CN1356386A - Process for preparing conjugated linoleic acid from dewatered castor oil - Google Patents
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Abstract
A process for preparing conjugated linoleic acid from dewatered castor oil includes phisicochemically induced isomerizing, hydrolysis and multi-step separation. The resultant product contains conjugated linoleic acid (hgihter than 80%), linoleic acid (higher than 15%) and their isomer. It features its functions of preventing and treating cancer, diabetes and atherosclerosis, improving immunity, reducing blood sugar and fat, etc.
Description
Technical field
The present invention relates to a kind of method for preparing conjugated linolic acid by synourin oil
Background technology
Conjugated linolic acid (Conjngated Linoleic acid) is the mixture that contains a series of octadecadienoic acids of conjugated double bond, and these octadecadienoic acids exist configuration and conformation different isomer as 9-c, 11-c; 10-c, 12-c; 9-t, 11-t; 10-t, 12-t; 9-t, 11-c; 9-c, 11-t; 10-c, 12-t; 10-t, 12-c; In French cheese, found 8,10 and 11,13 isomer afterwards again.
Up to the present, discover 9-c, 11-t and 10-t, 12-c are two kinds of maximum isomer of content in the conjugated linolic acid, and its chemical structural formula is:
Through a large amount of animals and human research's evidence, conjugated linolic acid has anticancer, atherosclerosis, and the regulation and control metabolism increases muscle, reduces fat, and enhancing body immunizing power is slowed down the immunity system side reaction; Blood sugar regulation, anti-diabetic; Effect such as promote to grow.Can be widely used in foodstuff additive, drug additive and fodder additives.Therefore, according to relevant data at home and abroad, the method for preparing conjugated linolic acid is a lot, for example:
1, oleic acid vinyl carbinol dewatering (Americana, 1994, J.Am.Oil Chem Soc)
Oleic acid is the cis Octadec-9-enoic Acid, utilizes oleic acid to become superoxide under illumination condition, after the reduction 8 and the oleic acid vinyl carbinol of 11-hydroxyl, and then under the acid catalysis oleic acid vinyl carbinol is changed into conjugated linolic acid.
2, by the method (Americana, 1997, J.Am.OilChem Soc) of Viscotrol C synthesis of conjugated linoleic acid
Viscotrol C is in methylene dichloride and methanol solution, esterification takes place down in sodium and reflux conditions, obtain methyl ricinoleate through separation and purification, again methyl ricinoleate and Methanesulfonyl chloride are reacted the toluene solution that generates 12-first sulphur oxygen based oleic acid methyl esters, under refluxing, the catalysis with alkali DBU or DBN obtains 9-c, the 11-t conjugated linolic acid then.
3, utilize catalyst oleum lini isomerization method (U.S. Pat 5719301)
With the oleum lini is raw material, closing organometallicss such as ruthenium, iridic compound with chromium carbonyl, ferrocene, ten dicarbapentaborane is catalyzer, in the presence of auxiliarys such as formic acid and phase acidoid, unconjugated double bond is isomerizated into conjugated double bond, can obtain 80% conjugated linolic acid.
4, enzyme catalysis linolic acid isomerization method (European patent EP 0839897)
Utilize the microorganism in the mouse intestines, linoleate isomerase catalysis linolic acid contained in the Butyrivibrio fibrisolvens of ruminating animal transforms the △ of Butyrivibrio fibrisolvens
12-suitable-△
11Anti-isomerase can make linoleic acid plus linolenic acid change into c9, t11 conjugated linolic acid, c9, t11, c15 conjugate linolenic acid.
5, utilize milk-acid bacteria to prepare conjugated linolic acid (U.S. Pat 5856149)
Milk-acid bacteria is a kind of microorganism relatively cheap, that cultivate and use easily, utilizes the linoleate isomerase that contains in the lactobacillus microorganism can produce conjugated linolic acid during the fermentation and extract conjugated linolic acid then from cell culture fluid.
6, linolic acid and Flos Carthami oil alkali isomerization (U.S. Pat 5760082)
Linolic acid or Thistle oil are dissolved in the organic solvent, under nitrogen protection and highly basic effect, make linolic acid generation isomerization, obtain conjugated linolic acid.
