A Green Protocol for Selective Oxidation of Alcohols to Carbonyl Compounds Comparative Studies with Various Ni Heterogeneous Catalysts with O2 and H2O2 as Oxidants.

Ateeq Rahman, Luke Gwatidzo

Abstract


The mini article highlights the versatility of Ni-Al hydrotalcite (HT) catalysts using molecular oxygen as oxidant compared to Ni/SiO2, Ni and other catalysts reported for oxidation of alcohols to carbonyl compounds. Among the catalysts reported in literature to date, Ni-Al HT is the best catalysts suited for molecular oxygen initiated oxidation of alcohols to carbonyl compounds. Benzylic alcohols, substitute benzylic, allylic, ?-ketols and substituted cinnamyl alcohols are oxidized to aldehydes and ketones. Ni in association with oxide of aluminium is the active precursor for the title reaction and Ni-Al HT catalysts was characterized by TPR, XRD, IR, and DSC. Ni/SiO2 also exhibited some activity for oxidation of alcohols to carbonyl compounds with 30% H2O2 as oxidant, whereas, Ni/TiO2 did not exhibit activity for the title reaction which is due to uneven distribution of Ni on TiO2 surface. Hence, from these results, it is evident that Ni hydrotalcite catalysts with molecular oxygen is the active catalysts for alcohol oxidation to carbonyl compounds which have valuable applications in fine chemical industry and academia.


Keywords


Ni-Al hydrotalcite; heterogeneous catalysts; Ni/SiO2; Ni/TiO2; oxidation reactions.

Full Text:

PDF

References


March. J, Advanced Organic Chemistry: Reactions Wiley: New York, 1992.

Schmiedervan de Vondervoort, L.; Bouttemy, S.; Padrn, J. M.; Le Bras, J.; Muzart, Alsters. J. P. L. Chromium Catalyzed Oxidation of (Homo-) Allylic and (Homo-) Propargylic Alcohols with Sodium Periodate to Ketones or Carboxylic Acids. Synlett 243-246, 2002.

Indranirekha .S. Chakraborty. P. and Prodeep. P., A new metal-free protocol for oxidation of alcohols using N,N-dibromo-p-toluenesulfonamide. ARKIVOC (xiii) 281-286, 2009.

Miyazawa. T, Endo. , Shiihashi. S., and Okawara. M., Selective oxidation of alcohols by oxonium salts (R2N:O+X-). J. Org. Chem, 50,1332-1334, 1985.:10.1021/jo00208a047 .

Anelli P. L., Biffi. C., Montanari. F., and Quici. S., Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditions. J. Org. Chem, 52, 2559-2562, 1987.

De Nooy A. E. J., Besemer. A. C., and Bekkum. Van. H., On the use of stable organic Nitroxyl radicals for the oxidation of primary and secondary alcohols. Synthesis, 10, 1153-1176, 1996.

Rychnovsky. S. D., and Vaidyanathan. R., TEMPO- catalyzed oxidations of Alcohols Using m-CPBA: The role of Halide Ions. J. Org. Chem, 64, 310-312, 1999.

Zhao. M., Li. J., Mano. E., Song. Z., Tschaen. D. M., Grabowski E. J. J. , and Reider P.J.,Oxidation of primary alcohols to carboxylic acids with Sodium Chlorite catalyzed by TEMPO and Bleach.. J. Org. Chem, 64, 2564-2566, 1999.

Tashino. Y., and Togo. H., TEMPO-Mediated Environ-mentally Benign Oxidation of Primary Alcohols to Car-boxylic Acids with Poly[4-(diacetoxyiodo)styrene. J. Org. Chem, 36, 123-125, 2005.

Zhao. M., , Li. J., , Mano E., Song. Z. J., and Tschaen. D. M., Oxidation of Primary Alcohols to Carboxylic Acids with Sodium Chlorite Catalyzed by TEMPO and Bleach: 4-Methoxyphenylacetic Acid, . Org. Synth, 81,195-203, 2005.

Sheldon. R.A. In: Simandi, L.L. Editor. Dioxygen Activation and Homogeneou.s Catal Oxidation; Elsevier: Amsterdam, 573, 1991.

Ravikumar R. Gowda, Debashis Chakraborty. La2O3 Catalyzed Oxidation of alcohols. International. J. Org. Chem, 1, 41-46, 2011.

Strukul, G. Catalytic Oxidations with Hydrogen Peroxide as Oxidant. Kluwer Academic Publishers: London, 45, 1992.

Sato K., Takagi J., Aoki .M., Noyori. R., Hydogen peoxide oxidation of benzyl Alcohols to benzaldehydes under solvent free condition. Tet. Lett.39, 7549 -7552, 1998.

Sato, K; Aoki, M.; Noyori, R. A A Green Route to Adipic Acid: Direct Oxidation of Cyclohexenes with 30 Percent Hydrogen Peroxide. Science 281,1646-1647, 1998.

