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Method for preparing fatty acid methyl ester sulphonic salt with low-disodium salt content by using earlier sulfonation and later esterification technique

A technology of fatty acid methyl ester sulfonate and its manufacturing method, which is applied in the fields of sulfonate preparation and organic chemistry, and can solve the problems of α-sulfo fatty acid without breakthrough progress, lack of countermeasures and systematic research, etc., and achieve product quality Good, the effect of reducing separation steps and shortening the process

Inactive Publication Date: 2009-01-14
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there has been no breakthrough in the esterification of α-sulfo fatty acids, and there is still a lack of countermeasures and systematic research on how to use the first sulfonation and then esterification process to manufacture high-quality MES

Method used

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  • Method for preparing fatty acid methyl ester sulphonic salt with low-disodium salt content by using earlier sulfonation and later esterification technique
  • Method for preparing fatty acid methyl ester sulphonic salt with low-disodium salt content by using earlier sulfonation and later esterification technique

Examples

Experimental program
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Effect test

Embodiment 1 12

[0017] Example 1 Synthesis of sodium dodecanoic acid methyl sulfonate

[0018] In a 250mL reaction device with heating, stirring and temperature control system, 28g (0.1mol) of α-sulfododecanoic acid prepared by sulfonation was added, and the molar ratio of α-sulfo fatty acid: methanol = 1:30 Add 96g (3mol) of methanol to the system, reflux for 10h; then use H in the methanol solution phase 2 O 2 Bleach until the Klett color is not greater than 50; continue to massage the molar ratio of sodium hydroxide:α-methyl sulfododecanoate=1:1 in the methanol solution phase and add dropwise a 20% mass fraction of sodium hydroxide methanol solution to the system, Neutralize at room temperature, adjust the pH of the system to 7; remove the methanol by rotary evaporation to obtain 31.8 g of sodium dodecanoate sulfonate product, in which the content of the active ester sodium salt is 93.6%, and the content of the disodium salt is less than 0.5%.

Embodiment 2 12

[0019] Example 2 Synthesis of sodium dodecanoic acid methyl sulfonate

[0020] In a 500L reaction device with heating, stirring and temperature control system, add 56kg (0.2kmol) of α-sulfododecanoic acid prepared by sulfonation in advance, molar ratio α-sulfododecanoic acid: methanol=1 :40 Add 256kg (8kmol) of methanol to the system, reflux for 7h; then use H in the methanol solution phase 2 O 2 Bleach until the Klett color is not greater than 50; continue to massage the molar ratio of sodium hydroxide:α-methyl sulfododecanoate = 1:1 into the system by adding 10% mass fraction of methanol solution of sodium hydroxide, Neutralize at 30°C, adjust the system pH to 7.5; evaporate and remove methanol to obtain 63.6 kg of sodium dodecanoate sulfonate product, in which the content of the active ester sodium salt is 92.8%, and the content of the disodium salt is less than 0.5%.

Embodiment 3 16

[0021] Example 3 Synthesis of sodium hexadecanoic acid methyl sulfonate

[0022] In a 250mL reaction device with heating, stirring and temperature control system, 33.6g (0.1mol) of α-sulfohexadecanoic acid prepared by sulfonation was added, and the molar ratio of α-sulfohexadecanoic acid: methanol = 1:20 Add 64g (2mol) of methanol to the system, reflux for 6h; then use H in the methanol solution phase 2 O 2 Bleach until the Klett color is not more than 50; continue to massage the molar ratio of sodium hydroxide:α-methyl sulfohexadecanoate = 1:1 into the system by adding 15% mass fraction of sodium hydroxide methanol solution, Neutralize at 35°C and adjust the pH of the system to 8; the methanol is removed by rotary evaporation to obtain 37.4 g of sodium hexadecanoate sulfonate product, in which the content of the active ester sodium salt is 86.4%, and the content of disodium salt is 1.56%.

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Abstract

Disclosed is a method for making fatty acid methyl ester sulfonate with low disodium salt content by an early sulfonation and late esterification process, which belongs to the organic synthesis technique field. The method adopts Alpha-sulfo fatty acid obtained from fatty acid by sulfonation reaction firstly as a raw material, then uses methanol to implement the autocatalysis esterification for obtaining an Alpha-sulfo fatty acid methyl ester intermediate; then the target product of fatty acid methyl ester sulfonate (MES) is acquired through the bleaching by hydrogen peroxide and neutralization by sodium hydroxide in a methanol solution phase. Compared with the traditional method for preparing MES, the method need no operation of secondary esterification, so as to reduce the unit operation and shorten the flow on the one hand; on the other hand, the method need no strong acid or strong base for catalysis because the methyl esterification of Alpha-sulfo fatty acid is the catalytic reaction, so the separation step and the three wastes produced in the step are reduced; and the last one, because of the adoption of the NaOH neutralization process in the methanol solution phase, the major product of Alpha-sulfo fatty acid methyl ester sodium salt in the MES product will not be hydrolyzed into the undesirable Alpha-sulfo fatty acid disodium salt byproduct easily, so the product has good quality.

Description

Technical field [0001] A manufacturing method of fatty acid methyl ester sulfonate (MES), specifically, it is first used in industrial membrane sulfonator to use SO 3 Use air mixture as a sulfonating agent to sulfonate fatty acids into α-sulfo fatty acids, then esterify with methanol to obtain α-sulfo fatty acid methyl esters, then bleach them with hydrogen peroxide in the methanol solution phase and neutralize them with sodium hydroxide to obtain fatty acid methyl esters The method of sulfonate (MES) target product belongs to the technical field of organic synthesis. Background technique [0002] Fatty acid methyl ester sulfonate (MES) is a new type of anionic surfactant, which has attracted wide attention due to its good detergency, hard water resistance, foaming power and low irritation properties, especially when used in Phosphorus detergents replace the fixed combination of sodium alkylbenzene sulfonate and sodium tripolyphosphate, and exhibit excellent hard water resistance...

Claims

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Application Information

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IPC IPC(8): C07C309/62C07C303/32C07C309/02
Inventor 方云孙玲玲夏咏梅
Owner JIANGNAN UNIV
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