CN106565454A - Preparation method for conjugated linoleic acid - Google Patents
Preparation method for conjugated linoleic acid Download PDFInfo
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- CN106565454A CN106565454A CN201610915492.6A CN201610915492A CN106565454A CN 106565454 A CN106565454 A CN 106565454A CN 201610915492 A CN201610915492 A CN 201610915492A CN 106565454 A CN106565454 A CN 106565454A
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- linoleic acid
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
- C07C51/44—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
Abstract
The invention discloses a preparation method for conjugated linoleic acid. The preparation method comprises the following steps that linoleic acid alkyl ester and a basic catalyst are subjected to solvent-free isomerization reaction; a reagent is added into a base solution to be subjected to saponification, and a conjugated linoleic acid soap is obtained; the conjugated linoleic acid soap is acidized with the pH value being 1-2 and then subjected to liquid separation, and an oil layer is obtained through separation and washed with water; and the oil layer is subjected to decolorization and purification, and after solvents are removed, the conjugated linoleic acid is obtained. According to the preparation method for the conjugated linoleic acid, the linoleic acid alkyl ester is selected as a raw material, consumption of the basic catalyst is reduced, and solvent-free direct reaction is adopted; meanwhile, the content requirement for the conjugated linoleic acid can be met at the lower reaction temperature, so that energy sources and the raw material are further saved; and in addition, vegetable oil rich in the linoleic acid alkyl ester is adopted, the source of the raw material is enriched, dependency on safflower oil is reduced, accordingly, the production cost is effectively reduced, and the quite high practicability is achieved.
Description
Technical field
The present invention relates to the separation preparation field of industrial chemicals, more particularly to a kind of preparation method of conjugated linoleic acid.
Background technology
Conjugated linoleic acid (CLA) is that a series of positions in 9,11 or 10,12 linoleic acids (LA) with double bond of carbon are different
The general name of structure body and steric isomer.Research shows that CLA has to be reduced cholesterol, improves immunologic function, suppresses tumor, anti-tremulous pulse
The physiological function such as atherosis.Meanwhile, related also document report, CLA can suppress the fat of fatty tissue to synthesize and strengthen fat decomposition
Cause, reduce body fat, especially stomach fat.Therefore, different with other Long carbon chain satisfied fatty acid, conjugated linoleic acid can
To be absorbed by the body as a kind of special functional fatty acid, promote steatolysiss by way of changing lipid metabolism, from
And reach the purpose of fat-reducing.Therefore either as medicine, health food, functional food, food preservative, or in meat work
In industry, feed industry, CLA has broad application prospects and market potential.
Natural conjugated linoleic acid is primarily present in the butterfat and milk product, meat productss of cud animal cattle, sheep etc., is also existed
Exist in human milk fat.But natural conjugated linoleic acid limited source, and quantity is few, it is industrial at present to be mainly to be rich in
Linoleic acid vegetable oil is reacted by alkalicatalyzed conjugation and saponification is obtained conjugated linoleic acid.
For the highly active conjugated linoleic acid of synthesis of high purity, such a way in prior art, is taken：
Chinese patent application (publication date：June 14, publication number in 2006：CN1785953A, in), produce conjugated linoleic acid
Method reaction temperature more than 160 DEG C, and the large usage quantity of catalysts and solvents.In patent, the conversion ratio of conjugated linoleic acid is
Between 76%～95%, even if do not generate other isomers completely according to 95% conversion ratio calculate simultaneously, raw material linoleic acid contains
Amount needs access to 80%, and ingredient requirement is high, and range of application is narrow.
United States Patent (USP) (publication date：November 23, publication number in 2004：US6822104B2) disclose a kind of sub- oil of conjugation
The preparation method of acid, so that as raw material, high boiling point Polyethylene Glycol is solvent, is entered under the catalysis of highly basic rich in linoleic vegetable oil
Row conjugative reaction, obtains conjugated linoleic acid after acidifying.In addition the method reaction temperature height, soda acid consumption are big, difficult solvent recovery,
And the conjugated linoleic acid obtained by technique is difficult to the requirement that reaches quality standards.
