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Propylene carbonate[1]
Propylene carbonate.png
Propylene-carbonate-3D-vdW.png
IUPAC name
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 Yes check.svgY
PubChem 7924
SMILES
Properties
Molecular formula C4H6O3
Molar mass 102.09 g/mol
Appearance Colorless liquid
Density 1.205 g/mL
Melting point

-55 °C, 218 K, -67 °F

Boiling point

240 °C, 513 K, 464 °F

Hazards
MSDS MSDS by Mallinckrodt Baker
R-phrases R36
S-phrases S26 S36
NFPA 704
NFPA 704.svg
1
1
1
 
Flash point 132 °C
Autoignition
temperature
455 °C
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Propylene carbonate (abbreviated PC) is an organic compound, a twofold ester of propylene glycol and carbonic acid.[2] This is a colorless odorless liquid is useful as a highly polar but aprotic solvent.[3]

Contents

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 synthetized from eg. urea and propylene glycol over zinc-iron double oxide catalyst.

Applications

Propylene carbonate is used as a polar solvent that, unlike water, does not donate protons to the dissolved subsances. It is relatively inert but has a high dipole moment (5), considerably higher that those of acetone (2.7) and ethyl acetate (1.7). 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.[4]

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 (eg. 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.[5]

Propylene carbonate can also be found in some adhesives, paint strippers, and in some cosmetics.[6] It is also used as plasticizer.

See also

References

  1. ^ Propylene carbonate at Sigma-Aldrich
  2. ^ WebBook page for propylene carbonate
  3. ^ Dieter Stoye “Solvents” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Wienheim. doi:10.1002/14356007.a24_437
  4. ^ 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
  5. ^ Doron Aurbach (1999), "Nonaqueous Electrochemistry", Marcel Dekker, Inc.
  6. ^ Record in the Household Products Database of NLM
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