CN115872886A

CN115872886A - Preparation method of fatty acyl amino acid salt

Info

Publication number: CN115872886A
Application number: CN202211562703.4A
Authority: CN
Inventors: 陈香兰; 余志兵; 苏桂珍
Original assignee: Nanjing Huashi New Material Co ltd
Current assignee: Nanjing Huashi New Material Co ltd
Priority date: 2022-12-07
Filing date: 2022-12-07
Publication date: 2023-03-31

Abstract

The invention discloses a preparation method of fatty acyl amino acid salt, which can not only abandon organic solvent, completely use water as solvent for reaction, but also can make up for the defects of more side reactions and low yield inherent in the process. The process has the advantages of simple reaction equipment, mild reaction conditions, short production period and the like.

Description

Preparation method of fatty acyl amino acid salt

Technical Field

The invention belongs to the field of surfactants, and particularly relates to a preparation method of fatty acyl amino acid salt.

Background

The fatty acyl amino acid salt is an amino acid surfactant, is synthesized by taking natural fatty acid and amino acid as raw materials, has the characteristics of low toxicity, low irritation, good biodegradability, excellent surface activity, better compatibility, antibacterial property, corrosion resistance and the like, and is widely applied to various fields of daily chemicals, food, metal processing, corrosion protection, mineral flotation, pesticide blending, biological medicine and the like. Amino acids related to amino acid surfactants commonly used in the market at present include various neutral amino acids such as sarcosine, glycine, alanine and glutamic acid, acidic amino acids and basic amino acids, and methyl taurine. The attached fatty acid group R1 is a C6-C22 straight-chain fatty acid such as lauric acid, palmitic acid, stearic acid, etc.

The traditional process for synthesizing fatty acyl amino acid salt generally adopts a Shoton-Bowman condensation method, and the process route takes fatty acid, chlorinating agent, amino acid and the like as raw materials and tetrahydrofuran, acetone and the like as reaction solvents. In order to ensure the reaction conversion rate, the traditional process adopts a solvent method for reaction, uses a large amount of solvent, greatly improves the danger in the production process, consumes a large amount of energy in the process of removing the solvent, is difficult to remove the solvent completely, is easy to have solvent residue in products, and is not green and safe enough as a cosmetic raw material.

With the increasing supervision, the problems of safety and environmental protection are more and more emphasized by people, and the process route using water as a medium is also used successively, but the wide use of the process is seriously hindered by inevitable side reactions in the process.

Disclosure of Invention

The invention aims to: the invention aims to solve the problem that side reaction has influence on product quality under the condition that water is used as a reaction medium, and provides a green and safe process for preparing fatty acyl amino acid salt, which has high conversion rate and less impurities.

The technical scheme is as follows: the preparation method of the fatty acyl amino acid salt takes water as a reaction medium, and fatty acyl chloride and amino acid react under alkaline conditions in the presence of maltooligosaccharide glucoside to prepare the fatty acyl amino acid salt.

Preferably, the fatty acid chloride is obtained by chlorinating fatty acid with a chlorinating agent. Or may be commercially available.

Preferably, the chlorinating agent is phosphorus trichloride, thionyl chloride, phosgene or solid phosgene.

Preferably, the amino acid is glutamic acid, alanine, glycine, valine, serine or sarcosine.

Preferably, the molar ratio of the fatty acyl chloride to the amino acid is 0.8 to 1.2:1.

preferably, the alkaline condition means a pH value of 9 to 12.

Preferably, the reaction temperature is 15 to 40 ℃.

Preferably, the maltooligosaccharide glucoside accounts for 0.1-2% of the total reaction raw materials by mass.

Has the advantages that:

the preparation method of the fatty acyl amino acid salt disclosed by the invention can not only abandon organic solvents, completely take water as a solvent for reaction, but also can make up for the defects of more side reactions and low yield inherent in the process, and through the addition of the maltooligosaccharide glucoside, the Maillard reaction is controlled, the occurrence of the side reactions is inhibited, the chromaticity is reduced, the generation of brown substances is inhibited, the yield is improved, and a high-quality, green and safe amino acid surfactant product is obtained. The process has the advantages of simple reaction equipment, mild reaction conditions, short production period and the like.

Detailed Description

For the purpose of enhancing the understanding of the present invention, the present invention will be further described in detail with reference to the following examples and the accompanying drawings, which are only used for explaining the present invention and are not to be construed as limiting the scope of the present invention.

The sources and contents of the raw materials used in the examples are as follows, wherein the materials homemade from Nanjing Huashi are all prepared according to the prior art, and the preparation process thereof is not described in detail.

