CN101851155B - Method for separating octadecadienoic acid from mixed long-chain fatty acid - Google Patents
Method for separating octadecadienoic acid from mixed long-chain fatty acid Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 34
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 title claims abstract description 26
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Abstract
The invention relates to a method for separating octadecadienoic acid from mixed long-chain fatty acid, which adopts a fractional extraction method to separate the octadecadienoic acid from the mixed long-chain fatty acid by taking one of acetonitrile, furfural, dimethyl sulfoxide, dimethylformamide, N-methyl-2-pyrrolidone and sulfolane or a mixture thereof as an extracting agent and one of petroleum ether the boiling range of which is 60-90 DEG C or 90-120 DEG C, hexane, heptane and octane or a mixture thereof as a detergent. The process adopts organic solvents commonly used in industry, and the method has the advantages of simple process, high product quality, high yield, low production cost, high safety, environmental production, easy industrial production and the like.
Description
Technical field
The present invention relates to a kind of method of separating octadecadienoic acid from hybrid long chain lipid acid, particularly a kind of method that adopts fractional-distillation extraction to separate octadecadienoic acid belongs to technical field of chemical engineering.
Background technology
Octadecadienoic acid is a kind of unsaturated fatty acids that contains two two keys, and it comprises linolic acid (Linoleic Acid) and conjugated linolic acid (Conjugated Linoleic Acid).Linolic acid is suitable, suitable-9,12 octadecadienoic acid, is present in the natural animal-plant grease, is essential fatty acid.Studies show that physiologically actives such as linolic acid has that the cells in vivo of keeping film is complete, control cell metabolism, reducing cholesterol level, prevention and treatment cardiovascular and cerebrovascular diseases.Conjugated linolic acid is the octadecadienoic acid that contains conjugated double bond, is linoleic isomers.Studies show that that conjugated linolic acid has is anticancer, fat-reducing, atherosclerosis, improve immunity of organisms, promote physiologically active such as growth, be widely used in fields such as medicine, food, makeup.
In order to satisfy the demand of high purity linolic acid on the market or conjugated linolic acid better, purifying linolic acid or conjugated linolic acid become the focus of people's research day by day.At present octadecadienoic acid mainly is to obtain from the hybrid long chain lipid acid that crude vegetal obtains through saponification and isomerization reaction, hybrid long chain lipid acid is the complicated fatty acid mixt of carbochain more than 10, generally contains longer chain fatty acids such as 20 carbon monoenoic acids, octadecadienoic acid, oleic acid, Lignoceric acid, mountain Yu acid, eicosanoic acid, stearic acid, palmitinic acid, tetradecanoic acid.And these lipid acid are intermediate molecular weight, high boiling point, thermographic compound, boiling point, molecular free path, solubleness and molecular dimension are very approaching between the compound, method selectivity such as rectifying, molecular distillation, crystallization and membrane sepn are not high, are not enough to octadecadienoic acid is separated.
The common method of present industrial separation and purifying octadecadienoic acid mainly contains urea adduct method, adsorption chromatography and lipase hydrolysis method etc.
Patent documentation US 5243046 is to utilize the difference of index of unsaturated fatty acid to separate with the urea adduct method that US 5106542 mentions; having urea packetize compound easy and simple to handle, cheap, formed can effectively protect two keys not oxidated; but its Tc is low; need repeatedly crystallization just can obtain the purity high product; the process yield is low; need to consume a large amount of urea and organic solvent, and for separating two close lipid acid weak effects of key number.Wu (Wu MY, Ding H, WangS, et al.Optimizing Conditions for the Purification of Linoleic Acid fromSunflower Oil by Urea Complex Fractionation.JOURNAL OF THEAMERICAN OIL CHEMISTS SOCIETY, 2008,85:677-684) etc. utilization response curve design method is optimized for urea crystals technology, when urea/fatty acid ratio is 0.94 (m/m), 95% ethanol/urea ratio is 5 (v/m), Tc is 18 ℃, crystallization time is 5h, and linoleic purity and yield reach 87.8% and 83.4% respectively.Kim (Kim Y J, Lee K W, Lee S, et al.The production of high-purity conjugated linoleic acid (CLA) using two-step urea-inclusion crystallization and hydrophilic arginine-CLAcomplex.JOURNAL OF FOOD SCIENCE, 2003,68:1948-1951) etc. to obtain purity be 95% conjugated linolic acid to two step of employing urea adduct method, only has 35% but yield is low.
