CN114907402B - Synthesis of organic phosphine fatty acid type ionic liquid and application of organic phosphine fatty acid type ionic liquid in vitamin A palmitate separation process - Google Patents

Synthesis of organic phosphine fatty acid type ionic liquid and application of organic phosphine fatty acid type ionic liquid in vitamin A palmitate separation process Download PDF

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CN114907402B
CN114907402B CN202210492549.1A CN202210492549A CN114907402B CN 114907402 B CN114907402 B CN 114907402B CN 202210492549 A CN202210492549 A CN 202210492549A CN 114907402 B CN114907402 B CN 114907402B
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ionic liquid
fatty acid
acid
vitamin
palmitate
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CN114907402A (en
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石森
孙媛媛
曾雄伟
阮勇哲
杨蕊
丁志勇
李盼
刘佳旭
杨颖�
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Wanhua Chemical Sichuan Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/5018—Cycloaliphatic phosphines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/12—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
    • C07C53/126—Acids containing more than four carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/505—Preparation; Separation; Purification; Stabilisation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
    • 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 invention provides synthesis of an organic phosphonic fatty acid ionic liquid and application thereof in a vitamin A palmitate separation process. The synthesis of the ionic liquid takes dicyclohexylphosphine and C12-18 saturated or unsaturated fatty acid as raw materials for reaction. The application in the separation process of the vitamin A palmitate is as follows: filtering VA palmitate reaction liquid to remove a catalyst, adding an ionic liquid, standing for layering, collecting lower-layer liquid, cooling to-20 ℃, crystallizing and separating out vitamin A palmitate, and filtering to obtain the high-purity vitamin A palmitate. The ionic liquid can be repeatedly used for more than 10 times, and the separation effect is not reduced. When separating the vitamin A palmitate, the method has the remarkable advantages of simple separation process, high product yield, high purity, no extra solvent except ionic liquid, environmental protection and energy conservation.

