CN101607977A - Extract the method and the technology of purifying natural plant sterol in the oil deodorization distillate residual oil - Google Patents
Extract the method and the technology of purifying natural plant sterol in the oil deodorization distillate residual oil Download PDFInfo
- Publication number
- CN101607977A CN101607977A CNA2009100692410A CN200910069241A CN101607977A CN 101607977 A CN101607977 A CN 101607977A CN A2009100692410 A CNA2009100692410 A CN A2009100692410A CN 200910069241 A CN200910069241 A CN 200910069241A CN 101607977 A CN101607977 A CN 101607977A
- Authority
- CN
- China
- Prior art keywords
- oil
- sterol
- technology
- residual oil
- crystallization
- 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.)
- Granted
Links
Images
Landscapes
- Steroid Compounds (AREA)
Abstract
The present invention relates to a kind of catalytic decomposition and solvent crystallization technology of from grease deodorized distillate, extracting the purifying natural plant sterol.This technological process is as follows: residual oil of vegetable fat deodorizing distillate and solvent are put into heatable catalytic decomposition in the reactor, after separating water layer, oil phase is transferred in the cold analysis tower, and the adding organic solvent carries out dynamic gradient cooling crystallization, after the slaking insulation, filter and promptly get the sterol crude product, thick product can obtain the pure product of sterol through the secondary solvent crystallization.Sterol ester in the residual oil can be converted into sterol by catalytic decomposition, adopt the technology of dynamic gradient crystallization, improve the quality and the yield of product.Adopt technology gained sterol purity of the present invention to be higher than 90%, can meet the need of market.The yield of sterol reaches 5~40% of raw material residual oil, and the resistates of filtrate after reclaiming solvent that has separated sterol can be used as slushing oil.Technology of the present invention is simple, easy handling, controllability is good, cost is low, be easy to industrialization.
Description
Technical field
The present invention relates to biological chemical field, from oil deodorization distillate residual oil, extract the catalytic decomposition and the solvent crystallization purifying process of natural phytosterin specifically.
Background technology
Plant sterol extensively is present in plant and the plant seed, is one of composition that constitutes in the plant materials in cytolemma.Plant sterol is a kind of crude substance with important biological value, nontoxicity, have characteristics such as good emulsifying and stability, therefore be widely used in the relevant industries of every field such as medicine, food, household chemicals, growth of animal agent and chemical industry, weaving.Contain Sitosterol in the plant sterol, multiple components such as campesterol, brassicasterol, Stigmasterol have stronger anti-inflammatory and antiinflammation and directly as anti-inflammatory drug.Clinically both at home and abroad prove, natural phytosterin has the important physical active function to human body, can suppress the absorption of human body to cholesterol, promote the cholesterol degradation metabolism, the biochemistry that suppresses cholesterol is synthetic, coronary heart disease, atherosclerosis, ulcer, skin squama cancer, cervical cancer etc. there are significant prevention and result of treatment, stronger anti-inflammatory action is arranged, also can be used as the hold back agent that gallbladdergallstonecholetithiasis forms.As the w/o type emulsifying agent, be used for the production of cream frost, have usability good (auxilliary malleability is good, smooth sticking), good endurance, characteristics such as not perishable.In addition, plant sterol still is important steroid drugs and VITAMIN d
3Raw materials for production.
Plant sterol mainly comes from vegetable oil refining tankage, particularly deodorization distillate (DD oil).Vegetable fat deodorizing distillate is the by product of last process in the oil and fat refining process, and main component is free fatty acids, glyceryl ester, sterol, sterol ester, tocopherol (being vitamin-E), water and other oxygenolysis products.The domestic and international at present treatment process to deodorization distillate mostly is greatly: deodorization distillate at first after sulfuric acid catalysis and the esterification of base catalysis secondary, filters to isolate thick sterol, and filtrate can obtain vitamin E oil and fatty acid methyl ester through molecular distillation, and resistates is residual oil.The yield of residual oil is 10~20% of a stock oil, mostly all with waste sludge discharge, environment is caused bigger pollution at present.
