Participation of Strong H-Bonding to Acidic Groups Contributes to the Intense Sorption of the Anionic Munition, Nitrotriazolone (NTO) to the Carbon, Filtrasorb 400

Details

• Personal Author:
  Abdelraheem W ; Meng L ; Pignatello JJ ; Seenthia N ; Xu W
• Description:
  5-Nitro-1,2-dihydro-3H-1,2,4-triazin-3-one ("nitrotriazolone," NTO) is an insensitive munition compound used in modern weaponry. It poses a potential threat to soil and water quality at relevant sites due to its physical properties that cause high mobility in the environment. NTO is polar and predominantly monoanionic (NTO-) at environmental pH (pKa1 = 3.64 and pKa2 = 11.06; determined by two independent methods in this study). Nevertheless, NTO- sorbs strongly to the carbon, Filtrasorb 400 (Freundlich coefficient KF = 1.26 × 104 Ln µmol1-n kg-1 at pH 9.5). We present evidence that sorption is contributed by the interaction of NTO- with functional groups of similar acidity on the carbon to form exceptionally strong, negative charge-assisted hydrogen bonds, (-)CAHB, written (-N-···H+···-O-), where -N- is the deprotonated N of NTO, and -O- represents a deprotonated surface group. Behaviors consistent with (-)CAHB include (1) a "hump" in the pH-sorption profile centered around pH 4, where maximal complexation is expected to occur; (2) an apparent approx.2.4-unit upward shift in pKa1 due to the enhanced H-bond strength; (3) the consumption of a proton from water to form the complex; and (4) sorption suppression by competing (-)CAHB-capable solutes. Anion exchange played a minor role. The findings help advance our understanding of weak acids sorption by carbonaceous materials. [Description provided by NIOSH]
• Subjects:
  Coal Coal Mining Ergonomics Hearing Loss Hearing Loss, Noise-Induced Mining Noise Noise, Occupational Occupational Health Personal Protective Equipment Safety

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• Keywords:
  Activated Carbon Adsorption Author Keywords: Adsorption Charge-assisted Hydrogen Bond Environmental Contamination Environmental Technology Hydrogen Ion Activity Insensitive Munition Compounds Low-barrier Hydrogen Bond Munitions Industry Short Strong Hydrogen Bond

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• ISSN:
  0013-936X
• Document Type:
  Text
• Genre:
  Journal Article
• Place as Subject:
  Boston Region [OSHA] ; Chicago Region [OSHA] ; Connecticut ; Ohio ; Pennsylvania ; Philadelphia Region [OSHA]
• CIO:
  National Institute for Occupational Safety and Health (NIOSH)
• Division:
  HELD - Health Effects Laboratory Division
• Topic:
  Workplace Safety & Health
• Location:
  North America
• Volume:
  58
• Issue:
  46
• NIOSHTIC Number:
  nn:20070390
• Citation:
  Environ Sci Technol 2024 Nov; 58(46):20719-20728
• Contact Point Address:
  Joseph J. Pignatello - Department of Environmental Science and Forestry, The Connecticut Agricultural Experimental Station, New Haven, Connecticut 06511, United States
• Email:
  Joseph.Pignatello@ct.gov
• CAS Registry Number:
  932-64-9
• Federal Fiscal Year:
  2025
• Peer Reviewed:
  True
• Source Full Name:
  Environmental Science and Technology
• Collection(s):
  National Institute for Occupational Safety and Health
• Main Document Checksum:
  urn:sha-512:e61d0306f5776a2e5c244c0c035dd8dc3597476a6e9d7facaa0dc63c4c35279cd6ffdc78deb56d09496ddd875eaf128805f4bc8c500da6b5b59211f70dee5bc1
• Download URL:
  https://stacks.cdc.gov/view/cdc/208617/cdc_208617_DS1.pdf
• File Type:
  [PDF - 3.59 MB ]