CN107445826A - A kind of preparation method of neural acid esters - Google Patents
A kind of preparation method of neural acid esters Download PDFInfo
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- CN107445826A CN107445826A CN201710612402.0A CN201710612402A CN107445826A CN 107445826 A CN107445826 A CN 107445826A CN 201710612402 A CN201710612402 A CN 201710612402A CN 107445826 A CN107445826 A CN 107445826A
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- acid esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The present invention relates to a kind of preparation method of neural acid esters, comprise the following steps：Using supercritical CO2Malania Oleifera Oil in fluid extraction malania oleifera；Obtained Malania Oleifera Oil is carried out to aquation degumming, saponification and acid adding processing, isolated fatty acid mixed successively；Obtained fatty acid mixed is obtained into thick nervonic acid by low temperature crystallization in organic solvent；Obtained thick nervonic acid is esterified to obtain thick neural acid esters；Obtained thick neural acid esters is subjected to molecular distillation, isolated high-purity nerve acid esters.The present invention is pollution-free, product yield is high, solves and prepares the problems such as resource utilization existing for neural acid esters is low, product yield is low, dissolvent residual pollution in the prior art.
Description
Technical field
The present invention relates to chemical field, and in particular to a kind of preparation method of neural acid esters.
Background technology
Nervonic acid also known as Nervonic Acid, the entitled nervonie acid of chemistry, is a kind of long-chain monounsaturated fatty acid
Acid, molecular formula C24H46O2, relative molecular mass 366.6, it is at normal temperatures white plates crystal, alcohol can be dissolved in, do not dissolved in
Water, 39-40 DEG C of fusing point.Nervonic acid (NA) be scientists from all over the world generally acknowledge can repair dredging injured brain nerve pathway（It is i.e. neural
Fiber）And promote the economic benefits and social benefits material of nerve cell regeneration, it is the core natural component of cerebral nerve fiber and nerve cell.Nerve
The shortage of acid will cause cerebral apoplexy sequela, such as senile dementia, brain paralysis, encephalatrophy, failure of memory, insomnia forgetfulness brain disease
Disease.And human body itself is difficult synthesis nervonic acid, it is necessary to is supplemented by food intake.The country extracts separation from vegetable oil at present
The method of nervonic acid mainly has metal salts as precipitator, tydrophilization method, soap column chromatography, solvent crystallization and molecule to steam
Evaporate method etc..There is the problems such as resource utilization is low, product yield is low, dissolvent residual pollution in above method, and nervonic acid is by carrying
The problems such as resource utilization that is esterified to obtain neural acid esters after pure again is low, product yield is low, dissolvent residual pollution will more
Substantially.
The content of the invention
It is an object of the invention to provide a kind of preparation method of neural acid esters, to solve to prepare neural acid esters in the prior art
The problems such as existing resource utilization is low, product yield is low, dissolvent residual pollution.
In order to solve the above technical problems, the technical solution adopted in the present invention is：A kind of preparation method of neural acid esters, bag
Include following steps：
（1）Using supercritical CO2Malania Oleifera Oil in fluid extraction malania oleifera；
（2）By step（1）Obtained Malania Oleifera Oil carries out aquation degumming, saponification and acid adding processing successively, isolated mixed
Close aliphatic acid；
（3）By step（2）Obtained fatty acid mixed obtains thick nervonic acid by low temperature crystallization in organic solvent；
（4）By step（3）Obtained thick nervonic acid is esterified to obtain thick neural acid esters；
（5）By step（4）Obtained thick neural acid esters carries out molecular distillation, isolated high-purity nerve acid esters.
Further, step（1）Extraction step is：To being extracted after malania oleifera shelling, section, extraction temperature 40-50
DEG C, extracting pressure 15-25MPa, extraction time 1-3 hours, faint yellow Malania Oleifera Oil is obtained by extraction.
