CN101032278A - Combination including calcium conjugated linoleic acid and producing method thereof - Google Patents
Combination including calcium conjugated linoleic acid and producing method thereof Download PDFInfo
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- CN101032278A CN101032278A CNA2007100103629A CN200710010362A CN101032278A CN 101032278 A CN101032278 A CN 101032278A CN A2007100103629 A CNA2007100103629 A CN A2007100103629A CN 200710010362 A CN200710010362 A CN 200710010362A CN 101032278 A CN101032278 A CN 101032278A
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Abstract
The present invention discloses one kind of composition containing calcium conjugate linoleate for increasing the milk output of milk cow and its preparation process. The composition is prepared with vegetable oil as material, and through ester exchange reaction, molecular distillation, saponification, isomerization and metathetical reaction. It consists of alphatic calcium, water and impurity salt; and the alphatic calcium includes calcium conjugate linoleate accounting for 82-90 wt% of the composition, calcium palmitate, calcium stearate, calcium oleate and calcium linoleate accounting for 8-15 wt% of the composition. It has high calcium conjugate linoleate content, controllable content of other kinds of alphatic calcium and excellent physical character. It is used in raising milk cow to raise milk output obviously.
Description
Technical field
The present invention relates to a kind of composition and method of making the same that contains calcium conjugated linoleic acid, relate in particular to a kind of high-purity CLA calcium product of increasing milk production of cow and preparation method thereof that is used to.
Background technology
(Conjugated Linoleic Acid CLA) belongs to polyunsaturated fatty acid to CLA, is linoleic one group of isomer.In feed, add CLA, can significantly improve the CLA content in the milk, reduce the saturated fatty acid in the milk.Destroyed when the cow rumen for fear of CLA, usually with the calcium salt of CLA as feed addictive.Studies show that the interpolation of calcium conjugated linoleic acid (CLA-Ca) can improve the content of CLA in the milk, reduce the content of saturated aliphatic acid in the milk.Yet, but study less to the influence of milk production of cow about CLA-Ca.Liu Shijun etc. CLA function milk PP Pipe Compound high yield cow is searched for food and the research of the influence of the output of milk in find: the CLA material reduces milk production of cow or does not change substantially (HEILONGJIANG ANIMAL SCIENCE AND VETERINARY MEDICINE, 2006 the 9th phases: 26-27).
The patent No. is that 02110430.1 Chinese patent discloses a kind of composition of being made up of calcium palmitate, calcium stearate, calcium oleate, calcium linoleate and calcium conjugated linoleic acid.According to the content disclosed in this patent, said composition can reduce the fat content in the milk effectively and increase the content of CLA, but does not specifically report the influence of said composition to milk production of cow in the literary composition.This patent discloses the above-mentioned preparation of compositions method that contains calcium conjugated linoleic acid simultaneously, yet, adopt this method in same equipment, to produce, various compositions in the material plant oil all are brought into product, and the percentage composition of calcium conjugated linoleic acid is lower than 80% (the disclosed content of embodiment) in the product that makes; And saturated aliphatic acid in the product is higher as the content of palmitic acid and stearic acid etc., and the mass percent that calcium conjugated linoleic acid accounts for TFA calcium is lower than 85%; Secondly, products obtained therefrom is a blocks of solid, though can reach the requirement as feed addictive after crushed, its proterties, color etc. all can not make us very satisfied.
Summary of the invention
The object of the present invention is to provide a kind of highly purified CLA calcium product that improves milk production of cow and preparation method thereof.
Purpose of the present invention realizes by following technical proposals:
A kind of composition that contains calcium conjugated linoleic acid, said composition is composed of the following components by mass percentage:
Calcium conjugated linoleic acid 82～90%
All the other fatty acid calciums 8～15%
Water 0.8～2.0%
Impurity salt 0.8～1.6%
Wherein, the fatty acid calcium of all the other except that calcium conjugated linoleic acid comprises calcium palmitate, calcium stearate, calcium oleate and calcium linoleate.