United States Patent (USP) (publication date：November 6, publication number in 1999：US5986116A) disclose a kind of conjugated linoleic acid
Preparation method, with Propylene Glycol as solvent, alkali used can be the nothings such as potassium hydroxide, sodium hydroxide and Cesium hydrate. to the method
The reaction conditions such as the sodium alkoxide such as machine alkali, or Feldalat NM, Sodium ethylate or tetraethyl ammonium hydroxide organic base, temperature and time will
Affect linoleic acid rate and product isomer proportion of composing.When there is isomerization reaction for 110 DEG C, linoleic acid turns safflower oil
Rate is 26.5%, is 78.2% at 130 DEG C；When reaction temperature rises to 170 DEG C, conversion ratio is up to 99.1%.Although the method
Can prepare the conjugated linoleic acid of high conversion, but the method needs to consume substantial amounts of alkali and carries out isomerization reaction, this
Also use the organic solvents such as Propylene Glycol outward, cause follow-up difficult solvent recovery, three waste discharge is big.
Ministry of Health of the People's Republic of China's No. 12 bulletin approval conjugated linoleic acid in 2009 is new resource food, to conjugation
Linoleic prescription has carried out detailed regulation, it is desirable to which in product, cla levels are 78%～84%, wherein 9c,
Two kinds of content of isomer of 11t and 10t, 12c are required and reach 37.5%～42%, C18:2 9c, 12c are less than 3%, and alltranses are different
Structure body content is less than 1%.The production technology reported at present is difficult to reach whole requirements, can send out from above prior art content
It is existing, mixed with any ratio if making catalyst using sodium hydroxide/potassium hydroxide with water or solvent in prior art, with Flos Carthami
Oil triglycerides are raw material, and reaction is generally needed at 150 DEG C～230 DEG C, while the shortcoming of high temperature is transisomer 9c, 11t
Conjugated linoleic acid and 10t, 12c cla levels are often higher, in addition using ethylene glycol or Propylene Glycol as solvent, product
There is the risk for generating conjugated linoleic acid ethylene glycol or Propylene Glycol again.
Can to sum up see, although alkali isomerization prepares CLA simply, in place of also there are some shortcomings, with plant Phyllanthus emblica L.
Oily three esters need to consume substantial amounts of alkali for the process for preparing conjugated linoleic acid of raw material, need then to consume more substantial solvent
Guarantee the mass transfer of reaction system.At present industrial common solvent is ethylene glycol, glycerol, Propylene Glycol and Polyethylene Glycol etc. mostly, these
Solvent is respectively provided with higher boiling point.On the one hand, solvent separates relatively difficult with product, causes the purity of product not high, and
Some solvents such as the ethylene glycol, Propylene Glycol of residual has certain toxicity, and has and generate conjugated linoleic acid ethylene glycol or the third two
The risk of alcohol ester, limits application of the product in medicine and field of food；On the other hand, with vegetable oil triglycerides as raw material
When, byproduct of reaction glycerol is difficult to be separated with solvent, causes difficult solvent recovery, and glycerol and its derivant presence to lead
Cause isomerization operation to have the risk for producing trimethoxypropane gave or triethoxy propane, affect the purity of product.
All in all, the preparation technology of current conjugated linoleic acid has certain deficiency, is mainly manifested in following several
Individual aspect：1) raw material dependency is strong.Need with the vegetable oil of high linoleic acid such as safflower oil as raw material production.2) transisomer contains
Amount is high.As isomerization reaction temperature is higher, alltranses conjugated linoleic acid is easily produced, trans body content will more than quality standard
1% for asking.3) alkali consumption is big, and solvent applies mechanically difficulty.Conjugative reaction needs to use a large amount of base catalysiss in organic solvent, causes three
Useless discharge is big.
The content of the invention
Present invention aim to provide a kind of preparation method of conjugated linoleic acid, the method with linoleic acid Arrcostab is
Raw material, prepares conjugated linoleic acid by Direct Isomerization and saponification, and low cost, side reaction are few, product purity is high, are suitable for
In industrialized production.
