CN101760327A - Method for preparing nervonic acid by taking colza oil containing nervonic acid as raw material - Google Patents
Method for preparing nervonic acid by taking colza oil containing nervonic acid as raw material Download PDFInfo
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- CN101760327A CN101760327A CN201010300713A CN201010300713A CN101760327A CN 101760327 A CN101760327 A CN 101760327A CN 201010300713 A CN201010300713 A CN 201010300713A CN 201010300713 A CN201010300713 A CN 201010300713A CN 101760327 A CN101760327 A CN 101760327A
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- acid
- selacholeic
- selacholeic acid
- nervonic acid
- obtains
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- GWHCXVQVJPWHRF-KTKRTIGZSA-N (15Z)-tetracosenoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-KTKRTIGZSA-N 0.000 title claims abstract description 200
- 238000000034 method Methods 0.000 title claims abstract description 32
- XJXROGWVRIJYMO-SJDLZYGOSA-N Nervonic acid Natural products O=C(O)[C@@H](/C=C/CCCCCCCC)CCCCCCCCCCCC XJXROGWVRIJYMO-SJDLZYGOSA-N 0.000 title abstract description 15
- GWHCXVQVJPWHRF-UHFFFAOYSA-N cis-tetracosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCCCCCC(O)=O GWHCXVQVJPWHRF-UHFFFAOYSA-N 0.000 title abstract description 15
- 239000002994 raw material Substances 0.000 title abstract description 10
- 235000006008 Brassica napus var napus Nutrition 0.000 title abstract 7
- 240000000385 Brassica napus var. napus Species 0.000 title 1
- 238000002425 crystallisation Methods 0.000 claims abstract description 82
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 34
- 239000000194 fatty acid Substances 0.000 claims abstract description 34
- 229930195729 fatty acid Natural products 0.000 claims abstract description 34
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 32
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000000470 constituent Substances 0.000 claims description 54
- 230000008025 crystallization Effects 0.000 claims description 53
- 239000002253 acid Substances 0.000 claims description 49
- 235000019484 Rapeseed oil Nutrition 0.000 claims description 43
- 239000000706 filtrate Substances 0.000 claims description 40
- 150000002632 lipids Chemical class 0.000 claims description 32
- 238000009835 boiling Methods 0.000 claims description 29
- 238000001816 cooling Methods 0.000 claims description 28
- 239000012043 crude product Substances 0.000 claims description 28
- 238000000967 suction filtration Methods 0.000 claims description 28
- 239000012065 filter cake Substances 0.000 claims description 26
- 238000004519 manufacturing process Methods 0.000 claims description 24
- 239000000047 product Substances 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 20
- 230000007062 hydrolysis Effects 0.000 claims description 18
- 238000006460 hydrolysis reaction Methods 0.000 claims description 18
- 238000001035 drying Methods 0.000 claims description 16
- 239000000413 hydrolysate Substances 0.000 claims description 14
- 239000000843 powder Substances 0.000 claims description 14
- 238000001291 vacuum drying Methods 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000000199 molecular distillation Methods 0.000 claims description 9
- 235000019198 oils Nutrition 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- 238000007670 refining Methods 0.000 claims description 2
- 230000008521 reorganization Effects 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000006228 supernatant Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 abstract description 26
- -1 carbon chain fatty acids Chemical class 0.000 abstract description 8
- 238000002360 preparation method Methods 0.000 abstract description 6
- 244000060924 Brassica campestris Species 0.000 abstract 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 239000012153 distilled water Substances 0.000 description 24
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 23
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 23
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000005406 washing Methods 0.000 description 15
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 12
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 12
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 12
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 12
- 239000005642 Oleic acid Substances 0.000 description 12
- 235000021355 Stearic acid Nutrition 0.000 description 12
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 12
- 239000012535 impurity Substances 0.000 description 12
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 12
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 12
- 229920006395 saturated elastomer Polymers 0.000 description 12
- 239000008117 stearic acid Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 7
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 4
- 229960004756 ethanol Drugs 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 210000003792 cranial nerve Anatomy 0.000 description 3
- ZYNDJIBBPLNPOW-UHFFFAOYSA-N eurucic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCCCCCC(=O)OC ZYNDJIBBPLNPOW-UHFFFAOYSA-N 0.000 description 3
- 230000010365 information processing Effects 0.000 description 3