Wherein said calcium conjugated linoleic acid preferred content is 85～88.5%, and all the other fatty acid calciums are 9～12%; Impurity salt mainly is NaCl and CaCl
2
The preparation method of said composition comprises the steps:
1. ester exchange reaction:
The vegetable oil, alcoholic solvent and the base catalyst that are rich in the linoleic acid triglyceride are dropped into reactor, under 30～70 ℃ of conditions, react 2～4h, get the linoleate crude product;
The alcoholic solvent of this step is C
1～C
3Short chain alcohol, the mol ratio of vegetable oil and alcoholic solvent are 1: 6～15, and the base catalyst inventory is 0.3～1.0% of a vegetable oil quality;
2. molecular clock:
Above-mentioned linoleate crude product is carried out molecular clock, 120～170 ℃ of vapo(u)rizing temperatures, operation residual voltage 3～10Pa, charging flow velocity 25～35L/h;
3. saponification isomerization:
Linoleate, solvent and base catalyst are dropped into autoclave, and preliminary filling pressure 0.5～2.0MP reacts 3～6h under 140～200 ℃ of conditions, gets the CLA alkali metal salt;
The solvent of this step is C
1～C
3Short chain alcohol and water are with arbitrary proportion mixing gained, and the volume ratio of linoleate and solvent is 1: 0.5～1, and the mol ratio of linoleate and alkali is 1: 1～2.5;
4. metathesis reaction:
Above-mentioned CLA alkali metal salt is dissolved in C
1～C
3Short chain alcohol and water are with the mixed solvent of volume ratio 1: 0.3～4, and adjust pH is 7～12; In solution, slowly drip the solubility calcium salting liquid of equivalent; Behind reaction 2～4h, filter drying.
Wherein, the described preferred sunflower oil of vegetable oil, safflower oil, common seepweed seeds oil and the soybean oil that is rich in the linoleic acid triglyceride; Described C
1～C
3Short chain alcohol particular methanol or ethanol, preferred NaOH of base catalyst or KOH; Described step 4. in, calcium ion concentration preferred 10～25% in the solubility calcium salting liquid.
The present invention adopts the substep method of operating to carry out the preparation of calcium conjugated linoleic acid, by rough linoleate is carried out molecular clock, improved the purity of subsequent step raw material, prevent that effectively the impurity in the material plant oil is introduced into product, therefore improve the content of the calcium conjugated linoleic acid in the product, reached 82%～90%; In addition, this method has also effectively been controlled the content of the fatty acid calcium of all the other except that calcium conjugated linoleic acid in the product, and comprised saturated fatty acid such as palmitic acid and the stearic acid etc. that are harmful to health in these fatty acid calciums, make that the content of calcium conjugated linoleic acid accounts for more than 85% of TFA calcium in the product; In addition, use the product of this method preparation, have good physical behavior, its natural form is even-grained white powder.
The composition that contains calcium conjugated linoleic acid of the present invention as the feed addictive feeding cow, can be increased the output of milk of milk cow effectively through 12 months the said compositions that experiment showed,, the amplification maximum can reach 35%.
The specific embodiment
Below by specific embodiment content of the present invention is further described.Relate among the present invention and all adopt following method to carry out the fatty acid compositional analysis in the composition:
1. sample is prepared
Get product of the present invention, add hcl acidifying, add n-hexane extraction three times after, reclaim n-hexane; After get a certain amount of oil and carry out derivatization, after extracting with n-hexane then, to be measured.
2. the testing conditions formed of gas chromatographic analysis aliphatic acid:
Capillary column: FFAP 30m * 0.25mm * 0.50um; Fid detector;
Column temperature: 180 ℃, vapourizing temperature: 220 ℃, detected temperatures: 220 ℃;
Flow rate of carrier gas: nitrogen 30ml/min.
Add 4.8 liters of methyl alcohol in 11 liters of sunflower oils, 81 gram potassium hydroxide, 35 ℃ were reacted 2 hours, told glycerine after the cooling, then at 6Pa, carried out the methyl linoleate that molecular clock obtains 90% content under 160 ℃ of conditions.Get 7.5 liters of methyl linoleates, add 4 liters of methyl alcohol, 1.7 kilograms of potassium hydroxide, 150 ℃ were reacted 5 hours down.
