Silylation of diamines for subsequent reaction with carbon dioxide

INOR 798

Anna Y. O'Brien, obrienay@lemoyne.edu, Joseph Lee, Cailin M. Daly, and Adam S. Colburn. Department of Chemistry and Physics, Le Moyne College, 1419 Salt Springs Rd., Syracuse, NY 13214
Diisocyanates, such as TDI and MDI, are precursors in the manufacturing of polyurethanes. Large scale synthesis of diisocyanates typically relies on the highly toxic gaseous phosgene or its various substitutes. Alternative synthetic routes to phosgenation are desirable, and include the carbonylation of amines with carbon dioxide. Multiple variations of the carbonylation method have been reported. Here, metallation of silylated diamines and subsequent reaction of the metal amido compounds with carbon dioxide are expected to yield the corresponding diisocyanates. Toward this goal, 2,4-diaminotoluene and 1,5-diaminonaphthalene have been silylated using butyllithium and chlorotrimethylsilane.
 

Coordination Chemistry: Synthesis
7:00 PM-9:00 PM, Wednesday, August 19, 2009 Walter E. Washington Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Sci-Mix

Division of Inorganic Chemistry

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009