- 150000004668 long chain fatty acids Chemical class 0.000 description 3
- ZYNDJIBBPLNPOW-KHPPLWFESA-N methyl erucate Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(=O)OC ZYNDJIBBPLNPOW-KHPPLWFESA-N 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 241000251730 Chondrichthyes Species 0.000 description 2
- 108090000862 Ion Channels Proteins 0.000 description 2
- 102000004310 Ion Channels Human genes 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 241000219226 Acer truncatum Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001561070 Macaranga Species 0.000 description 1
- 241000928579 Malania oleifera Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 210000004958 brain cell Anatomy 0.000 description 1
- 230000004641 brain development Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000010773 plant oil Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Abstract
The invention discloses a method for preparing nervonic acid by taking colza oil containing the nervonic acid as the raw material, relates to a method for preparing nervonic acid and aims to provide a method for preparing nervonic acid by taking colza oil containing the nervonic acid as the raw material, which has the advantages of easy obtainment of the raw material, simple process, greatly reduced cost and high product quality purity. The invention has the technical scheme that the colza oil is hydrolyzed under high pressure to obtain mixed fatty acid, then the fatty acid is rectified to obtain crude nervonic acid, and finally the crude nervonic acid is crystallized via an organic solvent to obtain more than 95wt% of nervonic acid product and other long carbon chain fatty acids. The method increases the types of deeply processed colza oil products, and adopts a solvent crystallization method to purify the nervonic acid from the long carbon chain fatty acids, thereby increasing the value of the colza oil products. Compared with a conventional nervonic acid preparation process, the method reduces the cost and sources of the nervonic acid. The invention is mainly applied for extracting the nervonic acid from the colza oil.
Description
Technical field
The present invention relates to a kind of preparation method of Selacholeic acid, particularly relate to a kind of utilization and be rich in the method for the rapeseed oil of Selacholeic acid for the feedstock production Selacholeic acid.
Background technology
Selacholeic acid (nervonic acid) formal name used at school is: 15-tetracosenoic acid, molecular formula are C
24H
46O
2, skeleton symbol is CH
3(CH
2)
7CH=CH (CH
2)
13COOH, molecular weight are 366.6, and pure product are the white needles solid at normal temperatures, are a kind of ω-9 type long-chain monoenoic fatty acids.Because of it is separated from shark brain, ox brain the earliest, so have another name called shark acid (selacholeicacid).
The essential nutrition that Selacholeic acid is brain development, keep enlivens, prevents that to what improve cranial nerve encephalasthenia from playing a very important role.Human thinking, memory, issue an order etc. all be unable to do without information transmission and information processing, and brain cell membrane plays crucial effect in information transmission and information processing.Cranial nerve cell is finished information transmission and information processing by ionic channel on its film and acceptor.Selacholeic acid is the important component part of cranial nerve cell film, and ionic channel and acceptor are played important regulatory role.
Production of Selacholeic acid at present and research mainly concentrate on the animal and plant oil plant that is rich in Selacholeic acid and extract and purification, and this class raw material mainly comprises malania oleifera, scute Macaranga fruit, Acertruncatum Bunge oil, and wherein Selacholeic acid content is about 5%.Though in these raw materials, contain a certain amount of Selacholeic acid, can satisfy the 90wt% purity of using but want to bring up to, need remove other fatty acid material by multistep, and the non-Selacholeic acid material of removing during the course is difficult to obtain utilize, and causes the production cost of Selacholeic acid high.These raw materials are difficult for obtaining simultaneously, have also restricted the extraction and the application of Selacholeic acid.
Containing the Selacholeic acid rapeseed oil is a kind of rapeseed oil that is rich in long chain fatty acid, and wherein content of erucic acid can reach more than the 45wt%, the about 0.5～1wt% of the content of Selacholeic acid.Rape is extensively planted in China as a kind of traditional oil crops, the production capacity of rapeseed oil is huge, so adopting rapeseed oil is that raw material can make a large amount of Selacholeic acids and the erucic acid of high added value, thereby promote greatly developing of rapeseed oil deep processing and Selacholeic acid healthcare products industry.
Summary of the invention
The purpose of this invention is to provide that a kind of present method raw material is easy to get, and technology is easy to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, cost significantly reduces and quality product purity height.
