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Process for preparing 2,3,5-trimethylbenzoquinone by oxidation of 2,3,6-trimethylphenol

A technology for trimethylbenzoquinone and trimethylphenol, which is applied in the field of preparing 2,3,5-trimethylbenzoquinone by oxidation of 2,3,6-trimethylphenol, can solve high capital cost and Production costs, alkaline washing is not particularly effective, etc.

Active Publication Date: 2021-04-13
BASF SE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, alkaline washing is not particularly effective and always implies a trade-off between organochlorine compound reduction and product loss
In conclusion, this measure allows the technical implementation of the process according to scheme 3, but the additional process steps represented by the caustic washing result in higher capital and production costs, yield losses and, above all, only lead to the mitigation of the above-mentioned problems

Method used

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  • Process for preparing 2,3,5-trimethylbenzoquinone by oxidation of 2,3,6-trimethylphenol
  • Process for preparing 2,3,5-trimethylbenzoquinone by oxidation of 2,3,6-trimethylphenol
  • Process for preparing 2,3,5-trimethylbenzoquinone by oxidation of 2,3,6-trimethylphenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-10

[0052] A 4 L steel reactor was charged with 657 g of an aqueous reaction medium consisting of 151 g of CuCl 2 2H 2 O, 150g of LiCl and 365g of water. With stirring, the two-phase mixture is brought to the desired starting temperature T D , passing an oxygen-containing gas through it at atmospheric pressure. When reaching temperature T D , at a constant rate over time t D 500 g of a 60% strength by weight solution of 2,3,5-trimethylphenol (4) in alcohol used as solvent were fed in. To complete the reaction, at temperature T R Continue stirring time interval t R .

[0053] After the reaction was complete and after cooling to room temperature, the phases were separated and weighed individually, and the organic phase was analyzed. Conversion of (4) was complete (>99.9%) in all cases. There was little variation in the quinone (1 ) yield, which was in the range of 90-95% in all experiments. The results are described in Table 1.

[0054] As shown by the comparison of the e...

Embodiment 11

[0057] The reaction effluent from Example I7 (reaction in 3-heptanol) was first washed with water. When the phases were separated, they were extracted by shaking with aqueous HCl (25% by weight) and washed again with water. Sodium hydroxide solution (2% by weight) was added to bring the solution to a pH of 6, and the solvent was removed under reduced pressure to such an extent that a solution of trimethylbenzoquinone (1) with a concentration of about 75% by weight was obtained.

[0058] To determine the thermal stability of the crude product, it was heated to 110° C. and the amount of (1) was determined periodically by gas chromatography. After 125 hours, only 8% of (1) initially present underwent decomposition.

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Abstract

The present invention relates to the method for preparing 2,3,5-trimethylbenzoquinone or a compound comprising 2,3,5-trimethylbenzoquinone, said method comprising the following steps: 2,3,6-trimethylbenzoquinone Oxidation of phenol with oxygen or an oxygen-containing gas in a two-phase or heterogeneous reaction medium in the presence of a catalyst or catalyst system comprising at least one copper(II) halide to a compound comprising 2,3,5-trimethylbenzoquinone Mixtures characterized in that the reaction medium comprises water and at least one secondary aliphatic acyclic alcohol having 6 or more, preferably 7 or more carbon atoms.

Description

[0001] The application number is 201480037568.9, the application date is June 25, 2014, and the title of the invention is "Method for preparing 2,3,5-trimethylbenzoquinone by oxidation of 2,3,6-trimethylphenol" divisional application of the patent application. technical field [0002] The present invention provides a method for preparing 2,3,5-trimethylbenzoquinone or a mixture comprising 2,3,5-trimethylbenzoquinone, the method comprising the following steps: 2,3,6-trimethylbenzoquinone Oxidation of phenol with oxygen or an oxygen-containing gas in a two-phase or heterogeneous reaction medium in the presence of a catalyst or catalyst system comprising at least a copper(II) halide to give a mixture comprising 2,3,5-trimethylbenzoquinone , wherein the reaction medium comprises water and at least one secondary aliphatic acyclic alcohol having 6 or more, preferably 7 or more, carbon atoms. [0003] Another aspect of the invention relates to mixtures comprising 2,3,5-trimethylbenz...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C46/08C07C50/02C07D311/72C07C37/07C07C39/08
CPCC07C46/08C07C50/02C07D311/72Y02P20/584C07C50/04
Inventor R·德恩M·克劳斯M·德恩M·丹兹J·H·特莱斯
Owner BASF SE