Error message

  • Deprecated function: Unparenthesized `a ? b : c ? d : e` is deprecated. Use either `(a ? b : c) ? d : e` or `a ? b : (c ? d : e)` in include_once() (line 1439 of /home/science2016/public_html/includes/bootstrap.inc).
  • Deprecated function: Array and string offset access syntax with curly braces is deprecated in include_once() (line 3557 of /home/science2016/public_html/includes/bootstrap.inc).

Kinetics and Mechanism of the Ozone Reaction with Alcohols, Ketones, Ethers and Hydroxybenzenes

Slavcho Rakovsky1, Metody Anachkov1, Mikhail Belitskii2 and Gennady Zaikov
Affiliation: 
1 Institute of Catalysis, Bulgarian Academy of Sciences, 11, Acad. G. Bonchev str., 1113 Sofia, Bulgaria; rakovsky@ic.bas.bg 2 N.M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4, Kosygin str., 119334 Moscow, , Russia
DOI: 
https://doi.org/10.23939/chcht10.04si.531
AttachmentSize
PDF icon full_text.pdf288.15 KB

Keywords:

Abstract: 
The review, based on 92 references, is focused on degradation of organics by ozonation and it comprises various classes of oxygen-containing organic compounds – alcohols, ketones, ethers and hydroxybenzenes. The mechanisms of a multitude of ozone reactions with these compounds in organic solvents are discussed in details, presenting the respective reaction schemes. The corresponding kinetic parameters are given and some thermodynamic parameters are also listed. The dependences of the kinetics and the mechanism of the ozonation reactions on the structure of the compounds, on the medium and on the reaction conditions are revealed. Various possible applications of ozonolysis are specified and discussed. All these reactions have practical importance for the protection of the environment.
References: 

[1] Razumovskii S., Rakovsky S., Shopov D. and Zaikov G.: Ozone i ego Reakcii s Organicheskimi Soedineniyami. Publ. House of the Bulgarian Academy of Sci., Sofia 1983.

[2] Bailey P.: Ozonation in Organic Chemistry, v. 2. Academic Press: New York 1982.

[3] Waters W., Rollin A., Bardwell C. et al.: J. Org. Chem., 1976, 41, 889.
https://doi.org/10.1021/jo00867a033

[4] Otal E., Mantzavinos D., Delga M. et al.: J. Chem. Techn. and Biotechn., 1997, 70, 147.
https://doi.org/10.1002/(SICI)1097-4660(199710)70:2<147::AID-JCTB747>3.0.CO;2-3

[5] Benitez F., Beltran-Heredia J., Acero J. and Pinilla A.: J. Chem. Techn. and Biotechn., 1997, 70, 253.
https://doi.org/10.1002/(SICI)1097-4660(199711)70:3<253::AID-JCTB770>3.0.CO;2-H

[6] Amalric L., Guillard C. and Pichat P.: Research on Chem. Intermed., 1995, 21, 33.
https://doi.org/10.1163/156856795X00053

[7] Heinzle E., Stockinger H., Stern M. et al.: J. Chem. Techn. and Biotechn., 1995, 62, 241.
https://doi.org/10.1002/jctb.280620306

[8] Beltran F., Alvarez P., Legube B. and Allemane H.: ibid., 272.

[9] Lee M., Arai H. and Miyata T.: Chem. Lett., 1994, 6, 1069.
https://doi.org/10.1246/cl.1994.1069

[10] Benko E., Kovaleva V., Mamleeva N. et al.: Zh. Fisich. Khimii, 1994, 68, 1964.

[11] Artemev Y., Artemeva M., Vinogradov M. and Ilika T.: Rus. J. Appl. Chem., 1994, 67, 1354.

[12] Scheuer C., Wimmer B., Bischof H. et al.: J. Chromatography A, 1995, 706, 253.
https://doi.org/10.1016/0021-9673(95)00005-8

[13] Hoger B., Gilbert E. and Eberle S.: Vom Wasser, 1993, 80, 187.