The objective of the invention is to realize by following technical proposal: a kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) the rapeseed oil hydrolysis prepares lipid acid:
To contain the hydrolysis under the condition of 200～280 ℃ of temperature, pressure 3.5～5.5MPa of Selacholeic acid rapeseed oil, after hydrolysis finishes hydrolysate be moved into the separating funnel layering, and get supernatant liquid and be mixed fatty acid;
(2) separation of lipid acid:
Mixed fatty acid carries out rectifying under the condition of 180～230 ℃ of pressure 50～100Pa, temperature, the light constituent that obtains is lower boiling lipid acid, reorganization is divided into high boiling point lipid acid, heavy constituent are carried out molecular distillation or rectifying under the condition of 160～200 ℃ of temperature, pressure 5～10Pa, the gained heavy constituent are the Selacholeic acid crude product;
(3) Selacholeic acid is refining:
1: 3～1: 7 fully be dissolved in organic solvent by mass ratio the Selacholeic acid crude product, slowly temperature control to 10 ℃～0 ℃ carries out crystallisation by cooling one time, crystallization finishes after suction filtration separates, gained filtrate is Selacholeic acid solution, again filtrate temperature control to 0 ℃～15 ℃ is carried out the secondary crystallisation by cooling, crystallization finishes after suction filtration separates, and the filter cake that obtains is Selacholeic acid, the Selacholeic acid drying that obtains is removed organic solvent, promptly get the Selacholeic acid product of white powder.
Among the above-mentioned preparation method, the Selacholeic acid in the described step (3) is that drying at room temperature removes organic solvent in vacuum drying oven.
Among the above-mentioned preparation method, described organic solvent is sherwood oil, normal hexane or ethanol.
From method feature of the present invention as can be seen, the invention has the advantages that: separate long chain fatty acid in the rapeseed oil by the mode of molecular distillation or rectifying, increased the product category of rapeseed oil deep processing, adopt the solvent crystallization Selacholeic acid of from long chain fatty acid, purifying simultaneously, thereby improved the value of the product of rapeseed oil.Compare with traditional Selacholeic acid preparation technology simultaneously, this technology has reduced the cost and the source of Selacholeic acid product.That is to say that preparation method's raw material of the present invention is easy to get, cost is low, suitable operation, and product Selacholeic acid purity height is for the suitability for industrialized production of Selacholeic acid has been opened up economically viable production route.
Embodiment
The present invention is described further below by embodiment:
Embodiment 1
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 2000ml autoclave, add 800g and contain Selacholeic acid rapeseed oil, 20g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 240～245 ℃ of temperature, pressure 4.8MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 720g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 180～185 ℃ of pressure 50Pa, temperature of the 720g mixed fatty acid that obtains, the 370g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 350g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.
In the device of belt stirrer, water trap and condenser, add 350g heavy constituent, 5g phospho-wolframic acid, 350g methyl alcohol,, vacuumize separating methanol obtain fatty acid methyl esters 364g after reaction finishes 60～100 ℃ of reactions 4～8 hours.Fatty acid methyl ester adopts molecular distillation to distill under the condition of 160～165 ℃ of temperature, pressure 5Pa, obtains being rich in the light constituent 348g of methyl erucate, and 16g content 46.5wt% Selacholeic acid methyl esters.
In the time of 60～80 ℃, 16g Selacholeic acid methyl esters is adopted the KOH ethanolic soln saponification of 3wt%, when PH＞13, finish reaction.The dilute sulphuric acid that adds 10wt% then is acidified to PH＜3, and the liquid after the acidifying is moved in the separating funnel, and the washing layering is collected the upper strata oily liquids and promptly got Selacholeic acid crude product 15g.
(3) 15g Selacholeic acid crude product fully is dissolved in the sherwood oil (60～90 ℃ of boiling ranges) by mass ratio at 1: 5, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 3g of saturated acid and impurity, and filtrate is Selacholeic acid solution.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 10 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 9g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 9g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 2 hours, promptly get the Selacholeic acid product 8g of white powder, analyze to such an extent that its Selacholeic acid content is 95.2wt%.
Embodiment 2
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 2000ml autoclave, add 800g and contain Selacholeic acid rapeseed oil, 20g distilled water, nitrogen replacement 2～5 times, stirring reaction is 6 hours under the condition of 200～205 ℃ of temperature, pressure 3.5MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 718g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 200～205 ℃ of pressure 70Pa, temperature of the 718g mixed fatty acid that obtains, the 372g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 346g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.
