diphenyl carbonate
   HOME

TheInfoList



Diphenyl carbonate is the
organic compound In , organic compounds are generally any s that contain - . Due to carbon's ability to (form chains with other carbon s), millions of organic compounds are known. The study of the properties, reactions, and syntheses of organic compounds compr ...
with the formula (C6H5O)2CO. It is classified as an acyclic
carbonate ester A carbonate ester (organic carbonate or organocarbonate) is an ester An ester is a chemical compound derived from an acid (organic or inorganic) in which at least one –OH hydroxyl group is replaced by an –O– alkyl (alkoxy) group, as in the s ...

carbonate ester
. It is a colorless solid. It is both a
monomerA monomer ( ; '' mono-'', "one" + '' -mer'', "part") is a molecule File:Pentacene on Ni(111) STM.jpg, A scanning tunneling microscopy image of pentacene molecules, which consist of linear chains of five carbon rings. A molecule is an electrical ...

monomer
in combination with
bisphenol A Bisphenol A (BPA) is an organic compound#Synthetic compounds, organic synthetic compound with the chemical formula (CH3)2C(C6H4OH)2 belonging to the group of diphenylmethane derivatives and bisphenols, with two hydroxyphenyl Functional group, gro ...

bisphenol A
in the production of
polycarbonate Polycarbonates (PC) are a group of thermoplastic polymers containing carbonate groups in their chemical structures. Polycarbonates used in engineering are strong, tough materials, and some grades are optically transparent. They are easily worke ...

polycarbonate
polymer A polymer (; Greek ''wikt:poly-, poly-'', "many" + ''wikt:-mer, -mer'', "part") is a Chemical substance, substance or material consisting of very large molecules, or macromolecules, composed of many Repeat unit, repeating subunits. Due to thei ...

polymer
s 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 Phenol (also called carbolic acid) is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic (ring (chemistry), ring-shaped), plane (geometry), pl ...

phenol
is the most significant route.
Phosgenation Phosgene is the organic chemical compound with the chemical formula, formula COCl2. It is a colorless gas; in low concentrations, its odor resembles that of freshly cut hay or grass. Phosgene is a valued industrial building block, especially for ...

Phosgenation
of
phenol Phenol (also called carbolic acid) is an aromatic forms of benzene (top) combine to produce an average structure (bottom) In chemistry, aromaticity is a property of cyclic compound, cyclic (ring (chemistry), ring-shaped), plane (geometry), pl ...

phenol
can proceed under various conditions. The net reaction is as follows: : 2 PhOH + COCl2 → PhOCO2Ph + 2 HCl The use of
phosgene Phosgene is the organic chemical compound with the formula In science Science (from the Latin word ''scientia'', meaning "knowledge") is a systematic enterprise that Scientific method, builds and Taxonomy (general), organizes knowledge ...

phosgene
can be avoided by the oxidative
carbonylation Carbonylation refers to reaction Reaction may refer to a process or to a response to an action, event, or exposure: Physics and chemistry *Chemical reaction A chemical reaction is a process that leads to the IUPAC nomenclature for organic tra ...
of phenol with
carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom. It is the simplest molecule of the oxocarbon family. In ...

carbon monoxide
: : 2 PhOH + CO + → PhOCO2Ph + H2O
Dimethyl carbonate Dimethyl carbonate (DMC) is an organic compound , CH4; is among the simplest organic compounds. In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen chemical bond, bonds. Due to carbon's ability to C ...

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 Anisole, or methoxybenzene, is an organic compound , CH4; is among the simplest organic compounds. In chemistry Chemistry is the scientific discipline involved with Chemical element, elements and chemical compound, compounds composed of a ...

anisole
. Despite this, diphenyl carbonate made from non-phosgene sources has become a widely used raw material for the synthesis of
bisphenol-A Bisphenol A (BPA) is an organic synthetic compound with the chemical formula A chemical formula is a way of presenting information about the chemical proportions of atom An atom is the smallest unit of ordinary matter In classic ...

bisphenol-A
-polycarbonate in a melt polycondensation process.


Applications

Polycarbonates can be prepared by transesterifying diphenyl carbonate with
bisphenol A Bisphenol A (BPA) is an organic compound#Synthetic compounds, organic synthetic compound with the chemical formula (CH3)2C(C6H4OH)2 belonging to the group of diphenylmethane derivatives and bisphenols, with two hydroxyphenyl Functional group, gro ...

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.


References

{{DEFAULTSORT:Diphenyl Carbonate Monomers Carbonate esters