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Liquid Phase Hydrogenation of Maleic Acid Diethyl Ester and Its Mixture with 4-Nitrotoluene over Modified Skeletal Nickel

Received: 17 February 2017    Accepted: 10 March 2017    Published: 28 November 2017
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Abstract

4-aminotoluene is known as a good octane additive, the mixture of maleic acid diethyl ester and Succinate acid diethyl ester has good lubricating characteristics. The process of hydrogenation of maleic acid diethyl ester at atmospheric pressure in aqueous solution of 2-propanol over skeletal nickel and modified skeletal one was investigated. It is established that the nickel surface modification by sulfur does not lead to the increase of the catalyst activity in the hydrogenation of maleic acid diethyl ester as opposed to 4-nitrotoluene. The principal possibility of selective hydrogenation of mixture of maleic acid diethyl ester with 4-nitrotoluene was demonstrated.

Published in International Journal of Oil, Gas and Coal Engineering (Volume 5, Issue 6)
DOI 10.11648/j.ogce.20170506.15
Page(s) 153-157
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This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2024. Published by Science Publishing Group

Keywords

Liquid-Phase Hydrogenation, 4-Nitrotoluene, Maleic Acid Diethyl Ester, Skeletal Nickel

References
[1] Stakheev A. Y., Isaeva V. I., Kustov L. M. et al. Novel catalysts for selective hydrogenation of C≡ C bond based on Pd nanoparticles immobilized in phenylenecarboxylate frameworks (NH2)-MIL-53 (Al). Russian Chemical Bulletin, 2015, 64 (2), 284-290.
[2] Cárdenas-Lizana F., Gómez-Quero S., Keane M. A. Clean production of chloroanilines by selective gas phase hydrogenation over supported Ni catalysts. Applied Catalysis A: General, 2008, 334 (1), 199-206.
[3] Cárdenas-Lizana F., Gómez-Quero S., Keane M. A. et al. Pd-promoted selective gas phase hydrogenation of p-chloronitrobenzene over alumina supported Au. Journal of Catalysis, 2009, 262 (2), 235-243.
[4] Ostrovski N. M. Catalyst deactivation: mechanisms, kinetics, testing. Hemijska Industrija, 2009, 63 (5), 545-555.
[5] Rumyantsev R. N., Il’in A. A., Il’in A. P., Pazukhin I. V. Influence of mechanical activation of molybdenum oxide on its catalytic activity in the reaction of the partial oxidation of methanol. Theoretical and Experimental Chemistry, 2011, 47 (1), 41-44.
[6] Mäki-Arvela P., Kuusisto J., Sevilla E. M., et al. Catalytic hydrogenation of linoleic acid to stearic acid over different Pd-and Ru-supported catalysts. Applied Catalysis A: General, 2008, 345 (2), 201-212.
[7] Gelder E. A., Jackson S. D., Lok C. M. The hydrogenation of nitrobenzene to aniline: a new mechanism. Chemical communications, 2005, 4, 522-524.
[8] Barbov A. V., Nabilkov V. E., Ulitin M. V. Effect of Residual Aluminum in Raney Nickel on the Results of Thermochemical Studies on Hydrogenation. Russian journal of physical chemistry, 1997, 71 (3), 367-370.
[9] Afineevskii A. V., Osadchaia T. Y., Prozorov D. A., et al. Selective blockage of the catalyst active sites for the hydrogenation of various functional groups over Raney nickel and nickel supported on silica. Trends Green Chem. 2016, 2: 1.
[10] Lukin M. V, Afineevskii A. V. The concentration effect of adsorption nanocomplexes on the catalytic activity of skeletal nickel in liquid-phase hydrogenation of sodium maleate in aqueous organic environments. Protection of Metals and Physical Chemistry of Surfaces, 2013, 49 (4), 451-454.