Ibrahim KAN?I, Mehmet KURTCA. Synthesis, structural characterization, and benzyl alcohol oxidation activity of mononuclear manganese(II) complex with 2,2'-bipyridine: [Mn(bipy)_2(ClO4)2]. Turk J Chem 36, 827 840, 2012.

Imtiyaz Rasool Parrey and Athar adil Hashmi. Synthesis of Schif Base Complexes of Mn(II) and Co(II) and their Catalytic Oxidation towards olefins and alcohols. Can. Chem. Trans 3, 65-71, 2015.

Bolm, C., Magnus, A.S., and Hildebrand, J.P. Catalytic Synthesis of Aldehydes and Ketones under Mild Conditions Using TEMPO/Oxone. Org. Lett., 2, 1173-1175, 2000.

Kim, S.S. and Nehru, K. A Mild and Efficient Oxidation of Alcohols to Carbonyl Compounds by Periodic Acid Catalyzed by 2,2,6,6-Tetramethylpiperidinyl-1-oxyl. Synlett, 616-619, 2002.

Anelli, L., Biffi, C., Montanari, F., and Quici, S. Fast and selective oxidation of primary alcohols to aldehydes or to carboxylic acids and of secondary alcohols to ketones mediated by oxoammonium salts under two-phase conditions.J. Org. Chem. 52, 2559-2562, 1987.

Anelli, P., Banfi, S., Montanari, F., and Quici, S. Oxidation of diols with alkali hypochlorites catalyzed by oxammonium salts under two-phase conditions. J. Org. Chem., 54, 2970-2972, 1989.

Anelli, P. L., Montanari, F., and Quici, S. A General Synthetic method for the oxidation of pimary alcohols o aldehydes: (S)-(+)-2-Methyl butanal [Butanal, 2-methyl-, (S)-] Org. Synth., 69, 212-218, 1990.

Yadav, J. S.; Reddy, B. V. S.; Basak, A. K.; Narsaiah, A. V. Recyclable 2nd generation ionic liquids as green solvents for the oxidation of alcohols with hypervalent iodine reagents. Tett, 60, 2131-2135, 2004.

Sheldon, R.A.; Kochi, J.K. In Metal-Catalyzed Oxidations of Organic Compounds. Academic Press: New York, 121-123, 1981.

Sheldon. R.A. In: Simandi, L.L. Editor. :Dioxygen Activation and Homogeneous Catalytic Oxidation; Elsevier: Amsterdam, 573-579, 1991.

Sato, K.; Takagi, J.; Aoki, M.; Noyori, R. :Hydrogen peroxide oxidation of benzylic Alcohol to benzaldehydes and benzoic acids under halide-free conditions. Tett. Lett 39, 7549 -7552,1998.

Laura M. Dornan, Grinne M. A. , Mateusz B. Pitak, Simon J. Coles and Mark. J., Muldoon, M. J., N,O-ligated Pd(II) complexes for catalytic alcohol oxidation. Catal. Sci. Technol., 4, 2526-2534, 2014.

Marko I. E., Giles. P., Tsukazaki. M., ChelleRegnaut. I., Urch. C., Copper-Catalyzed Oxidation of Alcohols to Aldehydes and Ketones: An Efficient, Aerobic Alternatie. Science 274, 2044-2046, 1996.

Lahtinen. P., Korpi. H., Haavisto, E., Leskel M., Repo. Parallel Screening of Homogeneous Copper Catalysts for the Oxidation of Benzylic Alcohols with Molecular Oxygen in Aqueous Solutions. J. Comb. Chem.6, 967- 973, 2004.

Gamez. P., Arends. I. W. C. E., Sheldon. A., Room Temperature Aerobic CopperCatalysed Selective Oxidation of Primary Alcohols to Aldehydes. Adv. Synth. Catal. 346, 805-811, 2004.

Betzemeier. B., Cavazzini. M., Quici. S., Knochel. P., T. Copper-catalyzed aerobic oxidation of alcohols under fluorous biphasic conditions. Tet. Lett. 41, 4343-4352, 2000.

Mannam. S., Alamsetti. S., Alamsetti. S. K., Sekar., Aerobic, Chemoselective Oxidation of Alcohols to Carbonyl Compounds Catalyzed by a DABCO-Copper Complex under Mild Conditions. Adv. Synth. Catal. 349, 2253-2258, 2007.

Komiya, N., Nakae, T., Sato, H., and Naota, T. Water-soluble diruthenium complexes bearing acetate and carbonate bridges: highly efficient catalysts for aerobic oxidation of alcohols in water. Chem. Commun., 48294831, 2006.

Manyar, H.G., Chaure, G.S., and Kumar, A. The green catalytic oxidation of alcohols in water by using highly efficient manganosilicate molecular sieves. Green Chem., 8, 344 348, 2006.

Janssen, M. H. A., Chesa Castellana, J.F., Jackman, H., Dunn, P.J., and Sheldon, R.A. Towards greener solvents for the bleach oxidation of alcohols catalyzed by stable N-oxy Radicals. Green Chem 13, 905-912, 2011.

