Propylene carbonate
| Propylene carbonate[1] | |
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4-Methyl-1,3-dioxolan-2-one |
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Other names
Cyclic propylene carbonate |
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| Identifiers | |
| CAS number | 108-32-7  |
| PubChem | 7924 |
| ChemSpider | 10609770 |
| UNII | 8D08K3S51E |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C4H6O3 |
| Molar mass | 102.09 g/mol |
| Appearance | Colorless liquid |
| Density | 1.205 g/cm3 |
| Melting point |
-55 °C, 218 K, -67 °F |
| Boiling point |
240 °C, 513 K, 464 °F |
| Solubility in water | Very soluble [2] |
| Refractive index (nD) | 1.4189 [3] |
| Hazards | |
| MSDS | MSDS by Mallinckrodt Baker |
| R-phrases | R36 |
| S-phrases | S26 S36 |
| Main hazards | Xi |
| NFPA 704 |
 1
1
1
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| Flash point | 132 °C |
| Autoignition temperature |
455 °C |
 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Propylene carbonate (often abbreviated PC) is an organic compound with the formula CH3C2H4O2CO. It is a carbonate ester derived propylene glycol.[4] This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonate is chiral but is used exclusively as the racemic mixture.[5]
Contents |
[edit] Preparation
Propylene carbonate is a byproduct of the synthesis of polypropylene carbonate from propylene oxide and carbon dioxide. It can be manufactured from the same feedstocks, using different reaction conditions. It can be also prepared from, e.g., urea and propylene glycol over zinc-iron double oxide catalyst.
[edit] Applications
Propylene carbonate is used in a variety of syntheses and applications 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).[6] 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.[7]
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.[8]
Propylene carbonate can also be found in some adhesives, paint strippers, and in cosmetics.[9] It is also used as plasticizer.
[edit] Health Effects (in cosmetics)
Propylene Carbonate is, in a report made by American College of Toxicology 1987, considered to have no health effects as it is used in cosmetic products. Typically the concentration of propylene carbonate range up to 5 %, and tests were made with concentrations of 10 % - which had no effects on human skin.[citation needed]
[edit] See also
[edit] References
- ^ Propylene carbonate at Sigma-Aldrich
- ^ CRC Handbook of Chemistry and Physics - Student Edition. 76th Edition ed, ed. D.R. Lide. 1995: CRC Press.
- ^ CRC Handbook of Chemistry and Physics - Student Edition. 76th Edition ed, ed. D.R. Lide. 1995: CRC Press.
- ^ WebBook page for propylene carbonate
- ^ Dieter Stoye “Solvents” in Ullmann's Encyclopedia of Industrial Chemistry2002, Wiley-VCH, Wienheim. doi:10.1002/14356007.a24_437
- ^ CRC Handbook of Chemistry and Physics, 91st Ed. 2010-2011. <http://www.hcpnetbase.com>.
- ^ J. Jorné and C. W. Tobias (1975), Electrodeposition of the alkali metals from propylene carbonate. Journal of Applied Electrochemistry, volume 5 issue 4, pp. 279-290. doi:10.1007/BF00608791
- ^ Doron Aurbach (1999), "Nonaqueous Electrochemistry", Marcel Dekker, Inc.
- ^ Record in the Household Products Database of NLM