Description

Synthesis of organic phosphine fatty acid type ionic liquid and application of organic phosphine fatty acid type ionic liquid in vitamin A palmitate separation process
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to preparation of an organic phosphine fatty acid ionic liquid and application of the organic phosphine fatty acid ionic liquid in vitamin A palmitate prepared by a separation enzyme catalysis method.
Background
The ionic liquid is a recognized green solvent and has the advantages of low melting point, wide liquid range, good ionic conductivity and thermal conductivity, high thermal stability and the like. The excellent characteristics make the catalyst widely applied in the organic synthesis and separation process, can obviously reduce the reaction conditions, reduce the separation difficulty, improve the solvent recycling rate and reduce the generation of three wastes.
Vitamin A is fat-soluble vitamin, is widely applied to non-prescription drugs, nutritional supplements, feed additives and food industry, is vitamin A palmitate applied to the fields of food and the like, is produced by taking vitamin A acetate as a raw material and adopting an enzyme catalysis method in the current industrial production, has the characteristics of mild reaction conditions, high conversion rate and few byproducts, mainly adopts the processes of repeated recrystallization, extraction, concentration and the like of organic solvents for separation, consumes a large amount of solvents, has complex separation process and generates more three wastes. Under the current new chemical forms of energy conservation, emission reduction and consumption reduction, development of an environment-friendly and low-energy-consumption separation process is needed, so that sustainable long-term development of the product is realized.
The use of ionic liquids is less in advance of the application of ionic liquids in fat-soluble vitamin products, and the advantages of ionic liquids in the separation process of fat-soluble vitamins are to be deeply mined. Patent CN111087335a discloses a method for preparing retinoic acid by oxidizing retinol using bis- (3-methyl-1-imidazole) ethylene tetrafluoroborate ionic liquid as a solvent system, wherein the ionic liquid is used as a reaction system, the reaction is performed under mild conditions, and the retinoic acid is prepared in high yield, but the patent only uses the ionic liquid as the reaction system, belongs to more conventional application, does not involve a separation process, and has insufficient application excavation on the ionic liquid. Patent CN105418575a discloses a process for separating vitamin E by using an alkyl imidazole type ionic liquid, wherein the process uses the ionic liquid as an extractant to extract and separate vitamin E from raw materials, and then uses an organic solvent to perform two-step back extraction, thereby obtaining vitamin E with high yield. The patent uses ionic liquid for separating vitamin E, but the process is complicated, and organic solvent is needed for separation in the later period, so that the generation of three wastes is not reduced, and the advantages of the ionic liquid are not fully utilized.
Disclosure of Invention
The invention mainly aims to provide a novel ionic liquid and application of the ionic liquid in the process of separating fat-soluble vitamin A palmitate.
The invention realizes the aim by the following technical scheme:
an organic phosphine fatty acid type ionic liquid has the following structure:
wherein R is a group derived from a C12-18 saturated or unsaturated fatty acid, preferably any one of lauric acid, myristic acid, linoleic acid, stearic acid, palmitic acid, and linolenic acid, except for the carboxyl group.
The synthesis of the ionic liquid takes dicyclohexylphosphine and C12-18 saturated or unsaturated fatty acid as raw materials, and the synthesis method comprises the following steps:
s1: mixing dicyclohexylphosphine and C12-18 saturated or unsaturated fatty acid according to equimolar amount at 18-22deg.C under nitrogen atmosphere, adding alkane solvent 1-3 times of the total mass of the mixture, wherein the alkane solvent can be selected from one of n-pentane, n-hexane, n-heptane and n-octane, preferably n-hexane;
s2: cooling to 5-10 ℃, maintaining the temperature and stirring for 2-4 hours at the rotating speed of 200-400rpm, then recovering to 18-22 ℃, standing until the liquid is layered, separating and collecting the lower liquid, namely the organic phosphonic fatty acid type ionic liquid. The yield is above 98%.
In the preparation method, the saturated or unsaturated fatty acid of the reaction raw material C12-18 is preferably one of lauric acid, myristic acid, linoleic acid, stearic acid, palmitic acid and linolenic acid.
The invention also relates to the separation of the vitamin A palmitate by using the obtained ionic liquid, and the separation process comprises the following steps:
s1: the VAP solution obtained by the chemical or enzymatic reaction is filtered to remove the catalyst, and the filtrate is collected.
S2: adding 1-3 times of ionic liquid into the filtrate, maintaining 15-20 ℃, stirring for 0.5-2 hours at the rotating speed of 100-200rpm, standing for layering after stopping, and collecting the lower solution.
S3: cooling the lower layer solution to-20 to-25 ℃, standing for 30-60 minutes, completely separating out solids, and filtering and collecting the solids to obtain the vitamin A palmitate high-purity product. The separation yield is more than 97%. The detection purity is greater than 1.75MIU. The filtrate is ionic liquid, can be reused for more than ten times, and the separation yield is not reduced basically.
In the separation process, filtering is performed by using filter cloth with a pore diameter of 1500-500 meshes, preferably 1000 meshes, and the material can be selected from one of PVC, PE, PP and nylon.
The invention has the beneficial effects that:
the invention provides a novel ionic liquid which is simple in synthesis process and high in yield. The method is applied to the separation process of the vitamin A palmitate, can greatly simplify the separation process, reduce the use of solvents, reduce the energy consumption, and can repeatedly use the ionic liquid, thereby reducing the yield of three wastes. The yield of the vitamin A palmitate is high and the purity of the product is high.
Detailed Description
In the following examples and comparative examples, the separation apparatus used was as follows:
the device comprises a positive-huge 1L positive-pressure filter, a 3L three-neck flask, a Shanghai essence macro water bath kettle, a 1L separating funnel and a Zhengzhou great wall department industry and trade DL400 circulating cooler.
The reagents, sources and purities used were as follows:
