CN108774281B - Method for extracting phytosterol from cottonseed acidified oil - Google Patents
Method for extracting phytosterol from cottonseed acidified oil Download PDFInfo
- Publication number
- CN108774281B CN108774281B CN201811033092.8A CN201811033092A CN108774281B CN 108774281 B CN108774281 B CN 108774281B CN 201811033092 A CN201811033092 A CN 201811033092A CN 108774281 B CN108774281 B CN 108774281B
- Authority
- CN
- China
- Prior art keywords
- sterol
- solution
- phase
- cottonseed
- temperature
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Abstract
The invention relates to a method for extracting phytosterol from cottonseed acidified oil, which comprises the following steps: (1) removing impurities from the cottonseed acidified oil, dehydrating, hydrolyzing under high pressure, and performing gas phase esterification to obtain gas phase esterified liquid containing unsaponifiable substances such as fatty acid methyl ester, sterol, vitamin E, etc.; (2) carrying out reduced pressure distillation on the obtained gas-phase esterification liquid, and distilling out partial fatty acid methyl ester from a light phase; (3) putting the obtained distillation heavy phase and a certain amount of potassium hydroxide aqueous solution into a reactor, and reacting to obtain saponification liquid containing sterol; (4) diluting the saponification solution containing sterol, cooling, and extracting unsaponifiable matters; (5) washing the obtained organic layer with water to neutrality, and performing rotary evaporation concentration to obtain a concentrated solution with high sterol content; (6) heating and dissolving the obtained concentrated solution with 95% ethanol completely, and performing cold separation and crystallization to obtain high-purity sterol; then controlling the temperature, forming crystals in the solution, and drying to obtain the sterol with higher purity. The invention has high purity of extracted sterol, wide source of raw materials and short reaction time.
Description
Technical Field
The invention relates to a method for extracting sterol, in particular to a method for extracting phytosterol from cottonseed acidified oil.
Background
Phytosterol is an important physiologically active substance, widely exists in various vegetable oils, nuts and plant seeds, and is a wide variety of natural phytosterols, mainly comprising four sterols of beta-sitosterol, stigmasterol, brassicasterol and campesterol. The sterol is usually white solid in flake or powder form, and the sterol crystallized by solvent is white scale or needle crystal, wherein the sterol is crystallized in ethanol solvent to form needle or rhombus, and the sterol is needle-punched or long prismatic crystal in dichloromethane solvent. Studies show that the sterol has multiple physiological functions of immunoregulation, inflammation diminishing, fever abatement, tumor resistance, blood fat and cholesterol reduction, free radical removal, skin maintenance and the like, can play a role in preventing and treating cardiovascular diseases such as hypertension, coronary heart disease and the like, is widely applied to the industries of medicine, food and chemical industry, and the phytosterol is also a synthetic precursor of multiple hormones, VD and steroids.
At present, various plant oil deodorized distillates are mainly used as raw materials in the production of the phytosterol, and the soybean oil deodorized distillate (namely DD oil) is mainly used, so that the high-purity phytosterol can be obtained through the processes of esterification, cold precipitation, solvent crystallization, drying and the like. And various plant oil deodorized distillates are derived from byproducts generated in refining of plant oil and fat, the yield is very small (statistical data show that the deodorized distillates only account for 0.1-0.3 percent of the total amount of refined oil), and the yield cannot meet the market demand at present. The cottonseed acidified oil used as the raw material in the method is obtained by acidifying leftovers (soapstock) generated in an alkali refining section during cotton seed oil squeezing through sulfuric acid, and the yield of the cottonseed acidified oil accounts for 5% -7% of the total amount of the cotton seed oil. The cottonseed acidified oil is a mixed oil composed of fatty acid, neutral oil, water impurity, unsaponifiable matter and the like, wherein the content of phytosterol accounts for 1.2-2%, and trace vitamin E and squalene are contained. In addition, the planting area of Xinjiang cotton accounts for more than 50% of the national planting area, wide raw material market is provided, and the transportation and production have great regional advantages. However, due to the complexity of the organic components contained in cottonseed acidified oil, extraction of phytosterols by conventional molecular distillation is difficult to achieve.