The adsorption chromatography that patent documentation US 5175324 and CN 101486951A mention is to utilize load to have silica gel, gac or the aluminum oxide of urea to be sorbent material, is eluent with sherwood oil, normal hexane equal solvent, can realize that oleic acid separates with linoleic.It utilizes the fine difference of lipid acid and adsorbant function group molecular interaction (hydrogen bond, dipole/polarity, πDian Zi and hydrophobic interaction), realizes through theoretical stage balance repeatedly separating, and selectivity height, universality are good.But this method has the following disadvantages: the functional group density of (1) sorbent material is little, loading capacity is little, causes treatment capacity little, and solvent consumption is big; (2) based on molecular diffusion, rate of mass transfer is slow in the duct of sorbent material for longer chain fatty acid.Use supercritical fluid chromatography and simulated moving bed chromatography technology and can reduce the utilization ratio that solvent consumption improves sorbent material, but these technology are higher to equipment requirements.
In addition, patent documentation US 6537787 and US 5470741 adopt lipase hydrolysis method purifying unsaturated fatty acids, though can obtain the unsaturated fatty acids of higher degree, the production cost height, step is many, is unsuitable for large-scale industrial production.
Summary of the invention
The invention provides a kind of novel method of separating octadecadienoic acid from hybrid long chain lipid acid, this method is simple to operate, quality product is high, yield is high, cost is low, be easy to industrialization.
A kind of method of from hybrid long chain lipid acid, separating octadecadienoic acid, hybrid long chain lipid acid is dissolved in the washing composition, be made into stock liquid, cat head at the fractionation extraction tower feeds extraction agent, feed washing composition at the bottom of the tower, feed stock liquid in the tower, carry out fractionation extraction, collect extraction liquid, vacuum obtains octadecadienoic acid after steaming and desolventizing.
Described hybrid long chain lipid acid is the product that crude vegetal process saponification and isomerization reaction obtain.
The preferred sunflower seed oil of described crude vegetal, safflower oil, Oleum Gossypii semen, soya-bean oil, sesame oil, Rice pollard oil, Semen Maydis oil or peanut oil.
Described hybrid long chain lipid acid main component is longer chain fatty acids such as 20 carbon monoenoic acids, octadecadienoic acid, oleic acid, Lignoceric acid, mountain Yu acid, eicosanoic acid, stearic acid, palmitinic acid, tetradecanoic acid.
The fractionation extraction tower is divided into extraction section and washing section two portions, and tower body top is extraction section, and the bottom is washing section.Extraction agent feeds extraction tower from the extraction section top, stock liquid feeds extraction tower between extraction section and washing section, and washing composition feeds extraction tower from the bottom of washing section, merges stock liquid in the extraction section bottom and enters extraction section together.Extraction section and washing section all load efficient extraction stuffing, can be the fillers of unlike material and structure, preferred stainless steel θ ring filler.Extraction phase carries out multi-stage countercurrent with washing and contacts in extraction tower, flow out the extraction liquid (heavy phase) of enrichment octadecadienoic acid from the bottom of washing section, collect extraction liquid, vacuum obtains the octadecadienoic acid product after steaming and desolventizing, and flows out the raffinate (light phase) that is rich in all the other lipid acid except octadecadienoic acid from the top of extraction section.Whole process is the operate continuously process.
Described octadecadienoic acid is a kind of in linolic acid or the conjugated linolic acid.Two kinds of lipid acid generally do not exist simultaneously.
The extraction agent of described fractionation extraction is a kind of or its mixture in acetonitrile, furfural, dimethyl sulfoxide (DMSO), dimethyl formamide, N-N-methyl-2-2-pyrrolidone N-, the tetramethylene sulfone.
The extraction agent of described fractionation extraction is preferably a kind of or its mixture of furfural, dimethyl sulfoxide (DMSO) and N-N-methyl-2-2-pyrrolidone N-.