Further, step（2）The operating procedure of middle aquation degumming is：In step（1）Added in obtained Malania Oleifera Oil
60-80 DEG C of warm water heating stirring, salt is added according to oil foot amount, the addition of salt is the 4-5% of oil foot quality, stands and divides
From oil foot, the Malania Oleifera Oil after degumming is obtained.
Further, step（2）The operating procedure of middle saponification is：Hydrogen is added in Malania Oleifera Oil after aquation degumming
The ethanol solution of sodium oxide molybdena or potassium hydroxide, saponification is heated to reflux to without oil droplet, obtains mixing-in fat hydrochlorate.
Further, step（2）Middle acid adding processing and separation application are：The mixing-in fat obtained after saponification
Hydrochloric acid or sulfuric acid solution regulation pH to 2-3 are added in hydrochlorate；Upper oil reservoir is obtained with petroleum ether extraction, decompression steaming petroleum ether must mix
Close aliphatic acid.
Further, step（3）Described organic solvent be it is a kind of in ethanol, acetone, n-hexane, petroleum ether and gasoline or
Several mixtures, crystallization temperature are-10-0 DEG C.
Further, step（4）Operating procedure be：By step（3）Obtained thick nervonic acid is in 60-80 DEG C, acid bar
It is heated to reflux under part with methanol or ethanol, esterification 1-10 hours, obtains thick neural acid esters.
Further, step（4）Middle acid condition refers to be dissolved with H2SO4 in methanol or ethanol.
Further, step（5）Operating procedure be：By step（4）Obtained thick neural acid esters carries out many-level molecule steaming
Cut from；First order thin film evaporation, vacuum 1000Pa, temperature are 70-80 DEG C；One-level heavy constituent carries out second level molecule steaming
Evaporate, vacuum 10-100Pa, temperature is 120-150 DEG C, isolated C14-C20 fatty acid esters and two level heavy constituent C22-
C24 fatty acid esters；C22-C24 aliphatic acid carries out third level molecular distillation, vacuum 1-10Pa, and temperature is 180-200 DEG C, is obtained
To the neural acid esters that mass fraction is more than 85%.
Beneficial effect：The present invention uses the malania oleifera rich in nervonic acid to use the supercritical CO without entrainer for raw material2Stream
Body abstraction technique obtains Malania Oleifera Oil, and the technology efficient cryogenic is pollution-free；It is more easy to through fatty acid mixed obtained by aquation degumming tech
Crystallization Separation is carried out in the solvent, excludes the possibility that colloidal particles wrap up neural acid crystal；Thick nervonic acid after esterification,
Purified to thick neural acid esters, product yield is high；It is pure using one-level thin film evaporation and the method for two-stage molecular distillation, separation
Change obtains more than 85% neural acid ester product of mass fraction and byproduct " biodiesel ", has resource utilization height, product yield
The characteristics of height, no solvent residue.
Specific embodiment
With reference to specific embodiment, the present invention will be further described in detail.
Embodiment 1：
（1）It will shell, the malania oleifera 5.0kg after section is fitted into 20L extraction kettles and extracted, 40 DEG C of extraction temperature, extracting pressure
15MPa, extraction time 2h, obtain faint yellow Malania Oleifera Oil 2.3kg；（2）60-80 DEG C of warm water is added in faint yellow Malania Oleifera Oil to stir
Mix, thin salt is added according to oil foot amount, the addition of salt is the 4-5% of oil foot quality, standing separation oil foot, after obtaining degumming
Malania Oleifera Oil；The ethanol solution of potassium hydroxide is added in Malania Oleifera Oil after degumming, saponification is heated to reflux to without oil droplet, obtains
To mixing-in fat hydrochlorate；Hydrochloric acid solution regulation pH to 2 is added in mixing-in fat hydrochlorate；Upper oil reservoir is obtained with petroleum ether extraction,
Decompression steaming petroleum ether obtains fatty acid mixed 1.5kg；（3）Fatty acid mixed uses 15 times of amounts（Refer to the 15 of fatty acid mixed quality
Times）Ethanol dissolves by heating, and is transferred in 0 DEG C of ice bath, stands overnight, and filters to obtain thick nervonic acid 1.0kg；（4）Add in thick nervonic acid
Enter excess ethyl alcohol acid solution（Refer to and dissolve sulfuric acid etc. in ethanol）, esterification 5h is carried out in 80 DEG C of water-baths, obtains thick nerve
Acid esters；（5）By reaction solution（Thick neural acid esters）Carry out multiple-grade molecular distillation separation；First order thin film evaporation, distillation pressure（I.e.
