Isolation and identification of 3,3',5,5'-tetrabis(tert-butyl)stilbenequinone from polyethylene closures containing titanium dioxide and butylated hydroxytoluene

J Pharm Sci. 1979 Jul;68(7):916-7. doi: 10.1002/jps.2600680738.

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.

MeSH terms

  • Butylated Hydroxytoluene
  • Chemical Phenomena
  • Chemistry
  • Drug Packaging*
  • Polyethylenes / analysis*
  • Stilbenes / analysis*
  • Stilbenes / isolation & purification
  • Titanium

Substances

  • Polyethylenes
  • Stilbenes
  • Butylated Hydroxytoluene
  • 3,3',5,5'-tetrabis(tert-butyl)stilbenequinone
  • Titanium