CN101016235A - Method of extracting gossypol acetate from cotton seed oil niger - Google Patents
Method of extracting gossypol acetate from cotton seed oil niger Download PDFInfo
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- CN101016235A CN101016235A CN 200710017398 CN200710017398A CN101016235A CN 101016235 A CN101016235 A CN 101016235A CN 200710017398 CN200710017398 CN 200710017398 CN 200710017398 A CN200710017398 A CN 200710017398A CN 101016235 A CN101016235 A CN 101016235A
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Abstract
The invention discloses an extracting method of gossypol acetate from cotton seed oil soap stock, which comprises the following steps: dissolving cotton seed oil soap stock into organic acid solvent; transmitting into ultrasonic equipment to do ultrasonic extraction; heating to reflux; centrifuging; separating; decompressing; condensing; acidifying through acetic acid; inducing to crystallize through ultrasound; sucking to obtain the product as yellow crystal with melting point (mp) at 171-178 deg.c; displaying the consistent ultraviolet adsorption spectrum and infrared spectrum with standard mass completely; testing the most ultraviolet adsorption of gossypol acetate at 365nm through VIA method with content at 80-95% and receiving rate at 1-3%.
Description
Technical field
The present invention relates to a kind of method of extracting gossypol acetate, particularly a kind of method of from cotton oil distillation residues, extracting gossypol acetate.
Background technology
Gossypol has another name called cotton toxin or gossypol, is a kind of yellow polyphenol pigment that forms in the cotton body, and content is higher in cottonseed.When processing cottonseed protein or refining cotton wool oil, in order to reduce the content of free lipid acid, phosphatide, pigment and gossypol in the product, improve the quality of product, often add sig water in process of production and carry out refining.During alkali refining, the whole gossypols in the Oleum Gossypii semen enter into soap stock, change into the compound of various dark colors under alkaline condition easily, thereby make soap stock become Vandyke brown.Cotton oil distillation residues is dropped as refuse usually, has caused environmental pollution to a certain degree.Yet the content of gossypol can be used as the important drugs raw material in the medicine industry up to 1%-7% in the cotton oil distillation residues.As far back as the seventies, China medicine worker has just found that gossypol has the function of male-contraception effect, is commonly used for male contraceptive pill.Over past ten years, scientific and technical personnel both domestic and external have carried out more careful research to the purposes of gossypol, find that gossypol treatment gynaecopathia and anti-tumor aspect all show good prospects for application and economic worth.Especially in recent years, developed countries such as the U.S. have tentatively illustrated the antitumor mechanism of gossypol through concentrating on studies, and make gossypol demonstrate great potential in malignant tumour fields such as treatment cancer of the stomach, liver cancer, carcinoma of the pancreas.The biological activity ratio of natural gossypol is higher, therefore, extracts the demand that natural gossypol has become market from plant tissue.Because gossypol is stable inadequately, normally the mode with gossypol acetate is present in occurring in nature, and what therefore extract is gossypol acetate mostly.
Chinese invention patent ZL 89107264 " technology of extracting cotton phenol " discloses a kind of method of extracting gossypol acetate from absorbent cotton benevolence.This method at first heats the fat of taking out in the cotton seed kernel-extracting with the fatty extractor of series connection, then with ether extracting absorbent cotton benevolence, utilizes Glacial acetic acid crystallization ether extract to get the gossypol acetate crude product then, after the refining gossypol acetate of sodium bisulfite and ether.Leaching process is finished automatically, has reduced lipid content in the cotton benevolence, has improved quality product.Its production cycle shortens to some extent, has improved the output capacity of gossypol acetate.Chinese invention patent ZL 200410025855.6 " production method of gossypol acetate raw material " discloses a kind of method of utilizing acetone thermal backflow-acetic acid recrystallization gossypol, it mainly is the aqueous acetone solution 1 hour of 75%-78% that cottonseed meal cake soak at room temperature is doubly measured at 1-2, and, re-use the Glacial acetic acid recrystallization and obtain the bulk drug gossypol acetate at 40 ℃ of refluxing extraction gossypols of multi-function extractor.This technology will shorten to original half production cycle, and cost also is reduced to the 1/3-1/2 of traditional technology.Chinese patent literature CN 1789226A " utilizes the method and the isolated plant of gossypol in the microwave radiation extraction cottonseed " and discloses a kind of method of utilizing microwave radiation to extract the gossypol that is used to kill mouse from cottonseed, at first basic extractant or acetone-water soak and pulverize cottonseed 5-7h, then place the radiation under 500-650W of special microwave device to extract 4-12 minute, in extracting solution, add elutriation then and go out rough gossypol, after acetic acidization, concentrate, recrystallization must make with extra care gossypol acetate, this method has the time spent short than traditional extraction process, the characteristics that extraction yield is high.