Vacuum）For 1000Pa, 75 DEG C of vapo(u)rizing temperature, ethanol is reclaimed；Second level molecular distillation, distillation pressure 20-100Pa, distillation
140 DEG C of temperature, isolated C14-C20Fatty acid ester（Accessory substance biodiesel）With two level heavy constituent C22-C24Fatty acid ester；
C22-C24Aliphatic acid carries out third level molecular distillation, distillation pressure 5-10Pa, 180 DEG C of vapo(u)rizing temperature, collects three-level light component
0.77kg, detect mass fraction be 85% neural acetoacetic ester.
Embodiment 2：
（1）Will shell, section after malania oleifera 5.0kg be fitted into 20L extraction kettles, 45 DEG C, extracting pressure 15MPa of extraction temperature,
Extraction time 2h, obtain faint yellow Malania Oleifera Oil 2.4kg；（2）60-80 DEG C of warm water stirring, root are added in faint yellow Malania Oleifera Oil
Salt is added according to oil foot amount, the addition of salt is the 4-5% of oil foot quality, standing separation oil foot, obtains the malania oleifera after degumming
Oil；Malania Oleifera Oil after degumming adds sodium hydroxide ethanol solution, is heated to reflux saponification to without oil droplet, obtains fatty acid mixed
Salt；Hydrochloric acid solution regulation pH to 2 is added in mixing-in fat hydrochlorate；Upper oil reservoir is obtained with petroleum ether extraction, decompression boils off oil
Ether obtains fatty acid mixed 1.6kg；（3）Fatty acid mixed uses 20 times of amounts（Refer to 20 times of fatty acid mixed quality）Acetone soln adds
Heat of solution, it is transferred in -5 DEG C of ice baths, stands overnight, filters to obtain thick nervonic acid 1.2kg；（4）Excessive first is added in thick nervonic acid
Alkyd solution, esterification 10h is carried out in 80 DEG C of water-baths, obtain thick neural acid esters；（5）Reaction solution（Thick neural acid esters）Enter
Row multiple-grade molecular distillation separates；First order thin film evaporation, distillation pressure 1000Pa, 75 DEG C of vapo(u)rizing temperature, reclaim methanol；Second
Level molecular distillation, distillation pressure 80-100Pa, 140 DEG C of vapo(u)rizing temperature, isolated C14-C20Fatty acid ester and two level heavy constituent
C22-C24Fatty acid ester；C22-C24Aliphatic acid carries out third level molecular distillation, distillation pressure 5-8Pa, 180 DEG C of vapo(u)rizing temperature, collects
Three-level light component 0.81kg, detect mass fraction be 87% nervonic acid methyl esters.
