CN104450204A - Cleaner production process for synchronously extracting gossypol and fatty acid from cottonseed oil soap - Google Patents
Cleaner production process for synchronously extracting gossypol and fatty acid from cottonseed oil soap Download PDFInfo
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- CN104450204A CN104450204A CN201410834721.2A CN201410834721A CN104450204A CN 104450204 A CN104450204 A CN 104450204A CN 201410834721 A CN201410834721 A CN 201410834721A CN 104450204 A CN104450204 A CN 104450204A
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- gossypol
- cotton oil
- distillation residues
- oil distillation
- extract
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B13/00—Recovery of fats, fatty oils or fatty acids from waste materials
- C11B13/02—Recovery of fats, fatty oils or fatty acids from waste materials from soap stock
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/74—Recovery of fats, fatty oils, fatty acids or other fatty substances, e.g. lanolin or waxes
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
Abstract
The invention belongs to the technical field of processing of oil crops, and specifically relates to a cleaner production process of synchronously gossypol and fatty acid from cottonseed oil soap. The clean production process for processing and utilizing cottonseed oil soap is simple, convenient, efficient, low in cost, high in additional value, applicable to industrial mass extraction of gossypol and fatty acid of cotton seed oil dregs from cottonseed oil soap. The process, by being compared with the prior art, has the advantages that cottonseed oil soap is used as the raw material for extracting gossypol, and high-quality gossypol and fatty acid of cotton seed oil dregs can be obtained on the premise that no wastewater is caused, so that the green and clean processing and utilization of cottonseed oil soap are achieved, one of the major pollution sources in cottonseed oil processing industry is removed, and meanwhile, the additional value of cottonseed oil soap is greatly increased, and the process has a good application prospect in the cottonseed processing field.
Description
Technical field
The invention belongs to the processing technique field of oil crops, belong to the process for cleanly preparing simultaneously extracting gossypol and lipid acid in a kind of cotton oil distillation residues specifically.
Background technology
Cottonseed is the by product of Cotton Production, one of large vegetable oil material resource of China.Cottonseed grease wherein containing high-quality and cottonseed protein, and the medicinal raw material gossypol of preciousness.Take cottonseed as raw material, can the multiple product such as processing Oleum Gossypii semen, cottonseed protein, gossypol.But because gossypol has the toxicity that can cause male sterility, thus Oleum Gossypii semen is before edible, must carry out alkali refining, is removed by wherein contained gossypol, otherwise can cause poisoning.
Existing cottonseed processing technique carries out leaching extracting with No. 6 solvents to cottonseed, obtain crude cotton seed oil and cotton dregs, and then alkali refining (depickling), decolouring, deodorization process are carried out to crude cotton seed oil, crude cotton seed oil is changed into refined cottonseed oil that can be edible, alkali refining step is wherein the main step mule that gossypol removes, in the soap stock obtained after contained gossypol major part all concentrates on alkali refining in crude cotton seed oil.
Existing with cotton oil distillation residues is, and raw material prepares the multiplex vitriol oil in the technique of lipid acid carries out direct acidifying, hydrolysis to soap stock, gossypol contained by making in cotton oil distillation residues is substantially all oxidized to be destroyed, thus a large amount of waste water and the very dark plant asphalt of color and luster is formed, form large source of pollution of vegetables oil processing industry, so far there are no the relevant report taking cotton oil distillation residues as raw material separation and Extraction gossypol.
