Reductive transformation of hexahydro-1,3,5-trinitro-1,3,5-triazine, octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine, and methylenedinitramine with elemental iron

Environmental Toxicology and Chemistry

Volumn 24, Issue 11, 2005, Pages 2812-2819

  Oh, Seok Young ^a   Cha, Daniel K ^a   Kim, Byung J ^b   Chiu, Pei C ^a  

^a UNIVERSITY OF DELAWARE   (United States)

^b US Army Engineering Research and Development Center   (United States)

Author keywords

Elemental iron; Hexahydro 1,3,5 trinitro 1,3,5 triazine; Methylenedinitramine; Octahydro 1,3,5,7 tetranitro 1,3,5,7 tetrazocine; Reduction

Indexed keywords

ESTERS; FORMALDEHYDE; IRON; NITROGEN COMPOUNDS; REACTION KINETICS; REDUCTION; SOIL POLLUTION; WATER POLLUTION;

ELEMENTAL IRON; HEXAHYDRO-1,3,5-TRINITRO-1,3,5-TRIAZINE; METHYLENEDINITRAMINE; OCTAHYDRO-1,3,5,7-TETRANITRO-1,3,5,7-TETRASOCINE;

EXPLOSIVES;

4 (2 HYDROXYETHYL) 1 PIPERAZINEETHANESULFONIC ACID; ACTIVATED CARBON; AMMONIA; BUFFER; CYCLONITE; EXPLOSIVE; FORMALDEHYDE; GRAPHITE; GROUND WATER; IRON; MAGNETITE; METHYLENEDINITRAMINE; NITROUS OXIDE; OCTAHYDRO 1,3,5,7 TETRANITRO 1,3,5,7 TETRAZOCINE; UNCLASSIFIED DRUG;

DEGRADATION; EXPLOSIVE;

ADSORPTION; ANAEROBIC BACTERIUM; ARTICLE; BATCH REACTOR; BIOTRANSFORMATION; CHEMICAL REACTION KINETICS; CLOSTRIDIUM; ELECTROCHEMICAL ANALYSIS; GAS CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; NONHUMAN; PHANEROCHAETE; PRIORITY JOURNAL; REDUCTION; RHODOCOCCUS; SOIL POLLUTION; WATER POLLUTION;

ADSORPTION; AMINES; AZOCINES; CATIONS, DIVALENT; FERROSOFERRIC OXIDE; FORMALDEHYDE; GRAPHITE; HETEROCYCLIC COMPOUNDS, 1-RING; IRON; KINETICS; NITRO COMPOUNDS; OXIDATION-REDUCTION; TRIAZINES;

BACTERIA (MICROORGANISMS); CLOSTRIDIUM; PHANEROCHAETE; RHODOCOCCUS;

EID: 27144509198     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/04-662R.1     Document Type: Article

References (61)

