γ-Stearolactone ring-opening by zeolites for the production of branched saturated fatty acids

Jelle W. Bos; Job G. A. Vloedgraven; Sophie C. C. Wiedemann; Leo van Dongen; Roel C. J. Moonen; Bas Wels; Peter H. Berben; Bennie H. Reesink; Peter de Peinder; Eelco T. C. Vogt; Bert M. Weckhuysen

doi:10.1039/D4CY00782D

γ-Stearolactone ring-opening by zeolites for the production of branched saturated fatty acids

Jelle W. Bos, Job G. A. Vloedgraven, Sophie C. C. Wiedemann, Leo van Dongen, Roel C. J. Moonen, Bas Wels, Peter H. Berben, Bennie H. Reesink, Peter de Peinder, Eelco T. C. Vogt, Bert M. Weckhuysen^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

C₁₈ branched saturated fatty acids (BSFA) are used as ingredients in cosmetics and lubricants and are produced via the hydrogenation of C₁₈ branched unsaturated fatty acids (BUFA). Industrial-grade C₁₈ BUFA contain the odorous by-product γ-stearolactone (GSL), which must be removed by acid-catalysed ring-opening of GSL into oleic acid. Zeolites such as Y and beta can facilitate the ring-opening, but due to the dimensions of GSL the activity is expected to be limited by diffusion into the micropores. Hence, zeolites Y and beta were modified via hydrothermal treatment and acid leaching and used in the GSL ring-opening reaction. While modification of zeolite beta led to a reduction in acidity of more than 50%, the material displayed much-enhanced activity compared to the parent material. In a batch reactor steamed beta zeolites were able to convert all GSL within 2 h, compared to 5 h for the parent zeolite. Infrared spectroscopy studies of adsorbed pyridine reveal that likely a beneficial change in Brønsted/Lewis acid site ratio is responsible for the increased activity. Lewis acid sites in zeolites are known to catalyse double bond isomerisation, which could greatly enhance GSL conversion by reducing the reverse formation of GSL from oleic acid. We believe that these insights can be used to further improve GSL ring-opening activity and inspire research on the ring-opening of other biomass derived lactones.

Original language	English
Pages (from-to)	7037-7047
Number of pages	11
Journal	Catalysis Science and Technology
Volume	14
Issue number	24
Early online date	25 Sept 2024
DOIs	https://doi.org/10.1039/D4CY00782D
Publication status	Published - 21 Dec 2024

Bibliographical note

Publisher Copyright:
© 2024 The Royal Society of Chemistry.

Funding

The authors thank the Netherlands Organization for Scientific Research (NWO) for research funding. This work is part of the Launchpad for Innovative Future Technology (LIFT) programme of NWO (project number: ENPPS.LIFT.019.008). The project is co-financed by Cargill, BASF, VibSpec, and NWO. Dr. Matteo Monai (Utrecht University, UU) is thanked for his help with the writing of the manuscript. The authors thank Dr. Andrei Gurinov and Joyce Kromwijk (both from UU) for performing Al MAS NMR measurements and Dr. Yadolah Ganjkhanlou (UU) for help with the quantification of the pyridine-FT-IR spectroscopy data. Leon Smit, Wim Otten, and Henk de Heij (all from Cargill) are thanked for their help with the analyses of the reactants and reaction products.

Funders	Funder number
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Launchpad for Innovative Future Technology	ENPPS.LIFT.019.008

Access to Document

10.1039/D4CY00782DLicence: CC BY

d4cy00782dFinal published version, 1.89 MBLicence: CC BY

Cite this

Bos, J. W., Vloedgraven, J. G. A., Wiedemann, S. C. C., van Dongen, L., Moonen, R. C. J., Wels, B., Berben, P. H., Reesink, B. H., de Peinder, P., Vogt, E. T. C., & Weckhuysen, B. M. (2024). γ-Stearolactone ring-opening by zeolites for the production of branched saturated fatty acids. Catalysis Science and Technology, 14(24), 7037-7047. https://doi.org/10.1039/D4CY00782D

@article{56ad3413292e4550896bf7f11619a30c,

title = "γ-Stearolactone ring-opening by zeolites for the production of branched saturated fatty acids",

abstract = "C18 branched saturated fatty acids (BSFA) are used as ingredients in cosmetics and lubricants and are produced via the hydrogenation of C18 branched unsaturated fatty acids (BUFA). Industrial-grade C18 BUFA contain the odorous by-product γ-stearolactone (GSL), which must be removed by acid-catalysed ring-opening of GSL into oleic acid. Zeolites such as Y and beta can facilitate the ring-opening, but due to the dimensions of GSL the activity is expected to be limited by diffusion into the micropores. Hence, zeolites Y and beta were modified via hydrothermal treatment and acid leaching and used in the GSL ring-opening reaction. While modification of zeolite beta led to a reduction in acidity of more than 50%, the material displayed much-enhanced activity compared to the parent material. In a batch reactor steamed beta zeolites were able to convert all GSL within 2 h, compared to 5 h for the parent zeolite. Infrared spectroscopy studies of adsorbed pyridine reveal that likely a beneficial change in Br{\o}nsted/Lewis acid site ratio is responsible for the increased activity. Lewis acid sites in zeolites are known to catalyse double bond isomerisation, which could greatly enhance GSL conversion by reducing the reverse formation of GSL from oleic acid. We believe that these insights can be used to further improve GSL ring-opening activity and inspire research on the ring-opening of other biomass derived lactones.",

