CN101177399B - Non-catalytic method for preparing conjugated linoleic acid glyceride - Google Patents
Non-catalytic method for preparing conjugated linoleic acid glyceride Download PDFInfo
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- CN101177399B CN101177399B CN2007101151333A CN200710115133A CN101177399B CN 101177399 B CN101177399 B CN 101177399B CN 2007101151333 A CN2007101151333 A CN 2007101151333A CN 200710115133 A CN200710115133 A CN 200710115133A CN 101177399 B CN101177399 B CN 101177399B
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- linoleic acid
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Abstract
The invention relates to the preparation method of a non-catalyzed conjugated linoleic acid glyceride. When the conjugated linoleic acid with the purity of 75% and the glycerol with the purity of 98% are put into the reaction kettle and evenly mixed according to the molar ratio of 1:1 to 1:3 for reaction under the vacuum condition. The temperature is controlled at 170 to 190 DEG C and the time for reaction is 1 to 5 hours. During the reaction, the vacuum pump is always used to let the reaction kettle be in the vacuum state. The vacuum pressure is kept below 50Pa under zero. The preparation method is characterized in that no strong alkali or other catalysts are used; the transformation rate of the conjugated linoleic acid is from 86% to 99.2% with high yield while no post-treatment working procedure. With the monoglyceride, the diglyceride and the triglyceride and small amount of conjugated linoleic acid that did not react, the conjugated linoleic acid glyceride has the advantages of preventing the cancer, reducing the cholesterol in the blood and the liver and preventing the atherogenic properties and the diabetes.
Description
One, technical field
The present invention relates to a kind of healthcare products and preparation field, specifically a kind of preparation method who does not have the catalysis conjugated linoleic acid glyceride.
Two, background technology
Lipase is hydrolysis grease class or the cruel enzyme of lipid acid.But, can cause ester interchange reaction under given conditions and from lipid acid and glycerine or lipid acid and ethanol synthetic glycerine or ester class (J.Gen.Appl.Microbiol., 10,13-22,1964; Proc.IVIFS:Ferment.Technol.Today, 315 ' 320,1972, Societyof Fermetation Technolgy Japan; Bichim.Biophys.Acta, 489,415-422,1977 etc.).In ester interchange reaction the synthetic glyceride type according to the displacement degree of the light base of glycerine divide into monoglyceride (MG), Diglyceride (1,2-DG, 1,3-DG, 2,3DG), triglyceride (TG).Diglyceride is the ester interchange reaction product of lipid acid and glycerine, and it is the grease constituent at the 1st, 2 or the 1st and 3 glycerine conjugated fatty acid, distinguishes with the general grease that is called " triglyceride " and treats.Recent findings, Diglyceride effect and general neutral grease relatively time the in vivo, the process of its digestion, absorption is identical, but can synthesize neutral fat again hardly, therefore also can not cause neutral fat content in the blood and have and do not increase the triumph of body fat effect even absorb, the people in the industry constantly studies this.The preparation method's of aforesaid Diglyceride research has to disclose in day disclosure special permission communique flat 6-34381 number and is raw material with the solid grease and is that the lipase reaction acquisition of origin has the preparation method of 85ry0 Diglyceride content with glycerine, Pseudomonas microorganism.But, be difficult to obtain have the problem points of the Diglyceride of 85q0 purity when aforesaid method has the shortcoming that forms the solid grease at normal temperatures and aqueous use.And, day disclosure special permission communique continue 64-71495 number and day disclosure special permission bulletin flat 11-123097 number in disclose grease be hydrolyzed to 1, behind the 3-positionally SpecifiClipase, 2 each stages acquisition of the lipid acid of decomposition and glycerine resynthesis have the preparation method of the grease constituent of 80% Diglyceride content.But aforesaid method has behind the hydrolysis reaction glycerine is carried out after the processed defective with lipid acid synthetic complex steps.The deficiency of above-mentioned for solving [Ib] topic, Korea S's special permission is applied for having opened altogether in 2001-0002974 number and make water and 1 in the grease of 100 weight unit, 3-positionally sPecific 1 ipase or non-SpeCific lipase obtain to have the preparation method of the grease constituent of the cruel content of two acid glycerols more than 60%.But two acid glycerols that aforesaid method has 60% above purity extremely when reaction finishes as there being water, can produce the side effect of the hydrolysis of lipid acid, and then the content of increase