1. Akhavan J. 2004. The Chemistry of Explosives. Royal Society of Chemistry, Cambridge, UK.
2. Brannon JM, Pennington JC. 2002. Environmental fate and transport process descriptors for explosives. ERDC/ECTR-02-10. U.S. Army Engineering Research and Development Center, Vicksburg, MS.
3. Park J, Comfort SD, Shea PJ, Machacek TA. 2004. Remediating munitions-contaminated soil with zero-valent iron and cationic surfactants. J Environ Qual 33:1305-1313.
4. Concurrent Technologies. 1995. Pink water treatment options. Report SFIM-AEC-ETD-CR-95036. Technical Report. U.S. Army Environmental Center, Aberdeen Proving Ground, MD.
5. Urbanski T. 1984. Chemistry and Technology of Explosives, Vol 4. Pergamon, New York, NY, USA.
6. Yinon J. 1990. Toxicity and Metabolism of Explosives. CRC, Boca Raton, FL, USA.
7. Peters GT, Burton DT, Paulson RL, Turley SD. 1991. The acute and chronic toxicity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) to three freshwater invertebrates. Environ Toxicol Chem 10:1073-1081.
8. Burton DT, Turley SD, Peters GT. 1994. The toxicity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) to the fresh-water green-alga Selenastrum capricornutum. Water Air Soil Pollut 76: 449-457.
9. Burton DT, Turley SD, Peters GT. 1994. The acute and chronic toxicity of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) to the fathead minnow (Pimephales promelas). Chemosphere 29:567-579.
10. Gong P, Hawari J, Thiboutot S, Ampleman G, Sunahara GI. 2002. Toxicity of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) to soil microbes. Bull Environ Contam Toxicol 69:97-103.
11. Robidoux PY, Hawari J, Thiboutot S, Ampleman G, Sunahara GI. 2001. Chronic toxicity of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) in soil determined using the earthworm (Eisenia andrei) reproduction test. Environ Pollut 111:283-292.
12. McLellan W, Hartley WR, Brower M. 1988. Health advisory for hexahydro-1,3,5-trinitro-1,3,5-triazine. PB90-273533. Technical Report. Office of Drinking Water, U.S. Environmental Protection Agency, Washington, DC.
13. McLellan W, Hartley WR, Brower M. 1988. Health advisory for octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine. PB90-273525. Technical Report. Office of Drinking Water, U.S. Environmental Protection Agency, Washington, DC.
14. Heilmann HM, Wiesmann U, Stenstrom MK. 1996. Kinetics of the alkaline hydrolysis of high explosives RDX and HMX in aqueous solution and adsorbed to activated carbon. Environ Sci Technol 30:1485-1492.
15. Balakrishnan VK, Halasz A, Hawari J. 2003. Alkaline hydrolysis of the cyclic nitramine explosives RDX, HMX, and CL-20: New insight into degradation pathways obtained by the observation of novel intermediates. Environ Sci Technol 37:1838-1843.
16. Knackmuss HJ. 1996. Basic knowledge and perspectives of bioelimination of xenobiotic compounds. J Biotechnol 51:287-295.
17. Adrian NR, Sutherland K. 1998. RDX biodegradation by a methanogenic enrichment culture obtained from an explosives manufacturing wastewater treatment plant. USACERL Technical Report 99/15. Construction Engineering Research Laboratories, U.S. Army Corps of Engineers, Champaign, IL.
18. Doppalapudi RB, Sorial GA, Maloney SW. 2002. Electrochemical reduction of simulated munitions wastewater in a bench-scale batch reactor. Environ Eng Sci 19:115-130.
19. Bonin PML, Bejan D, Schutt L, Hawari J, Bunce NJ. 2004. Electrochemical reduction of hexahydro-1,3,5-trinitro-1,3,5-triazine in aqueous solutions. Environ Sci Technol 38:1595-1599.
20. Singh J, Comfort SD, Shea PJ. 1998. Remediating RDX-contaminated water and soil using zero-valent iron. J Environ Qual 27: 1240-1245.
