Cyclic propylene carbonate
Carbonic acid propylene ester
Cyclic 1,2-propylene carbonate
Propylene glycol cyclic carbonate
|Molar mass||102.09 g·mol−1|
|Melting point||−48.8 °C (−55.8 °F; 224.3 K)|
|Boiling point||242 °C (468 °F; 515 K)|
Refractive index (nD)
|MSDS||MSDS by Mallinckrodt Baker|
|Flash point||132 °C (270 °F; 405 K)|
|455 °C (851 °F; 728 K)|
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
|what is: / ?)(|
Propylene carbonate (often abbreviated PC) is an organic compound with the formula CH3C2H3O2CO. It is a carbonate ester derived from propylene glycol. This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonate is chiral but is used exclusively as the racemic mixture.
- CH3CHCH2O + CO2 → CH3C2H3O2CO
The process is particularly attractive since the production of these epoxides consumes carbon dioxide. Thus this reaction is a good example of a green process. The corresponding reaction of 1,2-propanediol with phosgene is complex, yielding not only propylene carbonate but also oligomeric products.
As a solvent
Propylene carbonate is used as a polar, aprotic solvent. It has a high molecular dipole moment (4.9 D), considerably higher that those of acetone (2.91 D) and ethyl acetate (1.78 D). It is possible, for example, to obtain potassium, sodium, and other alkali metals by electrolysis of their chlorides and other salts dissolved in propylene carbonate.
Due to its high dielectric constant of 64, it is frequently used as a high-permittivity component of electrolytes in lithium batteries, usually together with a low-viscosity solvent (e.g. dimethoxyethane). Its high polarity allows it to create an effective solvation shell around lithium ions, thereby creating a conductive electrolyte. However, it is not used in lithium-ion batteries due to its destructive effect on graphite.
Clinical studies indicate that propylene carbonate does not cause skin irritation or sensitization when used in cosmetic preparations, whereas moderate skin irritation is observed when used undiluted. No significant toxic effects were observed in rats fed propylene carbonate, exposed to the vapor, or exposed to the undiluted liquid.
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- Haynes, William M., ed. (2011). CRC Handbook of Chemistry and Physics (92nd ed.). Boca Raton, FL: CRC Press. ISBN 1439855110.
- Propylene carbonate at Sigma-Aldrich
- WebBook page for propylene carbonate
- Hans-Josef Buysch (2005), "Carbonic Esters", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_197
- Dieter Stoye (2005), "Solvents", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a24_437
- J. Jorné; C. W. Tobias (1975). "Electrodeposition of the alkali metals from propylene carbonate". J. Appl. Electrochem. 5 (4): 279–290. doi:10.1007/BF00608791.
- Doron Aurbach (1999). Nonaqueous Electrochemistry. CRC Press. ISBN 978-0824773342.
- Record in the Household Products Database of NLM
- Teo CA, Donald WA (May 2014). "Solution additives for supercharging proteins beyond the theoretical maximum proton-transfer limit in electrospray ionization mass spectrometry". Anal. Chem. 86 (9): 4455–62. doi:10.1021/ac500304r. PMID 24712886.
- "Environmental Profile for Propylene Carbonate". U.S. Environmental Protection Agency. 1998.