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...

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Published inJournal of pharmaceutical sciences Vol. 68; no. 7; p. 916
Main Authors Jagnandan, I, Daun, H, Ambrosio, T J, Gilbert, S G
Format Journal Article
LanguageEnglish
Published United States 01.07.1979
Subjects
Butylated Hydroxytoluene
Chemical Phenomena
Chemistry
Drug Packaging
Polyethylenes - analysis
Stilbenes - analysis
Stilbenes - isolation & purification
Titanium
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Summary: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.
ISSN:0022-3549
DOI:10.1002/jps.2600680738