraction processes. With an entrainer reinforcement technique, preprocessed tobacco leaves are processed by supercritical CO2 fluid one-stage extraction and two-stage separation simultaneously, so supercritical CO2 fluid extractant is selectively separated in two different extraction stills, and the technique realizes the primary separation of rich solanesol and the extractant. Solanesol coarse paste is further purified by the column chromatography after being saponified in an NaOH alcoholic solution and is decompressed and concentrated into solanesol rich eluent, a concentrated solution of the eluent is processed by freezing crystallization and vacuum drying, and the purity of the solanesol is more than 95%.
Description
Technical field
The present invention relates to a kind of method of extraction of high purity solanesol alcohol.
Background technology
Eggplant Buddhist nun alcohol is one of effective constituent in the tobacco leaf.Extractive technique mainly comprises: (1) is raw material with the tobacco leaf, adopting normal hexane and No. 6 solvent oils is extraction agent, its eggplant Buddhist nun alcohol purity is about 18%, and extraction times is many, raw material and solvent ratio are 1: 4～1: 10, the extraction agent consumption is big, solvent loss is big, and recovery cost height, production process are loaded down with trivial details time-consuming.(2) be raw material with 10% solanesol extract, adopt the pre-column treatment process of connecting with separator column, the purity of its eggplant Buddhist nun alcohol reaches about 96%.Use the pre-column and the separator column of cascaded structure to carry out separation and purification in this technology, its device relative volume is bigger, is difficult for realizing in industrial production.(3) with 70% eggplant Buddhist nun raw polyol, adopt high performance liquid phase or silica gel medium pressure packed column to carry out purifying, its purity can reach 98.5%, but uses a large amount of solvents first, and strict control condition is wanted in operation, and the production time is long, and weighting material can't reclaim, and cost is too high.Therefore, the novel method of further studying the extraction and purification of high-purity solanesol is necessary.
Supercritical extraction technique is a kind of new separation technology.Compare with the conventional organic solvents extraction process, because under the supercritical state, supercutical fluid has the character of gas and liquid concurrently, has unique advantage aspect the extraction of natural constituent.The patent of publication number CN1294111, the production technique of extraction of employing one-level and flash trapping stage, extracting and separating eggplant Buddhist nun alkoxide component from tobacco, the extraction time is 2～4 hours, its percentage extraction is about 90%.In this invention the supercritical extraction time longer, the product that obtains is still for crude product.And the patent of publication number CN1676502 is a raw material with the thick cream of eggplant Buddhist nun alcohol, adopts supercritical CO
2Abstraction technique carries out the segmentation removal of impurities, and its purity reaches 95%.This invention belongs to the technology that is further purified of eggplant Buddhist nun alcohol crude product, because many defectives of organic solvent extractionprocess can't fundamentally be avoided still from the conventional organic solvents abstraction technique in the eggplant Buddhist nun of overwhelming majority alcohol crude product source therefore at present.
Summary of the invention
The deficiency that the prior art percentage extraction is low in order to overcome, the extraction time is long, the invention provides a kind of directly is raw material with the tobacco leaf, adopts supercritical CO
2The high efficiency separation and the purification technique of fluid extraction and column chromatography associating, the method for extraction of high purity solanesol alcohol.
