CN101440030A - Supercritical preparation of conjugated linolic acid - Google Patents
Supercritical preparation of conjugated linolic acid Download PDFInfo
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- CN101440030A CN101440030A CNA2008100516414A CN200810051641A CN101440030A CN 101440030 A CN101440030 A CN 101440030A CN A2008100516414 A CNA2008100516414 A CN A2008100516414A CN 200810051641 A CN200810051641 A CN 200810051641A CN 101440030 A CN101440030 A CN 101440030A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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Abstract
The invention relates to a supercritical preparation method for conjugated linoleic acid and belongs to health-care food processing technology. A maize germ is subjected to impurity removal, drying and pulverization treatment; or maize germ oil is directly adopted to carry out supercritical reaction to prepare the conjugated linoleic acid. Supercritical CO2 is used as a fluid, is added with a proper entrainer and is subjected to extraction, reaction, selective separation and rectification under the conditions of certain pressure, temperature and time to prepare the conjugated linoleic acid. After the maize germ as a raw material reacts, residue is subjected to proper treatment to produce a high-protein or high-fibre food. The method can improve the preparation rate and the purity of the conjugated linoleic acid and has mild reaction condition; in the preparation process, the raw material has no denaturalization and no pollution and can be fully utilized so that no waste residue, no waste steam and no harmful substances produce and no residue organic solvent remains in product and byproduct in the production process; and the method belongs to an environment-friendly type production mode.
Description
Technical field
The invention belongs to health food processing technology.
Background technology
Conjugated linolic acid (Conjugated linoleic acids, CLA) be that a series of carbonatomss are 18, have a general name of the isomers lipid acid of conjugated dienes structure, can regard essential fatty acids linoleic (linoleic acid as, LA) derivative, 9c wherein, 11t-18: 2 and 10t, 12c-18: 2 have been had the important physical function by experiment confirm.Nineteen eighty-three, the MichaelPariza leader's of Wisconsin university research group finds a kind of cancer-resisting substance first in the beef of baking, 1987 is exactly CLA through this material of affirmations such as Ha, caused that subsequently people are to CLA extensive studies interest, show after further research, CLA has a series of surprising physiologically actives, 1996 national research council (NRC) CLA is classified as unique a kind of animal source lipid acid with antitumous effect.
CLA is less at occurring in nature content, mainly be present in the breast and meat product of ruminating animal ox, sheep etc., human body self can not synthesize CLA, must obtain from the external world, infer that from animal experimental data everyone recommended intake every day of CLA is for being no less than 3.5g, and there is not SC service ceiling, even based on the Hesperian reality of milk-product and animal food per capita intake also less than 1/3 of recommended amounts, therefore, CLA has become the research focus in the fields such as medicine and food, at present, the research for CLA mainly concentrates on physiological function and preparation method two aspects.Studies have shown that conjugated linolic acid has anticancer, antiobesity action.CLA is the growth and the growth of anticancer effectively, and CLA is inhibited to the growth of pernicious melanotic tumor, colorectal carcinoma and mastocarcinoma cell, and its intake that suppresses effect and CLA is proportionate.CLA can suppress synthesizing of animal body fat also can quicken the oxygenolysis of fat and body fat is descended, and CLA is to human body lowering blood-fat and reducing weight effect also highly significant.Discover, after human body is taken in and is rich in the cheese of CLA and cholesterol, CLA content significantly increases in the blood, cholesterol concentration does not then have considerable change, CLA can stop fat and thrombocyte to deposit on the arterial wall of congee shape pathology, therefore CLA can reduce cholesterol concentration in the blood, effectively suppresses arteriosclerotic generation.CLA also has enhance immunity power, improves metabolism of bone tissue in addition, promotes cell fission, stops muscle deterioration, delays the effects such as decline of body immunity.But the assisting therapy osteoporosis also has certain mitigation to rheumatic arthritis.
CLA is as extremely people's the favor of a kind of novel functional fatty acid, along with further research and discovery, the physiological mechanism that CLA helps HUMAN HEALTH will be revealed gradually, and CLA will become the wide function lipid of another market outlook after phosphatide and fish oil.At present, existing a large amount of functional food that contains CLA emerges in some developed countries such as Japan, the U.S., and China market CLA product is less, and all from import, exploitation CLA product and optimization CLA industrial process will become emphasis of future research.