In the device of belt stirrer, water trap and condenser, add 346g heavy constituent, 5g phospho-wolframic acid, 350g methyl alcohol,, vacuumize separating methanol obtain fatty acid methyl esters 366g after reaction finishes 60～100 ℃ of reactions 4～8 hours.Fatty acid methyl ester adopts molecular distillation to distill under the condition of 1750～180 ℃ of temperature, pressure 7.5Pa, obtains being rich in the light constituent 342g of methyl erucate, and 15g content 46.3wt% Selacholeic acid methyl esters.
In the time of 60～80 ℃, 15g Selacholeic acid methyl esters is adopted the KOH ethanolic soln saponification of 3wt%, when PH＞13, finish reaction.The dilute sulphuric acid that adds 10wt% then is acidified to PH＜3, and the liquid after the acidifying is moved in the separating funnel, and the washing layering is collected the upper strata oily liquids and promptly got Selacholeic acid crude product 14.2g.
(3) 14.2g Selacholeic acid crude product fully is dissolved in the normal hexane by mass ratio at 1: 3, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 4 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 3.1g of saturated acid and impurity, and filtrate is Selacholeic acid solution.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 10 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 8.8g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 8.8g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 2 hours, promptly get the Selacholeic acid product 7.9g of white powder, analyze to such an extent that its Selacholeic acid content is 95.1wt%.
Embodiment 3
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 2000ml autoclave, add 800g and contain Selacholeic acid rapeseed oil, 20g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 270～280 ℃ of temperature, pressure 5.5MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 710g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 220～230 ℃ of pressure 100Pa, temperature of the 710g mixed fatty acid that obtains, the 366g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 344g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.
In the device of belt stirrer, water trap and condenser, add 344g heavy constituent, 5g phospho-wolframic acid, 350g methyl alcohol,, vacuumize separating methanol obtain fatty acid methyl esters 364g after reaction finishes 60～100 ℃ of reactions 4～8 hours.Fatty acid methyl ester adopts molecular distillation to distill under the condition of 195～200 ℃ of temperature, pressure 10Pa, obtains being rich in the light constituent 346g of methyl erucate, and 15.2g content 43.8wt% Selacholeic acid methyl esters.
In the time of 60～80 ℃, 16g Selacholeic acid methyl esters is adopted the KOH ethanolic soln saponification of 3wt%, when PH＞13, finish reaction.The dilute sulphuric acid that adds 10wt% then is acidified to PH＜3, and the liquid after the acidifying is moved in the separating funnel, and the washing layering is collected the upper strata oily liquids and promptly got Selacholeic acid crude product 13.8g.
(3) 13.8g Selacholeic acid crude product fully is dissolved in the ethanol by mass ratio at 1: 7, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 8 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 3.1g of saturated acid and impurity, and filtrate is Selacholeic acid solution.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 10 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 8.6g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 8.6g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 2 hours, promptly get the Selacholeic acid product 7.7g of white powder, analyze to such an extent that its Selacholeic acid content is 95.0wt%.
Embodiment 4:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 2000ml autoclave, add 500g and contain Selacholeic acid rapeseed oil, 10g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 240～245 ℃ of temperature, pressure 4.8MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 450g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 180～185 ℃ of pressure 50Pa, temperature of the 450g mixed fatty acid that obtains, the 230g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 220g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out rectifying with rectifying tower under the condition of 160～165 ℃ of temperature, pressure 5Pa, obtain being rich in the light constituent 209g of erucic acid, and 11g content 47.6wt% Selacholeic acid crude product.
(3) 11g Selacholeic acid crude product fully is dissolved in the normal hexane by mass ratio at 1: 5, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 4 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 2g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 10 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 6g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 6g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 2.5 hours, promptly get the Selacholeic acid product 5.3g of white powder, analyze to such an extent that its Selacholeic acid content is 97.4wt%.
Embodiment 5:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 2000ml autoclave, add 500g and contain Selacholeic acid rapeseed oil, 10g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 200～205 ℃ of temperature, pressure 3.5MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 450g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 200～205 ℃ of pressure 70Pa, temperature of the 450g mixed fatty acid that obtains, the 232g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 218g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out rectifying with rectifying tower under the condition of 1750～180 ℃ of temperature, pressure 7.5Pa, obtain being rich in the light constituent 210g of erucic acid, and 10.8g content 47wt% Selacholeic acid crude product.