Analyze to find that contain 10~35% plant sterol and 10~40% lipid acid in the residual oil of vegetable fat deodorizing distillate, mainly the chemical combination attitude form with the fatty acid sterols ester exists.Residual oil is dirt cheap; natural phytosterin then has very high economic worth; therefore extract natural phytosterin from residual oil of vegetable fat deodorizing distillate; has considerable economic worth; residuum still can be used for preparing tensio-active agent or biofuel and slushing oil; make vegetable fat deodorizing distillate reach the most effective comprehensive utilization; significantly reduced the discharging of waste residue; the protection environment; have crucial economy and social effect, meet the state basic policy and the related industries policy of the present energy-saving and emission-reduction of China.
United States Patent (USP) 4524024 has been reported and extracted sterol and lipid acid from Yatall MA pitch, elder generation's hydrolysis Yatall MA pitch, allow free fatty acids distill by distillation then, obtain being rich in the residue of sterol and sterol ester, use the high molecular alcohol dissolution residual substance, non-dissolved is partly removed, obtain dissolved sterol phase, evaporating solvent (high molecular alcohol) obtains thick sterol.Chinese patent 200610038172.3 has been reported from the distillation residue of nigre of vegetable oil rectifying lipid acid behind highly pressured hydrolysis, it is the method for extracting plant sterol in the plant oil asphalt, this method is converted into fatty acid ester with esterification with the free fatty acids in the raw material, obtain being rich in the oil phase of a large amount of sterol esters by washing, by organic solvent the sterol ester alcoholysis in the oil phase is obtained sterol then.Chinese patent 200710062149.2 has been reported the method for separation and Extraction plant sterol and vitamin-E from soyabean deodorization distillate, with supercutical fluid soyabean deodorization distillate is extracted earlier, the extract remainder dissolving that about the acetone boiling temperature, refluxes, the slow decrease temperature crystalline of room temperature, protect ripe crystallization, suction filtration obtains the sterol crystal.Chinese patent 200510114851.x has reported and extracted natural VE and sterol from vegetable oil and fat refining and deodorizing distillate, at first adopt distillation to remove lipid acid, base catalysis esterification then, the cold analysis sterols separated, the filtrate molecular distillation obtains fatty acid methyl ester, vitamin E oil and residual oil.Above-mentioned patent does not all relate to separation and Extraction natural phytosterin from the residual oil behind the vegetable fat deodorizing distillate molecular distillation.
We are at last patent " a kind of method of extracting natural phytosterin from residual oil of vegetable fat deodorizing distillate " (application number: 200910067652.6) reported the method for extracting natural phytosterin from oil deodorization distillate residual oil, comprised catalytic decomposition, oily water separation, solvent crystallization and separating step.At this method, we improve each step, have optimized processing parameter, mainly comprise the optimization to sampling condition, agitation condition, cooling condition, crystallization slaking condition and secondary crystal purification condition.
Summary of the invention
The object of the present invention is to provide a kind of technology of from oil deodorization distillate residual oil, extracting natural phytosterin.
Technological process of the present invention is as follows:
(1) residual oil of vegetable fat deodorizing distillate, solvent are joined in the reactor, the mass ratio of residual oil and solvent is 1: 0.1~2, under agitation is heated to 60~100 ℃, and the two is mixed;
(2) catalyzer of adding residual oil weight 10%~80% in reactor, cartalytic decomposition effect is 1~10 hour under heated and stirred;
(3) after reaction is finished, be acidified with acid, separate then and remove water layer to pH=1~7;
(4) oil phase is transferred in the cold analysis tower, and adds the organic solvent of 2~6 times of quality of oil phase, be warming up to 50~90 ℃, under 50~150 rev/mins rotating speed, stir oil phase is dissolved fully;
(5) carry out dynamic gradient cooling crystallization with 5~10 ℃/hour, when a large amount of tiny crystal grains were separated out, stir speed (S.S.) transferred to 20~80 rev/mins, was incubated 0.25~5 hour, continued cooling by 1~4 ℃/hour afterwards;
(6) when temperature reaches-10~25 ℃ curing temperature scope, stop to stir and being incubated 4~48 hours;
(7) mixed solution after the crystallization is carried out suction filtration or, press filtration and use organic solvent washing promptly gets the thick product of sterol;
(8) the thick product of sterol is dissolved in the organic solvent of 2~10 times of weight, being heated to 50~90 ℃ dissolves sterol fully, under 50~150 rev/mins rotating speed, carry out dynamic gradient cooling crystallization with 1~10 ℃/hour, when temperature reaches-10~25 ℃ curing temperature scope, stop to stir and being incubated 4~48 hours, then crystallization mixture is filtered or press filtration, and use organic solvent washing, promptly get the natural phytosterin product.
