Journal of South China University of Technology(Natural Science) >

2022 , Vol. 50 >Issue 8: 102 - 108

DOI: https://doi.org/10.12141/j.issn.1000-565X.210345

Environmental Science & Technology

Effect Factors and Generation Pathway of Iodoacetic Acid from Tryptophan During UV Irradiation Combined with Chlorine Disinfection

Expand
  • College of Civil Engineering and Architecture，Zhejiang University，Hangzhou 310058，Zhejiang，China
杨玉龙（1973-），男，博士，副教授，主要从事市政工程安全研究。E-mail：yulongy@zju. edu. cn

Received date: 2021-05-26

  Online published: 2021-08-31

Supported by

the National Science and Technology Major Project(2017ZX07201004);the National Natural Science Foundation of China(51978602)

Fold

Abstract

Amino acid is a common nitrogenous compound in water. Iodine disinfection by-products could be produced in the process of tryptophan chlorination disinfection in present of I-. To investigate the generation and mechanism of iodoacetic acid from amino acid during the use of UV and chlorine for disinfection, this paper selected a typical iodoacetic acid, namely, tryptophan, and developed a generation kinetic model. In the investigation, first, the influences of different factors including UV irradiation time, chlorine dosage, pH value, Br- content, and I- content on the generation of iodoacetic acid were explored, and the generation pathway of iodoacetic acid was further analyzed. The results show that the generation process of iodoacetic acid fits the pseudo first-order reaction kinetic model, with a generation rate constant k of 0.17 h-1. UV irradiation time, chlorine dosage, pH value, Br- content, and I- content all exert big influence on the generation process of iodoacetic acid. UV irradiation time promotes the generation of iodoacetic acid, and the yield of iodoacetic acid increases with the increase of UV irradiation time. When the pH value is in the range of 6 ~ 8, the yield of iodoacetic acid increases with the pH value. The generation of iodoacetic acid exhibits a firstly increase and then decrease trend with the increase in chlorine. When the ration of the concentrations of tryptophan and chlorine dosage is 1∶2, the production of IAA reaches the highest (15.30 μg/L). The paper also established an equation describing the relationship among Br- content, I- content and iodoacetic acid yield. It is found that Br- has a negative correlation to the generation of iodoacetic acid, while I- content has a greater positive one. In addition, four products including butanoic acid anhydride and isovaleric anhydride were detected using LC-MS-MS and GC-MS. It is speculated that the generation path of iodoacetic acid is that C12H17NO3 is firstly produced from tryptophan through the action of UV photohydrolysis and hydroxyl radicals, and then isovaleric acid and butyrate acid are generated sequentially under the oxidation of HOCl and HOI, and finally iodoacetic acid is generated.

Key words： tryptophan; UV-light; disinfection by-products; iodoacetic acid; generation pathway

Cite this article

YANG Yulong, FEI Weicheng, JI Jingxuan, et al . Effect Factors and Generation Pathway of Iodoacetic Acid from Tryptophan During UV Irradiation Combined with Chlorine Disinfection[J]. Journal of South China University of Technology(Natural Science), 2022 , 50(8) : 102 -108 . DOI: 10.12141/j.issn.1000-565X.210345

