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Isolation and Identification of 3,3′,5,5′-Tetrabis(Tert-Butyl)Stilbenequinone from Polyethylene Closures Containing Titanium Dioxide and Butylated Hydroxytoluene

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Abstract

A yellow compound was isolated from commercially available, discolored, polyethylene ophthalmic closures containing titanium dioxide and butylated hydroxytoluene (I). This compound was present at 7.46 ppm (w/w). It was identified by UV, IR, and mass spectra as 3,3′,5,5′-tetrabis(tert-butyl)stilbenequinone (II), a dimer of I. Further structural confirmation was obtained by NMR. Formation of II is catalyzed by titanium dioxide.

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Research and Development, Schering Corp., Bloomfield, NJ 07003

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