Press such scheme, described residual oil of vegetable fat deodorizing distillate means in soybean oil, rapeseed oil, peanut oil, Rice pollard oil, sunflower seed oil, plam oil, numb maple oil or the sweet oil one or more the residual solution of deodorization distillate behind molecular distillation;
Press such scheme, the used solvent of described catalyzed reaction is that temperature is 60~100 ℃, and the reaction times is 1~10 hour;
Press such scheme, described catalyzer is LiOH, NaOH, KOH, Ca (OH)
2, Na
2O, K
2O, CaO, CH
3ONa, C
2H
5ONa, K
2CO
3, Na
2CO
3, Li
2CO
3, in ammoniacal liquor or the magnesium aluminum-hydrotalcite one or more.
Press such scheme, described acid is one or more in sulfuric acid, hydrochloric acid, phosphoric acid or the Hydrogen bromide.
Press such scheme, described organic solvent is methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, acetone, butanone, pimelinketone, ethyl acetate, ethyl formate, one or more in methyl acetate, sherwood oil, normal hexane, hexanaphthene, Skellysolve A or the pentamethylene.
Adopt the method for from residual oil of vegetable fat deodorizing distillate, extracting natural phytosterin of technique scheme, gained natural phytosterin purity is higher than 90%, can meet the need of market, the yield of sterol reaches 5~40% of raw material residual oil, separated in the filtrate of sterol and contained a large amount of lipid acid, can be used for preparing tensio-active agent or biofuel, resistates then can be used as slushing oil.Technology of the present invention is simple, easy handling, controllability is good, cost is low, be easy to industrialization.The present invention makes vegetable fat deodorizing distillate reach the most effective comprehensive utilization; significantly reduced the discharging of waste residue, the protection environment not only has considerable economic worth; but also have crucial social effect, meet the state basic policy and the related industries policy of the present energy-saving and emission-reduction of China.
Description of drawings
Fig. 1 is the present invention extracts natural phytosterin from oil deodorization distillate residual oil a process flow sheet;
The infrared spectra of secondary crystal gained sterol product among Fig. 2 embodiment 6;
The gas-chromatography of secondary crystal gained sterol product among Fig. 3 embodiment 6.
Embodiment
The present invention is further illustrated below in conjunction with embodiment, and its purpose only is better to understand content of the present invention and unrestricted protection scope of the present invention:
Embodiment 1
1Kg soyabean deodorization distillate residual oil, 1000mL water are added in the reactor, be heated to 100 ℃, stir 60min the two is mixed, in reactor, add the 0.4Kg calcium oxide then, reacted 3 hours down at 100 ℃, add hydrochloric acid to be neutralized to pH=6, separate and remove lower aqueous layer.Oil phase is transferred in the cold analysis still, in oil phase, adds 1000mL ethanol then, be heated to 70 ℃, after being stirred to oil phase and dissolving fully, speed by 10 ℃/hour is lowered the temperature, and temperature-fall period keeps 1.5 rev/mins of stirring velocitys, forms as a large amount of tiny crystal grains, insulated and stirred 2 hours, and then continue cooling by 4 ℃/hour, when temperature reaches 15 ℃, stop to stir, keep 15 ℃ of temperature, slaking 6 hours.Subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with 1000mL ethanol, promptly gets thick sterol product after the drying.