The described natural acetic acid gossypol of above-mentioned open source literature mostly is to extract from cotton benevolence or crude cotton seed oil, because gossypol content lower (being respectively 0.5-2.5% and 0.1-1.3%) therein, it is big to cause extracting the solvent demand, time-consuming taking a lot of work, and product cost is higher.And if cotton benevolence or Oleum Gossypii semen after extracting are used in continuation, can make and introduce poisonous organic solvents such as acetone, aniline and ether in cottonseed protein or the edible cotton oil, will certainly bring potential danger to the safety of food and feed.
Summary of the invention
The technical problem to be solved in the present invention is intended to provide a kind of method of extracting gossypol acetate from the cotton oil distillation residues of cottonseed processing waste, can be fast, the low high purity medical gossypol acetate that impurely prepares, and reduce the demand of extracting solvent, and simplify production technique, reduce product cost.
For reaching above purpose, the present invention takes following technical scheme to be achieved.
A kind of method of extracting gossypol acetate from cotton oil distillation residues comprises the steps:
A. be 1 with cotton oil distillation residues by the feed liquid weight ratio earlier: 1-1: 20 join in the organic solvent that acidity is 0.1-4.0mol.L-1, after stirring, place ultrasonic equipment to extract 5-60 minute, heating in water bath backflow mixing solutions is after 30-300 minute then, and ice-water bath is cooled to room temperature; Described organic solvent can be any in methyl alcohol, ethanol, ether, chloroform, acetone, the butanone.Also can be two or more mixtures;
B. cooling liqs is in whizzer centrifugation 20-30 minute, and with 2 times to the described organic solvent washing water of cooling fluid volume three times, collect all organic phases;
C. the organic phase of collecting is evaporated to volume and is original 1/3 and obtain concentrated solution;
D. add to be placed on behind the Glacial acetic acid of concentrated solution 1/6-1/2 volume and carry out supersonic induced crystallization 3-10 minute in the ultrasonic device, the Acetic Acid Glacil gossypol occurs;
E. decompress filter, and become colourless up to filtrate with normal hexane washing gossypol acetate filter cake;
F. recycle described organic solvent and Glacial acetic acid and carry out recrystallization, the purifying gossypol acetate after drying, promptly makes the gossypol acetate finished product.
In the such scheme, can add any of hydrochloric acid, oxygen acid or its acid anhydrides in the described organic solvent, or the mixture of two kinds of acid; Described oxygen acid can be any one in sulfuric acid, phosphoric acid, the nitric acid.
Described cotton oil distillation residues can adopt processing such as feed factory, grease factory, albumen factory and handle alkalization cotton oil distillation residues in the Oleum Gossypii semen process, or squeezing or leach the mixture of the cotton oil distillation residues in the Oleum Gossypii semen refining process.Ultrasonic power in described ultrasonic extraction and the supersonic induced crystallisation step is 50-1000W.
The inventive method is extracted the gossypol acetate method than prior art and had following tangible beneficial effect: (1) adopts steps such as supersound extraction, acid hydrolysis and supersonic induced crystallization, the production cycle of gossypol acetate can be shortened to 48 hours from 56-96 hour, make the once extraction product content of gossypol acetate surpass 80%, the content of gossypol acetate is up to 96% in the crude extract, has improved production efficiency; (2) the present invention utilizes waste cotton oil distillation residues that cotton oil source mill, cottonseed protein extraction plant, feed-processing plant etc. abandon during cottonseed in processing as raw material, can reduce the pollution of cotton oil distillation residues on the one hand to surrounding environment, can reclaim high-load gossypol acetate on the other hand, and the aboundresources of discarded cotton oil distillation residues, raw materials cost are very low; (3) this method is in reclaiming the gossypol acetate process, can alleviate the pressure that product is further purified, save alkali than alkali lye extracting method and put forward process, production technique is simpler, the extraction agent demand is little in addition, can reduce the production cost of gossypol acetate greatly, have rapidly and efficiently, energy-conservation, pollute little characteristics.(4) the gossypol acetate product that the present invention extracted has important use to be worth aspect medicine, especially in the performance of treatment gynaecopathia and anti-tumor aspect good prospects for application and economic worth, for pharmaceutical industry provides abundant raw material.