[11] Gao C. G., Zhao Y. X., Liu D. S. Liquid phase hydrogenation of maleic anhydride over nickel catalyst supported on ZrO2–SiO2 composite aerogels. Catalysis Letters, 2007, 118 (1-2), 50-54.
[12] Feng Y., Yin H., Wang A., Xie T., Jiang T. Selective hydrogenation of maleic anhydride to succinic anhydride catalyzed by metallic nickel catalysts. Applied Catalysis A: General, 2012, 425, 205-212.
[13] Dowden D. A., Reynolds P. W. Some reactions over alloy catalysts. Discussions of the Faraday Society, 1950, 8, 184-190.
[14] Nijhuis T. A., Dautzenberg F. M., Moulijn J. A. Modeling of monolithic and trickle-bed reactors for the hydrogenation of styrene. Chemical Engineering Science, 2003, 58 (7), 1113-1124.
[15] Osadchaia T. Y., Afineevskii A. V., Prozorov D. A., Lukin M. V. Catalytic properties of the modified skeletal nickel in the reaction of liquid phase hydrogenation of 4-nitrotoluene. Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 2015, 58 (3), 26-31, (in Russian).
[16] Neri G., Musolino M. G., Rotondo E., Galvagno S. Catalytic hydrogenation of 2, 4-dinitrotoluene over a Pd/C catalyst: identification of 2-(hydroxyamino)-4-nitrotoluene (2HA4NT) as reaction intermediate. Journal of Molecular Catalysis A: Chemical, 1996, 111 (3), 257-260.
[17] Sokolsky D. V. Hydrogenation in solutions.[Gidrirovanie v rastvorakh]. Almaty: Nauka, 1979.
[18] Min K. I., Choi J. S., Chung Y. M., et al. p-Aminophenol synthesis in an organic/aqueous system using Pt supported on mesoporous carbons. Applied Catalysis A: General, 2008, 337 (1), 97-104.
[19] Lukin M. V., Prozorov D. A., Ulitin M. V., et al. Controlled deactivation of a skeletal nickel catalyst with sodium silfide in liquid-phase hydrogenation reactions. Kinetics and Catalysis, 2013, 54 (4), 412-419.
[20] Prozorov D. A., Lukin M. V., Ulitin M. V. Effect of controlled deactivation on the thermochemical characteristics of hydrogen adsorption on skeletal nickel from sodium hydroxide-water solutions. Russian Journal of Physical Chemistry A, 2013, 87 (4), 576-579.
[21] Ma X., Liu Y., Li X., et al. Water: the most effective solvent for liquid-phase hydrodechlorination of chlorophenols over Raney Ni catalyst. Applied Catalysis B: Environmental, 2015, 165, 351-359.
[22] Lukin M. V., Prozorov D. A., Ulitin M. V., et al. Dependence of the thermodynamic characteristics of forms of hydrogen adsorbed on a porous nickel surface on the degree of deactivation. Russian Journal of Physical Chemistry A, 2013, 87 (7), 1092-1096.
Cite This Article
  • APA Style

    Andrei Vladimirovich Afineevskii, Tatiana Yurievna Osadchaia, Dmitrii Alekseevich Prozorov, Mikhail Viktorovich Lukin, Yaroslav Pavlovich Suhachev, et al. (2017). Liquid Phase Hydrogenation of Maleic Acid Diethyl Ester and Its Mixture with 4-Nitrotoluene over Modified Skeletal Nickel. International Journal of Oil, Gas and Coal Engineering, 5(6), 153-157. https://doi.org/10.11648/j.ogce.20170506.15

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    ACS Style

    Andrei Vladimirovich Afineevskii; Tatiana Yurievna Osadchaia; Dmitrii Alekseevich Prozorov; Mikhail Viktorovich Lukin; Yaroslav Pavlovich Suhachev, et al. Liquid Phase Hydrogenation of Maleic Acid Diethyl Ester and Its Mixture with 4-Nitrotoluene over Modified Skeletal Nickel. Int. J. Oil Gas Coal Eng. 2017, 5(6), 153-157. doi: 10.11648/j.ogce.20170506.15

