Diethyl carbonate (sometimes abbreviated DEC) is an

ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...

of carbonic acid and

ethanol Ethanol (abbr. EtOH; also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound. It is an Alcohol (chemistry), alcohol with the chemical formula . Its formula can be also written as or (an ethyl ...

with the formula OC(OCH₂CH₃)₂. At room temperature (25 °C) diethyl carbonate is a colorless liquid with a low

flash point The flash point of a material is the "lowest liquid temperature at which, under certain standardized conditions, a liquid gives off vapours in a quantity such as to be capable of forming an ignitable vapour/air mixture". (EN 60079-10-1) The fl ...

. Diethyl carbonate is used as a

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 ...

such as in

erythromycin Erythromycin is an antibiotic used for the treatment of a number of bacterial infections. This includes respiratory tract infections, skin infections, chlamydia infections, pelvic inflammatory disease, and syphilis. It may also be used duri ...

intramuscular injection Intramuscular injection, often abbreviated IM, is the injection of a substance into a muscle. In medicine, it is one of several methods for parenteral administration of medications. Intramuscular injection may be preferred because muscles have ...

s. It can be used as a 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 dis ...

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 ...

. It has been proposed as a fuel additive to support cleaner diesel fuel combustion because its high boiling point might reduce blended fuels' volatility, minimizing vapor buildup in warm weather that can block fuel lines.Walter, K. Scientists Discover Method for Cleaner Fossil Fuel. MR&D Magazine. 09/18/2017 - 3:16pm
/ref> As a fuel additive, it can reduce emissions such as volatile organic compounds, CO₂, and particulates.{{cite journal , last1=Shukla , first1=Kartikeya , last2=Srivastava , first2=Vimal Chandra , date=2016 , title=Diethyl carbonate: critical review of synthesis routes, catalysts used and engineering aspects , url=https://pubs.rsc.org/en/content/pdf/article/2016/ra/c6ra02518h , journal=RSC Advances , volume= 6, issue= 39, pages= 32624–32645, doi=10.1039/c6ra02518h , bibcode=2016RSCAd...632624S , access-date=Aug 3, 2021

Production

It can be made by reacting phosgene with ethanol, producing

hydrogen chloride The compound hydrogen chloride has the chemical formula and as such is a hydrogen halide. At room temperature, it is a colourless gas, which forms white fumes of hydrochloric acid upon contact with atmospheric water vapor. Hydrogen chloride ga ...

as a byproduct. Because

chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...

can react with oxygen to form phosgene, chloroform can be stabilized for storage by adding 1 part (by mass) of ethanol to 100 parts (by mass) of chloroform, so that any phosgene that forms is converted into diethyl carbonate. :2 CH₃CH₂OH + COCl₂ → CO₃(CH₂CH₃)₂ + 2

HCl HCL may refer to: Science and medicine * Hairy cell leukemia, an uncommon and slowly progressing B cell leukemia * Harvard Cyclotron Laboratory, from 1961 to 2002, a proton accelerator used for research and development * Hollow-cathode lamp, a spe ...

It can also be made by the alcoholysis of urea with ethanol. This reaction requires a heterogeneous catalysis that can act both as a Lewis acid and a base, such as various metal oxides. The reaction proceeds via the formation of the intermediary

ethyl carbamate Ethyl carbamate (also called urethane) is an organic compound with the formula CH3CH2OC(O)NH2. It is an ester of carbamic acid and a white solid. Despite its name, it is not a component of polyurethanes. Because it is a carcinogen, it is rarely us ...

. :2 CH₃CH₂OH + CO(NH₂)₂ → CO₃(CH₂CH₃)₂ + NH₃ It can also be synthesized directly from carbon dioxide and ethanol using various methods, and via oxidative

carbonylation Carbonylation refers to reactions that introduce carbon monoxide into organic and inorganic substrates. Carbon monoxide is abundantly available and conveniently reactive, so it is widely used as a reactant in industrial chemistry. The term carbon ...

with

carbon monoxide Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simple ...

. Another method is

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 can ...

from

dimethyl carbonate Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is ...

. Yet another method is from the reaction of

ethyl nitrite The chemical compound ethyl nitrite is an alkyl nitrite with a chemical formula C2H5NO2. It may be prepared from ethanol. : Uses It is used as a reagent with butanone to yield the dimethylglyoxime end product. Ethyl nitrite is the main ingre ...

and carbon monoxide, where the ethyl nitrite can be made from

nitric oxide Nitric oxide (nitrogen oxide or nitrogen monoxide) is a colorless gas with the formula . It is one of the principal oxides of nitrogen. Nitric oxide is a free radical: it has an unpaired electron, which is sometimes denoted by a dot in its che ...

and ethanol. This method requires a catalyst such as palladium.

References

Ester solvents Ethyl esters Carbonate esters

Production

See also

References