Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst

The atom-efficient esterification of phosphoric acid was investigated for the selective synthesis of phosphate mono-esters using an acid treated niobium oxide catalyst, avoiding the use of amines as is common in literature. Kinetic studies revealed that the heterogeneous catalyst exhibited higher se...

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Main Authors: Jens Wéry, Sofia Radelicki, Thomas J.N. Hooper, Margot Houbrechts, Kwinten Janssens, Wouter Stuyck, Dimitrios Sakellariou, Dirk E. De Vos
Format: Article
Language:English
Published: Elsevier 2025-06-01
Series:Tetrahedron Green Chem
Online Access:http://www.sciencedirect.com/science/article/pii/S2773223125000020
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author Jens Wéry
Sofia Radelicki
Thomas J.N. Hooper
Margot Houbrechts
Kwinten Janssens
Wouter Stuyck
Dimitrios Sakellariou
Dirk E. De Vos
author_facet Jens Wéry
Sofia Radelicki
Thomas J.N. Hooper
Margot Houbrechts
Kwinten Janssens
Wouter Stuyck
Dimitrios Sakellariou
Dirk E. De Vos
author_sort Jens Wéry
collection DOAJ
description The atom-efficient esterification of phosphoric acid was investigated for the selective synthesis of phosphate mono-esters using an acid treated niobium oxide catalyst, avoiding the use of amines as is common in literature. Kinetic studies revealed that the heterogeneous catalyst exhibited higher selectivity for mono-esters compared to homogeneous acid catalysts, as supported by calculation of the relative reactivity of mono-ester and phosphoric acid with different catalysts. To characterize the catalyst, its Hammett acidity value (H0) was determined, while solid state 31P NMR enabled studying the adsorption of H3PO4. Due to the mild acidity of the niobium oxide, alcohols with acid-sensitive functions, including substituted double bonds, could be phosphorylated, enabling the synthesis of surfactants such as oleyl phosphate.
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institution Kabale University
issn 2773-2231
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publishDate 2025-06-01
publisher Elsevier
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series Tetrahedron Green Chem
spelling doaj-art-6eabf9f2dd28407caf6cfcc1842831f32025-01-21T04:13:25ZengElsevierTetrahedron Green Chem2773-22312025-06-015100063Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalystJens Wéry0Sofia Radelicki1Thomas J.N. Hooper2Margot Houbrechts3Kwinten Janssens4Wouter Stuyck5Dimitrios Sakellariou6Dirk E. De Vos7Centre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCentre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCentre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCentre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCentre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCentre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCentre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumCorresponding author.; Centre for Membrane Separations, Adsorption, Catalysis and Spectroscopy for Sustainable Solutions (cMACS), Department of Microbial and Molecular Systems (M2S), KU Leuven, Celestijnenlaan 200F, Post Box 2454, 3001, Leuven, BelgiumThe atom-efficient esterification of phosphoric acid was investigated for the selective synthesis of phosphate mono-esters using an acid treated niobium oxide catalyst, avoiding the use of amines as is common in literature. Kinetic studies revealed that the heterogeneous catalyst exhibited higher selectivity for mono-esters compared to homogeneous acid catalysts, as supported by calculation of the relative reactivity of mono-ester and phosphoric acid with different catalysts. To characterize the catalyst, its Hammett acidity value (H0) was determined, while solid state 31P NMR enabled studying the adsorption of H3PO4. Due to the mild acidity of the niobium oxide, alcohols with acid-sensitive functions, including substituted double bonds, could be phosphorylated, enabling the synthesis of surfactants such as oleyl phosphate.http://www.sciencedirect.com/science/article/pii/S2773223125000020
spellingShingle Jens Wéry
Sofia Radelicki
Thomas J.N. Hooper
Margot Houbrechts
Kwinten Janssens
Wouter Stuyck
Dimitrios Sakellariou
Dirk E. De Vos
Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst
Tetrahedron Green Chem
title Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst
title_full Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst
title_fullStr Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst
title_full_unstemmed Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst
title_short Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst
title_sort selective synthesis of phosphate mono esters with an acidic modified niobium oxide catalyst
url http://www.sciencedirect.com/science/article/pii/S2773223125000020
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