碳酸乙叉酯

碳酸乙叉酯
	IUPAC名; 1,3-dioxolan-2-one
別名	ethylene glycol carbonate
識別
CAS號	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
性質
化學式	C3H4O3
摩爾質量	88.06 g·mol−1
外觀	色調白至黃的固體
密度	1.3210 g/cm3
熔點	34—37 °C（307—310 K）
沸點	243.0 °C（516 K）
溶解性（水）	可溶
危險性
警示術語	R：R41
安全術語	S：S26 S39
歐盟分類	具刺激性 (XI)
閃點	150℃
自燃溫度	465℃
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

碳酸乙烯酯（英語：Ethylene carbonate，縮寫EC）是結構式為(CH₂O)₂CO的有機化合物，可看作碳酸和乙二醇酯化形成的環狀碳酸酯，在室溫（25°C）下為無色透明晶體，易溶於水，在其熔點（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極矩為4.9 D，可作為極性溶劑。^[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] ${\ce {(CCl2O)2CO->(COCl)2 +COCl2}}$

參考資料

^ CID 7303 -- PubChem Compound Summary. pubchem.ncbi.nlm.nih.gov. [2008-03-15]. （原始內容存檔於2012-10-13）.
^ JEFFSOL ETHYLENE CARBONATE （頁面存檔備份，存於網際網路檔案館） 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]. （原始內容存檔於2021-06-13）.

[1] CID 7303 -- PubChem Compound Summary. pubchem.ncbi.nlm.nih.gov. [2008-03-15]. （原始內容存檔於2012-10-13）.

[jeffsol-2] JEFFSOL ETHYLENE CARBONATE （頁面存檔備份，存於網際網路檔案館） 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]. （原始內容存檔於2021-06-13）.

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製備方式及會進行的反應

應用

相關條目

參考資料