乳酸乙酯

乳酸乙酯
IUPAC名
2-羥基丙酸乙酯
别名 Actylol[1]; Acytol[1]
识别
CAS号 687-47-8（左式左旋異構物）  checkY
97-64-3（外消旋混合物）  checkY
7699-00-5（右式右旋異構物）  checkY
PubChem 7344
ChemSpider 13837423
SMILES
 
  • CCOC(=O)C(C)O
InChI
 
  • 1/C5H10O3/c1-3-8-5(7)4(2)6/h4,6H,3H2,1-2H3
InChIKey LZCLXQDLBQLTDK-UHFFFAOYAV
RTECS OD5075000
性质
化学式 C5H10O3
摩尔质量 118.13 g·mol−1
外观 澄清至淡黃色液體
密度 1.03 g/cm3
熔点 -26 °C（247 K）
沸点 151—155 °C（424—428 K）
溶解性（水） 無限互溶
溶解性（乙醇
和醇類） 		無限互溶
[α]20℃
D 		−11.3°(左式異構物)
磁化率 -72.6·10−6 cm3/mol
结构
偶极矩 3.46 D [2]
危险性
警示术语 R：R10 R37 R41
安全术语 S：S2 S24 S26 S39
欧盟分类 刺激性 Xi
主要危害 刺激性 (Xi)
NFPA 704
2
3
0
 
相关物质
相关化学品 乳酸, 乳酸甲酯
若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

乳酸乙酯（示性式：CH3CH(OH)CO2CH2CH3），是一种有机手性酯，在常溫常壓下為无色液体。它是乳酸的乙醇酯。由於此化合物是天然衍生的，它很容易以单一对映异构体的形式获得。它通常用作溶剂。[3] 这种化合物被认为是可生物降解的，並可作為能以水洗的脱脂剂。乳酸乙酯天然少量存在于各种食物中，包括葡萄酒、鸡肉和各种水果。稀薄濃度的乳酸乙酯的气味温和，具黄油、奶油味，並些微帶有水果和椰子的香氣。 [4]

製備

乳酸乙酯由生物来源生产，可以是左旋左式(S)或右旋右式(R)的光學異構物 ，其旋光性具体取决於作乳酸来源的生物体。大多数從生物所獲取的乳酸乙酯是左旋左式乳酸乙酯((S)-乳酸乙酯)。在工业上，乳酸乙酯也可由从石油化工原料中生产，此時生成的乳酸乙酯為外消旋混合物组成。

应用

由于两种对映异构体都存在于自然界中，而且乳酸乙酯易於生物降解，因此乳酸乙酯及其水溶液被用作有机合成中對環境傷害低的「绿色溶剂」。 [5]由于其相对较低的毒性，乳酸乙酯常作為製備藥物的底物、食品添加剂[6]和香料。乳酸乙酯也可作為硝酸纤维素、醋酸纤维素和纤维素醚的溶剂。 [7]

擴展阅读

  • Jacqueline S. Bennett; Kaitlyn L. Charles; Matthew R. Miner; Caitlin F. Heuberger; Elijah J. Spina; Michael F. Bartels; Taylor Foreman. Ethyl lactate as a tunable solvent for the synthesis of aryl aldimines. Green Chem. 2009, 11 (2): 166–168. doi:10.1039/b817379f. 

参考資料

  1. ^ 1.0 1.1 Ethyl lactate CAS NO (97-64-3)-Molbase. www.molbase.com. [2021-06-16]. （原始内容存档于2020-02-16）.  （页面存档备份，存于互联网档案馆）
  2. ^ Aparicio, Santiago; Alcalde, Rafael. The green solvent ethyl lactate: an experimental and theoretical characterization. Green Chemistry. 2009, 11 (1): 65–78. doi:10.1039/b811909k. 
  3. ^ Stoye, Dieter, Solvents, Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a24_437 
  4. ^ Pereira, Carla S. M.; Silva, Viviana M. T. M.; Rodrigues, Alírio E. Ethyl lactate as a solvent: Properties, applications and production processes – a review. Green Chemistry. 2011, 13 (10): 2658. doi:10.1039/C1GC15523G. 
  5. ^ Dolzhenko, Anton V. Ethyl lactate and its aqueous solutions as sustainable media for organic synthesis. Sustainable Chemistry and Pharmacy. 2020, 18: 100322. doi:10.1016/j.scp.2020.100322 （英语）. 
  6. ^ [1] （页面存档备份，存于互联网档案馆）U.S. Food and Drug Administration, Center for Food Safety and Applied Nutrition
  7. ^ "Industrial Solvents Handbook" by Ernest W. Flick. 5th Edition. William Andrew Inc., 1998. ISBN 0-8155-1413-1, ISBN 978-0-8155-1413-8

 

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