Names | |
---|---|
Preferred IUPAC name
Diphenyl carbonate | |
Other names
Phenyl carbonate, di-
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.733 |
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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: | |
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).
|
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]
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:
The use of phosgene can be avoided by the oxidative carbonylation of phenol with carbon monoxide: [2]
Dimethyl carbonate can also be transesterified with phenol:
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]
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]
Names | |
---|---|
Preferred IUPAC name
Diphenyl carbonate | |
Other names
Phenyl carbonate, di-
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.002.733 |
KEGG | |
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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: | |
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).
|
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]
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:
The use of phosgene can be avoided by the oxidative carbonylation of phenol with carbon monoxide: [2]
Dimethyl carbonate can also be transesterified with phenol:
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]
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]