Advanced oxidation and reduction process chemistry of methyl tert-butyl ether (MTBE) reaction intermediates in aqueous solution: 2-Methoxy-2-methyl-propanal, 2-methoxy-2-methyl-propanol, and 2-methoxy-2-methyl-propanoic acid

Chemosphere

Volumn 77, Issue 10, 2009, Pages 1352-1357

  Mezyk, Stephen P ^a   Rance Hardison, D ^b   Song, Weihua ^c   O'Shea, Kevin E ^c   Bartels, David M ^d   Cooper, William J ^e  

^a CALIFORNIA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

^c FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^d UNIVERSITY OF NOTRE DAME   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

AOP degradation; Hydroxyl radical; MTBE; Oxidation; Radical kinetics; Reduction

Indexed keywords

ATOMS; DEGRADATION; ETHERS; HYDRATION; HYDROGEN; OXIDATION; RATE CONSTANTS; REDUCTION;

DEGRADATION PATHWAYS; DEGRADATION PRODUCTS; HYDROXYL RADICAL OXIDATIONS; HYDROXYL RADICALS; INTERMEDIATE SPECIE; METHYL TERT BUTYL ETHER; MTBE; RADICAL KINETICS;

REACTION INTERMEDIATES;

2 METHOXY 2 METHYL PROPANAL; 2 METHOXY 2 METHYL PROPANOIC ACID; 2 METHOXY 2 METHYL PROPANOL; HYDROGEN; HYDROXYL RADICAL; PROPANOL; PROPIONALDEHYDE; PROPIONIC ACID DERIVATIVE; TERT BUTYL METHYL ETHER; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; HYDROGEN ISOTOPE; HYDROXYL RADICAL; MTBE; OXIDATION; REACTION KINETICS; REDUCTION; TEMPERATURE GRADIENT;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DEGRADATION KINETICS; MOLECULAR INTERACTION; OXIDATION REDUCTION REACTION; PULSE RADIOLYSIS; RADICAL REACTION; REACTION TIME; ROOM TEMPERATURE;

EID: 71149121759     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2009.09.029     Document Type: Article

References (32)