Summary of the invention
A kind of process for cleanly preparing simultaneously extracting gossypol and lipid acid from cotton oil distillation residues of invention, relates to a kind of eco-friendly, carries out in solvent-extracted mode, relatively inexpensive, high efficiency, cotton oil distillation residues processing and utilization novel process.Comparatively unique is, it relates to a kind of improved technique, this technique is with cotton oil distillation residues, instead of crude cotton seed oil, cotton dregs or other cottonseed processing products, is raw material, adopt phosphoric acid, instead of the vitriol oil, neutralization, acidifying cotton oil distillation residues, extract lipid acid contained in gossypol and cotton oil distillation residues with solvent extration, the gossypol of co-producing high-purity and lipid acid, and no longer produce soap stock acidified waste water.Operate according to this patent, compared with traditional method before this, can under the prerequisite not reducing cotton oil fatty acid quality, the products such as the acquisition gossypol of high-quality high yield, production cost is significantly reduced, meanwhile, eliminate acidification oil factory effluent and source of pollution such as decolouring roach etc. from source, this improvement is vital for the comprehensive utilization of this large oil crops resource with a very important position in national economy of cottonseed.
One of most important object of the present invention, will realize the cleaning of separation and Extraction lipid acid in cotton oil distillation residues exactly, environmental friendlinessization produces, solve the problem of environmental pollution of Oleum Gossypii semen processing industry from source.
As one, along the result be with, another object of the present invention is the medicinal raw material gossypol that will obtain high purity high-quality, reduces production cost, guarantees quality product.
Specifically; first; we find; the gossypol wrapped in cotton oil distillation residues, owing to receiving the embedding of the composition such as phosphatide, free fatty acids of simultaneous removing and oxygen barrier protection, although salify; as long as but process in time; be not subject to serious structure deteriorate, with non-oxidizing acid by cotton oil distillation residues acidifying after, still can revert to gossypol.Establish thus and used phosphoric acid cotton oil distillation residues, then the basis of therefrom separation and Extraction gossypol.
Secondly, we find, adopting suitable is extraction agent with the immiscible organic solvent of water, and the free gossypol that can effectively will generate after cotton oil distillation residues hydrolysis, in company with free fatty acids together, is thoroughly separated with the aqueous solution and other water soluble components.The gossypol acetate of high purity more than 98% is obtained after add acetic acid in extracting solution.Establish the basis of gossypol separation purifying technique of extraction agent extracting, acetic acid precipitation thus.
We find, gossypol and cotton oil lipid acid extract by the technique be made up of the following step and obtains:
1) with phosphoric acid, cotton oil distillation residues is neutralized, by the pH regulator of cotton oil distillation residues to pH≤7.0;
2) adding extraction agent, under the prerequisite existed there being extraction agent, cotton oil distillation residues being thoroughly hydrolyzed, then carry out liquid-liquid separation, obtain organic phase and aqueous phase;
3) extract aqueous phase with extraction agent, gained extraction liquid and organic phase merge, and form extracting solution.The pH value alkali of raffinate is adjusted to neutrality, then concentrated, recovery extraction agent, reclaim the extraction agent obtained and recycle, enriched product is sold as liquid fertilizer;
4) in extracting solution, add Glacial acetic acid, contained by making wherein, gossypol is with the form Precipitation of gossypol acetate.Then filter, wash, dry, obtain gossypol acetate;
5) gained filtrate and washings merge, and go rectifier unit process, are separated and are extracted agent, acetic acid and cotton oil lipid acid.The extraction agent that recovery obtains and acetic acid recycle;
6) cotton oil lipid acid can sell, and also can obtain palmitinic acid, oleic acid and plant asphalt through negative pressure rectifying, sell as product.
