Method for combined production of 3-skatole and indole

A technology of methylindole and indole, which is applied in the field of synthesizing 3-methylindole and indole, can solve the problems of single product structure and low yield of indole, achieve reduced circulation, simple process, and reduced cost Effect

Inactive Publication Date: 2017-04-05
CHINA PETROCHEMICAL CORP +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] The technical problem to be solved by the present invention is the problem of low indole yield and single pr

Method used

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  • Method for combined production of 3-skatole and indole
  • Method for combined production of 3-skatole and indole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Aniline, ethylene glycol, and 1,2-propanediol enter the fixed-bed reactor at a ratio of 5:1:1 (molar ratio), and the catalyst is Ag / SiO 2 , the loading of Ag is 0.5%, the reaction temperature is 250°C, the reaction pressure is normal pressure, the residence time of the gas phase reaction is 0.5 seconds, the volume fraction of hydrogen added in the gas phase feed is 5%, and the volume fraction of water vapor added is 0.5%. After the reaction The gas phase material enters the condenser for condensation, collects the condensate, separates oil from water, and detects the oil phase. The conversion rate of ethylene glycol is 87%, and the yield of indole is 40% (based on hexylene glycol); the conversion rate of 1,2-propanediol is 88%. %, the yield of 3-methylindole is 10% (based on 1,2-propanediol).

Embodiment 2

[0025] Aniline, ethylene glycol, and 1,2-propanediol enter the fixed-bed reactor at a ratio of 7:1:1 (molar ratio), and the catalyst is Ag / SiO 2 , the loading of Ag is 5%, the reaction temperature is 300°C, the reaction pressure is 0.1MPa, the gas phase reaction residence time is 5 seconds, the volume fraction of hydrogen added in the gas phase feed is 5%, the volume fraction of water vapor added is 5%, after the reaction The gas phase material enters the condenser for condensation, collects the condensate, separates oil from water, and detects the oil phase. The conversion rate of ethylene glycol is 95%, and the yield of indole is 72% (based on ethylene glycol); the conversion rate of 1,2-propanediol is 95%. %, the yield of 3-methylindole is 16% (based on 1,2-propanediol).

Embodiment 3

[0027] Aniline, ethylene glycol, and 1,2-propanediol enter the fixed-bed reactor at a ratio of 10:1:1 (molar ratio), and the catalyst is Ag / SiO 2 , the loading of Ag is 8%, the reaction temperature is 350℃, the reaction pressure is 0.5MPa, the residence time of the gas phase reaction is 10 seconds, the volume fraction of hydrogen added in the gas phase feed is 3%, the volume fraction of water vapor added is 15%, after the reaction The gas phase material enters the condenser for condensation, collects the condensate, separates oil from water, and detects the oil phase. The conversion rate of ethylene glycol is 98%, and the yield of indole is 80% (calculated as ethylene glycol); the conversion rate of 1,2-propanediol is 98%. %, the yield of 3-methylindole is 40% (based on 1,2-propanediol).

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Abstract

The invention relates to a method for preparing indole by taking aniline and glycol, 1,2-propylene glycol as raw materials and simultaneously performing combined production of 3-skatole and indole, which solves the problems of low production yield of indole and single product in the prior art. According to the invention, an Ag-based heterogeneous catalyst is subjected to a flow-type gas-solid phase catalytic reaction in a fixed bed reactor, aniline and glycol, 1,2-propylene glycol are mixed in proportion and continuously fed in the fixed bed reactor, under hydrogen atmosphere, a polyphase catalytic reaction is carried out on a solid catalyst bed layer, one-step synthesis of indole is carried out, and combined production of 3-skatole is simultaneously carried out, indole yield can reach 84% (metering by glycol), and 3-skatole yield can reach 43% (metering by 1,2-propylene glycol). The catalytic process has the advantages of high activity, selectivity and stabilization performance, and has the characteristics of production of several products with one step, simple process, continuous operation, low cost and environmental protection.

Description

technical field [0001] The invention relates to a method for co-producing 3-methylindole and indole, specifically a method for one-step catalytic synthesis of 3-methylindole and indole by aniline, 1,2-propanediol and ethylene glycol. Background technique [0002] Indole is an important raw material for the preparation of medicines, pesticides, spices, dyes and feed additives, and an important heterocyclic fine chemical intermediate. In the 1980s, Watanabe and others in Japan invented the method of gas-phase synthesis of indole products from aniline and ethylene glycol under the action of a metal catalyst. The reaction process is shown in formula 1. [0003] [0004] Aniline is used as a raw material to catalyze the one-step synthesis of indole. This method not only has low raw material price and low production cost, but also has simple operation process and environmental friendliness. It has obvious advantages and is the most promising method for synthesizing indole. Ma...

Claims

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Application Information

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IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 何志勇孔伟伟李秀清
Owner CHINA PETROCHEMICAL CORP
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