Fert-Butyl 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). 

Rohwerder T, U Breuer, D Benndorf, U Lechner, RH Muller (2006) The alkyl fert-butyl ether intermediate 2-hydroxyisobutyrate is degraded via a novel cobalamin-dependent mutase pathway. Appl Environ Microbiol 72 4128-4135. 

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... 

Propylene glycol mono-fert-butyl ether [57018-52-7] 7.7 0.40 Stephenson, 1993d ... 

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. 

Clofibrate Clofibrate, ethyl ether 2-(4-chloropheoxy)-M( -butyric acid (20.2.2), is synthesized by esterifying 2-(4-chlorophenoxy)-/yo-butyric acid (20.2.1) with ethyl alcohol. This is synthesized in a single-stage reaction from 4-chlorophenol, acetone, and chloroform in the presence of an alkali, evidently by initial formation of chlorethone-trichloro-tert-butyl alcohol, which under the reaction conditions is converted into (4-chlorophenoxy)trichloro-fert-butyl ether, and further hydrolyzed to the desired acid 20.2.1, which is further esterified with ethanol in the presence of inorganic acid [6-8]. 

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

Langer, S., E. Ljungstrom, I. Wangberg, T. J. Wallington, and O. J. Nielsen, Atmospheric Chemistry of Di-fert-butyl Ether—Rates and Products of the Reactions with Chlorine Atoms, Hydroxyl Radicals, and Nitrate Radicals, Int. J. Chem. Kinet, 28, 299-306 (1996). 

Arce, A., Rodriguez, O., and Soto A., Purification of ethyl fert-butyl ether from its mixtures with ethanol by using an ionic liquid, Chem. Eng.., 115, 219, 2006. 

If chelation of the metal was more efficient, by switching from a fert-butyl ether to a methoxymethyl ether, the use of an excess of ZnBr2 was efficient at accelerating... 

When the dimetallic species 210 was first deuteriated with MeOD and then subjected to iodinolysis, a 60/40 mixture of the two diastereomeric a-deuteriated iodides 267a and 267b was obtained. Although the use of a first small electrophile such as a MeOD did not enable efficient differentiation of the two carbon-metal bonds, a reversal of diastereose-lectivity was observed when the a-deuteriated dimetallic species 268 was first protonated with MeOH and then reacted with iodine. This result points towards the configurational stability of the resulting monoorganozinc species generated after reaction with a first electrophile, presumably due to the coordination by fert-butyl ether moiety (equation 127)162. 

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. 

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