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Method for synthesizing N, N'-dicyclohexylcarbodiimide through hydrogen peroxide serving as oxidizing agent

A technology of dicyclohexylcarbodiimide and hydrogen peroxide, which is applied in the direction of organic chemistry, can solve the problems of high hidden dangers, highly toxic phosgene, and difficult to apply to workshop production, so as to improve utilization rate, reduce environmental protection investment, waste The effect of volume reduction

Inactive Publication Date: 2019-02-15
SHANDONG HUIHAI PHARMA & CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The process of phosgene is highly toxic and has great hidden dangers, so it is difficult to apply to workshop production

Method used

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  • Method for synthesizing N, N'-dicyclohexylcarbodiimide through hydrogen peroxide serving as oxidizing agent

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Mix N,N'-dicyclohexylthiourea and solvent toluene at a mass ratio of 1.9:1, then slowly add the catalyst triethylamine under stirring conditions, the amount of triethylamine is 5% of the total material mass, at 20°C Add hydrogen peroxide dropwise for oxidation reaction, the mass ratio of hydrogen peroxide to N,N′-dicyclohexylthiourea is 1.15:1, keep warm for 1.5h after the dropwise addition, then filter with suction at 15°C, decolorize, and distill under reduced pressure N,N'-dicyclohexylcarbodiimide was obtained with a yield of 93.9% and a purity of 99.34%. The waste water produced by oxidation passed the test after MVR distillation and was used as cooling circulating water.

Embodiment 2

[0023] Mix N,N'-dicyclohexylthiourea and solvent toluene at a mass ratio of 1.6:1, then slowly add the catalyst triethylamine under stirring conditions, the amount of triethylamine is 4% of the total material mass, at 25°C Add hydrogen peroxide dropwise for oxidation reaction, the mass ratio of hydrogen peroxide to N,N′-dicyclohexylthiourea is 1:1, keep warm for 1.5h after the dropwise addition, then filter with suction at 15°C, decolorize and distill under reduced pressure N,N'-dicyclohexylcarbodiimide was obtained with a yield of 93.6% and a purity of 99.35%. The waste water produced by oxidation passed the test after MVR distillation and was used as cooling circulating water.

Embodiment 3

[0025] Mix N,N'-dicyclohexylthiourea and solvent toluene at a mass ratio of 1.8:1, then slowly add the catalyst triethylamine under stirring conditions, the amount of triethylamine is 6% of the total material mass, at 15°C Add hydrogen peroxide dropwise for oxidation reaction, the mass ratio of hydrogen peroxide to N,N′-dicyclohexylthiourea is 1.2:1, keep warm for 1.5h after the dropwise addition, then suction filter at 15°C, decolorize, and distill under reduced pressure N,N'-dicyclohexylcarbodiimide was obtained with a yield of 93.7% and a purity of 99.37%. The waste water produced by oxidation passed the test after MVR distillation and was used as cooling circulating water.

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Abstract

The invention relates to a method for synthesizing N, N'-dicyclohexylcarbodiimide through hydrogen peroxide serving as an oxidizing agent. The method comprises the following steps: mixing N, N'-dicyclohexyl thiocarbamide and a solvent, slowly adding a catalyst, dropwise adding hydrogen peroxide at 15 to 25 DEG C to perform oxidation reaction, performing heat preservation for 1.5 h after dropwise adding is accomplished, then performing suction filtration at 15 DEG C, and performing decoloration and reduced pressure distillation, so as to obtain the N, N'-dicyclohexylcarbodiimide. The method hasthe advantages that the oxidizing agent hydrogen peroxide is adopted to ensure that reaction is more complete, the content of by-products N, N'-dicyclohexylurea and cyclohexyl isothiocyanate is controlled to be lower than 100 ppm, the product quality is improved, and the problem that effluent brine is difficult to treat is solved; a reaction system is optimized, a triethylamine catalyst is adopted to ensure that the reaction is performed in a homogeneous reaction system, the reaction yield is improved, the DCC yield is improved to greater than 93.5 percent, and the reaction is easy to control; and the material utilization is improved, the amount of waste is reduced, the investment in environmental protection is reduced, and the production cost is reduced.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a method for synthesizing N,N'-dicyclohexylcarbodiimide by using hydrogen peroxide as an oxidant. Background technique [0002] N,N'-Dicyclohexylcarbodiimide (DCC) is a good low-temperature biochemical dehydrating agent, used for the synthesis and dehydration of amikacin and amino acids, and also for the dehydration of acids, anhydrides, aldehydes, ketones, etc. Synthesis, this product is also used in the synthesis of peptides and nucleic acids. DCC dehydration condensation is used, the reaction conditions are mild, and the synthesis yield is high, so it is often used as a dehydrating agent or carboxyl activator for polypeptide synthesis, or for coupling small molecular compounds and polypeptides with carrier proteins. In recent years, the sales situation of DCC has continued to grow, and the supply of products is in short supply. At the same time,...

Claims

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Application Information

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IPC IPC(8): C07C267/00
CPCC07C267/00C07C2601/14
Inventor 张永霞郑庚修赵攀峰张国辉王克文张世凤
Owner SHANDONG HUIHAI PHARMA & CHEM
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