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 journalArticlepeer-review

4 Scopus citations

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 2006

All Science Journal Classification (ASJC) codes

  • Pathology and Forensic Medicine
  • Genetics

Fingerprint Dive into the research topics of 'Bank security dye packs: Synthesis, isolation, and characterization of chlorinated products of bleached 1-(methylamino)anthraquinone'. Together they form a unique fingerprint.

Cite this