Ferf-Butyl ethers

Baretto RD, KA Gray, K Anders (1995) Photocatalytic degradation of methyl-ferf-butyl ether in TiOj slurries a proposed reaction scheme Water Res 29 1243-1248. 

Steffan RJ, K McClay, S Vainberg, CW Condee, D Zhang (1997) Biodegradation of the gasoline oxygenates methyl ferf-butyl ether, ethyl ferf-butyl ether, and amyl tcrt-butyl ether by propane-oxidizing bacteria. Appl Environ Microbiol 63 4216-4222. 

FIGURE 11.3 Degradation of methyl ferf-butyl ether. 

Hanson JR, CE Ackerman, KM Scow (1999) Biodegradation of methyl ferf-butyl ether by a bacterial pure culture. Appl Environ Microbiol 65 4788-4792. 

Shih C-C, ME Davey, J Zhou, JM Tiedje, CS Criddle (1996) Effects of phenol feeding pattern on microbial community structure and cometabolism of trichloroethylene. Appl Environ Microbiol 62 2953-2960. Somsamak P, HH Richnow, MM Haggblom (2005) Carbon isotope fractionation during anaerobic biotransformation of methyl ferf-butyl ether and ferf-amyl methyl ether. Environ Sci Technol 39 103-109. Somsamak P, RM Cowan, MM Haggblom (2001) Anaerobic biotransformation of fuel oxygenates under sulfate-reducing conditions. EEMS Microbiol Ecol 37 259-264. 

Halden, R.U., Happel, A.M., and Schoen, S.R., Evaluation of standard methods for the analysis of methyl ferf-butyl ether and related oxygenates in gasoline-contaminated groundwater, Environmental Science Technology, 35 (7), 1469-1474, 2001. 

Xu XR, Gu J-D (2004) Elucidation of methyl ferf-butyl ether degradation with Fe2+/H202 by purge-and-trap gas chromatography-mass spectrometry. Micro-chemJ 77 71-77... 

Bierwagen, B.G., Keller, A.A. (2001) Measurement of Henry s law constant for methyl ferf-butyl ether using solid-phase microextraction. Environ. Toxicol. Chem. 20, 1625-1629. 

Extracts were further purified on neutral alumina cartridges conditioned by passing through 5 ml of hexane. Extracts were loaded in hexane and washed by 5 ml of hexane. The at- and /1-carotenes were removed by 3.5 ml of acetone-hexane (10 90, v/v), other carotenoids were eluted with acetone-hexane 30 70 and 70 30 v/v. Prepurification of pigments was performed in subdued light under a stream of nitrogen. Analyses were carried out in a C30 column (250 X 4.6 mm i.d., particle size 5/tm) using isocratic mobile phase composed of methyl-ferf-butyl ether (MTBE)-methanol (3 97 and 38 62, v/v) at a flow rate of 1 ml/min. The column was not thermostated separations were achieved at room temperature (about 23°C). Carotenoids were detected at 453 and 460 nm (lutein). The... 

Methyl ferf-butyl ether [1634-04-4] 0 0.01 Bennett and Philip, 1928 ... 

Methyl-l-butanol, see Isoamyl acetate Methyl ferf-butyl ether, see Methanol A-Methylcarbamic acid, see Carbofuran... 

CASRN 637-92-3 molecular formula CeH O FW 102.17 Chemical/Physical The atmospheric oxidation of ethyl ferf-butyl ether by OH radicals in the presence of nitric oxide yielded ferf-butyl formate as the major product. Minor products included formaldehyde and nitrogen dioxide. In the absence of nitric oxide, 2-ethoxy-2-methylpropanal is likely to form (Wallington and Japar, 1991). 

Degradation of methyl terf-butyl ether by bifunctional aluminum in the presence of oxygen was investigated by Lien and Wilkin (2002). Bifunctional aluminum was synthesized by sulfating aluminum metal with sulfuric acid. When the initial methyl terf-butyl ether concentration was 14.4 mg/L, 90% of methyl ferf-butyl ether degraded within 24 h forming acetone, methyl acetate, tert-hniyX alcohol, and ferf-butyl formate. Carbon disulfide was tentatively identified as a reaction product by GC/MS. Product yields were 27.6% for acetone, 18.4% for methyl acetate, 21% for tert-hniyX alcohol, and 6.1% ferf-butyl formate. When the initial concentration of methyl tert-butyl ether was reduced to 1.4 mg/L, 99.5% of methyl terCbutyl ether reacted. Yields of acetone, methyl acetate, and /erf-butyl alcohol were 54.7,17.2, and 13.2, respectively. 

