Phase-transfer catalysis applied to the oxidation of nonaqueous phase trichloroethylene by potassium permanganate

Journal of Contaminant Hydrology

Volumn 44, Issue 2, 2000, Pages 185-201

  Seol, Yongkoo ^a   Schwartz, Franklin W ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Nonaqueous phase; Phase transfer catalyst; Potassium permanganate; Remediation; Trichloroethylene

Indexed keywords

CHLORIDE; GROUND WATER; PERMANGANATE POTASSIUM; TRICHLOROETHYLENE;

GROUNDWATER POLLUTION; NONAQUEOUS PHASE LIQUID; OXIDATION; REMEDIATION; TRICHLOROETHYLENE;

ARTICLE; CATALYSIS; DEGRADATION; OXIDATION; PRIORITY JOURNAL; SOLUBILITY;

EID: 0033853602     PISSN: 01697722     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0169-7722(00)00093-0     Document Type: Article

References (40)

1. Bränström A. Preparative Ion Pair Extraction. 1976;Apotekarsocieteeten/Hassle, Lakemedel, Sweden. 168 pp.
2. Bränström A. Principles of phase-transfer catalysis by quaternary ammonium salts. Adv. Phys. Org. Chem. 15:1977;267.
3. Cotlove E. An instrument and method for automatic, rapid, accurate and sensitive titration of chloride in biologic samples. J. Lab. Clin. Med. 51:1958;461-468.
4. Dehmlow E.V., Dehmlow S.S. Phase Transfer Catalysis. 1983;Verlag Chemie, Weinheim, Germany. 386 pp.
5. Freeman F., Kappos J.C. Permanganate ion oxidations: 15. Additional evidence for formation of soluble (colloidal) manganese dioxide during the permanganate ion oxidation of carbon-carbon double bonds in phosphate-buffered solutions. J. Am. Chem. Soc. 107(23):1985;6628-6633.
6. Glaze W.H., Kang J.K. Advanced oxidation processes for treating groundwater contaminated with TCE and PCE; laboratory studies. J. AWWA. 80:1988;57-63.
7. Harris J.M., Case M.G. Poly(ethylene glycol) ethers as recoverable phase-transfer agents in permanganate oxidations. J. Am. Chem. Soc. 48:1983;5390-5392.
8. Johnson R.L., Pankow J.F. Dissolution of dense chlorinated solvents into groundwater: 2. Source functions for pools of solvent. Environ. Sci. Technol. 26(2):1992;896-901.
9. Karaman H., Barton R.J., Robertson B.E., Lee D.G. Preparation and properties of quaternary ammonium and phosphonium permanganates. J. Org. Chem. 49:1984;4509-4516.
10. Kile D.E., Chiou C.T. Water solubility enhancements of DDT and trichlorobenzene by some surfactants below and above the critical micelle concentration. Environ. Sci. Technol. 23(7):1989;832-838.
11. Lampman G.M., Sharpe S.D. A phase transfer catalyzed permanganate oxidation preparation of vanillin from isoeugenol acetate. J. Chem. Educ. 60(6):1983;503-504.
12. Landini D., Maia A., Rampoldi A. Stability of quaternary onium salts under phase-transfer conditions in the presence of aqueous alkaline solutions. J. Org. Chem. 51:1986;3187-3192.
13. Lee D.G., Brownridge J.B. The oxidation of cinnamic acid by permanganate ion. Spectrophotometric detection of an intermediate. J. Am. Chem. Soc. 95:1973;3033-3034.
14. Makosza M., Bialecka E. A simple preparation of anhydrous tetraalkyammonium salts. Synth. Commun. 6(4):1976;313-318.
15. Mata-Perez F., Perez-Benito J.F. Identification of the product from the reduction of permanganate ion by trimethylamine in aqueous phosphate buffers. Can. J. Chem. 63:1985;988-992.
16. Moroi Y., Noma H., Matura R. Solubilization of N-alkylphenothiazine in aqueous anionic surfactant micelles. J. Phys. Chem. 87(5):1983;872-876.
17. Ogito T., Mochizuki K. Homogeneous permanganate oxidation in non-aqueous organic solution. Selective oxidations of olefins into 1,2-diols or aldehydes. Chem. Lett. 1979;443-446.