In 50 liters reactor, add 16 premium on currency and 14 liters of methyl alcohol in the CLA sylvite to 7.5 kilograms be rich in, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9～10, slowly the calcium chloride water of Dropwise 35 % is 3.9 kilograms, stirs while dripping, the still temperature control is about 30 ℃, reacted 3 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 88.1％ 9.4％ 1.2％ 0.5％ 0.8％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 0.4%
Calcium stearate 0.1%
Calcium oleate 7.1%
Calcium linoleate 1.8%
Add 250 ml methanol in 550 milliliters of safflower oils, 6 gram sheet alkali, 40 ℃ were reacted 2.5 hours, told glycerine after the cooling, then at 2Pa, carried out the methyl linoleate that molecular clock obtains 90% content under 140 ℃ of conditions.Get 150 milliliters of methyl esters, add 120 ml methanol, 25～30 gram sheet alkali, 155 ℃, normal pressure reacted 4.5 hours down.
In 2 liters glass reaction still, add 300 ml waters and 200 milliliters of ethanol in the CLA sodium salt to being rich in of 145.3 grams, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9～10, slowly drip 75 milliliters of 40% calcium chloride waters, stirring while dripping, the still temperature control is about 40 ℃, reacted 2 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 87.6％ 9.2％ 1.8％ 0.4％ 1.0％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 0.4%
Calcium stearate 0%
Calcium oleate 7.4%
Calcium linoleate 1.4%
Add 1.2 liters of methyl alcohol in the common seepweed seeds oil 2.5 rise, 20 gram KOH, 62 ℃ were reacted 2.5 hours, and told glycerine after the cooling; At 6Pa, carry out the methyl linoleate that molecular clock obtains 85% content under 150 ℃ of conditions; Get 150 milliliters of methyl esters, add 120 ml methanol, 30 gram sheet alkali, 155 ℃, normal pressure reacted 4.5 hours down.
In 2 liters glass reaction still, add 300 ml waters and 200 milliliters of ethanol in the CLA sodium salt to being rich in of 145.3 grams, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9～10, slowly drip 75 milliliters of 40% calcium chloride waters, stirring while dripping, the still temperature control is about 40 ℃, reacted 2 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 85.9％ 10.5％ 2.0％ 0.7％ 0.9％ |
Above-mentioned other calcium linoleates comprise:
Calcium palmitate 0.8%
Calcium stearate 0.2%
Calcium oleate 7.6%
Calcium linoleate 1.9%
Add 300 liters of methyl alcohol in 550 liters of soybean oils, 2.8 kilograms of NaOH, 380 ℃ were reacted 4 hours, told glycerine after the cooling, then at 8Pa, carried out the methyl linoleate that molecular clock obtains 85% content under 130 ℃ of conditions.Get 60 liters of methyl esters, add 45 liters of methyl alcohol, 9 kilograms of NaOH, 1.5MPa, 160 ℃ were reacted 4 hours down.
In reactor, add 100 premium on currency and 80 liters of methyl alcohol to being rich in the CLA sodium salt of obtaining of above-mentioned reaction, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 8, slowly drip 27 kilograms of 40% calcium chloride waters, stirring while dripping, the still temperature control is about 40 ℃, reacted 3 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 86.3％ 11.2％ 1.6％ 0.3％ 0.6％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 1.8%
Calcium stearate 0.7%
Calcium oleate 7.0%
Calcium linoleate 1.7%
Add 550 liters of ethanol in 1000 liters of sunflower oils, 6 kilograms of NaOH, 40 ℃ were reacted 3 hours, told glycerine after the cooling, then at 6～8Pa, carried out the methyl linoleate that molecular clock obtains 85% content under 155 ℃ of conditions.Get 580 liters of ethyl esters, add 380 liters of methyl alcohol, 95 kilograms of NaOH, 165 ℃ were reacted 6 hours down.
