morpholinium formate | 83420-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: morpholinium formate
• 英文别名: [morph][F]；morpholin-4-ium;formate
• CAS: 83420-64-8
• 化学式: CH₂O₂*C₄H₉NO
• 分子量: 133.147
• InChiKey: BDHPJXPOQGPUNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.69
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decanal 、 morpholinium formate 、 盐酸 生成 2,3-Dimethoxy-5-methyl-6-(10-morpholin-4-yldecyl)cyclohexa-2,5-diene-1,4-dione;hydrochloride
  参考文献：
  名称：

  TERAO, SHINJI;OKAZAKI, HISAYOSHI;IMADA, ISUKE

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉 、 甲酸 反应 24.75h， 生成 morpholinium formate
  参考文献：
  名称：

  基于羧酸盐的室温离子液体作为钯催化均偶联和芳基卤化物的 Sonogashira-Hagihara 反应的有效介质

  摘要：

  羧酸盐是一种易于制备、廉价且稳定的离子液体 (IL)，可作为碱、配体、还原剂和介质，用于无磷烷、钯催化的芳基碘化物和溴化物的均偶联反应。在这些离子液体中也证明了芳基碘化物和溴化物的高效无铜和磷烷 Sonagashira 偶联反应。其中一种 ILs 也被磷酸化并显示出作为介质的高效率和可回收性，并且还用作钯催化的芳基碘化物和溴化物的均偶联和无铜 Sonogashira 反应的配体。

  DOI：

  10.1002/ejoc.201100701
• 作为试剂：
  描述：

  对氯甲苯 在 morpholinium formate 、 palladium dichloride 作用下， 反应 12.0h， 以45%的产率得到4,4'-二甲基联苯
  参考文献：
  名称：

  基于羧酸盐的室温离子液体作为钯催化均偶联和芳基卤化物的 Sonogashira-Hagihara 反应的有效介质

  摘要：

  羧酸盐是一种易于制备、廉价且稳定的离子液体 (IL)，可作为碱、配体、还原剂和介质，用于无磷烷、钯催化的芳基碘化物和溴化物的均偶联反应。在这些离子液体中也证明了芳基碘化物和溴化物的高效无铜和磷烷 Sonagashira 偶联反应。其中一种 ILs 也被磷酸化并显示出作为介质的高效率和可回收性，并且还用作钯催化的芳基碘化物和溴化物的均偶联和无铜 Sonogashira 反应的配体。

  DOI：

  10.1002/ejoc.201100701

文献信息

• An integrated process of CO₂capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system
  作者：Yu-Nong Li、Liang-Nian He、Xian-Dong Lang、Xiao-Fang Liu、Shuai Zhang

  DOI：10.1039/c4ra08740b

  日期：——

  An integrated process of CO2 capture and in situ hydrogenation into formate was achieved in 95–99% yield using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system, being regarded as an alternative carbon capture and utilization approach to supply fuel-related products, to circumvent the energy penalty in carbon capture and storage. CO2 was captured by non-volatile amidine derivatives with simultaneous activation to form zwitterionic amidinium carbonate, and subsequent hydrogenation was facilitated by Rh/bisphosphine. The adsorption capacity and hydrogenation efficiency can be optimized by tuning the ethoxyl side chain. Particularly, the alkanolamidine bearing an intramolecular hydrogen donor derived from 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU) gave both a high CO2 uptake (molar ratio of 0.95 : 1) and excellent hydrogenation yield (99%). Furthermore, the silica-supported alkanolamidine was readily recovered and reused with the retention of good performance. This kind of carbon capture and utilization pathway could be a potential energy-saving option for industrial upgrading of CO2 from waste to fuel-related products in a carbon neutral manner.

