The Synthesis of Hybrid Hetero-Compounds by the Reaction between Phosphoryl Chloride and Aromatic Diol

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Other Title
  • 塩化ホスホリルと芳香族ジオールとの反応による混成異核化合物の合成
  • りん‐窒素化合物に関する研究　ＸＸＶＩ　　塩化ホスホリルと芳香族ジオールとの反応による混成異核化合物の合成

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In order to develop fireproof materials, an attempt was made to prepare the hybrid heterocompounds PO (X)2OR'OPO (X)2 (I) and (PDXOR'O-) (II) (R' = aromatic group, X =alkoxyl group or amide group) by means of a simple process. The conditions for the synthesis and the chracteristics of the products have been investigated.<BR>As an aromatic diols (HOR'OH), 2, 2-bis (p-hydroxyphenl) propane was suitable for the syntheses of (I) and (II). As the intermediate compound of (I), POCl2OR'OPOCl2 (I) was formed by the reflux of a mixture of 2 mol of POCl2 and 1 mol of HOR'OH. An oliy (I) was obtained by the esterification or the amidation of (I '). The addition of dehydrochlorination catalyst such as AlCl3 accelerated the reaction, and resulted a product containtng some cross linkage simultaneously. The intermediate compound of (II), (POClOR'0-)7, (IV), was obtained by the reflux of the equivalent mixture of POCl2 and HOR'OH dissolved in a small volume of dioxane. (U') could also be formed by the thermal dehydrochlorination of POCl2OR'OH, which was obtained by the exclusion of excess POCl2 from the reaction mixture, which is consisted of several mol of POCl2 and 1 mol of HOR'OH. A viscous oily produst was directly obtained by the esterification or the amidation of 01. However, the lump or powder of (I) and (II) could be obtained by the exclusion of a slight solvent included in the oily products.<BR>The products thus obtained were soluble in various organic solvents. P contents were 13∼14% in (I) and 8∼9% in (II), respectively. N contents were less than that of the expected as the result of the incomplete amidation. All the products contained traces of Cl. From the measurements of molecular weights, solubilities in organic solvents and the IR spectra, the products were estimated to be the condensation products of phosphate group with aromatic group. The resin containing more than ten percent of the products exhibited the incombustibility.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1975 (12), 2098-2104, 1975-12-10

    The Chemical Society of Japan

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