In reactor, 515 kilograms that obtain to above-mentioned reaction are rich in and add 1000 premium on currency and 800 liters of ethanol in the CLA sodium salt, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9, slowly drip 247 kilograms of 45% calcium chloride waters, stirring while dripping, the still temperature control is about 25 ℃, reacted 4 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 82.4％ 14.4％ 1.6％ 0.6％ 1.0％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 3.2%
Calcium stearate 1.2%
Calcium oleate 8.3%
Calcium linoleate 1.7%
Add 50 liters of methyl alcohol in 100 liters of soybean oils, 5 kilograms of NaOH, 40 ℃ were reacted 3 hours, told glycerine after the cooling, then at 6～8Pa, carried out the methyl linoleate that molecular clock obtains 85% content under 170 ℃ of conditions.Get 60 liters of methyl esters, add 45 liters of methyl alcohol, 9 kilograms of NaOH, 160 ℃ were reacted 5.5 hours down.
In reactor, add 100 premium on currency and 80 liters of methyl alcohol to being rich in the CLA sodium salt of obtaining of above-mentioned reaction, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9, slowly drip 27 kilograms of 40% calcium chloride waters, stirring while dripping, the still temperature control is about 25 ℃, reacted 4 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 82.8％ 13.8％ 1.9％ 0.5％ 1.0％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 3.3%
Calcium stearate 1.1%
Calcium oleate 7.7%
Calcium linoleate 1.7%
Add 1.1 liters of methyl alcohol in 2 liters of common seepweed seeds oils, 16 gram KOH, 50 ℃ were reacted 3 hours, and told glycerine after the cooling; At 6Pa, carry out the methyl linoleate that molecular clock obtains 85% content under 150 ℃ of conditions; Get 180 milliliters of methyl esters, add the mixed solvent (volume ratio of methyl alcohol and water is 1: 1) of 120 ml methanol and water, 30 gram sheet alkali, 165 ℃, normal pressure reacted 4.5 hours down.
In 2 liters glass reaction still, add 300 ml waters and 200 ml methanol in the CLA sodium salt to being rich in of 174 grams, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9～10, slowly drip 90 milliliters of 40% calcium chloride waters, stirring while dripping, the still temperature control is about 30 ℃, reacted 2 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 82.9％ 13.4％ 2.1％ 0.6％ 1.0％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 2.1%
Calcium stearate 1.6%
Calcium oleate 7.6%
Calcium linoleate 2.1%
Add 210 ml methanol in 450 milliliters of safflower oils, 5 gram sheet alkali, 40 ℃ were reacted 2.5 hours, told glycerine after the cooling, then at 2Pa, carried out the methyl linoleate that molecular clock obtains 90% content under 140 ℃ of conditions.Get 150 milliliters of methyl esters, add 120 ml waters, 30 gram sheet alkali, 170 ℃, normal pressure reacted 6 hours down.
In 2 liters glass reaction still, add 280 ml waters and 280 ml methanol in the CLA sodium salt to being rich in of 143 grams, fully after the stirring and dissolving, slowly drip concentrated hydrochloric acid and transfer pH to 9～10, slowly drip 72 milliliters of 40% calcium chloride waters, stirring while dripping, the still temperature control is about 40 ℃, reacted 2 hours, suction filtration gets product after the filter cake vacuum drying.
By analysis, this product is composed of the following components by mass percentage:
| Component | The quality percentage composition |
| Other fatty acid calcium moisture of CLA-Ca NaCl CaCl 2 | 86.9％ 9.6％ 2.1％ 0.6％ 0.8％ |
Above-mentioned other fatty acid calciums comprise:
Calcium palmitate 0.6%
Calcium stearate 0.3%
Calcium oleate 7.1%
Calcium linoleate 1.6%
Contain of the influence of the composition of calcium conjugated linoleic acid to milk production of cow
1 year this experimental period, the milk production of cow of raising with the feed that does not add the composition that contains CLA-Ca is contrast; The interpolation group mixes by composition and the milk cow forage that mass ratio 1: 1500～2000 will contain CLA-Ca, and carries out the raising of milk cow according to the feed every day standard of 30～40kg feed of every cow head; With the gross mass of giving milk (kg) of every month every group of milk cow divided by (milk ox head number * days of the month), as the per day output of milk of every ox in this month, unit: kilogram/(head day); Experimental result as shown in Figure 1.
From accompanying drawing 1 as can be seen, add the composition that contains CLA-Ca in the feed and can improve milk production of cow effectively, annual amplification reaches 28%, the highest amplification 35% (July).
