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A kind of method that o-ethylaniline dehydrocyclization prepares indole

A technology of o-ethylaniline and dehydrocyclization, which is applied in the field of indole production, can solve the problems of high reaction temperature, easy loss, and high production cost, and achieve the effects of low reaction temperature, easy operation, and high selectivity

Active Publication Date: 2018-11-13
CHINA PETROLEUM & CHEM CORP +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The ethylene glycol-aniline method requires a large amount of aniline as a diluent, and the recovery of aniline requires high energy consumption, low product purity, multiple purifications, and high production costs.
[0004] The o-nitroethylbenzene method first obtains o-ethylaniline by reducing o-nitroethylbenzene, and then adds o-ethylaniline to a fixed-bed reactor for dehydrocyclization to prepare indole. Most of the dehydrocyclization of o-ethylaniline uses Al 2 o 3 , SiO 2 -Al 2 o 3 , but the reaction temperature is high, generally above 600°C, and the indole yield is low (below 30%). In the later stage, CuO-Al is prepared by improving the catalyst and adding copper and boron 2 o 3 -B 2 o 3 The three-way catalyst is used for the dehydrocyclization of o-ethylaniline, which greatly improves the yield and conversion rate, but there are still high reaction temperatures (about 700 ° C), and B in the catalyst 2 o 3 Due to the high temperature, it is easy to lose during the reaction, and the performance of the catalyst will gradually decrease, and the lost B 2 o 3 It will condense on the inner wall of the reactor outlet, causing the reactor to be blocked, and there are also disadvantages such as high energy consumption and large equipment investment

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] In a 0.5L autoclave equipped with a gas-liquid separator, add 300 milliliters of o-ethylaniline, catalyst RU-Al 2 o 3 8.64 grams, wherein the content of Ru is 3%, 0.86 grams of boric acid, replaced by nitrogen, heated up to 280 ° C, when the pressure in the kettle is 0.5Mpa, slowly release the pressure, and keep the reaction temperature when the pressure in the kettle reaches 0.3Mpa Continue to release the pressure slowly, so many times until the pressure in the kettle is lower than 0.1Mpa, after the reaction is completed, the material is cooled and cooled, and the ice-water cooling product indole is separated out from the solution. The conversion rate of o-ethylaniline is above 72%, the yield of indole is above 45%, and the selectivity of indole is above 65%.

Embodiment 2

[0021] In a 0.5L autoclave equipped with a gas-liquid separator, add 300 milliliters of o-ethylaniline, catalyst RU-Al 2 o 3 17.3 grams, wherein the content of Ru is 3%, 1.73 grams of boric acid, replaced by nitrogen, heated to 300 ° C, when the pressure in the kettle is 0.5Mpa, slowly release the pressure, and keep the reaction temperature when the pressure in the kettle reaches 0.3Mpa Continue to release the pressure slowly, so many times until the pressure in the kettle is lower than 0.1Mpa, after the reaction is completed, the material is cooled and cooled, and the ice-water cooling product indole is separated out from the solution. The conversion rate of o-ethylaniline is above 75%, the yield of indole is above 50%, and the selectivity of indole is above 70%.

Embodiment 3

[0023] In a 0.5L autoclave equipped with a gas-liquid separator, add 300 milliliters of o-ethylaniline, catalyst RU-Al 2 o 3 14.4 grams, wherein the content of Ru is 8%, boric acid 1.44 grams, nitrogen displacement, heating up to 380 ° C, when the pressure in the kettle is 0.5Mpa, slowly release the pressure, and keep the reaction temperature after the pressure relief. When the pressure in the kettle reaches 0.3Mpa Continue to release the pressure slowly, so many times until the pressure in the kettle is lower than 0.1Mpa, after the reaction is completed, the material is cooled and cooled, and the ice-water cooling product indole is separated out from the solution. The conversion rate of o-ethylaniline is above 90%, the yield of indole is above 80%, and the selectivity of indole is above 92%.

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Abstract

The invention relates to a method for preparing indole through dehydrocyclizing o-ethylaniline. The method is characterized in that an RU-Al2O3 used as a catalyst boric acid adopted as a cocatalyst are added to a slurry bed reactor, nitrogen is introduced before a reaction to displace air, and o-ethylaniline is dehydrocyclized under a oxygen-free condition in order to synthesize indole. The method has the characteristics of low reaction temperature, easiness in operation and high indole selectivity.

Description

technical field [0001] The invention relates to an indole production technology, which belongs to the field of fine chemical industry. Background technique [0002] Indole is an intermediate for the production of tryptophan, and it is also a raw material for a series of pharmaceuticals, spices, dyes and other organic intermediates. There are not many preparation methods for indole at home and abroad, and the methods for large-scale production of indole mainly include ethylene glycol Alcohol-aniline method and o-nitroethylbenzene method. [0003] The ethylene glycol-aniline method requires a large amount of aniline as a diluent, which has the disadvantages of high energy consumption for aniline recovery, low product purity, multiple purifications, and high production costs. [0004] The o-nitroethylbenzene method first obtains o-ethylaniline by reducing o-nitroethylbenzene, and then adds o-ethylaniline to a fixed-bed reactor for dehydrocyclization to prepare indole. Most of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 赵思远
Owner CHINA PETROLEUM & CHEM CORP