For achieving the above object, the technical solution used in the present invention is：
A kind of preparation method of conjugated linoleic acid, the preparation method of the conjugated linoleic acid comprise the steps：
1) linoleic acid Arrcostab and base catalyst are carried out into solvent-free isomerization reaction at 100 DEG C～140 DEG C, is reacted
Time 2h～6h；
2) by step 1) in reactant be added in aqueous alkali and carry out saponification and obtain conjugated linoleic acid soap；
3) by step 2) in conjugated linoleic acid soap be acidified to pH value to carry out the isolated oil reservoir of point liquid, and water after 1～2
Washing oil layer；
4) by step 3) in oil reservoir carry out decolouring purification, and after removing solvent, obtain the conjugated linoleic acid.
Preferably, the linoleic acid Arrcostab be by Oleum Vitis viniferae, safflower oil, Semen Maydis oil, soybean oil, Oleum Helianthi,
The crude oil or refined oil of one or more in Oleum Gossypii semen, and its derivant obtained after purification.This area it is general
Logical technical staff, according to known oils and fatss Linoleic acid content, with reference to known related purification technique purification to content be
80%～99%, it is also possible to directly buy linoleic acid Arrcostab.Linoleic acid Arrcostab is more preferably methyl linoleate or linoleic acid
Ethyl ester.
It is furthermore preferred that the derivant is Oleum Vitis viniferae, safflower oil, Semen Maydis oil, soybean oil, Oleum Helianthi, Oleum Gossypii semen
In one or more Fructus Gleditsia, acidification oil or deodorization distillate.
Preferably, the step (1) is carried out under nitrogen protection.It is preferred that nitrogen is replaced to reaction vessel first before the reaction
Gas.
Preferably, during the base catalyst in the step (1) is Feldalat NM, Sodium ethylate, Feldalat KM or potassium ethoxide
One kind, its consumption for linoleic acid Arrcostab quality 2%～8%.
Preferably, in the step (2), aqueous alkali is NaOH aqueous solutions that mass concentration is 10%～40% or KOH water
Solution, saponification are 1～8h of reaction at 60 DEG C～100 DEG C.It is furthermore preferred that saponification is reacted at 70 DEG C～90 DEG C
1～4h.The extent of reaction of the saponification, it is anti-to saponification that those skilled in the art can adopt conventional means to be tracked
Should terminate.
Preferably, the acidifying in the step (3) is carried out at 70 DEG C～90 DEG C.
Preferably, the washing in the step (3) refers to that oil reservoir divides and removes water successively with sour water, pure water to neutrality
Layer, and oil reservoir is dried.
Preferably, the decolouring purification in the step (4) refers to that oil reservoir adds linoleic acid Arrcostab quality 1% after washing
～10% activated carbon, at 90 DEG C～110 DEG C, decoloring reaction 0.5h～1h under vacuum condition, then filtered while hot decolourized
Filtrate after purification.
Preferably, the removing solvent in the step (4) refers to, by the filtrate decolourized after purification at 160 DEG C～180 DEG C,
Molecular distillation is carried out under the conditions of 1Pa～10Pa and removes solvent.
Currently preferred technical scheme is：
A kind of preparation method of conjugated linoleic acid, the preparation method of the conjugated linoleic acid comprise the steps：
1) under nitrogen protection, linoleic acid Arrcostab and base catalyst are carried out at 100 DEG C～140 DEG C solvent-free different
Structureization is reacted, response time 2h～6h；
2) by step 1) in reactant be added to the NaOH aqueous solutions or KOH aqueous solutions that mass concentration is 10%～40%
In carry out saponification and obtain conjugated linoleic acid soap, saponification is 1～4h of reaction at 70 DEG C～90 DEG C；
3) by step 2 at 70 DEG C～90 DEG C) in conjugated linoleic acid soap be acidified to pH value and divide to carry out point liquid after 1～2
From oil reservoir is obtained, oil reservoir uses sour water, pure water to neutrality, branch vibration layer successively, and oil reservoir is dried；
4) by step 3) in oil reservoir add the activated carbon of linoleic acid Arrcostab quality 1%～10%, 90 DEG C～110
DEG C, decoloring reaction 0.5h～1h under vacuum condition, then filtered while hot obtain the filtrate decolourized after purification, and after removing solvent
Obtain the conjugated linoleic acid.