18. Plumb R.H. The occurrence of appendix 1X organic constituents in disposal site groundwater. Ground Water Monit. Rev. 1991;157-165. (Spring).
19. Rao K.H., Rao M.B. Studies in phase transfer catalysis: Part-1. Permanganate oxidation. J. Indian Chem. Soc. 68:1991;132-134.
20. Rosen M.J. Surfactants and Interfacial Phenomena. 1978;Wiley, New York, NY.
21. Sala T., Sargent M.V. Tetrabutylammonium permanganate: an efficient oxidation for organic substrates. J.C.S. Chem. Commun. 1978;253-254.
22. Sam D.J., Simmons H.E. Crown polyether chemistry. Potassium permanganate oxidation in benzene. J. Am. Chem. Soc. 94(11):1972;4024-4025.
23. Schnarr M.et al. Laboratory and controlled field experiments using potassium permanganate to remediate trichloroethylene and perchloroethylene DNAPLSs in porous media. J. Contam. Hydrol. 29:1998;205-224.
24. Schwartz A.M., Perry J.W. Surface active agents - their chemistry and technology. 1978;Robert E. Krieger Publishing, Huntington, NY.
25. Simandi I., Jaky M. Nature of the detectable intermediate in the permanganate oxidation of trans-cinnamic acid. J. Am. Chem. Soc. 98:1976;1995-1997.
26. Starks C.M. Phase-transfer catalysis: I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts. J. Am. Chem. Soc. 93(1):1971;195-199.
27. Starks C.M. Modern perspectives on the mechanisms of phase-transfer catalysis. Halpern M.E. Phase-Transfer Catalysis; Mechanism and Synthesis. ACS Symposium Series. vol. 659:1997;10-28 ACS, Washington, DC.
28. Starks C.M., Liotta C.L., Halpern M. Phase-Transfer Catalysis; Fundamentals, Applications, and Industrial Perspectives. 1994;668 Chapman & Hall, New York, NY.
29. Stewart R. Oxidation by permanganate. Wiberg K.B. Oxidation in Organic Chemistry, Part A. 1965;1068 Academic Press, New York, NY.
30. Tomoi M., Ford W.T. Mechanisms of polymer-supported catalysis: 1. Reaction of 1-bromeoxtane with aqueous sodium cyanide catalyzed by polystyrene-bound benzyltri-n-butylphosphonium ion. J. Am. Chem. Soc. 103:1981;3821-3827.
31. Ugelstad J., Ellingsen T., Berge A. The effect of the solvent on the reactivity of potassium and quaternary ammonium phenoxides in nucleophilic substitution reactions. Acta Chem. Scand. 20:1966;1593-1598.
32. Vella P.A., Veronda B. Oxidation of trichloroethylene; comparison of potassium permanganate and Fenton's reagent. The Third International Symposium on Chemical Oxidation Technology for the Nineties, Nashville, TN. 1992.
33. Vogel T.M., Criddle C.S., McCarty P.L. Transformation of halogenated aliphatic compounds. Environ. Sci. Technol. 21:1987;722-736.
34. 4 oxidation of olefins to cis-1,2-glycols by use of phase transfer catalysis. Terahedron Lett. 48:1972;4907-4908.
35. Westrick J.J., Mello J.W., Thomas R.F. The groundwater supply survey. J. AWWA. 1984;52-59. (May).
36. Wiberg K.B., Deutch C.J., Rocek J. Permanganate oxidation of crotonic acid. Spectrometric detection of an intermediate. J. Am. Chem. Soc. 95:1973;3034-3035.
37. Wilson J.L., Conrad S.H. Is physical displacement of residual hydrocarbon a realistic possibility in aquifer restoration? Proc. of the NWWA.API Conference on Petroleum Hydrocarbon and Organic Chemicals in Groundwater - Prevention, Detection, and Restoration. 1984;274-298 National Water Well Association, Dublin, OH.
38. Yan, Y.E., 1998. Abiotic remediation of ground water contaminated by chlorinated solvents. PhD Thesis, The Ohio State University, 105 pp.
39. Yan Y.E., Schwartz F.W. Oxidative degradation and kinetics of chlorinated ethylenes by potassium permanganate. J. Contam. Hydrol. 37:1999;343-365.
40. Zhang, H., Schwartz, F.W., 2000. Simulations of oxidative treatment of chlorinated compounds by permanganate. submitted for publication.