Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products
•DNAN undergoes regioselective reduction at the o-NO2 under abiotic and biotic conditions.•Physicochemical parameters (Sw, pKa, logKow, Kd) are provided for DNAN and its amine products.•Physicochemical behavior depends on type and position of substituent(s) on the aromatic ring.•Amine products of DN...
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| Veröffentlicht in: | Chemosphere (Oxford) 2015-01, Vol.119, p.16-23 |
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| creator | Hawari, J. Monteil-Rivera, F. Perreault, N.N. Halasz, A. Paquet, L. Radovic-Hrapovic, Z. Deschamps, S. Thiboutot, S. Ampleman, G. |
| description | •DNAN undergoes regioselective reduction at the o-NO2 under abiotic and biotic conditions.•Physicochemical parameters (Sw, pKa, logKow, Kd) are provided for DNAN and its amine products.•Physicochemical behavior depends on type and position of substituent(s) on the aromatic ring.•Amine products of DNAN irreversibly bind to soil under oxic conditions.
Several defense departments intend to replace 2,4,6-trinitrotoluene (TNT) in munitions formulations by the less sensitive 2,4-dinitroanisole (DNAN). To help understand environmental behavior and ecological risk associated with DNAN we investigated its key initial abiotic and biotic reaction routes and determined relevant physicochemical parameters (pKa, logKow, aqueous solubility (Sw), partition coefficient (Kd)) for the chemical and its products. Reduction of DNAN with either zero valent iron or bacteria regioselectively produced 2-amino-4-nitroanisole (2-ANAN) which, under strict anaerobic conditions, gave 2,4-diaminoanisole (DAAN). Hydrolysis under environmental conditions was insignificant whereas photolysis gave photodegradable intermediates 2-hydroxy-4-nitroanisole and 2,4-dinitrophenol. Physicochemical properties of DNAN and its amino products drastically depended on the type and position of substituent(s) on the aromatic ring. Sw followed the order (TNT |
| doi_str_mv | 10.1016/j.chemosphere.2014.05.047 |
| format | Article |
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Several defense departments intend to replace 2,4,6-trinitrotoluene (TNT) in munitions formulations by the less sensitive 2,4-dinitroanisole (DNAN). To help understand environmental behavior and ecological risk associated with DNAN we investigated its key initial abiotic and biotic reaction routes and determined relevant physicochemical parameters (pKa, logKow, aqueous solubility (Sw), partition coefficient (Kd)) for the chemical and its products. Reduction of DNAN with either zero valent iron or bacteria regioselectively produced 2-amino-4-nitroanisole (2-ANAN) which, under strict anaerobic conditions, gave 2,4-diaminoanisole (DAAN). Hydrolysis under environmental conditions was insignificant whereas photolysis gave photodegradable intermediates 2-hydroxy-4-nitroanisole and 2,4-dinitrophenol. Physicochemical properties of DNAN and its amino products drastically depended on the type and position of substituent(s) on the aromatic ring. Sw followed the order (TNT<DNAN<2-ANAN<4-ANAN<DAAN) whereas logKow followed the order (DAAN<4-ANAN<2-ANAN<DNAN<TNT). In soil, successive replacement of NO2 by NH2 in DNAN enhanced irreversible sorption and reduced bioavailability under oxic conditions. Although DNAN is more soluble than TNT, its lower hydrophobicity and its tendency to form aminoderivatives that sorb irreversibly to soil contribute to make it less toxic than the traditional explosive TNT.]]