5-hydroxymethyl-2-furfuraldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-hydroxymethyl-2-furfuraldehyde
• 英文别名: 5-(hydroxymethyl)furan-2-carbaldehyde；4-(Hydroxymethyl)cyclopenta-1,3-diene-1-carbaldehyde
• 化学式: C₇H₈O₂
• 分子量: 124.139
• InChiKey: FKXOTXVEFLOOET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-hydroxymethyl-2-furfuraldehyde 在 对甲苯磺酸 作用下， 以 水 为溶剂， 生成 乙酰丙酸
  参考文献：
  名称：

  一种一锅法制备乙酰丙酸和磺化碳催化剂的 方法

  摘要：

  本发明提出了一种一锅法制备乙酰丙酸和磺化碳催化剂的方法，将质量相等的葡萄糖和对甲苯磺酸混合均匀放入反应罐中，加入水，密闭反应器反应，反应后冷却至室温，得到固液混合产物；对固液混合产物进行水洗、抽滤分离，得到液相产物和固相产物；液相产物主要为乙酰丙酸和对甲苯磺酸；固相产物为磺化碳催化剂。采用一锅法，在利用葡萄糖生成乙酰丙酸的同时生成磺化碳催化剂（而不是胡敏素），极大的提高了葡萄糖的碳利用效率，工艺流程简单、操作方便、产率高。

  公开号：

  CN106349045B
• 作为产物：
  描述：

  D-fructose 在 氯化(1-丁基-3-甲基咪唑) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以55%的产率得到5-hydroxymethyl-2-furfuraldehyde
  参考文献：
  名称：

  Role of N-heterocyclic carbenes in glucose conversion into HMF by Cr catalysts in ionic liquids

  摘要：

  As N-heterocyclic carbenes (NHCs) can be readily formed from deprotonation of their precursors-imidazolium salts (i.e., ionic liquids, ILs) that are typically used as solvent in homogenous glucose-to-5-hydroxymethylfurfural (HMF) conversion systems with CrClx (x = 2 or 3) as catalyst-the hypothesis that the (NHC)-CrClx complex is the true catalyst for such conversion exists in the literature, but it has not been tested. Reported herein are three sets of mechanistic probes to address the role of the NHC ligand in the glucose-to-HMF conversion by CrClx in ILs. Specifically, controls with all additives (reagents) involved in the conversion system, performances of in situ generated NHC ligands or Cr complexes as well as discrete NHC ligands and Cr complexes that were proposed to be the true catalyst, and quantitative NHC titration (poisoning) experiments conclusively show that the NHC ligand actually serves as a poison to the chromium catalyst system and that a superstoichiometric amount (2 or 3 equiv.) of the NHC ligand can completely shut down the catalysis. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2013.04.015

文献信息

• PROCESS FOR PURIFYING CRUDE FURAN 2,5-DICARBOXYLIC ACID USING HYDROGENATION
  申请人：Eastman Chemical Company

  公开号：EP3333160A1

  公开（公告）日：2018-06-13

  A process to produce a dry purified furan-2,5-dicarboxylic acid (FDCA) is described. After oxidation of 5-(hydroxymethyl)furfural (5-HMF), a crude FDCA stream is produced that is fed to a crystallization zone followed by a solid-liquid displacement zone to form a low impurity slurry stream. The solids in the low impurity slurry stream are dissolved in a dissolution zone to produce a hydrogenation feed that is hydrogenated in a hydrogenation reactor to generate a hydrogenated FDCA composition. The hydrogenated FDCA composition is routed to a crystallization zone to form a crystallized produce stream that is separated from liquid in a solid-liquid separation zone to generate a purified wet cake stream containing FDCA that can be dried in a drying zone to generate a dry purified FDCA product stream.

  描述了一种生产干法纯化呋喃-2,5-二羧酸（FDCA）的工艺。5-(hydroxymethyl)furfural (5-HMF) 氧化后，产生粗 FDCA 流，将其送入结晶区，然后进入固液置换区，形成低杂质浆液流。低杂质浆液流中的固体在溶解区溶解，生成氢化进料，在氢化反应器中氢化，生成氢化 FDCA 组合物。氢化后的 FDCA 组合物进入结晶区，形成结晶产品流，在固液分离区与液体分离，生成含有 FDCA 的净化湿饼流，在干燥区进行干燥，生成干燥的净化 FDCA 产品流。
• One-step hydrothermal fabrication of visible-light-responsive pompon-like SnxInyS2x+1.5y heterojunctions for highly-efficient photocatalytic oxidation of 5-hydroxymethylfurfural without additional oxidants
  作者：Shufen Yu、Chunhui Song、Haowei Zhang、Weiping Liao、Deyang Zhao、Christophe Len、Hongying Lü、Ting Su