The preparation method of CLA mainly adopts two big class methods both at home and abroad at present: the one, prepare CLA by chemical synthesis process, and the 2nd, utilize microorganism to carry out bio-transformation and prepare CLA.
The most frequently used chemical synthesis is a high temperature alkali isomerization method, is raw material with linolic acid or methyl linoleate, makes two key conjugations under the effect of alkali, obtains the CLA mixture of isomers.The catalyzer that high temperature alkali isomerization method adopts is a highly basic, and as KOH and NaOH etc., and temperature surpasses 150 ℃, and such high temperature highly basic reaction environment, easily causes the corrosion of equipment and instrument at operational hazards, and influence is produced and normally carried out.In addition in the isomerization reaction of high temperature highly basic, in order to make highly basic and grease uniform mixing, organic solvents such as ethylene glycol commonly used, dimethyl formamide, dimethyl sulfoxide (DMSO) and propylene glycol.This production method environmental pollution is bigger, and by product is many, more and more is restricted.Another method commonly used is the metal catalytic method, but utilizes catalysis linolic acid such as some transition element such as ruthenium, rhodium, platinum, palladium, chromium and iridium to produce isomerization reaction, and these metal ion organic coordination compounds commonly used or carbonyl compound react.This kind method is usually used in industrial production paint, replaces the double bond containing tung oil of expensive natural richness, and product is poisonous, non-food grade.The hydroxy fatty acid evaporation is that the unsaturated fatty acids with hydroxyl is a raw material, obtain CLA behind the catalytic dehydration, common raw material is ricinolic acid, ricinelaidic acid, oleic acid vinyl carbinol, methyl ricinoleate etc., industrial often is that raw material adopts evaporation to produce the pure product of CLA isomer with the methyl ricinoleate, make the higher c9 of purity, t11-CLA, but reaction yield is lower, and can generate the conjugated isomers of other position of double bond in the reaction, thereby influence its widespread use.Biotransformation method be meant the cell that utilizes linoleate isomerase or contain this enzyme with linolic acid (LA) and derivatives selectively thereof change into the isomer of CLA, i.e. 9c, 11t-18: 2 and 10t, 12c-18: 2.Found that at present some cud bacterium, bacterium acidi propionici and milk-acid bacteria can be converted into CLA with LA by biotransformation method.Compare with chemical synthesis, the specificity of biotransformation method is stronger, active CLA content of isomer height in the product, and the reaction conditions gentleness, but this method productive rate is low, and preparation CLA cost is higher, and is difficult to be applied to scale operation.
Summary of the invention
The invention provides a kind of overcritical method of producing with the separation and purification conjugated linolic acid, to solve the problem that the pollution that exists among the present preparation method is big, by product is many, reaction yield is lower, cost is higher and be difficult to be applied to scale operation, the present invention includes the following step:
One. the pre-treatment of maize or Fructus Maydis oil:
Earlier with maize impurity elimination, washing, dehydration then, dry, pulverize, make and contain the branch water yield less than 8%, granularity is less than the maize powder of 1mm; Fructus Maydis oil need take off organic solvent, comes unstuck, the purification process of deodorization, dehydration, and moisture content is not more than 0.5%;
Two. linoleic extraction of corn and enrichment:
Adopt supercritical CO
2The fluid reaction device extracts the corn linolic acid, extraction operating pressure 10MPa～50MPa, 35 ℃～55 ℃ of temperature, 60～180 minutes time, CO
2Flow 20L/h～30L/h.
Three. producing of conjugated linolic acid
Adopt supercritical CO
2Fluid reaction and extraction plant, with maize or corn linolic acid is raw material, the KOH add-on is KOH: raw material=1:(1～3), the poly(oxyethylene glycol) 400 add-on is poly(oxyethylene glycol) 400: raw material=4:(2～0.5), reaction pressure is 15Mpa～30Mpa, temperature of reaction is 50 ℃～135 ℃, time 1～4h;
Four. separation and purification
Get the reaction product that step 3 obtains, separator and rectifier by supercritical flow precursor reactant and extraction plant carry out separation and purification, obtain the conjugated linolic acid behind the purifying.Separation condition is operating pressure 2MPa～6MPa, 25 ℃～55 ℃ of temperature, and the rectifying condition is operating pressure 2MPa～6Mpa, 15 ℃～55 ℃ of temperature.
