A solid hydrazine was prepared as a crystalline powder by reacting hydrazine hydrate (NH2NH2�H2O) with CO2 at high pressure. Its structure was determined by single crystal X-ray diffraction, which shows a zwitter-ionic form of NH3+NHCO2-. The solid hydrazine is quite stable at ambient conditions but is remarkably reactive due presumably to facile release of anhydrous hydrazine upon reacting, which can thus be used as a new synthetic alternative to toxic liquid hydrazine. Simple grinding of solid hydrazine and aldehydes, using a mortar and a pestle, resulted in the formation of azines as the sole products with greater than 97% yields. Complete conversion is typically accomplished at 25? within 24 h, without using solvents or additives. The reaction was completed within 3 h when the reaction temperature increased to 80 ?. The solid-state reaction via simple grinding not only showed high selectivity but also did not generate any waste other than water and CO2, which provides an environmentally benign process for preparing a wide range of organic materials.

Organic synthesis in the solid state: Selective formation of azines by grinding solid hydrazine with aldehydes

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.