Projects per year
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.
Original language | English |
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Pages (from-to) | 392-406 |
Journal | Sustainable Chemistry |
Volume | 2 |
Issue number | 3 |
DOIs | |
Publication status | Published - 28 Jul 2021 |
Keywords
- Bio-based solvents
- Green metrics
- Solvent substitution
- Platform molecules
- safer solvents
Projects
- 1 Finished
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ReSolve: Renewable Solvents with high Performance in application and improved toxicity profile
Clark, J. H. (Principal investigator), Farmer, T. J. (Co-investigator) & Hunt, A. J. (Co-investigator)
1/06/17 → 30/11/20
Project: Research project (funded) › Research