dicyclohexylphosphine, analytically pure, purchased from Guozhen, n-hexane, analytically pure, purchased from Guozhen,
lauric acid, linoleic acid, stearic acid, palmitic acid, analytically pure, purchased from chinese medicine,
vitamin a alcohol, 95%, purchased from aladine,
immobilized lipase 435, enzyme activity 10000u/g, available from NoveXin,
palmitic acid, superior pure, purchased from aladine.
The filter cloth is 1500 meshes, 1000 meshes, 800 meshes and 500 meshes, and is made of PVC, PE, PP and nylon respectively and purchased from Hebei Jingshui environmental protection technology Co.
The vitamin a palmitate reaction solution was prepared as the separation raw material in the examples according to the following process:
weighing vitamin A alcohol and palmitic acid according to the equimolar amount, adding the vitamin A alcohol and the palmitic acid into a three-neck flask, adding 3 times of normal hexane solvent, then adding 3% of immobilized enzyme 435 in mass percent, charging nitrogen, maintaining the nitrogen atmosphere, starting stirring, keeping at 200-400rpm, heating to 35 ℃, reacting for 3 hours, stopping, filtering to remove enzyme catalyst, and obtaining the normal hexane solution of the VAP, wherein the VAP content is 23.5%.
Example 1
Synthesis of ionic liquid A
200g of dicyclohexylphosphine and 200g of lauric acid are respectively weighed under the nitrogen atmosphere at 20 ℃, added into a 3L three-neck flask, 800g of normal hexane is added, magnetons are added, the temperature is reduced to 5 ℃, stirring is started, the stirring is maintained at 200rpm for 2 hours, then the stirring is stopped, the temperature is restored to 20 ℃, the reaction solution is transferred into a separating funnel, the reaction solution is kept stand until the solution is completely layered, the lower solution is separated, and the ionic liquid dicyclohexylphosphine laurate is synthesized, the mass is 394g, and the yield is 98.5%.
Example 2
Synthesis of ionic liquid B
200g of dicyclohexylphosphine and 256g of palmitic acid are respectively weighed under the nitrogen atmosphere at the temperature of 19 ℃, added into a 3L three-neck flask, 456g of n-heptane is added, the magneton is added, the temperature is reduced to 8 ℃, stirring is started, the stirring is maintained at 300rpm for 4 hours, then the stirring is stopped, the temperature is restored to 20 ℃, the reaction solution is transferred into a separating funnel, the reaction solution is kept stand until the solution is completely layered, the lower solution is separated, and the ionic liquid dicyclohexyl phosphine palmitate is synthesized, the mass is 451g, and the yield is 98.9%.
Example 3
Synthesis of ionic liquid C
200g of dicyclohexylphosphine and 284g of stearic acid are respectively weighed under the nitrogen atmosphere at the temperature of 21 ℃, are added into a 3L three-neck flask, 1452g of n-octane is added, the magneton is added, the temperature is reduced to 10 ℃, stirring is started, the stirring is maintained at 400rpm for 3 hours, the stirring is stopped, the temperature is restored to 22 ℃, the reaction solution is transferred into a separating funnel, the reaction solution is kept stand until the solution is completely layered, the lower solution is separated, and the synthesized ionic liquid dicyclohexylphosphine stearate has the mass of 479g and the yield of 98.97%.
Example 4
Separation effect of ionic liquid a for vitamin a palmitate:
200g of vitamin A palmitate reaction solution is taken, 200g of ionic liquid A is added, the temperature is maintained at 20 ℃, stirring is carried out for 1 hour at the rotation speed of 100rpm, standing and layering are carried out after stopping, and the lower layer solution is collected. Cooling the lower layer solution to-20 ℃, standing for 30 minutes, completely precipitating solids, and filtering and collecting the solids by using a 500-mesh nylon filter cloth to obtain 47.1g of vitamin A palmitate high-purity product with the separation yield of 99.18% (47.1 x 0.556 x 1.78/(0.235 x 200)). The purity was 1.78MIU.
Example 5
Separation effect of ionic liquid B on vitamin A palmitate
150g of vitamin A palmitate reaction solution is taken, 300g of ionic liquid B is added, 15 ℃ is maintained, stirring is carried out for 2 hours at 200rpm, standing and layering are carried out after stopping, and the lower solution is collected. Cooling the lower layer solution to-25 ℃, standing for 60 minutes, completely precipitating the solid, and filtering and collecting the solid by using 1500-mesh PVC filter cloth to obtain 35g of vitamin A palmitate high-purity product, wherein the separation yield is 99.37%. The purity was 1.80MIU.
Example 6
Separation effect of ionic liquid C on vitamin A palmitate
220g of reaction solution containing vitamin A palmitate is taken, 660g of ionic liquid C is added, 18 ℃ is maintained, stirring is carried out for 0.5 hour at the rotation speed of 150rpm, standing and layering are carried out after stopping, and the lower solution is collected. Cooling the lower layer solution to-20 ℃, standing for 40 minutes, completely precipitating the solid, and filtering and collecting the solid by using 1000-mesh PE filter cloth to obtain 49.5g of vitamin A palmitate high-purity product with the separation yield of 98.5%. The purity was 1.85MIU.
Example 7
Recovery and use yield investigation of ionic liquid
The ionic liquid A synthesized in the example 1 is used for repeated use investigation, 100g of the ionic liquid A is added each time, 20 ℃ is maintained, stirring is carried out for 1 hour at the rotation speed of 100rpm, then standing and layering are carried out, the lower solution is collected, the lower solution is cooled to-20 ℃, standing is carried out for 40 minutes, solids are separated out, the solids are collected by filtration through a 1000-mesh PE filter cloth, the filtered filtrate is repeatedly used for 15 times, the separation conditions are completely the same, and the separation yield and the product purity of each use are shown in the following table.
Comparative example
Traditional vitamin A palmitate separation process without using ionic liquid
100g of reaction solution containing vitamin A palmitate is taken, firstly cooled to-10 ℃, kept at 200rpm and stirred for 4 hours, then rapidly filtered at low temperature, the filtrate is collected, distilled for 2 hours at 35 ℃ under reduced pressure, and the solvent is evaporated to dryness, thus obtaining about 25g of concentrate. The concentrate was dissolved in 150g of absolute ethanol, kept at 25 ℃, stirred at 200rpm for 4 hours to obtain a uniform solution, maintained at 200rpm and rapidly cooled to-20 ℃ for 2 hours, then rapidly filtered, and the total solid was collected to 20g, which was purified vitamin a palmitate, the isolation yield was 80.9%, and the product purity was 1.71MIU.

