Acta Chimica Sinica ›› 2007, Vol. 65 ›› Issue (18): 2034-2038. Previous Articles     Next Articles

Original Articles

N,N'-二(二乙氧基硫代磷酰基)-1,4-苯二胺的合成、晶体结构及热性能研究

任元林*, 程博闻, 张金树, 藏洪俊, 康卫民, 丁长坤   

  1. (天津工业大学天津市纤维改性及功能纤维重点实验室 天津 300160)
  • 投稿日期:2006-12-28 修回日期:2007-03-05 发布日期:2007-09-28
  • 通讯作者: 任元林

Synthesis, Crystal Structure and Thermal Properties of N,N'-Di(diethoxythiophosphoryl)-1,4-phenylenediamine

REN Yuan-Lin*; CHENG Bo-Wen; ZHANG Jin-Shu; ZANG Hong-Jun; KANG Wei-Min; DING Chang-Kun   

  1. (Tianjin Municipal Key Laboratory of Fiber Modification and Functional Fiber, Tianjin Polytechnic University, Tianjin 300160)
  • Received:2006-12-28 Revised:2007-03-05 Published:2007-09-28
  • Contact: REN Yuan-Lin

The title compound N,N'-di(diethoxythiophosphoryl)-1,4-phenylenediamine was synthesized by the reaction of diethoxythiophosphoryl chloride and p-phenylenediamine and characterized by elemental analysis, IR and 1H NMR spectra. Its crystal structure was determined by single crystal X-ray diffraction analysis and the thermal property was studied by TG analysis. The relative molecular weight of the title compound is 412.42, the crystal structure belongs to orthorhombic, Pbca space group, with a=0.86936(16) nm, b=1.2787(2) nm, c=1.8897(3) nm, β=90°, V=2.1006(7) nm3, Z=8, Dc=1.304 g/cm3, μ(Mo Kα)=0.425 mm-1, F(000)=872, S=1.052, the final R=0.0628 and wR=0.1860 for 1852 observed reflections with I>2σ(I). The X-ray single crystal diffraction analysis demonstrates that the crystal structure is centrosymmetric. The weak N—H…S intramolecular hydrogen bonds were observed to link the molecules into sheets. The TG analysis shows that the title compound has good thermal stability and char forming capability, and its retarding the fire by polyacrylonitrile reveals that the compound is an excellent intumescent fire retardant.

Key words: diethoxythiophosphoryl chloride, p-phenylenediamine, N,N'-di(diethoxythiophosphoryl)-1,4- phenylenediamine, crystal structure, thermal property, intumescent fire retardant