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    AMA Style

    Andrei Vladimirovich Afineevskii, Tatiana Yurievna Osadchaia, Dmitrii Alekseevich Prozorov, Mikhail Viktorovich Lukin, Yaroslav Pavlovich Suhachev, et al. Liquid Phase Hydrogenation of Maleic Acid Diethyl Ester and Its Mixture with 4-Nitrotoluene over Modified Skeletal Nickel. Int J Oil Gas Coal Eng. 2017;5(6):153-157. doi: 10.11648/j.ogce.20170506.15

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  • @article{10.11648/j.ogce.20170506.15,
      author = {Andrei Vladimirovich Afineevskii and Tatiana Yurievna Osadchaia and Dmitrii Alekseevich Prozorov and Mikhail Viktorovich Lukin and Yaroslav Pavlovich Suhachev and Marina Dmitrievna Chelysheva and Vladislav Olegovich Gundorov},
      title = {Liquid Phase Hydrogenation of Maleic Acid Diethyl Ester and Its Mixture with 4-Nitrotoluene over Modified Skeletal Nickel},
      journal = {International Journal of Oil, Gas and Coal Engineering},
      volume = {5},
      number = {6},
      pages = {153-157},
      doi = {10.11648/j.ogce.20170506.15},
      url = {https://doi.org/10.11648/j.ogce.20170506.15},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ogce.20170506.15},
      abstract = {4-aminotoluene is known as a good octane additive, the mixture of maleic acid diethyl ester and Succinate acid diethyl ester has good lubricating characteristics. The process of hydrogenation of maleic acid diethyl ester at atmospheric pressure in aqueous solution of 2-propanol over skeletal nickel and modified skeletal one was investigated. It is established that the nickel surface modification by sulfur does not lead to the increase of the catalyst activity in the hydrogenation of maleic acid diethyl ester as opposed to 4-nitrotoluene. The principal possibility of selective hydrogenation of mixture of maleic acid diethyl ester with 4-nitrotoluene was demonstrated.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - Liquid Phase Hydrogenation of Maleic Acid Diethyl Ester and Its Mixture with 4-Nitrotoluene over Modified Skeletal Nickel
    AU  - Andrei Vladimirovich Afineevskii
    AU  - Tatiana Yurievna Osadchaia
    AU  - Dmitrii Alekseevich Prozorov
    AU  - Mikhail Viktorovich Lukin
    AU  - Yaroslav Pavlovich Suhachev
    AU  - Marina Dmitrievna Chelysheva
    AU  - Vladislav Olegovich Gundorov
    Y1  - 2017/11/28
    PY  - 2017
    N1  - https://doi.org/10.11648/j.ogce.20170506.15
    DO  - 10.11648/j.ogce.20170506.15
    T2  - International Journal of Oil, Gas and Coal Engineering
    JF  - International Journal of Oil, Gas and Coal Engineering
    JO  - International Journal of Oil, Gas and Coal Engineering
    SP  - 153
    EP  - 157
    PB  - Science Publishing Group
    SN  - 2376-7677
    UR  - https://doi.org/10.11648/j.ogce.20170506.15
    AB  - 4-aminotoluene is known as a good octane additive, the mixture of maleic acid diethyl ester and Succinate acid diethyl ester has good lubricating characteristics. The process of hydrogenation of maleic acid diethyl ester at atmospheric pressure in aqueous solution of 2-propanol over skeletal nickel and modified skeletal one was investigated. It is established that the nickel surface modification by sulfur does not lead to the increase of the catalyst activity in the hydrogenation of maleic acid diethyl ester as opposed to 4-nitrotoluene. The principal possibility of selective hydrogenation of mixture of maleic acid diethyl ester with 4-nitrotoluene was demonstrated.
    VL  - 5
    IS  - 6
    ER  - 

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Author Information
  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

  • Department of Physical and Colloidal Chemistry, Ivanovo State University of Chemistry and Technology, Ivanovo Region, Ivanovo, Russia

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