The use of amino compounds for binding 2,4,6-trinitrotoluene in water

被引:47
作者
Fant, F
De Sloovere, A
Matthijsen, K
Marlé, C
El Fantroussi, S
Verstraete, W
机构
[1] Univ Ghent, Lab Microbial Ecol & Technol, B-9000 Ghent, Belgium
[2] Univ Ghent, Dept Organ Chem, B-9000 Ghent, Belgium
关键词
TNT; amino acid; Meisenheimer complex;
D O I
10.1016/S0269-7491(00)00077-4
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Sites polluted with 2,4,6-trinitrotoluene (TNT) constitute a worldwide problem. In this work, chemical reactions for binding TNT to amino-compounds are proposed as an initial step for developing new remediation techniques to clean-up groundwater and soils contaminated with TNT. Indeed, addition of aniline and an amino acid-like cysteine caused a decrease in free TNT of 86% and 68-100%, respectively. Using (13)C-NMR spectroscopy, it was shown that TNT chemically forms a Meisenheimer complex with cysteine and aniline in 1/1 (by vol.) H(2)O/d(6)-acetone. (C) 2000 Elsevier Science Ltd. Al rights reserved.
引用
收藏
页码:503 / 507
页数:5
相关论文
共 18 条
[1]   RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION [J].
BUNCEL, E ;
DUST, JM ;
TERRIER, F .
CHEMICAL REVIEWS, 1995, 95 (07) :2261-2280
[2]   INTERACTION OF ELECTRON ACCEPTORS WITH BASES .19. INTERACTION OF 1,3,5-TRINITROBENZENE WITH SECONDARY AMINES IN ACETONE SOLUTION [J].
FOSTER, R ;
FYFE, CA .
TETRAHEDRON, 1966, 22 (06) :1831-&
[3]   Identification of products resulting from the biological reduction of 2,4,6-trinitrotoluene, 2,4-dinitrotoluene, and 2,6-dinitrotoluene by Pseudomonas sp [J].
Haidour, A ;
Ramos, JL .
ENVIRONMENTAL SCIENCE & TECHNOLOGY, 1996, 30 (07) :2365-2370
[4]   WET AIR OXIDATION OF TRINITROTOLUENE MANUFACTURING RED WATER [J].
HAO, OJ ;
PHULL, KK ;
DAVIS, AP ;
CHEN, JM ;
MALONEY, SW .
WATER ENVIRONMENT RESEARCH, 1993, 65 (03) :213-220
[5]  
Hartter D.R., 1985, TOXICITY NITROAROMAT, P1
[6]   Enhanced humification as an in-situ bioremediation technique for 2,4,6-trinitrotoluene (TNT) contaminated soils [J].
Held, T ;
Draude, G ;
Schmidt, FRJ ;
Brokamp, A ;
Reis, KH .
ENVIRONMENTAL TECHNOLOGY, 1997, 18 (05) :479-487
[7]   Long-term TNT sorption and bound residue formation in soil [J].
Hundal, LS ;
Shea, PJ ;
Comfort, SD ;
Powers, WL ;
Singh, J .
JOURNAL OF ENVIRONMENTAL QUALITY, 1997, 26 (03) :896-904
[8]  
JENKINS TF, 1990, US ARMY COLD REGIONS, P90
[9]   CARBANIONS .2. C-13 NUCLEAR MAGNETIC-RESONANCE STUDY OF MEISENHEIMER COMPLEXES AND THEIR CHARGE-DISTRIBUTION PATTERN [J].
OLAH, GA ;
MAYR, H .
JOURNAL OF ORGANIC CHEMISTRY, 1976, 41 (21) :3448-3451
[10]   Effect of redox potential and pH on TNT transformation in soil-water slurries [J].
Price, CB ;
Brannon, JM ;
Hayes, CA .
JOURNAL OF ENVIRONMENTAL ENGINEERING, 1997, 123 (10) :988-992