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Degradation Pathway of the Naphthalene Azo Dye Intermediate 1-Diazo-2- Naphthol-4-Sulfonic Acid Using Fenton’S Reagent

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Degradation Pathway of the Naphthalene Azo Dye Intermediate 1-Diazo-2- Naphthol-4-Sulfonic Acid Using Fenton’S Reagent water research 46 (2012) 3859e3867 Available online at www.sciencedirect.com journal homepage: www.elsevier.com/locate/watres Degradation pathway of the naphthalene azo dye intermediate 1-diazo-2- naphthol-4-sulfonic acid using Fenton’s reagent Nanwen Zhu a,*, Lin Gu a,**, Haiping Yuan a, Ziyang Lou a, Liang Wang b, Xin Zhang a a School of Environmental Science and Engineering, Shanghai Jiao Tong University, Dongchuan road 800#, Shanghai 200240, PR China b Energy and Environment Division, Shanghai Advanced Research Institute, the Chinese Academy of Sciences, 99 Haike Rd, Pudong District, Shanghai 201210, PR China article info abstract Article history: Degradation of naphthalene dye intermediate 1-diazo-2- naphthol-4-sulfonic acid (1,2,4- Received 17 September 2011 Acid) by Fenton process has been studied in depth for the purpose of learning more Received in revised form about the reactions involved in the oxidation of 1,2,4-Acid. During 1,2,4-Acid oxidation, the 11 April 2012 solution color initially takes on a dark red, then to dark black associated with the formation Accepted 22 April 2012 of quinodial-type structures, and then goes to dark brown and gradually disappears, Available online 2 May 2012 indicating a fast degradation of azo group. The observed color changes of the solution are a result of main reaction intermediates, which can be an indicator of the level of oxi- Keywords: dization reached. Nevertheless, complete TOC removal is not accomplished, in accordance Fenton’s reaction with the presence of resistant carboxylic acids at the end of the reaction. The intermedi- Hydroxyl radical ates generated along the reaction time have been identified and quantified. UPLCe(ESI) 1,2,4-Acid eTOFeHRMS analysis allows the detection of 19 aromatic compounds of different size and complexity. Some of them share the same accurate mass but appear at different retention time, evidencing their different molecular structures. Heteroatom oxidation products like 2- SO4 have also been quantified and explanations of their release are proposed. Short-chain carboxylic acids are detected at long reaction time, as a previous step to complete the process of dye mineralization. Finally, considering all the findings of the present study and previous related works, the evolution from the original 1,2,4-Acid to the final products is proposed in a general reaction scheme. ª 2012 Elsevier Ltd. All rights reserved. 1. Introduction (usually exceeding 3 w.%), poor decolorization and biodegra- dation (Fu, 2002; Li, 1997; Lv et al., 2001). Various attempts Naphthalene and its derivatives are important industrial have been made to treat such kinds of wastewater, among chemicals and used extensively in dye and pharmacy indus- which, evaporation, polymeric absorption (Lv et al., 2001) and tries. The produced wastewater is always characterized by solvent extraction (Hu et al., 2005) have been reported so far. intense color, high toxicity, concentrated substrate and salt However, there are still many drawbacks that limit the large- * Corresponding author. Tel./fax: þ86 21 34203732. ** Corresponding author. Tel./fax: þ86 21 34200769. E-mail addresses: [email protected] (N. Zhu), [email protected] (L. Gu). 0043-1354/$ e see front matter ª 2012 Elsevier Ltd. All rights reserved. doi:10.1016/j.watres.2012.04.038 3860 water research 46 (2012) 3859e3867 scale application of these methods in real wastewaters. For example, polymeric adsorption is confronted with higher 2. Experimental section consumption rate, heavy contamination of the resin by some pollutants, as well as the difficulties of resin regeneration after 2.1. Chemicals adsorption saturation. Evaporation often produces volatile organic compounds (VOCs), causing the problem of secondary Commercial 1-diazo-2- naphthol-4-sulfonic acid (C10H6N2O4S, environmental pollution. SanFeng) with a purity degree of 98%, the rest being of inor- Naphthalene ring has delocalization-conjugated bond ganic nature, was used as received. Its chemical structure is composed of ten carbon atoms and this structure is quite shown in Fig. 1. All chemicals were prepared using high-purity U stable. These compounds are generally recalcitrant to biolog- water from a Millipore system with a resistivity of 18.2 M cm. ical treatment and constitute a source of pollution due to both Perchloric acid, ferrous sulfate, and hydrogen peroxide (33% their toxic and mutagenic effect on humans, fish, algae and w/v) were purchased from Merck. microorganisms (Fedorak and Clemente, 2005). Advanced oxidation processes (AOPs) are an interesting treatment 2.2. Experimental setup option for this type of wastewaters, because of their great