Bank security dye packs

Synthesis, isolation, and characterization of chlorinated products of bleached 1-(methylamino)anthraquinone

James M. Egan, Michael Rickenbach, Kim E. Mooney, Chris S. Palenik, Rebecca Golombeck, Karl T. Mueller

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Banknote evidence is often submitted after a suspect has attempted to disguise or remove red dye stain that has been released because of an anti-theft device that activates after banknotes have been unlawfully removed from bank premises. Three chlorinated compounds have been synthesized as forensic chemical standards to indicate bank security dye bleaching as a suspect's intentional method for masking a robbery involving dye pack release on banknotes. A novel, facile synthetic method to provide three chlorinated derivatives of 1-(methylamino)anthraquinone (MAAQ) is presented. The synthetic route involved Ultra Clorox™ bleach as the chlorine source, iron chloride as the catalyst, and MAAQ as the starting material and resulted in a three-component product mixture. Two mono-chlorinated isomers (2-chloro-1-(methylamino) anthraquinone and 4-chloro-1-(methylamino)anthraquinone) and one di-chlorinated compound (2,4-dichloro-1-(methylamino)anthraquinone) of the MAAQ parent molecule were detected by gas chromatography mass spectrometry (GC-MS), and subsequently isolated by liquid chromatography (LC) with postcolumn fraction collection. Although GC-MS is sensitive enough to detect all of the chlorinated products, it is not definitive enough to identify the structural isomers. Liquid-state nuclear magnetic resonance (NMR) spectroscopy was utilized to elucidate structurally the ortho- and para-mono-chlorinated isomers once enough material was properly isolated. A reaction mechanism involving iron is proposed to explain the presence of chlorinated MAAQ species on stolen banknotes after attempted bleaching.

Original languageEnglish (US)
Pages (from-to)1276-1283
Number of pages8
JournalJournal of Forensic Sciences
Volume51
Issue number6
DOIs
StatePublished - Nov 1 2006

Fingerprint

Anthraquinones
Coloring Agents
Gas Chromatography-Mass Spectrometry
Iron
Theft
Sodium Hypochlorite
Chlorine
Liquid Chromatography
Chlorides
Magnetic Resonance Spectroscopy
Equipment and Supplies

All Science Journal Classification (ASJC) codes

  • Pathology and Forensic Medicine
  • Genetics

Cite this

Egan, James M. ; Rickenbach, Michael ; Mooney, Kim E. ; Palenik, Chris S. ; Golombeck, Rebecca ; Mueller, Karl T. / Bank security dye packs : Synthesis, isolation, and characterization of chlorinated products of bleached 1-(methylamino)anthraquinone. In: Journal of Forensic Sciences. 2006 ; Vol. 51, No. 6. pp. 1276-1283.
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Bank security dye packs : Synthesis, isolation, and characterization of chlorinated products of bleached 1-(methylamino)anthraquinone. / Egan, James M.; Rickenbach, Michael; Mooney, Kim E.; Palenik, Chris S.; Golombeck, Rebecca; Mueller, Karl T.

In: Journal of Forensic Sciences, Vol. 51, No. 6, 01.11.2006, p. 1276-1283.

Research output: Contribution to journalArticle

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AU - Egan, James M.

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