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DOPO flame retardant isomer conversion method

An isomer and flame retardant technology, which is applied in the field of DOPO flame retardant isomer conversion, can solve the problems of low yield, affect application, and complicated operation, and achieve the effect of increasing content, wide application and good performance.

Inactive Publication Date: 2019-01-04
CENTRAL SOUTH UNIVERSITY OF FORESTRY AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

This patent uses DOPO and ethylene glycol (EG) as raw materials to synthesize the derivatives of DOPO, and the resulting product is a mixture (enantiomer) containing three isomers of compound I, wherein compound I (RS type) The melting point is the highest, due to the existence of two other low-melting point isomers IIa (RR type) and IIb (SS type), the melting point of the product is only about 250 degrees, which affects its application in some special fields
At the same time, the patent pointed out that acid catalysts can be used to convert low-melting point isomers into high-melting point isomers, but the operation is cumbersome and the yield is low

Method used

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  • DOPO flame retardant isomer conversion method
  • DOPO flame retardant isomer conversion method
  • DOPO flame retardant isomer conversion method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Add 100 g of a composition containing 30% of the compound of formula I (the content of formula IIa and formula IIb is 70%) into 450 ml of ethylene glycol dimethyl ether, add 25 g of a 60% mass fraction of D-tartaric acid aqueous solution, heat and reflux for 6 hours, and cool to room temperature, add 500ml of acetone, stir, filter, wash with acetone, and dry to obtain 98.56g of white solid, sampled 31 P NMR results showed that the proportion of the high melting point isomer formula I compound was 99.3%.

Embodiment 2

[0021] Add 40 g of a composition containing 30% of the compound of formula I (the content of formula IIa and formula IIb is 70%) to 250 ml of diphenylmethane, add 6 g of 90% D-tartaric acid aqueous solution by mass fraction, heat and reflux for 4 hours, and cool to room temperature. Add 250ml of acetone, stir, filter, wash with acetone, and dry to obtain 37.94g of white solid, sampled 31 P NMR results showed that the proportion of the high melting point isomer formula I compound was 99.7%.

Embodiment 3

[0023] 30g of the composition containing 30% of the compound of formula I (70% of formula IIa and formula IIb content) was added to 150ml of DMF, 4.5g of 70% mass fraction of D-tartaric acid aqueous solution was added, heated to reflux for 6h, cooled to room temperature, added 150ml of isopropanol, stirred, filtered, washed with isopropanol, dried to obtain 28.12g of white solid, sampled 31 P NMR results showed that the high melting point isomer ratio was 98.9%.

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Abstract

The invention provides a DOPO flame retardant isomer conversion method. According to the method, a D-tartaric acid solution is put into a mixture containing low-melting point isomers, then the low-melting point isomers can be converted into a high-melting point isomer with high application values, the high-melting point isomer has high properties when being used as a flame retardant and has wide application.

Description

technical field [0001] The invention relates to a method for converting DOPO flame retardant isomers. Background technique [0002] Brominated flame retardants will cause harm to the environment in their application, and more environmentally friendly phosphorus-based flame retardants have gradually received attention and development. In the field of epoxy resin sheets, the application of additive phosphorus flame retardants is relatively rare, because it has high requirements on the melting point and stability of flame retardants, and it is difficult for general flame retardants to meet the requirements. [0003] Patent WO2011123389A1 reports a DOPO derivative compound I, which is considered to be a very potential flame retardant in the field of epoxy resin. This patent uses DOPO and ethylene glycol (EG) as raw materials to synthesize the derivatives of DOPO, and the resulting product is a mixture (enantiomer) containing three isomers of compound I, wherein compound I (RS t...

Claims

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Application Information

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IPC IPC(8): C07F9/6574
CPCC07F9/657172
Inventor 郭鑫袁寒梦王元兰张贵王文磊马强肖滕
Owner CENTRAL SOUTH UNIVERSITY OF FORESTRY AND TECHNOLOGY
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