The present invention adopts supercritical reaction to produce conjugated linolic acid, avoid the High Temperature High Pressure vigorous reaction, reaction, separation and purifying are integrated to be finished, simultaneously, reactant and product all organic solvent-free are residual, remaining corn plumule powder continues on for the extraction of high stability corn edible oil behind the enrichment linolic acid, and residue can be used for the production of high-quality food fibre and high-protein food, has improved the quality and the nourishing function of utilization ratio of raw materials and product.Traditional method must be raw material with the linolic acid, adopts the high temperature alkaline process to produce conjugated linolic acid, and the inventive method is compared with it to be had efficiently, and low consumption is nontoxic, pollution-free, noresidue, easy to operate, and good selective, and can make production serialization, automatization.
The present invention adopts supercritical reaction to produce and the separation and purification conjugated linolic acid, have mild condition, efficiency of pcr product height, the purity advantages of higher, reaction, separation, purifying one are finished, and technology is easy, operational safety, saving equipment, reduce floor space, and by product is recycling, improves raw material availability.
The product that the present invention obtains, promptly can be used as foodstuff additive adds in the food that needs the reinforcement conjugated linolic acid, it is directly edible also to can be used as protective foods or medicine, for instant edible can be a base-material with conjugated linolic acid of the present invention, produces the conjugated linolic acid capsule.
Embodiment
Embodiment 1
One. the pre-treatment of maize
Maize is clean with 15 ℃～20 ℃ flowing water rinsing, remove not edible impurity, drain, under 1000～2000 rev/mins condition, carry out centrifuge dehydration, make its water content in the raw, hot-air seasoning under 60 ℃～80 ℃ conditions makes its water content less than 8% then, the maize of oven dry carries out pulverization process, makes the maize powder of granularity less than 1mm.
Two. the extraction and the enrichment of linolic acid or linolic acid fat
Utilize supercritical CO
2Fluid reaction and the extraction plant maize after with pre-treatment carries out supercritical CO
2Fluid extraction, extracting pressure 10MPa, 35 ℃ of temperature, 60 minutes time, CO
2Flow 20L/h.The Fructus Maydis oil color that obtains is yellowish, is as good as assorted flavor, and linoleic acid content is greater than 50%.Extract remainder does not have the production base-material that any organic solvent residual can be used for high-quality food fibre and high-protein food.
Three. producing of conjugated linolic acid
Utilize supercritical CO
2Fluid reaction and extraction plant are raw material with high linoleic acid Semen Maydis oil, the KOH add-on is KOH: raw material=1:1, the poly(oxyethylene glycol) 400 add-on is poly(oxyethylene glycol) 400: raw material=4:2, reaction pressure is 15Mpa, and temperature of reaction is 50 ℃, time 4h, produce conjugated linolic acid, the reaction conditions gentleness is not destroyed the physicochemical property of product, biological activity height.
Four. separation and purification
Reach to produce and get the reaction product that step 3 obtains after the requirement, pass through supercritical CO
2Fluid reaction carries out separating of conjugated linolic acid and purifying with the separator of extraction plant with rectifier.Mask work pressure 2MPa, 25 ℃ of temperature, rectifying operating pressure 2MPa, 15 ℃ of temperature.
Embodiment 2
One. the pre-treatment of maize
Maize is clean with 15 ℃～20 ℃ flowing water rinsing, remove not edible impurity, drain, under 1000～2000 rev/mins condition, carry out centrifuge dehydration, make its water content in the raw, hot-air seasoning under 60 ℃～80 ℃ conditions makes its water content less than 8% then, the maize of oven dry carries out pulverization process, makes the maize powder of granularity less than 1mm.
Two. the extraction and the enrichment of linolic acid or linolic acid fat
Utilize supercritical CO
2Fluid reaction and the extraction plant maize after with pre-treatment carries out supercritical CO
2Fluid extraction, 20MPa, 40 ℃ of temperature, 80 minutes time, CO
2Flow 25L/h.The Fructus Maydis oil color that obtains is yellowish, is as good as assorted flavor, and linoleic acid content is greater than 50%.Extract remainder does not have the production base-material that any organic solvent residual can be used for high-quality food fibre and high-protein food.
