CN114591169A - Preparation method of saturated straight-chain fatty acid butyl ester - Google Patents
Preparation method of saturated straight-chain fatty acid butyl ester Download PDFInfo
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- CN114591169A CN114591169A CN202210330156.0A CN202210330156A CN114591169A CN 114591169 A CN114591169 A CN 114591169A CN 202210330156 A CN202210330156 A CN 202210330156A CN 114591169 A CN114591169 A CN 114591169A
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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
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/60—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
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Abstract
The invention discloses a preparation method of saturated straight-chain fatty acid butyl ester, which comprises the following steps: (1) sequentially adding saturated straight-chain fatty acid and n-butyl alcohol into the reaction kettle, and adding a catalyst into the reaction material under stirring; heating to boil under stirring, keeping boiling reflux state, continuously separating water from the oil-water separator until no water is generated, stopping heating, and terminating esterification reaction; (2) adding a sodium carbonate aqueous solution into the mixed solution after the esterification reaction to obtain a mixed solution, maintaining the temperature of the mixed solution at 80-95 ℃, uniformly stirring, standing for layering, and removing a water layer to obtain a water-washed mixed solution; (3) adding pure water into the mixed solution after washing, keeping the temperature at 80-95 ℃, uniformly stirring, standing for layering, and removing a water layer to obtain the mixed solution after washing; repeating the water washing operation in the step (3) until the mixed solution is neutral after water washing; (4) and carrying out reduced pressure distillation on the mixed solution after washing to obtain a target product, namely saturated straight-chain fatty acid butyl ester.
Description
Technical Field
The invention relates to a preparation method of saturated straight-chain fatty acid butyl ester.
Background
Butyl stearate has been well established for applications in the fields of metal processing, resins, cosmetics, and the like. CN 101914015B discloses that stearic acid is esterified with n-butanol under catalysis of concentrated sulfuric acid, and water is used for washing in the water washing step, which does not consider further removal and reduction of fatty acid, thereby resulting in too high acid value and low purity of the product.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a preparation method of saturated straight-chain fatty acid butyl ester, which has high product purity and can reduce the subsequent purification process.
The technical scheme is as follows: the preparation method of the saturated straight-chain fatty acid butyl ester comprises the following steps:
(1) adding saturated straight-chain fatty acid and n-butanol into the reaction kettle in sequence, and adding a catalyst into the reaction material under stirring; heating to boil under stirring, keeping boiling reflux state, continuously separating water from the oil-water separator until no water is generated, stopping heating, and terminating esterification reaction;
(2) adding a sodium carbonate aqueous solution into the mixed solution after the esterification reaction to obtain a mixed solution, wherein the pH of the mixed solution is about 9 or more; maintaining the temperature of the mixed solution at 80-95 ℃, uniformly stirring, standing for layering, and removing a water layer to obtain a water-washed mixed solution;
(3) adding pure water into the mixed solution after washing, keeping the temperature at 80-95 ℃, uniformly stirring, standing for layering, and removing a water layer to obtain the mixed solution after washing; repeating the water washing operation of the step (3) until the mixed solution is neutral or weakly acidic after water washing; the pH value is below 8;
(4) and (4) carrying out reduced pressure distillation on the mixed solution after washing to obtain a target product, namely saturated straight-chain fatty acid butyl ester.
Wherein in the step (1), the carbon chain length of the saturated straight chain fatty acid is 20-24; the catalyst is one of concentrated sulfuric acid, p-toluenesulfonic acid or sulfamic acid.
Wherein in the step (1), the molar ratio of the saturated straight-chain fatty acid to the n-butyl alcohol is 1: 1.5-3.0; the molar ratio of the saturated straight-chain fatty acid to the catalyst is 1: 0.005-0.03.
Wherein in the step (2), the mass percentage concentration of the sodium carbonate aqueous solution is 1-10%. Too low or too high a concentration of the aqueous sodium carbonate solution may result in incomplete neutralization of the acid or a severe excess of sodium carbonate.
Wherein, in the step (3), the pH value of the mixed solution after water washing is 6-7.