Extraction agent wherein can be one or more mixtures formed in benzene,toluene,xylene, Virahol, propyl carbinol, the trimethyl carbinol, tertiary amyl alcohol, ether, ethyl acetate, trichloromethane, butanone or other any organic solvents not miscible with water.The addition of extraction agent is 0.1 ~ 10 times of cotton oil distillation residues weight.Hydrolysis can be made catalyzer with acid and carry out, and also can carry out with Phospholipid hydrolase or lipase as catalyst, also can both combinations carry out.When making catalyzer of acid and being hydrolyzed, to be hydrolyzed in pH≤2,80 ~ 180 DEG C, preferably 100 ~ 148 DEG C, 0.1 ~ 1.0MPa, condition under carry out 0.5 ~ 10 hour.When being hydrolyzed with Phospholipid hydrolase or lipase as catalyst, being hydrolyzed and carrying out 0.5 ~ 10 hour under the optimal pH of enzyme used, optimum temperuture, normal pressure.Liquid-liquid separation can be settlement separate or centrifugation, carries out at normal pressure 0-50 DEG C.Extraction at 0 ~ 78 DEG C, preferably 4 ~ 38 DEG C, 0.01 ~ 1.0MPa, condition under carry out 1-10 time, needed for each extraction, the amount of extraction agent is 80% ~ 120% (v/v) of aqueous phase amount, and extraction time is 0.15 ~ 12hr time
-1.The alkali regulating raffinate pH used can be ammoniacal liquor, also can be the material that salt of wormwood, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium hydroxide, calcium carbonate, unslaked lime, white lime or any one can be adjusted to pH=6.5 ~ 7.0.Glacial acetic acid at room temperature adds, and its addition is 1 ~ 3 times of contained gossypol amount in extracting solution.Filter, washing at room temperature carry out, dry at 30 ~ 180 DEG C, preferably 50 ~ 105 DEG C, 0.01 ~ 1.0MPa, condition under carry out.
After the whole optimization of all important parameters mentioned in the present invention, the yield of gossypol can reach 3-5%, and the purity of gained gossypol product can reach more than 98%, and the yield of fatty acid product and purity are all unaffected.
Embodiment
Example below will illustrate working method of the present invention, but can not as limitation of the invention.
Example one
By 1000g water content be 50% cotton oil distillation residues concentration be 85% phosphoric acid adjust pH to 6.5, then add 1g Phospholipid hydrolase, 500ml ether, at 34.6 DEG C, stirring and refluxing hydrolysis 3h.Stratification 3h at reaction mixture puts 4 DEG C, then separatory at 4 DEG C, collect upper organic phase.Lower floor's aqueous phase is the ether re-extract 2 times (each 500ml) of 4 DEG C again by temperature, gained ether phase and organic phase is merged and obtains extracting solution.The lower aqueous layer of raffinate removes Distillation recovery ether, obtains 480ml and distills residual night, sell as liquid fertilizer.Reclaim the ether cyclically utilizing obtained.
In extracting solution, add Glacial acetic acid 150ml, namely have Precipitation, completely, then suction filtration, washing, obtains filter cake gossypol acetate to kept at room temperature overnight order precipitation, and to put in vacuum drying oven 60 DEG C, dry 14h under 1kPa, obtains 50.1g yellow powder.
Through high performance liquid phase inspection, yellow powder is gossypol product, and purity reaches 98%.
Filtrate removes distillation system, reclaims ether and acetic acid, obtains cotton oil lipid acid 480g.Ether and acetic acid cyclically utilizing.
Cotton oil lipid acid, through rectification under vacuum, obtains palmitinic acid 150g, oleic acid 300g and plant asphalt 30g.Through gas-chromatography inspection, the purity of palmitinic acid and oleic acid reaches 98% and 99% respectively.
Example two
By 1000g water content be 45% cotton oil distillation residues concentration be 85% phosphoric acid adjust pH to 2, then add 500ml butanone, be warming up to reflux temperature, stirring and refluxing hydrolysis 5h.Left at room temperature layering 3h put by reaction mixture, then separatory at 24 DEG C, collects upper organic phase.Lower floor's aqueous phase is the butanone re-extract 2 times (each 500ml) of room temperature again by temperature, gained butanone phase and organic phase is merged and obtains extracting solution.The lower aqueous layer salt of wormwood of raffinate is neutralized to neutrality, then removes Distillation recovery butanone, obtains 300ml and distills residual night, sell as liquid fertilizer.Reclaim the butanone cyclically utilizing obtained.
In extracting solution, add Glacial acetic acid 120ml, namely have Precipitation, completely, then suction filtration, washing, obtains filter cake gossypol acetate to kept at room temperature overnight order precipitation, and to put in vacuum drying oven 60 DEG C, dry 14h under 1kPa, obtains 40.1g yellow powder.
