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Process for the production of quinone methide

A technology of quinone methide and benzylidene, applied in the field of 4-benzylidene-2, which can solve the problems of increasing raw material cost and processing cost

Inactive Publication Date: 2009-09-23
GENERAL ELECTRIC CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generation of these by-products increases raw material and disposal costs

Method used

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  • Process for the production of quinone methide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment I

[0023] To a 500 ml RB flask equipped with a Dean Stark (connected to a water-cooled reflux condenser) was added 51.3 g of 2,6-di-tert-butylphenol, 26.5 g of benzaldehyde and 46 g of N,N- Di-n-propyl-amine. The mixture was heated at 130° C. for 9.5 hours in an oil bath placed on a magnet under a nitrogen atmosphere with stirring. Afterwards, the reaction mixture was distilled under vacuum at 114° C. for 4 hours. The initial vacuum was 250mmHg for 2-3 hours. Afterwards, the vacuum was slowly reduced to 10 mmHg and maintained at this value until the end of the reaction. The weight of the final product was 73.2 g, and the weight of the distillate after separation of the water was 44 g. The content of quinone methide in the product is 84.79%.

Embodiment II

[0025] Into a 500ml RB flask was added 26.5g benzaldehyde and 32.3g N,N-di-n-butylamine. The mixture was maintained at 70°C for 30 minutes. Afterwards, 51.5 g of 2,6-di-tert-butyl-phenol were added, and the mixture was maintained at 115-118° C. for 30 hours. To recover the amine, the reaction mixture was distilled at 130° C. under 30 mmHg vacuum for 5 hours, after removal of N,N-di-n-butylamine by distillation, 69.78% of quinone methides were found in the product.

Embodiment III

[0027]Into a 500ml RB flask was added 21.4g benzaldehyde and 41.2g N,N-di-n-butylamine, and 26g 2,6-di-tert-butyl-phenol was added. The mixture was maintained at 110°C for 12 hours. Afterwards, the reaction mixture was subjected to amine distillation at 110° C. at 30 mmHg for 1.5 hours. The vacuum was slowly reduced to 6 mmHg, and distillation was continued for an additional 2.0 hours. After distillation of N,N-di-n-butyl-amine, the final product in the reaction flask was shown to have 63.82% quinone methides.

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Abstract

This invention relates to a process for the production of quinone methide and more particularly to a method for process which optimizes the production of quinone methide, in particular 4-Benzylidene-2,6-di-te / t-butyl-cyclohexa-2,5- dienone, while limiting the production of by products or waste.

Description

technical field [0001] The present invention relates to a process for the preparation of quinine methides; more particularly, the present invention relates to a process for optimizing the production of quinine methides while limiting by-product or waste generation. In particular 4-benzylidene-2,6-di-tert-butyl-cyclohexa-2,5-dienone. Background technique [0002] It is known to prepare quinone methides by reacting 2,6-di-tert-butyl-phenol with benzaldehyde and dimethylamine to give 2,6-di-tert-butyl-4-(dimethylamino-benzene quinone methide (ie, 4-benzylidene-2,6-di-tert-butyl-cyclohexa-2,5-dienone). However, when this method is followed, in addition to the formation of the quinone methide, other compounds are formed as by-products, specifically, dimethylamine and acetic anhydride are secondary and final by-products of the process (i.e., dimethylacetamide and acetic acid). The generation of these by-products increases raw material costs and disposal costs. The use of quino...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C45/45
CPCC07C45/45C07C49/417
Inventor 维诺德·K·雷
Owner GENERAL ELECTRIC CO
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