Embodiment 2
1Kg rapeseed oil deodorization distillate residual oil, 500mL ethanol are added in the reactor, be heated to 70 ℃, stir 30min the two is mixed, in reactor, add 3Kg sodium hydroxide then, reacted 2 hours down at 80 ℃, add sulfuric acid to be neutralized to pH=1, separate and remove lower aqueous layer.Oil phase is transferred in the cold analysis still, in oil phase, adds the 1000mL sherwood oil then, be heated to 60 ℃, after being stirred to oil phase and dissolving fully, speed by 8 ℃/hour is lowered the temperature, and temperature-fall period keeps 1.5 rev/mins of stirring velocitys, forms as a large amount of tiny crystal grains, insulated and stirred 1 hour, and then continue cooling by 2 ℃/hour, when temperature reaches 5 ℃, stop to stir, keep 5 ℃ of temperature, slaking 12 hours.Subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with the 1000mL sherwood oil, promptly gets thick sterol product after the drying.
Embodiment 3
1Kg soybean oil deodorizer distillate residual oil, 750mL n-propyl alcohol are added in the reactor, be heated to 90 ℃, stir 30min the two is mixed, in reactor, add 0.3Kg potassium hydroxide then, reacted 5 hours down at 97 ℃, add sulfuric acid to be neutralized to pH=5, separate and remove lower aqueous layer.Oil phase is transferred in the cold analysis still, in oil phase, adds the listed organic solvent of 2500mL table 1 then, be heated to 60 ℃, after being stirred to oil phase and dissolving fully, speed by 5 ℃/hour is lowered the temperature, and temperature-fall period keeps 1.5 rev/mins of stirring velocitys, forms as a large amount of tiny crystal grains, insulated and stirred 1 hour, and then continue cooling by 1 ℃/hour, when temperature reaches 5 ℃, stop to stir, keep 5 ℃ of temperature, slaking 24 hours.Subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with the used organic solvent of 1000mL crystallization, promptly gets the thick product of sterol after the drying.Adopt the yield and the purity of the thick product of sterol that various organic solvent crystallizations go out as shown in table 1.
The yield and the purity of table 1 different organic solvents crystallization gained sterol
Sequence number | Organic solvent | Crystal color | Yield (%) | Sterol content (%) |
??1 | Ethanol | Slightly yellow | ??21.06 | ??89.56 |
??2 | Normal hexane | In vain | ??22.04 | ??92.90 |
??3 | Hexanaphthene | In vain | ??17.03 | ??92.88 |
??4 | Sherwood oil | Slightly yellow | ??22.37 | ??91.98 |
??5 | Acetone | Slightly yellow | ??19.16 | ??89.31 |
??6 | Ethyl acetate | In vain | ??21.53 | ??91.77 |
??7 | Acetone: ethanol=4: 1 (V/V) | Slightly yellow | ??21.87 | ??90.17 |
Embodiment 4
1Kg soybean oil deodorizer distillate residual oil, 500mL ethanol are added in the reactor, be heated to 78 ℃, stir 30min the two is mixed, in reactor, add 0.5Kg potassium hydroxide then, reacted 3 hours down at 78 ℃, add hydrochloric acid to be neutralized to pH=5, separate and remove lower aqueous layer.Oil phase is transferred in the cold analysis still, in oil phase, add the 4000mL sherwood oil then, be heated to 60 ℃, after being stirred to oil phase and dissolving fully, speed by 5 ℃/hour is lowered the temperature, temperature-fall period keeps 1.5 rev/mins of stirring velocitys, forms insulated and stirred 1 hour as a large amount of tiny crystal grains, and then by 1 ℃ of/hour continuation cooling, to the listed curing temperature of table 2, stop to stir insulation slaking 24 hours.Subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with 1000mL ethanol, promptly gets the thick product of sterol after the drying.The yield of the thick product of sterol that crystallization goes out under the different curing temperatures is as shown in table 2.