Three. producing of conjugated linolic acid
Utilize supercritical CO
2Fluid reaction and extraction plant are raw material with high linoleic acid Semen Maydis oil, the KOH add-on is KOH: raw material=1:2.5, the poly(oxyethylene glycol) 400 add-on is poly(oxyethylene glycol) 400: raw material=4:1, reaction pressure is 20Mpa, and temperature of reaction is 80 ℃, time 2h, produce conjugated linolic acid, the reaction conditions gentleness is not destroyed the physicochemical property of product, biological activity height.
Four. separation and purification
Reach to produce and get the reaction product that step 3 obtains after the requirement, carry out separating of conjugated linolic acid and purifying with rectifier by separator.Mask work pressure 4MPa, 35 ℃ of temperature, rectifying operating pressure 4MPa, 25 ℃ of temperature.
Embodiment 3
One. the pre-treatment of maize
With embodiment 1.
Two. the extraction and the enrichment of linolic acid or linolic acid fat
Utilize supercritical CO
2Fluid reaction and the extraction plant maize after with pre-treatment carries out supercritical CO
2Fluid extraction, extraction operating pressure 50MPa, 55 ℃ of temperature, 180 minutes time, CO
2Flow 30L/h.。The Fructus Maydis oil color that obtains is yellowish, is as good as assorted flavor, and linoleic acid content is greater than 50%.Extract remainder does not have the production base-material that any organic solvent residual can be used for high-quality food fibre and high-protein food.
Three. producing of conjugated linolic acid
Utilize supercritical CO
2Fluid reaction and extraction plant are raw material with high linoleic acid Semen Maydis oil, the KOH add-on is KOH: raw material=1:3, the poly(oxyethylene glycol) 400 add-on is poly(oxyethylene glycol) 400: raw material=4:0.5, reaction pressure is 30Mpa, and temperature of reaction is 135 ℃, time 1h, produce conjugated linolic acid, the reaction conditions gentleness is not destroyed the physicochemical property of product, biological activity height.
Four. separation and purification
Reach to produce and get the reaction product that step 3 obtains after the requirement, carry out separating of conjugated linolic acid and purifying with rectifier by separator.Mask work pressure 6MPa, 35 ℃ of temperature, rectifying operating pressure 6Mpa, 35 ℃ of temperature.
Embodiment 4
One. the pre-treatment of Fructus Maydis oil
The Fructus Maydis oil that solvent method extracts will carry out precipitation, comes unstuck, deodorization, dewaxing, processed, and the Fructus Maydis oil that milling process extracts need come unstuck, deodorization, dewaxing, processed, handles the back moisture content and is not more than 0.5%.Above-mentioned treatment process all is an ordinary method of the prior art.
Two. producing of conjugated linolic acid
With embodiment 1.
Three. separation and purification
Reach to produce and get the reaction product that step 3 obtains after the requirement, carry out separating of conjugated linolic acid and purifying with rectifier by separator.Mask work pressure 5MPa, 55 ℃ of temperature, rectifying operating pressure 5Mpa, 55 ℃ of temperature.
Embodiment 5
One. the pre-treatment of Fructus Maydis oil
With embodiment 4.
Two. producing of conjugated linolic acid
With embodiment 2.
Three. separation and purification
With embodiment 1.
Embodiment 6
One. the pre-treatment of Fructus Maydis oil
With embodiment 4.
Two. producing of conjugated linolic acid
With embodiment 3.
Three. separation and purification
With embodiment 1.
Claims (1)
1, a kind of overcritical method of producing conjugated linolic acid is characterized in that comprising the following steps:
One. the pre-treatment of maize or Fructus Maydis oil:
Earlier with maize impurity elimination, washing, dehydration then, dry, pulverize, make and contain the branch water yield less than 8%, granularity is less than the maize powder of 1mm; Fructus Maydis oil need take off organic solvent, comes unstuck, the purification process of deodorization, dehydration, and moisture content is not more than 0.5%;
Two. linoleic extraction of corn and enrichment:
Adopt supercritical CO
2Fluid reaction and extraction plant extract the corn linolic acid, extraction operating pressure 10MPa～50MPa, 35 ℃～55 ℃ of temperature, 60～180 minutes time, CO
2Flow 20L/h～30L/h.
