CN1438211A - Method for preparing conjugate linoleic acid - Google Patents
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- CN1438211A CN1438211A CN 02131721 CN02131721A CN1438211A CN 1438211 A CN1438211 A CN 1438211A CN 02131721 CN02131721 CN 02131721 CN 02131721 A CN02131721 A CN 02131721A CN 1438211 A CN1438211 A CN 1438211A
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Abstract
The invention discloses a method of making conjugated linoleic acid, using the oil or fat with linoleic acid and the alcohol solution of alkali to make isomerous reaction by the action of alkali catalyzer to get it. During the reaction, properly raise the temperature and improve the step of processing technique to increase conjugate rate and quality; change the condition of molecular distillation to achieve the refinement and simplify the refining technique.
Description
The present invention be " conjugated linoleic acid microcapsule " patent application (application number: 00111371.2, the applying date: dividing an application 2000.9.14) specifically is a kind of manufacture method of conjugated linolic acid, and it belongs to biological chemistry
Technical field.
(english abbreviation: CLA) technology of preparing is to utilize ethylene glycol to make solvent to traditional conjugated linolic acid, utilizes base-catalyzed method that linolic acid is changed into conjugated linolic acid.A nearest United States Patent (USP) (US pat.5,986,116) report is a raw material with safflower oil, sunflower seeds wet goods; With propylene glycol is solvent, and its solvent load is the heavy 1-10 of oil times; With potassium hydroxide and sodium methylate is catalyzer, and the 1-8 that its alkali consumption is the linolic acid molecule basically doubly; Under the condition of nitrogen gas stream, under 110-180 ℃, carried out isomerization reaction 1-5 hour, the linolic acid in the stock oil is converted into conjugated linolic acid.The transformation efficiency of the conjugated linolic acid that this United States Patent (USP) (US pat.5,986,116) discloses has only more than 80%, and the product of gained do not carry out further refiningly, and therefore the color of this product is quite dark.Have than higher dissolvent residual in this product, and the oxidation products in the product (Anisidine value) is than higher.
This conjugated linolic acid has only a kind of form of soft capsule at present as a kind of product, does not see other launch as yet.
The objective of the invention is the shortcoming at above-mentioned technology existence, suitably improve temperature of reaction by the present invention, material treatment process steps after the improvement isomerization reaction is to improve conjugation rate and product inner quality; By changing the condition of molecular distillation, product is made with extra care, simplify process for refining, prevent that anti--trans cla levels from increasing and preventing the oxidation of conjugated linolic acid, further improving the quality of products.Kind and broadened application scope in order to increase the conjugated linolic acid product change the single situation of its product form, develop a kind of conjugated linolic acid product of microencapsulation.
Task of the present invention is finished by following technical scheme, has developed a kind of conjugated linolic acid of microencapsulation, and it is made by conjugated linolic acid.Press following formulation conjugated linolic acid emulsion:
Components by weight (part)
Conjugated linolic acid 1
Modified food starch 1-3
Water 1.5-6.0
With above-mentioned material emulsification homogeneous at normal temperatures, spraying drying is made micro-capsule shape conjugated linolic acid particle again, and this particle diameter is in 10-300 μ and uniform particles, and is loose, adhesion, and its apparent peroxide value is: 1.19-3.95mmol/L; Surface oil is: 0.05-0.28%; Water content is: 0.68-2.80%.
The conjugated linolic acid of this microencapsulation, described material is the emulsification homogeneous at normal temperatures, be at first with modified food starch by the prescription weighing after, add in the water by the prescription weighing, fully dispersed with stirring it; Next heats this starch slurry to 82 ± 2 ℃, and adds the conjugated linolic acid by the prescription weighing in stirring, forms the emulsion in early stage; Adopt mixing speed to be once more: the emulsifying device general emulsion stirring and emulsifying in early stage of 5000-10000rpm 1-10 minute reaches emulsified particle till 10-300 μ.
The conjugated linolic acid of this microencapsulation, the spraying drying of described material, the inlet temperature of its equipment is: 120-200 ℃, temperature out is: 60-90 ℃, air output is: 24-400m
3/ hr, spray air pressure is: 1.0-1.5kg/cm
2, the scope of microcapsule diameter is made in spray: 10-300 μ; The recovery rate of whole microencapsulation process is: 95-97.1%.