In the present invention method compared with the existing technology, with advantages below：
1) raw material can be selected according to different prescriptions, prepares the conjugated linoleic acid product of higher amount, solve original
The limitation of material, enriches the sources of conjugated linoleic acid, it is not necessary to look for the vegetable oil that content is more than 80%, or
Go to lift the content of the Linoleic Acid in Safflower Oil less than 80%, change.
2) with linoleic acid Arrcostab as raw material, base catalyst consumption can be significantly reduced, and reduces initial reaction stage whereby
Saponification phenomenon, so as to reducing the resistance to mass tranfer of system and further avoiding using solvent, realize solvent-free reaction.Simultaneously
The glycerol and its derivant produced when avoiding with triglyceride as raw material causes to produce trimethoxypropane gave in isomerization operation
Or the probability of triethoxy propane.
3) under condition of no solvent, conjugated linoleic acid Arrcostab is isomerized to using strong base catalyst linoleic acid Arrcostab, then
Conjugated linoleic acid is obtained through saponification, reacts relatively mild, temperature is low, alkali number consumption is few, does not use poisonous and hazardous molten
Agent, greatly reduces the generation of all trans isomer, reduces the generation of alltranses body to greatest extent.
Therefore, it is raw material that the preparation method of conjugated linoleic acid of the invention selects linoleic acid Arrcostab, reduces base catalysis
The consumption of agent, using solvent-free direct reaction, it is to avoid using poisonous and hazardous organic solvent.By the control of reaction condition,
The content of trans acids in conjugated linoleic acid is reduced to a greater extent, improves the content of active ingredient in conjugated linoleic acid.Simultaneously
The present invention can just reach the content requirement of conjugated linoleic acid using lower reaction temperature, thus further save energy and
Raw material.Additionally, the present invention is using the vegetable oil rich in linoleic acid Arrcostab, raw material sources are enriched, reduce the dependence of safflower oil,
So as to effectively reduce production cost, with very strong practicality.
Specific embodiment
With reference to embodiment, the present invention is described in further detail, is easy to more clearly understand the present invention, but it
Not to the present invention constitute limit.
Embodiment 1
1) methyl linoleate (from the Oleum Helianthi) 200.0g of methyl linoleate content 84.0% is taken, in the guarantor of nitrogen
Under shield, 16.0g Feldalat NMs are added, stirring reaction 5h carries out solvent-free isomerization reaction at 130 DEG C, obtains CLA methyl esters
Crude product, the content of the unconverted methyl linoleate of sampling detection is 0.8%；
2) CLA methyl esters crude product is added in the sodium hydroxide aqueous alkali that mass concentration is 40% carries out soap
Change reaction, response time 1h, 90 DEG C of reaction temperature obtain conjugated linoleic acid soap；
3), after saponification terminates, 85% food grade phosphoric acid of Deca carries out acidification reaction, 90 DEG C of souring temperature, when system pH is to Jie
When between 1～2, stopping acidification, material stand a point liquid in proceeding to separatory funnel, discard lower aqueous layer, to upper strata oil reservoir successively
Using sour water, pure water to neutrality；
4) activated carbon of 20.0g, at 100 DEG C, decoloring reaction under vacuum condition after the oil reservoir dehydrate obtained by, are added
1h, material filtered while hot after decolouring, filtrate carry out molecular distillation and must be conjugated sub- oil in 160 DEG C～170 DEG C, under the conditions of 1Pa～5Pa
Acid product；
The conjugated linoleic acid total content 82.9% of gained, wherein all trans isomer content 0.8%, product acid number
The undesirable substances such as 197mgKOH/g, product clear ， bioxin, benzo ratio are not detected.
