3-[(5-hydroxymethyl)-2-furanyl]-2-methylacrolein | 1265913-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-[(5-hydroxymethyl)-2-furanyl]-2-methylacrolein
• 英文别名: 3-[5-(hydroxymethyl)furan-2-yl]-2-methylprop-2-enal
• CAS: 1265913-77-6
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: LIWXAUACKZIAGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.44
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-羟甲基糠醛 、 丙醛 在 MgO-ZrO₂ catalyst 作用下， 以 甲醇 、 水 为溶剂， 120.0 ℃ 、5.27 MPa 条件下， 生成 3-[(5-hydroxymethyl)-2-furanyl]-2-methylacrolein 、 5-[5-(hydroxymethyl)-2-furyl]-2,4-dimethyl-2,4-pentadienal
  参考文献：
  名称：

  Liquid phase aldol condensation reactions with MgO–ZrO2 and shape-selective nitrogen-substituted NaY

  摘要：

  The aldol condensation reactions of furfural/hydroxymethylfurfural (furfurals) with acetone/propanal in water-methanol solvents were studied over the solid base catalysts MgO-ZrO2, NaY and nitrogen-substituted NaY (Nit-Nay). The reactions were conducted at 120 degrees C and 750 psig of He in batch reactors. Nit-NaY exhibited catalytic activity for aldol condensation comparable to MgO-ZrO2 and much higher than that of NaY, indicative of the increased base strength after replacing the bridging oxygen with the lower electronegativity nitrogen over Nit-NaY. The aldol condensation of furfurals with acetone produces two different products, the monomer and the dimer. The monomer is formed from reaction of furfurals with acetone. The dimer is formed from reaction of the monomer with furfurals. MgO-ZrO2 had a higher selectivity towards dimer formation. In contrast, Nit-NaY was more selective towards the monomer product due to the cage size in the FAU structure, indicating that Nit-Nay is a shape selective base catalyst. Increasing the water concentration in the feed solution or increasing the feed concentration led to both increased catalytic activity and dimer selectivity. The Nit-NaY catalyst was not stable and lost catalytic activity when recycled due to leaching of the framework nitrogen. Different characterization techniques, including XRD, high resolution Ar adsorption isotherm, basic sites titration, CO2 TPD-MS, TGA and Si-29 SP MAS NMR, were used here to characterize the fresh and spent catalysts. The results show that Nit-NaY maintains only part of the FAU-type crystal structure. Furthermore, the base strength over Nit-NaY was found to be between that of Mg2+-O2- pair and Mg(OH)(2). The reaction mechanism over Nit-NaY was discussed. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2010.10.023