7, the method (U.S. Pat 5892074) for preparing conjugated linolic acid under the room temperature
Methyl ricinoleate and toluene sulfonyl chloride are reacted generation methyl ricinoleate tosylate or generate the methyl ricinoleate methanesulfonates in pyridine solvent or in acetonitrile and triethylamine, then methyl ricinoleate tosylate or methyl ricinoleate methanesulfonates are reacted in the non-hydroxyl solvent of acetonitrile and obtain 9-c, the 11-t conjugated linolic acid.
8, by the method that contains linolic acid material synthesis of conjugated linoleic acid (U.S. Pat 5986116)
To contain linoleic material as: Thistle oil, sunflower oil, Semen Maydis oil, soybean oil, oleum gossypii seminis, oleum lini, Wheat germ oils carry out isomerization and produce conjugated linolic acid under highly basic.
In many prior arts, some method steps is more numerous and diverse, some method implementation condition harshness, and the cost costliness is difficult to carry out large-scale production.And compared with the prior art the present invention has tangible difference.The present invention is to be raw material with synourin oil, can obtain being mainly 9-c, 11-t through inducing isomerization, hydrolysis, multistep to separate the operation of three steps; 10-t, 12-c target product conjugated linolic acid.
Summary of the invention
The object of the invention is, development prepares the method for conjugated linolic acid by synourin oil, is to be raw material with synourin oil, and adopts physicochemical method to induce isomerization, hydrolysis, multistep to separate the operation of three steps can to obtain being mainly 9-c, 11-t; 10-t, 12-c target product conjugated linolic acid, cla levels in the product 〉=80%, linoleic acid content 〉=15% contains a small amount of other conjugated linoleic acid isomers.Through a large amount of animal and human research's evidence, the products therefrom conjugated linolic acid has anticancer, atherosclerosis, and the regulation and control metabolism increases muscle, reduces fat, and enhancing body immunizing power is slowed down the immunity system side reaction; Blood sugar regulation, anti-diabetic; Effect such as promote to grow.Can be widely used in foodstuff additive, drug additive and fodder additives.This method suitability for industrialized production compared with prior art preferably, cost is low, owing to do not contain noxious solvent in its composition, therefore more safe and reliable to people, animal.
Of the present inventionly prepare the method for conjugated linolic acid by synourin oil, this method is to be raw material with synourin oil, adopts to induce isomerization, hydrolysis to separate with multistep to make, and concrete steps are pressed example and carried out:
Induce isomerization reaction
A, propylene glycol or ethylene glycol or methyl-sulphoxide or nitrogen dimethylformamide 200-600 gram and highly basic potassium hydroxide or sodium hydroxide 100-300 gram mixed place reaction vessel; under mechanical stirring, blast nitrogen protection and be heated to 150-170 ℃; churning time 15-30 minute; 200-400 being restrained synourin oil adds again; be warming up to 175-190 ℃; drop to room temperature in nitrogen protection, it is standby to obtain alternative.
B, a part of alternative charged into nitrogen under airtight after in 60 times irradiations of cobalt, absorption dose 1-40 kilogray (kGy).
C, place microwave oven to heat another part alternative, time 0.5-8 minute.
Hydrolysis reaction: with the reaction that is hydrolyzed respectively of b, c gained alternative
D, b, c gained alternative are put into reaction vessel respectively; nitrogen protection under mechanical stirring respectively; be heated to 180 ℃ of sustained reactions 2.5 hours; be cooled to room temperature; adding the 180ml concentrated hydrochloric acid stirred 20 minutes; adjust PH=2-4; reduce to room temperature after hydrolysis finishes, leave standstill that branch anhydrates and glycerine, wash 5-6 time then; be washed till PH=6.5-7.5; elder generation's sedimentation divides water, separates organic phase and water with whizzer again, and the organic phase that separation obtains is stand-by; the organic phase that wherein obtains is mainly conjugated linolic acid, and all the other are linolic acid, oleic acid.
E, with organic phase and C
1-C
5Low-carbon alcohol, glycerine under acid or base catalysis, can obtain corresponding conjugated linolic acid ester of low-carbon alcohol and monoglyceride or triglyceride or triglyceride level.
