Simple and Green Adipic Acid Synthesis from Cyclohexanone and/or Cyclohexanol Oxidation with Efficient (NH4)xHyMzPMo12O40 (M: Fe, Co, Ni) Catalysts
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
The oxidation of cyclohexanone and/or cyclohexanol to adipic acid (AA) was performed at 90 °C with a reaction time of 20 h, in the presence of H2O2 as oxidant and transition metal substituted ammonia polyoxometalates of formula, (NH4)xHyMzPMo12O40 (M: Fe, Co, or Ni, and x = 2.5 or 2.28) as catalysts. The catalytic results showed that the AA yield is sensitive to the transition metal nature and to the reaction conditions (sample weight and substrate amount). The (NH4)2.29H0.39Co0.16PMo12O40 was found to be the better catalytic system toward AA synthesis from cyclohexanone oxidation, with 40% of AA yield Copyright © 2018 BCREC Group. All rights reserved
Received: 12nd November 2017; Revised: 18th February 2018; Accepted: 19th February 2018; Available online: 11st June 2018; Published regularly: 1st August 2018
How to Cite: Mouanni, S., Mazari, T., Benadji, S., Dermeche, L., Marchal-Roch, C., Rabia, C. (2018). Simple and Green Adipic Acid Synthesis from Cyclohexanone and/or Cyclohexanol Oxidation with Efficient (NH4)xHyMzPMo12O40 (M: Fe, Co, Ni) Catalysts. Bulletin of Chemical Reaction Engineering & Catalysis, 13 (2): 386-392 (doi:10.9767/bcrec.13.2.1749.386-392)
- Bonnet, D., Ireland, T., Fache, E., Simonato, J.P. (2006). Innovative direct synthesis of adipic acid by air oxidation of cyclohexane. Green Chem., 8: 556-559
- Shimizu, A., Tanaka, K., Ogawa, H., Matsuoka, Y., Fujimori, M., Nagamori, Y., Hamachi, H. (2003). Recent Advances in Transition Metal Catalyzed Oxidation of Organic Substrates with Molecular Oxygen B. Chem. Soc. Jpn., 76: 1993-2001
- Chavan, S.A., Srinivas, D., Ratnasamy, P. (2002). Oxidation of Cyclohexane, Cyclohexanone, and Cyclohexanol to Adipic Acid by a Non-HNO3 Route over Co/Mn Cluster Complexes. J. Catal., 212: 39-45
- Sato, K., Aoki, M., Noyori, R. (1998). A ‘‘green’’ route to adipic acid: direct oxidation of cyclohexenes with 30 percent hydrogen peroxide. Science, 281: 1646-1647.
- Vyver, S.V., Román-Leskov, Y. (2013). Emerging catalytic processes for the production of adipic acid. Catal. Sci. Technol., 3: 1465-1479.
- Nomiya, K., Miwa, M., Sugaya, Y. (1984). Catalysis by heteropolyacid-VII. catalytic oxidation of cyclohexanol by dodecamolybdate. Polyhedron, 3: 607-610
- Davis, D.D., Kemp, D.R. AdipicAcid in ECT, 2000
- Dickinson, R.E., Cicerone, R.J. (1986). Future Global Warming from Atmospheric Trace Gases. Nature, 319: 109-115
- Li, J., Luo, G., Chu, Y., Wei, F. (2012). Experimental and modeling analysis of NO reduction by CO for a FCC regeneration process. Chem. Eng. J., 184: 168-175
- Wang, Y., Geng, J., Guo, G., Wang, C., Liu, S. (2011). N2O production in anaerobic/anoxic denitrifying phosphorus removal process: The effects of carbon sources shock. Chem. Eng. J., 172: 999-1007
- Hill, C.L., Prosser-McCartha, C.M. (1995). Homogeneous Catalysis by Transition Metal Oxygen Anion Clusters. Coord. Chem. Rev., 143: 407-455
- Okuhara, T., Mizuno, N., Misono, M. (1996). Catalytic Chemistry of Heteropoly Compounds. Adv. Catal., 41: 113-252
- Neumann, R. (1998). Polyoxometalate Complexes in Organic Oxidation Chemistry. Prog. Inorg. Chem., 47: 317-370
- Kozhevnikov, I.V. (1998). Catalysis by Heteropoly Acids and Multicomponent Polyoxometalates in Liquid-Phase Reactions. Chem. Rev., 98: 171-198
- Mizuno, N., Kamata, K., and Yamaguchi, K. (2011). Liquid-phase selective oxidation by multimetallic active sites of polyoxometalate-based molecular catalysts. Top Organomet. Chem., 37: 127-160
- Vazylyev, M., Sloboda-Rozner, D., Haimov, A.D., Maayan, G., Neumann, R. (2005). Strategies for oxidation catalyzed by polyoxometalates at the interface of homogeneous and heterogeneous catalysis. Top Catal., 34 (1-4): 93-99
- Mizuno, N., Kamata, K., Yamaguchi, K. (2011). Liquid-Phase Selective Oxidation by Multimetallic Active Sites of Polyoxometalate-Based Molecular Catalysts Top Organomet. Chem., 37: 127-160
- Mazari, T., Benadji, S., Tahar, A., Dermeche, L., Rabia, C. (2013). Liquid Phase synthesis of adipic acid using Keggin-type phosphomolybdates catalysts. J. Mater. Sci. Eng. B. 3(3): 146-151
- Benadji, S., Mazari, T., Dermeche, L., Salhi, N., Cadot, E., Rabia, C. (2013). Preparation, Characterization and Reactivity of Keggin Type Phosphomolybdates, H3−2xNixPMo12O40 and (NH4)3−2xNixPMo12O40, for Adipic Acid Synthesis. Catal. Lett., 143: 749-755
- Tahar, A., Benadji, S., Mazari, T., Dermeche., L. Roch-Marchal, C., Rabia, C. (2015). Preparation, Characterization and Reactivity of Keggin Type Phosphomolybdates, H3−2x Ni x PMo12O40 and (NH4)3−2xNixPMo12O40, for Adipic Acid Synthesis. Catal. Lett., 145: 569-575
- Moudjahed, M., Dermeche, L., Benadji, S., Mazari, T., Rabia, C. (2016). Dawson-type polyoxometalates as green catalysts for adipic acidsynthesis. J. Mol. Catal. A: Chem., 414: 72-77
- Tsigdinos, G.A. (1974). Preparation and Characterization of 12-Molybdophosphoric and 12-Molybdosilicic Acids and Their Metal Salts. Ind. Eng. Chem. Prod. Res. Dev., 13: 267-274
- Mizuno, N., Tateishi, M., Iwamoto, M. (1994). Enhancement of catalytic activity of Cs2.5Ni0.08H0.34PMo12O40 by V5+-substitution for oxidation of isobutane into m
- ethacrylic. Appl. Catal. A: Gen., 118: L1-L4.