free fatty acids, exist to be difficult to remove the shortcoming of this free fatty acids, and exist free fatty acids will separate the shortcoming of the by product of processing about 40% again.Therefore, the research with highly purified two acid glycerol vinegar grease preparation methods easy to method for making, that productivity is high seems more urgent.On the one hand, conjugated linolic acid (conjugated linoleic acid, hereinafter to be referred as ' CLA ') be the conjugated isomers of linolic acid (linoleic acid is hereinafter to be referred as ' LA ') as indispensable fatty acid, the anti-natural acid composition that trace is found in the milk of animal or muscle.CLA is meant linoleic position and the geometrical isomer (p that has conjugated double bond (conjugated double bonds) in cis or the trans coordination (configuration).Sitional and geometric isomer), at this, show cis-9, trans-11 octadecadienoic acid (octadecadienoicacid) and the trans-10 of physiological function in the CLA isomer, the c15-12 octadecadienoic acid is called CLA.And, CLA reduces (Am.J.Physiol.1998.275:R667-R672) by body fat and suppresses fat reducing arteriosclerosis incidence (Artery.1997.22:266-277), improve immunizing power (J.Nut.1999.129:32-38), antitumous effect (Anticancer research.1997.17:969-973), promoting growth (J.Nut.2000.130:2981-2989) and have a good therapeutic action to diabetes etc. are ill.Because of having above-mentioned characteristic, CLA can be used for the effective ingredient of food and medicine.
Three, summary of the invention
The purpose of this invention is to provide a kind of preparation method who does not have the catalysis conjugated linoleic acid glyceride, overcome traditional many synthetic methods of making catalyzer of highly basic (KOH) etc., the temperature of reaction that exists is too high, product color is poor, need postprocessing working procedures such as washing, neutralization, drying, and equipment corrosion serious, three waste discharge is arranged, to shortcomings such as environment pollute.In recent years, people begin solid acid catalyst is researched and developed, but still do not change the color and luster problem of product.
The present invention is directed to the problem of above-mentioned existence, adopting is not having under the catalyzer chemosynthesis conjugated linoleic acid glyceride under the vacuum hydro-extraction condition.
Major technique of the present invention thes contents are as follows:
1, reaction environment: in reactor, carry out under the vacuum, vacuum pressure is-below the 50Pa.
2, reactant ratio: the mol ratio of conjugated linoleic acid glyceride and glycerine is 1: 1-1: between 3.
3, temperature of reaction: under 170-190 ℃ of temperature stirring reaction 3-5 hour, the transformation efficiency of CLA can reach 86%-99%.
The used conjugated linolic acid of the present invention is our company with the conjugated linolic acid patent of Suaeda salsa rapeseed oil production is 200410075727.2, and alcohol is glycerol for glycerine.
Temperature of reaction: 170-190 ℃, wherein 190 ℃ optimum.
The mol ratio of the glycerine of the conjugated linolic acid of purity 75% and purity 98% is 1: 1-1: 3, wherein 1: 1 best.
Reaction times: 1-5 hour, the reaction times be 5 hours this moment conversion rate of fatty acid the highest, can reach 99.2%.
The present invention compares with present ester class synthetic method and has the following advantages:
1, pollution-free: highly basic etc. are done the aftertreatment complexity that catalyzer makes product, and severe corrosion equipment, and three waste discharge is to shortcomings such as environment pollute, and catalyst-free of the present invention can be avoided these shortcomings.
2, transformation efficiency height: conjugated linolic acid transformation efficiency of the present invention can be up to more than 99%.
3, color and luster is good: the present invention adopts vacuum, at high temperature makes conjugated linolic acid not oxidized, and reaction product is a creamy white.
The resulting conjugated linoleic acid glyceride of the present invention is applied to grocery trade, fields such as chemical industry.
As mentioned above, preparation method according to aforesaid method, altogether preparation engineering easy, have very high productive rate, combine simultaneously have anticancer, reduce body fat, strengthening immunity or have prevention and the conjugated linolic acid of treatment diabetes effect and improved its effect.And, can provide according to method for preparing be healthcare products, pharmaceuticals or the high functionality foodstuff additive of effective constituent with the conjugated linoleic acid glyceride, perhaps the anti-additive of high functionality food (particularly fat-reducing foodstuff additive) have anticancer, reduce body fat, strengthening immunity or have prevention and treat the diabetes effect.