References

1 TREHY M L， YOST R A， MILES C J ．Chlorination by-products of amino-acids in natural-waters［J］．Environmental Science & Technology，1986，20（11）：1117-1122．
2 DU P， ZHAO H， CAO H，et al ．Transformation of halobenzoquinones with the presence of amino acids in water：products，pathways and toxicity［J］．Water Research，2017，122：299-307．
3 WANG X， WANG J， ZHANG Y H，et al ．Characterization of unknown iodinated disinfection byproducts during chlorination/chloramination using ultrahigh resolution mass spectrometry［J］．Science of the Total Environment，2016，554/555：83-88．
4 WANG L S， HU H Y， WANG C ．Effect of ammonia nitrogen and dissolved organic matter fractions on the genotoxicity of wastewater effluent during chlorine disinfection［J］．Environmental Science & Technology，2007，41（1）：160-165．
5 TIAN F X， XU B， LIN Y L，et al ．Photodegradation kinetics of iopamidol by UV irradiation and enhanced formation of iodinated disinfection by-products in sequential oxidation processes［J］．Water Research，2014，58：198-208．
6 LIU J Q， ZHANG X R ．Comparative toxicity of new halophenolic DBPs in chlorinated saline wastewater effluents against a marine alga：halophenolic DBPs are generally more toxic than haloaliphatic ones［J］．Water Research，2014，65：64-72．
7 CHU W H， GAO N Y， YIN D Q，et al ．Trace determination of 13 haloacetamides in drinking water using liquid chromatography triple quadrupole mass spectrometry with atmospheric pressure chemical ionization［J］．Journal of Chromatography A，2012，1235：178-181．
8 RICHARDSON S D， FASANO F， ELLINGTON J J，et al ．Occurrence and mammalian cell toxicity of iodinated disinfection byproducts in drinking water［J］．Environmental Science & Technology，2008，42（22）：8330-8338．
9 LIU L Z， XING X C， HU C，et al ．Effect of sequential UV/free chlorine disinfection on opportunistic pathogens and microbial community structure in simulated drinking water distribution systems［J］．Chemosphere，2019，219：971-980．
10 ZHOU X H， ZHU L J， WANG L，et al ．Protective effect of Edaravone in primary cerebellar granule neurons against iodoacetic acid-induced cell injury［J］．Oxidative Medicine & Cellular Longevity，2015，2015：606987/1-8．
11 PROCHAZKA E， ESCHER B I， PLEWA M J，et al ．In vitro cytotoxicity and adaptive stress responses to selected haloacetic acid and halobenzoquinone water disinfection byproducts［J］．Chemical Research in Toxicology，2015，28（10）：2059-2068．
12 ESCOBAR L F， HOYOS L S， LONDONO E，et al ．Genotoxic and clastogenic effects of monohaloacetic acid drinking water disinfection by-products in primary human lymphocytes［J］．Water Research，2013，47（10）：3282-3290．
13 RICHARDSON S D， PLEWA M J， WAGNER E D，et al ．Occurrence，genotoxicity，and carcinogenicity of regulated and emerging disinfection by-products in drinking water：a review and roadmap for research［J］.Mutation Research-Reviews in Mutation Research，2007，636（1/2/3）：178-242．
14 PLEWA M J， WAGNER E D， RICHSRDSON S D，et al ．Chemical and biological characterization of newly discovered iodoacid drinking water disinfection byproducts［J］．Environmental Science & Technology，2004，38（18）：4713-4722．
15 SAYESS R， KHALIL A， SHAH M，et al ．Comparative cytotoxicity of six iodinated disinfection byproducts on nontransformed epithelial human colon cells［J］．Environmental Science & Technology Letters，2017，4（4）：143-148．
16 WEI X， XIN C， WANG X，et al ．Occurrence of regulated and emerging iodinated DBPs in the Shanghai drinking water［J］．PLoS One，2013，8（3）：e59677/1-7．
17 LIU S G， LI Z L， DONG H Y，et al ．Formation of iodo-trihalomethanes，iodo-acetic acids，and iodo-acetamides during chloramination of iodide-containing waters：factors influencing formation and reaction pathways［J］．Journal of Hazardous Materials，2017，321：28-36．
18 COTTON C A， OWEN D M， CLINE G C，et al ．UV disinfection costs for inactivating cryptosporidium［J］．Journal American Water Works Association，2001，93（6）：82-94．
19 RAND J L， HOFMANN R， ALAM M Z B，et al ．A field study evaluation for mitigating biofouling with chlorine dioxide or chlorine integrated with UV disinfection［J］．Water Research，2007，41（9）：1939-1948．
20 赵敬国 ．紫外线/高铁酸钾与氯联合消毒工艺特性研究［D］．杭州：浙江大学，2016．
21 HU J， SONG H， KARANFIL T ．Comparative analysis of halonitromethane and trihalomethane formation and speciation in drinking water：the effects of disinfectants，pH，bromide，and nitrite［J］．Environmental Science & Technology，2010，44（2）：794-799．
22 陈新波 ．水体中氨基酸氯化生成常规及碘代三卤甲烷的研究［D］．杭州：浙江大学 2017．
23 YE T， XU B， LIN Y L，et al ．Formation of iodinated disinfection by-products during oxidation of iodide-containing waters with chlorine dioxide［J］．Water Research，2013，47（9）：3006-3014．
24 LI C， LIN Q， DONG F，et al ．Formation of iodinated trihalomethanes during chlorination of amino acid in waters［J］．Chemosphere，2019，217：355-363．
25 HUA G H， RECKHOW D A， KIM J ．Effect of bromide and iodide ions on the formation and speciation of disinfection byproducts during chlorination［J］．Environmental Science & Technology，2006，40（9）：3050-3056．
26 ZHANG T Y， XU B， HU C Y，et al ．A comparison of iodinated trihalomethane formation from chlorine，chlorine dioxide and potassium permanganate oxidation processes［J］．Water Research，2015，68：394-403，479．
27 LIU Z， LIN Y L， XU B，et al ．Formation of iodinated trihalomethanes during breakpoint chlorination of iodide-containing water［J］．Journal of Hazardous Materials，2018，353：505-513．
28 GAO Z C， LIN Y L， XU B，et al ．Effect of bromide and iodide on halogenated by-product formation from different organic precursors during UV/chlorine processes［J］．Water Research，2020，182：116035．
29 BOND T， HUANG J， GRAHAM N J D，et al ．Examining the interrelationship between DOC，bromide and chlorine dose on DBP formation in drinking water - a case study［J］．Science of the Total Environment，2014，470：469-479．
30 ZHANG K， PARKER K M ．Halogen radical oxidants in natural and engineered aquatic systems［J］．Environmental Science & Technology，2018，52（17）：9579-9594．
31 ZHU X H， ZHANG X R ．Modeling the formation of TOCl，TOBr and TOI during chlor（am）ination of drinking water［J］．Water Research，2016，96：166-176．
32 TREHY M L， YOST R A， MILES C J ．Chlorination byproducts of amino acids in natural waters［J］．Environmental Science & Technology，1986，20（11）：1117-1122．
Options
Outlines

/

〈 〉