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Dibenzyl carbonate
Names
	IUPAC name Diphenyl carbonate
	Other names Phenyl carbonate
Identifiers
CAS Number	102-09-0 =;
3D model (JSmol)	Interactive image;
ChemSpider	7315 ;
KEGG	C14507 ;
UNII	YWV401IDYN ;
	InChI InChI=1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H Key: ROORDVPLFPIABK-UHFFFAOYSA-N ; 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;
	SMILES O=C(Oc1ccccc1)Oc2ccccc2;
Properties
Chemical formula	C13H10O3
Molar mass	214.216 g/mol
Density	1.1215 g/cm3 at 87 °C
Melting point	83 °C
Boiling point	306 °C
Solubility in water	insoluble
Solubility	soluble in ethanol, diethyl ether, carbon tetrachloride, acetic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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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]

^ 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.
^ ^a ^b Hans-Josef Buysch. "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197/full. ISBN 978-3527306732.

Category:Monomers Category:Carbonate esters

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[hand-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

[ioc-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-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.

[ullmann-5] Hans-Josef Buysch. "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197/full. ISBN 978-3527306732.

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