Disclosure of Invention
The invention aims to provide a method for extracting phytosterol from cottonseed acidified oil, which has the advantages of high extraction degree of the phytosterol, wide raw material source and short reaction time.
The purpose of the invention is realized as follows: a method for extracting sterol from cottonseed acidified oil,
comprises the following steps:
(1) firstly, cottonseed acidified oil is treated by impurity removal, dehydration, high-pressure hydrolysis and gas-phase esterification processes to obtain a gas-phase esterification liquid containing unsaponifiables such as fatty acid methyl ester, sterol, vitamin E and the like, wherein the process conditions are as follows: hydrolyzing the cottonseed acidified oil under the conditions of the pressure of 5.0-5.5MPa and the temperature of 250-260 ℃ to obtain hydrolyzed acid, adding concentrated sulfuric acid into the hydrolyzed acid as a catalyst, introducing methanol steam, and reacting at the temperature of 70-72 ℃ to obtain a gas phase esterified liquid;
(2) and (2) carrying out reduced pressure distillation on the gas-phase esterified liquid obtained in the step (1), distilling part of fatty acid methyl ester from a light phase, wherein the reduced pressure distillation conditions are as follows: the temperature is controlled between 150 ℃ and 180 ℃, and the vacuum degree is 50 Pa to 200Pa;
(3) putting the distillation heavy phase obtained in the step (2) and a certain amount of potassium hydroxide aqueous solution into a reactor, heating and stirring to perform sufficient saponification reaction, and obtaining saponification liquid containing sterol after reacting for a period of time, wherein the saponification reaction conditions are as follows: the adding amount of the potassium hydroxide-aqueous solution is 2-3 times of the raw material, the concentration of the potassium hydroxide aqueous solution is 3mol/L, the reaction temperature is 110-115 ℃, the reaction time is 5 hours, and the stirring speed is 80rpm;
(4) diluting the sterol-containing saponified solution obtained in the step (3) with water, naturally cooling to room temperature, adding an organic solvent to perform unsaponifiable matter extraction, standing for layering for 0.5 hour, removing a lower-layer aqueous solution, collecting an upper-layer extraction solution in a round-bottom flask, adding 1-1.5 times of water to the material, adding one of diethyl ether, n-hexane and petroleum ether as an organic solvent, and adding 0.5-1 time of the material;
(5) washing the organic layer obtained in the step (4) to be neutral, performing rotary evaporation concentration, and recovering the organic solvent to obtain a concentrated solution with high sterol content;
(6) heating and dissolving the concentrated solution obtained in the step (5) with 95% ethanol completely, and then carrying out cold separation and crystallization to obtain high-purity sterol; the hot melting temperature of the concentrated solution is 65-70 ℃, the concentrated solution is naturally cooled to about 28 ℃ after complete hot melting, then the temperature is controlled to be 1-2 ℃/h and is reduced to about 15 ℃, crystals are formed in the solution, the solution is filtered to obtain a sterol filter cake, the sterol filter cake is dried in an oven at 75-80 ℃ for about 1 h, and the high-purity sterol is obtained after drying.
The invention hydrolyzes neutral grease and partial sterol ester (namely the content of free fatty acid is more than or equal to 90 percent and the content of free sterol reaches 0.35 to 1.2 percent) in cottonseed acidified oil under the high pressure condition of 250 to 260 ℃ and 5.0 to 5.5MPa, then the hydrolyzed acid enters an esterification reaction kettle, methanol steam is introduced for reaction to generate fatty acid methyl ester, the fatty acid methyl ester is decompressed, distilled and concentrated, the distilled light phase fatty acid methyl ester is extracted from the top (if the acid value has special requirements, deacidification and drying are needed), and the distilled heavy phase enters a saponification reactor for saponification and extraction of the phytosterol. The extraction process of the gas phase esterification method is characterized in that 1, gas phase esterification enables most of free fatty acid to be converted into fatty acid methyl ester, and a sterol ester part is decomposed into free fatty acid and free sterol; 2. the methyl ester distillation, saponification and extraction improve the purity of unsaponifiable matters such as sterol, and are more beneficial to the cold separation and crystallization of sterol without being interfered by other organic substances; 3. the method overcomes the process operation difficulties that when the distilled heavy phase of the cottonseed acidified oil is subjected to molecular distillation to extract the sterol, a pipeline is blocked due to high material viscosity, the sterol cannot be extracted due to complex material components, and the vacuum cannot reach stable high vacuum; 4. the method also avoids the characteristics of large using amount of organic solvent, long reaction time and the like when the sterol is extracted; 5. by the method, the high-purity phytosterol is successfully extracted from the cottonseed acidified oil with the sterol content of only 1.2-2%.
