How to cite this paper
Safari, A & Zeynizadeh, B. (2015). Activated charcoal: a highly efficient promoter for selective oxidation of alcohols to aldehydes and ketones by K2S2O8 at solvent-free conditions.Current Chemistry Letters, 4(3), 111-118.
Refrences
1. B?ckvall J. -E. (2010) Modern Oxidation Methods, 2nd Ed, Wiley?VCH, Weinheim.
2. Tojo G., and Fernandez M. (2006) Oxidation of Alcohols to Aldehydes and Ketones, Springer, New York.
3. Sheldon R. A., and Kochi, J. K. (1981) Metal?Catalyzed Oxidations of Organic Compounds, Academic Press, New York.
4. Hudlicky M. (1990) Oxidations in Organic Chemistry, American Chemical Society, Washington, DC.
5. Corey E. J., and Suggs J. W. (1975) Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett., 16, 2647–2650.
6. Ley S. V., Norman J., Griffith W. P., and Marsden S. P. (1994) Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis, 639–666.
7. Fatiadi A. J. (1987) The classical permanganate ion: still a novel oxidant in organic chemistry. Synthesis, 85–127.
8. Firouzabadi H., and Mostafavipoor Z. (1983) Barium manganate. A versatile oxidant in organic synthesis. Bull. Chem. Soc. Jpn., 56, 914–917.
9. Lou J. -D., Wang M., Zhu L. -Y., and Fang Z. -G. (2003) Solvent free oxidation of alcohols catalyzed by KMnO4 adsorbed on Kieselguhr. Catal. Commun., 4, 647–649.
10. Fatiadi A. J. (1976) Active manganese dioxide oxidation in organic chemistry – Part I. Synthesis, 65–104.
11. Fatiadi A. J. (1976) Active manganese dioxide oxidation in organic chemistry – Part II. Synthesis, 133–167.
12. Taylor R. J. K., Reid M., Foot, J., and Raw S. A. (2005) Tandem oxidation processes using manganese dioxide: discovery, applications, and current studies. Acc. Chem. Res., 38, 851–869.
13. Lou J. -D., Ge J., Zou X. -N., Zhang C., Wang Q., and Ma Y. -C. (2011) Effective oxidation of alcohols with manganes dioxide supported on kieselguhr under heterogeneous conditions. Oxidat. Commun., 34, 361–365.
14. Mancuso A. J., Huang S. -L., and Swern D. (1978) Oxidation of long?chain and related alcohols to carbonyls by dimethyl sulfoxide activated by oxalyl chloride. J. Org. Chem., 43, 2480–2482.
15. Pfitzner K. E., and Moffatt J. G. (1963) A new and selective oxidation of alcohols. J. Am. Chem. Soc., 85, 3027–3028.
16. Parikh J. R., and Doering W. V. E. (1967) Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide. J. Am. Chem. Soc., 89, 5505–5507.
17. Mckillop A., and Young D. W. (1979) Organic synthesis using supported reagents ? part I. Synthesis, 401–422.
18. Fétizon M. (2009) Silver(I) carbonate on celite. In: Paquette L. A., Crich D., Fuchs P. L., and Molander G. A. (Eds) Encyclopedia of Reagents for Organic Synthesis, 2nd Ed, Wiley, Chichester.
19. Dess D. B., and Martin J. C. (1983) Readily accessible 12?I?5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 48, 4155–4156.
20. Frigerio M., and Santagostino M. (1994) A mild oxidizing reagent for alcohols and 1,2?diols: o-iodoxybenzoic acid (IBX) in DMSO. Tetrahedron Lett., 35, 8019–8022.
21. More J. D., and Finney N. S. (2002) A Simple and Advantageous Protocol for the Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX). Org. Lett., 4, 3001–3003.
22. Lee S. B., and Lee J. C. (2009) Oxidation of benzylic alcohols with iodine and lithium carbonate in ionic liquid. Bull. Korean Chem. Soc., 30, 3107–3108.
23. Saikia I., Chakraborty P., and Phukan P. (2009) A new metal?free protocol for oxidation of alcohols using N,N?dibromo?p?toluenesulfonamide. Arkivoc, xiii, 281–286.