The manufacture method of this conjugated linolic acid is, will contain the reaction raw materials and the alkali alcosol of linoleic oil or fat, under the effect of alkaline catalysts, carries out isomerization reaction and the conjugated linolic acid made.Described alkali alcosol is the glycerol solution of sodium hydroxide, after this solution and the reaction raw materials that contains linoleic oil or fat-rise join in the retort, seal this jar, carries out following steps again:
I, vacuum outgas: be in the apparent vacuum tightness of the table of this jar: under the 600-700mmHg, this jar time: 20-60 minute;
Ii, temperature reaction: when material temperature in the jar is risen to 130-190 ℃, pick up counting, the reaction times of this material isomerization reaction is: 2-6 hour;
Iii, change a jar cooling: after this material isomerization reaction in above-mentioned ii step finishes, reacted material is transferred in the transfer jar, the controlling tank temperature is at 70-90 ℃, soaking time: 5-7 hour;
Iv, change jar this material reaction in acidifying: iii step and finish after, this material is transferred in the pickling tank, adds an amount of hydrochloric acid or sulfuric acid, adjusting pH value stirred 30-60 minute to 1-3, left standstill and treated layering in 20-40 minute, it is pending to emit lower floor's solvent layer afterwards;
V, washing removal of impurities: will be deposited in the hot water that oil phase material in the pickling tank adds 50-70 ℃, and the volume of this hot water doubles the volume of this material at least, and insulation is being not less than under 50 ℃ agitator treating 20-40 minute, leave standstill again and treated layering in 20-40 minute, emit lower floor's water afterwards; So repetitive scrubbing is 4-5 time, and the pH value that is washed till washing water is till 6-7;
Vi, thermal dehydration: with the oil phase material in v step, heating thermal dehydration 0.5-1.0 hour, is made the crude product material of conjugated linolic acid under 70-80 ℃;
Vii, molecular distillation: the crude product material that will go on foot vi changes in the molecular distillation apparatus, and in the still-process, control distil process condition: 1. first step distillation temperature is below 150 ℃, and vacuum tightness is at 5-10Pa; 2. second stage distillation temperature is below 160 ℃, and vacuum tightness is made the finished product raw material of conjugated linolic acid at 0.5-2.0Pa.
The manufacture method of this conjugated linolic acid, described linoleic oil or the fat of containing, it is a safflower oil, sunflower seed oil, common seepweed seeds oil, raisin seed oil, water white gourd oil.
The manufacture method of this conjugated linolic acid, described iv an amount of hydrochloric acid or sulfuric acid of step, wherein the concentration of hydrochloric acid is: 10-30%, vitriolic concentration is: 5-36%; The scope of described adding appropriate amount of acid is more than a times of this volume of material after the iii step, reaction finished at least; The temperature that adds appropriate amount of acid is controlled at more than 50 ℃.
The manufacture method of this conjugated linolic acid, the described linoleic oil or the reaction raw materials of fat and the weight ratio of alcoholic solvent of containing is: 1: 2-4.
The manufacture method of this conjugated linolic acid, the described linoleic oil or the reaction raw materials of fat and the weight ratio of alkaline catalysts of containing is: 1: 0.2-0.25.
Advantage of the present invention is: the yield of reaction is than higher, and technical process is simple, the quality product height.Micro-capsule product of the present invention be with conjugated linolic acid with after suitable capsule material mixes, directly carry out emulsification homogeneous technology under the normal temperature, its processing step is concisely reasonable, homogenizing effect is good; And then carry out spraying drying, can get the microcapsule granule shape conjugated linolic acid finished product that yield reaches 95-97.1% through effective processing condition control.Present method need not heat in emulsion process, does not need to add in addition emulsifying agent yet, and technology is very simple.