21. Singh J, Comfort SD, Shea PJ. 1999. Iron-mediated remediation of RDX-contaminated water and soil under controlled Eh/pH. Environ Sci Technol 33:1488-1494.
22. Oh SY, Cha DK, Kim BJ, Chiu PC. 2002. Effect of adsorption to elemental iron on the transformation of 2,4,6-trinitrotoluene and hexahydro-1,3,5- trinitro-1,3,5-triazine in solution. Environ Toxicol Chem 21:1384-1389.
23. Oh SY, Cha DK, Chiu PC, Kim BJ. 2004. Conceptual comparison of pink water treatment technologies: Granular activated carbon, anaerobic fluidized bed, and zero-valent iron-Fenton process. Water Sci Technol 47:129-136.
24. Oh SY, Chiu PC, Kim BJ, Cha DK. 2003. Enhancing Fenton oxidation of TNT and RDX through pretreatment with zero-valent iron. Water Res 37:4275-4283.
25. Oh BT, Just CL, Alvarez PJJ. 2001. Hexahydro-1,3,5-trinitro-1,3,5- triazine mineralization by zero-valent iron and mixed anaerobic cultures. Environ Sci Technol 35:4341-4346.
26. Hundal LS, Singh J, Bier EL, Shea PJ, Comfort SD, Powers WL. 1997. Removal of TNT and RDX from water and soil using iron metal. Environ Pollut 97:55-64.
27. Young DM, Unkefer PJ, Ogden KL. 1997. Biotransformation of hexahydero-1,3,5-trinitro-1,3,5-triazine (RDX) by a prospective consortium and its most effective isolate Serratia marcescens. Biotechnol Bioeng 53:515-522.
28. Boopathy R, Gurgas M, Ullian J, Manning JF. 1998. Metabolism of explosive compounds by sulfate-reducing bacteria. Curr Microbiol 37:127-131.
29. Freedman DL, Sutherland KW. 1998. Biodegradation of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) under nitrate-reducing conditions. Water Sci Technol 38:33-40.
30. Zhang C, Hughes JB. 2003. Biodegradation pathway of hexahydro-1,3,5- trinitro-1,3,5-triazine (RDX) by Clostridium acetobutylicum cell-free extract. Chemosphere 50:665-671.
31. McCormick NG, Cornell JH, Kaplan AM. 1981. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine. Appl Environ Microbiol 42:817-823.
32. Hawari J, Halasz A, Sheremata T, Beaudet S, Groom C, Paquet L, Rhotir C, Ampleman G, Thiboutot S. 2000. Characterization of metabolites during biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) with anaerobic sludge. Appl Environ Microbiol 66:2652-2657.
33. Halasz A, Spain J, Paquet L, Beaulieu C, Hawari J. 2002. Insights into the formation and degradation mechanisms of methylene-dinitramine during the incubation of RDX with anaerobic sludge. Environ Sci Technol 36:633-638.
34. Bhushan B, Halasz A, Spain J, Thiboutot S, Ampleman G, Hawari J. 2002. Biotransformation of hexahyro-1,3,5-trinitro-1,3,5-triazine catalyzed by a NAD(P)H: Nitrate oxidoreductase from Aspergillus niger. Environ Sci Technol 36:3104-3108.
35. Zhiio JS, Halasz A, Paquet L, Beaulieu C, Hawari J. 2002. Biodegradation of hexahydro-1,3,5-trinitro-1,3,5-triazine and its mononitroso derivative hexahydro-1-nitroso-3,5-dinitro-1,3,5-triazine by Klebsiella pneumoniae strain SCZ-1 isolated from an anaerobic sludge. Appl Environ Microbiol 68:5336-5341.
36. Hawari J, Halasz A, Beaudet S, Paquet L, Ampleman G, Thiboutot S. 2001. Biotransformation routes of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine by municipal anaerobic sludge. Environ Sci Technol 35:70-75.
37. II bound to magnetite. Environ Sci Technol 38:1408-1414.
38. 0. Environ Sci Technol 38:6861-6866.
39. Burris DR, Campbell TJ, Manoranjan VS. 1995. Sorption of trichloroethylene and tetrachloroethylene in a batch reactive metallic iron-water system. Environ Sci Technol 29:2850-2855.
40. Allen-King RM, Halket RM, Burris DR. 1997. Reductive transformation and sorption of cis- and trans-1,2-dichloroethene in a metallic iron-water system. Environ Toxicol Chem 16:424-429.
