PMID- 21296495
OWN - NLM
STAT- MEDLINE
DCOM- 20110531
LR  - 20110228
IS  - 1873-3336 (Electronic)
IS  - 0304-3894 (Linking)
VI  - 187
IP  - 1-3
DP  - 2011 Mar 15
TI  - Toxic pollutants emitted from thermal decomposition of phthalimide compounds.
PG  - 407-12
LID - 10.1016/j.jhazmat.2011.01.040 [doi]
AB  - Phthalimide (PI) and tetrahydrophthalimide (THPI) are two structurally similar 
      compounds extensively used as intermediates for the synthesis of variety of 
      industrial chemicals. This paper investigates the thermal decomposition of PI and 
      THPI under oxygen rich to oxygen lean conditions, quantifying the production of 
      toxicants and explaining their formation pathways. The experiments involved a 
      plug flow reactor followed by silica cartridges, activated charcoal trap and a 
      condenser, with the decomposition products identified and quantified by Fourier 
      transform infrared spectroscopy (FTIR), gas chromatography-mass spectrometry 
      (GC-MS) and micro gas chromatography (muGC). The density functional theory (DFT) 
      calculations served to obtain dissociation energies and reaction pathways, to 
      elucidate the reaction mechanism. The oxidation of PI and THPI produced several 
      toxic nitrogen-containing gases and volatile organic compounds, including 
      hydrogen cyanide, isocyanic acid, nitrogen oxides, benzonitrile, maleimide and 
      tentatively identified benzenemethanimine. The detection of dibenzo-p-dioxin (DD) 
      and dibenzofuran (DF) suggests potential formation of the toxic persistent 
      organic pollutants (POPs) in fires involving PI and THPI, in presence of a 
      chlorine source. The oxidation of THPI produced 2-cyclohexen-1-one, a toxic 
      unsaturated ketone. The results of the present study provide the data for 
      quantitative risk assessments of emissions of toxicants in combustion processes 
      involving PI and THPI.
CI  - Copyright (c) 2011 Elsevier B.V. All rights reserved.
FAU - Chen, Kai
AU  - Chen K
AD  - Process Safety and Environmental Protection Research Group, School of 
      Engineering, The University of Newcastle, Callaghan, New South Wales 2308, 
      Australia.
FAU - Mackie, John C
AU  - Mackie JC
FAU - Wojtalewicz, Dominika
AU  - Wojtalewicz D
FAU - Kennedy, Eric M
AU  - Kennedy EM
FAU - Dlugogorski, Bogdan Z
AU  - Dlugogorski BZ
LA  - eng
PT  - Journal Article
PT  - Research Support, Non-U.S. Gov't
DEP - 20110115
PL  - Netherlands
TA  - J Hazard Mater
JT  - Journal of hazardous materials
JID - 9422688
RN  - 0 (Environmental Pollutants)
RN  - 0 (Phthalimides)
SB  - IM
MH  - Environmental Pollutants/*analysis
MH  - Gas Chromatography-Mass Spectrometry
MH  - Oxidation-Reduction
MH  - Phthalimides/*chemistry
MH  - Spectroscopy, Fourier Transform Infrared
EDAT- 2011/02/08 06:00
MHDA- 2011/06/01 06:00
CRDT- 2011/02/08 06:00
PHST- 2010/12/03 00:00 [received]
PHST- 2011/01/11 00:00 [accepted]
PHST- 2011/02/08 06:00 [entrez]
PHST- 2011/02/08 06:00 [pubmed]
PHST- 2011/06/01 06:00 [medline]
AID - S0304-3894(11)00062-8 [pii]
AID - 10.1016/j.jhazmat.2011.01.040 [doi]
PST - ppublish
SO  - J Hazard Mater. 2011 Mar 15;187(1-3):407-12. doi: 10.1016/j.jhazmat.2011.01.040. 
      Epub 2011 Jan 15.