></description><identifier>ISSN: 0045-6535</identifier><identifier>EISSN: 1879-1298</identifier><identifier>DOI: 10.1016/j.chemosphere.2014.05.047</identifier><identifier>PMID: 25460743</identifier><language>eng</language><publisher>England: Elsevier Ltd</publisher><subject>2,4-Diaminoanisole ; 2,4-Dinitroanisole ; 2,4-Dinitrophenol - chemistry ; Anisoles - chemistry ; Anisoles - toxicity ; Bacteria ; Bioavailability ; Chromatography, High Pressure Liquid ; Chromatography, Ion Exchange ; Ecological risk assessment ; Explosive Agents - chemistry ; Explosive Agents - toxicity ; Explosive forming ; Hydrolysis ; Hydrophobic and Hydrophilic Interactions ; Hydrophobicity ; Insensitive munition ; Molecular Structure ; Phenylenediamines - chemistry ; Reduction ; Regioselectivity ; Risk ; Soil (material) ; Soil Pollutants - chemistry ; Soil Pollutants - toxicity ; Solubility ; Spectrophotometry ; TNT</subject><ispartof>Chemosphere (Oxford), 2015-01, Vol.119, p.16-23</ispartof><rights>2014 Elsevier Ltd</rights><rights>Copyright © 2014 Elsevier Ltd. All rights reserved.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c443t-50c94c00fd574f038bd22a2628afaab93e1af8f329296c5ad04129d7d322bff33</citedby><cites>FETCH-LOGICAL-c443t-50c94c00fd574f038bd22a2628afaab93e1af8f329296c5ad04129d7d322bff33</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S0045653514006894$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65534</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25460743$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hawari, J.</creatorcontrib><creatorcontrib>Monteil-Rivera, F.</creatorcontrib><creatorcontrib>Perreault, N.N.</creatorcontrib><creatorcontrib>Halasz, A.</creatorcontrib><creatorcontrib>Paquet, L.</creatorcontrib><creatorcontrib>Radovic-Hrapovic, Z.</creatorcontrib><creatorcontrib>Deschamps, S.</creatorcontrib><creatorcontrib>Thiboutot, S.</creatorcontrib><creatorcontrib>Ampleman, G.</creatorcontrib><title>Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products</title><title>Chemosphere (Oxford)</title><addtitle>Chemosphere</addtitle><description><![CDATA[•DNAN undergoes regioselective reduction at the o-NO2 under abiotic and biotic conditions.•Physicochemical parameters (Sw, pKa, logKow, Kd) are provided for DNAN and its amine products.•Physicochemical behavior depends on type and position of substituent(s) on the aromatic ring.•Amine products of DNAN irreversibly bind to soil under oxic conditions.
Several defense departments intend to replace 2,4,6-trinitrotoluene (TNT) in munitions formulations by the less sensitive 2,4-dinitroanisole (DNAN). To help understand environmental behavior and ecological risk associated with DNAN we investigated its key initial abiotic and biotic reaction routes and determined relevant physicochemical parameters (pKa, logKow, aqueous solubility (Sw), partition coefficient (Kd)) for the chemical and its products. Reduction of DNAN with either zero valent iron or bacteria regioselectively produced 2-amino-4-nitroanisole (2-ANAN) which, under strict anaerobic conditions, gave 2,4-diaminoanisole (DAAN). Hydrolysis under environmental conditions was insignificant whereas photolysis gave photodegradable intermediates 2-hydroxy-4-nitroanisole and 2,4-dinitrophenol. Physicochemical properties of DNAN and its amino products drastically depended on the type and position of substituent(s) on the aromatic ring. Sw followed the order (TNT<DNAN<2-ANAN<4-ANAN<DAAN) whereas logKow followed the order (DAAN<4-ANAN<2-ANAN<DNAN<TNT). In soil, successive replacement of NO2 by NH2 in DNAN enhanced irreversible sorption and reduced bioavailability under oxic conditions. Although DNAN is more soluble than TNT, its lower hydrophobicity and its tendency to form aminoderivatives that sorb irreversibly to soil contribute to make it less toxic than the traditional explosive TNT.]]