Tert-Amyl methyl ether

Last updated
tert-Amyl methyl ether [1] [2]
Tert-amyl methyl ether.svg
Amyl methyl ether.png
Names
Preferred IUPAC name
2-Methoxy-2-methylbutane
Other names
tertiary-Amyl methyl ether; TAME; Methoxypentane
Identifiers
3D model (JSmol)
AbbreviationsTAME
ChemSpider
ECHA InfoCard 100.012.374 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3 Yes check.svgY
    Key: HVZJRWJGKQPSFL-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H14O/c1-5-6(2,3)7-4/h5H2,1-4H3
    Key: HVZJRWJGKQPSFL-UHFFFAOYAC
  • O(C(C)(C)CC)C
Properties
C6H14O
Molar mass 102.177 g·mol−1
AppearanceClear, colorless liquid
Density 0.76-0.78 g/mL [3]
Melting point −80 °C (−112 °F; 193 K)
Boiling point 86.3 °C (187.3 °F; 359.4 K)
10.71 g/L at 20 °C
1.3896
Hazards
Flash point −11 °C (12 °F; 262 K)
430 °C (806 °F; 703 K)
Explosive limits 1.0-7.1%
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

tert-Amyl methyl ether (TAME) is an ether used as a fuel oxygenate. TAME derives from C5 distillation fractions of naphtha. [4] It has an ethereous odor. [1] Unlike most ethers, it does not require a stabilizer as it does not form peroxides on storage. [5]

Contents

Other names: [6]

Uses

TAME is mostly used as an oxygenate to gasoline. It is added for three reasons: to increase octane enhancement, to replace banned tetraethyl lead, and to raise the oxygen content in gasoline. It is known that TAME in fuel reduces exhaust emissions of some volatile organic compounds. [1]

TAME is also used as a solvent in organic synthesis as a more environmentally friendly alternative to some of the classic ether solvents. [4] 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 reactions, coupling reactions, such as Grignard reactions and Suzuki reactions, as well as metal hydride reductions) and as an extraction solvent to replace dichloromethane, aromatics, and other ethers. [7] [ failed verification ]

A series of experiments were carried out in a batch reactor at the temperature range of 313-343 K to study the synthesis of tert-amyl ethyl ether from ethanol (EtOH) and 2-methyl-1-butene (2M1B) catalyzed by the NKC-9 ion-exchange resin. The suitable reaction pressure was obtained by using the method of the Gibbs free energy minimization. The activity coefficients of each component were accurately calculated using the Wilson method, then, the equilibrium constants was obtained. The effect of catalyst size, stirring rate, temperature and EtOH/2M1B molar ratio was investigated at the chosen pressure, respectively. A kinetic model which considered the variation of each component volume was established. The method of nonlinear least square combined with genetic algorithm (NLS-GA) was proposed to estimate the kinetic constant in the forward direction. Results indicated that simulated kinetics results were agreed well with the experimental data.

Toxicity

TAME was evaluated in 4-week rat inhalation studies sponsored by Amoco Corporation. Target vapor concentrations were 0, 500, 2000, or 4000 ppm for 6 h per day, 5 days per week, for 4 weeks. Exposure at 4000 ppm resulted in 25% mortality, apparently as a consequence of severe CNS depression. Body weight gain was decreased in the TAME high dose male rats. Significant effects on functional observational battery (FOB) parameters were only found in the high and mid-dose groups immediately after exposure. All affected FOB parameters were normal by the next day. TAME exposure significantly increased relative liver weights in the high and mid-dose groups. However, no treatment-related histopathologic findings were noted for the compound. Clinical chemistry and hematology findings were minimal with TAME exposure. The results indicate that 500 ppm was a NOAEL for TAME in these studies. [8]

Some other properties [6]

Relative vapor density (air = 1): 3.6

Vapor Pressure 75.2 [mmHg]

log Kow = 1.55 at 20 °C

Henry's Law constant = 1.32X10-3 atm-cu m/mol at 25 °C

Stability / Shelf Life: Stable under recommended storage conditions.

Autoignition Temperature: 415 °C

Decomposition: When heated to decomposition it emits acrid smoke and irritating vapors.

Odor Threshold: 0.02 [mmHg]

Kovats retention index

Standard non-polar 672.5, 674, 673, 669.3, 666

Semi-standard non-polar 678, 655, 668.3

Standard polar 790, 802.9

See also

Related Research Articles

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<span class="mw-page-title-main">Heptane</span> Chemical compound

Heptane or n-heptane is the straight-chain alkane with the chemical formula H3C(CH2)5CH3 or C7H16. When used as a test fuel component in anti-knock test engines, a 100% heptane fuel is the zero point of the octane rating scale (the 100 point is 100% iso-octane). Octane number equates to the anti-knock qualities of a comparison mixture of heptane and iso-octane which is expressed as the percentage of iso-octane in heptane, and is listed on pumps for gasoline (petrol) dispensed globally.

