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Upgrading of Lignin-Derived Compounds: Reactions of Eugenol Catalyzed by HY Zeolite and by Pt/γ-Al2O3

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Abstract

The conversion of eugenol (4-allyl-2-methoxyphenol), a compound derived from the lignin in woody biomass, was catalyzed by HY zeolite at 573 K and atmospheric pressure. The main products were isoeugenol and guaiacol, formed by isomerization and by deallylation, respectively. Substituted guaiacols with saturated side-chains (4-methylguaiacol, 4-ethylguaiacol, and 4-propylguaiacol) were also formed, by hydrogen transfer and alkylation reactions. The pseudo-first-order rate constant for the overall disappearance of eugenol was found to be 12.4 L (g of catalyst)/h. When the catalyst was Pt/γ-Al2O3 used in the presence of H2, significant hydrogenation of the propenyl side-chain took place, accompanied by isomerization, and hydrodeoxygenation. Under similar operating conditions, the reaction catalyzed by Pt/γ-Al2O3 in the presence of H2 gave a higher eugenol conversion (X = 0.70) than the reaction catalyzed by HY zeolite (X = 0.11), primarily because of the dominant hydrogenation observed with the former catalyst. In the absence of H2 as a co-reactant, the acidic γ-Al2O3 support in Pt/γ-Al2O3 evidently catalyzed all the classes of reactions catalyzed by HY zeolite.

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Acknowledgments

We thank Anna Hjelmeland and Jennifer Heelan for help with gas chromatography and Ryan Limbo, Kevin Tay, and Jonathan Doan for help with the catalytic reaction experiments. Fellowships to support RCR and TN were provided by the Ernest Gallo Endowed Chair in Viticulture and Enology and by Chevron, respectively. An Agilent Technologies Foundation Research Project Gift provided a GC7890 Refinery Gas Analyzer.

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Authors and Affiliations

  1. Department of Chemical Engineering and Materials Science, University of California, Davis, CA, 95616, USA

    Tarit Nimmanwudipong, Ron C. Runnebaum, David E. Block & Bruce C. Gates

  2. Department of Viticulture and Enology, University of California, Davis, CA, 95616, USA

    Susan E. Ebeler & David E. Block

Authors
  1. Tarit Nimmanwudipong
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  2. Ron C. Runnebaum
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  3. Susan E. Ebeler
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  4. David E. Block
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  5. Bruce C. Gates
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Correspondence to Bruce C. Gates.

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Nimmanwudipong, T., Runnebaum, R.C., Ebeler, S.E. et al. Upgrading of Lignin-Derived Compounds: Reactions of Eugenol Catalyzed by HY Zeolite and by Pt/γ-Al2O3 . Catal Lett 142, 151–160 (2012). https://doi.org/10.1007/s10562-011-0759-z

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  • DOI: https://doi.org/10.1007/s10562-011-0759-z

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