Propylene carbonate

Propylene carbonate

Names
IUPAC name 4-Methyl-1,3-dioxolan-2-one
Other names (R,S)-4-Methyl-1,3-dioxolan-2-one 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
3D model (Jmol)	Interactive image
ChemSpider	7636 N
ECHA InfoCard	100.003.248
PubChem	7924
UNII	8D08K3S51E Y
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
SMILES CC1COC(=O)O1
Properties
Chemical formula	C4H6O3
Molar mass	102.09 g·mol−1
Appearance	Colorless liquid
Density	1.205 g/cm3
Melting point	−48.8 °C (−55.8 °F; 224.3 K)
Boiling point	242 °C (468 °F; 515 K)
Solubility in water	Very soluble
Refractive index (nD)	1.4189
Hazards
Main hazards	Xi
Safety data sheet	MSDS by Mallinckrodt Baker
R-phrases	R36
S-phrases	S26 S36
NFPA 704	1 1 1
Flash point	132 °C (270 °F; 405 K)
Autoignition temperature	455 °C (851 °F; 728 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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.

Although many organic carbonates are produced using phosgene, propylene and ethylene carbonates are exceptions. They are mainly prepared by the carbonation of the epoxides (epoxypropane, or propylene oxide here):

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.

Propylene carbonate is used as a polar, aprotic solvent. It has a high molecular dipole moment (4.9 D), considerably higher than 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.