Diphenyl carbonate
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| Names | |
|---|---|
| IUPAC name
Diphenyl carbonate | |
| Other names
Phenyl carbonate | |
| Identifiers | |
102-09-0  = | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 7315 |
| ECHA InfoCard | 100.002.733 |
| KEGG | C14507 |
| UNII | YWV401IDYN |
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| 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
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
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
- ↑ Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–238, ISBN 0-8493-0594-2
- ↑ 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
- ↑ ASM International (2003), Characterization and Failure Analysis of Plastics, ASM International, p. 369, ISBN 978-0-87170-789-5, retrieved 2009-07-20
- ↑ "Diphenyl Carbonate" (PDF). IPSC Inchem. Retrieved 2012-08-01.
- 1 2 Hans-Josef Buysch (2005), "Carbonic Esters", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, doi:10.1002/14356007.a05_197/full