Description of drawings
Fig. 1 is the process frame chart of gossypol acetate method in the ultrasonic extraction cotton oil distillation residues of the present invention;
Fig. 2 is the embodiment of the invention 1 and embodiment 2 gained gossypol acetates and the UV scanning collection of illustrative plates of standard substance when concentration is 15ug/mL, and maximum absorption wavelength is 365nm.
Fig. 3 is the infrared spectrogram of gained gossypol acetate of the present invention.Wherein Fig. 3 (a), Fig. 3 (b) are respectively the infrared spectra of example 1 and example 2 gained gossypol acetates, the IR (cm in the spectrogram
-1): 3424vOH (stretching vibration of hydroxyl O-H key); 2960vCH
3-(antisymmetric stretching vibration of methyl c h bond); 2930v (CH
3)
2CH-(stretching vibration of methylene radical c h bond); 2874vC-H (symmetrical stretching vibration of methyl c h bond); 2610 vO=C-H (stretching vibration of aldehyde radical c h bond); 1711 vO=C-H (stretching vibration of aldehyde carbonyl C=O key); 1611,1579 vC-H (aromatic ring C=C skeletal vibration); 1440 vCH
3COO
-(carboxylic acid ion CH
3COO
-Stretching vibration); 1379 vO-H (formation vibration of phenolic hydroxyl group O-H); 1269 vC-O (stretching vibration of phenol C-O); 1176,1123v (CH
3)
2CH-(sec.-propyl C-C skeletal vibration); 966,912,841vC-H (aromatic ring C-H flexural vibration).
Embodiment
The present invention is described in further detail below in conjunction with drawings and Examples.
The 100 gram grease factory cotton oil distillation residues that weigh with scale join 100 grams, and to regulate its acidity with sulfuric acid be 0.1mol.L
-1Methanol solution in, stir, placing power is the ultrasonic extraction equipment of 50W, after the ultrasonic extraction 5 minutes, after heating in water bath refluxed 30 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 20 minutes, and with 2 times to the methanol wash water of cooling fluid volume three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, in concentrated solution, add the Glacial acetic acid of 1/6 volume, simultaneously induced crystallization 3 minutes in the ultrasonic device of 100W, through decompress filter, normal hexane washing and dry after, obtain 0.87 the gram product, its infrared spectrogram consistent with the UV scanning collection of illustrative plates with the gossypol acetate standard substance (Fig. 2, Fig. 3)., under the 365nm wavelength,, record its purity and reach 82.9% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
Embodiment 2
The 100 gram albumen factory cotton oil distillation residues that weigh with scale join 500 grams, and to regulate its acidity with phosphoric acid be 0.5mol.L
-1Ethanol liquid in, stir, placing power is the ultrasonic extraction equipment of 100W, after the ultrasonic extraction 10 minutes, after heating in water bath refluxed 80 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 20 minutes, and with 2 times to the washing with alcohol water of cooling fluid volume three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, in concentrated solution, add the Glacial acetic acid of 1/4 volume, simultaneously induced crystallization 5 minutes in the ultrasonic device of 100W, through decompress filter, normal hexane washing and dry after, obtain 1.07 the gram products, its infrared spectrogram consistent with the UV scanning collection of illustrative plates with the gossypol acetate standard substance (Fig. 2, Fig. 3)., under the 365nm wavelength,, record its purity and reach 95.9% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
Embodiment 3
The 100 gram grease factory cotton oil distillation residues that weigh with scale join 1000 grams, and to regulate its acidity with nitric acid be 1.0mol.L
-1Ether solution in, stir, placing power is the ultrasonic extraction equipment of 200W, after the ultrasonic extraction 20 minutes, after heating in water bath refluxed 100 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 20 minutes, and with 2 times to the ether of cooling fluid volume washing water three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, the Glacial acetic acid that in concentrated solution, adds 1/3 volume, induced crystallization 8 minutes in the ultrasonic device of 200W simultaneously is through decompress filter, normal hexane washing and dry after, obtain 0.94 gram product, its infrared spectrogram is consistent with the gossypol acetate standard substance with the UV scanning collection of illustrative plates., under the 365nm wavelength,, record its purity and reach 92.4% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