(3) 10.8g Selacholeic acid crude product fully is dissolved in the ethanol by mass ratio at 1: 3, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 4 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 2.2g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 10 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 5.8g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 5.8g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 2.5 hours, promptly get the Selacholeic acid product 5g of white powder, analyze to such an extent that its Selacholeic acid content is 96.7wt%.
Embodiment 6:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 2000ml autoclave, add 500g and contain Selacholeic acid rapeseed oil, 10g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 270～280 ℃ of temperature, pressure 5.5MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 445g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 220～230 ℃ of pressure 100Pa, temperature of the 445g mixed fatty acid that obtains, the 232g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 213g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out rectifying with rectifying tower under the condition of 190～200 ℃ of temperature, pressure 10Pa, obtain being rich in the light constituent 203g of erucic acid, and 10g content 46.2wt% Selacholeic acid crude product.
(3) 10g Selacholeic acid crude product fully is dissolved in the sherwood oil by mass ratio at 1: 7, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 4 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 1.9g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 10 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 5.9g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 5.9g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 2.5 hours, promptly get the Selacholeic acid product 5.2g of white powder, analyze to such an extent that its Selacholeic acid content is 96.1wt%.
Embodiment 7:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 1000ml autoclave, add 500g and contain Selacholeic acid rapeseed oil, 10g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 250～255 ℃ of temperature, pressure 5.2MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 450g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 190～195 ℃ of pressure 60Pa, temperature of the 450g mixed fatty acid that obtains, 230 light constituents that obtain are lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 220g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out molecular distillation under the condition of 160～165 ℃ of temperature, pressure 5Pa, obtain being rich in the light constituent 210g of erucic acid, and 10g content 47.0wt% Selacholeic acid crude product.
(3) 10g Selacholeic acid crude product fully is dissolved in the normal hexane by mass ratio at 1: 3, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 2g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 12 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 6.5g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 6.5g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 4 hours, promptly get the Selacholeic acid product 5.8g of white powder, analyze to such an extent that its Selacholeic acid content is 96.2wt%.
Embodiment 8:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 1000ml autoclave, add 500g and contain Selacholeic acid rapeseed oil, 10g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 200～205 ℃ of temperature, pressure 3.8MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 446g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 180～185 ℃ of pressure 80Pa, temperature of the 446g mixed fatty acid that obtains, 225 light constituents that obtain are lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 221g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out molecular distillation under the condition of 170～175 ℃ of temperature, pressure 8Pa, obtain being rich in the light constituent 211g of erucic acid, and 10g content 47.1wt% Selacholeic acid crude product.
(3) 10g Selacholeic acid crude product fully is dissolved in the sherwood oil by mass ratio at 1: 4, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 2g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 12 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 6.6g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 6.6g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 4 hours, promptly get the Selacholeic acid product 5.8g of white powder, analyze to such an extent that its Selacholeic acid content is 96.8wt%.
Embodiment 9:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 1000ml autoclave, add 500g and contain Selacholeic acid rapeseed oil, 10g distilled water, nitrogen replacement 2～5 times, stirring reaction is 8 hours under the condition of 270～275 ℃ of temperature, pressure 4.4MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 440g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 210～220 ℃ of pressure 90Pa, temperature of the 440g mixed fatty acid that obtains, 223 light constituents that obtain are lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 217g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out molecular distillation under the condition of 190～195 ℃ of temperature, pressure 9Pa, obtain being rich in the light constituent 208g of erucic acid, and 9g content 46.3wt% Selacholeic acid crude product.
(3) 9g Selacholeic acid crude product fully is dissolved in the ethanol by mass ratio at 1: 6, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 2g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 12 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 6.3g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 6.3g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 4 hours, promptly get the Selacholeic acid product 5.4g of white powder, analyze to such an extent that its Selacholeic acid content is 95.3wt%.
Embodiment 10:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 1000ml autoclave, add 250g and contain Selacholeic acid rapeseed oil, 5g distilled water, nitrogen replacement 2～5 times, stirring reaction is 10 hours under the condition of 250～255 ℃ of temperature, pressure 5.0MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 225g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 180～190 ℃ of pressure 60Pa, temperature of the 225g mixed fatty acid that obtains, the 115g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 110g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out rectifying with rectifying tower under the condition of 160～165 ℃ of temperature, pressure 5.5Pa, obtain being rich in the light constituent 105g of erucic acid, and 5g content 47.6wt% Selacholeic acid crude product.