Drawings
The invention will be further described with reference to the accompanying drawings, in which fig. 1 is a process flow diagram of the invention.
Detailed Description
A method for extracting sterol from cottonseed acidified oil is shown in figure 1,
comprises the following steps:
(1) firstly, cottonseed acidified oil is treated by impurity removal, dehydration, high-pressure hydrolysis and gas-phase esterification processes to obtain a gas-phase esterification liquid containing unsaponifiables such as fatty acid methyl ester, sterol, vitamin E and the like, wherein the process conditions are as follows: hydrolyzing the cottonseed acidified oil under the conditions of the pressure of 5.0-5.5MPa and the temperature of 250-260 ℃ to obtain hydrolyzed acid, adding concentrated sulfuric acid into the hydrolyzed acid as a catalyst, introducing methanol steam, and reacting at the temperature of 70-72 ℃ to obtain a gas phase esterified liquid;
(2) and (2) carrying out reduced pressure distillation on the gas-phase esterified liquid obtained in the step (1), distilling part of fatty acid methyl ester from a light phase, wherein the reduced pressure distillation conditions are as follows: controlling the temperature at 150-180 ℃ and the vacuum degree at 50-200Pa;
(3) putting the distillation heavy phase obtained in the step (2) and a certain amount of potassium hydroxide aqueous solution into a reactor, heating and stirring to perform sufficient saponification reaction, and obtaining saponification liquid containing sterol after reacting for a period of time, wherein the saponification reaction conditions are as follows: the adding amount of the potassium hydroxide-aqueous solution is 2-3 times of the raw material, the concentration of the potassium hydroxide aqueous solution is 3mol/L, the reaction temperature is 110-115 ℃, the reaction time is 5 hours, and the stirring speed is 80rpm;
(4) diluting the sterol-containing saponified solution obtained in the step (3) with water, naturally cooling to room temperature, adding an organic solvent to perform unsaponifiable matter extraction, standing for layering for 0.5 hour, removing a lower-layer aqueous solution, collecting an upper-layer extraction solution in a round-bottom flask, adding 1-1.5 times of water to the material, adding one of diethyl ether, n-hexane and petroleum ether as an organic solvent, and adding 0.5-1 time of the material;
(5) washing the organic layer obtained in the step (4) to be neutral, performing rotary evaporation concentration, and recovering the organic solvent to obtain a concentrated solution with high sterol content;
(6) heating and dissolving the concentrated solution obtained in the step (5) with 95% ethanol completely, and then carrying out cold separation and crystallization to obtain high-purity sterol; the hot melting temperature of the concentrated solution is 65-70 ℃, the concentrated solution is naturally cooled to about 28 ℃ after complete hot melting, then the temperature is controlled to be 1-2 ℃/hour and is reduced to about 15 ℃, crystals are formed in the solution, the solution is filtered to obtain a sterol filter cake, the sterol filter cake is dried in an oven at 75-80 ℃ for about 1 hour, and the high-purity sterol can be obtained after drying.
Example one:
1. 150.1g of hydrolytic acid (total sterol content is 1.51%, free state content is 0.43%) is weighed into a flask, 2% of concentrated sulfuric acid with concentration of 98% is added, methanol (anhydrous methanol AR) is introduced for gas phase esterification reaction for 5 hours, the reaction temperature is controlled at 70-72 ℃, and esterified liquid (free state sterol content is 0.93%) is obtained.
2. And (3) carrying out reduced pressure distillation on the esterified liquid, distilling out partial fatty acid methyl ester from the top light phase, and ensuring that the sterol content in the heavy phase material is more than 4%. The reduced pressure distillation conditions were: the temperature is controlled between 150 ℃ and 180 ℃, and the vacuum degree is 50 Pa to 200Pa.
