ω-acryltetradecanoic acid | 1519822-35-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ω-acryltetradecanoic acid
• 英文别名: 14-Prop-2-enoyloxytetradecanoic acid；14-prop-2-enoyloxytetradecanoic acid
• CAS: 1519822-35-5
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: GARXGMHNQJPJIC-UHFFFAOYSA-N

物化性质

• 熔点：
  48.9 °C
• 沸点：
  419.6±18.0 °C(predicted)
• 密度：
  0.986±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  14-羟基豆蔻酸 、 丙烯酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以83%的产率得到ω-acryltetradecanoic acid
  参考文献：
  名称：

  Anionic Polymerizable Surfactants from Biobased ω-Hydroxy Fatty Acids

  摘要：

  Biobased omega-hydroxytetradecanoic acid prepared via an efficient yeast-catalyzed omega-hydroxylation reaction was converted by a one-step reaction to the polymerizable surfactants omega-acryltetradecanoic acid (MA-1) and omega-maleate tetradecanoic acid (MA-2). MA-1 is a single polar-headed surfactant, whereas MA-2 is a,bolaamphiphile with carboxylic acid polar groups at both chain ends. MA-1 gave a distinct critical micelle concentration (cmc) at 253 mg/L, whereas for MA-2, the surface tension decreased monotonically and a distinct cmc was not observed even up to 1800 mg/L. Experimental determination of the reactivity ratios for MA-1 and MA-2 with styrene showed that for MA-1 copolymers that approximate random structures were formed while MA-2 tends to form copolymers with an alternating nature. Emulsion polymerizations conducted with varying amounts of MA-1 and MA-2 (1-10 wt % with respect to styrene) gave colloidally stable latexes with particle sizes ranging from 52 to 155 nm. In emulsion polymerizations using either MA-1 or MA-2 at more than 5 wt % to monomer, a linear increase in latex particle volume with conversion was observed and the particle number remained constant, establishing that the polymerizations proceeded without significant aggregation or secondary particle nucleation. Potentiometric titration and H-1 NMR were used to measure MA-1 and MA-2 conversions during polymerization as well as how the surfactants were distributed between the particle surface, aqueous phase, and particle interior. Observed differences were rationalized based on the comparative structures of MA-1 and MA-2 and their corresponding partitioning behavior.

  DOI：

  10.1021/ma401292c

文献信息

• Anionic Polymerizable Surfactants from Biobased ω-Hydroxy Fatty Acids
  作者：Jing Hu、Zhennan Jin、Tzu-Yin Chen、Jennifer D. Polley、Michael F. Cunningham、Richard A. Gross

  DOI：10.1021/ma401292c

  日期：2014.1.14

  Biobased omega-hydroxytetradecanoic acid prepared via an efficient yeast-catalyzed omega-hydroxylation reaction was converted by a one-step reaction to the polymerizable surfactants omega-acryltetradecanoic acid (MA-1) and omega-maleate tetradecanoic acid (MA-2). MA-1 is a single polar-headed surfactant, whereas MA-2 is a,bolaamphiphile with carboxylic acid polar groups at both chain ends. MA-1 gave a distinct critical micelle concentration (cmc) at 253 mg/L, whereas for MA-2, the surface tension decreased monotonically and a distinct cmc was not observed even up to 1800 mg/L. Experimental determination of the reactivity ratios for MA-1 and MA-2 with styrene showed that for MA-1 copolymers that approximate random structures were formed while MA-2 tends to form copolymers with an alternating nature. Emulsion polymerizations conducted with varying amounts of MA-1 and MA-2 (1-10 wt % with respect to styrene) gave colloidally stable latexes with particle sizes ranging from 52 to 155 nm. In emulsion polymerizations using either MA-1 or MA-2 at more than 5 wt % to monomer, a linear increase in latex particle volume with conversion was observed and the particle number remained constant, establishing that the polymerizations proceeded without significant aggregation or secondary particle nucleation. Potentiometric titration and H-1 NMR were used to measure MA-1 and MA-2 conversions during polymerization as well as how the surfactants were distributed between the particle surface, aqueous phase, and particle interior. Observed differences were rationalized based on the comparative structures of MA-1 and MA-2 and their corresponding partitioning behavior.