Method for preparing 1-cyclohexenylethylamine through catalytic selective hydrogenation of modified Pd/C catalyst

A technology of cyclohexeneethylamine and catalyst is applied in the field of catalytic selective hydrogenation of modified Pd/C catalyst to prepare 1-cyclohexeneethylamine, which can solve the problems of low conversion rate of raw materials and poor product selectivity, and achieve economical High efficiency, simple steps and great implementability

Active Publication Date: 2017-08-04
JIANGSU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to overcome the shortcomings of low raw material conversion rate and poor product selectivity in the preparation process of 1-c...

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Put 5g of Pd / C catalyst and 0.2mL of dimethyl disulfide in a reactor filled with 50mL of ethanol and mix evenly, control the temperature of the reactor at 50°C, fully react for 2 hours, adjust the pH to 8 with dilute ammonia water, filter , washed with absolute ethanol, and set aside.

[0022] Weigh 0.3g of the modified Pd / C catalyst and add it into the autoclave with 50mL of absolute ethanol, measure 5mL of 1-cyclohexene acetonitrile into the autoclave, set the temperature of the autoclave at 70°C, After replacing the air in the kettle, set the hydrogen pressure to 3MPa for reaction, adjust the stirring speed to 500r / min, and take samples for analysis at intervals of 30min during the reaction. After reacting for 5 hours, the conversion rate of raw materials was analyzed to be 83.4%, and the yield was 86.7%.

Embodiment 2

[0024] Put 5g of Pd / C catalyst and 0.2mL of dimethyl disulfide in a reactor filled with 50mL of ethanol and mix evenly, control the temperature of the reactor at 50°C, fully react for 2 hours, adjust the pH to 8 with dilute ammonia water, filter , washed with absolute ethanol, and set aside.

[0025] Weigh 0.2g of the modified Pd / C catalyst and add it into the autoclave with 50mL of absolute ethanol, measure 5mL of 1-cyclohexene acetonitrile into the autoclave, set the temperature of the autoclave at 80°C, After replacing the air in the kettle, set the hydrogen pressure to 5MPa for reaction, adjust the stirring speed to 600r / min, and take samples for analysis at intervals of 30min during the reaction. After reacting for 5 hours, the conversion rate of raw materials was analyzed to be 80.1%, and the yield was 88.2%.

Embodiment 3

[0027] Put 5g of Pd / C catalyst and 0.1mL of ethanethiol in a reactor filled with 50mL of ethanol and mix evenly, control the temperature of the reactor at 60°C, and fully react for 3 hours. 2 CO 3 The aqueous solution was adjusted to pH 7, filtered, washed with absolute ethanol, and set aside.

[0028] Weigh 0.2g of the modified Pd / C catalyst and add it to the autoclave with 50mL of absolute ethanol, measure 5mL of 1-cyclohexene acetonitrile into the autoclave, set the temperature of the autoclave at 60°C, After replacing the air in the kettle, set the hydrogen pressure to 5MPa for reaction, adjust the stirring speed to 600r / min, and take samples for analysis at intervals of 30min during the reaction. After reacting for 5 hours, the conversion rate of raw materials was analyzed to be 84.2%, and the yield was 87.1%.

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Abstract

The invention discloses a method for preparing 1-cyclohexenylethylamine through catalytic selective hydrogenation of a modified Pd/C catalyst. The method comprises the steps of (1) modifying a Pd/C catalyst, namely modifying the Pd/C catalyst through one or more of dimethyl disulfide, ethanethiol, dimethyl sulfide, thiophene, hydrogen sulfide and sulfur dioxide, adjusting the pH to be 7-11 by using an alkaline substance, filtering and washing to obtain a modified Pd/C catalyst; and (2) putting the modified Pd/C catalyst and 1-cyclohexenylacetonitrile into a reaction kettle of an ethanol solvent and reacting under the conditions that hydrogen pressure is 1-10MPa, the rate is 200-800r/min and the temperature is 50-140 DEG C to obtain the 1-cyclohexenylethylamine. According to the method for preparing the 1-cyclohexenylethylamine through catalytic selective hydrogenation of the modified Pd/C catalyst, the raw material conversion rate is greater than 80%, the selectivity is greater than 85% and the method can be used for industrial production.

Description

technical field [0001] The invention belongs to the technical field of inorganic catalysis, and in particular relates to a method for preparing 1-cyclohexeneethylamine by catalytic selective hydrogenation of a modified Pd / C catalyst. Background technique [0002] Cyclohexeneethylamine is an important pharmaceutical intermediate, which is widely used in the synthesis of pharmaceutical intermediates such as Kemiphen, Temaren and Morphine. Generally, 1-cyclohexene ethylamine is obtained by indirect conversion of 1-cyclohexene acetonitrile, formula, and a series of catalytic selective hydrogenation of 1-cyclohexene acetonitrile has been carried out at home and abroad to prepare 1-cyclohexene ethylamine research, and achieved certain results. [0003] Suzhou Aiti Pharmaceutical Chemical Co., Ltd. has studied the process of preparing 1-cyclohexeneethylamine using vanadium, niobium, and hafnium as catalysts (CN201610114613.7). This method has the problem of high catalyst prices. ...

Claims

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Application Information

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IPC IPC(8): C07C209/48C07C211/25B01J23/44
CPCB01J23/44C07C209/48C07C211/25
Inventor 郑纯智张国华杨凤丽翁居轼姚鹏飞石培培刘莉
Owner JIANGSU UNIV OF TECH
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