Oxyfunctionalization of Polystyrene Using Non-Heme Iron Catalysts
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The non-polar nature of polystyrene has allowed this material to be widely used in both industrial and household applications. This same property also limits its interactions with polar materials and its stability renders it slow to degrade in an environmental setting. Considering its widespread use in society, this makes polystyrene an environmental concern. The introduction of a limited number of polar groups along the backbone could increase its compatibility with polar materials as well as possibly rendering it biodegradable. The literature contains many reports of iron based catalysts that oxidize small molecule alkanes in moderate yields to introduce ketone or alcohol groups.1-3 In principle, the chemistry applicable to small molecules should also be applicable to their macromolecular analogues. This thesis used two such iron complexes, [(Fe(TPA)(MeCN)2] (OTf)2 and Fe(BPMEN)(OTf)2, to catalyze the oxidation of polystyrene using hydrogen peroxide as oxidant. The polymeric product was analyzed first by IR and if oxyfunctionalization was detected in the form of a carbonyl or hydroxyl peak, the material was further analyzed by DSC, GPC and 1H NMR. The results reported herein constitute a proof of principle for the use of iron based non-heme catalysts and hydrogen peroxide for the oxyfunctionalization of polystyrene.