''tert''-Amyl methyl ether (TAME) is an

ether In organic chemistry, ethers are a class of compounds that contain an ether group—an oxygen atom connected to two alkyl or aryl groups. They have the general formula , where R and R′ represent the alkyl or aryl groups. Ethers can again be c ...

used as a fuel oxygenate. TAME derives from C5 distillation fractions of

naphtha Naphtha ( or ) is a flammable liquid hydrocarbon mixture. Mixtures labelled ''naphtha'' have been produced from natural gas condensates, petroleum distillates, and the distillation of coal tar and peat. In different industries and regions ''n ...

. It has an ethereous

odor An odor (American English) or odour (English in the Commonwealth of Nations, Commonwealth English; American and British English spelling differences#-our, -or, see spelling differences) is caused by one or more volatilized chemical compounds ...

. Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage.

Uses

TAME is mostly used as an

oxygenate Oxygenated chemical compounds contain oxygen as a part of their chemical structure. The term usually refers to oxygenated chemical compounds added to fuels. Oxygenates are usually employed as gasoline additives to reduce carbon monoxide and soot ...

to gasoline. It is added for three reasons: to increase

octane Octane is a hydrocarbon and an alkane with the chemical formula , and the condensed structural formula . Octane has many structural isomers that differ by the amount and location of branching in the carbon chain. One of these isomers, 2,2,4-Tri ...

enhancement, to replace banned

tetraethyl lead Tetraethyllead (commonly styled tetraethyl lead), abbreviated TEL, is an organolead compound with the formula Pb( C2H5)4. It is a fuel additive, first being mixed with gasoline beginning in the 1920s as a patented octane rating booster that al ...

, and to raise the

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...

content in

gasoline Gasoline (; ) or petrol (; ) (see ) is a transparent, petroleum-derived flammable liquid that is used primarily as a fuel in most spark-ignited internal combustion engines (also known as petrol engines). It consists mostly of organic co ...

. It is known that TAME in fuel reduces

exhaust Exhaust, exhaustive, or exhaustion may refer to: Law *Exhaustion of intellectual property rights, limits to intellectual property rights in patent and copyright law **Exhaustion doctrine, in patent law ** Exhaustion doctrine under U.S. law, in p ...

emissions Emission may refer to: Chemical products * Emission of air pollutants, notably: **Flue gas, gas exiting to the atmosphere via a flue ** Exhaust gas, flue gas generated by fuel combustion ** Emission of greenhouse gases, which absorb and emit rad ...

of some

volatile organic compounds Volatile organic compounds (VOCs) are organic compounds that have a high vapour pressure at room temperature Colloquially, "room temperature" is a range of air temperatures that most people prefer for indoor settings. It feels comfortable to a ...

. TAME is also used as a solvent in organic synthesis as a more environmentally friendly alternative to some of the classic ether solvents. It is characterized by a high boiling point (86 °C) and a low freezing point (−80 °C), allowing a wide range of reaction temperatures. TAME can be used as a safe reaction medium (e.g.

condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...

s, coupling reactions, such as

Grignard reaction The Grignard reaction () is an organometallic chemical reaction in which alkyl, allyl, vinyl, or aryl-magnesium halides ( Grignard reagent) is added to a carbonyl group in an aldehyde or ketone. This reaction is important for the formation of ...

s and

Suzuki reaction The Suzuki reaction is an organic reaction, classified as a cross-coupling reaction, where the coupling partners are a boronic acid and an organohalide and the catalyst is a palladium(0) complex. It was first published in 1979 by Akira Suzuki, ...

s, as well as metal hydride reductions) and as an extraction solvent to replace

dichloromethane Dichloromethane (DCM or methylene chloride, methylene bichloride) is an organochlorine compound with the formula . This colorless, volatile liquid with a chloroform-like, sweet odour is widely used as a solvent. Although it is not miscible with ...

, aromatics, and other ethers.

Toxicity

In an animal toxicology study, inhalation of high concentrations of TAME (4000 ppm) caused

central nervous system depression Central nervous system (CNS) depression is a physiological state that can result in a decreased rate of breathing, decreased heart rate, and loss of consciousness possibly leading to coma or death. It is the result of inhibited or suppressed brai ...

, leading to death in most cases.

References

{{DEFAULTSORT:Amyl Methyl Ether, Tert- Dialkyl ethers Oxygenates

Uses

Toxicity

See also

References