(3) 5g Selacholeic acid crude product fully is dissolved in the dehydrated alcohol by mass ratio at 1: 5, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 1g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 12 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 3g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 3g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 5 hours, promptly get the Selacholeic acid product 2.3g of white powder, analyze to such an extent that its Selacholeic acid content is 95.5wt%.
Embodiment 11:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 1000ml autoclave, add 250g and contain Selacholeic acid rapeseed oil, 5g distilled water, nitrogen replacement 2～5 times, stirring reaction is 10 hours under the condition of 210～215 ℃ of temperature, pressure 4MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 222g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 200～205 ℃ of pressure 800Pa, temperature of the 222g mixed fatty acid that obtains, the 116g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 106g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out rectifying with rectifying tower under the condition of 170～175 ℃ of temperature, pressure 7.5Pa, obtain being rich in the light constituent 101g of erucic acid, and 5g content 46.7wt% Selacholeic acid crude product.
(3) 5g Selacholeic acid crude product fully is dissolved in the sherwood oil by mass ratio at 1: 3, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 1g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 12 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 3.1g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 3.1g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 5 hours, promptly get the Selacholeic acid product 2.5g of white powder, analyze to such an extent that its Selacholeic acid content is 95.7wt%.
Embodiment 12:
A kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, comprise the following steps:
(1) in the 1000ml autoclave, add 250g and contain Selacholeic acid rapeseed oil, 5g distilled water, nitrogen replacement 2～5 times, stirring reaction is 10 hours under the condition of 270～275 ℃ of temperature, pressure 5.0MPa.After hydrolysis finishes hydrolysate is moved into the separating funnel layering, add distilled water washing 2～3 times, collect the upper strata oily liquids, obtain the 228g mixed fatty acid.
(2) with the rectifying in the rectifying tower of 220～230 ℃ of pressure 95Pa, temperature of the 228g mixed fatty acid that obtains, the 116g light constituent that obtains is lower boiling lipid acid (as stearic acid, oleic acid, palmitinic acid etc.), and the 112g heavy constituent are the high boiling point lipid acid that is rich in erucic acid, Selacholeic acid.Heavy constituent are carried out rectifying with rectifying tower under the condition of 190～195 ℃ of temperature, pressure 9Pa, obtain being rich in the light constituent 106g of erucic acid, and 6g content 47.6wt% Selacholeic acid crude product.
(3) 6g Selacholeic acid crude product fully is dissolved in the normal hexane by mass ratio at 1: 7, slow temperature control to 10 ℃～0 ℃ of crystallisation by cooling, crystallization time is 5 hours.Crystallization finishes after suction filtration separates, and obtains being rich in the filter cake 1.2g of saturated acid and impurity, and filtrate is Selacholeic acid.With filtrate temperature control to 0 ℃～-15 ℃ of crystallisation by cooling, crystallization time is 12 hours again, and crystallization finishes after suction filtration separates, and obtains filter cake 3.2g and is Selacholeic acid, and filtrate is reclaimed solvent and utilized.The 3.2g Selacholeic acid drying at room temperature in vacuum drying oven that obtains was removed solvent in 5 hours, promptly get the Selacholeic acid product 2.5g of white powder, analyze to such an extent that its Selacholeic acid content is 95.9wt%.
Disclosed all features in this specification sheets, or the step in disclosed all methods or the process except mutually exclusive feature and/or step, all can make up by any way.
Disclosed arbitrary feature in this specification sheets (comprising any accessory claim, summary and accompanying drawing) is unless special narration all can be replaced by other equivalences or the alternative features with similar purpose.That is, unless special narration, each feature is an example in a series of equivalences or the similar characteristics.
The present invention is not limited to aforesaid embodiment.The present invention expands to any new feature or any new combination that discloses in this manual, and the arbitrary new method that discloses or step or any new combination of process.