></description><subject>2,4-Diaminoanisole</subject><subject>2,4-Dinitroanisole</subject><subject>2,4-Dinitrophenol - chemistry</subject><subject>Anisoles - chemistry</subject><subject>Anisoles - toxicity</subject><subject>Bacteria</subject><subject>Bioavailability</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Chromatography, Ion Exchange</subject><subject>Ecological risk assessment</subject><subject>Explosive Agents - chemistry</subject><subject>Explosive Agents - toxicity</subject><subject>Explosive forming</subject><subject>Hydrolysis</subject><subject>Hydrophobic and Hydrophilic Interactions</subject><subject>Hydrophobicity</subject><subject>Insensitive munition</subject><subject>Molecular Structure</subject><subject>Phenylenediamines - chemistry</subject><subject>Reduction</subject><subject>Regioselectivity</subject><subject>Risk</subject><subject>Soil (material)</subject><subject>Soil Pollutants - chemistry</subject><subject>Soil Pollutants - toxicity</subject><subject>Solubility</subject><subject>Spectrophotometry</subject><subject>TNT</subject><issn>0045-6535</issn><issn>1879-1298</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqNkE1PGzEQhq2qqEmBv1Btb1Ril_HX7vqIUmiQEFzas-XYY8XR7jq1N0j8-zoKrXrkNHN43nk1DyFfKTQUaHuza-wWx5j3W0zYMKCiAdmA6D6QJe07VVOm-o9kCSBk3UouF-RzzjuAEpbqE1kwKVroBF-S9d30ElKcRpxmM1TezFhFX7FrUbswhTlFM4UcB6yuvj_dPn2rzOSqMOcqoTtYdNU-xbLM-YKceTNkvHyb5-TX_d3P1bp-fP7xsLp9rK0QfK4lWCUsgHeyEx54v3GMGday3nhjNoojNb73nCmmWiuNA1GecZ3jjG285_ycXJ3uluLfB8yzHkO2OAxmwnjImrZdp2h5kL4H5bxTfasKqk6oTTHnhF7vUxhNetUU9NG53un_nOujcw1SF-cl--Wt5rAZ0f1L_pVcgNUJwOLlJWDS2Qacir2Q0M7axfCOmj9fXpc4</recordid><startdate>201501</startdate><enddate>201501</enddate><creator>Hawari, J.</creator><creator>Monteil-Rivera, F.</creator><creator>Perreault, N.N.</creator><creator>Halasz, A.</creator><creator>Paquet, L.</creator><creator>Radovic-Hrapovic, Z.</creator><creator>Deschamps, S.</creator><creator>Thiboutot, S.</creator><creator>Ampleman, G.</creator><general>Elsevier Ltd</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7ST</scope><scope>C1K</scope><scope>SOI</scope><scope>8FD</scope><scope>FR3</scope><scope>KR7</scope></search><sort><creationdate>201501</creationdate><title>Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products</title><author>Hawari, J. ; Monteil-Rivera, F. ; Perreault, N.N. ; Halasz, A. ; Paquet, L. ; Radovic-Hrapovic, Z. ; Deschamps, S. ; Thiboutot, S. ; Ampleman, G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c443t-50c94c00fd574f038bd22a2628afaab93e1af8f329296c5ad04129d7d322bff33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>2,4-Diaminoanisole</topic><topic>2,4-Dinitroanisole</topic><topic>2,4-Dinitrophenol - chemistry</topic><topic>Anisoles - chemistry</topic><topic>Anisoles - toxicity</topic><topic>Bacteria</topic><topic>Bioavailability</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Chromatography, Ion Exchange</topic><topic>Ecological risk assessment</topic><topic>Explosive Agents - chemistry</topic><topic>Explosive Agents - toxicity</topic><topic>Explosive forming</topic><topic>Hydrolysis</topic><topic>Hydrophobic and Hydrophilic Interactions</topic><topic>Hydrophobicity</topic><topic>Insensitive munition</topic><topic>Molecular Structure</topic><topic>Phenylenediamines - chemistry</topic><topic>Reduction</topic><topic>Regioselectivity</topic><topic>Risk</topic><topic>Soil (material)</topic><topic>Soil Pollutants - chemistry</topic><topic>Soil Pollutants - toxicity</topic><topic>Solubility</topic><topic>Spectrophotometry</topic><topic>TNT</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hawari, J.</creatorcontrib><creatorcontrib>Monteil-Rivera, F.</creatorcontrib><creatorcontrib>Perreault, N.N.</creatorcontrib><creatorcontrib>Halasz, A.