4-(3'-octyl-1'-imidazolio)-1-butanesulfonic acid bis(trifluoromethylsulfonyl)imidide | 1337883-04-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3'-octyl-1'-imidazolio)-1-butanesulfonic acid bis(trifluoromethylsulfonyl)imidide
• 英文别名: [OBSIm]Tf2N
• CAS: 1337883-04-1
• 化学式: C₂F₆NO₄S₂*C₁₅H₂₉N₂O₃S
• 分子量: 597.622
• InChiKey: OGIIJXCWUKWODN-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  36.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  145.56
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  4-(3-octyl-1-imidazolio)-1-butanesulfonate 、 双三氟甲烷磺酰亚胺 以100%的产率得到4-(3'-octyl-1'-imidazolio)-1-butanesulfonic acid bis(trifluoromethylsulfonyl)imidide
  参考文献：
  名称：

  布朗斯台德酸性离子液体中的聚（氧化烯）合成。

  摘要：

  在布朗斯台德酸性离子液体（BAILs）中研究了具有4-12个亚甲基单元的二醇的聚醚化。在相对较低的温度（130℃）下获得高摩尔质量的聚氧化烯，除了在1,4-丁二醇和1,6-己二醇的情况下观察到形成环醚的情况之外。

  DOI：

  10.1039/c1cc14162g

文献信息

• Influence of Brønsted acid ionic liquid structure on hydroxyacid polyesterification
  作者：Shaodong Zhang、Hervé Lefebvre、Martine Tessier、Alain Fradet

  DOI：10.1039/c1gc15241f

  日期：——

  Brønsted acid ionic liquids (BAILs) based on the 4-(3′-butyl-1′-imidazolio)-1-butanesulfonic acid cation were found to be very efficient polyesterification solvents and catalysts. Only 5–30 min at 90–110 °C was required to obtain high molar mass poly(12-hydroxydodecanoic acid) (Mw up to 40000 g mol−1). The polyesterification was faster in BAILs with the bis(trifluoromethylsulfonyl)imidide anion (Tf2N), but small amounts of ethers and double bonds arising from side reactions were detected in the final polymer. On the other hand, no side reactions took place in the BAIL with the hydrogen sulfate anion, except for the formation of a sulfonate ester intermediate that can further react with carboxylic acid groups to yield the expected ester. This intermediate, not observed in Tf2N-based BAILs, might be involved in the protection of hydroxy end groups from etherification side reactions in HSO4−-based BAILs. To explain the different behaviors of these BAILs, and since the acidity of H2SO4 is much higher than that of Tf2NH, it is suggested that the structure of these BAILs could be different: alkylsulfonic acid-substituted imidazolium for the former, while the latter could be just a mixture of imidazolium–sulfonate zwitterion and Tf2NH. The influence of reaction temperature, water elimination method and BAIL concentration on polyesterification are also discussed.

  基于4-(3′-丁基-1′-咪唑鎓)-1-丁磺酸阳离子的Brønsted酸离子液体（BAILs）被发现是非常高效的不饱和聚酯溶剂和催化剂。仅在90–110 °C下5–30分钟就可以获得高摩尔质量的聚（12-羟基十二酸）（Mw高达40000 g mol−1）。在不饱和聚酯中含有双（三氟甲磺酰）亚胺阴离子（Tf2N）的BAILs中，不饱和聚酯化反应速度更快，但在最终聚合物中检测到少量由副反应产生的醚和双键。另一方面，在含有硫酸氢阴离子的BAILs中，除了形成磺酸酯中间体并进一步与羧酸基团反应生成预期的酯之外，没有发生副反应。这种中间体在基于Tf2N的BAILs中未被观察到，可能参与了保护羟基端基在基于硫酸氢的BAILs中免受醚化副反应的影响。为了解释这些BAILs的不同行为，并且由于H2SO4的酸性远高于Tf2NH，因此提出这些BAILs的结构可能不同：前者是烷基磺酸取代的咪唑鎓，而后者可能只是咪唑鎓-磺酸盐两性离子和Tf2NH的混合物。还讨论了反应温度、水的消除方法和BAIL浓度对不饱和聚酯化的影响。