The manufacture method of conjugated linolic acid of the present invention, be before reaction, to carry out vacuum outgas earlier, its purpose is except causing anoxic environment, also make temperature of reaction under negative pressure, in time reach isomerisation conditions, and the isomerization reaction temperature can be mentioned 130-190 ℃, the best is 180-190 ℃, and optimum reacting time is to be advisable in 4 hours, realizes that linolic acid reaches more than 98% as early as possible to the transformation efficiency of conjugated linolic acid.The used sodium hydroxide of the present invention is as catalyzer, and is more effective than potassium hydroxide, and price is more cheap than potassium hydroxide, more cheap than sodium methylate.The used glycerol of the present invention is made the conjugated linolic acid of solvent preparation, and is better than the conjugated linolic acid of doing the solvent preparation with propylene glycol and ethylene glycol as human food prods or foodstuff additive.The present invention is to the conjugated linolic acid product of gained, adopts single molecular distillation technique just to reach to remove the purpose of residual molten, dehydration, decolouring, deodorization and taste removal.Owing to adopt the two-step distillation device, below 150 ℃, vacuum tightness is more than the 5pa, to discard overhead product to the control of first step temperature, promptly removes residual solvent, moisture and other low-molecular-weight impurity in the product again; Through second stage molecular distillation, temperature is controlled at below 160 ℃ again, and vacuum degree control distills needed conjugated linolic acid about 1Pa.Remaining pigment, the polymkeric substance equimolecular quantity of lipid acid be high, and become to grade impurity will be as offal treatment.Because this purification techniques is only used a set of equipment, the operation of two steps, the product that can obtain to be of high quality, the product of gained almost are colourless, and the colourity that the Lovibond colorimeter records is red 0.2, Huang 1 is considerably beyond the standard (colourity that requires of international like product is red 1, yellow 10) of international like product; Anisidine value in the product significantly reduces, and can reach the exported product required standard.The residual rate of solvent can reach below the 1ppm in the product, does not have strange smell.
The present invention is that feedstock production has gone out conjugated linolic acid with common seepweed seeds oil, raisin seed oil and water white gourd oil also except being that feedstock production goes out the conjugated linolic acid with safflower oil and sunflower seed oil.With the conjugated linolic acid product of the microencapsulation of above-mentioned feedstock production, uniform particles, loose, adhesion.Still there is not this conjugated linolic acid product both at home and abroad.
Protection scope of the present invention not only is confined among the embodiment, and embodiment is embodied in protection scope of the present invention.
The capsule material of the microencapsulation raw material of selecting for use of the present invention be modified food starch promptly: HI-CAP100, it is that national of the United States food company makes.The concrete proportioning of CLA microencapsulation raw material of the present invention is as follows:
Composition components by weight percent (%)
HI-CAP100??????????????70
CLA oil 30
Water 130
Concrete processing step is:
(1) HI-CAP100 with weighing adds in the quantitative water, fully stirs to make it to disperse, and makes the modified food starch slurry.
(2) heat this starch slurry to 82 ± 2 ℃ and then, and in stirring, add conjugated linolic acid, form emulsifying materials liquid in early stage by the prescription weighing.
(3) adopt mixing speed to be once more: the refiner equipment of 5000-10000rpm, emulsifying materials liquid stirring and emulsifying is 1-10 minute in earlier stage, reaches emulsified particle till 10-300 μ.
(4) the last above-mentioned emulsion of spraying drying.This emulsion enters spray-drier.Spraying drying operational condition: 120 ℃ of inlet temperatures, 70 ℃ of temperature outs, air velocity 0.4m
3/ min, spray air pressure 1.4kg/cm
2.