The washing composition of described fractionation extraction is that boiling range is a kind of or its mixture in sherwood oil, hexane, heptane and the octane of 60-90 ℃ or 90-120 ℃.When carrying out fractionation extraction, take all factors into consideration factors such as quality product, production cost, the volume flow ratio of the stock liquid of fractionation extraction of the present invention, extraction agent, washing composition is 1-2: 4-20: 2-15.
If the concentration of hybrid long chain lipid acid is lower in the stock liquid, then the utilization ratio of solvent is low, consumes big.Can reduce selectivity coefficient and partition ratio when concentration is excessive, can cause the consumption of extraction agent big, actual needed theoretical plate number increases.
The concentration of hybrid long chain lipid acid is 0.5-120g/L in the described stock liquid.The preferred 20-80g/L of the concentration of hybrid long chain lipid acid in the stock liquid.
Temperature can influence the phase equilibrium relationships of composition in two-phase such as 20 carbon monoenoic acids in the hybrid long chain lipid acid, oleic acid, Lignoceric acid, mountain Yu acid, eicosanoic acid, stearic acid, palmitinic acid, tetradecanoic acid.Temperature is too high then can to reduce partition ratio and selectivity, and it is rotten to cause heat-sensitive substance to take place; Temperature is low excessively, and the viscosity of stock liquid, extraction agent, washing composition all can become greatly, and rate of mass transfer is slack-off, is unfavorable for production operation.And cross low or too high temperature and all need be realized by bigger energy expenditure, cause the increase of production cost.Therefore, fractionation extraction of the present invention is chosen under the 20-60 ℃ of temperature and operates.
Beneficial effect of the present invention is:
1. the present invention adopts the fractionation extraction technology, and loading capacity is big, production capacity is high, cost reduces greatly.
2. the present invention selects industrial common solvent for use, is easy to recycling.
Simple, the stable operation of flow process of the present invention, energy consumption is low, yield is high, good product quality.Obtain the purity of octadecadienoic acid product greater than 95%, under preferred condition, yield is greater than 95%.
Description of drawings
Fig. 1 is fractionation extraction process schematic flow sheet of the present invention.
Embodiment
As shown in Figure 1, fractionation extraction tower of the present invention is divided into extraction section and washing section two portions, and tower body top is extraction section, and the bottom is washing section.Extraction agent feeds extraction tower from the extraction section top, stock liquid feeds extraction tower between extraction section and washing section, and washing composition feeds extraction tower from the bottom of washing section, merges stock liquid in the extraction section bottom and enters extraction section together.Extraction section and washing section all load efficient extraction stuffing, can be the fillers of unlike material and structure, preferred stainless steel θ ring filler.Extraction phase carries out multi-stage countercurrent with washing and contacts in extraction tower, flow out the extraction liquid (heavy phase) of enrichment octadecadienoic acid from the bottom of washing section, collect extraction liquid, vacuum obtains the octadecadienoic acid product after steaming and desolventizing, and flows out the raffinate (light phase) that is rich in all the other lipid acid except octadecadienoic acid from the top of extraction section.Whole process is the operate continuously process.
Embodiment 1
Sunflower seed oil is mainly contained the hybrid long chain lipid acid (total fatty acid content is 99%, and wherein cla levels is 70%) of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid through saponification and isomerization reaction.Make hybrid long chain lipid acid and be dissolved in the hexane, be mixed with the stock liquid that total concn is 40g/L.Being extraction agent with the furfural, is washing composition with the hexane, and stock liquid, extraction agent, washing composition three's volume flow ratio is 1: 4: 5, and extraction stuffing is 2mm stainless steel θ ring filler, carries out fractionation extraction under 40 ℃.Extraction liquid obtains the conjugated linolic acid product after steaming desolventizes through vacuum, and product purity is 99%, and product yield is 96.5%.
Embodiment 2
Safflower oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of linolic acid, oleic acid, stearic acid, palmitinic acid, wherein linoleic acid content is 76%), make hybrid long chain lipid acid and be dissolved in the heptane, be mixed with the stock liquid that total concn is 60g/L.Being extraction agent with the dimethyl sulfoxide (DMSO), is washing composition with the heptane, and stock liquid, extraction agent, washing composition three's volume flow ratio is 1: 8: 4, and extraction stuffing is 4mm stainless steel θ ring filler, carries out fractionation extraction under 40 ℃.Collect extraction liquid, vacuum obtains the linolic acid product after steaming and desolventizing, and product purity is 97%, and product yield is 95.3%.