Embodiment 4
The 100 gram albumen factory cotton oil distillation residues that weigh with scale join 1500 grams, and to regulate its acidity with 1: 1 hydrochloric acid and nitrate mixture be 2.0mol.L
-1Chloroform solution in, stir, placing power is the ultrasonic extraction equipment of 500W, after the ultrasonic extraction 30 minutes, after heating in water bath refluxed 150 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 30 minutes, and with 2 times to the chloroforms of cooling fluid volume washing water three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, the Glacial acetic acid that in concentrated solution, adds 1/2 volume, induced crystallization 10 minutes in the ultrasonic device of 500W simultaneously is through decompress filter, normal hexane washing and dry after, obtain 1.01 gram products, its infrared spectrogram is consistent with the gossypol acetate standard substance with the UV scanning collection of illustrative plates., under the 365nm wavelength,, record its purity and reach 94.6% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
100 gram weight that weigh with scale ratio is that the cotton oil distillation residues that mixes of 1: 1 albumen factory and grease factory joins 2000 grams to regulate its acidity with hydrochloric acid be 3.0mol.L
-1Acetone solution in, stir, placing power is the ultrasonic extraction equipment of 500W, after the ultrasonic extraction 40 minutes, after heating in water bath refluxed 200 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 30 minutes, and with 2 times to the washing with acetone water of cooling fluid volume three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, the Glacial acetic acid that in concentrated solution, adds 1/3 volume, induced crystallization 10 minutes in the ultrasonic device of 500W simultaneously is through decompress filter, normal hexane washing and dry after, obtain 1.02 gram products, its infrared spectrogram is consistent with the gossypol acetate standard substance with the UV scanning collection of illustrative plates., under the 365nm wavelength,, record its purity and reach 95.1% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
Embodiment 6
The 100 gram feed factory cotton oil distillation residues that weigh with scale join 1000 grams, and to regulate its acidity with hydrochloric acid be 4.0mol.L
-1Butanone in, stir, placing power is the ultrasonic extraction equipment of 1000W, after the ultrasonic extraction 30 minutes, after heating in water bath refluxed 150 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 30 minutes, and with 2 times to the butanone of cooling fluid volume washing water three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, the Glacial acetic acid that in concentrated solution, adds 1/2 volume, induced crystallization 10 minutes in the ultrasonic device of 1000W simultaneously is through decompress filter, normal hexane washing and dry after, obtain 0.99 gram product, its infrared spectrogram is consistent with the gossypol acetate standard substance with the UV scanning collection of illustrative plates., under the 365nm wavelength,, record its purity and reach 91.4% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
Embodiment 7
The 100 gram feed factory cotton oil distillation residues that weigh with scale join 2000 grams, and to regulate its acidity with nitric acid be 3.0mol.L
-11: 1 acetone of weight ratio and the mixture of ether in, stir, placing power is the ultrasonic extraction equipment of 300W, after the ultrasonic extraction 60 minutes, after heating in water bath refluxed 300 minutes, be cooled to room temperature, in 3000 rev/mins of centrifugations 30 minutes, and with 2 times to the washing with acetone water of cooling fluid volume three times, collect organic phase, after in vacuum tightness is Rotary Evaporators under the 0.08Mpa, being concentrated into volume and being original 1/3, the Glacial acetic acid that in concentrated solution, adds 1/3 volume, induced crystallization 10 minutes in the ultrasonic device of 500W simultaneously is through decompress filter, normal hexane washing and dry after, obtain 1.07 gram products, its infrared spectrogram is consistent with the gossypol acetate standard substance with the UV scanning collection of illustrative plates., under the 365nm wavelength,, record its purity and reach 87.9% according to 2000 editions two described methods of appendix VIA of Chinese Pharmacopoeia with the gossypol acetate standard control of Sigma company.
