Isolation and identification of 3,3',5,5'-tetrabis(tert-butyl)stilbenequinone from polyethylene closures containing titanium dioxide and butylated hydroxytoluene.
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.
D002084:Butylated Hydroxytoluene; D055598:Chemical Phenomena; D002621:Chemistry; D004349:Drug Packaging; D011095:Polyethylenes / Q000032:analysis*; D013267:Stilbenes / Q000032:analysis* / Q000302:isolation & purification; D014025:Titanium
D011095:Polyethylenes; D013267:Stilbenes; D002084:Butylated Hydroxytoluene; C020512:3,3',5,5'-tetrabis(tert-butyl)stilbenequinone; D014025:Titanium