Technological aspects of the synthesis of 2,4-dichlorophenol

• Autorzy: Białek A. , Moszczyński W.
• Języki publikacji: EN

Abstrakty

EN

The main factors influencing the selectivity of chlorophenols synthesis were described. The loss of raw materials and the composition of wastes obtained in a conventional technology of 2,4-D production based on 2,4-dichlorophenol (2,4-DCP) of the 89% purity were presented. The influence of some homogenous catalysts on the selectivity of 2,4-dichlorophenol obtained in phenol and chlorine reaction was examined. Using the combined catalyst enables to chlorinate selectively the monochlorophenols to 2,4-DCP without an undesirable increasing of the 2,6-dichlorophenol and 2,4,6-trichlorophenol contents. The catalyst transformations during the reaction of phenol chlorination were investigated and the method of its elimination after the reaction was elaborated.

Słowa kluczowe

EN

2,4-dichlorophenol; chlorination; catalyst; dioxine; 2,4-dichlorophenoxyacetic acid

PL

2,4-dichlorofenol; chlorowanie; katalizator; dioksyny; kwas 2,4-dichlorofenoksyoctowy

• Wydawca: West Pomeranian University of Technology. Publishing House
• Czasopismo: Polish Journal of Chemical Technology
• Rocznik: 2009
• Tom: Vol. 11, nr 2
• Strony: 21--30
• Opis fizyczny: Bibliogr. 35 poz., rys., tab.

Twórcy

autor

Białek A.

autor

Moszczyński W.

• Institute of Industrial Organic Chemistry, (IPO), ul. Annopol 6, 02-236 Warszawa,

