Greenness Assessment and Synthesis for the Bio-Based Production of the Solvent 2,2,5,5-Tetramethyloxolane (TMO)

被引:11
作者
Byrne, Fergal P. [1 ]
Clark, James H. [1 ]
Angelici, Carlo [2 ]
de Jong, Ed [2 ]
Farmer, Thomas J. [1 ]
机构
[1] Univ York, Green Chem Ctr Excellence, Dept Chem, York YO10 5DD, North Yorkshire, England
[2] Avantium, Zekeringstr 29, NL-1014 BV Amsterdam, Netherlands
来源
SUSTAINABLE CHEMISTRY | 2021年 / 2卷 / 03期
关键词
bio-based solvents; safer solvent; green metrics; platform molecules; solvent substitution; ANAEROBIC-DIGESTION PROCESS; ACETYLENE CONVERSION; METHANE PRODUCTION; BIOMASS; ISOBUTANOL; OXIDATION; CHEMICALS; PEROXIDE; LCA;
D O I
10.3390/suschem2030023
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:392 / 406
页数:15
相关论文
共 41 条
[41]   The cumene process for phenol-acetone production [J].
Zakoshansky, V. M. .
PETROLEUM CHEMISTRY, 2007, 47 (04) :273-284