Byrne, Fergal, Clark, James Hanley orcid.org/0000-0002-5860-2480, Angelici, Carlo et al. (2 more authors) (2021) Greenness Assessment and Synthesis for the Bio-Based Production of the Solvent 2,2,5,5-Tetramethyloxolane (TMO). Sustainable Chemistry. pp. 392-406. ISSN 2673-4079
Abstract
2,2,5,5-tetramethyloxolane (TMO) has recently been identified and demonstrated as a safer solvent to replace toluene, THF, and hydrocarbons in a handful of applications. Herein, several bio-based routes to TMO are presented and assessed for greenness, assisted by the CHEM21 Metrics Toolkit and BioLogicTool plots. Using glucose as a common starting point, two chemocatalytic routes and two biochemical routes to TMO were identified and the pathways compared using the aforementioned tools. In addition, bio-based TMO was synthesised via one of these routes; from methyl levulinate supplied by Avantium, a by-product of the sugar dehydration step during the production of 2,5-furandicarboxylic acid. First, methyl levulinate underwent triple methylation using methyl magnesium chloride (MeMgCl) to yield 2,5-dimethylhexane-2,5-diol (DHL) in high yields of 89.7%. Then DHL was converted to high purity TMO (>98.5%) by cyclodehydration using H-BEA zeolites based on the previously reported approach. Bio-based content of this TMO was confirmed by ASTM D6866-20 Method B and found to have 64% bio-based carbon, well above the threshold of 25% set by CEN/TC 411 standards and matching the anticipated content. This study represents the first demonstration of a bio-based synthesis of TMO and confirmation of bio-content by accepted standards.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Keywords: | Bio-based solvents,Green metrics,Solvent substitution,Platform molecules,safer solvents |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Funding Information: | Funder Grant number EUROPEAN COMMISSION 745450 |
Depositing User: | Pure (York) |
Date Deposited: | 29 Jul 2021 09:10 |
Last Modified: | 25 Jan 2025 00:10 |
Published Version: | https://doi.org/10.3390/suschem2030023 |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.3390/suschem2030023 |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:176636 |