potential to oxidize, partially or totally, numerous organic All experiments were carried out at batch mode using an compounds (Pandey et al., 2011). This process is based on the acrylic reactor with a working volume of 250 mL. The Æ formation of hydroxyl radical (HO$), which is a more powerful temperature was 28 2 C during the reaction. The reactor oxidant (E0 2.8 V) than the chemical reagents commonly used was also equipped with a mixer to ensure appropriate agita- 0 0 tion. Synthetic wastewater containing 1 mM 1,2,4-Acid was for this purpose, such as ozone (E 2.0 V) or H2O2 (E 1.8 V). Rate constant in AOPs for organic compounds is several orders of dissolved with high-purity water and then pH-adjusted with magnitude higher than those reported for other processes 0.2 N NaOH or 0.2 N H2SO4 solutions. The initial pH was such as ozonation (Szpyrkowicz et al., 2001; Gotvajn et al., adjusted to 2.5 based on the results of preliminary experi- 2011; Duran-Moreno et al., 2011). Due to its high reactivity, ments (Gu et al., 2011). After pH adjustment, a calculated the hydroxyl radical is very unstable and must be continu- amount of catalyst ferrous sulfate (1.5 mM) was added as the 2þ ously produced in situ by means of chemical or photochem- source of Fe in this experiment. Then, H2O2 (30 mM) was ical reactions (Nogueira et al., 2011; Min et al., 2011). added into the reactor to start the reaction. At selected time One of the most effective AOPs consists of the utilization of intervals, 1 mL of the reaction mixture was taken and imme- 2þ diately injected into 0.1 N NaOH to increase the pH to 10 to Fenton’s reagent, a combination of H2O2 and Fe . In this þ process, H O decomposes catalytically by means of Fe2 at terminate the reaction (Lu et al., 2005; Anotai et al., 2006). The 2 2 m acid pH, giving rise to hydroxyl radicals samples were filtered through 0.45 m membrane filters to remove the precipitates formed. Filtered samples were then analyzed for 1,2,4-Acid removal and TOC removal. 2þþ ! 3þ þ $ þ À Fe H2O2 Fe HO OH (1) All the experiments were conducted at least three times The application of Fenton’s reagent as an oxidant for and the experimental data are the average of at least three Æ wastewater treatment is attractive, however, in recent years, measurements with an accuracy of 5%. the goal to perform the AOPs has been converted from one step elimination to partially degrade the pollutants. This is 2.3. Chemical analysis aimed to enhance the biodegradability and generate a new effluent able to be treated in a biological plant. Therefore, TOC was determined with a TOC Shimadzu 5000 A analyzer. A monitoring of the intermediates of the chemical treatment is Sulfate and carboxylic acids concentrations were measured essential to understand and predict the biological compati- with a Dionex DX-600 ion chromatograph using a Dionex  bility of the Fenton-treated effluents. The mechanism in Ionpac AS11-HC4 250 nm column. Fenton’s reaction is complicated and schemes of reaction are The original dye degradation was monitored by High generally complex (Peral et al., 2008). The chemical analysis is Performance Liquid Chromatography (C-18 Phenomenex e not an easy task in the case of dye molecules, since they LUNA column) and UV Vis detection (Agilent, Series 1100) at À1 usually are large units that produce complex intermediates 254 nm wavelength. The mobile phase were 5 g L KH2PO4 (A), À1 À1 after one oxidation event, or they may produce low concen- 1.2 g L NaH2PO4 and 1 ml L acetic acid. The column tration of small polar compounds that are difficult to detect. temperature was 25 C. The goal of the present work, carried out at a batch scale, is The elution gradient program for anions quantification to gain knowledge and characterize the chemical substances was a 5 min prerun with 20 mM NaOH, followed by injection of that are involved along the Fenton degradation of complex azo dye molecule, especially that of naphthalene dye interme- diate. To date, literatures concerning the oxidation of 1,2,4- Acid using AOPs are scarcely reported elsewhere. This study also analyzes the color changes during the Fenton’s oxidation of 1,2,4-Acid in order to evaluate the relations between the intermediates evolution and the development of the color observed in the solution. Finally, a degradation pathway of 1,2,4-Acid by Fenton oxidation is proposed. Fig. 1 e Chemical structure of 1,2,4-Acid. water research 46 (2012) 3859e3867 3861 þ 20 mM NaOH for 8 min with 35 mM NaOH for 7 min. The flow (Lu et al., 2009), for a given Fe2 and parent concentration, À1 rate was 1.5 mL min . The gradient program for carboxylate increasing the starting concentration of H2O2 does not always anions analysis consisted of a 10 min prerun with 1 mM NaOH, correspond to the faster oxidation of the target substance. As 10 min with 15 mM NaOH, 10 min with 30 mM NaOH and the reaction Kinetic Model predicted (Ledakowicz et al., 2000), À 10 min with 60 mM NaOH.
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