Through high performance liquid phase inspection, yellow powder is gossypol product, and purity reaches 98%.
Filtrate removes distillation system, reclaims butanone and acetic acid, obtains cotton oil lipid acid 490g.Butanone and acetic acid cyclically utilizing.
Cotton oil lipid acid, through rectification under vacuum, obtains palmitinic acid 150g, oleic acid 320g and plant asphalt 20g.Through gas-chromatography inspection, the purity of palmitinic acid and oleic acid reaches 98% and 99% respectively.
Claims (10)
1. in cotton oil distillation residues, extract the process for cleanly preparing of gossypol and lipid acid simultaneously.This technique is made up of the following step:
1) with phosphoric acid, cotton oil distillation residues is neutralized, by the pH regulator of cotton oil distillation residues to pH≤7.0;
2) adding extraction agent, under the prerequisite existed there being extraction agent, cotton oil distillation residues being thoroughly hydrolyzed, then carry out liquid-liquid separation, obtain organic phase and aqueous phase;
3) extract aqueous phase with extraction agent, gained extraction liquid and organic phase merge, and form extracting solution.The pH value alkali of raffinate is adjusted to neutrality, then concentrated, recovery extraction agent, reclaim the extraction agent obtained and recycle, enriched product is sold as liquid fertilizer;
4) in extracting solution, add Glacial acetic acid, contained by making wherein, gossypol is with the form Precipitation of gossypol acetate.Then filter, wash, dry, obtain gossypol acetate;
5) gained filtrate and washings merge, and go rectifier unit process, are separated and are extracted agent, acetic acid and cotton oil lipid acid.The extraction agent that recovery obtains and acetic acid recycle;
6) cotton oil lipid acid can sell, and also can obtain palmitinic acid, oleic acid and plant asphalt through negative pressure rectifying, sell as product.
2. extract the process for cleanly preparing of gossypol and lipid acid in cotton oil distillation residues as claimed in claim 1 simultaneously, it is characterized in that described extraction agent can be one or more mixtures formed in benzene,toluene,xylene, Virahol, propyl carbinol, the trimethyl carbinol, tertiary amyl alcohol, ether, ethyl acetate, trichloromethane, butanone or other any organic solvents not miscible with water.The addition of extraction agent is 0.1 ~ 10 times of cotton oil distillation residues weight.
3. in cotton oil distillation residues as claimed in claim 1, extract the process for cleanly preparing of gossypol and lipid acid simultaneously, it is characterized in that described hydrolysis can be made catalyzer with acid and carry out, also can carry out with Phospholipid hydrolase or lipase as catalyst, also can both combinations carry out.
4. in cotton oil distillation residues as claimed in claim 3, extract the process for cleanly preparing of gossypol and lipid acid simultaneously, it is characterized in that when making catalyzer of acid and being hydrolyzed, described hydrolysis in pH≤2,80 ~ 180 DEG C, preferably 100 ~ 148 DEG C, 0.1 ~ 1.0MPa, condition under carry out 0.5 ~ 10 hour.
5. in cotton oil distillation residues as claimed in claim 3, extract the process for cleanly preparing of gossypol and lipid acid simultaneously, it is characterized in that when being hydrolyzed with Phospholipid hydrolase or lipase as catalyst, described hydrolysis carries out 0.5 ~ 10 hour under the optimal pH of enzyme used, optimum temperuture, normal pressure.
6. extract the process for cleanly preparing of gossypol and lipid acid in cotton oil distillation residues as claimed in claim 1 simultaneously, it is characterized in that described liquid-liquid separation can be settlement separate or centrifugation, carry out at normal pressure 0-50 DEG C.