3. 40.1g of the heavy phase obtained by distillation and 150ML of a 3mol/L KOH aqueous solution were charged into a reactor, heated to 110 to 115 ℃ and reacted with stirring for 5 hours to obtain a steroid-containing saponified solution.
4. Adding 70ML distilled water into the saponified solution, naturally cooling to room temperature, adding 100ML diethyl ether for extraction, and removing the lower aqueous solution after 0.5 hour.
5. The extract was washed with distilled water to neutrality, and then concentrated on a rotary evaporator and ether was recovered.
6. Heating the concentrated solution to 70 ℃ by using 95% ethanol to completely dissolve the materials, then naturally cooling to about 28 ℃, controlling the cooling rate to be 1-2 ℃/h to stably cool the solution to 15 ℃, forming a large amount of crystals in the solution, filtering to obtain a sterol filter cake, putting the filter cake into an oven to dry for 2 hours, taking out the filter cake, cooling and drying to room temperature, weighing to obtain 1.26g, and detecting the purity to 69.47%.
Example two:
1. weighing 5363 g of hydrolytic acid 161.7 (total sterol content 1.51% and free state content 0.44%) in a flask, adding 2% of concentrated sulfuric acid with concentration of 98%, introducing methanol (anhydrous methanol AR) to perform gas phase esterification for 5h, controlling the reaction temperature at 70-72 deg.C, and obtaining esterified liquid (free state sterol content 0.96%).
2. And (3) carrying out reduced pressure distillation on the esterified liquid, distilling out partial fatty acid methyl ester from the top light phase, and ensuring that the sterol content in the heavy phase material is more than 4%. The reduced pressure distillation conditions were: the temperature is controlled between 150 ℃ and 180 ℃, and the vacuum degree is 50 Pa to 200Pa.
3. 41.2g of the heavy phase obtained by distillation and 150ML of a 3mol/L KOH aqueous solution were charged into a reactor, heated to 110 to 115 ℃ and reacted with stirring for 5 hours to obtain a steroid-containing saponified solution.
4. Adding 70ML distilled water into the saponified solution, naturally cooling to room temperature, adding 100ML diethyl ether for extraction, and discarding the lower aqueous solution after 0.5 hr.
5. The extract was washed with distilled water to neutrality, and then concentrated on a rotary evaporator and ether was recovered.
6. Heating the concentrated solution to 70 ℃ by using 95% ethanol to completely dissolve the materials, then naturally cooling to about 28 ℃, controlling the cooling rate to be 1-2 ℃/h to stably cool the solution to 15 ℃, forming a large amount of crystals in the solution, filtering to obtain a sterol filter cake, putting the filter cake into an oven to dry for 2 hours, taking out the filter cake, cooling and drying to room temperature, weighing to obtain 1.29g, and detecting the purity to 71.27%.
Example three:
1. weighing 5363 g of hydrolytic acid 161.2 (total sterol content 1.51% and free state content 0.44%) in a flask, adding 2% of concentrated sulfuric acid with concentration of 98%, introducing methanol (anhydrous methanol AR) to perform gas phase esterification for 5h, controlling the reaction temperature at 70-72 deg.C, and obtaining esterified liquid (free state sterol content 0.97%).
2. And (3) carrying out reduced pressure distillation on the esterified liquid, distilling out partial fatty acid methyl ester from the top light phase, and ensuring that the sterol content in the heavy phase material is more than 4%. The reduced pressure distillation conditions were: the temperature is controlled between 150 ℃ and 180 ℃, and the vacuum degree is 50 Pa to 200Pa.
3. 38.8g of the heavy phase obtained by distillation and 150ML of a 3mol/L KOH aqueous solution were charged into a reactor, heated to 110 to 115 ℃ and reacted with stirring for 5 hours to obtain a steroid-containing saponified solution.
4. Adding 70ML distilled water into the saponified solution, naturally cooling to room temperature, adding 100ML diethyl ether for extraction, and discarding the lower aqueous solution after 0.5 hr.
