In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation
In situ separation of a chiral target compound is realized for the first time as distillate on top of an integrated biocatalytic batch reactive distillation column. The applied reaction system is the racemic resolution of (R/S)-2-pentanol in a transesterification with propyl butyrate, which is catal...
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American Chemical Society
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Online Access: | http://hdl.handle.net/11420/3154 |
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fttuhamburg:oai:tore.tuhh.de:11420/3154 2023-08-20T04:02:23+02:00 In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation Kühn, Steffen Sluyter, Gerrit Christlieb, Marc-Andreas Heils, Rene Stöbener, Anne-Kathrin Christine Kleber, Joscha Smirnova, Irina Liese, Andreas 2017-06-07 http://hdl.handle.net/11420/3154 en eng American Chemical Society Industrial & engineering chemistry research 1520-5045 Industrial and Engineering Chemistry Research 22 (56): 6451-6461 (2017-06-07) http://hdl.handle.net/11420/3154 2-s2.0-85021454451 570: Biowissenschaften Biologie 620: Ingenieurwissenschaften 620 570 Journal Article Other 2017 fttuhamburg 2023-07-28T09:22:43Z In situ separation of a chiral target compound is realized for the first time as distillate on top of an integrated biocatalytic batch reactive distillation column. The applied reaction system is the racemic resolution of (R/S)-2-pentanol in a transesterification with propyl butyrate, which is catalyzed by immobilized Candida antarctica lipase B (Novozym435). Biocatalyst integration is realized in baskets of wire gauze catalytic packings as column internals. The equilibrium limited reaction is shifted to the product side by fractional distillation of low boiling propanol and the target compound (S)-2-pentanol. Increased molar fractions up to x(S)-2-PeOH = 65 ± 4% with an enantiomeric excess of 90 ± 4% and 51 ± 3% overall conversion are reached for (S)-2-pentanol. Feasibility of the reaction system is investigated in our preselection tool. This tool is developed to evaluate predefined operation conditions in the column setup for transesterification reactions based on criteria regarding biocatalyst stability and boiling point differences between the reactants. The subsequently selected reaction of (R/S)-2-pentanol with propyl butyrate is successfully carried out in a batch reactive distillation column with in situ separation of our target compound (S)-2-pentanol. In contrast to current examples in the literature, this clearly demonstrates the possibility of one-pot target compound isolation within chiral synthesis applying biocatalytic reactive distillation. Article in Journal/Newspaper Antarc* Antarctica TUHH Open Research (TORE - Technische Universität Hamburg) Industrial & Engineering Chemistry Research 56 22 6451 6461 |
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Open Polar |
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TUHH Open Research (TORE - Technische Universität Hamburg) |
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fttuhamburg |
language |
English |
topic |
570: Biowissenschaften Biologie 620: Ingenieurwissenschaften 620 570 |
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570: Biowissenschaften Biologie 620: Ingenieurwissenschaften 620 570 Kühn, Steffen Sluyter, Gerrit Christlieb, Marc-Andreas Heils, Rene Stöbener, Anne-Kathrin Christine Kleber, Joscha Smirnova, Irina Liese, Andreas In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation |
topic_facet |
570: Biowissenschaften Biologie 620: Ingenieurwissenschaften 620 570 |
description |
In situ separation of a chiral target compound is realized for the first time as distillate on top of an integrated biocatalytic batch reactive distillation column. The applied reaction system is the racemic resolution of (R/S)-2-pentanol in a transesterification with propyl butyrate, which is catalyzed by immobilized Candida antarctica lipase B (Novozym435). Biocatalyst integration is realized in baskets of wire gauze catalytic packings as column internals. The equilibrium limited reaction is shifted to the product side by fractional distillation of low boiling propanol and the target compound (S)-2-pentanol. Increased molar fractions up to x(S)-2-PeOH = 65 ± 4% with an enantiomeric excess of 90 ± 4% and 51 ± 3% overall conversion are reached for (S)-2-pentanol. Feasibility of the reaction system is investigated in our preselection tool. This tool is developed to evaluate predefined operation conditions in the column setup for transesterification reactions based on criteria regarding biocatalyst stability and boiling point differences between the reactants. The subsequently selected reaction of (R/S)-2-pentanol with propyl butyrate is successfully carried out in a batch reactive distillation column with in situ separation of our target compound (S)-2-pentanol. In contrast to current examples in the literature, this clearly demonstrates the possibility of one-pot target compound isolation within chiral synthesis applying biocatalytic reactive distillation. |
format |
Article in Journal/Newspaper |
author |
Kühn, Steffen Sluyter, Gerrit Christlieb, Marc-Andreas Heils, Rene Stöbener, Anne-Kathrin Christine Kleber, Joscha Smirnova, Irina Liese, Andreas |
author_facet |
Kühn, Steffen Sluyter, Gerrit Christlieb, Marc-Andreas Heils, Rene Stöbener, Anne-Kathrin Christine Kleber, Joscha Smirnova, Irina Liese, Andreas |
author_sort |
Kühn, Steffen |
title |
In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation |
title_short |
In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation |
title_full |
In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation |
title_fullStr |
In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation |
title_full_unstemmed |
In situ separation of the chiral target compound (S)-2-pentanol in biocatalytic reactive distillation |
title_sort |
in situ separation of the chiral target compound (s)-2-pentanol in biocatalytic reactive distillation |
publisher |
American Chemical Society |
publishDate |
2017 |
url |
http://hdl.handle.net/11420/3154 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
Industrial & engineering chemistry research 1520-5045 Industrial and Engineering Chemistry Research 22 (56): 6451-6461 (2017-06-07) http://hdl.handle.net/11420/3154 2-s2.0-85021454451 |
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Industrial & Engineering Chemistry Research |
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56 |
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22 |
container_start_page |
6451 |
op_container_end_page |
6461 |
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1774712820568424448 |