7. in cotton oil distillation residues as claimed in claim 1, extract the process for cleanly preparing of gossypol and lipid acid simultaneously, it is characterized in that described extraction is at 0 ~ 78 DEG C, preferably 4 ~ 38 DEG C, 0.01 ~ 1.0MPa, condition under carry out 1-10 time, the amount of extraction agent needed for each extraction is 80% ~ 120% (v/v) of aqueous phase amount, and extraction time is 0.15 ~ 12hr time
-1.
8. in cotton oil distillation residues as claimed in claim 1, extract the process for cleanly preparing of gossypol and lipid acid simultaneously, it is characterized in that described adjustment raffinate pH alkali used can be ammoniacal liquor, also can be the material that salt of wormwood, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium hydroxide, calcium carbonate, unslaked lime, white lime or any one can be adjusted to pH=6.5 ~ 7.0.
9. extract the process for cleanly preparing of gossypol and lipid acid in cotton oil distillation residues as claimed in claim 1 simultaneously, it is characterized in that described Glacial acetic acid at room temperature adds, its addition is 1 ~ 3 times of contained gossypol amount in extracting solution.
10. in cotton oil distillation residues as claimed in claim 1, extract the process for cleanly preparing of gossypol and lipid acid simultaneously, it is characterized in that described filtration, wash and at room temperature carry out, dry at 30 ~ 180 DEG C, preferably 50 ~ 105 DEG C, 0.01 ~ 1.0MPa, condition under carry out.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410834721.2A CN104450204A (en) | 2014-12-24 | 2014-12-24 | Cleaner production process for synchronously extracting gossypol and fatty acid from cottonseed oil soap |
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| CN201410834721.2A CN104450204A (en) | 2014-12-24 | 2014-12-24 | Cleaner production process for synchronously extracting gossypol and fatty acid from cottonseed oil soap |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693488A (en) * | 2016-03-18 | 2016-06-22 | 江南大学 | Clean production process for high purity gossypol |
| CN107298641A (en) * | 2017-06-07 | 2017-10-27 | 新疆维吾尔自治区中药民族药研究所 | The preparation method of gossypol and the preparation method of gossypol acetate |
| CN107573237A (en) * | 2017-08-18 | 2018-01-12 | 晨光生物科技集团股份有限公司 | A kind of method that high-purity gossypol acetate is prepared in cotton oil refining process |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101016235A (en) * | 2007-02-12 | 2007-08-15 | 西安交通大学 | Method of extracting gossypol acetate from cotton seed oil niger |
| CN101294170A (en) * | 2008-06-20 | 2008-10-29 | 秦皇岛领先科技发展有限公司 | Method for preparing fatty acid by using lipase hydrolyzation of oil and fat |
-
2014
- 2014-12-24 CN CN201410834721.2A patent/CN104450204A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101016235A (en) * | 2007-02-12 | 2007-08-15 | 西安交通大学 | Method of extracting gossypol acetate from cotton seed oil niger |
| CN101294170A (en) * | 2008-06-20 | 2008-10-29 | 秦皇岛领先科技发展有限公司 | Method for preparing fatty acid by using lipase hydrolyzation of oil and fat |
Non-Patent Citations (3)
| Title |
|---|
| MICHAEL K. DOWD ET.AL: "Recovery of gossypol acetic acid from cottonseed soapstock", 《INDUSTRIAL CROPS AND PRODUCTS》 * |
| 丁骁等: "棉酚的制取及其潜在的应用前景", 《中国棉花加工》 * |
| 贾光锋: "棉酚及其衍生物的抗肿瘤效果和生产工艺的研究进展", 《食品与药品》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105693488A (en) * | 2016-03-18 | 2016-06-22 | 江南大学 | Clean production process for high purity gossypol |
| CN107298641A (en) * | 2017-06-07 | 2017-10-27 | 新疆维吾尔自治区中药民族药研究所 | The preparation method of gossypol and the preparation method of gossypol acetate |
| CN107573237A (en) * | 2017-08-18 | 2018-01-12 | 晨光生物科技集团股份有限公司 | A kind of method that high-purity gossypol acetate is prepared in cotton oil refining process |
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