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Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide

A dicyclohexylcarbodiimide, microwave-assisted technology, applied in the direction of organic chemistry, can solve the problem of difficult two-phase reaction, and achieve the effects of improving the reaction conversion rate, reducing by-products, and shortening the reaction time

Pending Publication Date: 2021-04-16
SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to provide a method for synthesizing N,N'-dicyclohexylcarbodiimide by a microwave-assisted method. The catalyst loaded on the molecular sieve has a large specific surface area and high catalytic efficiency; the microwave-assisted method is adopted, and phase transfer is added Catalyst, which overcomes the problems of difficult and incomplete two-phase reaction in the traditional process, greatly improves the reaction conversion rate, and the product has the characteristics of high purity and yield

Method used

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  • Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide
  • Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide
  • Microwave-assisted method for synthesizing N,N'-dicyclohexyl carbodiimide

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Using a microwave reactor, under the microwave radiation power of 100W, add 100g N,N'-dicyclohexyl urea (DCU) to 400g ethylene glycol monobutyl ether at room temperature, cool down to 10-12°C, and add trichloroacetyl chloride 180g, 1.5g of anhydrous aluminum trichloride loaded on molecular sieves, heated up to 30°C for 2 hours, then cooled to 5°C; added 1.0g of phase transfer catalyst dodecyltrimethylammonium chloride, and then added dropwise N , N-dimethylethanolamine adjusts the pH value to 8-9, alkali hydrolysis reaction occurs, the temperature of the alkali hydrolysis reaction is controlled at 5°C, the alkali hydrolysis reaction time is 20min, and the stirring speed of the alkali hydrolysis reaction is 100 rev / min; Filtrate, separate liquid, distill off the solvent, distill under reduced pressure at 0.7-0.9KPa, collect fractions at 135-145°C to obtain 83.01g of N,N'-dicyclohexylcarbodiimide with a yield of 90.15% and a purity of 99.88 %.

[0034] The NMR spectrum o...

Embodiment 2

[0037] Using a microwave reactor, under the microwave radiation power of 150W, add 100g of N,N'-dicyclohexylurea (DCU) to 400g of toluenecyclohexanone at room temperature, cool down to 10-12°C, add 180g of thionyl chloride, 1.8g of anhydrous ferric trichloride loaded on molecular sieves was heated to 40°C for 2 hours and then cooled to 5°C; 0.84g of phase transfer catalyst trioctylmethyl ammonium chloride was added, and then tri-n-butylamine was added dropwise to adjust When the pH value reaches 9-10, alkaline hydrolysis reaction occurs, control the alkaline hydrolysis reaction temperature to 10°C, the alkaline hydrolysis reaction time is 30min, and the stirring speed of the alkaline hydrolysis reaction is 200 rpm; the reaction solution is filtered, separated, and the solvent is evaporated , Distilled under reduced pressure at 0.9-1.1KPa, collected fractions at 135-145°C to obtain 83.04g of N,N'-dicyclohexylcarbodiimide, with a yield of 90.08% and a purity of 99.77%.

Embodiment 3

[0039]Using a microwave reactor, under the microwave radiation power of 180W, add 100g of N,N'-dicyclohexylurea (DCU) to 400g of ethyl acetoacetate at room temperature, cool down to 10-12°C, add 180g of benzoyl chloride, load Anhydrous tin tetrachloride 2.1g on the molecular sieve, heat up to 50°C and keep it under reflux for 2h, cool down to 5°C; add 0.9g of phase transfer catalyst tetradecyltrimethylammonium chloride, and then drop triethylamine to adjust When the pH value reaches 9-10, alkaline hydrolysis reaction occurs, control the alkaline hydrolysis reaction temperature to 20°C, the alkaline hydrolysis reaction time is 40min, and the stirring speed of the alkaline hydrolysis reaction is 300 rpm; the reaction solution is filtered, separated, and the solvent is evaporated , Distilled under reduced pressure at 0.9-1.0KPa, collected fractions at 135-145°C to obtain 83.22g of N,N'-dicyclohexylcarbodiimide, with a yield of 90.31% and a purity of 99.81%.

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing N,N'-dicyclohexyl carbodiimide through a microwave-assisted method. The method comprises the following steps: dissolving N,N'-dicyclohexyl urea in a solvent under microwave radiation, adding an oxidant and a catalyst loaded on a molecular sieve, and carrying out heat preservation reflux; adding a phase transfer catalyst, adjusting the pH value, and carrying out alkaline hydrolysis reaction; filtering, separating liquid, evaporating out the solvent, and carrying out reduced pressure distillation to obtain N,N'-dicyclohexyl carbodiimide. The catalyst loaded on the molecular sieve is large in specific surface area and high in catalytic efficiency; a microwave-assisted method is adopted, and a phase transfer catalyst is added, so that the problems of difficult two-phase reaction and incomplete reaction in the traditional process are solved, the reaction conversion rate is greatly improved, the reaction time is shortened, and the product has the characteristics of high purity and yield.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a microwave-assisted method for synthesizing N,N'-dicyclohexylcarbodiimide. Background technique [0002] N,N'-dicyclohexylcarbodiimide, also known as DCC, is a colorless transparent solid at room temperature, and it is liquid above 35°C. It is often used in laboratories to synthesize aldehydes, anhydrides, ketones, amino acids, esters and other compounds at low temperatures. Dehydrating agent. At the same time, it is also one of the most important reagents for the acylation reaction of amines (or alcohols) and carboxylic acids in industry. It also plays a unique role in the synthesis of important and rare macrocyclic lactams and macrocyclic lactones. In my country, it is mainly used in the production of glutathione and amikacin and other products. [0003] In the prior art, the chemical synthesis methods of N,N'-dicyclohexylcarbodiimide mainly involve the following me...

Claims

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Application Information

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IPC IPC(8): C07C267/00
Inventor 王辉王静孙铎
Owner SHANDONG JINCHENG KERUI CHEMICAL CO LTD
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