Claims (8)
1. composition that contains calcium conjugated linoleic acid, said composition is composed of the following components by mass percentage:
Calcium conjugated linoleic acid 82～90%
All the other fatty acid calciums 8～15%
Water 0.8～2.0%
Impurity salt 0.8～1.6%
Wherein, the fatty acid calcium of all the other except that calcium conjugated linoleic acid comprises calcium palmitate, calcium stearate, calcium oleate and calcium linoleate.
2. the composition that contains calcium conjugated linoleic acid according to claim 1, the quality percentage composition that it is characterized in that calcium conjugated linoleic acid wherein is 85～88.5%, all the other fatty acid calcium content 9～12%.
3. the composition that contains calcium conjugated linoleic acid according to claim 1 is characterized in that described impurity salt mainly is NaCl and CaCl
2
4. the described preparation of compositions method that contains calcium conjugated linoleic acid of claim 1 comprises the steps:
1. ester exchange reaction:
The vegetable oil, alcoholic solvent and the base catalyst that are rich in the linoleic acid triglyceride are dropped into reactor, under 30～70 ℃ of conditions, react 2～4h, get the linoleate crude product;
The alcoholic solvent of this step is C
1～C
3Short chain alcohol, the mol ratio of vegetable oil and alcoholic solvent are 1: 6～15, and the base catalyst inventory is 0.3～1.0% of a vegetable oil quality;
2. molecular clock:
Above-mentioned linoleate crude product is carried out molecular clock, 120～170 ℃ of vapo(u)rizing temperatures, operation residual voltage 3～10Pa, charging flow velocity 25～35L/h;
3. saponification isomerization:
Linoleate, solvent and base catalyst are dropped into autoclave, and preliminary filling pressure 0.5～2.0MP reacts 3～6h under 140～200 ℃ of conditions, gets the CLA alkali metal salt;
The solvent of this step is C
1～C
3Short chain alcohol and water are with arbitrary proportion mixing gained, and the volume ratio of linoleate and solvent is 1: 0.5～1, and the mol ratio of linoleate and alkali is 1: 1～2.5;
4. metathesis reaction:
Above-mentioned CLA alkali metal salt is dissolved in C
1～C
3Short chain alcohol and water are with the mixed solvent of volume ratio 1: 0.3～4, and adjust pH is 7～12; In solution, slowly drip the solubility calcium salting liquid of equivalent; Behind reaction 2～4h, filter drying.
5. the preparation of compositions method that contains calcium conjugated linoleic acid according to claim 4 is characterized in that the described vegetable oil that is rich in the linoleic acid triglyceride is selected from sunflower oil, safflower oil, common seepweed seeds oil and soybean oil.
6. the preparation of compositions method that contains calcium conjugated linoleic acid according to claim 4 is characterized in that described C
1～C
3Short chain alcohol particular methanol or ethanol, preferred NaOH of base catalyst or KOH.
7. the preparation of compositions method that contains calcium conjugated linoleic acid according to claim 4 is characterized in that described step 4., and calcium ion concentration is 10～25% in the solubility calcium salting liquid.
8. the described composition of calcium conjugated linoleic acid that contains of claim 1 is in the application that improves in the milk cow milk crop.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107216249A (en) * | 2016-03-22 | 2017-09-29 | 浙江医药股份有限公司新昌制药厂 | A kind of preparation method of high-quality CLA |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1289758A (en) * | 1999-09-27 | 2001-04-04 | 济南建基生物基因有限公司 | Process for preparing conjugated linoleic acid |
| CN1159281C (en) * | 2002-05-31 | 2004-07-28 | 国家海洋局第一海洋研究所 | Composition containing conjugated calcium linoleate and making method thereof |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107216249A (en) * | 2016-03-22 | 2017-09-29 | 浙江医药股份有限公司新昌制药厂 | A kind of preparation method of high-quality CLA |
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Address after: 116600 Dalian medical science and Technology Development Zone, Liaoning 49, Dalian Patentee after: Dalian promise biological Limited by Share Ltd Address before: 116600 Dalian economic and Technological Development Zone, Liaoning Province, No. seven northeast street, No. 18 Patentee before: Dalian Innobioactives Co., Ltd. |