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Degradation Reactions in Anthraquinone Process of Hydrogen Peroxide Synthesis

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Abstract

Present research concentrates on the process of anthraquinone degradation in the course of hydrogenation carried out in the presence of palladium catalyst. Hydrogenation experiments were carried out using agitated glass laboratory batch type reactor at atmospheric pressure of hydrogen and temperature of 55 °C. Catalytic tests were performed using solutions composed of 2-ethyl-9,10-anthraquinone (eAQ) and a mixture of eAQ and 2-ethyloxanthrone (OXO) with various proportions. Degradation of anthraquinone was studied and in particular, the role of reduced forms of quinone namely hydroquinone and its tautomer OXO is discussed. A difference in the course of reactions pathways: hydrogenation of aromatic rings to give 2-ethyl-5,6,7,8-tetrahydro-9,10-anthraquinone (active quinone) and hydrogenolysis reactions yielding degradation products was observed.

Graphical Abstract

Present research concentrates on the process of 2-ethyl-9,10-anthraquinone degradation on palladium catalyst. The role of reduced forms, hydroquinone-enol form and its keto-tautomer is discussed.

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Abbreviations

eAQ:

2-Ethyl-9,10-anthraquinone

eAQH2 :

2-Ethyl-9,10-anthrahydroquinone

H4eAQ:

2-Ethyl-5,6,7,8-tetrahydro-9,10-anthraquinone

H4eAQH2 :

2-Ethyl-5,6,7,8-tetrahydro-9,10-anthrahydroquinone

H8eAQ:

2-Ethyl-1,2,3,4,5,6,7,8-octahydro-9,10-anthraquinone

eAN:

2-Ethylanthrone (2-ethyl-10-anthrone and 2-ethyl-9-anthrone)

H4eAN:

2-Ethyl-5,6,7,8-tetrahydroanthrone

OXO:

2-Ethyl-10-hydroxy-9-anthrone (2-ethyloxanthrone)

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Authors and Affiliations

  1. Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, 30-238 Kraków, Niezapominajek 8, Poland

    R. Kosydar & A. Drelinkiewicz

  2. Solvay Research and Technology, Rue de Ransbeek 310, 1120, Brussels, Belgium

    J. P. Ganhy

Authors
  1. R. Kosydar
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  2. A. Drelinkiewicz
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  3. J. P. Ganhy
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Correspondence to A. Drelinkiewicz.

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Kosydar, R., Drelinkiewicz, A. & Ganhy, J.P. Degradation Reactions in Anthraquinone Process of Hydrogen Peroxide Synthesis. Catal Lett 139, 105–113 (2010). https://doi.org/10.1007/s10562-010-0413-1

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  • DOI: https://doi.org/10.1007/s10562-010-0413-1

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