  DOI：10.1016/j.jallcom.2024.173810

  日期：2024.4

  catalysts with hierarchical pompon-like architectures were fabricated by a one-step hydrothermal method for efficiently visible-light-driven dehydrogenation of 5-hydroxymethylfurfural (HMF) into 2,5-diformylfuran (DFF) with high selectivity. Particularly, the hydrothermal synthesis conferred those SnInS catalysts with Sn:In ratios over 1:4.5 with a three-dimensional heterojunction structure composed of InS

  采用一步水热法制备了具有分级绒球状结构的 SnInS 双金属硫化物催化剂，可在可见光驱动下高效地将 5-羟​​甲基糠醛 (HMF) 脱氢成高选择性的 2,5-二甲酰呋喃 (DFF)。特别是，水热合成使Sn:In比例超过1:4.5的SnInS催化剂具有由InS和四方相SnInS组成的三维异质结结构、适当的比面积以及增强的光吸收能力。SnInS表现出优越的性能，在不需要任何氧化剂的情况下，选择性约为90%，DFF的收率达到62%。此外，超氧化物（•O）和羟基自由基（•OH）是主要的反应物种，而InS和SnInS组成的异质结结构有效抑制了光生载流子的复合，从而获得了优异的性能。这项工作描绘了构建新型低成本光催化系统的有效策略，为 HMF 的价值化铺平了新的道路。
• Efficient Synthesis of 8-Oxa-3-aza-bicyclo[3.2.1]octane Hydrochloride
  作者：Terrence J. Connolly、John L. Considine、Zhixian Ding、Brian Forsatz、Mellard N. Jennings、Michael F. MacEwan、Kevin M. McCoy、David W. Place、Archana Sharma、Karen Sutherland

  DOI：10.1021/op9002642

  日期：2010.3.19

  A four-step process to generate 8-oxa-3-aza-bicyclo[3.2.1]octane hydrochloride starting with 5-hydroxymethyl-2-furfuraldehyde is described. Raney nickel-mediated reduction of 5-hydroxymethyl-2-furfuraldehyde afforded 2,5-bis(hydroxymethyl)tetrahydrofuran with a predominantly cis configuration. Conversion of the diol to a ditosylate, followed by cyclization with benzylamine generated the 8-oxa-3-aza-bicyclo[3.2.1]octane core. The title compound was prepared via hydrogenolysis of the N-benzyl group with Pearlman's catalyst and isolated as the hydrochloride salt front it mixture of 2-propanol and heptane. The overall yield for the process was 43-64%. An impurity generated during scale tip highlighted the need for a strict in-process specification for acetonitrile content prior to performing the final hydrogenolysis. Ethanol conditioning of all processing equipment that had acetonitrile contact prior to the introduction of the substrate stock solution is highly recommended.
• 一种一锅法制备乙酰丙酸和磺化碳催化剂的 方法
  申请人：东莞理工学院

  公开号：CN106349045B

  公开（公告）日：2018-06-29

  本发明提出了一种一锅法制备乙酰丙酸和磺化碳催化剂的方法，将质量相等的葡萄糖和对甲苯磺酸混合均匀放入反应罐中，加入水，密闭反应器反应，反应后冷却至室温，得到固液混合产物；对固液混合产物进行水洗、抽滤分离，得到液相产物和固相产物；液相产物主要为乙酰丙酸和对甲苯磺酸；固相产物为磺化碳催化剂。采用一锅法，在利用葡萄糖生成乙酰丙酸的同时生成磺化碳催化剂（而不是胡敏素），极大的提高了葡萄糖的碳利用效率，工艺流程简单、操作方便、产率高。
• Role of N-heterocyclic carbenes in glucose conversion into HMF by Cr catalysts in ionic liquids
  作者：Eric F. Dunn、Dajiang (D.J.) Liu、Eugene Y.-X. Chen

  DOI：10.1016/j.apcata.2013.04.015

  日期：2013.6

  As N-heterocyclic carbenes (NHCs) can be readily formed from deprotonation of their precursors-imidazolium salts (i.e., ionic liquids, ILs) that are typically used as solvent in homogenous glucose-to-5-hydroxymethylfurfural (HMF) conversion systems with CrClx (x = 2 or 3) as catalyst-the hypothesis that the (NHC)-CrClx complex is the true catalyst for such conversion exists in the literature, but it has not been tested. Reported herein are three sets of mechanistic probes to address the role of the NHC ligand in the glucose-to-HMF conversion by CrClx in ILs. Specifically, controls with all additives (reagents) involved in the conversion system, performances of in situ generated NHC ligands or Cr complexes as well as discrete NHC ligands and Cr complexes that were proposed to be the true catalyst, and quantitative NHC titration (poisoning) experiments conclusively show that the NHC ligand actually serves as a poison to the chromium catalyst system and that a superstoichiometric amount (2 or 3 equiv.) of the NHC ligand can completely shut down the catalysis. (c) 2013 Elsevier B.V. All rights reserved.