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Manufacture method of p, p-dibenzoylquinone dioxime compounds

A technology of dibenzoylbenzoquinone dioxime and p-benzoquinone dioxime, which is applied in the right field, can solve the problems of increasing product production cost, low product yield, and low purity of finished products, and achieves production cost reduction and product purity. High and easy-to-obtain raw materials

Inactive Publication Date: 2014-12-17
玛耀生物医药(上海)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When p-dibenzoylquinone dioxime is produced in the existing industry, low-boiling point chloroform is usually used as solvent, which is volatile and difficult to recycle. In addition, the product yield is not high, and the purity of the finished product is low, requiring recrystallization, increasing product production cost

Method used

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  • Manufacture method of p, p-dibenzoylquinone dioxime compounds
  • Manufacture method of p, p-dibenzoylquinone dioxime compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Add 10g of p-benzoquinone dioxime (0.0724mol) into a 250ml four-necked flask, then add 60g of ethylene glycol dimethyl ether, stir evenly, and slowly add 1.46g of triethylamine ( 0.0145mol) and 25.44g benzoyl chloride (0.181mol), after the dropwise completion, the reaction was incubated at room temperature for 2 hours.

[0015] After the heat preservation is finished, filter and reclaim the filtrate, wash the filter cake twice with 10g ethylene glycol dimethyl ether (5g each time), reclaim the washing liquid, wash once with 10ml water, and drain to obtain the product p-para-benzophenone Acylbenzoquinone dioxime was placed in an oven and dried at 90°C to obtain 23.98 g of the finished product, with a yield (based on p-benzoquinone dioxime) of 95.61% and a purity of 96.2% (HPLC).

Embodiment 2

[0017] Add 10g of p-benzoquinone dioxime (0.0724mol) into a 250ml four-necked flask, then add 60g of ethylene glycol dimethyl ether, stir evenly, and slowly add 1.06g of N,N-dimethoxy Methylformamide (0.0145 mol) and 25.44 g of benzoyl chloride (0.181 mol) were left to react at room temperature for 2 hours after the dropwise completion.

[0018] After the heat preservation is finished, filter and reclaim the filtrate, wash the filter cake twice with 10g ethylene glycol dimethyl ether (5g each time), reclaim the washing liquid, wash once with 10ml water, and drain to obtain the product p-para-benzophenone Acylbenzoquinone dioxime was dried in an oven at 90°C to obtain 23.7 g of the finished product, with a yield (calculated as p-benzoquinone dioxime) of 94.50% and a purity of 95.3% (HPLC).

Embodiment 3

[0020] Add 10g of p-benzoquinone dioxime (0.0724mol) into a 250ml four-necked flask, then add 60g of ethylene glycol dimethyl ether, stir evenly, and slowly add 1.15g of pyridine (0.0145mol ) and 25.44g benzoyl chloride (0.181mol), after the dropwise completion, the reaction was incubated at room temperature for 2 hours.

[0021] After the heat preservation is finished, filter and reclaim the filtrate, wash the filter cake twice with 10g ethylene glycol dimethyl ether (5g each time), reclaim the washing liquid, wash once with 10ml water, and drain to obtain the product p-para-benzophenone Acylbenzoquinone dioxime was placed in an oven and dried at 90°C to obtain 23.8 g of finished product, the yield (based on p-benzoquinone dioxime) was 94.89%, and the purity was 95.5% (HPLC)

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Abstract

The invention provides a manufacture method of p, p-dibenzoylquinone dioxime compounds. According to the manufacture method, dimethoxyethane is used as solvents, benzoquionone dioxime and benzoyl chloride are used as raw materials to be reacted, and in addition, acid-binding agents are added in the reaction for manufacture. The reaction equation is shown as the accompanying drawing. The solvents used in the method provided by the invention are the dimethoxyethane, the boiling point is higher, the volatilization is not easy to occur, the total recovery can be realized, the utilization rate is high, a small number of the acid-bonding agents are added, the yield is improved and reaches higher than 95 percent (the reported yield in the prior art is about 78 percent), the product purity is high, the purity can reach higher than 95 percent with no need of the recrystallization of products, the reaction is carried out at the room temperature, the production cost is low, the operation is convenient, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to organic synthesis, in particular to a preparation method of p-, p-dibenzoylquinone dioxime. Background technique [0002] Yes, p-dibenzoylquinone dioxime is a rubber vulcanizing agent. It is usually synthesized from p-benzoquinone dioxime, which belongs to quinone vulcanizing agent with p-benzoquinone dioxime, and has similar properties. However, because p-dibenzoylquinone dioxime contains a benzoyl group in its structure, it has stronger vulcanization delay than p-benzoquinone dioxime and is less likely to burn. During vulcanization, p-, p-dibenzoylquinone dioxime uses dibenzothiazole disulfide as an accelerator to form a quinone oxime vulcanization system, which has a fast vulcanization speed, good electrical properties and aging resistance, and can improve The heat resistance and ozone resistance of the product are suitable for butyl rubber, natural vulcanization mortar, tire vulcanization water tire, electric wire, heat-r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/68C07C249/12
CPCY02P20/582
Inventor 陈品岗
Owner 玛耀生物医药(上海)有限公司
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