The yield of the thick product of sterol that crystallization goes out under the different curing temperatures of table 2
Sequence number | Curing temperature (℃) | The product color | Product yield |
??1 | ??30 | Very white | ??19.93% |
??2 | ??25 | Very white | ??18.84% |
??3 | ??20 | Very white | ??22.96% |
??4 | ??15 | Very white | ??23.70% |
??5 | ??10 | Very white | ??24.40% |
??6 | ??5 | Very white | ??23.52% |
??7 | ??0 | Very white | ??21.40% |
Embodiment 5
1Kg soybean oil deodorizer distillate residual oil, 500mL ethanol are added in the reactor, be heated to 78 ℃, stir 30min the two is mixed, in reactor, add 0.5Kg potassium hydroxide then, reacted 3 hours down at 78 ℃, add hydrochloric acid to be neutralized to pH=5, separate and remove lower aqueous layer.Oil phase is transferred in the cold analysis still, in oil phase, adds the 3000mL sherwood oil then, be heated to 60 ℃, after being stirred to oil phase and dissolving fully, speed by 5 ℃/hour is lowered the temperature, and temperature-fall period keeps 1.5 rev/mins of stirring velocitys, forms as a large amount of tiny crystal grains, insulated and stirred 1 hour, and then continue cooling by 1 ℃/hour, when temperature reaches 5 ℃, stop to stir, keep 10 ℃ of temperature, the listed difference of slaking table 3 hour.Subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with 1000mL ethanol, promptly gets the thick product of sterol after the drying.The yield of the thick product of sterol that crystallization goes out under the different curing temperatures is as shown in table 2.
The yield of the thick product of sterol that crystallization goes out under the different curing temperatures of table 3
Sequence number | Curing time (h) | The product color | Product yield |
??1 | ??4 | Slightly yellow | ??16.35% |
??2 | ??8 | Dark yellow | ??18.39% |
??3 | ??12 | Whiter | ??18.58% |
??4 | ??16 | In vain | ??19.22% |
??5 | ??20 | Very white | ??19.20% |
??6 | ??24 | Very white | ??18.84% |
??7 | ??28 | Very white | ??17.78% |
??8 | ??32 | Very white | ??18.89% |
Embodiment 6
1Kg soybean oil deodorizer distillate residual oil, 750mL n-propyl alcohol are added in the reactor, be heated to 78 ℃, stirring 30min mixes the two, in reactor, add 0.7Kg concentration then and be 40% potassium hydroxide aqueous solution, reacted 5 hours down at 78 ℃, add sulfuric acid and be neutralized to pH=3, separate and remove lower aqueous layer, add 1000mL water washing oil phase three times.Oil phase is transferred in the cold analysis still, in oil phase, adds the mixed solvent of 2500mL ethanol and acetone (V/V=1/4) then, be heated to 60 ℃, after being stirred to oil phase and dissolving fully, speed by 5 ℃/hour is lowered the temperature, and temperature-fall period keeps 1.5 rev/mins of stirring velocitys, forms as a large amount of tiny crystal grains, insulated and stirred 1 hour, and then continue cooling by 1 ℃/hour, when temperature reaches 5 ℃, stop to stir, keep 5 ℃ of temperature, slaking 24 hours.Subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with 1000mL ethanol, promptly gets primary crystallization sterol product after the drying, and through gas chromatographic detection, its purity is 90.69%; Gained primary crystallization sterol product is dissolved in 1000mL ethanol and acetone (V/V=1/4) mixed solvent, be heated to 60 ℃, after being stirred to dissolving fully, speed by 5 ℃/hour is lowered the temperature, temperature-fall period keeps 1 rev/min of stirring velocity, after temperature is reduced to 10 ℃, stop to stir, insulation slaking 12 hours, subsequently crystal solution is transferred to and carries out press filtration in the plate-and-frame filter press, filter cake divides 3 washings with 600mL ethanol, promptly gets secondary crystal sterol product after the drying, through gas chromatographic detection, its purity is 95.73%.Fig. 2 shows the infrared spectra of secondary crystal sterol product, and through contrasting with sterol standard spectrogram, the products obtained therefrom infrared spectrum is consistent with sterol standard spectrogram, does not find the existence of other impurity peaks; Fig. 3 shows the gas-chromatography of secondary crystal sterol product, is interior mark with cholesterol, retention time 12.89,13.78,14.25,15.22 peak is corresponding respectively brassicasterol, campesterol, Stigmasterol and β-Gu Zaichun.