5. The extract was washed with distilled water to neutrality, and then concentrated on a rotary evaporator and ether was recovered.
6. Heating the concentrated solution to 70 ℃ by using 95% ethanol to completely dissolve the materials, then naturally cooling to about 28 ℃, controlling the cooling rate to be 1-2 ℃/h to stably cool the solution to 15 ℃, forming a large amount of crystals in the solution, filtering to obtain a sterol filter cake, putting the filter cake into an oven to dry for 2 hours, taking out the filter cake, cooling and drying to room temperature, weighing to obtain 1.32g, and detecting the purity to 75.59%.
Claims (1)
1. A method for extracting sterol from cottonseed acidified oil is characterized by comprising the following steps:
(1) firstly, cottonseed acidified oil is treated by impurity removal, dehydration, high-pressure hydrolysis and gas-phase esterification processes to obtain a gas-phase esterification liquid containing fatty acid methyl ester, sterol and vitamin E unsaponifiable matters, and the process conditions are as follows: hydrolyzing the cottonseed acidified oil under the conditions of the pressure of 5.0-5.5MPa and the temperature of 250-260 ℃ to obtain hydrolyzed acid, adding concentrated sulfuric acid into the hydrolyzed acid as a catalyst, introducing methanol steam, and reacting at the temperature of 70-72 ℃ to obtain a gas phase esterified liquid;
the reaction time of the gas-phase esterification process is 5 hours;
(2) and (2) carrying out reduced pressure distillation on the gas-phase esterified liquid obtained in the step (1), distilling part of fatty acid methyl ester from a light phase, wherein the reduced pressure distillation conditions are as follows: controlling the temperature at 150-180 ℃ and the vacuum degree at 50-200Pa;
the content of sterol in the distillation heavy phase obtained by reduced pressure distillation is more than or equal to 4 percent;
(3) putting the distillation heavy phase obtained in the step (2) and a certain amount of potassium hydroxide aqueous solution into a reactor, heating and stirring to perform sufficient saponification reaction, and obtaining saponification liquid containing sterol after reacting for a period of time, wherein the saponification reaction conditions are as follows: the adding amount of the potassium hydroxide-aqueous solution is 2-3 times of the raw material, the concentration of the potassium hydroxide aqueous solution is 3mol/L, the reaction temperature is 110-115 ℃, the reaction time is 5 hours, and the stirring speed is 80rpm;
(4) diluting the saponification liquid containing sterol in the step (3) with water, naturally cooling to room temperature, adding an organic solvent for unsaponifiable matter extraction, standing for layering for 0.5 hour, removing a lower-layer aqueous solution, collecting an upper-layer extraction solution in a round-bottom flask, adding 1-1.5 times of water into the round-bottom flask, adding one of diethyl ether as an organic solvent, and adding 0.5-1 time of the materials;
(5) washing the organic layer obtained in the step (4) to neutrality, performing rotary evaporation concentration, and recovering the organic solvent to obtain a concentrated solution with high sterol content;
(6) heating and dissolving the concentrated solution obtained in the step (5) by using 95% ethanol completely, and then carrying out cold separation and crystallization to obtain the sterol with higher purity; the hot melting temperature of the concentrated solution is 65-70 ℃, the concentrated solution is naturally cooled to 28 ℃ after complete hot melting, then the temperature is controlled to be 1-2 ℃/h and is reduced to 15 ℃, crystals are formed in the solution, the solution is filtered to obtain a sterol filter cake, the sterol filter cake is dried in an oven at 75-80 ℃ for 1 h, and the sterol with higher purity can be obtained after drying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811033092.8A CN108774281B (en) | 2018-09-05 | 2018-09-05 | Method for extracting phytosterol from cottonseed acidified oil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811033092.8A CN108774281B (en) | 2018-09-05 | 2018-09-05 | Method for extracting phytosterol from cottonseed acidified oil |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN108774281A CN108774281A (en) | 2018-11-09 |
| CN108774281B true CN108774281B (en) | 2023-01-13 |