Conjugated linoleic acid microcapsule of the present invention specifically prepares embodiment such as following table 1,2,3: table 1: microencapsulation conjugation industry oleic acid prepares embodiment:
| Reaction conditions | The conjugated linoleic acid microcapsule quality product | ||||||
| Experiment numbers | Stock oil/capsule material (w/w) | Inlet temperature (℃) | Temperature out (℃) | Yield (%) | Apparent peroxide value (mmol/L) | Surface oil (%) | Water content (%) |
| ????1 | ???1∶1.0 | ???160 | ???80 | ??95.6 | ????3.95 | ???0.18 | ??1.69 |
| ????2 | ???1∶1.5 | ???160 | ???80 | ??96.3 | ????3.27 | ???0.09 | ??1.65 |
| ????3 | ???1∶2.0 | ???160 | ???80 | ??95.8 | ????3.14 | ???0.09 | ??2.50 |
| ????4 | ???1∶2.5 | ???160 | ???80 | ??97.5 | ????2.46 | ???0.07 | ??2.80 |
| ????5 | ???1∶3.0 | ???160 | ???80 | ??96.9 | ????1.20 | ???0.05 | ??0.95 |
| ????6 | ???1∶1.5 | ???120 | ???80 | ??96.5 | ????3.10 | ???0.09 | ??1.65 |
| ????7 | ???1∶1.5 | ???140 | ???80 | ??95.8 | ????3.12 | ???0.08 | ??1.63 |
| ???8 | ???1∶1.5 | ???160 | ???80 | ??96.1 | ????3.11 | ??0.09 | ??1.63 |
| ???9 | ???1∶1.5 | ???180 | ???80 | ??96.4 | ????3.21 | ??0.09 | ??1.65 |
| ???10 | ???1∶1.5 | ???200 | ???80 | ??96.9 | ????3.01 | ??0.09 | ??1.64 |
| ???11 | ???1∶1.5 | ???170 | ???60 | ??96.5 | ????3.05 | ??0.09 | ??1.62 |
| ???12 | ???1∶1.5 | ???170 | ???80 | ??97.1 | ????3.02 | ??0.09 | ??1.62 |
| ???13 | ???1∶1.5 | ???170 | ???90 | ??97.0 | ????3.05 | ??0.09 | ??1.65 |
Table 2 microencapsulation CLA is strengthening peroxide value variation under the oxidation test condition
| Test fate (d) | 0 | 1 | 2 | 3 | 4 | 7 | 8 |
| CLA | 4.10 | 5.31 | 8.63 | 10.69 | 18.60 | 24.32 | 32.16 |
| Microencapsulation CLA | 2.50 | 2.72 | 2.91 | 3.10 | ?3.24 | ?3.45 | 4.11 |
The dissolution rate of CLA in table 3 micro-capsule (Chinese Pharmacopoeia method)
| Dissolution time (min) | 10 | 25 | 40 | 55 |
| Dissolution rate (%) | 35.35 | 56.32 | 75.96 | 79.17 |
The manufacture method of conjugated linolic acid of the present invention is with containing the reaction raw materials and the alkali alcosol of linoleic oil or fat, under the effect of alkaline catalysts, carry out isomerization reaction and the conjugation made linolic acid.Concrete processing condition such as following table 4,5:
Table 4, conjugated linolic acid prepares embodiment:
Table 5: molecular distillation processing condition embodiment:
| Reaction conditions | The conjugated linolic acid quality product | ||||||
| Experiment numbers | Stock oil (g) | Glycerol (g) | Sodium hydroxide (g) | Temperature of reaction (℃) | Reaction times (h) | Conjugation transformation efficiency (%) | Separate difficulty or ease |
| ???1 | ???100 | ???100 | ???20 | ???190 | ???3.0 | ????- | The difficult separation |
| ???2 | ???100 | ???200 | ???20 | ???190 | ???3.0 | ???99.5 | Difficult |
| ???3 | ???100 | ???300 | ???20 | ???190 | ???3.0 | ???99.5 | Easily |
| ???4 | ???100 | ???400 | ???20 | ???190 | ???3.0 | ???99.1 | Easily |
| ???5 | ???100 | ???200 | ???20 | ???190 | ???3.0 | ???95.0 | Easily |
| ???6 | ???100 | ???200 | ???10 | ???190 | ???3.0 | ???35.9 | Easily |
| ???7 | ???100 | ???200 | ???15 | ???190 | ???3.0 | ???76.9 | Easily |
| ???8 | ???100 | ???200 | ???20 | ???190 | ???3.0 | ???100 | Easily |
| ???9 | ???100 | ???200 | ???25 | ???190 | ???3.0 | ???100 | Easily |
| ???10 | ???100 | ???200 | ???20 | ???130 | ???3.0 | ???66.3 | Easily |
| ???11 | ???100 | ???200 | ???20 | ???150 | ???3.0 | ???89.2 | Easily |
| ???12 | ???100 | ???200 | ???20 | ???180 | ???3.0 | ???95.5 | Easily |
| ???13 | ???100 | ???200 | ???20 | ???190 | ???3.0 | ???99.5 | Easily |
| ???14 | ???100 | ???200 | ???20 | ???190 | ???1.0 | ???53.5 | Easily |
| ???15 | ???100 | ???200 | ???20 | ???190 | ???1.5 | ???89.7 | Easily |
| ???16 | ???100 | ???200 | ???20 | ???190 | ???2.0 | ???99.3 | Easily |
| ???17 | ???100 | ???200 | ???20 | ???190 | ???3.0 | ???99.5 | Easily |
| ???18 | ???100 | ???200 | ???20 | ???190 | ???4.0 | ???99.5 | Easily |
| Experiment numbers | Vacuum tightness (Pa) | Peroxide value (mmol/L) | The P-V.A value | Cla levels (%) |