The technical solution adopted for the present invention to solve the technical problems is: a kind of method of extraction of high purity solanesol alcohol comprises the steps:
1) inferior tobacco is crushed to 40～60 orders, after being soaked in water 5～10 hours, adopts whizzer to remove leaching liquid, the tobacco leaf of handling is positioned over 50～70 ℃ of dryings down;
2) will mix with entrainment agent through the tobacco leaf that step 1) is handled and put into extraction kettle, perhaps will directly put into extraction kettle through the tobacco leaf that step 1) is handled, by pump input entrainment agent, tobacco leaf soaks into 30～40min in extraction kettle, the entrainment agent consumption is the 120ml/100g tobacco leaf, and temperature is 40 ℃ in the extraction kettle;
3) when the temperature of separation reactor I and separation reactor I I reaches 40 ℃ of set(ting)values, open intake valve and feed CO
2, CO
2Flow is 0.2～0.4L/min, and the extracting pressure of extraction kettle adjusted to 25～30MPa, the pressure of separation reactor I is 8～10MPa, the pressure of separation reactor I I is 6～8MPa, after 30～50min extraction, collect the extract of separation reactor I and separation reactor I I respectively, adopt the entrainment agent in the Rotary Evaporators recovery extract;
4) will handle the extract crude product that obtains through step 3), add the 30ml petroleum ether dissolution by every 10g, and the ethanolic soln 60ml that adds 1.2mol/LNaOH carries out saponification, saponification temperature is 50～70 ℃, saponification pressure is 90～110MPa, and saponification time is 1～2 hour;
5) choosing specification is that 100～200 purpose silica gel activate under 110 ℃, be 15: 1 according to silica gel with the raw material that needs purifying then, employing wet method dress post method is packed in the chromatography column, mixed solvent with ethyl acetate and sherwood oil carries out wash-out, flow velocity is 4～6ml/min, the ratio of sherwood oil and ethyl acetate is 3: 1～5: 1, and elution process adopts TLC to follow the tracks of and detects, and the Fractional Collections elutriant;
6) adopt Rotary Evaporators to carry out concentrating under reduced pressure to the elutriant of handling through step 5) that is enriched with eggplant Buddhist nun alcohol, reclaim eluent simultaneously, temperature is 40～50 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.07～0.09MPa;
7) will place 0～-5 ℃ through the concentrated solution that step 6) is handled under through behind the freezing and crystallizing fully, under 25 ℃, vacuum-drying under the 0.02MPa.
Described entrainment agent is ethyl acetate, sherwood oil or acetone.
The invention has the beneficial effects as follows: owing to adopt the entrainment agent intensifying technology, improved the percentage extraction of supercritical extraction eggplant Buddhist nun alcohol, and the extraction time shortens to 1.5 hours by 2～4 hours of prior art; Supercritical CO
2Extract separates through secondary, realizes that the highly selective of extraction process is separated, and good separating effect, has reduced the difficulty of purge process; In the process of supercritical extraction eggplant Buddhist nun alcohol, add entrainment agent, make the intermolecular effect of supercutical fluid and eggplant Buddhist nun alcohol obviously strengthen, improved the extraction efficiency of eggplant Buddhist nun alcohol.And the secondary separating still of employing polyphone, by setting different separating still pressure respectively, regulate and solubleness and the resolution of control solute in separating still, make the supercritical extract selectivity resolve, realize the first separation of extract, reduce the difficulty that the later stage purifying obtains high-purity solanesol.
The present invention is further described below in conjunction with drawings and Examples.
Description of drawings
Accompanying drawing is the method flow diagram of extraction of high purity solanesol alcohol of the present invention.
Embodiment
Embodiment 1: weighing 100g inferior tobacco, tobacco leaf powder is broken to 40 orders, and after being soaked in water 5 hours, adopt whizzer to remove leaching liquid, the tobacco leaf of handling is positioned over 50 ℃ of dryings down.Its leaching liquid is collected the extraction that remains for nicotine.
The tobacco leaf of handling is mixed with entrainment agent 120ml, in the extraction kettle of the 1L that packs into, soaked into 30 minutes.Temperature is 40 ℃ in the setting extraction kettle, and the temperature of separation reactor I and separation reactor I I is identical with the temperature of extraction kettle, when temperature all reaches set(ting)value, opens intake valve and feeds CO
2, CO
2Flow is 0.2L/min, and reconciles the extracting pressure 25MPa of extraction kettle, and the pressure of separation reactor I and separation reactor I I is respectively 8MPa, 6MPa, and per 30 minutes clock times are carried out in extraction, collect the extract in each separating still respectively, and whole extraction process is 1.5 hours.Adopt the entrainment agent in the Rotary Evaporators recovery extract.