Family
ID=64028935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811033092.8A Active CN108774281B (en) | 2018-09-05 | 2018-09-05 | Method for extracting phytosterol from cottonseed acidified oil |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN108774281B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110627858B (en) * | 2019-11-01 | 2022-07-05 | 新疆昊睿新能源有限公司 | Method for extracting phytosterol from cottonseed acidified oil |
| CN114773421B (en) * | 2022-05-25 | 2024-03-01 | 沧州市宝来金康生物科技股份有限公司 | Novel process for extracting high-purity phytosterol by using bio-polar resin and continuous reflux liquid-solid extraction |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100334103C (en) * | 2005-09-20 | 2007-08-29 | 南京工业大学 | Method for extracting phytosterol acetate from plant oil asphalt |
| CN100503630C (en) * | 2006-02-07 | 2009-06-24 | 南京工业大学 | Method for extracting plant sterol from plant oil asphalt |
| CN101230288A (en) * | 2007-01-24 | 2008-07-30 | 新疆协力新能源有限责任公司 | Method for producing biological diesel oil |
| CN101525367A (en) * | 2008-03-03 | 2009-09-09 | 徐永林 | Method for extracting phytosterin from plant pitch |
| CN101643495B (en) * | 2009-07-23 | 2012-07-18 | 浙江赞宇科技股份有限公司 | Method for extracting plant sterol from fatty acid or methyl ester pitch from distillate |
| CN105001297B (en) * | 2015-08-03 | 2017-03-08 | 刘火成 | A kind of method extracting plant sterol from plant asphalt |
| CN107011998B (en) * | 2017-05-05 | 2020-07-14 | 杨冠宇 | Biodiesel production system |
-
2018
- 2018-09-05 CN CN201811033092.8A patent/CN108774281B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN108774281A (en) | 2018-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101701029B (en) | Method for extracting natural phytosterin from residual oil of vegetable fat deodorizing distillate | |
| CN110294784B (en) | Method for extracting oryzanol by taking rice bran oil refined soapstock as raw material | |
| CN101607977B (en) | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof | |
| CN101921254B (en) | Method for extracting natural vitamin E from blackberry seeds | |
| CN103145789B (en) | Method for extracting oryzanol from rice bran crude oil | |
| CN101643467B (en) | Method for extracting vitamin E and phytosterin from cottonseed oil deodorizer distillate | |
| CN106977582B (en) | A kind of method of Hydrolysis kinetics phytosterol in deodorization distillate | |
| CN105001297B (en) | A kind of method extracting plant sterol from plant asphalt | |
| CN108774281B (en) | Method for extracting phytosterol from cottonseed acidified oil | |
| CN102224854A (en) | Method for producing flaxseed oil under nitrogen protection | |
| CN101812044A (en) | Method and system for extracting and separating natural VE from plant oil deodorizing distillate | |
| CN101942007B (en) | Method for extracting phytosterol from waste residues generated in biodiesel production and product thereof | |
| CN111393400B (en) | Method for preparing squalene, vitamin E and sterol from fructus momordicae seed kernels | |
| CN108912195A (en) | A method of extracting phytosterol from cottonseed acidification oil | |
| CN107827947A (en) | The method that high-purity sterol is extracted from the residual oil containing sterol ester | |
| CN1301704A (en) | Method for extracting hytosterol from vegitable oil asphalt or tall oil asphalt | |
| CN109609286A (en) | A method of extracting phytosterol from cottonseed acidification oil | |
| CN101709074B (en) | Crystallization method for separating and purifying sterol from vegetable oil deodorizer distillate | |
| CN109824509B (en) | Method for extracting linoleic acid from achyranthes bidentata leaves | |
| CN103524525A (en) | Method for extracting arteannuic acid and arteannuic acid derivative from artemisinin production waste | |
| CN104711112A (en) | Method for realization of combined production of high quality rice bran oil and ferulic acid from rice bran | |
| CN107573237B (en) | Method for preparing high-purity gossypol acetate in cotton oil refining process | |
| CN107955054A (en) | A kind of method that film simultaneous reaction and separation prepares phytosterin ester | |
| CN110627858B (en) | Method for extracting phytosterol from cottonseed acidified oil | |
| CN106831922B (en) | The method of one-step method separating high-purity phytosterol and vitamin E |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |