Journal of Textile Research ›› 2019, Vol. 40 ›› Issue (11): 131-139.doi: 10.13475/j.fzxb.20181000409

• Dyeing and Finishing & Chemicals • Previous Articles     Next Articles

Degradation kinetics and mechanism of Acid Red 37 under attack of sulfate radicals

ZHUANG Shuai1, YANG Hai1(), AN Jibin2, HU Qian1, ZHANG Hao1, HE Guitian1, YI Bing1   

  1. 1. Hunan Provincial Key Laboratory of Environmental Catalysis & Waste Recycling, Hunan Institute of Engineering, Xiangtan, Hunan 411104, China
    2. Chongqing Key Laboratory of Environmental Materials & Remediation Technologies, Chongqing University of Arts and Sciences, Chongqing 402160, China
  • Received:2018-10-08 Revised:2019-08-11 Online:2019-11-15 Published:2019-11-26
  • Contact: YANG Hai E-mail:yanghai1001@163.com

Abstract:

In order to explore the degradation possibility of Acid Red 37 (AR37) under the attack of sulfate radicals, the system of UVC-activated potassium persulfate (PDS) was obtained in mixed solution of acetonitrile (ACN) and water. Firstly, the degradation feasibility of AR37 in different solutions, such as dimethyl sulfoxide (DMSO), N-N-dimethylformamide (DMF), ACN and water, was compared. And then the influences of the dosage of PDS, the concentration of substrate, the reaction temperature and the UVC light intensity on the degradation kinetics of AR37 were studied in the system of UVC/PDS/(90%ACN+10%H2O). Lastly, the degradation intermediates of AR37 were identified by HPLC/MS/MS and the transformation mechanism was proposed. The results indicated that AR37 can be degraded in the system of UVC/PDS/(90%ACN+10%H2O). The removal efficiency of AR37 is more than 98% and the pseudo-first-order rate is 0.123 min-1. Higher temperature and light intensity facilitate producing the sulfate free radical, which is helpful for the degradation of AR37; and the sulfate free radical plays an important role in the degradation of AR37 in the system of UVC/PDS/(90%ACN+10%H2O). Based on the degradation intermediates, the degradation pathway is deduced, such as the cleavage of azo bond and the desulfonation due to single electron transfer of the sulfate free radical, as well as hydroxylation products from hydrogen-abstracted and substitution reaction.

Key words: Acid Red 37, azo dye, dye wastewater, degradation kinetics, photo-activated

CLC Number: 

  • X131

Fig.1

Chemical structure of AR37"

Fig.2

Degradation effect of AR37 in different solvents"

Fig.3

Degradation curves of AR37 in four kinds systems of ACN solvents(a) and relatonship between-ln(C/C0) and time(b)"

Fig.4

Degradation curves of AR37 under different PDS dosage(a)and effect of PDS dosages on degradation kinetics of AR37(b)"

Fig.5

Degradation curves of AR37 under different substrate concentration(a) and effect of substrate concentration on degradation kinetics of AR37(b)"

Fig.6

Degradation curves of AR37 under different reaction temperature (a) and effect of different reaction temperature on degradation kinetics of AR37 (b)"

Fig.7

Degradation curves of AR37 under different light intensity (a) and Effects of different light intensity on the degradation kinetics of AR37(b)"

Fig.8

Homolysis of S2O82-"

Fig.9

Degradation curves of AR37 after addition of EtOH(a),TBA(b)and comparison on degradation rate(c)"

Fig.10

EPR spectra of UVC/PDS in different solvents system after 10 min reaction"

Fig.11

TIC chromatography of AR37 after 15 min reaction in UVC/PDS/(90%ACN+10%H2O) system"

Tab.1

Proposed structure of AR37"

降解产物
编号
保留时间/min 质荷比(m/z) 分子式 可能降解产物 反应体系
实验值 理论值
P1 5.95 495.025 6 495.023 1 C18H14N4O9S2 单羟基化产物 体系1和3
P2 6.57 416.087 3 416.071 8 C18H15N4O6S 脱单磺酸基后单羟基取代产物 体系1和3
P3 6.71 400.095 4 400.076 9 C18H15N4O5S 脱单磺酸基产物 体系1和3
P4 7.19 255.043 2 255.012 9 C10H8NO5S 4,5-二羟基-6-氨基萘-2-磺酸 体系1,2和3
P5 7.52 192.077 1 192.058 2 C10H9NO3 7-氨基-1,3,8-萘三醇 体系1和3
P6 7.86 353.132 4 353.117 2 C18H16N4O4 脱双磺酸基后二羟基取代产物 体系1,2和3
P7 7.96 206.041 1 206.037 5 C10H7NO4 2-硝基-1,8-萘二醇 体系1,2和3
P8 8.25 337.134 3 337.122 2 C18H16N4O3 脱单磺酸基后单羟基取代产物 体系1,2和3
P9 8.70 181.066 1 181.053 5 C8H8N2O3 对硝基乙酰苯胺 体系1和3
P10 9.15 151.089 7 151.079 3 C8H10N2O 对氨基乙酰苯胺 体系1,2和3

Fig.12

Proposed degradation mechanism of AR37 in system of UVC/PDS/(90%ACN+10%H2O)"

[1] GOMARASCHI M, OSSOLI A, POZZI S, et al. Enhanced decolorization of Orange G in a Fe(II)-EDDS activated persulfate process by accelerating the regeneration of ferrous iron with hydroxylamine[J]. Chemical Engineering Journal, 2014,256(6):316-323.
doi: 10.1016/j.cej.2014.06.006
[2] LIN H, ZHANG H, HOH L Degradation of C. I. Acid Orange 7 in aqueous solution by a novel electro/Fe3O4/PDS process[J]. Journal of Hazardous Materials, 2014,276(9):182-191.
[3] LIU N, DING F, WENG C H, et al. Effective degradation of primary color direct azo dyes using Fe0 aggregates-activated persulfate process[J]. Journal of Environmental Management, 2018,206:565-576.
pmid: 29127929
[4] 易兵, 胡倩, 杨辉琼, 等. 酸性红37光催化降解动力学的响应曲面法优化及其转化机制[J]. 纺织学报, 2018,39(6):81-88.
YI Bing, HU Qian, YANG Huiqiong, et al. Photocatalytic degradation kinetics optimization of acid red 37 by reponse surface method and transformation mechanism[J]. Journal of Textile Research, 2018,39(6):81-88.
[5] VALERO-LUNA C, PALOMARES-SANCHEZ S A, RUIZ F. Catalytic activity of the barium hexaferrite with H2O2/visible light irradiation for degradation of Methylene Blue[J]. Catalysis Today, 2016,266:110-119.
doi: 10.1016/j.cattod.2015.08.049
[6] 欧阳磊, 丁耀彬, 朱丽华, 等. 钴掺杂铁酸铋活化过硫酸盐降解水中四溴双酚A的研究[J]. 环境科学, 2013,34(9):3507-3512.
OUYANG Lei, DING Yaobin, ZHU Lihua, et al. Efficient degradation of tetrabromobisphenol A in water by co-doped BiFeO3[J]. Environmental Science, 2013,34(9):3507-3512.
[7] TENG Y. Sulfate radical and its application in decontamination technologies[J]. Critical Reviews in Environmental Science & Technology, 2015,45(16):1756-1800.
[8] AND G P A, DIONYSIOU D D. Radical generation by the interaction of transition metals with common oxidants[J]. Environmental Science & Technology, 2004,38(13):3705-3712.
pmid: 15296324
[9] GUAN Y H, MA J, LI X C, et al. Influence of pH on the formation of sulfate and hydroxyl radicals in the UV/peroxymonosulfate system[J]. Environmental Science & Technology, 2011,45(21):9308-9314.
pmid: 21999357
[10] FURMAN O S. Mechanism of base activation of persulfate[J]. Environmental Science & Technology, 2010,44(16):6423-6428.
pmid: 20704244
[11] 蒋梦迪, 张清越, 季跃飞, 等. 热活化过硫酸盐降解三氯生[J]. 环境科学, 2018,39(4):1661-1667.
JIANG Mengdi, ZHANG Qingyue, JI Yuefei, et al. Degradation of Triclosan by heat activated persulfate oxidation[J]. Environmental Science, 2018,39(4):1661-1667.
[12] JOHNSON R L, TRATNYEK P G, JOHNSON R O. Persulfate persistence under thermal activation conditions[J]. Environmental Science & Technology, 2008,42(24):9350-9356.
pmid: 19174915
[13] 陈家斌, 魏成耀, 房聪, 等. 碳纳米管活化过二硫酸盐降解偶氮染料酸性橙7[J]. 中国环境科学, 2016,36(12):3618-3624.
CHEN Jiabin, WEI Chengyao, FANG Cong, et al. Decolorization of acid orange 7 by persulfate activated by carbon nanotube[J]. China Environmental Science, 2016,36(12):3618-3624.
[14] KOLTHOFF I M, MILLER I K. The chemistry of persulfate: I: the kinetics and mechanism of the decomposition of the persulfate ion in aqueous mediuml[J]. Journal of The American Chemical Society, 1951,73(7):1-30.
[15] ZALIBERA M, RAPA P, STASKO A, et al. Thermal generation of stable · SO 4 - spin trap adducts with super-hyperfine structure in their EPR spectra: an alternative EPR spin trapping assay for radical scavenging capacity determination in dimethylsulphoxide [J]. Free Radical Research, 2009,43(5):457-469.
pmid: 19353392
[16] DONADELLI J A, CARLOS L, ARQUES-SANZ A, et al. Kinetic and mechanistic analysis of azo dyes decolorization by ZVI-assisted Fenton systems: pH-dependent shift in the contributions of reductive and oxidative transformation pathways[J]. Applied Catalysis B: Environmental, 2018,231:51-61.
doi: 10.1016/j.apcatb.2018.02.057
[17] HOSSEINI H A, NEZHADALI A, DARROUDI M. Spectrophotometric study of complex formation between iodoquinol (IQ) and Co2+, Mn2+, Cd2+, Pb2+, and Zn2+ in DMF/MeOH binary mixed solvents[J]. Arabian Journal of Chemistry, 2017,10:293-296.
[18] YANG H, LIU H J, HU Z B, et al. Consideration on degradation kinetics and mechanism of thiamethoxam by reactive oxidative species (ROSs) during photocatalytic process[J]. Chemical Engineering Journal, 2014,245(1):24-33.
[19] YANG H, MEI L Y, WANG P C, et al. Photocatalytic degradation of norfloxacin on different TiO2-X polymorphs under visible light in water[J]. RSC Advances, 2017,7(72):45721-45732.
[20] YANG H, ZHOU S L, LIU H J, et al. Photocatalytic degradation of carbofuran in TiO2 aqueous solution:kinetics using design of experiments and mechanism by HPLC/MS/MS[J]. Journal of Environmental Sciences, 2013,25(8):1680-1686.
doi: 10.1016/S1001-0742(12)60217-4
[21] LUTZE H V, BREKENFELD J, NAUMOV S, et al. Radicals: new mechanistic aspects and economical considerations[J]. Water Research, 2017,129:509-519.
pmid: 29247911
[22] YANG Y, PIGNAGELLO J J, MA J, et al. Comparison of halide impacts on the efficiency of contaminant degradation by sulfate and hydroxyl radical-based advanced oxidation processes (AOPs)[J]. Environmental Science & Technology, 2014,48(4):2344-2351.
pmid: 24479380
[23] ZHOU L, ZHENG W, JI Y F, et al. Ferrous-activated persulfate oxidation of arsenic(III) and diuron in aquatic system[J]. Journal of Hazardous Materials, 2013,263:422-430.
pmid: 24220194
[24] YANG H, ZHUANG S, HU Q, et al, Competitive reactions of hydroxyl and sulfate radicals with sulfonamides in Fe2+/S2 O 8 2 - system: reaction kinetics, degradation mechanism and acute toxicity [J]. Chemical Engineering Journal, 2018,339:32-41.
[25] YANG H, ZHOU W C, YANG L P, et al. Flutriafol Degradation in Ag +/S2 O 8 2 - aqueous system: an experimental and theoretical investigation [J]. Environment Protection Engineering, 2018,44(2):57-72.
[1] QIAN Yifan, ZHOU Tang, ZHANG Liying, LIU Wanshuang, FENG Quan. Preparation of polyacrylonitrile / cellulose acetate / TiO2 composite nanofiber membrane and its photocatalytic degradation performance [J]. Journal of Textile Research, 2020, 41(05): 8-14.
[2] . Preparation of cobalt aluminate / ceramic honeycomb catalyst and application thereof in dye wastewater treatment#br# [J]. Journal of Textile Research, 2019, 40(03): 125-132.
[3] . Bentonite supported Zn-Co ozone catalyst for treatment of simulated dye wastewater#br# [J]. Journal of Textile Research, 2019, 40(03): 118-124.
[4] . Enhancement on anaerobic biological decolorization of azo dyes wastewater [J]. JOURNAL OF TEXTILE RESEARCH, 2018, 39(08): 83-87.
[5] . Photocatalytic degradetion kinetics optimization of acid red 37 by response surface method and transformation mechanism thereof [J]. JOURNAL OF TEXTILE RESEARCH, 2018, 39(06): 81-88.
[6] . Adsorption and visible-light photodegradation of Cu-organic framework to dye wastewater [J]. JOURNAL OF TEXTILE RESEARCH, 2018, 39(02): 112-118.
[7] . Research progress on deep treatment and recycling of  dye wastewater [J]. JOURNAL OF TEXTILE RESEARCH, 2017, 38(08): 172-180.
[8] . Thermal degradation behaviors and kinetics of intumescent flame-retardant cotton fabric [J]. JOURNAL OF TEXTILE RESEARCH, 2016, 37(12): 81-86.
[9] . New automatic and continuous production process of disperse dyes [J]. JOURNAL OF TEXTILE RESEARCH, 2016, 37(11): 80-85.
[10] . Determination of oxidative product aniline in degradation azo dye by liquid-phase chromatography coupled with mass spectrometry [J]. JOURNAL OF TEXTILE RESEARCH, 2015, 36(05): 69-73.
[11] . Determination of aromatic amines in terylene by ASE coupled with UPLC-MS/MS [J]. JOURNAL OF TEXTILE RESEARCH, 2014, 35(7): 94-0.
[12] . Analysis of adsorption decoloring effect of granular activated carbon for simulative reactive dye wastewater [J]. JOURNAL OF TEXTILE RESEARCH, 2013, 34(5): 70-75.
[13] . Application ofiInorganic-organic composite flocculant on dye wastewater treatment [J]. JOURNAL OF TEXTILE RESEARCH, 2013, 34(4): 98-103.
[14] . Application of Fe modified PAN nano-micron fiber catalyst to degradation of azo dye [J]. JOURNAL OF TEXTILE RESEARCH, 2013, 34(10): 76-0.
[15] . Research progress on treatment of dye wastewater by aquatic plants [J]. JOURNAL OF TEXTILE RESEARCH, 2012, 33(11): 146-152.
Viewed
Full text


Abstract

Cited

  Shared   
  Discussed   
No Suggested Reading articles found!