Take by weighing the crude product 10g that the supercritical extraction of separation reactor I and separation reactor I I obtains respectively, add the 30ml petroleum ether dissolution, and the ethanolic soln 60ml that adds 1.2mol/L NaOH carrying out saponification, is 50 ℃ in temperature, and pressure is 110MPa, and saponification time is 2 hours.And saponification liquor is added the equal-volume sherwood oil extract 2 times, the extraction liquid of inspissated oil ether respectively.
Under 110 ℃, silica gel is through overactivation, and the specification of silica gel is 100 orders.Employing wet method dress post is packed silica gel in the chromatography column, silica gel is 15: 1 with the raw material ratio that needs purifying, crude product concentrated solution to separation reactor I carries out the one-level column chromatography earlier, the elutriant of its enriched solanesol is collected and concentrating under reduced pressure, reclaim eluent simultaneously, temperature is 40 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.07MPa; With separate II in spissated petroleum ether extraction liquid merge, adopt column chromatography device to carry out purifying jointly, be 1: 3 mixed solvent with sherwood oil and ethyl acetate ratio, under normal pressure, it is carried out wash-out, flow velocity is 6ml/min.Fractional Collections carries out the eluent of chromatography, and the eluent of enriched solanesol is collected and concentrated, and reclaims eluent simultaneously, and temperature is 40 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.09MPa; And concentrated solution is positioned over carries out freezing and crystallizing under 0 ℃, and be 25 ℃ in temperature, carry out vacuum-drying under the 0.02MPa pressure.
Detect through HPLC, adopt supercritical CO
2The high efficiency separation and the purification technique of fluid extraction and column chromatography associating, the purity of extracting eggplant Buddhist nun alcohol is 95%.
Embodiment 2: weighing 100g inferior tobacco, tobacco leaf powder is broken to 50 orders, and after being soaked in water 8 hours, adopt whizzer to remove leaching liquid, the tobacco leaf of handling is positioned over 60 ℃ of dryings down.Its leaching liquid is collected the extraction that remains for nicotine.
The tobacco leaf of handling is mixed with entrainment agent 120ml, in the extraction kettle of the 1L that packs into, soaked into 35 minutes.Temperature is 40 ℃ in the setting extraction kettle, and the temperature of separation reactor I and separation reactor I I is identical with the temperature of extraction kettle, when temperature all reaches set(ting)value, opens intake valve and feeds CO
2, CO
2Flow is 0.33L/min, and reconciles the extracting pressure 28mPa of extraction kettle, and the pressure of separation reactor I and separation reactor I I is respectively 9MPa, 7MPa, and per 40 minutes clock times are carried out in extraction, collect the extract in each separating still respectively, and whole extraction process is 1.5 hours.Adopt the entrainment agent in the Rotary Evaporators recovery extract.
Take by weighing the crude product 10g that the supercritical extraction of separation reactor I and separation reactor I I obtains respectively, add the 30ml petroleum ether dissolution, and the ethanolic soln 60ml that adds 1.2mol/L NaOH carrying out saponification, is 60 ℃ in temperature, and pressure is 100MPa, and saponification time is 1.5 hours.And saponification liquor is added the equal-volume sherwood oil extract 2 times, the extraction liquid of inspissated oil ether respectively.
Under 110 ℃, silica gel is through overactivation, and the specification of silica gel is 150 orders.Employing wet method dress post is packed silica gel in the chromatography column, silica gel is 15: 1 with the raw material ratio that needs purifying, crude product concentrated solution to separation reactor I carries out the one-level column chromatography earlier, the elutriant of its enriched solanesol is collected and concentrating under reduced pressure, reclaim eluent simultaneously, temperature is 45 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.07～0.08MPa; With separate II in spissated petroleum ether extraction liquid merge, adopt column chromatography device to carry out purifying jointly, be 1: 4 mixed solvent with sherwood oil and ethyl acetate ratio, under normal pressure, it is carried out wash-out, flow velocity is 5ml/min.Fractional Collections carries out the eluent of chromatography, and the eluent of enriched solanesol is collected and concentrated, and reclaims eluent simultaneously, and temperature is 45 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.08MPa; And concentrated solution is positioned under-5 ℃ carries out freezing and crystallizing, and be 25 ℃ in temperature, carry out vacuum-drying under the 0.02MPa pressure.
