Greenness Assessment and Synthesis for the Bio-Based Production of the Solvent 2,2,5,5-Tetramethyloxolane (TMO)
| Autor: | James H. Clark, Fergal Byrne, Ed de Jong, Carlo Angelici, Thomas J. Farmer |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2021 |
| Předmět: |
safer solvent
platform molecules 010405 organic chemistry Chemistry Chemical technology Bio based TP1-1185 Methyl levulinate 010402 general chemistry 01 natural sciences Toluene Environmental technology. Sanitary engineering 0104 chemical sciences Solvent chemistry.chemical_compound Yield (chemistry) Green metrics green metrics Organic chemistry solvent substitution bio-based solvents TD1-1066 |
| Zdroj: | Sustainable Chemistry, Vol 2, Iss 23, Pp 392-406 (2021) Sustainable Chemistry Volume 2 Issue 3 Pages 23-406 |
| ISSN: | 2673-4079 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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