</creatorcontrib><creatorcontrib>Paquet, L.</creatorcontrib><creatorcontrib>Radovic-Hrapovic, Z.</creatorcontrib><creatorcontrib>Deschamps, S.</creatorcontrib><creatorcontrib>Thiboutot, S.</creatorcontrib><creatorcontrib>Ampleman, G.</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Environment Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Environment Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Civil Engineering Abstracts</collection><jtitle>Chemosphere (Oxford)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hawari, J.</au><au>Monteil-Rivera, F.</au><au>Perreault, N.N.</au><au>Halasz, A.</au><au>Paquet, L.</au><au>Radovic-Hrapovic, Z.</au><au>Deschamps, S.</au><au>Thiboutot, S.</au><au>Ampleman, G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products</atitle><jtitle>Chemosphere (Oxford)</jtitle><addtitle>Chemosphere</addtitle><date>2015-01</date><risdate>2015</risdate><volume>119</volume><spage>16</spage><epage>23</epage><pages>16-23</pages><issn>0045-6535</issn><eissn>1879-1298</eissn><abstract><![CDATA[•DNAN undergoes regioselective reduction at the o-NO2 under abiotic and biotic conditions.•Physicochemical parameters (Sw, pKa, logKow, Kd) are provided for DNAN and its amine products.•Physicochemical behavior depends on type and position of substituent(s) on the aromatic ring.•Amine products of DNAN irreversibly bind to soil under oxic conditions.
Several defense departments intend to replace 2,4,6-trinitrotoluene (TNT) in munitions formulations by the less sensitive 2,4-dinitroanisole (DNAN). To help understand environmental behavior and ecological risk associated with DNAN we investigated its key initial abiotic and biotic reaction routes and determined relevant physicochemical parameters (pKa, logKow, aqueous solubility (Sw), partition coefficient (Kd)) for the chemical and its products. Reduction of DNAN with either zero valent iron or bacteria regioselectively produced 2-amino-4-nitroanisole (2-ANAN) which, under strict anaerobic conditions, gave 2,4-diaminoanisole (DAAN). Hydrolysis under environmental conditions was insignificant whereas photolysis gave photodegradable intermediates 2-hydroxy-4-nitroanisole and 2,4-dinitrophenol. Physicochemical properties of DNAN and its amino products drastically depended on the type and position of substituent(s) on the aromatic ring. Sw followed the order (TNT<DNAN<2-ANAN<4-ANAN<DAAN) whereas logKow followed the order (DAAN<4-ANAN<2-ANAN<DNAN<TNT). In soil, successive replacement of NO2 by NH2 in DNAN enhanced irreversible sorption and reduced bioavailability under oxic conditions. Although DNAN is more soluble than TNT, its lower hydrophobicity and its tendency to form aminoderivatives that sorb irreversibly to soil contribute to make it less toxic than the traditional explosive TNT.]]></abstract><cop>England</cop><pub>Elsevier Ltd</pub><pmid>25460743</pmid><doi>10.1016/j.chemosphere.2014.05.047</doi><tpages>8</tpages></addata></record> |
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| subjects | 2,4-Diaminoanisole 2,4-Dinitroanisole 2,4-Dinitrophenol - chemistry Anisoles - chemistry Anisoles - toxicity Bacteria Bioavailability Chromatography, High Pressure Liquid Chromatography, Ion Exchange Ecological risk assessment Explosive Agents - chemistry Explosive Agents - toxicity Explosive forming Hydrolysis Hydrophobic and Hydrophilic Interactions Hydrophobicity Insensitive munition Molecular Structure Phenylenediamines - chemistry Reduction Regioselectivity Risk Soil (material) Soil Pollutants - chemistry Soil Pollutants - toxicity Solubility Spectrophotometry TNT |
| title | Environmental fate of 2,4-dinitroanisole (DNAN) and its reduced products |
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