TAME

TAME
Name	TAME
IUPACName	tert‑Amyl methyl ether
CommonNames	2‑Methoxy‑2‑methylbutane; tert‑Pentyl methyl ether
Formula	C6H14O
MolarMass	102.17 g·mol−1
Density	0.76 g·cm−3 (liquid)
BoilingPoint	86–87 °C
FlashPoint	−6 °C
CASNumber	994-05-8

TAME is a branched ether used primarily as an oxygenate and solvent. It is a colorless, volatile liquid with low polarity and relatively high octane enhancing properties; it has been employed in fuel blending, laboratory organic synthesis, and niche industrial processes. TAME's physical characteristics, synthetic routes, and regulatory posture have been described in petrochemical, environmental, and analytical literature.

Etymology and Acronyms

The trivial name tert‑Amyl methyl ether derives from systematic nomenclature reflecting substitution on the pentane skeleton and an ether linkage between a tert‑amyl group and a methyl group. Alternative names such as 2‑Methoxy‑2‑methylbutane and tert‑Pentyl methyl ether appear in inventories and safety data sheets produced by IUPAC and agencies like the United States Environmental Protection Agency and the European Chemicals Agency. Abbreviations used in regulatory and industrial documents include TAME and tAME, which appear in reports from American Petroleum Institute, Energy Information Administration, and national fuel quality regulations in countries such as Argentina and Brazil.

Chemical Properties and Synthesis

TAME (C6H14O) is a tertiary ether with a tertiary alkyl substituent; its structure imparts steric hindrance that influences reactivity. Physical constants recorded in compendia from National Institute of Standards and Technology and industrial handbooks report a boiling point near 86–87 °C, a low dielectric constant compared with polar solvents listed by Royal Society of Chemistry, and limited solubility of polar solutes. Chemically, TAME is relatively resistant to acid‑catalyzed cleavage compared with primary or secondary ethers, reflecting the stabilized tertiary carbocation intermediate implicated in cleavage mechanisms studied in classical organic texts such as those by March and experimental studies from Journal of Organic Chemistry.

Industrial synthesis commonly proceeds by acid‑catalyzed alkylation of isobutene or isoamylene streams with methanol over solid or liquid acid catalysts; processes and catalyst systems have been developed and reported by groups at ExxonMobil, Shell, and university research teams at Massachusetts Institute of Technology and University of California, Berkeley. Typical catalysts include strong protonic acids, zeolites (e.g., H‑ZSM‑5 variants studied at ETH Zurich and University of Tokyo), and sulfonic resins documented in patents filed with the United States Patent and Trademark Office.

Applications and Uses

TAME has been evaluated and deployed as an oxygenate additive in gasoline to raise octane number and reduce knock, analogous to methyl tert‑butyl ether and ethyl tert‑butyl ether which featured in fuel oxygenation regulations in the United States and European Union. It has seen commercial use in Latin American fuel programs overseen by agencies such as the Argentine Secretariat of Energy and oil companies like YPF and Petrobras. In organic chemistry, TAME serves as a nonpolar, low‑reactivity solvent for reactions cataloged in methodology papers from journals such as Organic Letters and Tetrahedron Letters, and as a phase modifier in extraction procedures employed by laboratories at Imperial College London and Sorbonne University.

Specialty industrial roles include use in hydraulic fluids, coatings, and as a carrier solvent in fragrance and agrochemical formulations developed by firms like BASF, Syngenta, and Givaudan. Its volatility and odor profile have been characterized in sensory studies associated with the International Organization for Standardization methods and industry reports from Johnson Matthey and Dow Chemical Company.

Safety, Toxicity, and Environmental Impact

TAME is flammable with a low flash point; handling and storage recommendations are provided in safety data sheets issued by suppliers including Sigma‑Aldrich and Merck Group. Toxicology data compiled by Agency for Toxic Substances and Disease Registry and peer‑reviewed assessments indicate acute inhalation exposure can cause central nervous system depression analogous to other ethers; chronic effects and carcinogenicity profiles have been evaluated in rodent bioassays reported in publications from National Toxicology Program and independent research groups at Karolinska Institutet and Université de Montréal. Environmental fate studies, including biodegradation assays and fugacity modeling by researchers at Environment Canada and European Commission laboratories, show moderate persistence in aquatic compartments and low bioaccumulation potential relative to heavier hydrocarbons documented by Organisation for Economic Co‑operation and Development testing guidelines.

Regulatory treatment varies: some jurisdictions classify TAME under volatile organic compound (VOC) emission limits enforced by agencies like California Air Resources Board and European Environment Agency; fuel additive approvals and phase‑out decisions historically considered alternatives such as MTBE and regulatory frameworks like the Clean Air Act amendments and REACH registration.

Analytical Methods and Detection

Analytical quantitation of TAME in air, water, and fuel matrices utilizes gas chromatography coupled with flame ionization detection or mass spectrometry (GC‑FID, GC‑MS) as described in method compendia from United States Environmental Protection Agency and interlaboratory studies published by ASTM International committees. Headspace GC, purge‑and‑trap, and solid‑phase microextraction protocols have been validated by laboratories at National Institute for Occupational Safety and Health and reported in Journal of Chromatography A. Isotopically labeled internal standards synthesized in academic facilities at University of Groningen and commercial suppliers facilitate quantitative mass spectrometric assays used in forensic and environmental monitoring by agencies such as Metropolitan Police Service laboratories and state environmental agencies.

History and Development

Interest in tert‑alkyl methyl ethers arose in the late 20th century during efforts to find oxygenates that boost octane while minimizing the groundwater contamination issues associated with methyl tert‑butyl ether used in United States fuel programs. Industrial development involved collaborations among petrochemical companies including Exxon, Chevron, and TotalEnergies, with pilot plants and patent disclosures throughout the 1980s and 1990s. Academic investigations into catalytic routes and environmental behavior were pursued at institutions such as University of Cambridge, Caltech, and University of Texas at Austin, informing later regulatory and commercial decisions in fuel formulation and solvent usage.

Category:Ether compounds