[14] Ruck W.: Vom Wasser, 1993, 80, 253.

[15] Gab S., Turner W., Wolff S. et al.: Atmosph. Environ., 1995, 29, 2401.
https://doi.org/10.1016/1352-2310(95)00166-V

[16] Takeuchi K., Fushimi C., Nakamura K. and Ibusuki T.: Bunseki Kagaku, 1993, 42, 625.
https://doi.org/10.2116/bunsekikagaku.42.10_625

[17] Pan G., Chen C., Gratzl J. and Chang H.: Research on Chem. Intermed., 1995, 21, 205.
https://doi.org/10.1007/BF03052254

[18] Wada H., Naoi T. and Kuroda Y. : Nippon Kagaku Kaishi, 1995, 4, 306.
https://doi.org/10.1246/nikkashi.1995.306

[19] Marco A., Chamarro E. and Esplugas S.: Afinidad, 1994, 51, 265.

[20] Starek J., Zukal A. and Rathousky J.: Carbon, 1994, 32, 207.
https://doi.org/10.1016/0008-6223(94)90184-8

[21] Mvula E. and von Sonntag C.: Org. & Biomol. Chem., 2003, 1, 1749.
https://doi.org/10.1039/b301824p

[22] Ben'ko E., Bokova M., Pryakhin A. and Lunin V.: Rus. J. of Phys. Chem., 2003, 77, 739.

[23] Ramseier M. and von Gunten U.: Ozone Sci. & Eng., 2009, 31, 201.
https://doi.org/10.1080/01919510902740477

[24] Valsania M., Fasano F., Richardson S. and Vincenti M.: Water Research, 2012, 46, 2795.
https://doi.org/10.1016/j.watres.2012.02.040

[25] Rakovsky S. and Cherneva D.: Int. J. Chem. Kinetics, 1990, 22, 321.
https://doi.org/10.1002/kin.550220402

[26] Rakovsky S., Cherneva D., Shopov D. and Razumovskiy S.: Commun. Dept. of Chem., Bulg. Acad. Sci., 1976, 9, 711.

[27] Rakovsky S. and Cherneva D.: Oxidat. Commun., 1989, 12, 108.

[28] Rakovsky S., Kulak L., Kuramshin E. et al.: Commun. Dept. of Chem., Bulg. Acad. Sci., 1989, 22, 722.

[29] Rakhmankulov D., Zlotsky S., Rudnik L. et al.: ibid, 652.

[30] Anachkov M., Rakovsky S., Stoyanov A. and Fotty R.: Thermochemica Acta, 1994, 237, 213.
https://doi.org/10.1016/0040-6031(94)85202-2

[31] Rakovsky S., Cherneva D. and Deneva M.: Int. J. Chem. Kinetics, 1995, 27, 153.
https://doi.org/10.1002/kin.550270206

[32] Rakovsky S., Cherneva D., Deneva M. and Ershov V.: Oxidat. Commun., 1997, 20, 169.

[33] Rakovsky S., Sheldon R. and Rantwijk F.: Oxidat. Commun., 1996, 19, 482.

[34] Zaikov G. and Rakovsky S.: Ozonation of Organic & Polymer Compounds. iSmithers, Smithers Rapra, Shawbury, Shreswsbury, Shropshire, SY4 4NR, UK, 2009.

[35] Popova D., Rakovsky S. and Anachkov M.: Oxidat. Commun., 2007, 30, 529.

[36] Eyring H., Lin S.H. and Lin S.M.: Osnovy Khimicheskoi Kinetiki. Mir, Moskwa 1983.

[37] Rozovskii A.: Heterogennye Khimicheskie Reakcii (Kinetika i Macrokinetika). Nauka, Moskwa 1980.

[38] Rozenberg M. and Brun E.: Teor. Osnovy Khim. Techn., 1990, 24, 198.

[39] Denisov E., Mitskevich N. and Agabekov V.: Mechanism of Liquid-Phase Oxidation of Oxygen Containing Compounds. Science and Technique Publishing House, Minsk 1975.