author = "Bos, {Jelle W.} and Vloedgraven, {Job G. A.} and Wiedemann, {Sophie C. C.} and {van Dongen}, Leo and Moonen, {Roel C. J.} and Bas Wels and Berben, {Peter H.} and Reesink, {Bennie H.} and {de Peinder}, Peter and Vogt, {Eelco T. C.} and Weckhuysen, {Bert M.}",

note = "Publisher Copyright: {\textcopyright} 2024 The Royal Society of Chemistry.",

year = "2024",

month = dec,

day = "21",

doi = "10.1039/D4CY00782D",

language = "English",

volume = "14",

pages = "7037--7047",

journal = "Catalysis Science and Technology",

issn = "2044-4753",

publisher = "Royal Society of Chemistry",

number = "24",

}

TY - JOUR

T1 - γ-Stearolactone ring-opening by zeolites for the production of branched saturated fatty acids

AU - Bos, Jelle W.

AU - Vloedgraven, Job G. A.

AU - Wiedemann, Sophie C. C.

AU - van Dongen, Leo

AU - Moonen, Roel C. J.

AU - Wels, Bas

AU - Berben, Peter H.

AU - Reesink, Bennie H.

AU - de Peinder, Peter

AU - Vogt, Eelco T. C.

AU - Weckhuysen, Bert M.

PY - 2024/12/21

Y1 - 2024/12/21

N2 - C18 branched saturated fatty acids (BSFA) are used as ingredients in cosmetics and lubricants and are produced via the hydrogenation of C18 branched unsaturated fatty acids (BUFA). Industrial-grade C18 BUFA contain the odorous by-product γ-stearolactone (GSL), which must be removed by acid-catalysed ring-opening of GSL into oleic acid. Zeolites such as Y and beta can facilitate the ring-opening, but due to the dimensions of GSL the activity is expected to be limited by diffusion into the micropores. Hence, zeolites Y and beta were modified via hydrothermal treatment and acid leaching and used in the GSL ring-opening reaction. While modification of zeolite beta led to a reduction in acidity of more than 50%, the material displayed much-enhanced activity compared to the parent material. In a batch reactor steamed beta zeolites were able to convert all GSL within 2 h, compared to 5 h for the parent zeolite. Infrared spectroscopy studies of adsorbed pyridine reveal that likely a beneficial change in Brønsted/Lewis acid site ratio is responsible for the increased activity. Lewis acid sites in zeolites are known to catalyse double bond isomerisation, which could greatly enhance GSL conversion by reducing the reverse formation of GSL from oleic acid. We believe that these insights can be used to further improve GSL ring-opening activity and inspire research on the ring-opening of other biomass derived lactones.

AB - C18 branched saturated fatty acids (BSFA) are used as ingredients in cosmetics and lubricants and are produced via the hydrogenation of C18 branched unsaturated fatty acids (BUFA). Industrial-grade C18 BUFA contain the odorous by-product γ-stearolactone (GSL), which must be removed by acid-catalysed ring-opening of GSL into oleic acid. Zeolites such as Y and beta can facilitate the ring-opening, but due to the dimensions of GSL the activity is expected to be limited by diffusion into the micropores. Hence, zeolites Y and beta were modified via hydrothermal treatment and acid leaching and used in the GSL ring-opening reaction. While modification of zeolite beta led to a reduction in acidity of more than 50%, the material displayed much-enhanced activity compared to the parent material. In a batch reactor steamed beta zeolites were able to convert all GSL within 2 h, compared to 5 h for the parent zeolite. Infrared spectroscopy studies of adsorbed pyridine reveal that likely a beneficial change in Brønsted/Lewis acid site ratio is responsible for the increased activity. Lewis acid sites in zeolites are known to catalyse double bond isomerisation, which could greatly enhance GSL conversion by reducing the reverse formation of GSL from oleic acid. We believe that these insights can be used to further improve GSL ring-opening activity and inspire research on the ring-opening of other biomass derived lactones.

UR - http://www.scopus.com/inward/record.url?scp=85210129290&partnerID=8YFLogxK

U2 - 10.1039/D4CY00782D

DO - 10.1039/D4CY00782D

M3 - Article

SN - 2044-4753

VL - 14

SP - 7037

EP - 7047

JO - Catalysis Science and Technology

JF - Catalysis Science and Technology

IS - 24

ER -

γ-Stearolactone ring-opening by zeolites for the production of branched saturated fatty acids

Abstract

Bibliographical note

Funding

Access to Document

Other files and links

Fingerprint

Cite this