- Rocchiccioli-Deltcheff, C., Fournier, M., Frank, R., Thouvenot, R. (1983). Vibrational investigations of polyoxometalates. 2. Evidence for anion-anion interactions in molybdenum(VI) and tungsten(VI) compounds related to the Keggin structure. Inorg. Chem., 22: 207-216
- Cavani, F., Mezzogori, R., Pigamo, A., Trifirò, F., Etienne, E. (2001). Main aspects of the selective oxidation of isobutane to methacrylic acid catalyzed by Keggin-type polyoxometalates. Catal. Today, 71: 97-110
- Clerici, MG., Anfossi, B., Bellussi, G. (1991) Process for oxidating paraffinic compounds. European Patent 0 412 596 A1.
- Mimoun, H., Saussine, L., Daire, E., Robine, A., Guibourd de Luzinais, J. (1984). Peroxidic complexes of vanadium, niobium and tantalum, used as reactants and as catalysts for olefins epoxidation and hydrocarbons hydroxylation. European Patent 0 097 551 A1.
- Ingle, R.H., Kala, N.K., Manikandan, P. (2007). [SbW9O33]-based polyoxometalate combined with a phase transfer catalyst: A highly effective catalyst system for selective oxidation of alcohols with H2O2, and spectroscopic investigation. J. Mol. Catal. A, 262: 52-58.
- Wu, Y., Qu, S., Ma, H., Ye, S. (1994). Catalytic behaviour of metal ions located at different sites of heteropolycompounds. Catal. Lett., 23: 195-205.
This work is licensed under a Creative Commons Attribution-ShareAlike 4.0 International License.
As a journal Author, you have rights for a large range of uses of your article, including use by your employing institute or company. These Author rights can be exercised without the need to obtain specific permission.
Authors publishing in BCREC journals have wide rights to use their works for teaching and scholarly purposes without needing to seek permission, including: use for classroom teaching by Author or Author's institutionand presentation at a meeting or conference and distributing copies to attendees; use for internal training by author's company; distribution to colleagues for their reseearch use; use in a subsequent compilation of the author's works; inclusion in a thesis or dissertation; reuse of portions or extrcats from the article in other works (with full acknowledgement of final article); preparation of derivative works (other than commercial purposes) (with full acknowledgement of final article); voluntary posting on open web sites operated by author or author’s institution for scholarly purposes (follow CC by SA License).
Authors and readers can copy and redistribute the material in any medium or format, as well as remix, transform, and build upon the material for any purpose, even commercially, but they must give appropriate credit (cite to the article or content), provide a link to the license, and indicate if changes were made. If you remix, transform, or build upon the material, you must distribute your contributions under the same license as the original.
Copyright Transfer Agreement
The Authors submitting a manuscript do so on the understanding that if accepted for publication, copyright publishing of the article shall be assigned to Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University as publisher of the journal.
Copyright encompasses exclusive rights to reproduce and deliver the article in all form and media, including reprints, photographs, microfilms and any other similar reproductions, as well as translations. The reproduction of any part of this journal, its storage in databases and its transmission by any form or media, such as electronic, electrostatic and mechanical copies, photocopies, recordings, magnetic media, etc., will be allowed only with a written permission from Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University.
Bulletin of Chemical Reaction Engineering & Catalysis journal and Department of Chemical Engineering Diponegoro University, the Editors and the Advisory International Editorial Board make every effort to ensure that no wrong or misleading data, opinions or statements be published in the journal. In any way, the contents of the articles and advertisements published in the Bulletin of Chemical Reaction Engineering & Catalysis are sole and exclusive responsibility of their respective authors and advertisers.
Remember, even though we ask for a transfer of copyright, our journal authors retain (or are granted back) significant scholarly rights.
The Copyright Transfer Form can be downloaded here: [Copyright Transfer Form BCREC 2016]
The copyright form should be signed originally and send to the Editorial Office in the form of original mail, scanned document or fax :
Prof. Dr. I. Istadi (Editor-in-Chief)
Editorial Office of Bulletin of Chemical Reaction Engineering and Catalysis
Department of Chemical Engineering, Diponegoro University
Jl. Prof. Soedarto, Kampus Undip Tembalang, Semarang, Central Java, Indonesia 50275
Telp.: +62-24-7460058, Fax.: +62-24-76480675