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Green preparation process of m-tert-butylphenol

A technology for m-tert-butylphenol and tert-butylphenol, which is applied in the field of green preparation technology of m-tert-butylphenol, can solve the problems of serious environmental pollution, many by-products and high yield, and achieves simple process, economic benefits and high yield. Improved social benefits and good atomic economy

Pending Publication Date: 2020-03-24
广州市金柏利发展有限公司
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0004] U.S. Patent US4103096 reports the synthesis route of m-tert-butylphenol, which takes p-tert-butylphenol as raw material and 1%-5% trifluoromethanesulfonic acid as catalyst, under the condition of 120°C-240°C, continuous Heating until the content of tert-butylphenol in the middle of the reaction liquid reaches the highest, and the yield can reach 35%. This method has simple reaction steps, but the temperature requirement is high, and the reaction process is difficult to control, and there are many by-products
The literature Speciality Petrochemicals, 2015, 32, pp 53-55 introduces another synthesis method of m-tert-butylphenol, which uses p-tert-butylchlorobenzene as a raw material, undergoes nitration, diazotization, and hydrolysis to obtain m-tert-butyl phenol, this method has high yield and is easy to operate, but the diazotization reaction is not conducive to industrial production and serious environmental pollution
Document Journal of Organic Chemistry, 1951,16, pp 586-617 introduces m-tert-butylaniline as raw material, and obtains product by diazotization hydrolysis reaction. Chemical reactions are high-risk operations in industrial production
The document Journal of Applied Chemistry, 1981, 54, pp2592-2595 reported that isobutylene and phenol were used as raw materials to obtain m-tert-butylphenol through Friedel-Crafts reaction, but the reaction had many by-products and the yield was low
In addition, the patent US2760991 reported that tert-butylbenzene was used as raw material, catalyzed by divalent copper ions, and the product could be obtained by reaction at high temperature. The reaction temperature was high, the requirements for equipment were high, and there were many by-products, which was not conducive to large-scale production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1) 10g of phenol, 0.1g of clay and 50mg of sulfuric acid are added to the round-bottomed reaction flask, the reaction temperature is controlled at 150°C, and 15ml of tert-butyl chloride is added dropwise, the dropwise is completed, and stirred for 3 hours. After the reaction is completed, Filter out the catalyst, pour the reaction solution into 100ml of water to obtain an organic phase layer and an inorganic phase layer, add 300ml ethyl acetate to extract three times, combine to obtain an organic phase layer solution, and the organic phase layer solution is washed with anhydrous NaSO 4 Dry, recover ethyl acetate, distill under reduced pressure, collect 125~130°C / 20mmHg fractions to obtain m-tert-butylphenol with a purity of 98.0%, such as figure 2 as shown, 1 H NMR (400MHz, CDCl 3 )δ7.26(s,1H),7.18(t,J=8.0Hz,1H),6.97(d,J=7.8Hz,1H),6.89–6.85(m,1H),6.64(d,J=8.4 Hz, 1H), 1.30 (s, 9H), liquid chromatography retention time t = 26.733min (methanol: water = 1:1), collect 1...

Embodiment 2

[0028] (1) 20g phenol, 0.17g clay and 75mg sulfuric acid are added in the round-bottomed reaction flask, and the reaction temperature is controlled at 150°C, and 19ml tert-butyl chloride is added dropwise, and the dropwise is completed and stirred for 3 hours. After the reaction is completed, Filter out the catalyst, pour the reaction solution into 200ml of water to obtain an organic phase layer and an inorganic phase layer, add 400ml ethyl acetate to extract three times, combine to obtain an organic phase layer solution, and the organic phase layer solution is washed with anhydrous NaSO 4 Dry, recover ethyl acetate, distill under reduced pressure, collect fractions at 125-130°C / 20mmHg to obtain m-tert-butylphenol with a purity of 97.1%, collect fractions at 110-115°C / 10mmHg to obtain p-tert-butylphenol, collect 82- 87 ° C / 20mmHg fraction, phenol.

[0029] (2) 1.9g aluminum chloride and 0.14g white clay are added in the round-bottomed reaction flask, add the 10g p-tert-butyl...

Embodiment 3

[0031] (1) 35g phenol, 0.28g clay and 115mg sulfuric acid are added in the round-bottomed reaction flask, and the reaction temperature is controlled at 150°C, and 29ml of tert-butyl chloride is added dropwise, and the dropwise is completed and stirred for 3 hours. After the reaction is completed, Filter out the catalyst, pour the reaction solution into 400ml of water to obtain an organic phase layer and an inorganic phase layer, add 600ml ethyl acetate to extract three times, combine to obtain an organic phase layer solution, and the organic phase layer solution is washed with anhydrous NaSO 4 Dry, recover ethyl acetate, distill under reduced pressure, collect fractions at 125-130°C / 20mmHg to obtain m-tert-butylphenol with a purity of 98.3%, collect fractions at 110-115°C / 10mmHg to obtain p-tert-butylphenol, collect 82- 87 ° C / 20mmHg fraction, phenol.

[0032] (2) 2.6g aluminum chloride and 0.19g white clay are added in the round-bottomed reaction flask, add the 15g p-tert-b...

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Abstract

The invention discloses a preparation process of m-tert-butylphenol. The method includes the steps of: (1) adopting phenol and tert-butyl chloride as the raw materials, taking acidic clay and concentrated sulfuric acid as the catalyst, carrying out alkylation reaction to obtain the main product m-tert-butylphenol and the byproduct p-tert-butylphenol by one step, and performing separation; and (2)taking unreacted phenol and the p-tert-butylphenol by-product obtained in the step (1) as the raw materials, and taking acidic clay and aluminum trichloride as the catalyst, and carrying out rearrangement reaction to obtain m-tert-butylphenol in one step. Compared with the prior art, the preparation process of m-tert-butylphenol provided by the invention has the advantages of cheap and easily available raw materials, simple technology, good atom economy, greenness and environmental protection, is suitability for industrial production, and has important practical significance for improvement ofthe economic and social benefits of the tert-butylphenolation industry.

Description

technical field [0001] The invention relates to a synthesis method of a fine chemical intermediate, in particular to a green preparation process of m-tert-butylphenol. Background technique [0002] As a derivative of phenol, m-tert-butylphenol is an important fine chemical intermediate, especially as a raw material for the synthesis of fungicide etoxazole and anoxol mould, and its isomer p-tert-butylphenol It is an important chemical raw material for the production of polycarbonate resin, rubber, paint, ink, flame retardant, pharmaceutical intermediates and other products in China. However, China's tert-butylphenol industrial technology lags behind and mainly relies on imports, and the price is expensive (m-tert-butylphenol is about 400,000 yuan / ton). The per capita consumption of tert-butylphenol is only 2% of that of the United States and 2.5% of that of Japan. %, the annual production capacity is seriously insufficient, only 3,000 tons. The molecular formula of m-tert-b...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C39/06C07C37/18C07C37/48
CPCC07C37/18C07C37/48
Inventor 黄德春周亚涵赵兵兵陈家鑫陈维
Owner 广州市金柏利发展有限公司
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