Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach

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Journal of the American Chemical Society : JACS. 2017, 139(38), pp. 13487-13491. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/jacs.7b06957
Zusammenfassung

A dual catalysis approach enables selective functionalization of unconventional feedstocks composed of complex fatty acid mixtures with highly unsaturated portions like eicosapentaenoate (20:5) along with monounsaturated compounds. The degree of unsaturation is unified by selective heterogeneous hydrogenation on Pd/γ-Al2O3, complemented by effective activation to a homogeneous carbonylation catalyst [(dtbpx)PdH(L)]+ by addition of diprotonated diphosphine (dtbpxH2)(OTf)2. By this one-pot approach, neat 20:5 as a model substrate is hydrogenated to up to 80% to the monounsaturated analogue (20:1), this is functionalized to the desired C21 α,ω-diester building block with a linear selectivity of over 90%. This catalytic approach is demonstrated to be suitable for crude microalgae oil from Phaeodactylum tricornutum genetically engineered for this purpose, as well as tall oil, an abundant waste material. Both substrates were fully converted with an overall selectivity to the linear α,ω-diester of up to 75%.

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ISO 690HESS, Sandra K., Natalie S. SCHUNCK, Verena GOLDBACH, Daniela EWE, Peter G. KROTH, Stefan MECKING, 2017. Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach. In: Journal of the American Chemical Society : JACS. 2017, 139(38), pp. 13487-13491. ISSN 0002-7863. eISSN 1520-5126. Available under: doi: 10.1021/jacs.7b06957
BibTex
@article{Hess2017-09-27Valor-40500,
  year={2017},
  doi={10.1021/jacs.7b06957},
  title={Valorization of Unconventional Lipids from Microalgae or Tall Oil via a Selective Dual Catalysis One-Pot Approach},
  number={38},
  volume={139},
  issn={0002-7863},
  journal={Journal of the American Chemical Society : JACS},
  pages={13487--13491},
  author={Hess, Sandra K. and Schunck, Natalie S. and Goldbach, Verena and Ewe, Daniela and Kroth, Peter G. and Mecking, Stefan}
}
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    <dcterms:abstract xml:lang="eng">A dual catalysis approach enables selective functionalization of unconventional feedstocks composed of complex fatty acid mixtures with highly unsaturated portions like eicosapentaenoate (20:5) along with monounsaturated compounds. The degree of unsaturation is unified by selective heterogeneous hydrogenation on Pd/γ-Al&lt;sub&gt;2&lt;/sub&gt;O&lt;sub&gt;3&lt;/sub&gt;, complemented by effective activation to a homogeneous carbonylation catalyst [(dtbpx)PdH(L)]&lt;sup&gt;+&lt;/sup&gt; by addition of diprotonated diphosphine (dtbpxH&lt;sub&gt;2&lt;/sub&gt;)(OTf)&lt;sub&gt;2&lt;/sub&gt;. By this one-pot approach, neat 20:5 as a model substrate is hydrogenated to up to 80% to the monounsaturated analogue (20:1), this is functionalized to the desired C&lt;sub&gt;21&lt;/sub&gt; α,ω-diester building block with a linear selectivity of over 90%. This catalytic approach is demonstrated to be suitable for crude microalgae oil from Phaeodactylum tricornutum genetically engineered for this purpose, as well as tall oil, an abundant waste material. Both substrates were fully converted with an overall selectivity to the linear α,ω-diester of up to 75%.</dcterms:abstract>
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