Claims (7)
1, a kind of technology of extracting natural phytosterin from oil deodorization distillate residual oil is characterized in that this technological process is as follows:
(1) residual oil of vegetable fat deodorizing distillate, solvent are joined in the reactor, the mass ratio of residual oil and solvent is 1: 0.1~2, under agitation is heated to 60~100 ℃, and the two is mixed;
(2) catalyzer of adding residual oil weight 10%~80% in reactor, cartalytic decomposition effect is 1~10 hour under heated and stirred;
(3) after reaction is finished, be acidified with acid, separate then and remove water layer to pH=1~7;
(4) oil phase is transferred in the cold analysis tower, and adds the organic solvent of 2~6 times of quality of oil phase, be warming up to 50~90 ℃, under 50~150 rev/mins rotating speed, stir oil phase is dissolved fully;
(5) carry out dynamic gradient cooling crystallization with 5~10 ℃/hour, when a large amount of tiny crystal grains were separated out, stir speed (S.S.) transferred to 20~80 rev/mins, was incubated 0.25~5 hour, continued cooling by 1~4 ℃/hour afterwards;
(6) when temperature reaches-10~25 ℃ curing temperature scope, stop to stir and being incubated 4~48 hours;
(7) mixed solution after the crystallization is filtered or press filtration, and use organic solvent washing, promptly get the thick product of sterol;
(8) the thick product of sterol is dissolved in the organic solvent of 2~10 times of weight, being heated to 50~90 ℃ dissolves sterol fully, under 50~150 rev/mins rotating speed, carry out dynamic gradient cooling crystallization with 1~10 ℃/hour, when temperature reaches-10~25 ℃ curing temperature scope, stop to stir and being incubated 4~48 hours, then crystallization mixture is filtered or press filtration, and use organic solvent washing, promptly get the natural phytosterin product.
2, the technology of extracting natural phytosterin from oil deodorization distillate residual oil as claimed in claim 1 is characterized in that described oil deodorization distillate residual oil means in soybean oil, rapeseed oil, peanut oil, Rice pollard oil, sunflower seed oil, plam oil, numb maple oil or the sweet oil one or more the residual solution of deodorization distillate behind molecular distillation.
3, the technology of extracting natural phytosterin from oil deodorization distillate residual oil as claimed in claim 1 is characterized in that described solvent of (1) step is one or more in water, methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol or the isopropylcarbinol.
4, the technology of extracting natural phytosterin from oil deodorization distillate residual oil as claimed in claim 1 is characterized in that described catalyzer of (2) step is LiOH, NaOH, KOH, Ca (OH)
2, Na
2O, K
2O, CaO, CH
3ONa, C
2H
5ONa, K
2CO
3, Na
2CO
3, Li
2CO
3, in ammoniacal liquor or the magnesium aluminum-hydrotalcite one or more.
5, the technology of extracting natural phytosterin from oil deodorization distillate residual oil as claimed in claim 1 is characterized in that described temperature of reaction of (2) step is 60~120 ℃.
6, the technology of extracting natural phytosterin from oil deodorization distillate residual oil as claimed in claim 1 is characterized in that (3) described acid of step is one or more in sulfuric acid, hydrochloric acid, phosphoric acid or the Hydrogen bromide.