Has the advantages that: the C20-C24 straight-chain fatty acid butyl ester has high melting point and is easy to be precipitated as a solid at normal temperature, so that the temperature is controlled to be 80-95 ℃ during washing, and the problem of product precipitation is avoided; the sodium carbonate aqueous solution is used for the first washing, so that the acid catalyst can be effectively neutralized, and meanwhile, the fatty acid salt is obtained; secondly, the temperature is controlled to be 80-95 ℃ all the time in the washing process (the temperature is too low, the removal of fatty acid is not facilitated, the solubility of sodium fatty acid at high temperature is good), the extraction of unreacted fatty acid by high-temperature alkaline water is facilitated, the unreacted saturated straight-chain fatty acid is effectively removed, the acid value of the product fatty acid butyl ester is reduced, the purity of the product fatty acid butyl ester is improved, the subsequent purification process is reduced, and the product does not need the subsequent purification process and also has high purity.
Drawings
FIG. 1 is an infrared spectrum of the product butyl eicosanoate obtained in example 1;
FIG. 2 is an infrared spectrum of butyl tetracosanoate of the product obtained in example 2.
Detailed Description
Example 1
The preparation method of the saturated straight-chain fatty acid butyl ester comprises the following steps:
(1) sequentially adding 312kg of eicosanoic acid, 150kg of n-butanol and 3.12kg of sulfamic acid into a 200-liter reaction kettle with a stirring device, a heating device, a temperature control device, a water circulation condenser and an oil-water separator; heating the mixture under stirring until the reaction solution boils, keeping the boiling reflux state, continuously separating water from the oil-water separator until no water is generated, stopping heating, and finishing the esterification reaction;
(2) controlling the temperature of the reaction kettle at 95 ℃, adding 300kg of sodium carbonate aqueous solution with the mass concentration of 5% into the reaction kettle, stirring for 10min, standing for layering, and draining a water layer to obtain a mixed solution after washing;
(3) adding 300kg of pure water into the mixed solution after washing, stirring for 10min, standing for layering, and draining the water layer; repeating the step (3) and the water washing step for 3-4 times until the pH value of the mixed solution after water washing is 6-7;
(4) and (3) distilling the mixture containing the n-butyl alcohol after washing under reduced pressure to obtain the high-purity butyl eicosanoate which is a bright yellow oily substance and a yellow waxy solid at normal temperature, and measuring the melting point of the product to be 36.2 ℃, so that the yield of the product butyl eicosanoate is calculated to be more than 95% and the purity is calculated to be more than 99%. The acid value of the product obtained in example 1 was 0.20 mgKOH/g.
Example 2
The preparation method of the saturated straight-chain fatty acid butyl ester comprises the following steps:
(1) 368g of tetracosanoic acid, 150kg of n-butanol and 3.68kg of p-toluenesulfonic acid are sequentially added into a 200-liter reaction kettle with a stirring device, a heating device, a temperature control device, a water circulation condenser and an oil-water separator; heating the mixture under stirring until the reaction solution boils, keeping the boiling reflux state, continuously separating water from the oil-water separator until no water is generated, stopping heating, and finishing the esterification reaction;
(2) controlling the temperature at 95 ℃, adding 300kg of sodium carbonate aqueous solution with the mass concentration of 5% into the reaction kettle, stirring for 10min, standing for layering, and draining a water layer to obtain a mixed solution after washing;
(3) adding 300kg of pure water into the mixed solution after washing, stirring for 10min, standing for layering, and draining the water layer; repeating the step (3) and the water washing step for 3-4 times until the pH value of the mixed solution after water washing is 6-7;
(4) and (3) carrying out reduced pressure distillation on the mixture containing the n-butyl alcohol after washing to obtain a bright yellow oily substance which is a yellow waxy solid at normal temperature, wherein the melting point of the product is 50.3 ℃, and thus the yield of the butyl tetracosanoate product is more than 95% and the purity is more than 99%. The acid value of the product obtained in example 2 was 0.25 mgKOH/g.