  实现了CO2捕集与原位氢化为甲酸的综合过程，产率达到95%-99%，使用了可调的乙氧基功能化胺基及Rh/双磷酸酯体系，这被视为供应燃料相关产品的替代碳捕集与利用方法，以避免碳捕集与储存中的能量损失。CO2通过非挥发性胺基衍生物被捕集，同时活化形成带有双重电荷的胺基碳酸盐，随后氢化过程由Rh/双磷酸酯促进。通过调节乙氧基侧链，可以优化吸附能力和氢化效率。特别是，具有来源于1,8-二氮双环[5.4.0]-十一烯（DBU）内源氢供体的烷醇胺基显示出高CO2吸附量（摩尔比为0.95:1）和优异的氢化产率（99%）。此外，硅胶支持的烷醇胺基可以方便地回收再利用，并保持良好性能。这种碳捕集与利用路径可能成为将废弃CO2工业转化为燃料相关产品的潜在节能选择，以实现碳中和。
• Physicochemical Characterization of Morpholinium Cation Based Protic Ionic Liquids Used As Electrolytes
  作者：Catherine Brigouleix、Mérièm Anouti、Johan Jacquemin、Magali Caillon-Caravanier、Hervé Galiano、Daniel Lemordant

  DOI：10.1021/jp906917v

  日期：2010.2.11

  New protic ionic liquids (PILs) based on the morpholinium, N-methylmorpholinium, and N-ethyl morpholinium cations have been synthesized through a simple and atom-economic neutralization reaction between N-alkyl morpholine and formic acid. Their densities, refractive indices, thermal properties, and electrochemical windows have been measured. The temperature dependence of their dynamic viscosity and ionic conductivity have also been determined. The results allow us to classify them according to a classical Walden diagram and to evaluate their "fragility". In addition, morpholinium based PILs exhibit a large electrochemical window as compared to other protic ionic liquids (up 2.91 V) and possess relatively high ionic conductivities of 10-16.8 mS.cm(-1) at 25 degrees C and 21-29 mS.cm(-1) at 100 degrees C, and a residual conductivity close to 1.0 mS.cm(-1) at - 15 degrees C. PIL-water Mixtures exhibit high ionic conductivities up to 65 mS.cm(-1) at 25 degrees C and 120 mS.cm(-1) at 100 degrees C for morpholinium formate with water weight fraction w(w) = 0.6. Morpholinium based PILs studied in this work have a low cost and low toxicity, are good ionic liquids, and prove extremely fragile. They have wide applicable perspectives as electrolytes for fuel cell devices, thermal transfer fluids, and acid-catalyzed reaction media as replacements of conventional solvents.
• TERAO, SHINJI;OKAZAKI, HISAYOSHI;IMADA, ISUKE
  作者：TERAO, SHINJI、OKAZAKI, HISAYOSHI、IMADA, ISUKE

  DOI：——

  日期：——
• Carboxylate-Based, Room-Temperature Ionic Liquids as Efficient Media for Palladium-Catalyzed Homocoupling and Sonogashira-Hagihara Reactions of Aryl Halides
  作者：Nasser Iranpoor、Habib Firouzabadi、Yasaman Ahmadi

  DOI：10.1002/ejoc.201100701

  日期：2012.1

  phosphane-free, palladium-catalyzed homocoupling reaction of aryl iodides and bromides. The efficient copper and phosphane-free Sonagashira coupling reaction of aryl iodides and bromides is also demonstrated in these ILs. One of the ILs was also phosphorylated and showed high efficiency and recyclability as a medium, and was also used as a ligand for palladium-catalyzed homocoupling and copper-free Sonogashira

  羧酸盐是一种易于制备、廉价且稳定的离子液体 (IL)，可作为碱、配体、还原剂和介质，用于无磷烷、钯催化的芳基碘化物和溴化物的均偶联反应。在这些离子液体中也证明了芳基碘化物和溴化物的高效无铜和磷烷 Sonagashira 偶联反应。其中一种 ILs 也被磷酸化并显示出作为介质的高效率和可回收性，并且还用作钯催化的芳基碘化物和溴化物的均偶联和无铜 Sonogashira 反应的配体。