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Method for producing N,N'-dicyclohexyl carbodiimide

A technology of dicyclohexylcarbodiimide and dicyclohexylurea, applied in the field of production of N,N'-dicyclohexylcarbodiimide, which can solve the problems of high odor, unstable yield, and insufficient yield

Pending Publication Date: 2021-05-07
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of relatively safe solid phosgene in this process can effectively ensure safety and environmental protection, and fundamentally eliminate the problem of serious pollution of the three wastes, but the yield of this process is not stable enough and the yield is not high enough, which will adversely affect future industrial production
[0009] The patent of CN 103922970 A discloses a production process of dicyclohexylcarbodiimide, which is to add solid phosgene to dicyclohexyl urea, and then add catalyst and reaction auxiliary agent. After the reaction is completed at 35-40°C, pass Add ammonia gas to adjust the pH to 7.5-9, distill under reduced pressure to obtain the target product, use ammonia gas to adjust the alkali, the smell is strong, the pressure on environmental protection is high, and the gas is not easy to control, and it is difficult to industrialize production

Method used

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  • Method for producing N,N'-dicyclohexyl carbodiimide
  • Method for producing N,N'-dicyclohexyl carbodiimide
  • Method for producing N,N'-dicyclohexyl carbodiimide

Examples

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Effect test

Embodiment 1

[0027] Stir 200g of dicyclohexyl urea (DCU) and 800g of ethylene glycol monobutyl ether at room temperature to cool down to about 10°C, add 360g of trichloromethyl carbonate, 2.5g of aluminum trichloride loaded on molecular sieves, and heat up Keep warm at 35°C and reflux for 2 hours, cool down to 5°C, add N,N-dimethylethanolamine dropwise, adjust the pH to 8-9, filter the reaction solution, distill off the solvent, and distill under reduced pressure at 0.9-1.2KPa to obtain the product N, N'-dicyclohexylcarbodiimide, the yield is 92.32%, and the purity is 99.55%.

[0028] The product was determined by proton nuclear magnetic spectrum, and the obtained spectrum was as follows: figure 1 shown. Among them: the two hydrogen chemical shifts of 1,1' are 3.323-3.385; the eight hydrogen chemical shifts of 2,2' are 1.515-1.838; the eight hydrogen chemical shifts of 3,3' are 1.284-1.461; 4,4 The four hydrogen chemical shifts of ' are at 1.188-1.292; that is, the structural formula of ...

Embodiment 2

[0031] Stir 200g of dicyclohexyl urea (DCU) and 600g of tolylcyclohexanone at room temperature to cool down to about 10°C, add 220g of trichloromethyl carbonate, 1.5g of ferric chloride loaded on molecular sieves, and heat up to 40°C Insulate and reflux at ℃ for 2 hours, lower the temperature to 5℃, add tri-n-butylamine dropwise, adjust the pH to 8-9, filter the reaction solution, distill off the solvent, and distill under reduced pressure at 0.9-1.2KPa to obtain the product N,N'-dicyclohexyl Carbodiimide, the yield is 89.35%, and the purity is 99.27%.

Embodiment 3

[0033] Stir 200g of dicyclohexyl urea (DCU) and 1000g of ethyl acetoacetate at room temperature to cool down to about 10°C, add 420g of trichloromethyl carbonate, 2.1g of tin tetrachloride loaded on molecular sieves, and heat up to 50 Insulate and reflux at ℃ for 4 hours, lower the temperature to 5℃, add diethylenetriamine dropwise, adjust the pH to 8-9, filter the reaction solution, distill off the solvent, and distill under reduced pressure at 0.9-1.2KPa to obtain the product N,N'-dicyclohexyl Carbodiimide, the yield is 92.54%, and the purity is 99.28%.

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Abstract

The invention discloses a preparation method of N,N'-dicyclohexyl carbodiimide. The method comprises the following steps: taking dicyclohexyl urea (DCU) and trichloromethyl carbonate (BTC) as raw materials, dissolving dicyclohexyl urea (DCU) in a solvent, uniformly stirring, cooling, adding trichloromethyl carbonate and a catalyst loaded on a molecular sieve, carrying out heat preservation reflux, cooling, adjusting the pH value to 8-9 by using alkali, filtering the reaction liquid, evaporating out the solvent, and carrying out reduced pressure distillation to obtain the product namely N,N'-dicyclohexyl carbodiimide. According to the present invention, the problems of strong odor, strong toxicity and heavy environmental pollution of the traditional process are fundamentally eliminated, and the method has characteristics of high safety coefficient, partial catalyst recycling, high catalysis efficiency, partial raw material recycling, less three wastes, high purity and high yield, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a method for producing N,N'-dicyclohexylcarbodiimide. Background technique [0002] N,N'-dicyclohexylcarbodiimide, also known as DCC, is a colorless and transparent solid, liquid above 35°C, it has a wide range of uses, and is often used in laboratories to synthesize aldehydes, anhydrides, amino acids, ketones, esters and other compounds low temperature dehydrating agent. It is also a dehydrating agent commonly used in industrial organic synthesis and medicine. It is mainly used in the production of amikacin and glutathione in my country. [0003] In the prior art, the chemical synthesis method of N,N'-dicyclohexylcarbodiimide mainly involves the following methods: thiourea method, urea method, isocyanate method and phosgene method. [0004] There are two synthetic methods in the thiourea method. The first method is to use mercury oxide as a reaction reagent. Mercury oxide is a...

Claims

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Application Information

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IPC IPC(8): C07C267/00
CPCC07C267/00C07C2601/14Y02P20/584
Inventor 李家全王静王冠庆吕玲玉
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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