[40] Whiting M., Bolt A. and Parish J.: [in:] Mayo F. (Ed.), Oxidation of Organic Compounds, v. III. ACS, Washington DC 1968, 4-14.

[41] Williamson D. and Cvetanovich R.: J. Am. Chem. Soc., 1970, 92, 2949.
https://doi.org/10.1021/ja00713a005

[42] Gerchikov A., Kuznetzov E. and Denisov E.: Kinetika i Kataliz, 1970, 15, 109.

[43] Shereshovetz V., Shafikov N. and Komissarov V.: Kinetika i Kataliz, 1980, 21, 1596.

[44] Shafikov N., Gusmanov A., Zimin Yu. and Komissarov V.: Kinetika i Kataliz, 2002, 43, 799.

[45] Gerchikov A., Zimin Yu., Trukhanova N. and Evgrafov V.: React. Kinet. Catal. Lett., 1999, 68, 257.
https://doi.org/10.1007/BF02475510

[46] Borodin A. and Razumovskii S.: Kinetika i Kataliz, 2009, 50, 3385.

[47] Rakovsky S.: PhD thesis, Institute of Chemical Physics, Academy of Science of the USSR, Moscow 1975.

[48] Kondratiev V. (Ed.): Energiya Sviazi, Ionizacionnyi Potencial i Elektronoe Srodstvo. Nauka, Moskwa 1974.

[49] Gordon A. and Ford R.: Spravochnik Khimika. Mir, Moskwa 1976.

[50] Eiring G., Lin S.G. and Lin S.M.: Nachala Khimicheskoi Kinetiki. Mir, Moskwa 1983.

[51] Karadakov K. and Rakovsky S.: Calculation of Pre-exponents ver.1.0, (Software) Copyright, 1987, based on the Howbert J., Software: The Molecular Animator, vers. 1-3, Copyright, 1983.

[52] Thiel W.: Software, IBM, Program MNDOC, QCPE ver., Fachbereich Physikalische Chemie der Philipps-Universitat, auf den Zahbergen, D-3550, Marburg, Germany, based on Dewar M. and Thiel W.: J. Am. Chem. Soc., 1977, 99, 4899.

[53] Gerchikov A., Komissarov V., Denisov E. and Kochemassov G.: Kinetika i Kataliz, 1972, 13, 1126.

[54] Gerchikov A., Komissarov V. and Denisov E.: Kinetika i Kataliz, 1974, 15, 230.

[55] Gerchikov A., Komissarov V., Galimova L. and Denisov E.: Doklady Akad. Nauk SSSR, 1973, 213, 881.

[56] Korotkova N., Syroezhko A. and Proskuryakov V.: Zh. Prikladnoi Khimii, 1981, 54, 885.

[57] Komissarov V., Galimova L. and Denisov E.: Kinetika i Kataliz, 1974, 15, 1063.

[58] Syroezhko A., Korotkova N., Vihorev A. and Proskuryakov V.: Zh. Prikladnoi Khimii, 1978, 15, 2562.

[59] Barton D. and Li V. (Eds.): Obshaya Organicheskaya Khimiya, v. 2. Khimiya, Moskwa 1982.

[60] House H. and Benjamin W. (Eds.): Modern Synthetic Reactions; 2nd edn. Menlo Park, California 1972.

[61] Zabicky J. (Ed.): The Chemistry of the Carbonyl Group. Interscience Publishers, London 1970.

[62] Alcais P. and Brouillard R.: J. Chem. Soc. – Perkin II, 1972, 1214.
https://doi.org/10.1039/P29720001214

[63] von Balo L.: Annalen der Chemie, 1866, 140, 348.
https://doi.org/10.1002/jlac.18661400315

[64] Berthlot M.: Comptes Rendus, 1881, 92, 895.