Embodiment 2
1) methyl linoleate (from the soybean oil) 1000.0g of methyl linoleate content 80.0% is taken, in the guarantor of nitrogen
Under shield, 20.0g Feldalat KMs are added, stirring reaction 6h carries out solvent-free isomerization reaction at 100 DEG C, obtains CLA methyl esters
Crude product, the content of the unconverted methyl linoleate of sampling detection is 0.3%；
2) CLA methyl esters crude product is added in the potassium hydroxide aqueous alkali that mass concentration is 10% carries out soap
Change reaction, response time 4h, 70 DEG C of reaction temperature obtain conjugated linoleic acid soap；
3), after saponification terminates, 85% food grade phosphoric acid of Deca carries out acidification reaction, 70 DEG C of souring temperature, when system pH is to Jie
When between 1～2, stopping acidification, material stand a point liquid in proceeding to separatory funnel, discard lower aqueous layer, to upper strata oil reservoir successively
Using sour water, pure water to neutrality；
4) activated carbon of 50.0g, at 90 DEG C, decoloring reaction under vacuum condition after the oil reservoir dehydrate obtained by, are added
45min, material filtered while hot after decolouring, filtrate carry out molecular distillation in 160 DEG C～170 DEG C, under the conditions of 3Pa～8Pa and must be conjugated
Linoleic acid product；
The conjugated linoleic acid total content 78.4% of gained, wherein all trans isomer content 0.8%, product acid number
The undesirable substances such as 197mgKOH/g, product clear ， bioxin, benzo ratio are not detected.
Embodiment 3
1) Ethyl linoleate (from the safflower oil) 1000.0g of Ethyl linoleate content 99.0% is taken, in the guarantor of nitrogen
Under shield, 40.0g potassium ethoxides are added, stirring reaction 2h carries out solvent-free isomerization reaction at 140 DEG C, obtains CLA methyl esters
Crude product, the content of the unconverted Ethyl linoleate of sampling detection is 0.1%；
2) conjugated linoleic acid ethyl ester crude product is added in the potassium hydroxide aqueous alkali that mass concentration is 20% carries out soap
Change reaction, response time 2h, 80 DEG C of reaction temperature obtain conjugated linoleic acid soap；
3), after saponification terminates, 85% food grade phosphoric acid of Deca carries out acidification reaction, 80 DEG C of souring temperature, when system pH is to Jie
When between 1～2, stopping acidification, material stand a point liquid in proceeding to separatory funnel, discard lower aqueous layer, to upper strata oil reservoir successively
Using sour water, pure water to neutrality；
4) activated carbon of 10.0g, at 110 DEG C, decoloring reaction under vacuum condition after the oil reservoir dehydrate obtained by, are added
0.5h, material filtered while hot after decolouring, filtrate carry out molecular distillation in 170 DEG C～180 DEG C, under the conditions of 5Pa～10Pa and must be conjugated
Linoleic acid product；
Products obtained therefrom conjugated linoleic acid total content 97.4%, wherein all trans isomer content 0.8%, product acid number
The undesirable substances such as 203mgKOH/g, product clear ， bioxin, benzo ratio are not detected.
From above-described embodiment as can be seen that the conjugated linoleic acid prepared with the method for the present invention, raw material is from being easy to get
Linoleic acid Arrcostab, through isomerization reaction and saponification, directly prepare, and the linoleic acid in vegetable oil contained
Amount does not have too high requirement.Meanwhile, in the conjugated linoleic acid for obtaining, main component is 9c, 11t- and 10t,12c-CLA
Two kinds of configurations, trans body content are less than 1%, and acid number meets the Chinese people altogether between 195mgKOH/g～205mgKOH/g
With the requirement in state Ministry of Public Health No. 12 bulletin in 2009 to conjugated linoleic acid.
On the premise of without departing from claims of the present invention protection domain, the numerical value in embodiment is adjusted and is also belonged to
In the scope of protection of the invention.
Claims (10)
1. a kind of preparation method of conjugated linoleic acid, it is characterised in that：The preparation method of the conjugated linoleic acid includes following step
Suddenly：
1) linoleic acid Arrcostab and base catalyst are carried out into solvent-free isomerization reaction, response time at 100 DEG C～140 DEG C
2h～6h；
2) by step 1) in reactant be added in aqueous alkali and carry out saponification and obtain conjugated linoleic acid soap；
3) by step 2) in conjugated linoleic acid soap be acidified to pH value to carry out the isolated oil reservoir of point liquid after 1～2, and wash oil
Layer；
4) by step 3) in oil reservoir carry out decolouring purification, and after removing solvent, obtain the conjugated linoleic acid.
2. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：The linoleic acid Arrcostab is by Portugal
The crude oil or refined oil of one or more in grape seed oil, safflower oil, Semen Maydis oil, soybean oil, Oleum Helianthi, Oleum Gossypii semen, and
What its derivant was obtained after purification.
3. the preparation method of conjugated linoleic acid according to claim 2, it is characterised in that：The derivant be Oleum Vitis viniferae,
One or more Fructus Gleditsia, acidification oil or deodorize in safflower oil, Semen Maydis oil, soybean oil, Oleum Helianthi, Oleum Gossypii semen is distillated
Thing.
4. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：The step (1) is protected in nitrogen
Under carry out.
5. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：Alkalescence in the step (1) is urged
Agent be Feldalat NM, Sodium ethylate, Feldalat KM or potassium ethoxide in one kind, its consumption for linoleic acid Arrcostab quality 2%～
8%.
6. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：Aqueous alkali in the step (2)
For NaOH aqueous solutions that mass concentration is 10%～40% or KOH aqueous solutions, saponification is at 60 DEG C～100 DEG C to react 1
～8h.
7. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：Acidifying in the step (3) is
Carry out at 70 DEG C～90 DEG C.
8. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：Washing in the step (3) is
Refer to, oil reservoir uses sour water, pure water to neutrality, branch vibration layer successively, and oil reservoir is dried.
9. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：Decolouring in the step (4) is pure
Change refers to, the activated carbon of linoleic acid Arrcostab quality 1%～10% is added after oil reservoir washing, at 90 DEG C～110 DEG C, vacuum condition
Lower decoloring reaction 0.5h～1h, then filtered while hot obtain the filtrate decolourized after purification.
10. the preparation method of conjugated linoleic acid according to claim 1, it is characterised in that：Removing in the step (4) is molten
Agent is referred to, by the filtrate decolourized after purification at 160 DEG C～180 DEG C, carries out molecular distillation and remove solvent under the conditions of 1Pa～10Pa.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108892609A (en) * | 2018-06-29 | 2018-11-27 | 菏泽中禾健元生物科技有限公司 | It is a kind of to prepare the linoleic method of high-purity using safflower seed oil |
| CN110845335A (en) * | 2019-11-05 | 2020-02-28 | 新疆庄子实业有限公司 | Method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as raw material |
| CN111955726A (en) * | 2020-09-15 | 2020-11-20 | 秦皇岛华道食品科技有限公司 | Production method of food composition for reducing fat, shaping body, relaxing bowels and moistening intestines and composition |
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| US20040225143A1 (en) * | 2003-05-08 | 2004-11-11 | Rongione Joseph C. | Manufacture of conjugated linoleic salts and acids |
| CN1580030A (en) * | 2003-08-04 | 2005-02-16 | 刘朝燊 | Method for synthesizing conjugated linoleic acid |
| CN104725217A (en) * | 2015-02-27 | 2015-06-24 | 蓬莱市海洋生物有限公司 | Production process of conjugated linoleic acids |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20040225143A1 (en) * | 2003-05-08 | 2004-11-11 | Rongione Joseph C. | Manufacture of conjugated linoleic salts and acids |
| CN1580030A (en) * | 2003-08-04 | 2005-02-16 | 刘朝燊 | Method for synthesizing conjugated linoleic acid |
| CN104725217A (en) * | 2015-02-27 | 2015-06-24 | 蓬莱市海洋生物有限公司 | Production process of conjugated linoleic acids |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108892609A (en) * | 2018-06-29 | 2018-11-27 | 菏泽中禾健元生物科技有限公司 | It is a kind of to prepare the linoleic method of high-purity using safflower seed oil |
| CN108892609B (en) * | 2018-06-29 | 2021-01-22 | 菏泽中禾健元生物科技有限公司 | Method for preparing high-purity linoleic acid by using safflower seed oil |
| CN110845335A (en) * | 2019-11-05 | 2020-02-28 | 新疆庄子实业有限公司 | Method for preparing conjugated linoleic acid ethyl ester by using safflower seed oil as raw material |
| CN111955726A (en) * | 2020-09-15 | 2020-11-20 | 秦皇岛华道食品科技有限公司 | Production method of food composition for reducing fat, shaping body, relaxing bowels and moistening intestines and composition |
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