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Chemoselective derivatisation and ultrahigh resolution mass spectrometry for the determination of hydroxyl functional groups within complex bio-oils
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Palacio Lozano, Diana Catalina, Jones, Hugh E., Barrow, Mark P. and Wills, Martin (2023) Chemoselective derivatisation and ultrahigh resolution mass spectrometry for the determination of hydroxyl functional groups within complex bio-oils. RSC advances, 13 (26). pp. 17727-17741. doi:10.1039/D3RA02779A ISSN 2046-2069.
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WRAP-chemoselective-derivatisation-ultrahigh-resolution-mass-spectrometry-determination-hydroxyl-functional-groups-complex-bio-oils-2023.pdf - Published Version - Requires a PDF viewer. Available under License Creative Commons Attribution. Download (2664Kb) | Preview |
Official URL: https://doi.org/10.1039/D3RA02779A
Abstract
Bio-oils are a renewable alternative resource for the production of fine chemicals and fuels. Bio-oils are characterised by a high content of oxygenated compounds with a diverse array of different chemical functionalities. Here, we performed a chemical reaction to transform the hydroxyl group of the various components in a bio-oil prior to characterisation with ultrahigh resolution mass spectrometry (UHRMS). The derivatisations were first evaluated using twenty lignin representative standards with different structural features. Our results indicate a highly chemoselective transformation of the hydroxyl group despite the presence of other functional groups. Mono- and di-acetate products were observed in acetone–acetic anhydride (acetone–Ac2O) mixtures for non-sterically hindered phenols, catechols and benzene diols. Dimethyl sulfoxide–Ac2O (DMSO–Ac2O) reactions favoured the oxidation of primary and secondary alcohols and the formation of methylthiomethyl (MTM) products of phenols. The derivatisations were then performed in a complex bio-oil sample to gain insights into the hydroxyl group profile of the bio-oil. Our results indicate that the bio-oil before derivatisation is composed of 4500 elemental compositions containing 1–12 oxygen atoms. After the derivatisation in DMSO–Ac2O mixtures, the total number of compositions increased approximately five-fold. The reaction was indicative of the variety of hydroxyl group profiles within the sample in particular the presence of phenols that were ortho and para substituted, non-hindered phenols (about 34%), aromatic alcohols (including benzylic and other non-phenolic alcohols) (25%), and aliphatic alcohols (6.3%) could be inferred. Phenolic compositions are known as coke precursors in catalytic pyrolysis and upgrading processes. Thus, the combination of chemoselective derivatisations in conjunction with UHRMS can be a valuable resource to outline the hydroxyl group profile in elemental chemical compositions in complex mixtures.
Item Type: | Journal Article | ||||||||||||
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Subjects: | Q Science > QD Chemistry T Technology > TP Chemical technology |
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Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||||||||||
Library of Congress Subject Headings (LCSH): | Biomass energy , Hydroxyl group, Mass spectrometry , Catalysis | ||||||||||||
Journal or Publication Title: | RSC advances | ||||||||||||
Publisher: | RSC | ||||||||||||
ISSN: | 2046-2069 | ||||||||||||
Official Date: | 12 June 2023 | ||||||||||||
Dates: |
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Volume: | 13 | ||||||||||||
Number: | 26 | ||||||||||||
Page Range: | pp. 17727-17741 | ||||||||||||
DOI: | 10.1039/D3RA02779A | ||||||||||||
Status: | Peer Reviewed | ||||||||||||
Publication Status: | Published | ||||||||||||
Access rights to Published version: | Open Access (Creative Commons) | ||||||||||||
Date of first compliant deposit: | 2 August 2023 | ||||||||||||
Date of first compliant Open Access: | 2 August 2023 | ||||||||||||
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