[65] Harries V.: Annalen der Chemie, 1905, 343, 311.
https://doi.org/10.1002/jlac.19053430209

[66] Fischer F.G. Annalen der Chemie 1929, 476, 233.
https://doi.org/10.1002/jlac.19294760112

[67] Bailey P.: Chem. Rev., 1958, 58, 925.
https://doi.org/10.1021/cr50023a005

[68] Price C. and Tumolo A.: J. Am. Chem. Soc., 1964, 86, 4691.
https://doi.org/10.1021/ja01075a033

[69] Ericson R., Bakalik D., Richards C. and Seanlon M.: J. Org. Chem., 1966, 31, 461.
https://doi.org/10.1021/jo01340a026

[70] Stary F., Emge D. and Murray R.: J. Am. Chem. Soc., 1976, 98, 1880.
https://doi.org/10.1021/ja00423a039

[71] Giamalva D., Church D. and Pryor W.: J. Am. Chem. Soc., 1986, 108, 7678.
https://doi.org/10.1021/ja00284a035

[72] Pryor W., Ohto N. and Church D.: J. Am. Chem. Soc., 1983, 105, 3614.
https://doi.org/10.1021/ja00349a044

[73] Hoigne J. and Bader H.: Water Research, 1983, 17, 173.
https://doi.org/10.1016/0043-1354(83)90098-2

[74] Hoigne J. and Bader H.: ibid., 185.

[75] Hoigne J., Bader H., Haag W. and Staehlin J.: Water Research, 1985, 19, 993.
https://doi.org/10.1016/0043-1354(85)90368-9

[76] Kuramshin E., Ivashov U., Zlotskii S. and Rahmankulov D.: Izv. Vysshikh Uchebnykh Zavedenii, Khimia i Khim. Techhn., 1984, 27, 13.

[77] Gurol M. and Nekouinaini S.: Ind. & Eng. Chem. Fundamentals, 1984, 23, 54.
https://doi.org/10.1021/i100013a011

[78] Bernatek E. and Frangen C.: Acta Chemica Scandanavica, 1961, 15, 471.
https://doi.org/10.3891/acta.chem.scand.15-0471

[79] Bernatek E., Moskeland J. and Valen K.: ibid., 1454.

[80] Bernatek E. and Frangen C.: Acta Chemica Scandanavica, 1962, 16, 2421.
https://doi.org/10.3891/acta.chem.scand.16-2421

[81] Bernatek E. and Vincze A.: Acta Chemica Scandanavica, 1965, 19, 2007.
https://doi.org/10.3891/acta.chem.scand.19-2007

[82] Jarret M., Bermond A. and Ducauze C.: Analysis, 1983, 14, 185.

[83] Razumovskii S., Nikiforov G., Globenko G. et al.: Neftekhimia, 1972, 12, 376.

[84] Konstantinova M., Razumovskii S. and Zaikov G.: Izvestiya Akad. Nauk SSSR, Ser. Khim., 1991, 324.

[85] Razumovskii S., Konstantinova M. and Zaikov G.: Izvestiya Akad. Nauk SSSR, Ser. Khim., 1992, 1203.

[86] Konstantinova M., Vol'eva V. and Razumovskii S.: Izvestiya Akad. Nauk SSSR, Ser. Khim., 1992, 1443.

[87] Hoigne J.: [in:] Hrubec J. (Ed.), The Handbookof Environmental Chemistry. Springer-Verlag: New York 1998, 5, 83.

[88] von Gunten U.: Water Research, 2003, 37, 1443.
https://doi.org/10.1016/S0043-1354(02)00457-8

[89] Pi Yu., Schumacher J. and Jekel M.: Water Research, 2005, 39, 83.
https://doi.org/10.1016/j.watres.2004.09.004

[90] Buffle M-O. and von Gunten U.: Environ. Sci. Techn., 2006, 40, 3057.
https://doi.org/10.1021/es052020c

[91] Yao C. and Haag W.: Water Research, 1991, 25, 761.
https://doi.org/10.1016/0043-1354(91)90155-J

[92] Weast R., Astle M. and Beyer W.: Handbook of Chemistry and Physics, 66th edn., CPC Press, Boca Raton, Filadelfia 1985-1986.