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Isopalmitoyl amino acid compound as well as preparation method and application thereof

A palmitoyl amino acid and amino acid technology, which is applied in the preparation of organic compounds, the preparation of carboxylic acid amides, chemical instruments and methods, etc., can solve the problems of poor compatibility, high irritation, and refractory degradation, and achieve high water solubility and irritation. The effect of low sex and strong water solubility

Pending Publication Date: 2022-05-27
FOSHAN ENANTIOSIC CORP LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Traditional surfactants, such as sodium laureth sulfate (AES), have problems such as high irritation, high toxicity, refractory degradation and poor compatibility

Method used

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  • Isopalmitoyl amino acid compound as well as preparation method and application thereof
  • Isopalmitoyl amino acid compound as well as preparation method and application thereof
  • Isopalmitoyl amino acid compound as well as preparation method and application thereof

Examples

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preparation example Construction

[0122] In a second aspect of the present invention, there is provided a preparation method of an isopalmitoyl amino acid compound, comprising the following steps:

[0123] S100: Using isopalmitic acid as a raw material, adding a chlorinating reagent to carry out an acid chlorination reaction to prepare isopalmitoyl chloride.

[0124] S200: Mix the amino acid compound, acid binding agent and solvent, add the isopalmitoyl chloride to carry out amidation reaction to prepare isopalmitoyl amino acid compound; wherein, the structure of the amino acid compound is NH 2 -CH(R 2 )-COOH, where R 2 As defined in the first aspect of the present invention.

[0125] S100: Preparation of isopalmitoyl chloride

[0126] Isopalmitoyl chloride can be prepared by the following preparation steps: adding isopalmitic acid and n-heptane to mix, and adding a chlorination reagent dropwise to the reaction flask under stirring conditions; Chromatography TLC could not be detected); the reaction solutio...

Embodiment 1

[0153] 1.1 Preparation of isopalmitoyl chloride

[0154] Add isopalmitic acid (0.39mol, 100g) and n-heptane (150mL) to a 500mL reaction flask and mix, under stirring, cool down to 0°C to 10°C, dropwise add oxalyl chloride (64.4g, 0.507°C) to the reaction flask mol), during the dropping process, maintain the reaction temperature at 0 ℃~10 ℃; after about 3-4 hours of dripping, be warming up to 20 ℃~30 ℃, continue to react for 1-2 hours isopalmitic acid conversion is completed; Concentrate under reduced pressure below 55°C until no solvent is evaporated to obtain isopalmitoyl chloride (0.383mol, 105.2g) as a pale yellow liquid with a yield of 98% and a purity of 97%.

[0155] 1.2 Preparation of isopalmitoyl aspartate

[0156] Add aspartic acid (0.109mol, 14.5g) and water (80mL) to a 250mL reaction flask and mix, add sodium hydroxide (0.109mol, 4.4g) under stirring to prepare an aqueous solution of sodium aspartate; add acetone (40mL) mixed, and dropwise added isopalmitoyl chlor...

Embodiment 2

[0160] 2.1 Preparation of isopalmitoyl chloride

[0161] Isopalmitoyl chloride was prepared by exactly the same preparation method as step 1.1 in Example 1.

[0162] 2.2 Preparation of isopalmitoyl sarcosine

[0163] To a 250mL reaction flask, add sarcosine (0.102mol, 9.1g) and water (80mL) to mix, add sodium hydroxide (0.102mol, 4.1g) under stirring to prepare sodium sarcosinate aqueous solution; add acetone (40mL) ) and mix, add isopalmitoyl chloride (0.073mol, 20g) and 32% aqueous sodium hydroxide solution (0.146mol, 18.3g) dropwise to the reaction flask. During the dropwise addition, maintain the pH of the reaction solution at 10 to 11 and the reaction temperature at 10 ℃~20℃, the dropwise addition is completed in about 2-3 hours; after the dropwise addition is completed, the reaction is continued for 1-2 hours until the raw material isopalmitoyl chloride is converted; hydrochloric acid is added to adjust the pH to 3~4, the acetone is concentrated and recovered, and left ...

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Abstract

The invention relates to an isopalmitoyl amino acid compound, the structural general formula of which is as shown in formula (I): wherein Z1 is C8 alkyl, Z2 is C6 alkyl, R1 is H or alkyl, R2 is H, C1-4 alkyl, benzyl and-L1-X; wherein L1 is C1-4 alkylene or-CH2-Ph <->, and X is selected from any one of-OH,-SH,-SCH3,-COOH,-NH2,-NHCH3,-CONH2,-NHC (= NH) NH2, imidazolyl and indolyl. The isopalmitoyl amino acid compound disclosed by the invention is high in water solubility, simple to prepare, environment-friendly and suitable for industrial production. The invention further relates to an amino acid surfactant which is high in water solubility and small in irritation. The invention also relates to an application of the isopalmitoyl amino acid compound in the field of daily chemicals or medicines.

Description

technical field [0001] The invention belongs to the technical field of surfactants, and relates to an amino acid surfactant, in particular to an isopalmitoyl amino acid compound and a preparation method and application thereof. Background technique [0002] Surfactants are widely used in daily chemical products and play an important role in emulsifying, dispersing, solubilizing and other functions. Traditional surfactants, such as laureth sulfate sodium salt (AES), have problems such as high irritation, high toxicity, refractory degradation and poor compatibility. Amino acid surfactants are green surfactants based on amino acids. Compared with traditional surfactants, amino acid surfactants have the advantages of a wide range of biomass raw materials, less toxic and side effects, mild performance, antibacterial, and biodegradable. Using amino acids such as sarcosine, aspartic acid and sodium methyl taurine as raw materials, amino acid surfactants synthesized with fatty aci...

Claims

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Application Information

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IPC IPC(8): C07C233/47C07C231/02C09K23/28C09K23/22C11D1/10A61K8/44A61K47/18
CPCC07C233/47C07C231/02C11D1/10A61K8/44A61K47/183
Inventor 徐亮卢彪蔡祥陈昌龙王益珠林枝茂
Owner FOSHAN ENANTIOSIC CORP LTD
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