Ethylene carbonate (sometimes abbreviated EC) is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula (CH₂O)₂CO. It is classified as the

cyclic Cycle, cycles, or cyclic may refer to: Anthropology and social sciences * Cyclic history, a theory of history * Cyclical theory, a theory of American political history associated with Arthur Schlesinger, Sr. * Social cycle, various cycles in so ...

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 the ...

ethylene glycol Ethylene glycol ( IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol) with the formula . It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an o ...

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 Ethylene oxide is an organic compound with the formula . It is a cyclic ether and the simplest epoxide: a three-membered ring consisting of one oxygen atom and two carbon atoms. Ethylene oxide is a colorless and flammable gas with a faintly sw ...

and

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 t ...

. The reaction is catalyzed by a variety of cations and complexes: :(CH₂)₂O + CO₂ → (CH₂O)₂CO In the laboratory, ethylene carbonate can also be produced from the reaction of

urea Urea, also known as carbamide, is an organic compound with chemical formula . This amide has two amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest amide of carbamic acid. Urea serves an important ...

and

using

zinc oxide Zinc oxide is an inorganic compound with the formula . It is a white powder that is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, food supplements, rubbers, plastics, ceramics, glass, cement ...

as a catalyst at a temperature of 150 °C and a pressure of 3 kPa: :(NH₂)₂CO + HO−CH₂CH₂−OH → (CH₂O)₂CO + 2 NH₃ Ethylene carbonate (and

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 carbonat ...

) may be converted to dimethyl carbonate (a useful solvent and a mild methylating agent) via

transesterification In organic chemistry, transesterification is the process of exchanging the organic group R″ of an ester with the organic group R' of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst. The reaction ca ...

methanol Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is ...

: :C₂H₄CO₃ + 2 CH₃OH → CH₃OCO₂CH₃ + HOC₂H₄OH The transesterfication of ethylene carbonate by methanol can be catalyzed by a high surface area (thermally exfoliated) graphitic carbon nitride (g-C₃N₄₎ materials. This method reduces the chance of metal or halide contamination, and can offer yields of up to 60% at a temperature of 393 K. Dimethyl carbonate may itself be similarly transesterified to

diphenyl carbonate 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 a ...

, a

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, esp ...

-substitute: : CH₃OCO₂CH₃ + 2 PhOH → PhOCO₂Ph + 2 MeOH

Applications

Ethylene carbonate is used as a

polar Polar may refer to: Geography Polar may refer to: * Geographical pole, either of two fixed points on the surface of a rotating body or planet, at 90 degrees from the equator, based on the axis around which a body rotates *Polar climate, the cli ...

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

with a

molecular dipole moment In physics, a dipole () is an electromagnetic phenomenon which occurs in two ways: *An electric dipole deals with the separation of the positive and negative electric charges found in any electromagnetic system. A simple example of this system ...

of 4.9 D, only 0.1 D lower than that of

. It can be used as a high

permittivity In electromagnetism, the absolute permittivity, often simply called permittivity and denoted by the Greek letter ''ε'' (epsilon), is a measure of the electric polarizability of a dielectric. A material with high permittivity polarizes more in ...

component of

electrolyte An electrolyte is a medium containing ions that is electrically conducting through the movement of those ions, but not conducting electrons. This includes most soluble salts, acids, and bases dissolved in a polar solvent, such as water. Upon ...

s in

lithium batteries Lithium battery may refer to: * Lithium metal battery, a non-rechargeable battery with lithium as an anode ** Rechargeable lithium metal battery, a rechargeable counterpart to the lithium metal battery * Lithium-ion battery, a rechargeable batte ...

and

lithium-ion batteries A lithium-ion or Li-ion battery is a type of rechargeable battery which uses the reversible reduction of lithium ions to store energy. It is the predominant battery type used in portable consumer electronics and electric vehicles. It also se ...

. Other components like

diethyl carbonate Diethyl carbonate (sometimes abbreviated DEC) is an ester of carbonic acid and ethanol with the formula OC(OCH2CH3)2. At room temperature (25 °C) diethyl carbonate is a colorless liquid with a low flash point. Diethyl carbonate is used ...

, ethyl methyl carbonate, dimethyl carbonate and

methyl acetate Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish remo ...

can be added to those

s in order to decrease the

viscosity The viscosity of a fluid is a measure of its resistance to deformation at a given rate. For liquids, it corresponds to the informal concept of "thickness": for example, syrup has a higher viscosity than water. Viscosity quantifies the int ...

and

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state from solid to liquid. At the melting point the solid and liquid phase exist in equilibrium. The melting point of a substance depen ...

. A typical sodium intercalation type battery would use an electrolyte consisting of: fluoroethylene carbonate (FEC) (99%), metallic Na (99.9%), and 1.0 M

sodium perchlorate Sodium perchlorate is the inorganic compound with the chemical formula Na ClO4. It is a white crystalline, hygroscopic solid that is highly soluble in water and in alcohol. It is usually encountered as the monohydrate. The compound is noteworthy ...

(NaClO₄) solutions in ethylene carbonate and diethyl carbonate (EC/DEC), 1:1 v/v% battery-grade, mixed with FEC (10% by weight). Ethylene carbonate is also used as

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

, and as a precursor to

vinylene carbonate Vinylene carbonate (VC) or 1,3-dioxol-2-one, is the simplest unsaturated cyclic carbonic acid ester. Vinylene carbonate can also be thought of as the cyclic carbonate of the hypothetical (''Z'')-ethene-1,2-diol. The activated double bond in this ...

, which is used in polymers and in

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

Oxalyl chloride Oxalyl chloride is an organic chemical compound with the formula (COCl)2. This colorless, sharp-smelling liquid, the diacyl chloride of oxalic acid, is a useful reagent in organic synthesis. Preparation Oxalyl chloride was first prepared in 1892 ...

is produced commercially from ethylene carbonate.

Photochlorination Photochlorination is a chlorination reaction that is initiated by light. Usually a C-H bond is converted to a C-Cl bond. Photochlorination is carried out on an industrial scale. The process is exothermic and proceeds as a chain reaction initiated ...

gives the tetrachloroethylene carbonate: :C₂H₄O₂CO + 4 Cl₂ → C₂Cl₄O₂CO + 4 HCl The tetrachloride is degraded to oxalyl chloride by amine catalysts. :C₂Cl₄O₂CO → C₂O₂Cl₂ + COCl₂

External links

WebBook page for ethylene carbonate

References

{{DEFAULTSORT:Ethylene Carbonate Ester solvents Plasticizers Carbonate esters

Production and reactions

Applications

See also

External links

References