Multistep is separated: b, c gained alternative are hydrolyzed carry out multistep respectively again after the reaction and separate
F, get 600-800 gram methyl alcohol and mixes with 200-300 gram urea, heating makes it to dissolve, and the organic phase that separation is obtained is preheating in the 40-50 ℃ of adding urea mixed solution, fully stirs postcooling to 8-12 ℃ of suction filtration, and filtrate is stand-by.
G, with gained filtrate with the 0.5-2% charcoal absorption after-filtration of weight percentage, wash 2-3 time, branch vibration layer, carry out freezing and crystallizing, initial stage frozen cooling speed is 2-5 ℃/hour, when temperature reaches 0 ℃, regulating cooling rate is 7-10 ℃/hour, when temperature reduce to-7--9 ℃ after the freezing 20-40 of constant temperature hour, the crystallisate elimination can be obtained respectively 〉=80% conjugated linolic acid product with suction method, all the other are oleic acid, stearic acid, palmitinic acid and longer chain fatty acid, the recyclable oleic acid of crystallisate.
Embodiment
Embodiment 1
Induce isomerization reaction
A, propylene glycol 200 gram and highly basic potassium hydroxide 150 grams are mixed place reaction vessel; under mechanical stirring, blast nitrogen protection and be heated to 150 ℃; churning time 15-30 minute; again 200 gram synourin oils are added; be warming up to 175 ℃; drop to room temperature in nitrogen protection, it is standby to obtain alternative.
B, a part of alternative charged into nitrogen under airtight after in 60 times irradiations of cobalt, absorption dose 1-40 kilogray (kGy).
C, place microwave oven to heat another part alternative, time 0.5-8 minute.
Hydrolysis reaction: with the reaction that is hydrolyzed respectively of b, c gained alternative
D, b, c gained alternative are put into reaction vessel respectively; nitrogen protection under mechanical stirring respectively; be heated to 180 ℃ of sustained reactions 2.5 hours; be cooled to room temperature; adding the 180ml concentrated hydrochloric acid stirred 20 minutes; adjust PH=2-4; reduce to room temperature after hydrolysis finishes, leave standstill that branch anhydrates and glycerine, wash 5-6 time then; be washed till PH=6.5-7.5; elder generation's sedimentation divides water, separates organic phase and water with whizzer again, and the organic phase that separation obtains is stand-by; the organic phase that wherein obtains is mainly conjugated linolic acid, and all the other are linolic acid, oleic acid.
E, with organic phase and C
1-C
5Low-carbon alcohol, glycerine under acid or base catalysis, can obtain corresponding conjugated linolic acid ester of low-carbon alcohol and monoglyceride or triglyceride or triglyceride level.
Multistep is separated: b, c gained alternative are hydrolyzed carry out multistep respectively again after the reaction and separate
F, get 600 gram methyl alcohol and mixes with 200 gram urea, heating makes it to dissolve, and the organic phase that separation is obtained is preheating in the 40-50 ℃ of adding urea mixed solution, fully stirs postcooling to 8-12 ℃ of suction filtration, and filtrate is stand-by.
G, with gained filtrate with 0.5% charcoal absorption after-filtration of weight percentage, wash 2-3 time, branch vibration layer, carry out freezing and crystallizing, initial stage frozen cooling speed is 2-5 ℃/hour, when temperature reaches 0 ℃, regulating cooling rate is 7-10 ℃/hour, when temperature reduce to-7--9 ℃ after the freezing 20-40 of constant temperature hour, the crystallisate elimination can be obtained respectively 〉=80% conjugated linolic acid product with suction method, all the other are oleic acid, stearic acid, palmitinic acid and longer chain fatty acid, the recyclable oleic acid of crystallisate.
Embodiment 2
Induce isomerization reaction
A, methyl-sulphoxide 350 gram and highly basic sodium hydroxide 100 grams are mixed place reaction vessel; under mechanical stirring, blast nitrogen protection and be heated to 160 ℃; churning time 15-30 minute; again 300 gram synourin oils are added; be warming up to 180 ℃; drop to room temperature in nitrogen protection, it is standby to obtain alternative.
B, a part of alternative charged into nitrogen under airtight after in 60 times irradiations of cobalt, absorption dose 1-40 kilogray (kGy).
C, place microwave oven to heat another part alternative, time 0.5-8 minute.
