Diphenyl carbonate
{{chembox
| Watchedfields = changed
| verifiedrevid = 445149838
| Name = Diphenyl carbonate
| ImageFile = Diphenyl carbonate 200.svg
| ImageSize =
| ImageName = Skeletal formula
| ImageFile1 = Diphenyl-carbonate-from-xtal-3D-bs-17.png
| ImageSize1 = 225px
| ImageName1 = Ball-and-stick model
| PIN = Diphenyl carbonate
| OtherNames = Phenyl carbonate, di-
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7315
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YWV401IDYN
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C14507
| InChI = 1/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
| SMILES = O=C(Oc1ccccc1)Oc2ccccc2
| InChIKey = ROORDVPLFPIABK-UHFFFAOYAY
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C13H10O3/c14-13(15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ROORDVPLFPIABK-UHFFFAOYSA-N
| CASNo = 102-09-0
| CASNo_Ref = {{cascite|correct|CAS}}=
| PubChem = 7597
| ChEBI = 34722
| EINECS =
}}
|Section2={{Chembox Properties
| Formula = C13H10O3
| MolarMass = 214.216 g/mol
| Appearance =
| Density = 1.1215 g/cm3 at 87 °C
| MeltingPtC = 83
| BoilingPtC = 306
| Solubility = insoluble
| SolubleOther = soluble in ethanol, diethyl ether, carbon tetrachloride, acetic acid
{{Citation
| last = Lide
| first = David R.
| author-link =
| last2 =
| first2 =
| author2-link =
| publication-date =
| date =
| year = 1998
| title = Handbook of Chemistry and Physics
| edition = 87
| volume =
| series =
| publication-place = Boca Raton, FL
| place =
| publisher = CRC Press
| id =
| isbn = 0-8493-0594-2
| doi =
| oclc =
| pages = 3–238
| url =
| accessdate =
}}
}}
|Section3={{Chembox Structure
| Coordination =
| CrystalStruct =
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|Section7={{Chembox Hazards
| GHSPictograms = {{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|302|410|411}}
| PPhrases = {{P-phrases|264|270|273|301+312|330|391|501}}
| ExternalSDS =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| FlashPt =
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|Section8={{Chembox Related
| OtherAnions =
| OtherCations =
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}}
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
{{Citation
| last = Wittcoff
| first = Harold
| author-link =
| last2 = Reuben
| first2 = B. G.
| author2-link =
| last3 = Plotkin
| first3 = Jeffrey S.
| author3-link =
| publication-date =
| date =
| year = 2004
| title = Industrial Organic Chemicals
| edition =
| volume =
| series =
| publication-place =
| place =
| publisher = Wiley-IEEE
| id =
| isbn = 978-0-471-44385-8
| doi =
| oclc =
| pages = 278
| url = https://books.google.com/books?id=4KHzc-nYPNsC&pg=PA278&dq=%22Diphenyl+carbonate%22
| accessdate = 2009-07-20
}} and a product of the decomposition of polycarbonates.
{{Citation
| last = ASM International
| first =
| author-link =
| last2 =
| first2 =
| author2-link =
| publication-date =
| date =
| year = 2003
| title = Characterization and Failure Analysis of Plastics
| edition =
| volume =
| series =
| publication-place =
| place =
| publisher = ASM International
| id =
| isbn = 978-0-87170-789-5
| doi =
| oclc =
| pages = 369
| url = https://books.google.com/books?id=RJWiilJLdxYC&pg=PA369&dq=%22Diphenyl+carbonate%22
| accessdate = 2009-07-20
}}
Production
World production capacity of diphenyl carbonate was 254,000 tonnes in 2002, and phosgenation of phenol is the most significant route.{{cite web | title = Diphenyl Carbonate | url = http://www.inchem.org/documents/sids/sids/102090.pdf | publisher = IPSC Inchem | accessdate = 2012-08-01 | archive-date = 2012-01-04 | archive-url = https://web.archive.org/web/20120104192704/http://inchem.org/documents/sids/sids/102090.pdf | url-status = dead }} 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 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. 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.{{cite book|last = Fukuoka|first = Shinsuke|publisher = Nova Science Publishers|title = Non-Phosgene Polycarbonate from CO2 - Industrialization of Green Chemical Process|year = 2012|isbn = 9781614708773}}
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.{{Ullmann | year = 2000 | doi = 10.1002/14356007.a05_197 | title = Carbonic Esters | author = Hans-Josef Buysch }}