Unexpected oxidative cracking of Diformyltricyclodecanes under catalyst-free and ultra-low temperature

Abstract

The oxidative cracking of diformyltricyclodecanes (DFTD) to C6-C8 alkenes and alkenes were systematically studied in this work. A series of experiments was performed over a broad range of conditions (temperature: 40–60 °C; oxygen pressure: 0–1.0 Mpa; reaction time: 5–90 min, solvent selection) for exploring the reaction route and mechanism. Results show that the higher temperature and oxygen pressure, as well as tetrahydrofuran (THF) as solvent are of benefit to the generation of cracking products. In addition, the kinetics of this reaction was explored by the dynamic fitting. The obtained kinetics parameters demonstrate that the transformation of intermediate to cracking products possesses higher activation energy than to dicarboxyltricyclodecaneacids (DCTDA), showing that higher temperature is conducive to the generation of DFTD cracking products. This work firstly demonstrated that DFTD could be formed into C6-C8 alkenes containing the same as gasoline compound by the oxidative cracking, suggesting that the by-product of petroleum and coal could be transferred into fuels, this expanded the application of DCPD and will have significant and positive influence on the petroleum and coal chemical industry.