Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Studies on Nitrogen-Phosphorus Compounds. XXII. The Synthesis and Properties of Phosphoric Aniline Diamide
Etsuro Kobayashi
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1973 Volume 46 Issue 1 Pages 183-186


In order to develop fireproof materials, a new compound, phosphoric aniline diamide, was prepared by employing phosphorus oxychloride, aniline, and ammonia as the starting materials. The conditions for the synthesis and the characteristics of the product have been investigated. Phosphoric aniline diamide can be prepared in the following way: 2 moles of aniline are added to 1 mole of phosphorus oxychloride diluted with chloroform, and the precipitate of aniline hydrochloride, a by-product, is separated from the solvent by filtration. A mixture of phosphoric amide and ammonium chloride is formed by the reaction between an excess of gaseous ammonia and the above filtrate at −10–20°C, and is then separated from the mother liquor. Crude phosphoric amide is extracted from the mixture with ethanol, and subsequent re-extraction with acetone yields the pure product with the formula PONHC6H5(NH2)2. The product thus obtained is composed of a white crystalline powder, soluble in water, ethanol and acetone but insoluble in various organic solvents. The compound shows its own characteristic X-ray diffraction pattern and IR absorption bands. Upon heating, the product melts at about 140°C; condensation occurs by de-ammoniation above 170°C, and conversion into insoluble condensed amidophosphates takes place.

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