Embodiment 3
Oleum Gossypii semen is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, tetradecanoic acid, wherein cla levels is 56%), make hybrid long chain lipid acid and be dissolved in the hexane, be mixed with the stock liquid that total concn is 80g/L.Being extraction agent with the dimethyl formamide, is washing composition with the hexane, and stock liquid, extraction agent, washing composition three's volume flow ratio is 2: 20: 6, and extraction stuffing is 2mm stainless steel θ ring filler, carries out fractionation extraction under 30 ℃.Collect extraction liquid, obtain the conjugated linolic acid product after steaming desolventizes through vacuum, product purity is 95%, and product yield is 90.1%.
Embodiment 4
Soya-bean oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, wherein cla levels is 60%), make hybrid long chain lipid acid and be dissolved in the 60-90 ℃ of sherwood oil, be mixed with the stock liquid that total concn is 20g/L.Be extraction agent with the acetonitrile, be washing composition with 60-90 ℃ of sherwood oil, stock liquid, extraction agent, washing composition three's volume flow ratio is 1: 5: 10, extraction stuffing is the Raschig ring ceramic packing, under 20 ℃, carry out fractionation extraction, collect extraction liquid, obtain the conjugated linolic acid product after steaming desolventizes through vacuum, product purity is 96%, and product yield is 94.3%.
Embodiment 5
Sesame oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, wherein cla levels is 50%), make hybrid long chain lipid acid and be dissolved in the octane, be mixed with the stock liquid that total concn is 100g/L.Be extraction agent with the tetramethylene sulfone, be washing composition with the octane, stock liquid, extraction agent, washing composition three's volume flow ratio is 1: 4: 15, extraction stuffing is 4mm stainless steel θ ring filler, under 60 ℃, carry out fractionation extraction, collect extraction liquid, obtain the conjugated linolic acid product through behind the vacuum concentration, product purity is 97%, and product yield is 84.3%.
Embodiment 6
Rice pollard oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, tetradecanoic acid, wherein cla levels is 40%), make hybrid long chain lipid acid and be dissolved in the 90-120 ℃ of sherwood oil, be mixed with the stock liquid that total concn is 120g/L.Be extraction agent with the N-N-methyl-2-2-pyrrolidone N-, be washing composition with 90-120 ℃ of sherwood oil, stock liquid, extraction agent, washing composition three's volume flow ratio is 2: 7: 3, extraction stuffing is 2mm stainless steel θ ring filler, under 40 ℃, carry out fractionation extraction, collect extraction liquid, obtain the conjugated linolic acid product through behind the vacuum concentration, product purity is 96%, and product yield is 94.5%.
Embodiment 7
Safflower oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, wherein cla levels is 80%), make hybrid long chain lipid acid and be dissolved in the hexane, be mixed with the stock liquid that total concn is 40g/L.With furfural and dimethyl sulfoxide (DMSO) mixed solvent (v: v=1: 10) be extraction agent, be washing composition with the hexane, stock liquid, extraction agent, washing composition three's volume flow ratio is 1: 15: 5, extraction stuffing is 4mm stainless steel θ ring filler, under 40 ℃, carry out fractionation extraction, collect extraction liquid, obtain the conjugated linolic acid product through behind the vacuum concentration, product purity is 98%, and product yield is 96.7%.
Embodiment 8
Semen Maydis oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, wherein cla levels is 60%), make hybrid long chain lipid acid and be dissolved in the hexane, be mixed with the stock liquid that total concn is 40g/L.With dimethyl sulfoxide (DMSO) and dimethyl formamide mixed solvent (v: v=1: 10) be extraction agent, be washing composition with the hexane, stock liquid, extraction agent, washing composition three's volume flow ratio is 1: 16: 4, extraction stuffing is 2mm stainless steel θ ring filler, under 40 ℃, carry out fractionation extraction, collect extraction liquid, obtain the conjugated linolic acid product through behind the vacuum concentration, product purity is 96%, and product yield is 90.8%.
