Debromination of hexabromobenzene by its co-grinding with CaO

A hexabromobenzene (HBB, C6Br6) powder was subjected to co-grinding with excess CaO powder in air using a planetary ball mill to investigate mechanochemical debromination of the HBB sample. The reaction proceeds smoothly with an increase in both grinding time and molar ratio of CaO addition. The co-grinding enables us to debrominate HBB, forming CaBr2, C and CaCO3 besides excess CaO in the product. CaBr2 in the product tends to absorb moisture from the atmosphere to form CaBr2•nH2O. The reaction yield is quantitatively evaluated by measuring the amount of water-soluble bromide through water washing and the amount of unreacted HBB through toluene washing. It is found that almost 100% of debromination is achieved by 6 h grinding with the molar ratio kept constant at 2:1. Radicals are detected in the ground products, possibly due to rupture in the covalent bonds of C–C and C–Br in HBB.