7, the technology of from oil deodorization distillate residual oil, extracting natural phytosterin as claimed in claim 1, it is characterized in that described organic solvent of (4), (7) and (8) step is methyl alcohol, ethanol, n-propyl alcohol, Virahol, propyl carbinol, isopropylcarbinol, acetone, butanone, pimelinketone, ethyl acetate, ethyl formate, one or more in methyl acetate, sherwood oil, normal hexane, hexanaphthene, Skellysolve A or the pentamethylene.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100692410A CN101607977B (en) | 2009-06-12 | 2009-06-12 | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2009100692410A CN101607977B (en) | 2009-06-12 | 2009-06-12 | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof |
Publications (2)
Publication Number | Publication Date |
---|---|
CN101607977A true CN101607977A (en) | 2009-12-23 |
CN101607977B CN101607977B (en) | 2011-06-29 |
Family
ID=41481895
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN2009100692410A Expired - Fee Related CN101607977B (en) | 2009-06-12 | 2009-06-12 | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN101607977B (en) |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107827947A (en) * | 2017-11-17 | 2018-03-23 | 浙江伊宝馨生物科技股份有限公司 | The method that high-purity sterol is extracted from the residual oil containing sterol ester |
CN109535214A (en) * | 2018-12-18 | 2019-03-29 | 湖南科瑞生物制药股份有限公司 | A method of preparing the bis- dehydrogenation -17a- hydroxyl progesterones of 1,6- |
CN109627276A (en) * | 2018-12-18 | 2019-04-16 | 湖南科瑞生物制药股份有限公司 | It is a kind of to prepare the bis- dehydrogenation -17a- hydroxyl progesterone method for product of 1,6- |
CN109627275A (en) * | 2018-12-18 | 2019-04-16 | 湖南科瑞生物制药股份有限公司 | A kind of bis- dehydrogenation -17a- hydroxyl progesterone product preparation methods of 1,6- |
CN110818762A (en) * | 2019-11-19 | 2020-02-21 | 福建省格兰尼生物工程股份有限公司 | Residual oil treatment method for recovering sterol and refining sylvite |
CN114450386A (en) * | 2019-09-27 | 2022-05-06 | 巴斯夫欧洲公司 | Process for the production of sterols and/or tocopherols and recovery of by-products |
CN114466856A (en) * | 2019-09-27 | 2022-05-10 | 巴斯夫欧洲公司 | Process for producing and purifying sterols |
CN114502568A (en) * | 2019-09-27 | 2022-05-13 | 巴斯夫欧洲公司 | Method for purifying phytosterols |
CN114605487A (en) * | 2022-04-08 | 2022-06-10 | 陕西海斯夫生物工程有限公司 | Method for separating erythrina sterol from olive pomace oil deodorization distillate |
CN114891055A (en) * | 2022-04-13 | 2022-08-12 | 福建省格兰尼生物工程股份有限公司 | Method for extracting sterol from plant residual oil by chemical and biological methods |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1283765C (en) * | 2003-03-19 | 2006-11-08 | 苏明华 | Method for producing biological clean fuel |
CN1634967A (en) * | 2003-12-30 | 2005-07-06 | 宁波大红鹰生物工程股份有限公司 | Sterol refining process |
CN1310903C (en) * | 2005-06-28 | 2007-04-18 | 中谷天科(天津)生物工程有限公司 | Method for extracting natural vitamin E from vegetable oil and fat refining and deodorizing distillate |
CN101331149A (en) * | 2005-11-08 | 2008-12-24 | 科学与工业研究会 | A process for the preparation of high purity phytosterols from deodourizer distillate from vegetable oils |
CN101153035B (en) * | 2007-10-19 | 2010-09-15 | 浙江工业大学 | Method for extracting vitamin E from vegetable oil deodorization distillate |
CN101412745B (en) * | 2008-11-27 | 2011-09-21 | 南京工业大学 | Improved process for extracting sterol from vegetable oil asphalt |
-
2009
- 2009-06-12 CN CN2009100692410A patent/CN101607977B/en not_active Expired - Fee Related
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107827947B (en) * | 2017-11-17 | 2020-03-10 | 浙江伊宝馨生物科技股份有限公司 | Method for extracting high-purity sterol from residual oil containing sterol ester |
CN107827947A (en) * | 2017-11-17 | 2018-03-23 | 浙江伊宝馨生物科技股份有限公司 | The method that high-purity sterol is extracted from the residual oil containing sterol ester |
CN109535214A (en) * | 2018-12-18 | 2019-03-29 | 湖南科瑞生物制药股份有限公司 | A method of preparing the bis- dehydrogenation -17a- hydroxyl progesterones of 1,6- |
CN109627276A (en) * | 2018-12-18 | 2019-04-16 | 湖南科瑞生物制药股份有限公司 | It is a kind of to prepare the bis- dehydrogenation -17a- hydroxyl progesterone method for product of 1,6- |
CN109627275A (en) * | 2018-12-18 | 2019-04-16 | 湖南科瑞生物制药股份有限公司 | A kind of bis- dehydrogenation -17a- hydroxyl progesterone product preparation methods of 1,6- |
