Preparation method and application of N-acyl acidic amino acid or salt thereof

An acidic amino acid and acyl acidic technology, which is applied in the preparation of N-acyl acidic amino acids or their salts, and the low-cost preparation of fatty acyl acidic amino acid surfactants. Production cost and other issues, to achieve the effect of production cost reduction, product quality satisfaction and product cost reduction

Active Publication Date: 2013-12-11
NANJING HUASHI NEW MATERIAL
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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

[0025] Embodiment 1 Preparation of Sodium Cocoyl Glutamate

[0026] 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, add acid chloride slowly, 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 of 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.

[0027]

Embodiment 3

[0031] Example 3 Preparation of Sodium Lauroyl Glutamate

[0032]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.

[0033]

Embodiment 4

[0034] The preparation of embodiment 4 C12 / C14 sodium fatty acyl glutamate

[0035] 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.

[0036]

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PUM

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Abstract

The invention discloses a preparation method of N-acyl acidic amino acid or a salt thereof. According to the preparation method, fatty acyl chloride and an amino acid are subjected to an amidation reaction under an alkaline condition. The preparation method is characterized in that in the amidation reaction, water is used as a solvent, an acidic amino acid or a salt thereof is used as a main raw material and a small amount of a neutral amino acid or a salt thereof is used as an auxiliary raw material. The preparation method comprises the following steps: under a stirring condition, dropping the fatty acyl chloride into the aqueous solution of the acidic amino acid or the salt thereof; adding an alkali to adjust the pH value of the reaction solution; after a certain amount of fatty acyl chloride is dropped, adding the aqueous solution of the neutral amino acid or the salt thereof, continue to drop the fatty acyl chloride until the dropping is finished and stirring to maintain the reaction. According to the preparation method, the mixed amino acid and the fatty acyl chloride react under a water-phase system, so that the conversion rates of the mixed amino acid and the fatty acyl chloride can be remarkably increased and the amount of residual amino acids is greatly reduced. The product can be directly used as a surfactant after being treated simply, and thus the cost is greatly reduced.

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 Applications(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
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