Year of Graduation

2020

Level of Access

Restricted Access Thesis

Department or Program

Chemistry

First Advisor

Richard Broene

Abstract

Linear alpha olefins are used as precursors of various products such as lubricants, detergents, shampoos, and other speciality chemicals. There are a variety of chemical methods for producing these linear alpha olefins, the most prevalent being the oligomerization of ethene. One such oligomerization process was invented by Shell Oil in the 1960s: The Shell Higher Olefins Process (or “SHOP”). Whilst the SHOP process is more efficient than previous methods, it still produces substantial amounts of long chain waste by-products. Previously, a cationic cobalt catalyst with a trimethylphosphite ligand successfully dimerized of 1-hexene to 1-dodecene. Unfortunately, due to the steric bulk of the supporting ligand, the catalyst did not yield a favourable product distribution, with 1,2 insertion dominating. This research project focused on the successful synthesis and coordination of various less bulky phenyl isocyanide supporting ligands to bis(η2-ethene)25-pentamethylcyclopentadienyl)cobalt(I). The synthesis of p-methoxy-, p-nitro-, p-bromo-, and p-fluorophenylisocyanides and conditions for mono-coordination to Cp*Co(ethene)2 are presented. Reaction optimization in the synthesis of both the phenyl isocyanide ligands and the neutral precatalyst bis (η2-ethene) (η5-pentamethylcyclopentadienyl)cobalt(I) was achieved during this project. Additionally, successful coordination of the 4-methoxy, fluoro and bromophenyl isocyanide supporting ligand to bis (η2-ethene) (η5-pentamethylcyclopentadienyl) cobalt(I) was achieved.

Restricted

Available only to users on the Bowdoin campus.

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