Method for catalytic synthesis of 2,3,5-trimethylbenzoquinone

A technology of trimethylbenzoquinone and trimethylphenol, which is applied in the field of vitamin E intermediate preparation, can solve the problems of high solvent toxicity, high price, and difficult separation, and achieve high synthesis efficiency

Inactive Publication Date: 2017-12-19
CHONGQING IND POLYTECHNIC COLLEGE
View PDF2 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current one-step oxidation synthesis method mainly uses trimethylphenol (mostly 2,3,6-trimethylphenol) as raw material, and uses metal salts as catalysts in acetic acid, acetonitrile, ionic liquids and other solvents to catalyze Oxygen (air) or H 2 o 2 The raw material is oxidized to obtain trimethylbenzoquinone, but these methods have the following problems: (1) the solvent used is highly toxic, easily corroded equipment or solvent synthesis steps are many, and the price is high; (2) the catalyst used in most cases is a metal salt, great difficulty in separating

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] Example 1, preparation of copper-based micro-mesoporous catalyst: take 1% copper nitrate and the remainder of Si:Al as ZSM-5 precursor (this precursor is commercially available) of 50:1 by mass percentage, The weighed copper nitrate was dissolved in water, the mass ratio of the added water to the ZSM-5 precursor was 400:1, then dilute nitric acid was added to adjust the pH to 4.0, then the weighed ZSM-5 precursor was added, and stirred for 12 hours at room temperature , filtered and dried and calcined at 400°C for 8h to obtain a Cu-ZSM-5 catalyst with a copper content of 1%.

[0017] Preparation of 2,3,5-trimethylbenzoquinone: Weigh 1 mmol of 2,3,6-trimethylphenol and 20 mg of the Cu-ZSM-5 catalyst prepared in this example into a round bottom flask, add 0.45 mL 30% H 2 o 2 Hydrogen peroxide, 30mL of methanol, install a condenser, control the reaction temperature at 60°C, react for 3h, stop the reaction, cool, filter, and analyze the reaction filtrate with HPLC. The sp...

Embodiment 2

[0018] Example 2, preparation of copper-based micro-mesoporous catalyst: take 1% copper nitrate and the remainder of Si:Al by mass percentage respectively as the ZSM-5 precursor (this precursor is commercially available) of 20:1, The weighed copper nitrate was dissolved in water, the mass ratio of the added water to the ZSM-5 precursor was 100:1, then dilute nitric acid was added to adjust the pH to 5.0, then the weighed ZSM-5 precursor was added, and stirred for 13 hours at room temperature , filtered and dried and calcined at 550°C for 12h to obtain a Cu-ZSM-5 catalyst with a copper content of 1%.

[0019] Preparation of 2,3,5-trimethylbenzoquinone: Weigh 1 mmol of 2,3,6-trimethylphenol and 30 mg of the Cu-ZSM-5 catalyst prepared in this example into a round bottom flask, add 0.60 mL 30% H 2 o 2 Hydrogen peroxide, 30mL of methanol, install a condenser tube, control the reaction temperature to 60°C, react for 3h, stop the reaction, cool, filter, and analyze the reaction fil...

Embodiment 3

[0020] Example 3, preparation of copper-based micro-mesoporous catalyst: take 3% copper nitrate and the remaining Si:Al by weight percentage respectively ZSM-5 precursor (this precursor is commercially available) that is 40:100 by mass percentage, The weighed copper nitrate was dissolved in water, the mass ratio of the added water to the ZSM-5 precursor was 200:1, then ammonia water was added to adjust the pH to 8.0, and then the weighed ZSM-5 precursor was added, and stirred for 14 hours at room temperature. After filtering and drying, it was calcined at 550° C. for 9 h to obtain a Cu-ZSM-5 catalyst with a copper content of 3%.

[0021] Preparation of 2,3,5-trimethylbenzoquinone: Weigh 1 mmol of 2,3,5-trimethylphenol and 10 mg of the Cu-ZSM-5 catalyst prepared in this example into a round bottom flask, add 0.30 mL 30% H 2 o 2 Hydrogen peroxide, 50mL of methanol, install a condenser, control the reaction temperature at 60°C, react for 6h, stop the reaction, cool, filter, and...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a method for catalytic synthesis of 2,3,5-trimethylbenzoquinone. The method comprises the following steps: weighing trimethylphenol and Cu-ZSM-5 catalyst according to a mass ratio of 10:(1-3):1, adding a polar solvent and an oxidant, carrying out a reaction at 30-80 DEG C for 2-6 h, and filtering the obtained reaction product to obtain a filtrate which is the 2,3,5-trimethylbenzoquinone. The Cu-ZSM-5 catalyst having the stability of a traditional catalyst and the also having the characteristics of a micro-mesoporous material selectively catalytically oxidizes 2,3,5-trimethylphenol or 2,3,6-trimethylphenol into the 2,3,5-trimethylbenzoquinone in water, methanol, ethanol, a mixture solvent thereof or other green solvents under the action of H2O2, so the synthesis efficiency is high, and the Cu-ZSM-5 catalyst has no inactivation or collapsing phenomenon after being used multiple times. The method for synthesizing the 2,3,5-trimethylbenzoquinone is a new 2,3,5-trimethylbenzoquinone synthesis method having a high efficiency and an environmental protection property.

Description

technical field [0001] The invention relates to the technical field of preparation of vitamin E intermediates, in particular to a method for catalytically synthesizing 2,3,5-trimethylbenzoquinone. Background technique [0002] 2,3,5-Trimethylhydroquinone (TMHQ) is an important intermediate for the preparation of vitamin E, and 2,3,5-trimethylbenzoquinone (TMBQ) is an important precursor compound for the synthesis of TMHQ. At present, the methods for synthesizing TMBQ mainly include multi-step reaction synthesis and one-step oxidation synthesis. In the multi-step reaction synthesis method, the most important synthesis method is to obtain the target product after a series of reactions such as sulfonation, nitration, oxidation, etc., using mesitylene as a raw material. This method requires the use of a large amount of acid and produces a large amount of Salt wastewater has serious environmental pollution, and the reaction needs to be strictly controlled at a lower temperature ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/06C07C50/02B01J29/46
CPCB01J29/044B01J29/46B01J2229/18B01J2229/37B01J2229/38C07C46/06C07C50/02
Inventor 吴明珠李应李德聪何得粮汪秋豪程坤
Owner CHONGQING IND POLYTECHNIC COLLEGE
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap