2-hydroxyethyl methyl carbonate | 106729-72-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 2-hydroxyethyl methyl carbonate
• 英文别名: HEMC；Hydroxyethyl methyl carbonate
• CAS: 106729-72-0
• 化学式: C₄H₈O₄
• 分子量: 120.105
• InChiKey: JJRXNONHGBNFSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl methyl carbonate 、 六甲基二硅氮烷 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 以44%的产率得到methyl [2-(trimethylsiloxy)ethyl] carbonate
  参考文献：
  名称：

  Structure-property relationship and transport properties of structurally related silyl carbonate electrolytes

  摘要：

  Ten different substituted structurally related linear and cyclic carbonates were synthesized and investigated as electrolyte solvents for lithium-ion cells. Synthesis of the compounds, mainly silyl carbonates, was carried out via catalytic CO2 addition, nucleophilic substitution or hydrosilylation. Besides the ten synthesized compounds a binary mixture of a cyclic and linear silyl carbonate, propylene carbonate (PC), diethyl carbonate (DEC) and a binary mixture thereof were analyzed as a function of molar lithium ((bistrifluoromethyl) sulfonyl) imide LiTFSI ratio in order to develop a structure-property relationship. The extrapolation of the temperature-dependent ionic conductivities using Vogel-Tamman-Fulcher (VTF) equation revealed a solvent assisted ionic transport mechanism. The strength of interaction between the lithium-ion and the respective carbonates was investigated via C-13 and Si-29 NMR measurements by the change of the chemical shift upon LiTFSI addition. The results show that the interaction of the lithium ion with the cyclic carbonates is much stronger compared to the linear ones and varies among the different substituents. These findings were in good accordance with ionicities represented by the Walden product. The diffusivities of Li+ and TFSI were determined via Pulsed Field Gradient STimulated Echo (PGSTE)-NMR. The hydrodynamic radii calculated thereof demonstrate the superior coordination ability of the cyclic carbonates as compared to linear structures. Furthermore, Haven ratios indicate rather different dissociation abilities of different carbonate solvents, depending on the structural fragment of the solvents. (C)2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2015.05.108
• 作为产物：
  描述：

  methyl 2-[(phenylmethyl)oxy]ethyl carbonate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以300 mg的产率得到2-hydroxyethyl methyl carbonate
  参考文献：
  名称：

  达比加群酯衍生物及其药学用途

  摘要：

  本发明公开了一种如式(II)所示的化合物，其水合物、异构体、溶剂化物、前药或它们的混合物，以及它们药学上可接受的盐；本发明还公开了含有这些化合物作为活性成分的药物组合物与联合制剂；以及所述化合物、药物组合物和联合制剂作为凝血酶抑制剂的用途。

  公开号：

  CN109897028B

文献信息

• NaZSM-5-catalyzed dimethyl carbonate synthesis via the transesterification of ethylene carbonate with methanol
  作者：Zhen-Zhen Yang、Xiao-Yong Dou、Fang Wu、Liang-Nian He

  DOI：10.1139/v11-031

  日期：2011.5

  NaZSM-5 zeolite was found to be an efficient heterogeneous catalyst for the synthesis of dimethyl carbonate (DMC), which can serve as a building block, an additive to fuel oil, and an electrolyte in batteries, via the transesterification of ethylene carbonate (EC) with methanol. Notably, 77% DMC yield and 97% selectivity were achieved under mild reaction conditions. Furthermore, the effects of various reaction parameters such as catalyst loading, reaction time, and methanol/EC molar ratio on the catalytic performance were investigated in detail. This protocol was found to be applicable to a variety of alcohols, producing the corresponding dialkyl carbonates with moderate yields and selectivities. Moreover, the catalyst can be recovered by simple filtration with retention of catalytic activity; a stable crystal configuration and a slight alteration of its superficial structure were observed by X-ray diffraction and BET measurements.

  NaZSM-5沸石被发现是一种高效的杂相催化剂，可用于合成碳酸二甲酯（DMC），DMC可用作建筑块、燃料油添加剂和电池电解质，通过乙烯碳酸酯（EC）与甲醇的酯交换反应。值得注意的是，在温和的反应条件下，实现了77%的DMC产率和97%的选择性。此外，详细研究了各种反应参数（如催化剂负载量、反应时间和甲醇/EC摩尔比）对催化性能的影响。发现该方案适用于各种醇类，产生相应的二烷基碳酸酯，产率和选择性适中。此外，通过简单的过滤可以回收催化剂，并保持催化活性；通过X射线衍射和BET测量观察到了稳定的晶体结构和表面结构的轻微改变。
• Process for co-production of dialkyl carbonate and alkanediol
  申请人：ExxonMobil Chemical Patents Inc.

  公开号：US06342623B1

  公开（公告）日：2002-01-29

  A method is provided for co-producing dialkyl carbonate and alkanediol by reacting alkylene carbonate with alkanol in the presence of an amorphous aluminosilicate catalyst containing alkali metal, alkaline earth metal, or a combination thereof.

