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Method for synthesizing tert-butylated hydroxyanisole through solid-liquid-phase reaction

A technology for tert-butyl hydroxyanisole and tert-butyl hydroxyanisole is applied in the field of synthesizing tert-butyl hydroxyanisole by solid-liquid phase reaction, which can solve the problems of high cost, influence on catalyst activity, complicated preparation process, etc., so as to improve production The effect of efficiency

Inactive Publication Date: 2011-02-16
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in method (2) although the highest conversion rate is very high, but tert-butanol is used as the alkylating agent, during the reaction process The water produced will affect the activity of the catalyst. The catalyst is mainly Zn–Al-MCM-41 molecular sieve, the preparation process is complicated and the cost is high. Relatively speaking, The alkylation reagent methyl tert-butyl ether used avoids the generation of water in the reaction process. Currently known effective solid acid catalysts are mainly Filtrol-24 clay and K-10 montmorillonite Clay, the solvent is 1,4-dioxane (1,4-dioxane), or the catalyst is a heteropolyacid supported catalyst such as H3PW12O40 / Al2O3, but in general, the cost of these catalytic systems is relatively high, therefore, the present invention proposes a low-cost , the method for catalytically synthesizing tert-butylhydroxyanisole with good effect

Method used

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  • Method for synthesizing tert-butylated hydroxyanisole through solid-liquid-phase reaction
  • Method for synthesizing tert-butylated hydroxyanisole through solid-liquid-phase reaction
  • Method for synthesizing tert-butylated hydroxyanisole through solid-liquid-phase reaction

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add hydrogen-type Y molecular sieve catalyst (Si / Al molar ratio = 3:1, pre-treated by roasting at 500°C for 4 h), p-methoxyphenol, methyl tert-butyl ether and 10 mL solvent cyclohexane into a 20 mL autoclave The mixture of alkanes (the molar ratio of the three is 1:3:14.2), with N 2 The air in the reactor was replaced several times, and finally 0.3MPa of N 2 As a protective gas, keep the temperature at 160°C and react for 180 minutes. After the reaction, the reaction kettle is cooled rapidly, the reaction liquid and the catalyst are separated by suction filtration, and the content of p-methoxyphenol and tert-butylhydroxyanisole in the product is analyzed by gas chromatography. , to determine the conversion rate of p-methoxyphenol and the yield of tert-butylhydroxyanisole, the conversion rate of p-methoxyphenol was 97.9%, and the yield of tert-butylhydroxyanisole (TBHA) was 45.8%. The data are listed in Table 1.

Embodiment 2~6

[0027] Under the same conditions as in Example 1, the reaction time was changed (15 min, 30 min, 60 min, 90 min, 120 min respectively), and the results are listed in Table 1 (2-6).

Embodiment 7~11

[0029] Under the same conditions as in Example 1, the reaction temperatures were changed (80°C, 100°C, 120°C, 140°C, 180°C, respectively), and the reaction results were listed in Table 1 (7-11).

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PUM

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Abstract

The invention provides a method for synthesizing tert-butylated hydroxyanisole under the catalytic action of a hydrogen Y molecular sieve by using p-methoxy phenol and methyl tert-butyl ether as raw materials. In the method, the Y molecular sieve with a hydrogen Si / Al ratio of 2.6-7.6 is used, the reaction time is 15-180 min, the reaction temperature is 80-180 DEG C, the p-methoxy phenol conversion rate is 21-99 percent and the tert-butylated hydroxyanisole yield is 14-74 percent. The invention adopts a catalyst which has low cost and can be repeatedly used through simple solvent washing or roasting treatment, can solve the problems of unavailable catalyst recovery and great acidic wastewater discharge of a traditional tert-butylated hydroxyanisole production process through an F-C (Friedel-Crafts) reaction and has important industrial application prospects, and meanwhile, the catalyst and the reaction process, adopted in the method, benefits the improvement of the production efficiency.

Description

[0001] technical field [0002] The invention relates to a method for synthesizing antioxidant-tert-butylhydroxyanisole by using p-methoxyphenol and methyl tert-butyl ether as raw materials under the action of a hydrogen-type Y molecular sieve catalyst. [0003] Background technique [0004] Tert-butylhydroxyanisole (butylatedhydroxyanisole, also known as tert-butyl-4-hydroxyanisole, butyl anisole), including 3-tert-butyl-4-hydroxyanisole (3-TBHA) and 2-tert-butyl 4-Hydroxyanisole (2-TBHA) is a white to light yellow waxy solid with a slight specific odor and a melting point of 48-63°C. It is stable to heat. Under weak alkaline conditions, it is not easy to be destroyed, and it will not be colored when it interacts with metal ions. [0005] Tert-butyl hydroxyanisole is an important oil-soluble antioxidant, which is mainly used in food and oil industry, and can also be used in petroleum processing and rubber. (References: Edited by Zheng Yuguo, Wang Yuanshan, etc., "Product...

Claims

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Application Information

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IPC IPC(8): C07C43/23C07C41/30B01J29/08
CPCY02P20/584
Inventor 毛建新罗云蔡黄菊卞妮妮郑小明
Owner ZHEJIANG UNIV
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