Muzart. J., Ajjou. A. N. J., Chromium (VI) catalyzed oxidation of adamantine by tert- butyl hydoperoxide. J. Mol. Catal. 84, L15-L19, 1993.

Deng. M., Zhao. . Xue. Q., Chen. L., LY. u., :Microfibrous-structured silver catalyst for low-temperature gas-phase selective oxidation of benzyl alcohol. Appl. Catal. B Environmental 99, 222-228, 2010.

Ming-lin. ., Hui-zhen. L., Selective oxidation of benzyl alcohol to benzaldehyde with hydrogen peroxide over tetra-alkylpyridinium octamolybdate catalysts. Green Chem. 9421-423, 2007.

Choudhary. V. R., Dumbre. D. K., Solvent-free selective oxidation of benzyl alcohol to benzaldehyde by tert-butyl hydopeoxide over U3O8-supported nano gold catalysts. Appl. Catal. A General 375, 252-257, 2010.

Su. Y., Wang. L.C., Liu. Y. M., Cao. Y., He. H. Y., Fan. K. N., Micowave accelerated solvent free aerobic oxidation of benzyl alcohol over efficient and reusable manganese oxides. Catal. Commun. 8, 2181-2185, 2007.

Ji. H. B., Song. J., He. B., Qian. Y., Kinetic evidence for the mechanism of liquid-solid phase oxidation of alcohols. React. Kinet. Catal. Lett. 82, 97-100, 2004.

Tang. Q., Gong. X., Zhao. P., Chen. Y., Yang. Y., Copper-manganese oxide supported On alumina: Physicochemical features and catalytic perfomances in the aerobic oxidation of benzyl alcohol. Appl. Catal. A General 389, 101-107, 2010.

Tang. Q., Wu. C., Qiao. Chen. Y., Yang. Y., Catalytic performance of Mn-Ni mixed hydroxide catalysts in liquid phase benzyl alcohol oxidation using molecular oxygen. Appl. Catal. A General 403, 136-141, 2011.

Nagashima. K., Mitsudome. M. T., Jitsukawa. K., Kaneda. K., Efficient aerobic Oxidation of alcohols using hydrotalcite-supported gold nanoparticle catalyst Adv. Synth. Catal., 351,1890-1896, 2009.

Ghafuri. H., Current Transition metal-free oxidation of benzylic alcohols to carbonyl compounds by hydrogen peroxide in the presence of acidic silica gel. Chem. letts 427-32, 2015.

Choudary. B. M., Kantam. M. L., Rahman. A., Reddy. Ch.., and Koteshwar K. R.The First Example of Activation of Molecular Oxygen by Nickel in Ni-Al Hydrotalcite: A Novel Protocol for the Selective Oxidation of Alcohols. Angew. Chem. Int. Ed. 40 763-766, 2001.

Rahman. A., Rajasekhar. P., Jonnalagadda. S. B., Selective oxidation of p-nitrobenzyl alcohol to p-nitrobenzaldehyde with 10% Ni silica with 30% H2O2 in acetonitrile solvent. Catal. Commun 9, 2417 2421, 2008.

Kantam. M. L., Bandyopadhyay. . Rahman. A., Reddy. N. M., Choudary. B. M., Reduction of nitroaromatics with a new heterogenised MCMsilylamine palladium II/catalyst. J. Mol. Catal. A 133, 293-295, 1998.

Manayil. J. C., Sivashunmugam S, Bhadoria. D. S., and Srinivasan. K., CoAl-CrO4Layered Double Hydroxides as Selective Oxidation Catalysts at Room Temperature. Ind. Eng. Chem. Res. 50, 13380-13386, 2011.

Rahman A., and Deyab. S. S-Al., A review on reduction of acetone to isopropanol with Ni nano superactive, heterogeneous catalysts as an environmentally benevolent approach, Appl. Catal A: General, 469, 517-523, 2014.

Adam. F., and Ting. O. W., New porpyrin hybrid material based on functional silica for oxidation of benzyl alcohol. J. Phys. Science, 24, 119, 2013.

Nakgawa. L., Konaka., and Nakata. T., Oxidation with nickel peroxide. I Oxidation of alcohols. J. Org. Chem, 27, 1597-1601, 1962.

Konaka. R., Terabe. S., and Kuruma. K., Mechanism of the oxidation reaction with Nickel peroxide. J. Org. Chem, 34, 1334-1337, 1969.

Christoskova. S., Danova. N., Georgieva. M., Argirov. O. K., and Mahendzhiev. D. Inestigation of a nickel oxide system for heterogeneous oxidation of organic compounds.J. Appl. Catal A: General 128, 219-224, 1995.

Ji, H., Wang. Zhang. M., She. Y., and Wang. L., Simple fabrication of nano-sized NiO2 powder and its application to oxidation reactions. J. Appl. Catal. A: General, 282 2005, 25-30.


Refbacks

  • There are currently no refbacks.


 

 
  
 

 

  


About IJSBAR | Privacy PolicyTerms & Conditions | Contact Us | DisclaimerFAQs 

IJSBAR is published by (GSSRR).