| ??1 | ?????2.0 | ????3.03 | ????18.59 | ????72.32 |
| ??2 | ?????1.0. | ????2.03 | ????17.01 | ????72.15 |
| ??3 | ?????0.5 | ????1.32 | ????13.55 | ????72.72 |
The present invention is that feedstock production has gone out conjugated linolic acid with common seepweed seeds oil, raisin seed oil and water white gourd oil also except being that feedstock production goes out the conjugated linolic acid with safflower oil and sunflower seed oil.The present invention adopts the CLA content (%) of conjugated linolic acid of different types of stock oil preparation and transformation efficiency (%) as table 6: table 6, and the conjugation effect of different types of stock oil:
Claims (5)
1, a kind of manufacture method of conjugated linolic acid, be the reaction raw materials and the alkali alcosol that will contain linoleic oil or fat, under the effect of alkaline catalysts, the conjugated linolic acid that carries out isomerization reaction and make, it is characterized in that: described alkali alcosol is the glycerol solution of sodium hydroxide, this solution is with after containing linoleic oil or fatty reaction raw materials and joining in the retort, and at first tight-closed this jar carries out following steps again:
I, vacuum outgas: in the apparent vacuum tightness of the table of this jar be: under the 600-700mmHg, the degassing time of this material in this jar is: 20-60 minute;
Ii, temperature reaction: when material temperature in the jar is risen to 130-190 ℃, pick up counting, the reaction times of this material isomerization reaction is: 2-6 hour;
Iii, change a jar cooling: after this material isomerization reaction in above-mentioned ii step finishes, reacted material is transferred in the transfer jar, the controlling tank temperature is at 70-90 ℃, soaking time: 5-7 hour;
Iv, change a jar acidifying: this material of iii step cooling is transferred in the pickling tank, adds hydrochloric acid or sulfuric acid, regulate the pH value to 1-3, stirred 30-60 minute, leave standstill and treated layering in 20-40 minute, it is pending to emit lower floor's solvent layer afterwards;
V, washing removal of impurities: will be deposited in the hot water that oil phase material in the pickling tank adds 50-70 ℃, and the volume of this hot water doubles the volume of this material, and insulation is being not less than under 50 ℃ agitator treating 20-40 minute, leave standstill again and treated layering in 20-40 minute, emit lower floor's water afterwards; So repetitive scrubbing is 4-5 time, and the pH value that is washed till washing water is till 6-7;
Vi, thermal dehydration: with the oil phase material in v step, heating thermal dehydration 0.5-1.0 hour, is made the crude product material of conjugated linolic acid under 70-80 ℃;
Vii, molecular distillation: vi is gone on foot the crude product material change in the molecular distillation apparatus, in the still-process, control distil process condition: 1. first step distillation temperature is below 150 ℃, and vacuum tightness is at 5-10Pa; 2. second stage distillation temperature is below 160 ℃, and vacuum tightness is made the finished product raw material of conjugated linolic acid at 0.5-2.0Pa.
2, according to the manufacture method of the described conjugated linolic acid of claim 1, it is characterized in that: described linoleic oil or the fat of containing, it is a safflower oil, sunflower seed oil, common seepweed seeds oil, raisin seed oil, water white gourd oil.
3, according to the manufacture method of the described conjugated linolic acid of claim 1, it is characterized in that: the described iv step adds hydrochloric acid or sulfuric acid, and wherein the concentration of hydrochloric acid is: 10-30%, and vitriolic concentration is: 5-36%; Described adding hydrochloric acid or vitriolic scope are more than a times of this volume of material after the iii step, reaction finished at least; Described adding hydrochloric acid or vitriolic temperature are controlled at more than 50 ℃.
