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Corey M. Parada - The Ritter Reaction on Polyisobutylene Polymers and Oligomers: A Potential Route Towards Aliphatic Acrylamides

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Corey M. Parada - The Ritter Reaction on Polyisobutylene Polymers and Oligomers: A Potential Route Towards Aliphatic Acrylamides

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Corey M. Parada

Ph.D. Candidate

The University of Southern Mississippi

Phone: 512-433-0827

Co-Authors: Robson F. Storey

 

Abstract

 

Telechelic polyisobutylenes (PIB) find widespread use in fuel and lubricatings oils, sealants, and adhesives. Recently, telechelic PIBs have been synthesized via a process known as end quenching, in which living PIB cations are reacted with a quenching molecule at full IB conversion thereby introducing a functional group to the end of the chain. One method of end quenching that has not been investigated is quenching via the Ritter reaction, which utilizes a nitrile in the presence of a carbocation to form an amide via a nitrilium ion intermediate. Herein, we report our attempts at PIB chain end functionalization via the Ritter reaction under end quenching conditions and classical Ritter conditions using various PIB substrates, nitriles, and acid catalysts. When performed on small molecule
analogs of PIB, the Ritter reaction proceeded smoothly and the expected acrylamide was isolated in high yields. When polymeric PIB substrates were used, the Ritter-type addition of the nitrile was not observed, and isolated products indicated loss of chain end fidelity via carbocationic rearrangement or no reaction, presumably due to the immiscibility of the nitrile and the PIB substrate.

 

Biography

 

Corey Parada is a Ph.D. Candidate working under the direction of Dr. Robson F. Storey, where his main research areas are rubber thermosets, composites, and macromolecular engineering for advanced applications. As a senior graduate student, Corey has extensive experience in the synthesis, purification, and characterization of small molecules and polymers, and also physical testing of rubber and composite thermosets. He will be graduating in the Spring of 2018.

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