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A kind of synthetic method of sodium palmitoyl amino acid

A technology of sodium palmitoyl amino acid and a synthetic method, which is applied in chemical instruments and methods, preparation of carboxylic acid amides, preparation of organic compounds, etc., to achieve high reaction yield, reasonable process conditions, and easy industrial production

Active Publication Date: 2016-08-17
CHANGSHA PUJI BIOTECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no report on the production of palmitoyl chloride by the phosgene method, and the preparation of sodium palmitoyl amino acid from the resulting acid chloride

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] In a 500mL four-neck flask equipped with a thermometer, a reflux condenser, an air guide tube, and agitation, add 256g (1mol) of palmitic acid and 1.5g (0.02mol) of N,N-dimethylformamide, and raise the temperature to 60°C. The reaction temperature is 70-80°C. Within 5-10 hours, 110g (1.1mol) of phosgene is introduced. After the reaction is completed, vacuum distillation is performed to collect fractions at 160-180°C (1333Pa) to obtain 245g of palmitoyl chloride, with a yield of 89%.

[0023] In a 1000mL four-necked flask equipped with a thermometer, a dropping funnel, and stirring, add 191g (1mol) of glutamic acid, dissolve it in 570g of water, stir at room temperature to dissolve it completely, and make a 25% aqueous solution, and add 302g of palmitoyl chloride (1.1mol) into a dry dropping funnel, control the temperature in an ice-water bath at 15-20°C, add palmitoyl chloride under stirring, and at the same time add 25% aqueous sodium hydroxide solution dropwise to keep...

Embodiment 2

[0026] Synthesis of palmitoyl chloride is the same as in Example 1.

[0027] In a 1000mL four-neck flask equipped with a thermometer, a dropping funnel, and stirring, add 111g (1mol) of alanine, dissolve it in 333g of water, stir at room temperature to dissolve it completely, and then make a 25% aqueous solution. 302g of palmitoyl chloride (1.1mol) into a dry dropping funnel, control the temperature in an ice-water bath at 15-20°C, add palmitoyl chloride under stirring, and at the same time add 25% aqueous sodium hydroxide solution dropwise to keep the reaction solution at pH= 8 to 10, until the addition is complete; continue to react for 4 to 5 h. After the reaction, the pH value was adjusted to 1-2 with 6N hydrochloric acid, and a large amount of white crystals were precipitated. After the product was completely precipitated, it was filtered and dried to obtain 314 g of palmitoylalanine, with a yield of 96%.

[0028] Dissolve 327g (1mol) of palmitoyl alanine in 610g of etha...

Embodiment 3

[0030] Synthesis of palmitoyl chloride is the same as in Example 1.

[0031] In a 1000mL four-necked flask equipped with a thermometer, a dropping funnel, and stirring, add 97g (1mol) of glycine, dissolve it in 291g of water, stir at room temperature to dissolve it completely, and make a 25% aqueous solution. Add 302g (1.1 mol) into a dry dropping funnel, control the temperature in an ice-water bath at 15-20°C, add palmitoyl chloride under stirring, and at the same time add 25% aqueous sodium hydroxide solution dropwise to keep the reaction solution at pH = 8- 10, until the addition is complete; continue to react for 4 to 5 h. After the reaction, the pH value was adjusted to 1-2 with 6N hydrochloric acid, and a large amount of white crystals were precipitated. After the product was completely precipitated, it was filtered and dried to obtain 294 g of palmitoylglycine, with a yield of 94%.

[0032] Dissolve 313g (1mol) of palmitoylglycine in 480g of ethanol, add 200g of ethano...

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PUM

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Abstract

The invention relates to a synthesis method of palmitoyl amino acid sodium in the surfactant field, in particular relates to a method for preparing palmitoyl amino acid sodium by using palmitoyl chloride synthesized by a phosgene method. The synthesis method comprises the following steps: by taking palmitic acid and phosgene as raw materials, preparing palmitoyl chloride through reaction in the presence of an organic amide catalyst; dropwise adding palmitoyl chloride in an amino acid alkaline solution to obtain palmitoyl amino acid through reaction; and dissolving obtained palmitoyl amino acid with ethanol and adding the ethanol solution of sodium hydroxide to finally obtain palmitoyl amino acid sodium. In the synthesis method, a lot of phosphorus-containing wastewater is not produced even though phosphorus trichloride is used as a chlorination agent; sulfur dioxide generated by a thionyl chloride method can heavily pollute the environment; and the synthesis method reasonable in process, high in reaction yield and good in product quality, and the product does not contain residual phosphorus and sulfur and can be widely used in high-end anti-aging cosmetics.

Description

technical field [0001] The invention relates to a synthesis method of palmitoyl amino acid sodium in the field of surfactants, in particular to a synthesis method for preparing palmitoyl amino acid sodium from palmitoyl chloride synthesized by a phosgene method. Background technique [0002] With the rapid development of the global economy and the improvement of living standards, people have higher and higher requirements for cosmetics. Therefore, anti-aging and anti-wrinkle cosmetics are more and more valued by people, and the anti-aging cosmetics industry has developed rapidly. There are many kinds of natural or synthetic anti-aging cosmeceuticals used in medicines with anti-aging effects on the skin. Cosmeceuticals using advanced medical technology have developed rapidly, and the global market for cosmeceuticals is as high as more than 50 billion US dollars. Skin aging is a continuous and gradual physiological process, mainly including genetic theory, error theory, free r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C231/12C07C231/02C07C233/47C07D207/16
Inventor 李耀莲
Owner CHANGSHA PUJI BIOTECH
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