Three. producing of conjugated linolic acid
Adopt supercritical CO
2Fluid reaction and extraction plant, with maize or corn linolic acid is raw material, the KOH add-on is KOH: raw material=1: (1～3), the poly(oxyethylene glycol) 400 add-on is a poly(oxyethylene glycol) 400: raw material=4: (2～0.5), reaction pressure is 15Mpa～30Mpa, temperature of reaction is 50 ℃～135 ℃, time 1～4h;
Four. separation and purification
Get the reaction product that step 3 obtains, separator and rectifier by the supercutical fluid reaction unit carry out separation and purification, obtain the conjugated linolic acid behind the purifying.Separation condition is operating pressure 2MPa～6MPa, 25 ℃～55 ℃ of temperature, and the rectifying condition is operating pressure 2MPa～6Mpa, 15 ℃～55 ℃ of temperature.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101870989A (en) * | 2010-05-28 | 2010-10-27 | 东北农业大学 | Method for preparing glyceride rich in conjugated linoleic acid in supercritical state by enzyme method |
| CN105193779A (en) * | 2015-09-11 | 2015-12-30 | 苏州大学 | New use of conjugated linoleic acid for promoting fracture healing |
| CN106753752A (en) * | 2016-12-13 | 2017-05-31 | 青岛嘉瑞生物技术有限公司 | A kind of health-care salicorne oil beneficial to hypotensive |
| CN106831472A (en) * | 2017-03-03 | 2017-06-13 | 北京宇极科技发展有限公司 | A kind of DMF salt bearing liquid wastes recovery process and system |
| CN107312805A (en) * | 2017-08-07 | 2017-11-03 | 中国农业大学 | A kind of preparation and its application of the polyunsaturated fatty acid rich in CLA |
| CN107586253A (en) * | 2016-07-06 | 2018-01-16 | 上海爱普植物科技有限公司 | One kind prepares linoleic method |
| CN112451512A (en) * | 2020-11-26 | 2021-03-09 | 青海省人民医院 | Pharmaceutical composition and application thereof in treating osteoporosis |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2393391C (en) * | 2000-01-12 | 2009-10-27 | Martin J. T. Reaney | Method for commercial preparation of preferred isomeric forms of ester free conjugated fatty acids with solvent systems containing polyether alcohol solvents |
| CN101063155B (en) * | 2007-05-25 | 2011-04-13 | 中国农业科学院农产品加工研究所 | Method for producing conjugated linolic acid by using linolic acid isomerase |
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2008
- 2008-12-22 CN CN2008100516414A patent/CN101440030B/en active Active
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101870989A (en) * | 2010-05-28 | 2010-10-27 | 东北农业大学 | Method for preparing glyceride rich in conjugated linoleic acid in supercritical state by enzyme method |
| CN101870989B (en) * | 2010-05-28 | 2012-11-14 | 东北农业大学 | Method for preparing glyceride rich in conjugated linoleic acid in supercritical state by enzyme method |
| CN105193779A (en) * | 2015-09-11 | 2015-12-30 | 苏州大学 | New use of conjugated linoleic acid for promoting fracture healing |
| CN107586253A (en) * | 2016-07-06 | 2018-01-16 | 上海爱普植物科技有限公司 | One kind prepares linoleic method |
| CN107586253B (en) * | 2016-07-06 | 2020-10-02 | 上海爱普植物科技有限公司 | Method for preparing linoleic acid |
| CN106753752A (en) * | 2016-12-13 | 2017-05-31 | 青岛嘉瑞生物技术有限公司 | A kind of health-care salicorne oil beneficial to hypotensive |
| CN106831472A (en) * | 2017-03-03 | 2017-06-13 | 北京宇极科技发展有限公司 | A kind of DMF salt bearing liquid wastes recovery process and system |
| CN106831472B (en) * | 2017-03-03 | 2019-03-22 | 北京宇极科技发展有限公司 | A kind of DMF salt bearing liquid wastes recovery process |
| CN107312805A (en) * | 2017-08-07 | 2017-11-03 | 中国农业大学 | A kind of preparation and its application of the polyunsaturated fatty acid rich in CLA |
| CN112451512A (en) * | 2020-11-26 | 2021-03-09 | 青海省人民医院 | Pharmaceutical composition and application thereof in treating osteoporosis |
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| CN101440030B (en) | 2011-12-07 |
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