Reports: B748384-B7: Polymerizing Alkenes with Polar Functional Groups: New Polymerization Methods for Functional, Hyperbranched Fuel Additives with Ester, Ether, and Amide Linkages

Robert T. Mathers , Pennsylvania State University New Kensington

During the third year of this Type B grant, four undergraduate students in engineering and science disciplines investigated the polymerization of olefins. These students conducted research in the summer and spent 15-30 hrs/week in the lab.  Two of these students will be entering medical school in the next year.  During the last three years of this grant, I have published 3 papers in peer-reviewed journals with 8 undergraduates as coauthors.

Over the past several years, we have been investigating methods for polymerizing cyclic and acyclic alkenes. These include bicyclic alkenes, such as norbornene derivatives, and cyclic dienes, such as cyclohexadiene. The synthesis and subsequent polymerization of 1,3-cyclohexadiene (1,3-CHD) from plant oils was investigated via metathesis and isomerization reactions. The metathesis reaction required no plant oil purification, minimal catalyst loading, no organic solvents, and simple product recovery by distillation. After treating soybean oil with a ruthenium metathesis catalyst, the resulting 1,4-cyclohexadiene (1,4-CHD) was isomerized with a ruthenium hydride complex. The isomerization reaction was conducted for 1 h in neat 1,4-CHD with [1,4-CHD]/[RuH] ratios as high as 5000. The isomerization and subsequent polymerization of the renewable 1,3-CHD was examined as a two-step sequence and as a one-step cascade reaction. The polymerization was catalyzed with nickel(II)acetylacetonate/methaluminoxane in neat monomer, hydrogenated d-limonene, and toluene. The resulting polymers were characterized by FTIR spectroscopy, differential scanning Calorimetry (DSC), and thermogravimetric analysis (TGA).


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