Claims (3)
1. one kind to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, it is characterized in that comprising the following steps:
(1) the rapeseed oil hydrolysis prepares lipid acid:
To contain the hydrolysis under the condition of 200～280 ℃ of temperature, pressure 3.5～5.5MPa of Selacholeic acid rapeseed oil, after hydrolysis finishes hydrolysate be moved into the separating funnel layering, and get supernatant liquid and be mixed fatty acid;
(2) separation of lipid acid:
Mixed fatty acid carries out rectifying under the condition of 180～230 ℃ of pressure 50～100Pa, temperature, the light constituent that obtains is lower boiling lipid acid, reorganization is divided into high boiling point lipid acid, heavy constituent are carried out molecular distillation or rectifying under the condition of 160～200 ℃ of temperature, pressure 5～10Pa, the gained heavy constituent are the Selacholeic acid crude product;
(3) Selacholeic acid is refining:
1: 3～1: 7 fully be dissolved in organic solvent by mass ratio the Selacholeic acid crude product, slowly temperature control to 10 ℃～0 ℃ carries out crystallisation by cooling one time, crystallization finishes after suction filtration separates, gained filtrate is Selacholeic acid solution, again filtrate temperature control to 0 ℃～-15 ℃ is carried out the secondary crystallisation by cooling, crystallization finishes after suction filtration separates, and the filter cake that obtains is Selacholeic acid, the Selacholeic acid drying that obtains is removed organic solvent, promptly get the Selacholeic acid product of white powder.
2. according to claim 1 a kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, it is characterized in that Selacholeic acid is that drying at room temperature removes organic solvent in vacuum drying oven in the described step (3).
3. according to claim 1 and 2 a kind of to contain the method that the Selacholeic acid rapeseed oil is the feedstock production Selacholeic acid, it is characterized in that described organic solvent is sherwood oil, normal hexane or ethanol.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102787020A (en) * | 2012-07-17 | 2012-11-21 | 诸暨兴绿油脂有限公司 | Process for producing fatty acid special for rubber emulsification with hogwash oil as raw material |
| CN104073364A (en) * | 2014-07-22 | 2014-10-01 | 中南林业科技大学 | Technology for preparing lauric acid by adopting litsea cubeba kernel oil |
| CN107445826A (en) * | 2017-07-25 | 2017-12-08 | 天津泽达天健科技有限公司 | A kind of preparation method of neural acid esters |
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| CN108802246A (en) * | 2018-06-08 | 2018-11-13 | 禾大西普化学（四川）有限公司 | A kind of nervonic acid process for separation and purification |
| CN112174811A (en) * | 2020-08-27 | 2021-01-05 | 菏泽中禾健元生物科技有限公司 | High-efficiency high-purity extraction process of nervonic acid, namely cis-15-tetracosenic acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102787020A (en) * | 2012-07-17 | 2012-11-21 | 诸暨兴绿油脂有限公司 | Process for producing fatty acid special for rubber emulsification with hogwash oil as raw material |
| CN102787020B (en) * | 2012-07-17 | 2014-12-17 | 诸暨兴绿油脂有限公司 | Process for producing fatty acid special for rubber emulsification with hogwash oil as raw material |
| CN104073364A (en) * | 2014-07-22 | 2014-10-01 | 中南林业科技大学 | Technology for preparing lauric acid by adopting litsea cubeba kernel oil |
| CN107445826A (en) * | 2017-07-25 | 2017-12-08 | 天津泽达天健科技有限公司 | A kind of preparation method of neural acid esters |
| CN108391819A (en) * | 2018-01-18 | 2018-08-14 | 浙江健智元生物科技有限公司 | A kind of health products preparation method and its health products improving brain neuroblastoma |
| CN108802246A (en) * | 2018-06-08 | 2018-11-13 | 禾大西普化学（四川）有限公司 | A kind of nervonic acid process for separation and purification |
| CN108802246B (en) * | 2018-06-08 | 2021-04-23 | 禾大西普化学（四川）有限公司 | Nervonic acid separating and purifying method |
| CN112174811A (en) * | 2020-08-27 | 2021-01-05 | 菏泽中禾健元生物科技有限公司 | High-efficiency high-purity extraction process of nervonic acid, namely cis-15-tetracosenic acid |
| CN114874851A (en) * | 2022-04-24 | 2022-08-09 | 中国科学院植物研究所 | Method for separating nervonic acid from acer truncatum seed oil |
| CN114874851B (en) * | 2022-04-24 | 2024-01-12 | 中国科学院植物研究所 | Method for separating nervonic acid from acer truncatum seed oil |
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