Hydrolysis reaction: with the reaction that is hydrolyzed respectively of b, c gained alternative
D, b, c gained alternative are put into reaction vessel respectively; nitrogen protection under mechanical stirring respectively; be heated to 180 ℃ of sustained reactions 2.5 hours; be cooled to room temperature; adding the 180ml concentrated hydrochloric acid stirred 20 minutes; adjust PH=2-4; reduce to room temperature after hydrolysis finishes, leave standstill that branch anhydrates and glycerine, wash 5-6 time then; be washed till PH=6.5-7.5; elder generation's sedimentation divides water, separates organic phase and water with whizzer again, and the organic phase that separation obtains is stand-by; the organic phase that wherein obtains is mainly conjugated linolic acid, and all the other are linolic acid, oleic acid.
E, with organic phase and C
1-C
5Low-carbon alcohol, glycerine under acid or base catalysis, can obtain corresponding conjugated linolic acid ester of low-carbon alcohol and monoglyceride or triglyceride or triglyceride level.
Multistep is separated: b, c gained alternative are hydrolyzed carry out multistep respectively again after the reaction and separate
F, get 700 gram methyl alcohol and mixes with 250 gram urea, heating makes it to dissolve, and the organic phase that separation is obtained is preheating in the 40-50 ℃ of adding urea mixed solution, fully stirs postcooling to 8-12 ℃ of suction filtration, and filtrate is stand-by.
G, with gained filtrate with 1.0% charcoal absorption after-filtration of weight percentage, wash 2-3 time, branch vibration layer, carry out freezing and crystallizing, initial stage frozen cooling speed is 2-5 ℃/hour, when temperature reaches 0 ℃, regulating cooling rate is 7-10 ℃/hour, when temperature reduce to-7--9 ℃ after the freezing 20-40 of constant temperature hour, the crystallisate elimination can be obtained respectively 〉=80% conjugated linolic acid product with suction method, all the other are oleic acid, stearic acid, palmitinic acid and longer chain fatty acid, the recyclable oleic acid of crystallisate.
Embodiment 3
Induce isomerization reaction
A, nitrogen dimethylformamide 600 gram and highly basic potassium hydroxide 300 grams are mixed place reaction vessel; under mechanical stirring, blast nitrogen protection and be heated to 170 ℃; churning time 15-30 minute; again 400 gram synourin oils are added; be warming up to 190 ℃; drop to room temperature in nitrogen protection, it is standby to obtain alternative.
B, a part of alternative charged into nitrogen under airtight after in 60 times irradiations of cobalt, absorption dose 1-40 kilogray (kGy).
C, place microwave oven to heat another part alternative, time 0.5-8 minute.
Hydrolysis reaction: with the reaction that is hydrolyzed respectively of b, c gained alternative
D, b, c gained alternative are put into reaction vessel respectively; nitrogen protection under mechanical stirring respectively; be heated to 180 ℃ of sustained reactions 2.5 hours; be cooled to room temperature; adding the 180ml concentrated hydrochloric acid stirred 20 minutes; adjust PH=2-4; reduce to room temperature after hydrolysis finishes, leave standstill that branch anhydrates and glycerine, wash 5-6 time then; be washed till PH=6.5-7.5; elder generation's sedimentation divides water, separates organic phase and water with whizzer again, and the organic phase that separation obtains is stand-by; the organic phase that wherein obtains is mainly conjugated linolic acid, and all the other are linolic acid, oleic acid.
E, with organic phase and C
1-C
5Low-carbon alcohol, glycerine under acid or base catalysis, can obtain corresponding conjugated linolic acid ester of low-carbon alcohol and monoglyceride or triglyceride or triglyceride level.
Multistep is separated: b, c gained alternative are hydrolyzed carry out multistep respectively again after the reaction and separate
F, get 750 gram methyl alcohol and mixes with 300 gram urea, heating makes it to dissolve, and the organic phase that separation is obtained is preheating in the 40-50 ℃ of adding urea mixed solution, fully stirs postcooling to 8-12 ℃ of suction filtration, and filtrate is stand-by.
G, with gained filtrate with 1.5% charcoal absorption after-filtration of weight percentage, wash 2-3 time, branch vibration layer, carry out freezing and crystallizing, initial stage frozen cooling speed is 2-5 ℃/hour, when temperature reaches 0 ℃, regulating cooling rate is 7-10 ℃/hour, when temperature reduce to-7--9 ℃ after the freezing 20-40 of constant temperature hour, the crystallisate elimination can be obtained respectively 〉=80% conjugated linolic acid product with suction method, all the other are oleic acid, stearic acid, palmitinic acid and longer chain fatty acid, the recyclable oleic acid of crystallisate.
