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Method for producing phosphoric acid ester amides

A technology of phosphate amide and dihalophosphate, which is applied in the new manufacturing field of phosphate amide, and can solve problems such as residues and complicated procedures

Active Publication Date: 2015-03-04
DAIKYO CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, with regard to these amines, the more aromatic the amines, the more they may not function effectively as a hydrogen chloride scavenger. In addition, in order to recover and reuse the amines from their hydrochloride salts after the completion of the reaction, similarly complicated procedures are required. process
Moreover, according to such a method, the odor generated by the amine used may remain in the obtained anilino diphenyl phosphate

Method used

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  • Method for producing phosphoric acid ester amides
  • Method for producing phosphoric acid ester amides
  • Method for producing phosphoric acid ester amides

Examples

Experimental program
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Effect test

Embodiment 1

[0170] 9.8 g (0.105 mol) of aniline and 35 mL of mesitylene were put into the round bottom flask at normal temperature, and aniline was dissolved in mesitylene. While stirring the obtained solution, 26.9 g (0.100 mol) of diphenylphosphoryl chloride was slowly added dropwise to the solution over 10 minutes while keeping the solution at 40° C. or lower. At this time, anilino diphenyl phosphate and aniline hydrochloride precipitated from the above solution, and the reaction mixture became a dispersion liquid containing the above precipitates.

[0171] After completion of the dropwise addition, the temperature of the reaction mixture was gradually raised to 170 to 180° C. over 30 minutes, and the reaction was carried out at the same temperature as above for 1 hour while refluxing trimethylbenzene. From the time when the temperature of the reaction mixture exceeded 100° C., anilinodiphenyl phosphate was dissolved in mesitylene, and only aniline hydrochloride was deposited as a disp...

Embodiment 2

[0175] In Example 1, except having used 11.2 g (0.120 mol) of aniline, it carried out similarly, and obtained 30.5 g of anilino diphenyl phosphates. The yield relative to aniline was 78.2%. The melting point is 132.0°C.

Embodiment 3

[0177] In Example 1, except having used 9.30 g (0.100 mol) of aniline and 33.6 g (0.125 mol) of diphenylphosphoryl chloride, it carried out similarly, and obtained 29.5 g of anilino diphenyl phosphates. The yield relative to diphenylphosphoryl chloride was 72.6%. The melting point is 131.2°C.

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Abstract

Provided is a method for dehydrohalogenating phosphoro-monohalidates and an amine compound having one or two primary amino groups and / or secondary amino groups in the molecule, and producing phosphoric acid ester amides corresponding to the phosphoro-monohalidates; wherein the method includes reacting the phosphoro-monohalidates and the amine compound at a temperature of 130°C or higher without using an excess of amine compound relative to the phosphoro-monohalidates.

Description

technical field [0001] The present invention relates to a novel process for the manufacture of phosphate ester amides. Background technique [0002] Phosphate ester amides are used as flame retardants in, for example, synthetic resin moldings and fiber products (see, for example, Patent Document 1), and several production methods are known. [0003] For example, anilino diphenyl phosphate, which is a representative example of phosphate ester amides, can usually be obtained by a condensation reaction between diphenylphosphoryl chloride and aniline, that is, a dehydrochlorination reaction. [0004] In this reaction, when diphenylphosphoryl chloride and aniline each use 1 equivalent, 0.5 equivalent of aniline reacts with 0.5 equivalent of diphenylphosphoryl chloride to generate the target anilino diphenyl phosphate, but the remaining 0.5 equivalent of aniline acts as a hydrogen chloride scavenger to form hydrochloride, so 0.5 equivalent of diphenylphosphoryl chloride remains a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/24
CPCC07F9/650958C07F9/6533C07F9/2462C07F9/2458C07F9/247C07F9/6552C07F9/2475C07F9/650952
Inventor 青原義一田中良典
Owner DAIKYO CHEM
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