Bibliografia

• 1. Mueller, F. & Caillard, L. (1986). Ullmann's Encyclopedia of Industrial Chemistry (Vol A7). Chlorophenols. Verlag Chemie, Weinheim / Bergstr.
• 2. Desmurs, J.R. & Ratton, S. (2000). Kirk-Othmer Encyklopedia of Chemical Technology. Chlorophenols. John Wiley & Sons, Inc.
• 3. Moszczyński, W., Białek, A., Białek, E. & Rippel, B. (2008). Development of 2,4-D technology in Poland. Przem. Chem. 87(7), 757-759.
• 4. Cieślak, M., Koperska, M., Żołędziowska & J., Kosińska K. (1969). Unpublished Report No. 7/19/21. IPO Library Warsaw.
• 5. Cattabeni, F., Cavallaro, A. & Galli, G. (1978). Dioxyne, technological and chemical aspect. SP Medical and Scientific Books, New York, London.
• 6. Council Directive of 15 July 1991 Concerning the placing of plant protection products on the market (91/414/EEC), OJ L 230,19.8.1991, p.1
• 7. Watson, W.D. (1985). Regioselective Para Chlorination of Activated Aromatic Compounds. J. Org. Chem. 50, 2145-48.
• 8. Joester, M.D. & Shaad, I.J. (1974). Hydrogen Bonding. Marcel Delker, New York.
• 9. Belany, L.J. (1958). The Infra-red Spectra of Complex Molecules (2nd ed). Wiley, New York.
• 10. Caujolle, F., Fauran, F. & Quan, D., Q., (1968) On the bond between bovine serum albumin and 6-monoalkylated metacresols. C R Acad Sci Hebd Seances Acad Sci D. 267 (25):2213-2215.
• 11. Watson, W.D. (1974). Chlorination of Phenols with Chlorine and tert-Butyl Hypochlorite. A Comparison. J. Org. Chem., 39(8), 1160-1164.
• 12. Ogata, Y., Kimura, M., Kondo, Y., Katoh, H. & Chen, F-C. (1984). J.Chem.Soc. P.T.II. 1984, 451-453.
• 13. Szekely, I. (1982). Ger. Pat. 3318791. (to CIBA-GEIGY).
• 14. Besson, B. & Desmurs, J.R. (1989) U.S. Pat. 4855513. (to Rhône-Poulenc).
• 15. Moszczyński, W. (1998). The research for synthesis and production of 4-chloro-2-methylphenoxyacetic acid (MCPA). Prace Naukowe Instytutu Przemysłu Organicznego "Organika"
• 16. Drahonowsky, J. & Vacek, Z. (1971). Collect. Czech. Chem. Comm. 36, 3431-3440.
• 17. Watson, W.D. (1976). The regioselective para-chlorination ot 2-methylphenol. Tetrahedron Lett. 30, 2591-2594.
• 18. Ratton, S. (1987). Fr. Pat. 2584068, (to Rhone Poulenc Spec. Chim.).
• 19. Shelton, F.J., Wetzel, W.H., Wilkinson, J.L. & Goodwin. R.J. (1977). U.S. Pat. 4160114 (to Reichhold Chemicals).
• 20. Tzimas, M. (1998). Eur. Pat. 0866048. (to UNIV. WALES SWANSEA).
• 21. Tzimas, M., Smith, D.E. and co-workers (1998). Eur. Pat. 0866049 (to UNIV. WALES SWANSEA).
• 22. Moszczyński, W., Białek, A., Białek, E., Listopadzki, E. & Rippel, B. (2007). Pl. Pat. 197863. (to IPO and Rokita-Agro SA.)
• 23. Bukowska, B., Rychlik, B., Krokosz A. & Michałowicz J. (2008). Phenoxyherbicides induce production of free radicals in human erythrocytes: Oxidation of dichlorodihydrofluorescin and dihydrodamine 123 by 2,4-D-Na and MCPA-Na. Food Chem. Toxicol, 46, 1, 359-367. DOI: 10.1016/j.fct.2007.08.011
• 24. Abrahamsson, K. & Xie, T., M. (1983). J. Chromatog. 279, 199-208.
• 25. Kempf, H., Chamard, A., Desmurs, J. R., Dananche, J. & Bauer, G. (1987). Poster Iieres Journées d'Electrochimie, Dijon, France.
• 26. Ratton, S. & Desmurs, J.R. (1986). Fr. Pat. 2601001 (to Rhône-Poulenc Chimie).
• 27. Ratton, S. (1985). Brit. Pat. 2177396 (to Rhône-Poulenc Specialties Chimiques).
• 28. Besson, B., Desmurs, J.R. & Jouve, I. (1987). Eur. pat. 283411. (to Rhône-Poulenc Chimie).
• 29. Desmurs, J.R. & Ratton, S. (1989). U.S. Pat. 4853153 (to Rhone Poulenc Chimie).
• 30. Perwunina, R.L., Samsonow, D.P. & Rakhmanowa, T.V. (1992). 2,3,7,8-Tetrachloro-p-dioksin in Russian Environmental Samples, Materials DIOX W92, 173-176.
• 31. Standarized Toolkit for Identification and Quantification of Dioxn and Furan Releases, 1-est edition, (2003), UN Environment Programm, UN EP Chemicals, Geneva.
• 32. Boddington, M.J., Gilman, A.P. & Newhook R.C., (1990). Polichlorinated Dibenzodioxins and Dibenzofurans. Canadian Environmental Protection Act. List Assentment Report No.1.
• 33. Thompson, L.R. & Kearney, J.K. (1981). U.S. Pat. 4272636 (to Dow Chemical Co.)
• 34. Moszczyński, W., Połeć, I., Białek, A., Białek, E., Listopadzki, E. & Rippel, B. (2003). Unpublished Report No 6T 090034 2002/C05821, Stage No 1B, IPO Library Warsaw.
• 35. Moszczyński, W., Białek, A. Białek, E., Rippel, B., Okulewicz, Z., Dancewicz, G. (2006). Pl. Pat. Appl. P-377671. (to IPO and Rokita-Agro SA.)