Diphenyl carbonate

Diphenyl carbonate

Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name Diphenyl carbonate
Other names Phenyl carbonate, di-
Identifiers
CAS Number	102-09-0  Y=
3D model (JSmol)	Interactive image
ChEBI	CHEBI:34722
ChemSpider	7315  Y
ECHA InfoCard	100.002.733
KEGG	C14507  Y
PubChem CID	7597
UNII	YWV401IDYN  Y
CompTox Dashboard (EPA)	DTXSID3020540
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	80–81 °C (176–178 °F; 353–354 K)
Boiling point	306 °C (583 °F; 579 K)
Solubility in water	insoluble
Solubility	soluble in ethanol, diethyl ether, carbon tetrachloride, acetic acid [1]
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H410, H411
Precautionary statements	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). Y  verify  (what is  YN ?) Infobox references

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. Hans-Josef Buysch (2000). "Carbonic Esters". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_197. ISBN   978-3-527-30673-2.
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.