A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors
A continuous enzyme-catalyzed acylation process for the selective preparation of monoacylated Vitamin A precursors starting from a 1,6-diol on a large scale is reported. Screenings led to the selection of the commercially available immobilized lipase Chirazyme L2-C2 (lipase B from Candida antarctica...
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ftdoajarticles:oai:doaj.org/article:d15f489fb2994eb891e4f8d989b0ed68 2023-05-15T13:33:57+02:00 A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors Bernard Orsat Beat Wirz Stefan Bischof 1999-12-01T00:00:00Z https://doaj.org/article/d15f489fb2994eb891e4f8d989b0ed68 DE EN FR ger eng fre Swiss Chemical Society https://www.chimia.ch/chimia/article/view/3191 https://doaj.org/toc/0009-4293 https://doaj.org/toc/2673-2424 0009-4293 2673-2424 https://doaj.org/article/d15f489fb2994eb891e4f8d989b0ed68 CHIMIA, Vol 53, Iss 12 (1999) Chemistry QD1-999 article 1999 ftdoajarticles 2022-12-31T13:49:03Z A continuous enzyme-catalyzed acylation process for the selective preparation of monoacylated Vitamin A precursors starting from a 1,6-diol on a large scale is reported. Screenings led to the selection of the commercially available immobilized lipase Chirazyme L2-C2 (lipase B from Candida antarctica) as the biocatalyst, different vinyl acylates as the acylating agents, and acetone as the co-solvent. Using a mixture of 70% (v/v) acetone and acylating agent allowed to increase the substrate concentration from 10 to 30% (w/w). Using a small fixed-bed reactor, this continuous process produced monoacylated product with >99% yield and >97% selectivity for the primary hydroxy group. The robustness of this system under different conditions was investigated. Consequently, the stability of the biocatalyst could be greatly improved by adding a protective pre-column and by adding small amounts of organic base and antioxidant to the substrate solution. This optimized laboratory process was used to selectively prepare monoacylated compounds in kilogram scales over one hundred days with only a minor decrease in conversion efficiency. The process was also implemented in an up-scaled mini plant for the continuous production on a kilogram-per-day scale, reproducing the results previously obtained on smaller laboratory scales. Article in Journal/Newspaper Antarc* Antarctica Directory of Open Access Journals: DOAJ Articles |
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Directory of Open Access Journals: DOAJ Articles |
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German English French |
topic |
Chemistry QD1-999 |
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Chemistry QD1-999 Bernard Orsat Beat Wirz Stefan Bischof A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors |
topic_facet |
Chemistry QD1-999 |
description |
A continuous enzyme-catalyzed acylation process for the selective preparation of monoacylated Vitamin A precursors starting from a 1,6-diol on a large scale is reported. Screenings led to the selection of the commercially available immobilized lipase Chirazyme L2-C2 (lipase B from Candida antarctica) as the biocatalyst, different vinyl acylates as the acylating agents, and acetone as the co-solvent. Using a mixture of 70% (v/v) acetone and acylating agent allowed to increase the substrate concentration from 10 to 30% (w/w). Using a small fixed-bed reactor, this continuous process produced monoacylated product with >99% yield and >97% selectivity for the primary hydroxy group. The robustness of this system under different conditions was investigated. Consequently, the stability of the biocatalyst could be greatly improved by adding a protective pre-column and by adding small amounts of organic base and antioxidant to the substrate solution. This optimized laboratory process was used to selectively prepare monoacylated compounds in kilogram scales over one hundred days with only a minor decrease in conversion efficiency. The process was also implemented in an up-scaled mini plant for the continuous production on a kilogram-per-day scale, reproducing the results previously obtained on smaller laboratory scales. |
format |
Article in Journal/Newspaper |
author |
Bernard Orsat Beat Wirz Stefan Bischof |
author_facet |
Bernard Orsat Beat Wirz Stefan Bischof |
author_sort |
Bernard Orsat |
title |
A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors |
title_short |
A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors |
title_full |
A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors |
title_fullStr |
A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors |
title_full_unstemmed |
A Continuous Lipase-Catalyzed Acylation Process for the Large-Scale Production of Vitamin A Precursors |
title_sort |
continuous lipase-catalyzed acylation process for the large-scale production of vitamin a precursors |
publisher |
Swiss Chemical Society |
publishDate |
1999 |
url |
https://doaj.org/article/d15f489fb2994eb891e4f8d989b0ed68 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_source |
CHIMIA, Vol 53, Iss 12 (1999) |
op_relation |
https://www.chimia.ch/chimia/article/view/3191 https://doaj.org/toc/0009-4293 https://doaj.org/toc/2673-2424 0009-4293 2673-2424 https://doaj.org/article/d15f489fb2994eb891e4f8d989b0ed68 |
_version_ |
1766047415965581312 |