Selective and mild oxyfunctionalization of model polyolefins

Nicole K. Boaen, Marc A. Hillmyer

Research output: Contribution to journalArticlepeer-review

34 Scopus citations

Abstract

The direct oxyfunctionalization of a model polyolefin, polyethylene-alt-propylene (PEP), was achieved utilizing a straightforward, mild process. In the presence of a manganese complex, manganese meso-tetra-2,6-dichlorophenylporphyrin acetate (Mn(TDCPP)OAc), imidazole, a phase transfer agent, and potassium peroxymonosulfate (Oxone), PEP was functionalized under ambient conditions without chain degradation. The primary oxidation products contained tertiary alcohols and ketones based on IR, 1H NMR, 13C NMR, and DEPT 13C NMR spectroscopy of the oxyfunctionalized products. The oxyfunctionalization of squalane, a small molecule, structural analogue of PEP, was also demonstrated. Spectroscopic analyses of the main products from the squalane oxidation were nearly identical with the functional groups identified in the PEP oxidation products. The degree of functionalization was modulated by changing the relative concentration of the oxidant, Oxone. The degree of functionalization and the thermal properties are reported for these new polymeric materials.

Original languageEnglish (US)
Pages (from-to)7027-7034
Number of pages8
JournalMacromolecules
Volume36
Issue number19
DOIs
StatePublished - Sep 23 2003

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