CN114502568A (en) * | 2019-09-27 | 2022-05-13 | 巴斯夫欧洲公司 | Method for purifying phytosterols |
CN114450386A (en) * | 2019-09-27 | 2022-05-06 | 巴斯夫欧洲公司 | Process for the production of sterols and/or tocopherols and recovery of by-products |
CN114466856A (en) * | 2019-09-27 | 2022-05-10 | 巴斯夫欧洲公司 | Process for producing and purifying sterols |
CN111718391A (en) * | 2019-11-19 | 2020-09-29 | 福建省格兰尼生物工程股份有限公司 | Residual oil treatment method for recovering sterol |
CN110818762A (en) * | 2019-11-19 | 2020-02-21 | 福建省格兰尼生物工程股份有限公司 | Residual oil treatment method for recovering sterol and refining sylvite |
CN110818762B (en) * | 2019-11-19 | 2022-08-05 | 福建省格兰尼生物工程股份有限公司 | Residual oil treatment method for recovering sterol and refining sylvite |
CN114605487A (en) * | 2022-04-08 | 2022-06-10 | 陕西海斯夫生物工程有限公司 | Method for separating erythrina sterol from olive pomace oil deodorization distillate |
CN114605487B (en) * | 2022-04-08 | 2022-09-30 | 陕西海斯夫生物工程有限公司 | Method for separating erythrina sterol from olive pomace oil deodorization distillate |
CN114891055A (en) * | 2022-04-13 | 2022-08-12 | 福建省格兰尼生物工程股份有限公司 | Method for extracting sterol from plant residual oil by chemical and biological methods |
Also Published As
Publication number | Publication date |
---|---|
CN101607977B (en) | 2011-06-29 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN101607977B (en) | Method for extracting and purifying natural phytosterol from oil deodorization distillate residual oil and technique thereof | |
CN101701029B (en) | Method for extracting natural phytosterin from residual oil of vegetable fat deodorizing distillate | |
US5627289A (en) | Recovery of tocopherol and sterol from tocopherol and sterol containing mixtures of fats and fat derivatives | |
CN105016956B (en) | A kind of method for extracting squalene | |
CN101845362B (en) | Method for gathering oleic acid from tea-seed oil | |
CN106117297B (en) | The preparation method of one plant sterols and sterol ester | |
WO2007054759A1 (en) | A process for the preparation of high purity phytosterols from deodourizer distillate from vegetable oils | |
CN101851561A (en) | Method for co-producing biodiesel, phytosterol and tocopherol by using grease deodorized distillate | |
CN106977582A (en) | A kind of method of Hydrolysis kinetics phytosterol in deodorization distillate | |
CN103804337A (en) | Novel technology for extracting vitamin E and squalene by employing multi-stage counter-current liquid-liquid extraction method | |
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 | |
CN105132189B (en) | A kind of fine separation method of C18 series and C20~C22 series fatty acid methyl esters | |
CN101475622B (en) | Method for extracting phytosterin from residues after extracting vitamin E | |
CN102887821A (en) | Method for extracting DHA (docosahexaenoic acid) through extraction and separation of marine microalgae fermentation liquid | |
CN102352400B (en) | Method for producing phytosterol from deodorized distillate of vegetable fat obtained by microbial fermentation | |
CN104151282A (en) | Method for preparing natural vitamin E and phytosterol with resin absorption method | |
CN108774281B (en) | Method for extracting phytosterol from cottonseed acidified oil | |
CN106565454A (en) | Preparation method for conjugated linoleic acid | |
CN101709074B (en) | Crystallization method for separating and purifying sterol from vegetable oil deodorizer distillate | |
CN101412745B (en) | Improved process for extracting sterol from vegetable oil asphalt | |
CN107573237B (en) | Method for preparing high-purity gossypol acetate in cotton oil refining process | |
CN100334103C (en) | Method for extracting phytosterol acetate from plant oil asphalt | |
CN113588485B (en) | Method for extracting total unsaponifiable matter from vegetable oil | |
CN109609286A (en) | A method of extracting phytosterol from cottonseed acidification oil |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
C06 | Publication | ||
PB01 | Publication | ||
C10 | Entry into substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
C14 | Grant of patent or utility model | ||
GR01 | Patent grant | ||
CF01 | Termination of patent right due to non-payment of annual fee | ||
CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20110629 Termination date: 20170612 |