Embodiment 4
Induce isomerization reaction
A, ethylene glycol 250 gram and highly basic sodium hydroxide 200 grams are mixed place reaction vessel; under mechanical stirring, blast nitrogen protection and be heated to 160 ℃; churning time 15-30 minute; again 250 gram synourin oils are added; be warming up to 180 ℃; drop to room temperature in nitrogen protection, it is standby to obtain alternative.
B, a part of alternative charged into nitrogen under airtight after in 60 times irradiations of cobalt, absorption dose 1-40 kilogray (kGy).
C, place microwave oven to heat another part alternative, time 0.5-8 minute.
Hydrolysis reaction: with the reaction that is hydrolyzed respectively of b, c gained alternative
D, b, c gained alternative are put into reaction vessel respectively; nitrogen protection under mechanical stirring respectively; be heated to 180 ℃ of sustained reactions 2.5 hours; be cooled to room temperature; adding the 180ml concentrated hydrochloric acid stirred 20 minutes; adjust PH=2-4; reduce to room temperature after hydrolysis finishes, leave standstill that branch anhydrates and glycerine, wash 5-6 time then; be washed till PH=6.5-7.5; elder generation's sedimentation divides water, separates organic phase and water with whizzer again, and the organic phase that separation obtains is stand-by; the organic phase that wherein obtains is mainly conjugated linolic acid, and all the other are linolic acid, oleic acid.
E, with organic phase and C
1-C
5Low-carbon alcohol, glycerine under acid or base catalysis, can obtain corresponding conjugated linolic acid ester of low-carbon alcohol and monoglyceride or triglyceride or triglyceride level.
Multistep is separated: b, c gained alternative are hydrolyzed carry out multistep respectively again after the reaction and separate
F, get 650 gram methyl alcohol and mixes with 250 gram urea, heating makes it to dissolve, and the organic phase that separation is obtained is preheating in the 40-50 ℃ of adding urea mixed solution, fully stirs postcooling to 8-12 ℃ of suction filtration, and filtrate is stand-by.
G, with gained filtrate with 2% charcoal absorption after-filtration of weight percentage, wash 2-3 time, branch vibration layer carries out freezing and crystallizing, and initial stage frozen cooling speed is 2-5 ℃/hour, when temperature reaches 0 ℃, regulating cooling rate is 7-10 ℃/hour, when temperature reduce to-7--9 ℃ after the freezing 20-40 of constant temperature hour, the crystallisate elimination can be obtained respectively 〉=80% conjugated linolic acid product with suction method, all the other are oleic acid, stearic acid, palmitinic acid and longer chain fatty acid, the recyclable oleic acid of crystallisate.
Claims (1)
1, a kind ofly prepare the method for conjugated linolic acid by synourin oil, it is characterized in that this method is to be raw material with synourin oil, adopt and induce isomerization, hydrolysis to separate with multistep to make, concrete steps are pressed example and are carried out:
Induce isomerization reaction
A, propylene glycol or ethylene glycol or methyl-sulphoxide or nitrogen dimethylformamide 200-600 gram and highly basic potassium hydroxide or sodium hydroxide 100-300 gram mixed place reaction vessel; under mechanical stirring, blast nitrogen protection and be heated to 150-170 ℃; churning time 15-30 minute; 200-400 being restrained synourin oil adds again; be warming up to 175-190 ℃; drop to room temperature in nitrogen protection, it is standby to obtain alternative.
B, a part of alternative charged into nitrogen under airtight after in 60 times irradiations of cobalt, absorption dose 1-40 kilogray (kGy).
C, place microwave oven to heat another part alternative, time 0.5-8 minute.