Church, C.D., Pankow, J.F., and Tratnyek, P.G. Hydrolysis of ferf-butyl formate kinetics, products, and implications for the environmental impact of methyl ferf-butyl ether. Environ. Toxicol. Chem., 18(12) 2789-2796, 1999. 

Fischer, A., Muller, M., and Klasmeier, J. Determination of Henry s law constant for methyl ferf-butyl ether (MTBE) at groundwater temperatures, Chemosphere, 54(6) 689-694, 2004. 

Lien, H.-L. and Wilkin, R. Reductive activation of dioxygen for degradation of methyl ferf-butyl ether by bifunctional aluminum. Environ. Sci. Technol, 36(20) 4436-4440, 2002. 

Munoz, R., Burguet, M.C., Morlanes, N., and Garci a-Usach, F. Densities, refractive indices, and excess molar volumes of binary and tertiary systems containing isobutyl alcohol, ethanol, 2-methylpentane, and methyl ferf-butyl ether at 298.15 K, J. Chem. Eng. Data, 45(4) 585-589, 2000. 

Wallington, T.J., Dagaut, P., Liu, R., and Kurylo, MJ. Gas-phase reactions of hydroxy radicals with the fuel additives methyl f-butyl ether and f-butyl alcohol over the temperature range 240-440 K, Environ. Sci. TechnoL, 22(7) 842-844, 1988c. Wallington, T.J. and Japar, S.M. Atmospheric chemistry of diethyl ether and ethyl ferf-butyl ether. Environ. Sci TechnoL, 25(3) 410-415, 1991. 

The formal isomerization enthalpies of methyl n-butyl ether to methyl terf-butyl ether and of di-n-butyl ether to n-butyl ferf-butyl ether are about —24kJmoU (Iq) and —26.5 kJmol (g), respectively. From these, and the experimental enthalpy of formation of di-ferf-butyl peroxide, the enthalpies of formation of di-n-butyl peroxide are ca —333 kJmol (Iq) and —288 kJmol (g), wildly divergent from the reported values. 

As was the case for the alkyl hydroperoxides in reaction 4, the enthalpies of the oxy-gen/hydrocarbon double exchange reaction 8 for dialkyl peroxides are different depending on the classification of the carbon bonded to oxygen. For R = Me, Et and f-Bu, the liquid phase values are —4, 24.6 and 52.7 kJmoR, respectively, and the gas phase values are 0.1, 25.7 and 56.5 kJmoR, respectively. For the formal deoxygenation reaction 9, the enthalpies of reaction are virtually the same for dimethyl and diethyl peroxide in the gas phase, —58.5 0.6 kJ moR. This value is the same as the enthalpy of reaction of diethyl peroxide in the liquid phase, —56.0 kJ moR (there is no directly determined liquid phase enthalpy of formation of dimethyl ether). Because of steric strain in the di-ferf-butyl ether, the enthalpy of reaction is much less negative, but still exothermic, —17.7 kJmol (Iq) and —19.6 kJmol (g). 

The first variant works with isobutane as the hydroperoxide precursor, which is oxidized to TBHP by molecular oxygen. During the epoxidation of propene, TBHP is transformed to ferf-butanol, which is converted to methyl ferf-butyl ether. The second procedure employs ethylbenzene, which is oxidized by molecular oxygen to phenyl ethyl hydroperoxide, which transfers an oxygen to propene and so is reduced to phenylethanol. This by-product of the process is converted to styrene, a versatile bulk chemical. 

DO-IT has been used at several sites to treat benzene, toluene, ethyl benzene, and xylene (BTEX), methyl ferf-butyl ether (MTBE), and total petroleum hydrocarbons (TPH). According to the vendor, this technology may also be applied or modified to clean up any aerobically biodegradable contaminants in soil. 

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