4-methyl-1-(1-oxo-10-undecylenyl)piperidine | 876895-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 4-methyl-1-(1-oxo-10-undecylenyl)piperidine
• 英文别名: 1-(4-Methylpiperidin-1-yl)undec-10-en-1-one
• CAS: 876895-85-1
• 化学式: C₁₇H₃₁NO
• 分子量: 265.439
• InChiKey: ZDKGRZKENCJUAC-UHFFFAOYSA-N

物化性质

• 沸点：
  392.9±21.0 °C(Predicted)
• 密度：
  0.907±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-甲基哌啶 、 月桂酸 在 硼酸 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 4-methyl-1-(1-oxo-10-undecylenyl)piperidine
  参考文献：
  名称：

  Intensified Azeotropic Distillation: A Strategy for Optimizing Direct Amidation

  摘要：

  The direct synthesis of amides from the corresponding carboxylic acids and amines is shown to operate under varying degrees of mixed kinetic and mass transfer rate control when water is removed by azeotropic distillation. Unless the volumetric heat input rate is reported, it is not possible to make a valid comparison between different catalysts, as the difference in Q(boil) alone can be responsible for the apparent difference in observed rate. A systematic approach is developed to quantify the contribution of boil-up rate to conversion rate and so decouple the physical rates from the chemistry. Intensive boiling is used to improve the removal of water during azeotropic distillation and considerably enhance conversion. The results show that some acylations previously thought to be difficult or impossible can be achieved in the absence of coupling agents under green conditions. The use of a cascade of CSTR flow reactors operating under intensified conditions is assessed for scale up of direct amidation reactions and compared to a production scale batch reactor. The findings and conclusions of this work have general applicability to all condensation reactions.

  DOI：

  10.1021/op300058f

文献信息

• Intensified Azeotropic Distillation: A Strategy for Optimizing Direct Amidation
  作者：Christophe Grosjean、Julie Parker、Carl Thirsk、Allen R. Wright

  DOI：10.1021/op300058f

  日期：2012.5.18

  The direct synthesis of amides from the corresponding carboxylic acids and amines is shown to operate under varying degrees of mixed kinetic and mass transfer rate control when water is removed by azeotropic distillation. Unless the volumetric heat input rate is reported, it is not possible to make a valid comparison between different catalysts, as the difference in Q(boil) alone can be responsible for the apparent difference in observed rate. A systematic approach is developed to quantify the contribution of boil-up rate to conversion rate and so decouple the physical rates from the chemistry. Intensive boiling is used to improve the removal of water during azeotropic distillation and considerably enhance conversion. The results show that some acylations previously thought to be difficult or impossible can be achieved in the absence of coupling agents under green conditions. The use of a cascade of CSTR flow reactors operating under intensified conditions is assessed for scale up of direct amidation reactions and compared to a production scale batch reactor. The findings and conclusions of this work have general applicability to all condensation reactions.