41. Burris DR, Allen-King RM, Manoranjan VS, Campbell TJ, Loraine GA, Deng B. 1998. Chlorinated ethene reduction by cast iron: Sorption and mass transfer. J Environ Eng ASCE 124:1012-1019.
42. Perey JR, Chiu PC, Huang CP, Cha DK. 2002. Zero-valent iron pretreatment for enhancing the biodegradability of azo dyes. Water Environ Res 74:221-225.
43. Oh SY, Cha DK, Chiu PC. 2002. Graphite-mediated reduction of 2,4-dinitrotoluene with elemental iron. Environ Sci Technol 36: 2178-2184.
44. Oh SY, Cha DK, Kim BJ, Chiu PC. 2004. Reduction of nitroglycerin with cast iron: Pathway, kinetics, and mechanisms. Environ Sci Technol 38:3723-3730.
45. Summers WR. 1990. Characterization of formaldehyde and formaldehyde-releasing preservatives by combined reversed-phase cation-exchange high-performance liquid chromatography with postcolumn derivatization using Nash's reagent. Anal Chem 62: 1397-1402.
46. Hach. 1998. DR/2010 Spectrophotometer Handbook. Loveland, CO, USA.
47. Alowitz MJ, Scherer MM. 2002. Kinetics of nitrate, nitrite, and Cr(VI) reduction by iron metal. Environ Sci Technol 36:299-306.
48. Arnold WA, Ball WP, Roberts AL. 1999. Polychlorinated ethane reaction with zero-valent zinc: Pathway and rate control. J Contam Hydrol 40:183-200.
49. Schwarzenbach RP, Gschwend PM, Imboden DM. 1993. Environmental Organic Chemistry. John Wiley, New York, NY, USA.
50. Fournier D, Halasz A, Spain J, Fiurasek P, Hawari J. 2002. Determination of key metabolites during biodegradation of hexahydro-1,3,5-trinitro-1,3,5- triazine with Rhodococcus sp. strain DN22. Appl Environ Microbiol 68:166-172.
51. Fournier D, Halasz A, Spain J, Spanggord RJ, Bottaro JC, Hawari J. 2004. Biodegradation of the hexahydro-1,3,5-trinitro-1,3,5-triazine ring cleavage product 4-nitro-2,4-diazabutanal by Phanerochaete chrysosporium. Appl Environ Microbiol 70:1123-1128.
52. Fournier D, Halasz A, Thiboutot S, Ampleman G, Manno D, Hawari J. 2004. Biodegradation of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX) by Phanerochaete chrysosporium: New insight into the degradation pathway. Environ Sci Technol 38:4130-4133.
53. Cox RA. 1996. The acid-catalyzed decomposition of nitramide. Can J Chem 74:1779-1783.
54. Eckert-Maksic M, Maskill H, Zrinski I. 2001. Acidic and basic properties of nitramide, and the catalyzed decomposition of nitramide and related compounds: An ab inito theoretical investigation. J Chem Soc Perkin Trans 2:2147-2154.
55. Jafarpour B, Imhoff PT, Chiu PC. 2005. Quantification and modeling of 2,4-dinitrotoluene reduction with high-purity and cast iron. J Contam Hydrol 76:87-107.
56. Heijman CG, Grieder E, Holliger C, Schwarzenbach RP. 1995. Reduction of nitroaromatic compounds coupled to microbial iron reduction in laboratory aquifer columns. Environ Sci Technol 29: 775-783.
57. Klausen J, Tröber SP, Haderlein SB, Schwarzenbach RP. 1995. Reduction of substituted nitrobenzenes by Fe(II) in aqueous mineral suspensions. Environ Sci Technol 29:2396-2404.
58. Hofstetter TB, Heijman CG, Haderlein SB, Holliger C, Schwarzenbach RP. 1999. Complete reduction of TNT and other (poly)nitroromatic compounds under iron-reducing subsurface conditions. Environ Sci Technol 33:1479-1487.
59. McCormick ML, Bouwer EJ, Adriaens P. 2002. Carbon tetrachloride transformation in a model iron-reducing culture: Relative kinetics of biotic and abiotic reactions. Environ Sci Technol 36: 403-410.
60. Pecher K, Haderlein SB, Schwarzenbach RP. 2002. Reduction of polyhalogenated methanes by surface-bound Fe(II) in aqueous suspensions of iron oxides. Environ Sci Technol 36:1734-1741.
61. Cooper DC, Picardal FW, Schimmelmann A, Coby AJ. 2003. Chemical and biological interactions during nitrite and goethite reduction by Shewanella putrefaciens 200. Appl Environ Microbiol 69:3517-3525.