Embodiment 9
Safflower oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, stearic acid, palmitinic acid, wherein linoleic acid content is 81%), make hybrid long chain lipid acid and be dissolved in the heptane, be mixed with the stock liquid that total concn is 50g/L.Be extraction agent with furfural, dimethyl sulfoxide (DMSO) and N-N-methyl-2-2-pyrrolidone N-mixed solvent (v: v: v=1: 5: 5), be washing composition with the heptane, stock liquid, extraction agent, washing composition three's volume flow ratio is 2: 10: 3, extraction stuffing is 2mm stainless steel θ ring filler, under 50 ℃, carry out fractionation extraction, collect extraction liquid, obtain the linolic acid product through behind the vacuum concentration, product purity is 97%, and product yield is 95.6%.
Embodiment 10
Peanut oil is through saponification and isomerization reaction, (total fatty acid content is 99% mainly to be contained the hybrid long chain lipid acid of conjugated linolic acid, oleic acid, one acid of 20 carbon, Lignoceric acid, mountain Yu acid, eicosanoic acid, stearic acid, palmitinic acid, wherein linoleic acid content is 45%), make hybrid long chain lipid acid and be dissolved in the hexane, be mixed with the stock liquid that total concn is 60g/L.(v: v: v=1: 5: 5) is extraction agent with furfural, dimethyl sulfoxide (DMSO) and dimethyl formamide mixed solvent, be washing composition with the hexane, stock liquid, extraction agent, washing composition three's volume flow ratio is 2: 12: 4, extraction stuffing is 2mm stainless steel θ ring filler, under 50 ℃, carry out fractionation extraction, collect extraction liquid, obtain the linolic acid product through behind the vacuum concentration, product purity is 95%, and product yield is 91.8%.
Claims (6)
1. method of from hybrid long chain lipid acid, separating octadecadienoic acid, comprise: hybrid long chain lipid acid is dissolved in the washing composition, be made into stock liquid, cat head at the fractionation extraction tower feeds extraction agent, feed washing composition at the bottom of the tower, feed stock liquid in the tower, carry out fractionation extraction, collect extraction liquid, obtain octadecadienoic acid after steaming desolventizes; Described hybrid long chain lipid acid is the product that crude vegetal process saponification and isomerization reaction obtain; Described extraction agent comprises a kind of or its mixture in acetonitrile, furfural, dimethyl sulfoxide (DMSO), dimethyl formamide, N-N-methyl-2-2-pyrrolidone N-, the tetramethylene sulfone; Described washing composition is that boiling range is a kind of or its mixture in sherwood oil, hexane, heptane and the octane of 60-90 ℃ or 90-120 ℃.
2. method according to claim 1, it is characterized in that: described extraction agent is a kind of or its mixture of furfural, dimethyl sulfoxide (DMSO) and N-N-methyl-2-2-pyrrolidone N-.
3. method according to claim 1, it is characterized in that: in the fractionation extraction, the volume flow ratio of stock liquid, extraction agent, washing composition is 1-2:4-20:2-15.
4. method according to claim 1, it is characterized in that: in the stock liquid cumulative volume, the concentration of hybrid long chain lipid acid is 0.5-120g/L in the described stock liquid.
5. method according to claim 4, it is characterized in that: in the stock liquid cumulative volume, the concentration of hybrid long chain lipid acid is 20-80g/L in the described stock liquid.
6. method according to claim 1, it is characterized in that: the service temperature of fractionation extraction is 20-60 ℃.
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| CN105384635B (en) * | 2014-09-09 | 2018-03-09 | 浙江医药股份有限公司新昌制药厂 | A kind of method that the fatty-acid ethyl esters of Omega 3 are isolated and purified from fish oil |
| CN111606856B (en) * | 2020-06-08 | 2023-04-11 | 浙江大学衢州研究院 | Method for separating carnosine and histidine |
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| JP2944132B2 (en) * | 1990-03-23 | 1999-08-30 | サントリー株式会社 | Novel polyunsaturated fatty acid and method for producing the fatty acid or lipid containing the same |
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