Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation
Schlipkoeter KE, Betke T, Kleber J, Gröger H, Liese A. Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation. Organic and Biomolecular Chemistry . 2020;18(39):7862-7867. Fatty alcohols are important products in chemical...
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Royal Soc Chemistry
2020
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ftubbiepub:oai:pub.uni-bielefeld.de:2948631 2023-05-15T13:40:40+02:00 Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation Schlipkoeter, Kim E. Betke, Tobias Kleber, Joscha Gröger, Harald Liese, Andreas 2020 https://pub.uni-bielefeld.de/record/2948631 eng eng Royal Soc Chemistry info:eu-repo/semantics/altIdentifier/doi/10.1039/d0ob01561j info:eu-repo/semantics/altIdentifier/issn/1477-0520 info:eu-repo/semantics/altIdentifier/issn/1477-0539 info:eu-repo/semantics/altIdentifier/wos/000579572100015 info:eu-repo/semantics/altIdentifier/pmid/32975273 https://pub.uni-bielefeld.de/record/2948631 info:eu-repo/semantics/closedAccess http://purl.org/coar/resource_type/c_6501 info:eu-repo/semantics/article doc-type:article text 2020 ftubbiepub https://doi.org/10.1039/d0ob01561j 2022-02-08T22:37:14Z Schlipkoeter KE, Betke T, Kleber J, Gröger H, Liese A. Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation. Organic and Biomolecular Chemistry . 2020;18(39):7862-7867. Fatty alcohols are important products in chemical industry to be used in the formulation of surfactants and lubricants. This work describes a two step approach for the production of myristyl alcohol under neat conditions by combining a lipase catalyzed esterification of myristic acid and myristyl alcohol with a ruthenium catalyzed hydrogenation of the intermediate myristyl myristate. The esterification was carried out in a bubble column reactor with the commercial immobilized lipase B fromCandida antarcticaas a biocatalyst, while the hydrogenation was conducted under pressurized conditions being catalyzed by the homogeneous chemocatalyst Ru-Macho-BH. By investigating the reaction steps separately, comparable reaction rates were found for the esterification of short chain and long chain alcohols. Additionally, the hydrogen pressure could be reduced to 35 bar compared to the current industrial Lurgi process. Characterization of cross interactions by the reactants myristic acid and sodium myristate in the hydrogenation demonstrates that the metal catalyst was completely deactivated, even at a low amount of 0.5 mol% of myristic acid. Complete conversion of myristic acid in the esterification with equal amounts of myristic acid and myristyl alcohol was obtained, overcoming any limitation in the hydrogenation. In comparison to the Lurgi process starting also from fatty acid and fatty alcohols, the chemoenzymatic two step reaction sequence could be realized at lower reaction temperatures of 60 and 100 degrees C as well as lower hydrogen pressures of 35 bar. Article in Journal/Newspaper Antarc* PUB - Publications at Bielefeld University Organic & Biomolecular Chemistry 18 39 7862 7867 |
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PUB - Publications at Bielefeld University |
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English |
description |
Schlipkoeter KE, Betke T, Kleber J, Gröger H, Liese A. Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation. Organic and Biomolecular Chemistry . 2020;18(39):7862-7867. Fatty alcohols are important products in chemical industry to be used in the formulation of surfactants and lubricants. This work describes a two step approach for the production of myristyl alcohol under neat conditions by combining a lipase catalyzed esterification of myristic acid and myristyl alcohol with a ruthenium catalyzed hydrogenation of the intermediate myristyl myristate. The esterification was carried out in a bubble column reactor with the commercial immobilized lipase B fromCandida antarcticaas a biocatalyst, while the hydrogenation was conducted under pressurized conditions being catalyzed by the homogeneous chemocatalyst Ru-Macho-BH. By investigating the reaction steps separately, comparable reaction rates were found for the esterification of short chain and long chain alcohols. Additionally, the hydrogen pressure could be reduced to 35 bar compared to the current industrial Lurgi process. Characterization of cross interactions by the reactants myristic acid and sodium myristate in the hydrogenation demonstrates that the metal catalyst was completely deactivated, even at a low amount of 0.5 mol% of myristic acid. Complete conversion of myristic acid in the esterification with equal amounts of myristic acid and myristyl alcohol was obtained, overcoming any limitation in the hydrogenation. In comparison to the Lurgi process starting also from fatty acid and fatty alcohols, the chemoenzymatic two step reaction sequence could be realized at lower reaction temperatures of 60 and 100 degrees C as well as lower hydrogen pressures of 35 bar. |
format |
Article in Journal/Newspaper |
author |
Schlipkoeter, Kim E. Betke, Tobias Kleber, Joscha Gröger, Harald Liese, Andreas |
spellingShingle |
Schlipkoeter, Kim E. Betke, Tobias Kleber, Joscha Gröger, Harald Liese, Andreas Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
author_facet |
Schlipkoeter, Kim E. Betke, Tobias Kleber, Joscha Gröger, Harald Liese, Andreas |
author_sort |
Schlipkoeter, Kim E. |
title |
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
title_short |
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
title_full |
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
title_fullStr |
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
title_full_unstemmed |
Fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
title_sort |
fatty alcohol synthesis from fatty acids at mild temperature by subsequent enzymatic esterification and metal-catalyzed hydrogenation |
publisher |
Royal Soc Chemistry |
publishDate |
2020 |
url |
https://pub.uni-bielefeld.de/record/2948631 |
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Antarc* |
genre_facet |
Antarc* |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1039/d0ob01561j info:eu-repo/semantics/altIdentifier/issn/1477-0520 info:eu-repo/semantics/altIdentifier/issn/1477-0539 info:eu-repo/semantics/altIdentifier/wos/000579572100015 info:eu-repo/semantics/altIdentifier/pmid/32975273 https://pub.uni-bielefeld.de/record/2948631 |
op_rights |
info:eu-repo/semantics/closedAccess |
op_doi |
https://doi.org/10.1039/d0ob01561j |
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Organic & Biomolecular Chemistry |
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18 |
container_issue |
39 |
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7862 |
op_container_end_page |
7867 |
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1766138340412751872 |