The used ultrasonic device of the foregoing description can be in ultrasonic cleaning machine, probe type ultrasonic pulverizer and the circulating ultrasonic extracting machine any one.
Gossypol acetate extracts the quality determining method of product:
(1) gets the about 3mg of this product, add 1 in sulfuric acid, promptly show scarlet.
(2) get the about 3mg of this product, add ethanol 3mL, after the dissolving, add 2 of 1% iron trichloride ethanolic solns, promptly show sap green.
(3) it is an amount of to get this product fine powder, adds the water jolting, gets filtrate 2mL, adds sulfuric acid number droplet, and the special odor of acetic acid is promptly sent in heating.
(4) it is an amount of to get this product, adds the water jolting, filters, and gets filtrate 2mL, adds sulfuric acid and small amount of ethanol, and the fragrance of vinyl acetic monomer is promptly sent in heating.
(5) get gossypol acetate solution, measure according to spectrophotometry (2000 editions two appendix IVA of Chinese Pharmacopoeia), at 278 ± 1nm, there is maximum absorption at 288 ± 1nm and 365 ± 1nm wavelength place.
Weight loss on drying: get this product and put in the vacuum drier, be dried to constant weight at 60 ℃, weight loss must not surpass 1% (2000 editions two appendix VIII L of Chinese Pharmacopoeia).
Residue on ignition: must not surpass 0.2% (2000 editions two appendix VIII N of Chinese Pharmacopoeia).
Related substance: get this product, chlorination is copied into the solution that contains 10mg among every 1mL, as need testing solution: it is an amount of that this solution is drawn in economy and trade, add chloroform and be diluted to the solution that contains 0.05mg among every 1mL, solution in contrast, test according to tlc (2000 editions two appendix VB of Chinese Pharmacopoeia), drawing each 10 μ L of above-mentioned two kinds of solution and put respectively on same polymeric amide thin layer plate, is developping agent with normal hexane-chloroform-Glacial acetic acid (80: 20: 7), after the expansion, dry, observe immediately, the apparent impurity spot of need testing solution must not be above 2, wherein the spot of any point color and contrast solution relatively must not be darker.
Assay: it is an amount of to get this product, accurately claims surely, adds new distillatory chloroform and is mixed with the solution that every 1mL contains 10 μ g, according to spectrophotometry (2000 editions two appendix IVA of Chinese Pharmacopoeia), measures optical density at 365nm wavelength place, presses C
32H
34O
10Uptake factor (E
1% 1cm) be 358 calculating, promptly.
Claims (5)
1. a method of extracting gossypol acetate from cotton oil distillation residues is characterized in that, comprises the steps:
A. is 1 with cotton oil distillation residues by the feed liquid weight ratio earlier: 1-1: 20 to join acidity be 0.1-4.0mol.L
-1Organic solvent in, after stirring, place ultrasonic equipment to extract 5-60 minute, heating in water bath backflow mixing solutions is after 30-300 minute then, ice-water bath is cooled to room temperature; Described organic solvent is any one or two kinds of above mixture in methyl alcohol, ethanol, ether, chloroform, acetone, the butanone;
B. cooling liqs is in whizzer centrifugation 20-30 minute, and with 2 times to the described organic solvent washing water of cooling fluid volume three times, collect all organic phases;
C. the organic phase of collecting is evaporated to volume and is original 1/3, obtain concentrated solution;
D. add to be placed on behind the Glacial acetic acid of concentrated solution 1/6-1/2 volume and carry out supersonic induced crystallization 3-10 minute in the ultrasonic device, the Acetic Acid Glacil gossypol occurs;
E. decompress filter, and become colourless up to filtrate with normal hexane washing gossypol acetate filter cake;
F. recycle described organic solvent and Glacial acetic acid and carry out recrystallization, the purifying gossypol acetate after drying, promptly makes the gossypol acetate finished product.
2. the method for extracting gossypol acetate from cotton oil distillation residues according to claim 1 is characterized in that the acidity material in the described organic solvent is any of hydrochloric acid, oxygen acid or its acid anhydrides, or the mixture of two kinds of acid;
3. the method for extracting gossypol acetate from cotton oil distillation residues according to claim 2 is characterized in that described oxygen acid is any in sulfuric acid, phosphoric acid, the nitric acid.