24. Vocanson F., Guo Y. P., Namy J. L., and Kagan H. B. (1998) Dioxygen oxidation of alcohols and aldehydes over a cerium dioxide-ruthenium system. Synth. Commun., 28, 2577–2582.
25. Mardur S. P., and Gokavi G. S. (2010) Selective oxidation of alcohols to aldehydes by hydrogen peroxide using hexamolybdochromate(III) as catalyst. J. Iran. Chem. Soc., 7, 441–446.
26. Kondo T., Kimura Y., Kanda T., Takagi D., Wada K., and Toshimitsu A. (2011) Simple and practical aerobic oxidation of alcohols catalyzed by a (??oxo)tetraruthenium cluster. Green Sustain. Chem., 1, 149–154.
27. Shen H. -Y., Ying L. -Y., Jiang H. -L., and Judeh Z. M. A. (2007) Efficient copper?bisisoquinoline?based catalysts for selective aerobic oxidation of alcohols to aldehydes and ketones. Int. J. Mol. Sci., 8, 505–512.
28. Dijksman A., Marino?Gonzalez A., i Payeras A. M., Arends I. W. C. E., and Sheldon R. A. (2001) Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium / TEMPO as the catalytic system. J. Am. Chem. Soc., 123, 6826–6833.
29. Kloth K., Brunjes M., Kunst E., Joge T., Gallier F., Adibekian A., and Kirschning A. (2005) Practical TEMPO?mediated oxidation of alcohols using different polymer-bound Co?oxidants. Adv. Synth. Catal., 347, 1423–1434.
30. Huang K. C., Couttenye R. A., and Hoag G. E. (2002) Kinetics of heat-assisted persulfate oxidation of methyl tert-butyl ether (MTBE). Chemosphere, 49, 413–420.
31. Liang C. J., Bruell C. J., Marley M. C., and Sperry K. L. (2003) Thermally activated persulfate oxidation of trichloroethylene (TCE) and 1,1,1?trichloroethane in aqueous systems and soil slurries. Soil Sediment. Contam., 12, 207–228.
32. Anipsitakis G. P., and Dionysiou D. D. (2004) Radical generation by the interaction of transition metals with common oxidants. Environ. Sci. Technol., 38, 3705–3712.
33. Anipsitakis G. P., and Dionysiou D. D. (2004) Transition metal/UV?based advanced oxidation technologies for water decontamination. Appl. Catal. B: Environ., 54, 155–163.
34. Liang C., Bruell C. J., Marley M. C., and Sperry K. L. (2004) Persulfate oxidation for in situ remediation of TCE: I. activated by ferrous ion with and without a persulfate?thiosulfate redox couple. Chemosphere, 55, 1213–1223.
35. Liang C., Bruell C. J., Marley M. C., and Sperry K. L. (2004) Persulfate oxidation for in situ remediation: II. activated by chelated ferrous ion. Chemosphere, 55, 1225–1233.
36. Huang K. C., Zhao Z., Hoag G. E., Dahmani A., and Block P. A. (2005) Degradation of volatile organic compounds with thermally activated persulfate oxidation. Chemosphere, 61, 551–560.
37. Liang C., Wang Z. S., and Bruell C. J. (2007) Influence of pH on persulfate oxidation of TCE at ambient temperatures. Chemosphere, 66, 106–113.
38. Waldemer R. H., Tratnyek P. G., Johnson R. L., and Nurmi J. T. (2007) Oxidation of chlorinated ethenes by heat-activated persulfate: kinetics and products. Environ. Sci. Technol., 41, 1010–1015.
39. Rastogi A., Al?Abed S. R., and Dionysiou D. D. (2009) Sulfate radical?based ferrous–peroxymonosulfate oxidative system for PCBs degradation in aqueous and sediment systems. Appl. Catal. B: Environ., 85, 171–179.
40. Rastogi A., Al?Abed S. R., and Dionysiou D. D. (2009) Effect of inorganic, synthetic and naturally occurring chelating agents on Fe(II) mediated advanced oxidation of chlorophenols. Water Res., 43, 684–694.