Detect through HPLC, adopt supercritical CO
2The high efficiency separation and the purification technique of fluid extraction and column chromatography associating, the purity of extracting eggplant Buddhist nun alcohol is 96%.
Embodiment 3: weighing 100g inferior tobacco, tobacco leaf powder is broken to 60 orders, and after being soaked in water 10 hours, adopt whizzer to remove leaching liquid, the tobacco leaf of handling is positioned over 70 ℃ of dryings down.Its leaching liquid is collected the extraction that remains for nicotine.
The tobacco leaf of handling is mixed with entrainment agent 120ml, in the extraction kettle of the 1L that packs into, soaked into 40 minutes.Temperature is 40 ℃ in the setting extraction kettle, and the temperature of separation reactor I and separation reactor I I is identical with the temperature of extraction kettle, when temperature all reaches set(ting)value, opens intake valve and feeds CO
2, CO
2Flow is 0.4L/min, and reconciles the extracting pressure 30mPa of extraction kettle, and the pressure of separation reactor I and separation reactor I I is respectively 10MPa, 8MPa, and per 50 minutes clock times are carried out in extraction, collect the extract in each separating still respectively, and whole extraction process is 1.5 hours.Adopt the entrainment agent in the Rotary Evaporators recovery extract.
Take by weighing the crude product 10g that the supercritical extraction of separation reactor I and separation reactor I I obtains respectively, add the 30ml petroleum ether dissolution, and the ethanolic soln 60ml that adds 1.2mol/LNaOH carrying out saponification, is 70 ℃ in temperature, and pressure is 90MPa, and saponification time is 1 hour.And saponification liquor is added the equal-volume sherwood oil extract 2 times, the extraction liquid of inspissated oil ether respectively.
Under 110 ℃, silica gel is through overactivation, and the specification of silica gel is 200 orders.Employing wet method dress post is packed silica gel in the chromatography column, silica gel is 15: 1 with the raw material ratio that needs purifying, crude product concentrated solution to separation reactor I carries out the one-level column chromatography earlier, the elutriant of its enriched solanesol is collected and concentrating under reduced pressure, reclaim eluent simultaneously, temperature is 50 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.09MPa; With separate II in spissated petroleum ether extraction liquid merge, adopt column chromatography device to carry out purifying jointly, be 1: 5 mixed solvent with sherwood oil and ethyl acetate ratio, under normal pressure, it is carried out wash-out, flow velocity is 4ml/min.Fractional Collections carries out the eluent of chromatography, and the eluent of enriched solanesol is collected and concentrated, and reclaims eluent simultaneously, and temperature is 50 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.07MPa; And concentrated solution is positioned under-3 ℃ carries out freezing and crystallizing, and be 25 ℃ in temperature, carry out vacuum-drying under the 0.02MPa pressure.
Detect through HPLC, adopt supercritical CO
2The high efficiency separation and the purification technique of fluid extraction and column chromatography associating, the purity of extracting eggplant Buddhist nun alcohol is 95.5%.