Embodiment 3：
（1）Will shell, section after malania oleifera 5.0kg be fitted into 20L extraction kettles, 50 DEG C, extracting pressure 20MPa of extraction temperature,
Extraction time 3h, obtain faint yellow Malania Oleifera Oil 2.6kg；（2）60-80 DEG C of warm water stirring, root are added in faint yellow Malania Oleifera Oil
Salt is added according to oil foot amount, the addition of salt is the 4-5% of oil foot quality, standing separation oil foot, obtains the malania oleifera after degumming
Oil；Malania Oleifera Oil after degumming adds sodium hydroxide ethanol solution, is heated to reflux saponification to without oil droplet, obtains fatty acid mixed
Salt；Sulfuric acid solution regulation pH to 3 is added in mixing-in fat hydrochlorate；Upper oil reservoir is obtained with petroleum ether extraction, decompression boils off oil
Ether obtains fatty acid mixed 1.8kg；（3）Fatty acid mixed uses 25 times of amounts（Refer to 25 times of fatty acid mixed quality）N-hexane it is molten
Liquid dissolves by heating, and is transferred in -10 DEG C of ice baths, stands overnight, and filters to obtain thick nervonic acid 1.3kg；（4）Added in thick nervonic acid
Glycollic acid solution is measured, esterification 10h is carried out in 80 DEG C of water-baths, obtains thick neural acid esters；（5）Reaction solution（Thick nervonic acid
Ester）Carry out multiple-grade molecular distillation separation；First order thin film evaporation, distillation pressure 1000Pa, 75 DEG C of vapo(u)rizing temperature, reclaim ethanol；
Second level molecular distillation, distillation pressure 20-40Pa, 150 DEG C of vapo(u)rizing temperature, isolated C14-C20Fatty acid ester and two level restructuring
Divide C22-C24Fatty acid ester；C22-C24Aliphatic acid carries out third level molecular distillation, distillation pressure 1-5Pa, 190 DEG C of vapo(u)rizing temperature, receives
Collect three-level light component 0.96kg, detect mass fraction be 88% neural acetoacetic ester.
Above example be only to the present invention design be illustrated, it is any do not depart from present inventive concept in the case of
Made replacement or improvement all should include protection scope of the present invention.
Claims (9)
1. a kind of preparation method of neural acid esters, it is characterised in that comprise the following steps：
（1）Using supercritical CO2Malania Oleifera Oil in fluid extraction malania oleifera；
（2）By step（1）Obtained Malania Oleifera Oil carries out aquation degumming, saponification and acid adding processing successively, isolated mixed
Close aliphatic acid；
（3）By step（2）Obtained fatty acid mixed obtains thick nervonic acid by low temperature crystallization in organic solvent；
（4）By step（3）Obtained thick nervonic acid is esterified to obtain thick neural acid esters；
（5）By step（4）Obtained thick neural acid esters carries out molecular distillation, isolated neural acid esters.
A kind of 2. preparation method of neural acid esters according to claim 1, it is characterised in that step（1）Extraction step is：
To being extracted after malania oleifera shelling, section, 40-50 DEG C of extraction temperature, extracting pressure 15-25MPa, extraction time 1-3 hours,
Faint yellow Malania Oleifera Oil is obtained by extraction.
A kind of 3. preparation method of neural acid esters according to claim 1, it is characterised in that step（2）Middle aquation degumming
Operating procedure be：In step（1）60-80 DEG C of warm water heating stirring is added in obtained Malania Oleifera Oil, is added according to oil foot amount
Enter salt, the addition of salt is the 4-5% of oil foot quality, standing separation oil foot, obtains the Malania Oleifera Oil after degumming.
A kind of 4. preparation method of neural acid esters according to claim 1, it is characterised in that step（2）Middle saponification
Operating procedure be：The ethanol solution of sodium hydroxide or potassium hydroxide is added in Malania Oleifera Oil after aquation degumming, is heated back
Saponification is flowed to without oil droplet, obtains mixing-in fat hydrochlorate.
A kind of 5. preparation method of neural acid esters according to claim 4, it is characterised in that step（2）Middle acid adding processing
And separation application is：Hydrochloric acid or sulfuric acid solution regulation pH to 2- are added in the mixing-in fat hydrochlorate obtained after saponification
3；Upper oil reservoir is obtained with petroleum ether extraction, decompression steaming petroleum ether obtains fatty acid mixed.
