Diphenyl carbonate

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Diphenyl carbonate
Skeletal formula
Ball-and-stick model
Names
IUPAC name
Diphenyl carbonate
Other names
Phenyl carbonate
Identifiers
3D model (Jmol)
ChemSpider
ECHA InfoCard 100.002.733
KEGG
UNII
Properties
C13H10O3
Molar mass 214.216 g/mol
Density 1.1215 g/cm3 at 87 °C
Melting point 83 °C (181 °F; 356 K)
Boiling point 306 °C (583 °F; 579 K)
insoluble
Solubility soluble in ethanol, diethyl ether, carbon tetrachloride, acetic acid[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diphenyl carbonate is an acyclic carbonate ester. It is both as a monomer in combination with bisphenol A in the production of polycarbonate polymers[2] and a product of the decomposition of polycarbonates.[3]

Production[edit]

World production capacity of diphenyl carbonate was 254,000 tonnes in 2002, and phosgenation of phenol is the most significant route.[4] Phosgenation of phenol can proceed under various conditions. The net reaction is as follows:

2 PhOH + COCl2 → PhOCO2Ph + 2 HCl

The use of toxic phosgene can be avoided by the oxidative carbonylation of phenol:

2 PhOH + CO + [O] → PhOCO2Ph + H2O

Dimethyl carbonate can also be transesterified with phenol:

CH3OCO2CH3 + 2 PhOH → PhOCO2Ph + 2 MeOH

The kinetics and thermodynamics of this reaction are not favorable For example, at higher temperatures, dimethyl carbonate undesirably methylates phenol to give anisole.[5]

Applications[edit]

Polycarbonates can be prepared by transesterifying diphenyl carbonate with bisphenol A, and phenol is a co-product. Phosgene is avoided as a result. These polycarbonates may be recycled by reversing the process: transesterifying the polycarbonate with phenol to yield diphenyl carbonate and bisphenol A.[5]

References[edit]

  1. ^ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–238, ISBN 0-8493-0594-2 
  2. ^ Wittcoff, Harold; Reuben, B. G.; Plotkin, Jeffrey S. (2004), Industrial Organic Chemicals, Wiley-IEEE, p. 278, ISBN 978-0-471-44385-8, retrieved 2009-07-20 
  3. ^ ASM International (2003), Characterization and Failure Analysis of Plastics, ASM International, p. 369, ISBN 978-0-87170-789-5, retrieved 2009-07-20 
  4. ^ "Diphenyl Carbonate" (PDF). IPSC Inchem. Retrieved 2012-08-01. 
  5. ^ a b Hans-Josef Buysch (2005), "Carbonic Esters", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_197/full