Trimethylene Carbonate
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Trimethylene Carbonate
Trimethylene carbonate, or 1,3-propylene carbonate, is a 6-membered cyclic carbonate ester. It is a colourless solid that upon heating or catalytic ring-opening converts to poly(trimethylene carbonate) (PTMC). Such polymers are called aliphatic polycarbonates and are of interest for potential biomedical applications. An isomeric derivative is propylene carbonate, a colourless liquid that does not spontaneously polymerize. Preparation This compound may be prepared from 1,3-propanediol and ethyl chloroformate (a phosgene substitute), or from oxetane and carbon dioxide with an appropriate catalyst: :HOC3H6OH + ClCO2C2H5 → C3H6O2CO + C2H5OH + HCl :C3H6O + CO2 → C3H6O2CO This cyclic carbonate undergoes ring-opening polymerization to give poly(trimethylene carbonate), abbreviated PTMC. : Medical devices The polymer PTC is of commercial interest as a biodegradable polymer with biomedical applications. A block copolymer of glycolic acid and trimethylene carbonate (TMC) is the m ...
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Carbonate Esters
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. Structures 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 polymeri ...
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Carbonate Ester
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. Structures 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 ...
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Poly(trimethylene Carbonate)
Poly(trimethylene carbonate) (PTMC) is an aliphatic polycarbonate synthesized from the 6-membered cyclic carbonate, trimethylene carbonate (1,3-propylene carbonate or 1,3-Dioxan-2-one). Trimethylene carbonate (TMC) is a colorless crystalline solid with melting point ranging between 45°C and 48 °C and boiling point at 255ºC (at 760 mmHg). TMC is originally synthesized from 1,3-propanediol with phosgene or carbon monoxide, which are highly poisonous gases. Another route is from the transesterification of 1,3-propanediol and dialkylcarbonates. This route is considered "greener" compared to the other one, since precursors can be obtained from renewable resources and carbon dioxide. Synthesis In opposition to five-membered cyclic carbonate, the six-membered ones like trimethylene carbonate are thermodynamically less stable than its polymer, undergoing the ring-opening polymerization with retention of CO_2 in the polymer structure, and generation an aliphatic polycarbonate. ...
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Propylene Carbonate
Propylene carbonate (often abbreviated PC) is an organic compound with the formula C4H6O3. It is a cyclic carbonate ester derived from propylene glycol. This colorless and odorless liquid is useful as a polar, aprotic solvent. Propylene carbonate is chiral, but is used as the racemic mixture in most contexts. Preparation Although many organic carbonates are produced using phosgene, propylene and ethylene carbonates are exceptions. They are mainly prepared by the carbonation of the epoxides (epoxypropane, or propylene oxide here): :CH3CHCH2O + CO2 → CH3C2H3O2CO The process is particularly attractive since the production of these epoxides consumes carbon dioxide. Thus this reaction is a good example of a green process. The corresponding reaction of 1,2-propanediol with phosgene is complex, yielding not only propylene carbonate but also oligomeric products. Propylene carbonate can also be synthesized from urea and propylene glycol over zinc acetate. Applications As a ...
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Ethyl Chloroformate
Ethyl chloroformate is the ethyl ester of chloroformic acid. It is a reagent used in organic synthesis for the introduction of the ethyl carbamate protecting group and for the formation of carboxylic anhydrides. Preparation Ethyl chloroformate can be prepared using ethanol and phosgene Phosgene is the organic chemical compound with the formula COCl2. It is a toxic, colorless gas; in low concentrations, its musty odor resembles that of freshly cut hay or grass. Phosgene is a valued and important industrial building block, espe ...: : Safety Ethyl chloroformate is a highly toxic, flammable, corrosive substance. It causes severe burns when comes in contact with eyes and/or skin, can be harmful if swallowed or inhaled. References {{Authority control Chloroformates Reagents for organic chemistry ...
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Oxetane
Oxetane, or 1,3-propylene oxide, is a heterocyclic organic compound with the molecular formula , having a four-membered ring with three carbon atoms and one oxygen atom. The term "an oxetane" or "oxetanes" refer to any organic compound containing the oxetane ring. Production A typical well-known method of preparation is the reaction of potassium hydroxide with 3-chloropropyl acetate at 150 °C: : Yield of oxetane made this way is c. 40%, as the synthesis can lead to a variety of by-products. Another possible reaction to form an oxetane ring is the Paternò–Büchi reaction. The oxetane ring can also be formed through diol cyclization as well as through decarboxylation of a six-membered cyclic carbonate. Taxol Paclitaxel (Taxol) is an example of a natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural prod ...
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Carbon Dioxide
Carbon dioxide (chemical formula ) is a chemical compound made up of molecules that each have one carbon atom covalently double bonded to two oxygen atoms. It is found in the gas state at room temperature. In the air, carbon dioxide is transparent to visible light but absorbs infrared radiation, acting as a greenhouse gas. It is a trace gas in Earth's atmosphere at 421 parts per million (ppm), or about 0.04% by volume (as of May 2022), having risen from pre-industrial levels of 280 ppm. Burning fossil fuels is the primary cause of these increased CO2 concentrations and also the primary cause of climate change.IPCC (2022Summary for policy makersiClimate Change 2022: Mitigation of Climate Change. Contribution of Working Group III to the Sixth Assessment Report of the Intergovernmental Panel on Climate Change Cambridge University Press, Cambridge, United Kingdom and New York, NY, USA Carbon dioxide is soluble in water and is found in groundwater, lakes, ice caps, ...
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TCM Polymerization
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Glycolic Acid
Glycolic acid (or hydroxyacetic acid; chemical formula HOCH2CO2H) is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate (sometimes spelled "glycollate") is a salt or ester of glycolic acid. History The name "glycolic acid" was coined in 1848 by French chemist Auguste Laurent (1807–1853). He proposed that the amino acid glycine—which was then called ''glycocolle''—might be the amine of a hypothetical acid, which he called "glycolic acid" (''acide glycolique''). Glycolic acid was first prepared in 1851 by German chemist Adolph Strecker (1822–1871) and Russian chemist Nikolai Nikolaevich Sokolov (1826–1877). They produced it by treating hippuric acid with nitric acid and nitrogen dioxide to form an ester of benzoic acid and glycolic acid (C6H5C(=O)OCH2COOH), which they called "benzoglycolic acid" (''Benzoglykolsäure''; also benzoyl glycolic acid). ...
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Ethylene Carbonate
Ethylene carbonate (sometimes abbreviated EC) is the organic compound with the formula (CH2O)2CO. It is classified as the Cyclic compound, cyclic carbonate ester of ethylene glycol and carbonic acid. At room temperature (25 °C) ethylene carbonate is a transparent crystalline solid, practically odorless and colorless, and somewhat soluble in water. In the liquid state (m.p. 34-37 °C) it is a colorless odorless liquid. JEFFSOL ETHYLENE CARBONATE
catalog entry at www.huntsman.com. Accessed on 2010-02-18.


Production and reactions

Ethylene carbonate is produced by the reaction between ethylene oxide and carbon dioxide. The reaction is catalyzed by a variety of cations and complexes: :(CH2)2O + CO2
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