Fert-Butyl methyl ether

The nature of the initiation step, which may occur in a variety of ways, is not known in all cases. Commonly used ethers such as ethyl ether, isopropyl ether, tetrahydrofuran, and i)-dioxane are particulady prone to form explosive peroxides on prolonged storage and exposure to air and light (see Peroxides AND PEROXY COMPOUNDS, ORGANIC), and should contain antioxidants (qv) to prevent their build-up. One of the exceptions to the peroxide forming tendency of ethers is methyl fert-alkyl ethers such as methyl fert-butyl ether [1634-04-4] (MTBE) and fert-amyl methyl ether [994-05-8] (TAME). Both have shown htde tendency if any to form peroxides (2,8). 

Somsamak P, HH Richnow, MM Haggblom (2005) Carbon isotope fractionation during anaerobic biotransformation of methyl fert-butyl ether and ferf-amyl methyl ether. Environ Sci Technol 39 103-109. 

Sample hydrolyzed at room temperature and extracted with methyl fert-butyl ether (total phenol) and analyzed GC-FID NG NG Rick et al. 1982... 

Bouzas, A., Burguet, M.C., Montdn, J.B., and Munoz, R. Densities, viscosities, and refractive indices of the binary systems methyl fert-butyl ether -t 2-methylpentane, + 3-methylpentane, + 2,3-dimethylpentane, and + 2,2,4-trimethylpentane at 298.15 K, / Chem. Eng. Data, 45(2) 331-333, 2000. 

Kang, J.-W., Hung, H.-M., Lin, A., and Hoffmann, M.R. Sonolytic destruction of methyl fert-butyl ether by ultrasonic irradiation the role of O3, H2O2, frequency, and power density, Environ. Sci. Technol, 33(18) 3199-3205, 1999. 

Landmeyer, J.E., Chapelle, F.H., Herlong, H.H., and Bradley, P.M. Methyl fert-butyl ether biodegradation by indigenous aquifer microorganisms under natural and artificial oxic conditions. Environ. Sci. TechnoL., 35(6) 1118-1126, 2001. 

Methyl fert-Butyl Ether MTBE Methyl Tertiary Butyl Ether Noncyclic Aliphatic or Aromatic Ethers Tetrahydrofuran Organophosphonates... 

Methyl fert-butyl ether (MTBE) synthesis 69,70 SMBCR... 

Arif, M., Dellinger, B., Taylor P.H. (1997) Rate coefficients of hydroxyl radical reaction with dimethyl ether and methyl fert-butyl ether over an extended temperature range. J. Phys. Chem. A 101, 2436-2441. 

Krahenbuhl, M.A., Gmehling, J. (1994) Vapor pressure of methyl fert-butyl ether, ethyl fert-butyl ether, isopropyl tert-butyl ether, fert-amyl methyl ether, and ferf-amyl ethyl ether. J. Chem. Eng. Data 39, 759-762. 

Wallington, T.J., Dagaut, R, Liu, R., Kuoylo, M.J. (1988c) Gas-phase reactions of hydroxyl radicals with the fnel additives methyl fert-butyl ether and fert-bntyl alcohol over the temperatnre range 240-440 K. Environ. Sci. Technol. 22, 842-844. 

Methanol is toxic to humans, causing blindness in low doses (15 mL) and death in larger amounts (100—250 mL). Industrially, it is used both as a solvent and as a starting material for production of formaldehyde (CHjO), acetic acid (CH COOH), and the gasoline additive methyl fert-butyl ether... 

Mitsubishi Rayon in Japan has commercialized a three-step process on the basis of a two-step catalytic oxidation of isobutene, preferentially through f-butanol as primary intermediate. This process suffers not only from a relatively moderate overall MMA yield ( 80%), but also from increasing isobutene cost due to its alternative use for MTBE (methyl fert.-butyl ether) production as a gasoline additive. 

Crown-6 (3.51 g, 13.28 mmol) was taken in 30 mL of THF, and the flask was cooled to -78 °C before addition of the phosphonate (2.90, 8.38 mmol) followed by dropwise addition of potassium hexamethyldisilazide (KHMDS 0.5 M in toluene, 16.0 mL, 8.38 mmol). After 10 min, the aldehyde (1.59 g, 6.68 mmol) was added in THF (10 mL). The reaction was quenched after 5 min with Nal ICO , solution. Extractive workup with methyl fert-butyl ether followed. The organic layer was then dried over MgSO4 and filtered. The solvent was evaporated in vacuo, and the crude product was chromatographed (hexane/EtOAc, 3 1) to give 1.73 g (85%) of the (Z)-a,p-unsaturated ethyl ester. 

Occurrence of Methyl fert-Butyl Ether and Other Fuel Oxygenates in Source Water and Drinking Water of the United States... 

Cyclohexanol Cyclohexyl alcohol 94 CeHi20 Methyl fert-butyl ether 107 C5H,20... 

Phenyl methylpolysiloxane Polycyclic aromatic hydrocarbons, disinfection by-products, polychlorinated biphenyls, polychlorinated dibenzo-p-dioxins and dibenzofurans, organochlorine pesticides, polybrominated biphenyls, polybrominated diphenyl ethers, chlorinated paraffins, methyl-fert-butyl-ether... 

Chlorinated paraffins Chlorophenols, methyl fert-butyl ether Organochlorine and organophosphorus pesticides, biocides... 

ACN = acetonitrile BuOH = butanol MBE = methyl fert-butyl ether MP = mobile phase SP = stationary phase. DEHPA = di-[2-ethylhexyl]phosphoric acid TEA = trifluoroacetic acid MP = mobile phase SP = stationary phase. 

In the commercial synthesis of methyl fert-butyl ether (MTBE), once used as an antiknock, octane-improving gasoline additive, 2-methylpropene and methanol are passed over an acid catalyst to give the ether. Propose a mechanism for this reaction. (See Examples 5.5,5.6)... 

MTBE Methyl fert-butyl ether DIB Di-iso-butene or iso-octene WHSV Weight hourly space velocity PAI Polyamideimide... 

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