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Concept
Carbonate ester
Summary
In organic chemistry, a carbonate ester (organic carbonate or organocarbonate) is an ester of carbonic acid. This functional group consists of a carbonyl group flanked by two alkoxy groups. The general structure of these carbonates is and they are related to esters (), ethers () and also to the inorganic carbonates.
Monomers of polycarbonate (e.g. Makrolon or Lexan) are linked by carbonate groups. These polycarbonates are used in eyeglass lenses, compact discs, and bulletproof glass. Small carbonate esters like dimethyl carbonate, ethylene carbonate, propylene carbonate are used as solvents, dimethyl carbonate is also a mild methylating agent.
Carbonate esters have planar OC(OC)2 cores, which confers rigidity. The unique O=C bond is short (1.173 Å in the depicted example), while the C-O bonds are more ether-like (the bond distances of 1.326 Å for the example depicted).
Carbonate esters can be divided into three structural classes: acyclic, cyclic, and polymeric. The first and general case is the acyclic carbonate group. Organic substituents can be identical or not. Both aliphatic or aromatic substituents are known, they are called dialkyl or diaryl carbonates, respectively. The simplest members of these classes are dimethyl carbonate and diphenyl carbonate.
Alternatively, the carbonate groups can be linked by a 2- or 3-carbon bridge, forming cyclic compounds such as ethylene carbonate and trimethylene carbonate. The bridging compound can also have substituents, e.g. CH3 for propylene carbonate. Instead of terminal alkyl or aryl groups, two carbonate groups can be linked by an aliphatic or aromatic bifunctional group.
A third family of carbonates are the polymers, such as poly(propylene carbonate) and poly(bisphenol A carbonate) (e.g. Makrolon or Lexan).
Organic carbonates are not prepared from inorganic carbonate salts.
Two main routes to carbonate esters are practiced: the reaction of an alcohol (or phenol) with phosgene (phosgenation), and the reaction of an alcohol with carbon monoxide and an oxidizer (oxidative carbonylation).
Official source
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