Year: 2024
Type: article
Abstract: Adiponitrile (ADN) has wide applications, especially in the polymer industry. With the substantial and increasing global demand for ADN, effective production of ADN using safe and abundant starting materials is highly desirable but very challenging. Herein, we discovered that CuBr, combined with 1,10-phenanthroline (phen), could effectively promote the ammoxidation reaction of cyclohexanone to ADN with a yield of >99% using aqueous ammonia as the nitrogen source and O 2 as the terminal oxidant under mild reaction conditions (80 °C, 5 atm O 2 ). Moreover, cyclic ketones with various carbon numbers and substituent groups could also be converted into the corresponding dinitrile products with high yields. A detailed mechanistic study revealed that the reaction proceeded through a radical-mediated pathway, and the reason for the high selectivity to ADN was discussed. This study offers a new, simple, and cost-effective route to produce ADN and other dinitrile products.
DOI: 10.1021/jacs.4c14875
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Funders: National Natural Science Foundation of China, Chinese Academy of Sciences, Youth Innovation Promotion Association of the Chinese Academy of Sciences, University of Chinese Academy of Sciences, Institute of Chemistry, Chinese Academy of Sciences, National Key Research and Development Program of China, Youth Innovation Promotion Association, Beijing National Laboratory for Molecular Sciences
OpenAlex ID: W4405573826