Article | Published:

The hydrodeoxygenation of bioderived furans into alkanes

Nature Chemistry volume 5, pages 428432 (2013) | Download Citation

  • 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.

  • Compound C9H10O2

    (E)-4-(5-Methyl-2-furanyl)-3-butene-2-one

  • Compound C9H10O3

    (E)-4-[5-(Hydroxymethyl)-2-furanyl]-3-butene-2-one

  • Compound C15H14O5

    (E,E)-1,5-Bis(5-hydroxymethyl-2-furanyl)-1,4-pentadiene-3-one

  • Compound C14H18O4

    (E)-Ethyl-7-(5-methyl-2-furanyl)-5-oxohept-6-enoate

  • Compound C9H12O2

    4-(5-Methyl-2-furanyl)-2-butanone

  • Compound C9H12O3

    4-[5-(Hydroxy)-2-furanyl]-2-butanone

  • Compound C9H16O3

    4-[Tetrahydro-5-(hydroxymethyl)-2-furanyl]-2-butanone

  • Compound C9H14O3

    2,5,8-Nonanetrione

  • Compound C9H20

    Nonane

  • Compound C15H18O5

    1,5-Bis[5-(hydroxymethyl-2-furanyl]pentan-3-one

  • Compound C15H22O5

    2,5,8,11,14-Pentadecanepentone

  • Compound C15H32

    Pentadecane

  • Compound C14H20O4

    Ethyl-7-(5-methyl-2-furanyl)-5-oxoheptanoate

  • Compound C12H18O5

    5,8,11-Trioxododecanoic acid

  • Compound C12H26

    Dodecane

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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.

Author information

Affiliations

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

    • Andrew D. Sutton
    •  & John C. Gordon
  2. Department of Chemistry, University of Guelph, Guelph, Ontario, Canada N1G 2W1

    • Fraser D. Waldie
    •  & Marcel Schlaf
  3. Biosciences Division, MS E529, Los Alamos National Laboratory, Los Alamos, New Mexico 87545, USA

    • Ruilian Wu
    •  & Louis A. ‘Pete’ Silks III

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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.

Competing interests

The authors declare no competing financial interests.

Corresponding authors

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

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DOI

https://doi.org/10.1038/nchem.1609

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