Four, no accompanying drawing.
Five, embodiment
Below be for preferred embodiment of the present invention is described.Conjugated linolic acid purity is 75%, and glycerine purity is 99%.
Embodiment 1
Add CLA15.45g in the interior there-necked flask that stirrer arranged, glycerine 5.29g is stirred in that reaction prepared conjugated linoleic acid glyceride in 5 hours under 190 ℃ of vacuum environments, and the CLA transformation efficiency is 99.2%.
Embodiment 2
Add CLA18.00g in the interior there-necked flask that stirrer arranged, glycerine 5.75g is stirred in that reaction prepared conjugated linoleic acid glyceride in 2 hours under 190 ℃ of vacuum environments, and the CLA transformation efficiency is 92.5%.
Embodiment 3
Add CLA12.64g in the interior there-necked flask that stirrer arranged, glycerine 4.19g is stirred in that reaction prepared conjugated linoleic acid glyceride in 3 hours under 190 ℃ of vacuum environments, and the CLA transformation efficiency is 96.48%.
Embodiment 4
Add CLA18.00g in the interior there-necked flask that stirrer arranged, glycerine 5.75g is stirred in that reaction prepared conjugated linoleic acid glyceride in 2 hours under 190 ℃ of vacuum environments, and the CLA transformation efficiency is 92.52%.
Embodiment 5
Add CLA14.08g in the interior there-necked flask that stirrer arranged, glycerine 4.84g is stirred in that reaction prepared conjugated linoleic acid glyceride in 4 hours under 180 ℃ of vacuum environments, and the CLA transformation efficiency is 86.37%.
Claims (1)
1. preparation method who does not have the catalysis conjugated linoleic acid glyceride, it is characterized in that with the conjugated linolic acid of purity 75% and the glycerine of purity 98% be 1 in molar ratio: 1-1: stir in 3 the proportioning adding reactor, under vacuum condition, react, vacuum tightness is-below the 50Pa, temperature is controlled at 170-190 ℃, reaction times is 1-5 hour, makes with the work of vacuum pump all the time to keep vacuum state in the reactor in reaction process.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2007101151333A CN101177399B (en) | 2007-11-23 | 2007-11-23 | Non-catalytic method for preparing conjugated linoleic acid glyceride |
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| CN2007101151333A CN101177399B (en) | 2007-11-23 | 2007-11-23 | Non-catalytic method for preparing conjugated linoleic acid glyceride |
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| CN101177399A CN101177399A (en) | 2008-05-14 |
| CN101177399B true CN101177399B (en) | 2011-04-27 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102584586B (en) * | 2012-02-07 | 2014-03-05 | 大连医诺生物有限公司 | Preparation method of conjugated linoleic acid glycerides |
| CN102827000A (en) * | 2012-09-11 | 2012-12-19 | 东北农业大学 | Method for preparing conjugated linoleic acid glyceride under subcritical water condition |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6177580B1 (en) * | 1998-04-21 | 2001-01-23 | Henkel Kommanditgesellschaft Auf Aktien | Conjugated linolenic acid-based synthetic triglycerides |
| JP2003049192A (en) * | 2001-08-08 | 2003-02-21 | Kao Corp | Method for producing monoglyceride |
| JP2003252829A (en) * | 2002-03-01 | 2003-09-10 | Kao Corp | Method for producing monoglyceride |
| WO2006088188A1 (en) * | 2005-02-21 | 2006-08-24 | Kao Corporation | Oil-and-fat composition |
-
2007
- 2007-11-23 CN CN2007101151333A patent/CN101177399B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6177580B1 (en) * | 1998-04-21 | 2001-01-23 | Henkel Kommanditgesellschaft Auf Aktien | Conjugated linolenic acid-based synthetic triglycerides |
| JP2003049192A (en) * | 2001-08-08 | 2003-02-21 | Kao Corp | Method for producing monoglyceride |
| JP2003252829A (en) * | 2002-03-01 | 2003-09-10 | Kao Corp | Method for producing monoglyceride |
| WO2006088188A1 (en) * | 2005-02-21 | 2006-08-24 | Kao Corporation | Oil-and-fat composition |
Non-Patent Citations (1)
| Title |
|---|
| 陈福明.双甘酯的生产及应用.《中国油脂》.1997,第22卷(第5期),49-51. * |
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