Claims (5)
1. A preparation method of saturated straight-chain fatty acid butyl ester is characterized by comprising the following steps:
(1) adding saturated straight-chain fatty acid and n-butanol into the reaction kettle in sequence, and adding a catalyst into the reaction material under stirring; heating to boil under stirring, keeping boiling reflux state, continuously separating water from the oil-water separator until no water is generated, stopping heating, and terminating esterification reaction;
(2) adding a sodium carbonate aqueous solution into the mixed solution after the esterification reaction to obtain a mixed solution, maintaining the temperature of the mixed solution at 80-95 ℃, uniformly stirring, standing for layering, and removing a water layer to obtain a water-washed mixed solution;
(3) adding pure water into the mixed solution after washing, keeping the temperature at 80-95 ℃, uniformly stirring, standing for layering, and removing a water layer to obtain the mixed solution after washing; repeating the water washing operation in the step (3) until the mixed solution is neutral after water washing;
(4) and (4) carrying out reduced pressure distillation on the mixed solution after washing to obtain a target product, namely saturated straight-chain fatty acid butyl ester.
2. The method for producing saturated straight-chain fatty acid butyl ester according to claim 1, characterized in that: in the step (1), the carbon chain length of the saturated straight chain fatty acid is 20-24; the catalyst is one of concentrated sulfuric acid, p-toluenesulfonic acid or sulfamic acid.
3. The method for producing saturated straight-chain fatty acid butyl ester according to claim 1, characterized in that: in the step (1), the molar ratio of saturated straight-chain fatty acid to n-butyl alcohol is 1: 1.5-3.0; the molar ratio of the saturated straight-chain fatty acid to the catalyst is 1: 0.005-0.03.
4. The method for producing saturated straight-chain fatty acid butyl ester according to claim 1, characterized in that: in the step (2), the mass percentage concentration of the sodium carbonate aqueous solution is 1-10%.
5. The method for producing saturated straight-chain fatty acid butyl ester according to claim 1, characterized in that: in the step (3), the pH value of the mixed solution after water washing is 6-7.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB642718A (en) * | 1942-10-24 | 1950-09-13 | Severoceske Tukova Zd Y Drive | Process for the esterification of fatty acids with low-molecular univalent alcohols |
| WO1999024387A1 (en) * | 1997-11-10 | 1999-05-20 | The Procter & Gamble Company | A process for making high purity fatty acid lower alkyl esters |
| CN101906035A (en) * | 2010-08-28 | 2010-12-08 | 天津市化学试剂研究所 | Refining method of high-purity butyl stearate |
| CN103450015A (en) * | 2013-09-06 | 2013-12-18 | 郑桂富 | Synthetic method of tri-n-butyl citrate |
| CN105777465A (en) * | 2016-04-08 | 2016-07-20 | 于迎春 | Rapid washing technology in production process of synthetic ester |
| CN111269113A (en) * | 2018-12-04 | 2020-06-12 | 上海凯赛生物技术股份有限公司 | Method for treating mixture containing long-chain dibasic acid, dibutyl long-chain dibasic acid mixture and application thereof |
-
2022
- 2022-03-31 CN CN202210330156.0A patent/CN114591169A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB642718A (en) * | 1942-10-24 | 1950-09-13 | Severoceske Tukova Zd Y Drive | Process for the esterification of fatty acids with low-molecular univalent alcohols |
| WO1999024387A1 (en) * | 1997-11-10 | 1999-05-20 | The Procter & Gamble Company | A process for making high purity fatty acid lower alkyl esters |
| CN101906035A (en) * | 2010-08-28 | 2010-12-08 | 天津市化学试剂研究所 | Refining method of high-purity butyl stearate |
| CN103450015A (en) * | 2013-09-06 | 2013-12-18 | 郑桂富 | Synthetic method of tri-n-butyl citrate |
| CN105777465A (en) * | 2016-04-08 | 2016-07-20 | 于迎春 | Rapid washing technology in production process of synthetic ester |
| CN111269113A (en) * | 2018-12-04 | 2020-06-12 | 上海凯赛生物技术股份有限公司 | Method for treating mixture containing long-chain dibasic acid, dibutyl long-chain dibasic acid mixture and application thereof |
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