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Synthesis method of high-purity bis-(p-carboxyphenylamino) phenylphosphine oxide flame retardant

A technology of phenylphosphine oxide and aniline, which is applied in the field of industrial production of pure flame retardant bis-(p-carboxyanilino)phenylphosphine oxide, can solve the problems of impure yield and low production rate, Achieve the effect of simple synthesis process, lower production cost and good product purity

Active Publication Date: 2021-03-23
HUBEI UNIV
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  • Description
  • Claims
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Problems solved by technology

[0003] The purpose of the present invention is to provide a kind of high-purity flame retardant bis-(p-carboxyanilino) phenylphosphine oxide synthesis method with simple and easy process and suitable for industrial production, so as to solve the problem of impure or impure target products of existing synthesis methods. The problem of low productivity

Method used

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  • Synthesis method of high-purity bis-(p-carboxyphenylamino) phenylphosphine oxide flame retardant
  • Synthesis method of high-purity bis-(p-carboxyphenylamino) phenylphosphine oxide flame retardant
  • Synthesis method of high-purity bis-(p-carboxyphenylamino) phenylphosphine oxide flame retardant

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Experimental program
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Embodiment 1

[0023]Weigh 5.00 g (0.030 mol) of ethyl p-aminobenzoate, 3.04 g (0.030 mol) of triethylamine, and 65 mL of solvent 1,4-dioxane in a reaction flask, stir and dissolve at room temperature, 2.93 g (0.015 mol) Phenylphosphoryl dichloride was mixed with 5.0mL 1,4-dioxane solvent, and then slowly added dropwise into the reaction bottle with a constant pressure dropping funnel. Cool in a bath, filter, wash with a small amount of solvent, transfer the solid to a beaker, add an appropriate amount of 1mol / L dilute hydrochloric acid to stir, beat, wash, filter, and then transfer the solid product to sesame cakes, add pure water to wash 1~2 times, until the pH of the washing liquid Value to 3 ~ 4, vacuum drying to give 2.96 g of light yellow solid product, the yield is about 43.6%.

[0024] Weigh 2.76 g (5.0 mmol) of the ester-based intermediate into a 100 mL single-necked bottle, add 30 mL of 70% (v / v) ethanol, heat the temperature of the external bath to 85 ° C, stir, and slowly dropwis...

Embodiment 2

[0026] Weigh 9.06 g (0.060 mol) of methyl p-aminobenzoate and 120 mL of solvent 1,4-dioxane in a reaction flask, stir and dissolve at room temperature, 2.93 g (0.015 mol) of phenylphosphoryl dichloride and 20.0 mL of 1 , After the 4-dioxane solvent is mixed, it is slowly dropped into the reaction bottle with a constant pressure dropping funnel at a constant speed. After the drop is completed, the temperature is raised to 45~50°C, and the reaction is carried out for 10 hours, cooled in an ice bath, filtered, and washed with a small amount of solvent. Transfer the solid to a beaker for later use. The filtrate is decompressed and rotary evaporated to recover the solvent. The residual liquid is mixed with the filtered solid. Add an appropriate amount of 1mol / L dilute hydrochloric acid to stir, beat, wash, and filter. The solid product is then transferred to the sesame cake and washed with pure water for 1~2 times, until the pH value of the washing solution reached 3~4, vacuum dryin...

Embodiment 3

[0029] Weigh 2.64g (0.016mol) of ethyl p-aminobenzoate in a 50ml three-neck flask, dissolve it in 20mL of 1,4-dioxane at room temperature, then weigh 0.78g (0.004mol) of phenylphosphoryl dichloride Dissolve it in 8 mL of 1,4-dioxane, slowly drop the phenylphosphoryl dichloride solution into the three-neck flask with a constant pressure titration funnel, and react at 70°C for 8 h after the addition is complete. After cooling to room temperature and filtering, the filter residue was washed twice with hydrochloric acid solution with a pH value of 2, and then washed twice with water until neutral and then dried to obtain a light yellow solid powder. The mass of the solid powder was 1.41 g, and the yield was 78.2%. The filtrate was evaporated under reduced pressure to recover the solvent, the raffinate was mixed with a small amount of ethanol, then stirred and dropped into 30mL 1mol / L hydrochloric acid for acidification washing, the solid was filtered and washed twice with water, a...

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Abstract

The invention relates to a synthesis method of a high-purity bis-(p-carboxyphenylamino) phenylphosphine oxide flame retardant. The method comprises the following steps: preparing a bis-(p-carboxyl phenylamino) phenyl phosphine oxide diethyl ester intermediate from ethyl p-aminobenzoate and phenyl phosphoryl dichloride in the molar ratio of 4 by taking 1, 4-dioxane as a solvent, the yield can reach84 percent, and carrying out alkaline saponification hydrolysis reaction,acidifying, washing and drying on the intermediate under the condition of an ethanol a-1, 4-dioxane-water mixed solution to obtain the target product.

Description

technical field [0001] The invention belongs to the chemical synthesis technology of organophosphorus flame retardants, and in particular relates to a preparation method of pure bis-(p-carboxyanilino)phenylphosphine oxide which can be industrially produced. Background technique [0002] Dicarboxylic acid phosphorus-containing compounds and their derivatives can often be used as halogen-free and environmentally friendly phosphorus-containing flame retardants in polyester or polyamide polymer materials, so that synthetic materials can achieve better flame-retardant effects. -carboxyanilino) phenylphosphine oxide belongs to this type of reactive flame retardants. US2882294 (1959) and Designed Monomers and Polymers, 2016, 19(5): 420-428 respectively reported bis-(p-carboxyanilino ) Application of phenylphosphine oxide and its derivatives in flame retardant polyester materials and polyamide materials. At present, the relevant bis-(p-carboxyanilino) phenylphosphine oxide and its ...

Claims

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Application Information

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IPC IPC(8): C07F9/44
CPCC07F9/448Y02P20/582
Inventor 李焰汪陈李超任君陈祖兴
Owner HUBEI UNIV
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