41. Kolthoff I. M., Medalia A. I., and Raaen H. P. (1951) The reaction between ferrous iron and peroxides. IV. Reaction with potassium persulfate. J. Am. Chem. Soc., 73, 1733–1739.
42. House D. A. (1962) Kinetics and mechanism of oxidations by peroxydisulfate. Chem. Rev., 62, 185–200.
43. Oh S. -Y., Kim H. -W., Park, J. -M., Park H. -S., and Yoon C. (2009) Oxidation of polyvinyl alcohol by persulfate activated with heat, Fe2+ and zero?valent iron. J. Hazard. Mater., 168, 346–351.
44. Chaskar A. C., Bhandari, S. R., Patil A. B., Sharma O. P., and Mayeker S. (2009) Solvent-free oxidation of alcohols with potassium persulphate in the presence of Br?nsted acidic ionic liquids. Synth. Commun., 39, 366–370.
45. Marsh, H., and Rodr?guez–Reinoso F. (2006) Activated Carbon, Elsevier, Amsterdam.
46. Zeynizadeh B., and Setamdideh D. (2006) NaBH4/charcoal: a new synthetic method for mild and convenient reduction of nitroarenes. Synth. Commun., 36, 2699–2704.
47. Setamdideh D., and Zeynizadeh B. (2006) Mild and convenient method for reduction of carbonyl compounds with the NaBH4/charcoal system in wet THF. Z. Naturforsch., 61b, 1275–1281.
48. Dilmaghani K. A., Zeynizadeh B., and Parsajam H. (2012) The efficient synthesis of 3,4?dihydropyrimidin?2?(1H)-ones and their sulfur derivatives with H2SO4 immobilized on activated charcoal. Phosphorus, Sulfur, and Silicon, 187, 544–553.
49. Spectral database for organic compounds SDBS, http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi (accessed on Jan 2015).
50. NIST chemistry webbook, http://webbook.nist.gov/chemistry (accessed on Jan 2015).
2. Tojo G., and Fernandez M. (2006) Oxidation of Alcohols to Aldehydes and Ketones, Springer, New York.
3. Sheldon R. A., and Kochi, J. K. (1981) Metal?Catalyzed Oxidations of Organic Compounds, Academic Press, New York.
4. Hudlicky M. (1990) Oxidations in Organic Chemistry, American Chemical Society, Washington, DC.
5. Corey E. J., and Suggs J. W. (1975) Pyridinium chlorochromate. An efficient reagent for oxidation of primary and secondary alcohols to carbonyl compounds. Tetrahedron Lett., 16, 2647–2650.
6. Ley S. V., Norman J., Griffith W. P., and Marsden S. P. (1994) Tetrapropylammonium perruthenate, Pr4N+RuO4-, TPAP: a catalytic oxidant for organic synthesis. Synthesis, 639–666.
7. Fatiadi A. J. (1987) The classical permanganate ion: still a novel oxidant in organic chemistry. Synthesis, 85–127.
8. Firouzabadi H., and Mostafavipoor Z. (1983) Barium manganate. A versatile oxidant in organic synthesis. Bull. Chem. Soc. Jpn., 56, 914–917.
9. Lou J. -D., Wang M., Zhu L. -Y., and Fang Z. -G. (2003) Solvent free oxidation of alcohols catalyzed by KMnO4 adsorbed on Kieselguhr. Catal. Commun., 4, 647–649.
10. Fatiadi A. J. (1976) Active manganese dioxide oxidation in organic chemistry – Part I. Synthesis, 65–104.
11. Fatiadi A. J. (1976) Active manganese dioxide oxidation in organic chemistry – Part II. Synthesis, 133–167.
12. Taylor R. J. K., Reid M., Foot, J., and Raw S. A. (2005) Tandem oxidation processes using manganese dioxide: discovery, applications, and current studies. Acc. Chem. Res., 38, 851–869.
13. Lou J. -D., Ge J., Zou X. -N., Zhang C., Wang Q., and Ma Y. -C. (2011) Effective oxidation of alcohols with manganes dioxide supported on kieselguhr under heterogeneous conditions. Oxidat. Commun., 34, 361–365.
