Diphenyl carbonate

Diphenyl carbonate

Skeletal formula
Ball-and-stick model
Names
IUPAC name Diphenyl carbonate
Other names Phenyl carbonate
Identifiers
CAS Number	102-09-0 Y=
ChemSpider	7315 Y
Jmol 3D model	Interactive image
KEGG	C14507 Y
UNII	YWV401IDYN Y
InChI InChI=1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H Y Key: ROORDVPLFPIABK-UHFFFAOYSA-N Y 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 (181 °F; 356 K)
Boiling point	306 °C (583 °F; 579 K)
Solubility in water	insoluble
Solubility	soluble in ethanol, diethyl ether, carbon tetrachloride, acetic acid
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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 and a product of the decomposition of polycarbonates.

Production

World production capacity of diphenyl carbonate was 254,000 tonnes in 2002, and phosgenation of phenol is the most significant route. 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.

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.