1. Acero J.L., Haderlein S.B., Schmidt T.C., Suter M.J.-F., and von Gunten U. MTBE oxidation by conventional ozonation and the combination ozone/hydrogen peroxide: efficiency of the processes and bromate formation. Env. Sci. Technol. 35 (2001) 4252-4259
2. Adams G.E., Boag J., Currant J., and Michael B.D. In: Ebert M., Keene J.P., Swallow A.J., and Baxendale J.H. (Eds). Pulse Radiolysis (1965), Academic Press, New York 131-143
3. Bartels D.M., and Mezyk S.P. EPR Measurement of the reaction of atomic hydrogen with bromide and iodide in aqueous solution. J. Phys. Chem. 97 (1993) 4101-4105
4. Bartels D.M., Craw M.T., Han P., and Trifunac A.D. Hydrogen/deuterium isotope effects in water radiolysis. 1. The mechanism of chemically induced dynamic electron polarization generation in spurs. J. Phys. Chem. 93 (1989) 2412-2421
5. Buckley T.J., Prah J.D., Ashley D., Zweider R.A., and Wallace L.A. Body burden measurements and models to assess inhalation exposure to methyl tertiary butyl ether (MTBE). J. Air Waste Manage. Assoc. 47 (1997) 739-752
6. Buxton G.V., and Stuart C.R. Re-evaluation of the thiocyanate dosimeter for pulse radiolysis. J. Chem. Soc., Faraday Trans. 91 (1995) 279-281
7. -) in aqueous solution. J. Phys. Chem. Ref. Data 17 (1988) 513-886
8. Carter J.M., Grady S.J., Delzer G.C., Koch B., and Zogorski J.S. Occurrence of MTBE: and other gasoline oxygenates in CWS source waters. J. Am. Water Works Assoc. 98 (2006) 91-104
9. 2 treatment of methyl tert-butyl ether in contaminated waters. Env. Sci. Technol. 34 (2000) 659-662
10. Cooper W.J., Cramer C.J., Martin N.H., Mezyk S.P., O'Shea K.E., and von Sonntag C. Free radical mechanisms for the treatment of methyl tert-butyl ether (MTBE) via advanced oxidation/reductive processes in aqueous solutions. Chem. Rev. 109 (2009) 1302-1345
11. Eibenberger J., Schulte-Frohlinde D., and Steenken S. One-electron oxidation of α-monoalkoxyalkyl radicals by tetranitromethane via an intermediate adduct. Influence of the radical structure on the rate of decomposition of the adduct. J. Phys. Chem. 84 (1980) 704-710
12. Hardison D.R., Cooper W.J., Mezyk S.P., and Bartels D.M. The free radical chemistry of tert-butyl formate: Rate constants for hydroxyl radical, hydrated electron and hydrogen atom reaction in aqueous solution. Radiat. Phys. Chem. 65 (2002) 309-315
13. Kirchstetter T.W., Singer B.C., Harley R.A., Kendell G.R., and Chan W. Impact of oxygenated gasoline use on California light-duty vehicle emissions. Env. Sci. Technol. 30 (1996) 661-670
14. Koehler G., Solar S., Getoff N., Holzwarth A.R., and Schaffner K. Relationship between the quantum yields of electron photoejection and fluorescence of aromatic carboxylate anions in aqueous solution. J. Photochem. 28 (1985) 383-391
15. Mehlman M.A. Dangerous and cancer-causing properties of products and chemicals in the oil refining and petrochemical industry: Part XV. Health hazards and health risks from oxygenated automobile fuels (MTBE): Lessons not heeded. Int. J. Occup. Med. Toxicol. 4 (1995) 219-236
16. Mezyk S.P., and Bartels D.M. Absolute rate constant measurements for the reaction of atomic hydrogen with acetone, 2-butanone, propionaldehyde, and butyraldehyde in aqueous solution. Can. J. Chem. 72 (1994) 2516-2520
17. 7 in aqueous solution. J. Phys. Chem. A 101 (1997) 1329-1333
18. Mezyk S.P., Jones J., Cooper W.J., Tobien T., Nickelsen M.G., Adams J.W., O'Shea K.E., Bartels D.M., Wishart J.F., Tornatore P.M., Newman K.S., Gregorie K., and Weidman D.J. Radiation chemistry of methyl tert-butyl ether in aqueous solution. Env. Sci. Technol. 38 (2004) 3994-4001
19. 2 photocatalysis of gasoline oxygenates. Kinetic parameters and effects of catalyst types and loading on degradation of MTBE. In: Oxygenates in Gasoline, Diaz, A.F., Drogos, D. L. (Eds.), ACS Symposium Series No. 799, American Chemical Society, Washington, DC, p. 165.
20. Pankow J.F., Rathbun R.E., and Zogorski J.S. Calculated volatilization rates of fuel oxygenate compounds and other gasoline-related compounds from rivers and streams. Chemosphere 33 (1996) 921-937
21. Park H.-R., and Getoff N. Radiolysis of aqueous ethanol in the presence of CO, Z. Naturforsch., A, Phys. Sci. 47A (1992) 985-991
22. Pimblott S.M., and LaVerne J.A. Yields of hydroxyl radical and hydrated electron scavenging reactions in aqueous solutions of biological interest. Radiat. Res. 135 (1993) 16-23
23. Pontius F.W. Health Advisory issued for methyl tertiary butyl ether. J. Amer. Water Works Assoc. 90 (1998) 17
24. Spinks J.W.T., and Woods R.J. Introduction to Radiation Chemistry. third ed. (1990), John Wiley and Sons Inc., New York
25. Squillace P.J., Zogorski J.S., Wilber W.G., and Price C.V. A preliminary assessment of the occurrence and possible sources of MTBE in groundwater in the United States, 1993-1994. Env. Sci. Technol. 30 (1996) 1721-1730
26. 2 process. Env. Sci. Technol. 34 (2000) 650-658
27. Suflita J.M., and Mormille M.R. Anaerobic biodegradation of known and potential gasoline oxygenates in the terrestrial subsurface. Env. Sci. Technol. 27 (1993) 976-978
28. von Sonntag C., and Schuchmann H.-P. Peroxyl radicals in aqueous solution. In: Alfassi Z.B. (Ed). Peroxyl radicals (1997), John Wiley and Sons Ltd, New York 173
29. Wagler J.L., and Malley Jr. J.P. The removal of methyl tertiary-butyl ether from a model groundwater using UV/peroxide oxidation. J. New Engl. Water Works Assoc. 108 (1994) 236-260
30. Whitman, K., Lyons, S., Miller, R., Nett, D., Treas, P., Zante, A., Fessenden, R.W., Thomas, M.D., Wang, Y. 1996. Linear accelerator for radiation chemistry research at Notre Dame, In: Proceedings of the '95 Particle Accelerator Conference and International Conference on High Energy Accelerators, TX, USA.
31. Wu T., Cruz V., Mezyk S.P., Cooper W.J., and O'Shea K.E. Gamma radiolysis of methyl t-butyl ether: A study of hydroxyl radical mediated reaction pathways. Rad. Phys. Chem. 65 (2002) 335-341
32. Zona R., Solar S., Getoff N., Sehested K., and Holcman J. Reactivity of H atoms and hydrated electrons with chlorobenzoic acids. J. Rad. Phys. Chem. 77 (2008) 162-168