Propylene carbonate

Propylene carbonate[1]
IUPAC name 4-Methyl-1,3-dioxolan-2-one
Other names Cyclic propylene carbonate Carbonic acid propylene ester Cyclic 1,2-propylene carbonate Propylene glycol cyclic carbonate 1,2-Propanediol carbonate 4-Methyl-2-oxo-1,3-dioxolane Arconate 5000 Texacar PC
Identifiers
CAS number	108-32-7 Y
PubChem	7924
ChemSpider	10609770 Y
UNII	8D08K3S51E Y
Jmol-3D images	Image 1
SMILES OC(=O)OCC(C)OC(=O)[O-]
InChI InChI=1S/C5H8O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/p-1 Y Key: ZEBXBLIKXVICMJ-UHFFFAOYSA-M Y InChI=1/C5H8O6/c1-3(11-5(8)9)2-10-4(6)7/h3H,2H2,1H3,(H,6,7)(H,8,9)/p-1 Key: ZEBXBLIKXVICMJ-REWHXWOFAP
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
Flash point	132 °C
Autoignition temperature	455 °C
Y carbonate (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Propylene carbonate (often abbreviated PC) is an organic compound, a cyclic carbonate of propylene glycol.^[4] This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonate exists as two enantiomers but is often used as the racemic mixture.^[5]

Preparation

Propylene carbonate is a byproduct of the synthesis of polypropylene carbonate from propylene oxide and carbon dioxide. It can be intentionally manufactured from the same feedstocks, using different reaction conditions. It can be also synthesized from, e.g., urea and propylene glycol over zinc-iron double oxide catalyst.

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 some cosmetics.^[9] It is also used as plasticizer.

See also

• Ethylene carbonate

References

1. ^ Propylene carbonate at Sigma-Aldrich
2. ^ CRC Handbook of Chemistry and Physics - Student Edition. 76th Edition ed, ed. D.R. Lide. 1995: CRC Press.
3. ^ CRC Handbook of Chemistry and Physics - Student Edition. 76th Edition ed, ed. D.R. Lide. 1995: CRC Press.
4. ^ WebBook page for propylene carbonate
5. ^ Dieter Stoye “Solvents” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Wienheim. doi:10.1002/14356007.a24_437
6. ^ CRC Handbook of Chemistry and Physics, 91st Ed. 2010-2011. <http://www.hcpnetbase.com>.
7. ^ 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
8. ^ Doron Aurbach (1999), "Nonaqueous Electrochemistry", Marcel Dekker, Inc.
9. ^ Record in the Household Products Database of NLM