Diphenyl carbonate

Diphenyl carbonate
Skeletal formula
Skeletal formula
Ball-and-stick model
Ball-and-stick model
Names
Preferred IUPAC name
Diphenyl carbonate
Other names
Phenyl carbonate, di-
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.733 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H checkY
    Key: ROORDVPLFPIABK-UHFFFAOYSA-N checkY
  • InChI=1/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
    Key: ROORDVPLFPIABK-UHFFFAOYAY
  • O=C(Oc1ccccc1)Oc2ccccc2
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]
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H410, H411
P264, P270, P273, P301+P312, P330, P391, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Diphenyl carbonate is the organic compound with the formula (C6H5O)2CO. It is classified as an acyclic carbonate ester. It is a colorless solid. It is both a monomer in combination with bisphenol A in the production of polycarbonate polymers[2][3] and a product of the decomposition of polycarbonates.[4]

Production

World production capacity of diphenyl carbonate was 254,000 tonnes in 2002, and phosgenation of phenol is the most significant route.[5] Phosgenation of phenol can proceed under various conditions. The net reaction is as follows:

2 PhOH + COCl2 → PhOCO2Ph + 2 HCl

The use of phosgene can be avoided by the oxidative carbonylation of phenol with carbon monoxide:[2]

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.[2] Despite this, diphenyl carbonate made from non-phosgene sources has become a widely used raw material for the synthesis of bisphenol-A-polycarbonate in a melt polycondensation process.[6]

Applications

Polycarbonates can be prepared by transesterifying diphenyl carbonate with bisphenol A. Phenol is a co-product. These polycarbonates may be recycled by reversing the process: transesterifying the polycarbonate with phenol to yield diphenyl carbonate and bisphenol A.[2]

References

  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. ^ a b c d Hans-Josef Buysch (2000). "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197. ISBN 978-3527306732.
  3. ^ 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
  4. ^ ASM International (2003), Characterization and Failure Analysis of Plastics, ASM International, p. 369, ISBN 978-0-87170-789-5, retrieved 2009-07-20
  5. ^ "Diphenyl Carbonate" (PDF). IPSC Inchem. Archived from the original (PDF) on 2012-01-04. Retrieved 2012-08-01.
  6. ^ Fukuoka, Shinsuke (2012). Non-Phosgene Polycarbonate from CO2 - Industrialization of Green Chemical Process. Nova Science Publishers. ISBN 9781614708773.