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The hydrodeoxygenation of bioderived furans into alkanes

Nature Chemistry volume 5, pages 428–432 (2013)Cite this article

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A Corrigendum to this article was published on 22 May 2013

A Corrigendum to this article was published on 22 May 2013

This article has been updated

Abstract

The conversion of biomass into fuels and chemical feedstocks is one part of a drive to reduce the world's dependence on crude oil. For transportation fuels in particular, wholesale replacement of a fuel is logistically problematic, not least because of the infrastructure that is already in place. Here, we describe the catalytic defunctionalization of a series of biomass-derived molecules to provide linear alkanes suitable for use as transportation fuels. These biomass-derived molecules contain a variety of functional groups, including olefins, furan rings and carbonyl groups. We describe the removal of these in either a stepwise process or a one-pot process using common reagents and catalysts under mild reaction conditions to provide n-alkanes in good yields and with high selectivities. Our general synthetic approach is applicable to a range of precursors with different carbon content (chain length). This allows the selective generation of linear alkanes with carbon chain lengths between eight and sixteen carbons.

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Figure 1: Organocatalysed routes to chain extended furfurals.
Figure 2: Removal of exocyclic unsaturation.
Figure 3: Divergent pathway leads to different products.
Figure 4: Conversion of carbon chain extended furans into polyketones and n-alkanes.
Figure 5: One-pot synthesis of n-nonane.

Change history

  • 26 April 2013

    In the version of this Article originally published, the reaction conditions given in Figure 3 for conversion of compound 2 to compound 4 were incorrect, and should have been stated as 'Acetic acid/H2O, 100°C, 3 h'; this has now been corrected in the HTML and PDF versions of this Article.

  • 03 May 2013

    In the version of this Article originally published, references to certain compound numbers in the Methods section were incorrect: Under the heading 'General experimental' "...conversion of 3 into n-nonane..." should have read "...conversion of 2 into n-nonane...". In 'Conversion of A into 2,5,8-nonanetrione 4', "... solvent removed in vacuo to yield 3..." should have read "... solvent removed in vacuo to yield 4...". In 'Conversion of B into 2,5,8-nonanetrione 4', "... solvent removed in vacuo to yield 3..." should have read "... solvent removed in vacuo to yield 4...". These errors have been corrected in the HTML and PDF versions of the Article.

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Acknowledgements

The authors acknowledge financial support from the Laboratory Research and Development (LDRD) program at Los Alamos National Laboratory.

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Authors and Affiliations

  1. Chemistry Division, MS J582, Los Alamos National Laboratory, Los Alamos, 87545, New Mexico, USA

    Andrew D. Sutton & John C. Gordon

  2. Department of Chemistry, University of Guelph, Guelph, N1G 2W1, Ontario, Canada

    Fraser D. Waldie & Marcel Schlaf

  3. Biosciences Division, MS E529, Los Alamos National Laboratory, Los Alamos, 87545, New Mexico, USA

    Ruilian Wu & Louis A. ‘Pete’ Silks III

Authors
  1. Andrew D. Sutton
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  2. Fraser D. Waldie
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  3. Ruilian Wu
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  4. Marcel Schlaf
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  5. Louis A. ‘Pete’ Silks III
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  6. John C. Gordon
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Contributions

A.D.S. made the initial discovery. A.D.S., M.S., L.A.S. and J.C.G. conceived and designed the experiments. A.D.S. and F.D.W. performed the experiments. R.W. and L.A.S. contributed materials. A.D.S. and J.C.G. co-wrote the paper. All authors discussed the results and provided input for the manuscript.

Corresponding authors

Correspondence to Andrew D. Sutton or John C. Gordon.

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The authors declare no competing financial interests.

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Sutton, A., Waldie, F., Wu, R. et al. The hydrodeoxygenation of bioderived furans into alkanes. Nature Chem 5, 428–432 (2013). https://doi.org/10.1038/nchem.1609

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