In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term alkyl is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of −CnH2n+1. A cycloalkyl group is derived from a cycloalkane by removal of a hydrogen atom from a ring and has the general formula −CnH2n−1. Typically an alkyl is a part of a larger molecule. In structural formulae, the symbol R is used to designate a generic (unspecified) alkyl group. The smallest alkyl group is methyl, with the formula −CH3.

Methyl <i>tert</i>-butyl ether Chemical compound

Methyl tert-butyl ether (MTBE), also known as tert-butyl methyl ether, is an organic compound with a structural formula (CH3)3COCH3. MTBE is a volatile, flammable, and colorless liquid that is sparingly soluble in water. Primarily used as a fuel additive, MTBE is blended into gasoline to increase its octane rating and knock resistance, and reduce unwanted emissions.

Ethyl <i>tert</i>-butyl ether Oxygenate gasoline additive in the production of gasoline from crude oil

Ethyl tertiary-butyl ether (ETBE), also known as ethyl tert-butyl ether, is commonly used as an oxygenate gasoline additive in the production of gasoline from crude oil. ETBE offers equal or greater air quality benefits than ethanol, while being technically and logistically less challenging. Unlike ethanol, ETBE does not induce evaporation of gasoline, which is one of the causes of smog, and does not absorb moisture from the atmosphere.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

<span class="mw-page-title-main">Isobutylene</span> Unsaturated hydrocarbon compound (H2C=C(CH3)2)

Isobutylene is a hydrocarbon with the chemical formula (CH3)2C=CH2. It is a four-carbon branched alkene (olefin), one of the four isomers of butylene. It is a colorless flammable gas, and is of considerable industrial value.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

Oxygenated chemical compounds are hydrocarbons which contain at least one oxygen atom as a part of their chemical structure. The term often refers to oxygenated chemical compounds added to fuels. Oxygenates are usually employed as gasoline additives to reduce carbon monoxide and soot that is created during the burning of the fuel. Compounds related to soot, such as polyaromatic hydrocarbons (PAHs) and nitrated PAHs, are also reduced.

Glycol ethers are a class of chemical compounds consisting of alkyl ethers that are based on glycols such as ethylene glycol or propylene glycol. They are commonly used as solvents in paints and cleaners. They have good solvent properties while having higher boiling points than the lower-molecular-weight ethers and alcohols.

<span class="mw-page-title-main">Alkyl nitrite</span> Organic compounds of the form R–O–N=O

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<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

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 as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and thus is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.

<i>tert</i>-Amyl alcohol Chemical compound

tert-Amyl alcohol (TAA) or 2-methylbutan-2-ol (2M2B), is a branched pentanol.

<i>tert</i>-Amyl chloride Chemical compound

tert-Amyl chloride is an alkyl chloride used for flavoring and odorizing. At room temperature, it is a colorless liquid with an unpleasant odor. It can be synthesized from tert-amyl alcohol by an SN1 reaction.

<span class="mw-page-title-main">Butane</span> Organic compound

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<i>tert</i>-Butylthiol Chemical compound

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<i>tert</i>-Amyl ethyl ether Chemical compound

tert-Amyl ethyl ether (TAEE) is a chemical compound, classified as an ether, with the molecular formula C7H16O. It is used as an additive in gasoline fuels as an oxygenate and also as a solvent in organic chemistry.

References

  1. 1 2 3 "tert-AMYL METHYL ETHER (1,1-DIMETHYLPROPYL METHYL ETHER)". chemicalland21.com. Retrieved 2009-10-20.
  2. ↑ National Industrial Chemicals Notification and Assessment Scheme (2001). "t-Amyl methyl ether (TAME)" (PDF). Full Public Reports. Retrieved 2009-10-20.
  3. ↑ "tert-Amyl methyl ether". Sigma-Aldrich.
  4. 1 2 Prat, Denis; Wells, Andy; Hayler, John; Sneddon, Helen; McElroy, C. Robert; Abou-Shehada, Sarah; Dunn, Peter J. (2015-12-21). "CHEM21 selection guide of classical- and less classical-solvents". Green Chem. 18 (1): 288–296. doi: 10.1039/c5gc01008j . ISSN   1463-9270.
  5. ↑ Diaz, Arthur F.; Drogos, Donna L. (2001-11-06). Oxygenates in Gasoline. ACS Symposium Series. Vol. 799. American Chemical Society. pp. 138–152. doi:10.1021/bk-2002-0799.ch010. ISBN   978-0841237605.
  6. 1 2 PubChem. "tert-Amyl methyl ether". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-10-22.
  7. ↑ "INEOS Oligomers Products". INEOS. Archived from the original on 2017-11-07. Retrieved 2017-10-30.
  8. ↑ White, Russell D.; Daughtrey, Wayne C.; Wells, Mike S. (December 1995). "Health effects of inhaled tertiary amyl methyl ether and ethyl tertiary butyl ether". Toxicology Letters . 82–83: 719–724. doi:10.1016/0378-4274(95)03590-7. PMID   8597132.
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