Claims (11)

1. An organic phosphine fatty acid type ionic liquid has the following structure:
wherein R is a radical derived from a saturated or unsaturated fatty acid of C12-18.
2. The organophosphonic fatty acid type ionic liquid according to claim 1, wherein R is selected from any one of lauric acid, myristic acid, linoleic acid, stearic acid, palmitic acid, linolenic acid, other than carboxyl group.
3. A method of preparing the ionic liquid of claim 1 or 2, comprising the steps of:
s1: mixing dicyclohexylphosphine and C12-18 saturated or unsaturated fatty acid in nitrogen atmosphere at 18-22 deg.C, and adding alkane solvent;
s2: cooling to 5-10deg.C, maintaining the temperature, stirring at 200-400rpm for 2-4 hr, recovering to 18-22deg.C, standing until the liquid is layered, separating and collecting the lower liquid to obtain organic phosphonic fatty acid type ionic liquid.
4. The method according to claim 3, wherein the C12-18 saturated or unsaturated fatty acid is one of lauric acid, myristic acid, linoleic acid, stearic acid, palmitic acid and linolenic acid.
5. The process according to claim 3 or 4, wherein dicyclohexylphosphine and C12-18 saturated or unsaturated fatty acid are mixed in equimolar amounts.
6. The method according to claim 3, wherein the alkane solvent is one selected from the group consisting of n-pentane, n-hexane, n-heptane and n-octane.
7. The process according to claim 6, wherein the alkane solvent is added in an amount of 1 to 3 times the total mass of dicyclohexylphosphine and C12-18 saturated or unsaturated fatty acid.
8. Use of an organophosphonic fatty acid-type ionic liquid according to any one of claims 1-2, for the isolation of vitamin a palmitate.
9. The use according to claim 8, comprising the steps of:
s1: filtering VAP solution obtained by chemical method or enzyme catalysis reaction to remove catalyst, and collecting filtrate;
s2: adding ionic liquid into the filtrate, maintaining the temperature at 15-20 ℃, stirring for 0.5-2 hours at the rotating speed of 100-200RPM, standing for layering after stopping, and collecting the lower solution;
s3: and cooling the lower layer solution to-25 to-20 ℃, maintaining for 30-60 minutes, completely separating out solids, and then filtering and collecting the solids to obtain the vitamin A palmitate.
10. Use according to claim 9, characterized in that the ionic liquid is added in an amount of 1-3 times the mass of the filtrate.
11. The use according to claim 9 or 10, wherein the filtration uses a filter cloth with a pore size in the range of 1500-500 mesh, and the material is any one of PVC, PE, PP and nylon.
CN202210492549.1A 2022-05-07 2022-05-07 Synthesis of organic phosphine fatty acid type ionic liquid and application of organic phosphine fatty acid type ionic liquid in vitamin A palmitate separation process Active CN114907402B (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102424662A (en) * 2011-09-28 2012-04-25 集美大学 Separation and purification method for vitamin A palmitate
CN103254160A (en) * 2013-05-20 2013-08-21 东北制药集团股份有限公司 Method for separating and purifying vitamin C palmitate from reaction liquid of direct esterification method

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102424662A (en) * 2011-09-28 2012-04-25 集美大学 Separation and purification method for vitamin A palmitate
CN103254160A (en) * 2013-05-20 2013-08-21 东北制药集团股份有限公司 Method for separating and purifying vitamin C palmitate from reaction liquid of direct esterification method

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Krech, F. et al.Correlation of Tolman's cone angles with 1J(31P-1H) values of phosphonium fluorosulfonates.Zeitschrift fuer Anorganische und Allgemeine Chemie.1978,第440卷45-51. *

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