Sustainable Syntheses of Paracetamol and Ibuprofen from Biorenewable β-pinene

Joshua D. Tibbetts; Marc Hutchby; William B. Cunningham; Robert S. L. Chapman; Gabriele Kociok-Köhn; Matthew G. Davidson; Steven D. Bull

doi:10.1002/cssc.202300670

Sustainable Syntheses of Paracetamol and Ibuprofen from Biorenewable β-pinene

Joshua D. Tibbetts, Marc Hutchby, William B. Cunningham, Robert S. L. Chapman, Gabriele Kociok-Köhn, Matthew G. Davidson, Steven D. Bull^*

^*Corresponding author for this work

Chemistry

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Abstract

Scalable processes have been developed to convert β-pinene into 4-isopropenylcyclohexanone, which is then used as a feedstock for the divergent synthesis of sustainable versions of the common painkillers, paracetamol and ibuprofen. Both synthetic routes use Pd0 catalysed reactions to aromatize the cyclohexenyl rings of key intermediates to produce the benzenoid ring systems of both drugs. The potential of using bioderived 4-hydroxyacetophenone as a drop-in feedstock replacement to produce sustainable aromatic products is also discussed within a terpene biorefinery context.

Original language	English
Article number	e202300670
Number of pages	9
Journal	ChemSusChem
Volume	16
Issue number	21
Early online date	18 Jun 2023
DOIs	https://doi.org/10.1002/cssc.202300670
Publication status	Published - 8 Nov 2023

Bibliographical note

Funding Information:
We would like to thank EPSRC for funding this study through “Terpene‐based Manufacturing for Sustainable Chemical Feedstocks” EP/K014889 and the Centre for Doctoral Training in Sustainable Chemical Technologies (EP/L016354/1)

Keywords

biomass
biorefinery
ibuprofen
paracetamol
terpenes

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TibbettsJ2023SustainableFinal published version, 3.13 MBLicence: Creative Commons: Attribution (CC BY)

Cite this

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title = "Sustainable Syntheses of Paracetamol and Ibuprofen from Biorenewable β-pinene",

abstract = "Scalable processes have been developed to convert β-pinene into 4-isopropenylcyclohexanone, which is then used as a feedstock for the divergent synthesis of sustainable versions of the common painkillers, paracetamol and ibuprofen. Both synthetic routes use Pd0 catalysed reactions to aromatize the cyclohexenyl rings of key intermediates to produce the benzenoid ring systems of both drugs. The potential of using bioderived 4-hydroxyacetophenone as a drop-in feedstock replacement to produce sustainable aromatic products is also discussed within a terpene biorefinery context.",

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AU - Tibbetts, Joshua D.

AU - Hutchby, Marc

AU - Cunningham, William B.

AU - Chapman, Robert S. L.

AU - Kociok-Köhn, Gabriele

AU - Davidson, Matthew G.

AU - Bull, Steven D.

N1 - Funding Information: We would like to thank EPSRC for funding this study through “Terpene‐based Manufacturing for Sustainable Chemical Feedstocks” EP/K014889 and the Centre for Doctoral Training in Sustainable Chemical Technologies (EP/L016354/1)

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AB - Scalable processes have been developed to convert β-pinene into 4-isopropenylcyclohexanone, which is then used as a feedstock for the divergent synthesis of sustainable versions of the common painkillers, paracetamol and ibuprofen. Both synthetic routes use Pd0 catalysed reactions to aromatize the cyclohexenyl rings of key intermediates to produce the benzenoid ring systems of both drugs. The potential of using bioderived 4-hydroxyacetophenone as a drop-in feedstock replacement to produce sustainable aromatic products is also discussed within a terpene biorefinery context.

KW - biomass

KW - biorefinery

KW - ibuprofen

KW - paracetamol

KW - terpenes

U2 - 10.1002/cssc.202300670

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Sustainable Syntheses of Paracetamol and Ibuprofen from Biorenewable β-pinene

Abstract

Bibliographical note

Keywords

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