Recyclable nitration catalysts: An environmental and economical alternative to classic aromatic nitration

CHED 434

Brian C. Tlach, brian.tlach@loras.edu1, David J. Oostendorp, david.oostendorp@loras.edu1, and Predrag-Peter Ilich, pilich@csm.edu2. (1) Department of Chemistry, Loras College, 1450 Alta Vista Street, Box 1359, Dubuque, IA 52001--0178, (2) Department of Chemistry, College of Saint Mary, 7000 Mercy Road, Omaha, NE 68106
Lanthanide(III) triflates have been proven to be effective recyclable aromatic nitration catalysts providing an environmental friendly alternative to classical aromatic nitration. Products have been obtained for slightly activated, deactivated, and bare aromatics rings such as p-xylene, methyl-benzoate, or benzene. Yields have been limited, 8.9 % for benzene, when compared to literature values of greater than 95 % for the same substrate. To increase yields, solvents with polarity different from 1,2 dichloroethane such as tetrahydrofuran were used to increase the solubility of the catalyst in the reaction suspension. Highly activated aromatic rings were also used as substrates with different solvents to nitrate compounds that failed in previous studies. The ability to recycle the catalyst via aqueous work up was performed successful without any loss of yield.
 

Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, April 7, 2008 Morial Convention Center -- Hall A, Poster

Division of Chemical Education

The 235th ACS National Meeting, New Orleans, LA, April 6-10, 2008