A kind of preparation method and application of n-acyl acidic amino acid or its salt

An acid amino acid, acyl acid technology, applied in the preparation of N-acyl acid amino acid or its salt, the low-cost preparation field of fatty acyl acid amino acid surfactant, can solve the problem of rising process energy consumption, difficulty in scaling up production equipment, and improving Production costs and other issues, to achieve the effect of reducing production costs, satisfying product quality, and reducing product costs

Active Publication Date: 2016-03-16
NANJING HUASHI NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the acidic amino acid uses water as a solvent in the condensation with acid chloride, its conversion rate is relatively low, usually only 70%, the product quality is low, and the post-treatment is complicated. In actual production, polar organic solvents are mostly used, which can greatly increase the conversion rate to 85-90%, but the problem is that the post-processing is complicated and the cost rises sharply, resulting in high product prices and cannot be used on a large scale like neutral amino acid surfactants
[0004] U.S. Patent US6008390 discloses that in the aqueous phase reaction system, the conversion rate of glutamic acid can be increased to about 85% under the working conditions of a high-energy agitator, but the energy consumption of this process will increase significantly, and it is very difficult to scale up large-scale industrial production equipment At the same time, high-speed stirring leads to too much foam, which reduces the reaction mixing effect, which undoubtedly brings difficulties to production and greatly increases production costs, affecting its market application.
Moreover, in the above-mentioned preparation process, glutamic acid is too much in excess, the cost is high, and the residual amino acid brings trouble to the use in the product.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation of embodiment 1 sodium cocoyl glutamate

[0025] 290g sodium glutamate aqueous solution is placed in the reaction bottle (sodium glutamate content 25%, pH value is 12, temperature 20 ℃), 110g cocoyl chloride is placed in the dropping funnel, the molar ratio of acid chloride and glutamic acid is 1: 0.9, slowly add acid chloride dropwise, and adjust the pH value of the material in the reaction bottle with 30% sodium hydroxide solution, keep the pH value at 10-11, after the acid chloride is added dropwise to 90% of the total amount, add 70g mass concentration immediately. 14.6% sodium glycinate aqueous solution, the molar ratio of sodium glycinate to acid chloride is 0.2:1, and the reaction temperature is slowly raised to 25-30°C, and kept for 1h. After the reaction, the product was clear and transparent. The free fatty acid salt content is 2.9% in the product measured by HPLC, and the calculated conversion rate is 85% by acid chloride.

Embodiment 3

[0028] The preparation of embodiment 3 sodium lauroyl glutamate

[0029]Place 290g of sodium glutamate aqueous solution in a reaction bottle (sodium glutamate content 25%, pH value 12, temperature 20°C), place 125g of lauroyl chloride in the dropping funnel, and the molar ratio of acid chloride to glutamic acid is 1:0.75 , slowly drop the acid chloride, and adjust the pH value of the material in the reaction bottle with 30% sodium hydroxide solution, keep the pH value at 10-11, and immediately add 118g of sarcosine with a mass concentration of 15.0% after the acid chloride is added dropwise to 75%. Sodium acid aqueous solution, the molar ratio of sodium sarcosinate to acid chloride is 0.35:1, and the reaction temperature is slowly raised to 25-30°C, and kept for 1h. After the reaction finished, the product was clear and transparent, and the free fatty acid salt content in the HPLC measurement product was 2.7%, and the calculated conversion rate was 86% by acid chloride.

Embodiment 4C12

[0030] The preparation of embodiment 4C12 / C14 sodium fatty acyl glutamate

[0031] Using the same conditions as in Example 1, C12 / C14 mixed fatty acid chloride was used to replace cocoyl chloride, the molar ratio of acid chloride: glutamic acid: glycine molar ratio was 1:1:0.1, and sodium hydroxide was replaced by KOH. After the reaction finished, the product was slightly turbid, and the content of free fatty acid salt in the product was determined by HPLC to be 4.1%, and the calculated conversion rate was 80% by acid chloride.

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Abstract

The invention discloses a preparation method of N-acyl acidic amino acid or its salt, which comprises the amidation reaction of fatty acid chloride and amino acid under alkaline conditions, and is characterized in that the amidation reaction uses water as a solvent and acidic Amino acid or its salt is used as the main raw material, and a small amount of neutral amino acid or its salt is used as an auxiliary raw material. Under the condition of stirring, the fatty acid chloride is firstly added dropwise to the aqueous solution of acidic amino acid or its salt, and the pH value of the reaction solution is adjusted by adding alkali; After the fatty acid chloride is added dropwise to a certain amount, add the aqueous solution of neutral amino acid or its salt, continue to drop the fatty acid chloride until the dropwise addition is completed, and stir to maintain the reaction. The method uses mixed amino acids and fatty acid chlorides to react in an aqueous phase system, which can significantly increase the conversion rate of amino acids and acid chlorides, greatly reduce the amount of residual amino acids, and the products can be directly used as surfactants after simple treatment, and the cost is greatly reduce.

Description

technical field [0001] The invention relates to a surfactant N-acyl amino acid or a salt thereof, in particular to a preparation method of an N-acyl acidic amino acid or a salt thereof, which is a low-cost preparation method of a fatty acyl acid amino acid surfactant; And the application of the N-acyl acidic amino acid prepared by the method. Background technique [0002] N-acyl amino acid or its salt is a kind of compound obtained by acylation of amino acid, usually formed by condensation of fatty acid chloride and amino acid. This type of compound has good surface activity, foaming performance, cleaning performance and mildness, and is widely used in Cosmetics, personal cleaning and care products, and also have broad applications in other fields such as food additives, metal processing, ore flotation, oil extraction, and agriculture, biological products and drug preparation. [0003] N-acyl acidic amino acid or its salt is a kind of compound obtained by amidation of acidi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C233/47C07C231/02A61K8/44A61Q19/10
CPCA61Q19/10C07C231/02A61K8/44C07C233/47
Inventor 汪昌国陈香兰李宝勇
Owner NANJING HUASHI NEW MATERIAL CO LTD
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