Nemontage Fufeng Biotech limited company with sodium glutamate content not less than 99%

Hebei Donghua Jihe chemical Limited company with glycine content not less than 98.5%

Sodium sarcosinate content: 33-35% inner Mongolia honest Yongan chemical Co Ltd

Medium salt Changzhou chemical industry Co., ltd, with liquid caustic soda content of not less than 30%

Self-made new material Limited company of Nanjing Huashi with L-alanine content not less than 99%

Self-made by Nanjing Huashi New Material Co Ltd, with maltooligosaccharide glucoside content of not less than 90%

Self-made by Nanjing Huashi New Material Co Ltd, with lauroyl chloride content of not less than 99%

Kaifeng Huarui chemical new material Co., ltd, with palmitoyl chloride content of not less than 98%

Kaifeng Huarui chemical New Material Co., ltd, with Cocoyl chloride content of not less than 98%

Example 1:

adding 270 g of water, 80 g of caustic soda liquid and 150 g of monosodium glutamate into a round-bottom flask to prepare a sodium glutamate solution, adding 15ml of maltooligosaccharide glucoside, stirring in an ice bath, cooling to 15 ℃, slowly adding 270ml of lauroyl chloride, adding for 2-3 hours, maintaining the temperature of the system at 15-25 ℃ in the ice bath in the charging reaction process, maintaining the pH of the system to be strong alkaline by using 30% sodium hydroxide solution in the process, maintaining the temperature after the charging is finished, and continuing to react until the pH is constant and the reaction is finished, thus obtaining the colorless sodium lauroyl glutamate aqueous solution. And (5) directly filtering and packaging. The conversion rate was 86% by detecting the residual amount of glutamic acid by ninhydrin color development.

Example 2:

adding 300 g of water, 100 g of caustic soda liquid and 100 g of glycine into a round-bottom flask to prepare a sodium glycinate solution, adding 5ml of maltooligosaccharide glucoside, stirring in an ice bath, cooling to 25 ℃, slowly adding 300ml of lauroyl chloride, adding for 2-3 hours, maintaining the temperature of the system in the ice bath in the charging reaction process at 20-30 ℃, maintaining the pH of the system to be strong alkaline by using 30% sodium hydroxide solution in the process, maintaining the temperature after the charging is finished, continuously reacting until the pH is constant and the reaction is finished, thus obtaining the nearly colorless sodium lauroyl glycinate aqueous solution, and directly filtering and packaging. The conversion rate is 90% by detecting the glycine residue through ninhydrin color development.

Example 3:

adding 520 g of water, 80 g of caustic soda liquid and 150 g of glutamic acid into a round-bottom flask to prepare a sodium glutamate solution, adding 15ml of maltooligosaccharide glucoside, stirring in an ice bath, cooling to 25 ℃, slowly adding 370ml of palmitoyl chloride, adding for 3-4 hours, maintaining the temperature of the system in the ice bath in the charging reaction process to be 25-40 ℃, maintaining the pH of the system to be strong alkaline by using 30% sodium hydroxide solution in the process, maintaining the temperature after the charging is finished, continuously reacting until the pH is constant and the reaction is finished, thus obtaining the light yellow sodium palmitoyl glutamate aqueous solution, and directly filtering and packaging. The conversion rate is 80% by detecting the residual quantity of glutamic acid by a ninhydrin color development method.

Example 4:

adding 300 g of water, 100 g of liquid caustic soda and 100 g of alanine into a round-bottom flask to prepare a sodium alaninate solution, adding 10ml of maltooligosaccharide glucoside, stirring in an ice bath, cooling to 25 ℃, slowly adding 300ml of cocoyl chloride, adding for 2-3 hours, maintaining the temperature of the system at 20-30 ℃ in the ice bath in the charging reaction process, maintaining the pH of the system to be strong alkaline by using 30% sodium hydroxide solution in the process, maintaining the temperature after the charging is finished, continuously reacting until the pH is constant and the reaction is finished, thus obtaining the nearly colorless sodium cocoyl alaninate solution, and directly filtering and packaging. The conversion rate was calculated to be 92% by detecting the alanine residue by ninhydrin color development.

Example 5:

adding 300 g of water and 200 g of sodium sarcosinate into a round-bottom flask, adding 5ml of maltooligosaccharide glucoside, stirring in an ice bath, cooling to 25 ℃, slowly adding 300ml of lauroyl chloride, adding for 2-3 hours, maintaining the temperature of the system at 20-30 ℃ in the ice bath in the charging reaction process, maintaining the pH of the system to be strong alkaline by using 30% sodium hydroxide solution in the process, maintaining the temperature after the charging is finished, continuously reacting until the pH is constant and the reaction is finished, and directly filtering and packaging to obtain the nearly colorless lauroyl sarcosine sodium water solution. The conversion rate was calculated to be 92% by detecting the residual amount of sarcosine by ninhydrin color development.

The above description is only for the purpose of illustrating the preferred embodiments of the present invention and should not be taken as limiting the scope of the present invention, which is intended to cover any modifications, equivalents, improvements, etc. within the spirit and scope of the present invention.

Claims

1. A method for preparing fatty acyl amino acid salt is characterized in that fatty acyl amino acid salt is prepared by taking water as a reaction medium and reacting fatty acyl chloride with amino acid under alkaline conditions in the presence of malto-oligosaccharide glucoside.

2. The method according to claim 1, wherein the fatty acid chloride is obtained by chlorinating a fatty acid with a chlorinating agent.

3. The method according to claim 2, wherein the chlorinating agent is phosphorus trichloride, thionyl chloride, phosgene or phosgene in solid form.

4. The method according to claim 1, wherein the amino acid is glutamic acid, alanine, glycine, valine, serine or sarcosine.

5. The preparation method according to claim 1, wherein the molar ratio of the fatty acid chloride to the amino acid is 0.8 to 1.2:1.

6. the method according to claim 1, wherein the alkaline condition is a pH of 9 to 12.

7. The method of claim 1, wherein the reaction temperature is 15-40 ℃.

8. The method according to claim 1, wherein the maltooligosaccharide glucoside accounts for 0.1 to 2% by mass of the total reaction materials.