Claims (2)
1. the method for an extraction of high purity solanesol alcohol comprises the steps:
1) inferior tobacco is crushed to 40～60 orders, after being soaked in water 5～10 hours, adopts whizzer to remove leaching liquid, the tobacco leaf of handling is positioned over 50～70 ℃ of dryings down;
2) will mix with entrainment agent through the tobacco leaf that step 1) is handled and put into extraction kettle, perhaps will directly put into extraction kettle through the tobacco leaf that step 1) is handled, by pump input entrainment agent, tobacco leaf soaks into 30～40min in extraction kettle, the entrainment agent consumption is the 120ml/100g tobacco leaf, and temperature is 40 ℃ in the extraction kettle;
3) when the temperature of separation reactor I and separation reactor I I reaches 40 ℃ of set(ting)values, open intake valve and feed CO
2, CO
2Flow is 0.2～0.4L/min, and the extracting pressure of extraction kettle adjusted to 25～30MPa, the pressure of separation reactor I is 8～10MPa, the pressure of separation reactor I I is 6～8MPa, after 30～50min extraction, collect the extract of separation reactor I and separation reactor I I respectively, adopt the entrainment agent in the Rotary Evaporators recovery extract;
4) will handle the extract crude product that obtains through step 3), add the 30ml petroleum ether dissolution by every 10g, and the ethanolic soln 60ml that adds 1.2mol/LNaOH carries out saponification, saponification temperature is 50～70 ℃, saponification pressure is 90～110MPa, and saponification time is 1～2 hour;
5) choosing specification is that 100～200 purpose silica gel activate under 110 ℃, be 15: 1 according to silica gel with the raw material that needs purifying then, employing wet method dress post method is packed in the chromatography column, mixed solvent with ethyl acetate and sherwood oil carries out wash-out, flow velocity is 4～6ml/min, the ratio of sherwood oil and ethyl acetate is 3: 1～5: 1, and elution process adopts TLC to follow the tracks of and detects, and the Fractional Collections elutriant;
6) adopt Rotary Evaporators to carry out concentrating under reduced pressure to the elutriant of handling through step 5) that is enriched with eggplant Buddhist nun alcohol, reclaim eluent simultaneously, temperature is 40～50 ℃ during concentrating under reduced pressure, and vacuum tightness is 0.07～0.09MPa;
7) will place 0～-5 ℃ through the concentrated solution that step 6) is handled under through behind the freezing and crystallizing fully, under 25 ℃, vacuum-drying under the 0.02MPa.
2. the method for extraction of high purity solanesol alcohol according to claim 1 is characterized in that: described entrainment agent is ethyl acetate, sherwood oil or acetone.
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| TWI641585B (en) * | 2017-04-17 | 2018-11-21 | 義守大學 | Method of purifying solanesol |
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| CN101857527B (en) * | 2010-06-10 | 2013-02-27 | 成都市翻鑫家科技有限公司 | Method for extracting Solanesol from waste and poor tobacco leave extract |
| CN103436363B (en) * | 2013-09-03 | 2014-12-10 | 华宝食用香精香料（上海）有限公司 | Preparation method of aroma substance in Zimbabwe tobacco extractive as well as products and application of aroma substance |
| CN104450186B (en) * | 2014-10-29 | 2017-04-19 | 山东中烟工业有限责任公司 | Method for preparing tobacco herbal fragrant substance for cigarette solution of electronic cigarette |
| CN105646150B (en) * | 2016-02-03 | 2018-08-17 | 河西学院 | A method of the extraction of high purity solanesol alcohol from tobacco leaf |
| CN108794299A (en) * | 2017-05-04 | 2018-11-13 | 义守大学 | The method of purified solanesol |
| CN108046990B (en) * | 2018-01-04 | 2021-01-15 | 中国烟草总公司广东省公司 | Method for extracting solanesol |
| CN110903168B (en) * | 2018-09-18 | 2024-01-26 | 河南元萃生物科技有限公司 | Method for subcritical extraction of solanesol in waste tobacco leaves |
| CN110818665A (en) * | 2019-11-07 | 2020-02-21 | 河南中烟工业有限责任公司 | Preparation method of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one |
| CN114591142B (en) * | 2022-03-17 | 2024-01-05 | 禹州市合同泰药业有限公司 | Method for extracting solanesol from waste and inferior tobacco leaves |
| CN115784842A (en) * | 2022-10-26 | 2023-03-14 | 贵州汇腾科技有限公司 | Preparation method and application of high-value component solanesol in waste and inferior tobacco |
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| TWI641585B (en) * | 2017-04-17 | 2018-11-21 | 義守大學 | Method of purifying solanesol |
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