  提供了一种方法，通过在存在含有碱金属、碱土金属或二者组合的非晶态氧化铝硅酸盐催化剂的情况下，将烷基碳酸酯与烷醇反应来共同生产二烷基碳酸酯和烷二醇。
• PROCESS FOR PREPARING CARBONATE AND DIOL PRODUCTS
  申请人：Zhang Xiankuan

  公开号：US20130225840A1

  公开（公告）日：2013-08-29

  A method of forming a cyclic carbonate product is carried out by reacting an alkylene oxide, such as ethylene oxide, with carbon dioxide in the presence of a metal organic framework (MOF) catalyst with less than 0.5 mol % of any potassium or quaternary ammonium salts present based on moles of alkylene oxide feed in a reaction zone under reaction conditions to form a cyclic carbonate product. The cyclic carbonate product may be optionally fed as a crude carbonate product that does not undergo any purification or separation, other than the optional removal of any portion of unreacted alkylene oxide, carbon dioxide, and light hydrocarbon gases, to a second reaction zone containing a transesterification catalyst along with an aliphatic monohydric alcohol. The cyclic carbonate product and monohydric alcohol are allowed to react under reaction conditions to form the dialkyl carbonate and diol products.

  一种形成环状碳酸酯产品的方法是在反应区域中，在反应条件下，通过将烷基氧化物（如环氧乙烷）与二氧化碳在存在金属有机框架（MOF）催化剂的情况下反应，基于烷基氧化物进料的摩尔数，存在少于0.5摩尔％的任何钾盐或季铵盐，形成环状碳酸酯产品。环状碳酸酯产品可以选择性地作为未经任何纯化或分离的粗碳酸酯产品进料，除了可选择地去除任何未反应的烷基氧化物、二氧化碳和轻烃气体的部分，进入含有酯交换催化剂和脂肪族一元醇的第二反应区域。环状碳酸酯产品和一元醇在反应条件下允许反应，形成二烷基碳酸酯和二醇产品。
• Carbonate phosphonium salts as catalysts for the transesterification of dialkyl carbonates with diols. The competition between cyclic carbonates and linear dicarbonate products
  作者：Maurizio Selva、Alessio Caretto、Marco Noè、Alvise Perosa

  DOI：10.1039/c4ob00655k

  日期：——

  At 90–120 °C, in the presence of methylcarbonate and bicarbonate methyltrioctylphosphonium salts as catalysts ([P8881][A]; [A] = MeOCO2 and HOCO2), the transesterification of non-toxic dimethyl- and diethyl-carbonate (DMC and DEC, respectively) with 1,X-diols (2 ≤ X ≤ 6) proceeds towards the formation of cyclic and linear products. In particular, 1,2-propanediol and ethylene glycol afford propylene-

  在90–120°C下，在存在碳酸甲酯和碳酸氢盐的情况下，甲基三辛基phosph盐作为催化剂（[P 8881 ] [A]； [A] = MeOCO 2和HOCO 2），无毒碳酸二甲酯和碳酸二乙酯进行酯交换反应用1（DMC和DEC，分别地），X -diols（2≤ X ≤6）朝向环状和线性产物的形成进行。特别地，1,2-丙二醇和乙二醇选择性地提供碳酸亚丙酯和碳酸亚乙酯，产率分别高达95％和90％。同时，DMC与高级二醇反应，例如1,3-丁二醇，2-甲基-1,3-丙二醇，1,3-丙二醇，2,2-二甲基，1,3-丙二醇，1,4-丁二醇和1,6-己二醇产生线性C 8 –C10种通式为MeOC（O）O ~~~ OC（O）OMe的二碳酸酯几乎是排他的产物。值得注意的是，这些二碳酸酯衍生物否则不能通过其他常规的碱催化方法以高收率获得。在1，3-二醇中，唯一的例外是2-甲基2，4-戊二醇产生相应的环状碳酸酯
• Protic ionic liquid-promoted synthesis of dimethyl carbonate from ethylene carbonate and methanol
  作者：Yu Song、Xing He、Bing Yu、Hong-Ru Li、Liang-Nian He

  DOI：10.1016/j.cclet.2019.07.053

  日期：2020.3

  the protic ionic liquid [DBUH][Im] (1,8-diazabicyclo[5.4.0]-7-undeceniumimidazolide) was developed as an efficient catalyst for the transesterification of ethylene carbonate with methanol to produce dimethyl carbonate. At 70 °C, up to 97% conversion of ethylene carbonate and 91% yield of dimethyl carbonate were obtained with 1 mol% [DBUH][Im] (relative to ethylene carbonate) as catalyst in 2 h. Even at

  摘要在这项工作中，质子离子液体[DBUH] [Im]（1,8-二氮杂双环[5.4.0] -7-十一碳铝咪唑化物）被开发为一种有效的催化剂，用于碳酸亚乙酯与甲醇的酯交换反应以生产碳酸二甲酯。在70°C下，用1 mol％[DBUH] [Im]（相对于碳酸亚乙酯）作为催化剂，在2小时内可获得高达97％的碳酸亚乙酯转化率和91％的碳酸二甲酯产率。即使在室温下，碳酸亚乙酯的转化率也可以达到94％，碳酸二甲酯的产率在6小时内可以达到81％。催化机理研究表明，这种离子液体的高催化效率是由协同活化作用引起的，其中阳离子可以活化碳酸亚乙酯，而阴离子可以通过氢键形成来活化甲醇。