4. the method for from cotton oil distillation residues, extracting gossypol acetate according to claim 1, it is characterized in that, described cotton oil distillation residues is the alkalization cotton oil distillation residues in processing and the processing Oleum Gossypii semen process, or the mixture of the cotton oil distillation residues in squeezing or the leaching Oleum Gossypii semen refining process.
5. the method for extracting gossypol acetate from cotton oil distillation residues according to claim 1 is characterized in that the ultrasonic power in described ultrasonic extraction and the supersonic induced crystallisation step is 50-1000W.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103451023A (en) * | 2012-09-13 | 2013-12-18 | 山东三星玉米产业科技有限公司 | Processing method of corn oil nigre |
| CN103725421A (en) * | 2013-09-25 | 2014-04-16 | 山东渤海实业股份有限公司 | Method for increasing utilization rate of cottonseed oil mixture refining by-products |
| CN103989030A (en) * | 2014-05-16 | 2014-08-20 | 江苏大学 | Method for ultrasonic-assisted detoxification of cotton seed meal |
| CN104450204A (en) * | 2014-12-24 | 2015-03-25 | 江南大学 | Cleaner production process for synchronously extracting gossypol and fatty acid from cottonseed oil soap |
| CN106146295A (en) * | 2015-04-23 | 2016-11-23 | 新疆凯欣生物科技有限责任公司 | Gossypol acetate crude product purifying technique |
| 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 |
| CN108276263A (en) * | 2018-04-09 | 2018-07-13 | 中国科学院新疆理化技术研究所 | A method of preparing free gossypol by raw material of gossypol acetate |
| CN113717796A (en) * | 2021-08-20 | 2021-11-30 | 南京林业大学 | Method for converting fatty acid in one step by ultrasonic-assisted pressure hydrolysis of soapstock |
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| CN1233615C (en) * | 2004-02-02 | 2005-12-28 | 陕西盘龙制药集团有限公司 | Production process for gossypol acetic acid materials |
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| CN103451023A (en) * | 2012-09-13 | 2013-12-18 | 山东三星玉米产业科技有限公司 | Processing method of corn oil nigre |
| CN103725421A (en) * | 2013-09-25 | 2014-04-16 | 山东渤海实业股份有限公司 | Method for increasing utilization rate of cottonseed oil mixture refining by-products |
| CN103725421B (en) * | 2013-09-25 | 2015-07-15 | 山东渤海实业股份有限公司 | Method for increasing utilization rate of cottonseed oil mixture refining by-products |
| CN103989030A (en) * | 2014-05-16 | 2014-08-20 | 江苏大学 | Method for ultrasonic-assisted detoxification of cotton seed meal |
| CN104450204A (en) * | 2014-12-24 | 2015-03-25 | 江南大学 | Cleaner production process for synchronously extracting gossypol and fatty acid from cottonseed oil soap |
| CN106146295A (en) * | 2015-04-23 | 2016-11-23 | 新疆凯欣生物科技有限责任公司 | Gossypol acetate crude product purifying technique |
| CN106146295B (en) * | 2015-04-23 | 2019-04-30 | 新疆凯欣生物科技有限责任公司 | Gossypol acetate crude product purifying technique |
| 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 |
| CN108276263A (en) * | 2018-04-09 | 2018-07-13 | 中国科学院新疆理化技术研究所 | A method of preparing free gossypol by raw material of gossypol acetate |
| CN108276263B (en) * | 2018-04-09 | 2021-03-09 | 中国科学院新疆理化技术研究所 | Method for preparing free gossypol by using gossypol acetate as raw material |
| CN113717796A (en) * | 2021-08-20 | 2021-11-30 | 南京林业大学 | Method for converting fatty acid in one step by ultrasonic-assisted pressure hydrolysis of soapstock |
| CN113717796B (en) * | 2021-08-20 | 2024-06-11 | 南京林业大学 | Method for converting fatty acid by ultrasonic-assisted nigre pressurized hydrolysis in one step |
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|---|---|
| CN101016235B (en) | 2010-08-11 |
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