碳酸乙烯酯

碳酸乙烯酯
	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	色調白至黃的固體
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（英語：Ethylene carbonate，缩寫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）下为無色透明晶體，易溶於水，在其熔点（34-37°C）以上，它是無色無味的液體^[2]。

製備方式及會進行的反應

碳酸乙烯酯可由在不同種的陽離子和錯合物催化下，由環氧乙烷和二氧化碳反應製得：^[3]^[4]

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

在實驗室中，碳酸乙烯酯也可由在150℃溫度，3千帕的壓力下，在氧化鋅的催化下由尿素和乙二醇的反應製得：^[5]

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

碳酸乙烯酯（和碳酸丙烯酯）可由和甲醇進行的酯交換反應轉化為碳酸二甲酯（一種溶劑和溫和的甲基化試劑）：

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

應用

碳酸乙烯酯的分子偶极矩為4.9 D，可作為极性溶剂。^[6]^[7]

碳酸乙烯酯可作為在鋰電池和鋰離子電池中的高電容率的電解質組成。其他組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電解質中以降低其黏性和熔點。^[8]

碳酸乙烯酯也可作為塑化劑，和碳酸亞乙烯酯，一種可用於化學合成或生成聚合物的化學物質，的前驅物。

草醯氯在商業製備上由對於碳酸乙烯酯的光氯化反應生成碳酸四氯乙烯酯作為前驅物：^[9] ${\ce {(CH2O)2CO +4Cl2->(CCl2O)2CO +4HCl}}$

碳酸四氯乙烯酯可在有三級胺或醯胺的催化下，降解為草醯氯。^[10] ${\ce {(CCl2O)2CO->(COCl)2 +COCl2}}$

参考資料

^ 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）.

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製備方式及會進行的反應

應用

相關條目

参考資料