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Method for synthesizing 3-(tert-butyl)phenol

A technology of tert-butylphenol and a synthetic method is applied in directions such as the preparation of nitro compounds, the preparation of amino compounds, chemical instruments and methods, and can solve problems such as unfavorable large-scale production, high reaction temperature, and difficulty in obtaining raw materials, and achieve product yield. The effect of high rate, high reaction selectivity and cheap raw materials

Active Publication Date: 2015-12-30
RUDONG ZHONGYI CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Patent US2760991 reports that tert-butylbenzene is used as raw material, catalyzed by divalent copper ions, and the product can be obtained by reaction at high temperature. The reaction temperature is high, the requirements for equipment are high, and there are many by-products, which is not conducive to large-scale production
M.S.Carpenter, et al. ( J. Org. Chem , 1951,16:586-617) introduced m-tert-butylaniline as a raw material, and obtained the product through diazotization hydrolysis reaction. This method has high yield and is easy to operate, but the raw material is not easy to obtain and expensive

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] (1) Put 800Kg of p-tert-butylchlorobenzene into the reaction kettle A, and under the condition that the temperature of the reaction kettle A is controlled at 0°C, add the mixed acid of concentrated sulfuric acid and nitric acid at a temperature of 0°C dropwise, wherein the concentrated sulfuric acid is 830L, and the nitric acid After dripping, raise the temperature of reactor A to 20°C~25°C, stir reactor A, and react overnight. After the reaction is completed, pour the reaction solution into water to obtain an organic phase layer and an inorganic phase layer, and add 3000L acetic acid Ethyl was extracted three times, combined to obtain the organic phase layer solution, the organic phase layer solution was dried, ethyl acetate was recovered, and vacuum distillation was used to collect the 180°C / 30mmHg column fraction, which was 1-chloro-4-tert-butyl-2- Nitrobenzene;

[0023] (2) Take 1 ton of 1-chloro-4-tert-butyl-2-nitrobenzene, put 100Kg of palladium carbon and 3500L o...

Embodiment 2

[0026] (1) Put 600Kg of p-tert-butylchlorobenzene into reactor A, and under the condition that the temperature of reactor A is controlled at 0°C, add dropwise the mixed acid of concentrated sulfuric acid and nitric acid at 0°C, of ​​which the concentrated sulfuric acid is 640L, and the nitric acid After dripping, raise the temperature of reactor A to 20°C~25°C, stir reactor A, and react overnight. After the reaction is completed, pour the reaction solution into water to obtain an organic phase layer and an inorganic phase layer, and add 2200L acetic acid Ethyl was extracted three times, combined to obtain the organic phase layer solution, the organic phase layer solution was dried, ethyl acetate was recovered, and vacuum distillation was used to collect the 180°C / 30mmHg column fraction, which was 1-chloro-4-tert-butyl-2- Nitrobenzene;

[0027] (2) Take 750Kg of 1-chloro-4-tert-butyl-2-nitrobenzene, take 75Kg of palladium carbon and 2600L of ethanol and put them into the reacto...

Embodiment 3

[0030] (1) Put 800Kg of p-tert-butylchlorobenzene into the reaction kettle A, and under the condition that the temperature of the reaction kettle A is controlled at 0°C, add the mixed acid of concentrated sulfuric acid and nitric acid at a temperature of 0°C dropwise, wherein the concentrated sulfuric acid is 800L, and the nitric acid After dripping, raise the temperature of reactor A to 20°C~25°C, stir reactor A, and react overnight. After the reaction is completed, pour the reaction solution into water to obtain an organic phase layer and an inorganic phase layer, and add 3000L acetic acid Ethyl was extracted three times, combined to obtain the organic phase layer solution, the organic phase layer solution was dried, ethyl acetate was recovered, and vacuum distillation was used to collect the 180°C / 30mmHg column fraction, which was 1-chloro-4-tert-butyl-2- Nitrobenzene;

[0031] (2) Take 1 ton of 1-chloro-4-tert-butyl-2-nitrobenzene, put 100Kg of palladium carbon and 3500L o...

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Abstract

The invention relates to a method for synthesizing 3-(tert-butyl)phenol. The method includes the following steps that 4-tert-butyl-1-chlorobenzene serves as a raw material and is nitrated to obtain 1-chlorine-4-tert-butyl-2-nitrobenzene; the 1-chlorine-4-tert-butyl-2-nitrobenzene is reduced to generate 3-tert-butylaniline; the 3-tert-butylaniline is diazotized and subjected to a hydrolysis reaction, and the 3-(tert-butyl)phenol is obtained. According to the path, the raw material is cheap and easy to get, elementary reaction conditions of the steps are mild, after-treatment is simple, the four-step reaction total yield is high, the 3-(tert-butyl)phenol with the purity higher than 97% can be obtained through distilling, and industrial production prospects are achieved.

Description

technical field [0001] The invention relates to the synthesis of a fine chemical intermediate, in particular to a synthesis method of m-tert-butylphenol. Background technique [0002] M-tert-butylphenol is an important fine chemical intermediate, especially as a raw material for the synthesis of the fungicide etoxazole. The molecular formula of m-tert-butylphenol is: C 10 h 14 O, its chemical name is: 3-tert-butyl-phenol, English name: 3-(tert-butyl)phenol; CAS number: 585-34-2; structural formula: [0003] In the synthetic process of m-tert-butylphenol, bibliographical information is arranged, and Pil'shchikov et al. report ( J.Appl.Chem.USSR (Engl.Transl) , 1981,2(54):2592-2595,2298-2300) take isobutylene and phenol as raw materials, through Friedel-Crafts reaction, obtain m-tert-butylphenol through rearrangement, the reaction by-products are more, and the yield is on the low side. Patent US2760991 reports that tert-butylbenzene is used as raw material, catalyzed by d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/05C07C39/06
CPCC07C37/05C07C201/08C07C209/36C07C39/06C07C211/45C07C205/12
Inventor 叶振君董建生袁绍志戴乙徐王正荣朱峰陆建华
Owner RUDONG ZHONGYI CHEM
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