Mechanochemically Assisted Synthesis of Hexaazatriphenylenehexacarbonitrile
Wilm Pickhardt, Maximilian Wohlgemuth, Sven Grätz, Lars Borchardt
Abstract
1,4,5,8,9,11-hexaazatriphenylenehexacarbonitrile (HAT CN) was synthesized mechanochemically at room temperature. The coupling of hexaketocyclohexane and diaminomaleonitrile was conducted in 10 min by vibratory ball milling. The effects of milling parameters, acids, dehydrating agents, and liquid-assisted grinding were rationalized. With 67%, the yield of this mechanochemical approach exceeds that of state-of-the-art wet-chemical syntheses while being superior with respect to time-, resource-, and energy-efficiency as quantified via green metrics.
Topics & Concepts
ChemistryMechanochemistryGrindingBall millYield (engineering)Chemical engineeringOrganic chemistryMetallurgyMaterials scienceEngineeringPhenothiazines and Benzothiazines Synthesis and ActivitiesQuinazolinone synthesis and applicationsCrystallography and molecular interactions