cis-2,3-Difluoroacrylsaeure | 71170-74-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: cis-2,3-Difluoroacrylsaeure
• 英文别名: (Z)-α,β-difluoroacrylic acid；DiFAA；Difluoroacrylic acid；(Z)-2,3-difluoroprop-2-enoic acid
• CAS: 71170-74-6
• 化学式: C₃H₂F₂O₂
• 分子量: 108.044
• InChiKey: LLCKXLBGFBTDHO-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3,3-trichloro-2,3-difluoro-propionic acid 生成 cis-2,3-Difluoroacrylsaeure
  参考文献：
  名称：

  DAPPERHELD, STEFFEN;HEUMULLER, RUDOLF;WILDT, MANFRED

  摘要：

  DOI：

文献信息

• Sauvetre,R. et al., Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1979, vol. 288, p. 335 - 338
  作者：Sauvetre,R. et al.

  DOI：——

  日期：——
• Radical Copolymerization of α,β-Difluoroacrylic Acid with Vinylidene Fluoride.
  作者：Frédéric Boschet、Jean-Marc Cracowski、Véronique Montembault、Bruno Ameduri

  DOI：10.1021/ma100506e

  日期：2010.6.8

  The synthesis of alpha,beta-difluoroacrylic acid (FHC=CF-CO2H, DiFAA) and its radical copolymerization with vinylidene fluoride (CH2=CF2, VDF) are presented. First, DiFAA was synthesized in three steps from the radical addition of methanol onto 1,2-dichloro-1,2-difluoroethylene leading to HCFCICFCICH2OH in 78% yield. Then, oxidation of the hydroxymethyl end-group followed by zinc-mediated dehalogenation of 2,3-dichloro-2,3-difluoropropanoic acid led to (Z) isomer of DiFAA in 29% overall yield. The homopolymerization of DiFAA was successfully achieved by radical polymerization initiated by tert-butylperoxypivalate (TBPPi) at 74 degrees C in 32% yield. Its radical copolymerization with VDF was carried out for the first time and at various compositions leading to functional poly(VDF). The resulting poly(VDF-co-DiFAA) copolymers, characterized by H-1 and F-19 NMR spectroscopies, exhibited a statistic microstructure. The kinetics of this radical copolymerization led to the assessment of the reactivity ratios (r(DiFAA) = 0.86 and r(VDF) = 0.34 at 74 degrees C), and showed that DiFAA was more reactive than VDF in copolymerization. Thermal properties of these poly(DiFAA-co-VDF) copolymers were also investigated. Differential scanning calorimetry analyses showed a decrease of the glass transition temperature (T-g) with increasing VDF content. Calculations using the Fox's equation led to the determination of the T-g for poly(DiFAA) homopolymer (T-g = 145 degrees C) in good agreement with the literature. Thermogravimetric analyses displayed increased thermostability of the resulting copolymers with increasing VDF content.
• DAPPERHELD, STEFFEN;HEUMULLER, RUDOLF;WILDT, MANFRED
  作者：DAPPERHELD, STEFFEN、HEUMULLER, RUDOLF、WILDT, MANFRED

  DOI：——

  日期：——