Aromatic dinitriles are useful building blocks, e.g., for polymers. A method to prepare these compounds from alcohols or aldehydes that are generated from biomass would be a helpful addition to sustainable chemistry.
Jiping Ma, Jie Xu, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, and colleagues have, for the first time, synthesized 2,5-dicyanofuran (pictured) from biomass-derived 2,5-diformylfuran in an efficient manner. 2,5-Diformylfuran can be readily synthesized from carbohydrates. The team then converted this compound to 2,5-diformylfuran dioxime using hydroxylamine. This intermediate was dehydrated using the solid acid catalyst Amberlyst-15 to give the desired 2,5-dicyanofuran in 82 % yield.
According to the researchers, the use of hydroxylamine instead of ammonia is key to the synthesis strategy, since it avoids polymerization side reactions. The synthesis avoids toxic reagents such as cyanides and allows the conversion of biomass resources to useful chemical building blocks.
- Efficient Synthesis of 2,5-Dicyanofuran from Biomass-Derived 2,5-Diformylfuran via an Oximation–Dehydration Strategy,
Yongming Xu, Xiuquan Jia, Jiping Ma, Jin Gao, Fei Xia, Xiaofang Li, Jie Xu,
ACS Sustainable Chem. Eng. 2018.