2,2'-((2-((Carboxymethyl)(2-((carboxymethyl)amino)ethyl)amino)ethyl)azanediyl)diacetic acid
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2,2'-((2-((Carboxymethyl)(2-((carboxymethyl)amino)ethyl)amino)ethyl)azanediyl)diacetic acid

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Category
Other Unnatural Amino Acids
Catalog number
BAT-015995
CAS number
128139-51-5
Molecular Formula
C12H21N3O8
Molecular Weight
335.31
IUPAC Name
2-[2-[2-[bis(carboxymethyl)amino]ethyl-(carboxymethyl)amino]ethylamino]acetic acid
Synonyms
({2-[Bis(carboxymethyl)amino]ethyl}{2-[(carboxymethyl)amino]ethyl}amino)acetic acid; Glycine, N-[2-[bis(carboxymethyl)amino]ethyl]-N-[2-[(carboxymethyl)amino]ethyl]-
Purity
≥95%
Density
1.467±0.06 g/cm3 (Predicted)
Boiling Point
644.8±55.0°C (Predicted)
InChI
InChI=1S/C12H21N3O8/c16-9(17)5-13-1-2-14(6-10(18)19)3-4-15(7-11(20)21)8-12(22)23/h13H,1-8H2,(H,16,17)(H,18,19)(H,20,21)(H,22,23)
InChI Key
SLIOGOFAZDOJQA-UHFFFAOYSA-N
Canonical SMILES
C(CN(CCN(CC(=O)O)CC(=O)O)CC(=O)O)NCC(=O)O
1. Effect of N-hydroxyethyl-ethylenediamine-triacetic acid (HEDTA) on Cr(VI) reduction by Fe(II)
Y M Tzou, M K Wang, R H Loeppert Chemosphere. 2003 Jun;51(9):993-1000. doi: 10.1016/S0045-6535(03)00002-X.
The complexation of Fe(II) with organic ligand results in the decrease of redox potential, and enhances the reduction ability of Fe(II). An important example is the use of Fe(II)-organic complexes to accelerate Cr(VI) reduction. Dissolved O(2) and light can potentially affect Cr(VI) reduction; however, these two factors have not been adequately evaluated. A batch technique was used to investigate the Cr(VI) reduction as influenced by the light and dissolved O(2) using N-hydroxyethyl-ethylenediamine-triacetic acid (HEDTA) and Fe(II) solutions. The oxidation of Fe(II) by dissolved O(2) was rapid in the presence of HEDTA at low pH; nonetheless, the oxidation proceeded slowly when HEDTA was absent. Although Cr(VI) could be reduced by free Fe(II) at low pH, the reaction was considerably slower than that of systems involving HEDTA. The enhancement of Cr(VI) reduction by Fe(II) in the presence of high concentrations of HEDTA was achieved as a result of two processes. First, HEDTA acted as a ligand for expediting electron transfer between Fe(II) and Cr(VI). Secondly, HEDTA served as a reductant for Cr(VI) under illumination.
2. Comparison of natural humic substances and synthetic ethylenediaminetetraacetic acid and nitrilotriacetic acid as washing agents of a heavy metal-polluted soil
Mohsen Soleimani, Mohammad A Hajabbasi, Majid Afyuni, Samira Akbar, Julie K Jensen, Peter E Holm, Ole K Borggaard J Environ Qual. 2010 Apr 13;39(3):855-62. doi: 10.2134/jeq2009.0292. Print 2010 May-Jun.
Ethylenediaminetetraacetic acid (EDTA), nitrilotriacetic acid (NTA), and other synthetic polycarboxylic acids have been shown to possess substantial capacity as washing agents of heavy metal-polluted soils, but they are environmentally problematic. Therefore, a sample of natural soluble humic substances (HS) was tested as a possible substitute. The efficiency of HS to extract cadmium (Cd), copper (Cu), and lead (Pb) from a strongly polluted calcareous urban soil was compared with that of EDTA and NTA. The influence of extractant concentration (25-100 mmol L(-1) C), solution/soil ratio (5-100 L kg(-1)), and single-step vs. multistep extraction on heavy metal removal from the soil was investigated. The extracted pools were assessed by sequential extraction. Ethylenediaminetetraacetic acid and NTA extracted up to 86, 77, and 30% of total soil Cd, Cu, and Pb, respectively, whereas HS extracted 44, 53, and 4%. Extracted amounts of Cd, Cu, and Pb increased with increasing extractant concentration and solution/soil ratio in the range 5 to 100 L kg(-1). Single-step extraction removed about the same amounts of the three metals as multiple-step extraction. The metal-extracted pools of the soil depended on the metal and on the extractant. The overall conclusion is that soluble HS can replace synthetic EDTA and NTA as washing agents for Cd- and Cu-polluted soils, whereas HS is not a promising substitute of EDTA or NTA for cleaning Pb-polluted, calcareous soils.
3. Chelant extraction of heavy metals from contaminated soils using new selective EDTA derivatives
Tao Zhang, Jun-Min Liu, Xiong-Fei Huang, Bing Xia, Cheng-Yong Su, Guo-Fan Luo, Yao-Wei Xu, Ying-Xin Wu, Zong-Wan Mao, Rong-Liang Qiu J Hazard Mater. 2013 Nov 15;262:464-71. doi: 10.1016/j.jhazmat.2013.08.069. Epub 2013 Sep 1.
Soil washing is one of the few permanent treatment alternatives for removing metal contaminants. Ethylenediaminetetraacetic acid (EDTA) and its salts can substantially increase heavy metal removal from contaminated soils and have been extensively studied for soil washing. However, EDTA has a poor utilization ratio due to its low selectivity resulting from the competition between soil major cations and trace metal ions for chelation. The present study evaluated the potential for soil washing using EDTA and three of its derivatives: CDTA (trans-1,2-cyclohexanediaminetetraacetic acid), BDTA (benzyldiaminetetraacetic acid), and PDTA (phenyldiaminetetraacetic acid), which contain a cylcohexane ring, a benzyl group, and a phenyl group, respectively. Titration results showed that PDTA had the highest stability constants for Cu(2+) and Ni(2+) and the highest overall selectivity for trace metals over major cations. Equilibrium batch experiments were conducted to evaluate the efficacy of the EDTA derivatives at extracting Cu(2+), Zn(2+), Ni(2+), Pb(2+), Ca(2+), and Fe(3+) from a contaminated soil. At pH 7.0, PDTA extracted 1.5 times more Cu(2+) than did EDTA, but only 75% as much Ca(2+). Although CDTA was a strong chelator of heavy metal ions, its overall selectivity was lower and comparable to that of EDTA. BDTA was the least effective extractant because its stability constants with heavy metals were low. PDTA is potentially a practical washing agent for soils contaminated with trace metals.
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