Reactions of chlorine with selected aromatic models of aquatic humic material

Norwood, Daniel L.; Johnson, J. Donald; Christman, Russell F.; Hass, J. Ronald; Bobenrieth, Marie J.

doi:10.1021/es60162a012

Cited by 173 publications

(99 citation statements)

References 8 publications

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“…Furthermore, the absorption bands at 1580-1630 cm −1 could be attributed to aromatic ring C C-C and to the asymmetric C O stretching of quinones, conjugated ketones, while the peak at 1387 cm −1 may be C-H stretching deformation of -CH 3 and -CH 2 groups [33], and their intensities decreased with increasing reaction times. These results suggested that the "activated" aromatic content and oxygen-rich ketones have been destroyed during the degradation process, which are generally thought to be the key factors that could enhance the reactivity of humic substances with chlorine to form DBPs [3,34]. By comparison with HA before reaction, strong O-H stretching absorption bands from 3000 to 3500 cm −1 are characteristic of the hydrophilic fractions [32].…”

Section: Degradation Characteristics and Dbp Formation Of Hamentioning

confidence: 96%

Degradation characteristics of humic acid over iron oxides/Fe0 core–shell nanoparticles with UVA/H2O2

Nie

Zhou

et al. 2010

Journal of Hazardous Materials

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a b s t r a c tIron oxides coated on Fe 0 core-shell nanospheres (nIOCI) were synthesized through the reduction of ferrous sulfate aqueous solution by sodium borohydride at ambient atmosphere. The catalyst was highly effective for the degradation of humic acid (HA) in the presence of H 2 O 2 and UVA at neutral pH. Under deoxygenated conditions in the dark, the generation of hydroxyl radicals in aqueous nIOCI dispersion verified its galvanic cell-like performance, which enhanced the interfacial electron transfer and led to its higher reactivity. By the total organic carbon, the absorbance of UV 254 , FTIR, the molecular weight distribution and the chemical fractional character analysis, the degradation process of HA was shown to proceed by the disappearance of aromaticity, the increase of hydrophilic fraction and aromatic ring openings into CO 2 and small organic acid. The treated HA showed much lower reactivity toward chlorine and the disinfection byproduct (DBP) formation potential was also greatly reduced. Moreover, it was found that the DBP formation potential more depended on the structure of the intermediates of HA degradation than TOC removal.Crown

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Section: Degradation Characteristics and Dbp Formation Of Hamentioning

confidence: 96%

Degradation characteristics of humic acid over iron oxides/Fe0 core–shell nanoparticles with UVA/H2O2

Nie

Zhou

et al. 2010

Journal of Hazardous Materials

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“…284 2,2,4-trichloro-1,3-cyclopentenedione (P198) and its isomer were detected (95% similarity with NIST 285 database) from the MTBE extract after derivatization using acidic methanol (RT= 9.7min) (Figure 286 S9). The formation of 2,2,4-trichloro-1,3-cyclopentenedione has been reported as a chlorination by-287 product of resorcinol (Boyce et al, 1983;Norwood et al, 1980). 288…”

Section: Hydroxy-2-pyridone With Four Chlorine Atoms (Text S3) 271mentioning

confidence: 99%

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Nihemaiti

Roux

Hoppe‐Jones

et al. 2016

Environ. Sci. Technol.

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18The potential formation of nitrogenous disinfection by-products (N-DBPs) was investigated from the 19 chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the 20 formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production 21 yields. Resorcinol, a major precursor of chloroform, also formed di-/tri-chloroacetonitrile, di-/tri-22 chloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and 23carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on 24 resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based 25 on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and 26 fragmentation patterns from electronic impact and positive chemical ionization modes, several 27 products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-28 1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were 29 structurally similar to the heterocyclic compounds formed during chlorination, such as the highly 30 mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To 31 our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic 32 compounds is reported from chloramination process. The formation of these nitrogenous by-products 33 during chloramination might be of concern considering their potential toxicity. 34 ABSTRACT ART35 36 37 INTRODUCTION 38

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“…A dark violet solid was obtained and kept in a desiccator for analysis. 4 (57.6)%; H = 9.2 (8.7)%; N = 3.2 (3.6)%; Fe = 7.4 (7.3)%. All experiments to crystallize the complex failed and instead produced an amorphous solid probably due to the long aliphatic chain present in CTA cation that prevent a regular crystal arrangement.…”

Section: Preparation Of the Solid Compound From The Solutionmentioning

confidence: 99%

“…Wang et al 3 demonstrated that several phenolic acids in concentrations from 25 to 100 mg L -1 , in culture solution, inhibit the growth of several plant cultures. The phenolic substances are important species to maintain the reduction capacity strength in the aquatic medium 4 and can be generated by microbial processes, lignin degradation or produced by fungi in wood 5 . The S 2 O 3 2-is found in fertilizers as a source of sulfur and its chemical reactions in soil are not still completely understood 6 .…”

Section: Introductionmentioning

confidence: 99%

Iron oxide and pyrocatechol: a spectroscopy study of the reaction products

Barreto¹,

Barreto²,

Moreira³

et al. 2006

Quím. Nova

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Recebido em 3/1/06; aceito em 24/3/06; publicado na web em 1/8/06The reaction of 1,2-dihydroxy-benzene (pyrocatechol) (C 6 H 6 O 2 ) with iron oxide (Fe 2 O 3 ) and sodium thiosulfate (Na 2 S 2 O 3 ) in aqueous medium (pH 7) was investigated. Pyrocatechol suffers autoxidation and coordinates with Fe 3+ in solution. The presence of S 2 O 3 2-in solution was fundamental to generate and stabilize the pyrocatechol oxidation products as o-semiquinones. This compound was isolated and its structure characterized using FT-IR, EPR and UV-Vis Spectroscopy as [CTA][Fe(SQ) 2 (Cat)]. A thermal mass loss mechanism was proposed based on Thermogravimetric Analysis (TG) to support the structural characterization.

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Reactions of chlorine with selected aromatic models of aquatic humic material

Cited by 173 publications

References 8 publications

Degradation characteristics of humic acid over iron oxides/Fe0 core–shell nanoparticles with UVA/H2O2

Degradation characteristics of humic acid over iron oxides/Fe0 core–shell nanoparticles with UVA/H2O2

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Iron oxide and pyrocatechol: a spectroscopy study of the reaction products

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