14. Mancuso A. J., Huang S. -L., and Swern D. (1978) Oxidation of long?chain and related alcohols to carbonyls by dimethyl sulfoxide activated by oxalyl chloride. J. Org. Chem., 43, 2480–2482.
15. Pfitzner K. E., and Moffatt J. G. (1963) A new and selective oxidation of alcohols. J. Am. Chem. Soc., 85, 3027–3028.
16. Parikh J. R., and Doering W. V. E. (1967) Sulfur trioxide in the oxidation of alcohols by dimethyl sulfoxide. J. Am. Chem. Soc., 89, 5505–5507.
17. Mckillop A., and Young D. W. (1979) Organic synthesis using supported reagents ? part I. Synthesis, 401–422.
18. Fétizon M. (2009) Silver(I) carbonate on celite. In: Paquette L. A., Crich D., Fuchs P. L., and Molander G. A. (Eds) Encyclopedia of Reagents for Organic Synthesis, 2nd Ed, Wiley, Chichester.
19. Dess D. B., and Martin J. C. (1983) Readily accessible 12?I?5 oxidant for the conversion of primary and secondary alcohols to aldehydes and ketones. J. Org. Chem., 48, 4155–4156.
20. Frigerio M., and Santagostino M. (1994) A mild oxidizing reagent for alcohols and 1,2?diols: o-iodoxybenzoic acid (IBX) in DMSO. Tetrahedron Lett., 35, 8019–8022.
21. More J. D., and Finney N. S. (2002) A Simple and Advantageous Protocol for the Oxidation of Alcohols with o-Iodoxybenzoic Acid (IBX). Org. Lett., 4, 3001–3003.
22. Lee S. B., and Lee J. C. (2009) Oxidation of benzylic alcohols with iodine and lithium carbonate in ionic liquid. Bull. Korean Chem. Soc., 30, 3107–3108.
23. Saikia I., Chakraborty P., and Phukan P. (2009) A new metal?free protocol for oxidation of alcohols using N,N?dibromo?p?toluenesulfonamide. Arkivoc, xiii, 281–286.
24. Vocanson F., Guo Y. P., Namy J. L., and Kagan H. B. (1998) Dioxygen oxidation of alcohols and aldehydes over a cerium dioxide-ruthenium system. Synth. Commun., 28, 2577–2582.
25. Mardur S. P., and Gokavi G. S. (2010) Selective oxidation of alcohols to aldehydes by hydrogen peroxide using hexamolybdochromate(III) as catalyst. J. Iran. Chem. Soc., 7, 441–446.
26. Kondo T., Kimura Y., Kanda T., Takagi D., Wada K., and Toshimitsu A. (2011) Simple and practical aerobic oxidation of alcohols catalyzed by a (??oxo)tetraruthenium cluster. Green Sustain. Chem., 1, 149–154.
27. Shen H. -Y., Ying L. -Y., Jiang H. -L., and Judeh Z. M. A. (2007) Efficient copper?bisisoquinoline?based catalysts for selective aerobic oxidation of alcohols to aldehydes and ketones. Int. J. Mol. Sci., 8, 505–512.
28. Dijksman A., Marino?Gonzalez A., i Payeras A. M., Arends I. W. C. E., and Sheldon R. A. (2001) Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium / TEMPO as the catalytic system. J. Am. Chem. Soc., 123, 6826–6833.
29. Kloth K., Brunjes M., Kunst E., Joge T., Gallier F., Adibekian A., and Kirschning A. (2005) Practical TEMPO?mediated oxidation of alcohols using different polymer-bound Co?oxidants. Adv. Synth. Catal., 347, 1423–1434.
30. Huang K. C., Couttenye R. A., and Hoag G. E. (2002) Kinetics of heat-assisted persulfate oxidation of methyl tert-butyl ether (MTBE). Chemosphere, 49, 413–420.
31. Liang C. J., Bruell C. J., Marley M. C., and Sperry K. L. (2003) Thermally activated persulfate oxidation of trichloroethylene (TCE) and 1,1,1?trichloroethane in aqueous systems and soil slurries. Soil Sediment. Contam., 12, 207–228.