Hydrolysis reaction: with the reaction that is hydrolyzed respectively of b, c gained alternative
D, b, c gained alternative are put into reaction vessel respectively; nitrogen protection under mechanical stirring respectively; be heated to 180 ℃ of sustained reactions 2.5 hours; be cooled to room temperature; adding the 180ml concentrated hydrochloric acid stirred 20 minutes; adjust PH=2-4; reduce to room temperature after hydrolysis finishes, leave standstill that branch anhydrates and glycerine, wash 5-6 time then; be washed till PH=6.5-7.5; elder generation's sedimentation divides water, separates organic phase and water with whizzer again, and the organic phase that separation obtains is stand-by; the organic phase that wherein obtains is mainly conjugated linolic acid, and all the other are linolic acid, oleic acid.
E, with organic phase and C
1-C
5Low-carbon alcohol, glycerine under acid or base catalysis, can obtain corresponding conjugated linolic acid ester of low-carbon alcohol and monoglyceride or triglyceride or triglyceride level.
Multistep is separated: b, c gained alternative are hydrolyzed carry out multistep respectively again after the reaction and separate
F, get 600-800 gram methyl alcohol and mixes with 200-300 gram urea, heating makes it to dissolve, and the organic phase that separation is obtained is preheating in the 40-50 ℃ of adding urea mixed solution, fully stirs postcooling to 8-12 ℃ of suction filtration, and filtrate is stand-by.
G, with gained filtrate with the 0.5-2% charcoal absorption after-filtration of weight percentage, wash 2-3 time, branch vibration layer carries out freezing and crystallizing, and initial stage frozen cooling speed is 2-5 ℃/hour, when temperature reaches 0 ℃, regulating cooling rate is 7-10 ℃/hour, when temperature reduce to-7--9 ℃ after the freezing 20-40 of constant temperature hour, the crystallisate elimination can be obtained 〉=80% conjugated linolic acid product with suction method, all the other are oleic acid, stearic acid, palmitinic acid and longer chain fatty acid, the recyclable oleic acid of crystallisate.
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| CNB011413026A CN1137975C (en) | 2001-09-25 | 2001-09-25 | Process for preparing conjugated linoleic acid from dewatered castor oil |
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|---|---|---|---|
| CNB011413026A CN1137975C (en) | 2001-09-25 | 2001-09-25 | Process for preparing conjugated linoleic acid from dewatered castor oil |
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| CN1137975C CN1137975C (en) | 2004-02-11 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1303054C (en) * | 2003-04-25 | 2007-03-07 | 日新Wells株式会社 | High purity diglyceride containing conjugated linoleic acid and preparation method thereof |
| CN100369881C (en) * | 2006-01-13 | 2008-02-20 | 国家***第一海洋研究所 | High-content 9,11 conjugated linoleic acid composition and preparation method thereof |
| CN101781187A (en) * | 2010-02-10 | 2010-07-21 | 江西省粮油科学技术研究所 | Method for preparing conjugated linoleic acid by solid base catalysis |
| CN101050172B (en) * | 2006-04-07 | 2010-09-22 | 天津科技大学 | Method for preparing conjugation linoleic acid by intermittent type microwave action |
| CN104087425A (en) * | 2014-07-08 | 2014-10-08 | 龚旌 | Preparation method of low-cost conjugated linoleic acid |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006106809A1 (en) * | 2005-03-30 | 2006-10-12 | The Nisshin Oillio Group, Ltd. | Method for producing concentrate of conjugated fatty acid |
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2001
- 2001-09-25 CN CNB011413026A patent/CN1137975C/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1303054C (en) * | 2003-04-25 | 2007-03-07 | 日新Wells株式会社 | High purity diglyceride containing conjugated linoleic acid and preparation method thereof |
| CN100369881C (en) * | 2006-01-13 | 2008-02-20 | 国家***第一海洋研究所 | High-content 9,11 conjugated linoleic acid composition and preparation method thereof |
| CN101050172B (en) * | 2006-04-07 | 2010-09-22 | 天津科技大学 | Method for preparing conjugation linoleic acid by intermittent type microwave action |
| CN101781187A (en) * | 2010-02-10 | 2010-07-21 | 江西省粮油科学技术研究所 | Method for preparing conjugated linoleic acid by solid base catalysis |
| CN101781187B (en) * | 2010-02-10 | 2013-04-17 | 江西省粮油科学技术研究所 | Method for preparing conjugated linoleic acid by solid base catalysis |
| CN104087425A (en) * | 2014-07-08 | 2014-10-08 | 龚旌 | Preparation method of low-cost conjugated linoleic acid |
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