A kind of 6. preparation method of neural acid esters according to claim 1, it is characterised in that：Step（3）Described is organic
Solvent is mixtures one or more of in ethanol, acetone, n-hexane, petroleum ether and gasoline, and crystallization temperature is-10-0 DEG C.
A kind of 7. preparation method of neural acid esters according to claim 1, it is characterised in that step（4）Operating procedure
For：By step（3）Obtained thick nervonic acid is heated to reflux under 60-80 DEG C, acid condition with methanol or ethanol, esterification 1-
10 hours, obtain thick neural acid esters.
A kind of 8. preparation method of neural acid esters according to claim 7, it is characterised in that step（4）Middle acid condition
Refer to be dissolved with H in methanol or ethanol2SO4。
A kind of 9. preparation method of neural acid esters according to claim 1, it is characterised in that step（5）Operating procedure
For：By step（4）Obtained thick neural acid esters carries out multiple-grade molecular distillation separation；First order thin film evaporation, vacuum are
1000Pa, temperature are 70-80 DEG C；One-level heavy constituent carries out second level molecular distillation, vacuum 10-100Pa, temperature 120-
150 DEG C, isolated C14-C20Fatty acid ester and two level heavy constituent C22-C24Fatty acid ester；C22-C24Aliphatic acid carries out the third level
Molecular distillation, vacuum 1-10Pa, temperature are 180-200 DEG C, obtain the neural acid esters that mass fraction is more than 85%.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112048384A (en) * | 2020-09-16 | 2020-12-08 | 甘肃金荞芙农林资源科技有限公司 | Preparation method of sea buckthorn fruit oil flavor and sodium carboxylate and fruit flavor type furan flavor |
| CN112110814A (en) * | 2020-09-28 | 2020-12-22 | 成都乾元投资管理有限公司 | Nervonic acid extraction device |
| CN112391420A (en) * | 2020-11-05 | 2021-02-23 | 南京康齐生物科技有限公司 | Method for extracting high-purity nervonic acid in garlic fruit oil |
| CN112521280A (en) * | 2021-01-14 | 2021-03-19 | 兰州理工大学 | Method for extracting nervonic acid from xanthoceras sorbifolia bunge oil based on molecular distillation technology |
| CN112939761A (en) * | 2021-03-05 | 2021-06-11 | 贵州精萃生物科技有限公司 | Method for extracting nervonic acid |
| CN116425629A (en) * | 2023-03-24 | 2023-07-14 | 中国农业科学院农产品加工研究所 | Preparation method of resveratrol nervonate |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112048384A (en) * | 2020-09-16 | 2020-12-08 | 甘肃金荞芙农林资源科技有限公司 | Preparation method of sea buckthorn fruit oil flavor and sodium carboxylate and fruit flavor type furan flavor |
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| CN112939761A (en) * | 2021-03-05 | 2021-06-11 | 贵州精萃生物科技有限公司 | Method for extracting nervonic acid |
| CN112939761B (en) * | 2021-03-05 | 2023-10-20 | 贵州精萃生物科技有限公司 | Method for extracting nervonic acid |
| CN116425629A (en) * | 2023-03-24 | 2023-07-14 | 中国农业科学院农产品加工研究所 | Preparation method of resveratrol nervonate |
| CN116425629B (en) * | 2023-03-24 | 2023-10-24 | 中国农业科学院农产品加工研究所 | Preparation method of resveratrol nervonate |
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Effective date of registration: 20180213 Address after: 300450 Tianjin Binhai New Area Binhai Science Park hi-tech No. six Road 39 9-3-301 Applicant after: BINHAI INDUSTRIAL TECHNOLOGY RESEARCH INSTITUTE OF ZHEJIANG UNIVERSITY Applicant after: Tianjin Zeda Tianjian Technology Co Ltd Address before: 300450 Tianjin Binhai New Area Kangtai Road No. 59 Green Valley Health Industrial Park No. 24 building two layer Applicant before: Tianjin Zeda Tianjian Technology Co Ltd |
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