32. Anipsitakis G. P., and Dionysiou D. D. (2004) Radical generation by the interaction of transition metals with common oxidants. Environ. Sci. Technol., 38, 3705–3712.
33. Anipsitakis G. P., and Dionysiou D. D. (2004) Transition metal/UV?based advanced oxidation technologies for water decontamination. Appl. Catal. B: Environ., 54, 155–163.
34. Liang C., Bruell C. J., Marley M. C., and Sperry K. L. (2004) Persulfate oxidation for in situ remediation of TCE: I. activated by ferrous ion with and without a persulfate?thiosulfate redox couple. Chemosphere, 55, 1213–1223.
35. Liang C., Bruell C. J., Marley M. C., and Sperry K. L. (2004) Persulfate oxidation for in situ remediation: II. activated by chelated ferrous ion. Chemosphere, 55, 1225–1233.
36. Huang K. C., Zhao Z., Hoag G. E., Dahmani A., and Block P. A. (2005) Degradation of volatile organic compounds with thermally activated persulfate oxidation. Chemosphere, 61, 551–560.
37. Liang C., Wang Z. S., and Bruell C. J. (2007) Influence of pH on persulfate oxidation of TCE at ambient temperatures. Chemosphere, 66, 106–113.
38. Waldemer R. H., Tratnyek P. G., Johnson R. L., and Nurmi J. T. (2007) Oxidation of chlorinated ethenes by heat-activated persulfate: kinetics and products. Environ. Sci. Technol., 41, 1010–1015.
39. Rastogi A., Al?Abed S. R., and Dionysiou D. D. (2009) Sulfate radical?based ferrous–peroxymonosulfate oxidative system for PCBs degradation in aqueous and sediment systems. Appl. Catal. B: Environ., 85, 171–179.
40. Rastogi A., Al?Abed S. R., and Dionysiou D. D. (2009) Effect of inorganic, synthetic and naturally occurring chelating agents on Fe(II) mediated advanced oxidation of chlorophenols. Water Res., 43, 684–694.
41. Kolthoff I. M., Medalia A. I., and Raaen H. P. (1951) The reaction between ferrous iron and peroxides. IV. Reaction with potassium persulfate. J. Am. Chem. Soc., 73, 1733–1739.
42. House D. A. (1962) Kinetics and mechanism of oxidations by peroxydisulfate. Chem. Rev., 62, 185–200.
43. Oh S. -Y., Kim H. -W., Park, J. -M., Park H. -S., and Yoon C. (2009) Oxidation of polyvinyl alcohol by persulfate activated with heat, Fe2+ and zero?valent iron. J. Hazard. Mater., 168, 346–351.
44. Chaskar A. C., Bhandari, S. R., Patil A. B., Sharma O. P., and Mayeker S. (2009) Solvent-free oxidation of alcohols with potassium persulphate in the presence of Br?nsted acidic ionic liquids. Synth. Commun., 39, 366–370.
45. Marsh, H., and Rodr?guez–Reinoso F. (2006) Activated Carbon, Elsevier, Amsterdam.
46. Zeynizadeh B., and Setamdideh D. (2006) NaBH4/charcoal: a new synthetic method for mild and convenient reduction of nitroarenes. Synth. Commun., 36, 2699–2704.
47. Setamdideh D., and Zeynizadeh B. (2006) Mild and convenient method for reduction of carbonyl compounds with the NaBH4/charcoal system in wet THF. Z. Naturforsch., 61b, 1275–1281.
48. Dilmaghani K. A., Zeynizadeh B., and Parsajam H. (2012) The efficient synthesis of 3,4?dihydropyrimidin?2?(1H)-ones and their sulfur derivatives with H2SO4 immobilized on activated charcoal. Phosphorus, Sulfur, and Silicon, 187, 544–553.
49. Spectral database for organic compounds SDBS, http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi (accessed on Jan 2015).
50. NIST chemistry webbook, http://webbook.nist.gov/chemistry (accessed on Jan 2015).