4, according to the manufacture method of the described conjugated linolic acid of claim 1, it is characterized in that: the described linoleic oil or the reaction raw materials of fat and the weight ratio of alcoholic solvent of containing is: 1: 2-4.
5, according to the manufacture method of the described conjugated linolic acid of claim 1, it is characterized in that: the described linoleic oil or the reaction raw materials of fat and the weight ratio of alkaline catalysts of containing is: 1: 0.2-0.25.
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|---|---|---|---|
| CN 02131721 CN1243707C (en) | 2000-09-14 | 2000-09-14 | Method for preparing conjugate linoleic acid |
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|---|---|---|---|
| CN 02131721 CN1243707C (en) | 2000-09-14 | 2000-09-14 | Method for preparing conjugate linoleic acid |
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|---|---|---|---|
| CN 00111371 Division CN1105097C (en) | 2000-09-14 | 2000-09-14 | Conjugated linoleic acid microcapsule |
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| CN1243707C CN1243707C (en) | 2006-03-01 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1332009C (en) * | 2004-09-07 | 2007-08-15 | 中国科学院武汉植物园 | Plant linolic acid purifying method |
| CN103702562A (en) * | 2011-06-29 | 2014-04-02 | 默沙东公司 | Process for preparing chiral dipeptidyl peptidase-iv inhibitors |
| CN105087690A (en) * | 2014-05-22 | 2015-11-25 | 中国科学院兰州化学物理研究所 | Method for preparing conjugated linoleic acid by utilizing jasmine |
| US9862725B2 (en) | 2014-07-21 | 2018-01-09 | Merck Sharp & Dohme Corp. | Process for preparing chiral dipeptidyl peptidase-IV inhibitors |
| CN108689831A (en) * | 2018-06-29 | 2018-10-23 | 中粮塔原红花（新疆）有限公司 | A kind of conjugated linoleic acid preparation method |
| CN110818554A (en) * | 2019-11-29 | 2020-02-21 | 宁夏农林科学院动物科学研究所 | Method for extracting conjugated linoleic acid from Tibet sheep tail fat by two-stage short-path molecular distillation |
-
2000
- 2000-09-14 CN CN 02131721 patent/CN1243707C/en not_active Expired - Fee Related
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1332009C (en) * | 2004-09-07 | 2007-08-15 | 中国科学院武汉植物园 | Plant linolic acid purifying method |
| CN103702562A (en) * | 2011-06-29 | 2014-04-02 | 默沙东公司 | Process for preparing chiral dipeptidyl peptidase-iv inhibitors |
| US9187488B2 (en) | 2011-06-29 | 2015-11-17 | Merck Sharp & Dohme Corp | Process for preparing chiral dipeptidyl peptidase-IV inhibitors |
| US9527855B2 (en) | 2011-06-29 | 2016-12-27 | Merck Sharp & Dohme Corp. | Process for preparing chiral dipeptidyl peptidase-IV inhibitors |
| CN105087690A (en) * | 2014-05-22 | 2015-11-25 | 中国科学院兰州化学物理研究所 | Method for preparing conjugated linoleic acid by utilizing jasmine |
| US9862725B2 (en) | 2014-07-21 | 2018-01-09 | Merck Sharp & Dohme Corp. | Process for preparing chiral dipeptidyl peptidase-IV inhibitors |
| US10053466B2 (en) | 2014-07-21 | 2018-08-21 | Merck Sharp & Dohme Corp. | Process for preparing chiral dipeptidyl peptidase-IV inhibitors |
| CN108689831A (en) * | 2018-06-29 | 2018-10-23 | 中粮塔原红花（新疆）有限公司 | A kind of conjugated linoleic acid preparation method |
| CN110818554A (en) * | 2019-11-29 | 2020-02-21 | 宁夏农林科学院动物科学研究所 | Method for extracting conjugated linoleic acid from Tibet sheep tail fat by two-stage short-path molecular distillation |
| CN110818554B (en) * | 2019-11-29 | 2022-04-08 | 宁夏农林科学院动物科学研究所 | Method for extracting conjugated linoleic acid from Tibet sheep tail fat by two-stage short-path molecular distillation |
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| Publication number | Publication date |
|---|---|
| CN1243707C (en) | 2006-03-01 |
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