碳酸乙叉酯

碳酸乙叉酯
	IUPAC名; 1,3-dioxolan-2-one
别名	ethylene glycol carbonate
识别
CAS号	96-49-1
PubChem	7303
ChemSpider	7030
SMILES	C1COC(=O)O1;
InChI	1/C3H4O3/c4-3-5-1-2-6-3/h1-2H2;
InChIKey	KMTRUDSVKNLOMY-UHFFFAOYAD
性质
化学式	C3H4O3
摩尔质量	88.06 g·mol−1
外观	色调白至黄的固体
密度	1.3210 g/cm3
熔点	34—37 °C（307—310 K）
沸点	243.0 °C（516 K）
溶解性（水）	可溶
危险性
警示术语	R：R41
安全术语	S：S26 S39
欧盟分类	具刺激性 (XI)
闪点	150℃
自燃温度	465℃
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

碳酸乙烯酯（英语：Ethylene carbonate，缩写EC）是结构式为(CH₂O)₂CO的有机化合物，可看作碳酸和乙二醇酯化形成的环状碳酸酯，在室温（25°C）下为无色透明晶体，易溶于水，在其熔点（34-37°C）以上，它是无色无味的液体^[2]。

制备方式及会进行的反应

碳酸乙烯酯可由在不同种的阳离子和错合物催化下，由环氧乙烷和二氧化碳反应制得：^[3]^[4]

{\ce {(CH2)2O +CO2->(CH2O)2CO}}

在实验室中，碳酸乙烯酯也可由在150℃温度，3千帕的压力下，在氧化锌的催化下由尿素和乙二醇的反应制得：^[5]

{\ce {(NH2)2CO +HO-CH2-CH2-OH->(CH2O)2CO +2NH3}}

碳酸乙烯酯（和碳酸丙烯酯）可由和甲醇进行的酯交换反应转化为碳酸二甲酯（一种溶剂和温和的甲基化试剂）：

${\ce {(CH2O)2CO +2 CH3OH ->CH3OC(O)OCH3 +HO-CH2-CH2-OH}}$

应用

碳酸乙烯酯的分子偶极矩为4.9 D，可作为极性溶剂。^[6]^[7]

碳酸乙烯酯可作为在锂电池和锂离子电池中的高电容率的电解质组成。其他组成成分如碳酸二甲酯、碳酸甲乙酯、碳酸二乙酯和乙酸甲酯可以被加入电解质中以降低其黏性和熔点。^[8]

碳酸乙烯酯也可作为塑化剂，和碳酸亚乙烯酯，一种可用于化学合成或生成聚合物的化学物质，的前驱物。

草酰氯在商业制备上由对于碳酸乙烯酯的光氯化反应生成碳酸四氯乙烯酯作为前驱物：^[9] ${\ce {(CH2O)2CO +4Cl2->(CCl2O)2CO +4HCl}}$

碳酸四氯乙烯酯可在有三级胺或酰胺的催化下，降解为草酰氯。^[10] ${\ce {(CCl2O)2CO->(COCl)2 +COCl2}}$

参考资料

^ CID 7303 -- PubChem Compound Summary. pubchem.ncbi.nlm.nih.gov. [2008-03-15]. （原始内容存档于2012-10-13）.
^ JEFFSOL ETHYLENE CARBONATE （页面存档备份，存于互联网档案馆） catalog entry at www.huntsman.com. Accessed on 2010-02-18.
^ Buysch, Hans-Josef, Carbonic Esters, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a05_197
^ Comerford, James W.; Ingram, Ian D. V.; North, Michael; Wu, Xiao. Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings. Green Chemistry. 2015, 17 (4): 1966–1987. doi:10.1039/C4GC01719F.
^ Bhalchandra M. Bhanage; Shin-ichiro Fujita. Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis. Green Chemistry. 2003, 5 (4): 429–432. doi:10.1039/b304182d.
^ Ralph P. Seward; Ernest C. Vieira. The Dielectric Constants of Ethylene Carbonate and of Solutions of Ethylene Carbonate in Water, Methanol, Benzene and Propylene Carbonate. J. Phys. Chem. 1958, 62 (1): 127–128. doi:10.1021/j150559a041.
^ Richard Payne; Ignatius E. Theodorou. Dielectric properties and relaxation in ethylene carbonate and propylene carbonate. J. Phys. Chem. 1972, 76 (20): 2892–2900. doi:10.1021/j100664a019.
^ E. R. Logan; J. R. Dahn. A Study of the Physical Properties of Li-Ion Battery Electrolytes Containing Esters. J. Electrochem. Soc. 2018, 165 (2): A21–A30. OSTI 1469344. doi:10.1149/2.0271802jes.
^ Pfoertner, Karl-Heinz, Photochemistry, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a19_573
^ US Patent for Process for producing oxalyl chloride and intermediates Patent (Patent # 4,390,708 issued June 28, 1983) - Justia Patents Search. patents.justia.com. [2021-06-13]. （原始内容存档于2021-06-13）.

[1] CID 7303 -- PubChem Compound Summary. pubchem.ncbi.nlm.nih.gov. [2008-03-15]. （原始内容存档于2012-10-13）.

[jeffsol-2] JEFFSOL ETHYLENE CARBONATE （页面存档备份，存于互联网档案馆） catalog entry at www.huntsman.com. Accessed on 2010-02-18.

[ullmann-3] Buysch, Hans-Josef, Carbonic Esters, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a05_197

[4] Comerford, James W.; Ingram, Ian D. V.; North, Michael; Wu, Xiao. Sustainable metal-based catalysts for the synthesis of cyclic carbonates containing five-membered rings. Green Chemistry. 2015, 17 (4): 1966–1987. doi:10.1039/C4GC01719F.

[Bhanage-5] Bhalchandra M. Bhanage; Shin-ichiro Fujita. Transesterification of urea and ethylene glycol to ethylene carbonate as an important step for urea based dimethyl carbonate synthesis. Green Chemistry. 2003, 5 (4): 429–432. doi:10.1039/b304182d.

[seward-6] Ralph P. Seward; Ernest C. Vieira. The Dielectric Constants of Ethylene Carbonate and of Solutions of Ethylene Carbonate in Water, Methanol, Benzene and Propylene Carbonate. J. Phys. Chem. 1958, 62 (1): 127–128. doi:10.1021/j150559a041.

[payne-7] Richard Payne; Ignatius E. Theodorou. Dielectric properties and relaxation in ethylene carbonate and propylene carbonate. J. Phys. Chem. 1972, 76 (20): 2892–2900. doi:10.1021/j100664a019.

[logan-8] E. R. Logan; J. R. Dahn. A Study of the Physical Properties of Li-Ion Battery Electrolytes Containing Esters. J. Electrochem. Soc. 2018, 165 (2): A21–A30. OSTI 1469344. doi:10.1149/2.0271802jes.

[9] Pfoertner, Karl-Heinz, Photochemistry, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a19_573

[10] US Patent for Process for producing oxalyl chloride and intermediates Patent (Patent # 4,390,708 issued June 28, 1983) - Justia Patents Search. patents.justia.com. [2021-06-13]. （原始内容存档于2021-06-13）.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

制备方式及会进行的反应

应用

相关条目

参考资料