Development of novel chitosan schiff base derivatives for cationic dye removal: methyl orange model

Desalination and Water Treatment

Volumn 57, Issue 47, 2016, Pages 22632-22645

  El Sayed, E M ^a   Tamer, T M ^a   Omer, A M ^a   Mohy Eldin, M S ^a,b  

^a City of Scientific Research and Technological Applications ^*  (Egypt)

^b UNIVERSITY OF JEDDAH   (Saudi Arabia)

Author keywords

Chitosan; Dye removal; Methyl orange; Schiff base; TGA

Indexed keywords

ADSORPTION; CATION; DYE; EXPERIMENTAL STUDY; POLYSACCHARIDE; WATER TREATMENT;

EID: 84954178586     PISSN: 19443994     EISSN: 19443986     Source Type: Journal    
DOI: 10.1080/19443994.2015.1136694     Document Type: Article

References (96)

1. I.M.Banat, P.Nigam, D.Singh, R.Marchant, Microbial decolorization of textile-dyecontaining effluents:A review, Bioresour. Technol. 58 (1996) 217–227.10.1016/S0960-8524(96)00113-7
2. T.Robinson, G.McMullan, R.Marchant, P.Nigam, Remediation of dyes in textile effluent:A critical review on current treatment technologies with a proposed alternative, Bioresour. Technol. 77 (2001) 247–255.
3. M.S.Chiou, H.Y.Li, Equilibrium and kinetic modeling of adsorption of reactive dye on cross-linked chitosan beads, J. Hazard. Mater. 93 (2002) 233–248.10.1016/S0304-3894(02)00030-4
4. X.Y.Yang, B.Al-Duri, Application of branched pore diffusion model in the adsorption of reactive dyes on activated carbon, Chem. Eng. J. 83 (2001) 15–23.10.1016/S1385-8947(00)00233-3
5. M.S.Mottaleb, D.Littlejohn, Application of an HPLC-FTIR modified thermospray interface for analysis of dye samples, Anal. Sci. 17 (2001) 429–434.10.2116/analsci.17.429
6. S.M.Burkinshaw, O.Kabambe, Attempts to reduce water and chemical usage in the removal of bifunctional reactive dyes from cotton:Part 2 bis(vinyl sulfone), aminochlorotriazine/vinyl sulfone and bis(aminochlorotriazine/vinyl sulfone) dyes, Dyes Pigm. 88 (2011) 220–229.10.1016/j.dyepig.2010.07.001
7. P.C.Vandevivere, R.Bianchi, W.Verstraete, Review:Treatment and reuse of wastewater from the textile wet-processing industry:Review of emerging technologies, J. Chem. Technol. Biotechnol. 72 (1998) 289–302.10.1002/(ISSN)1097-4660
8. C.O’Neill, F.R.Hawkes, D.L.Hawkes, N.D.Lourenço, H.M.Pinheiro, W.Delée, Colour in textile effluents—Sources, measurement, discharge consents and simulation:A review, J. Chem. Technol. Biotechnol. 74 (1999) 1009–1018.10.1002/(ISSN)1097-4660
9. Y.Ho, T.Chiang, Y.Hsueh, Removal of basic dye from aqueous solution using tree fern as a biosorbent, Process Biochem. 40 (2005) 119–124.10.1016/j.procbio.2003.11.035
10. F.Derbyshire, M.Jagtoyen, R.Andrews, A.Rao, I.MartinGullon, E.Grulke, Carbon materials in environmental applications, in:L.R.Radovic (Ed.), Chemistry and Physics of Carbon, vol. 27, Marcel Dekker, New York, NY, 2001, pp. 1–66.
11. V.Vimonses, S.Lei, B.Jin, C.W.K.Chow, C.Saint, Adsorption of congo red by three Australian kaolins, Appl. Clay Sci. 43 (2009) 465–472.10.1016/j.clay.2008.11.008
12. S.L.Bartelt-Hunt, S.E.Burns, J.A.Smith, Nonionic organic solute sorption onto two organobentonites as a function of organic-carbon content, J. Colloid Interface Sci. 266 (2003) 251–258.10.1016/S0021-9797(03)00617-9
13. M.Akçay, G.Akçay, The removal of phenolic compounds from aqueous solutions by organophilic bentonite, J. Hazard. Mater. 113 (2004) 189–193.10.1016/j.jhazmat.2004.06.026
14. A.S.Özcan, B.Erdem, A.Özcan, Adsorption of Acid Blue 193 from aqueous solutions onto BTMA-bentonite, Colloids Surf. A:Physicochem. Eng. Aspects 266 (2005) 73–81.10.1016/j.colsurfa.2005.06.001
15. M.Özacar, İ.A.Şengilİ. Ayhan, A two stage batch adsorber design for methylene blue removal to minimize contact time, J. Environ. Manage. 80 (2006) 372–379.10.1016/j.jenvman.2005.10.004
16. A.Özcan, Ç.Ömeroğlu, Y.Erdoğan, A.S.Özcan, Modification of bentonite with a cationic surfactant:An adsorption study of textile dye Reactive Blue 19, J. Hazard. Mater. 140 (2007) 173–179.10.1016/j.jhazmat.2006.06.138
17. E.Alver, A.Ü.Metin, Anionic dye removal from aqueous solutions using modified zeolite:Adsorption kinetics and isotherm studies, Chem. Eng. J. 200–202 (2012) 59–67.10.1016/j.cej.2012.06.038
18. Y.Benkli, M.Can, M.Turan, M.Çelik, Modification of organo-zeolite surface for the removal of reactive azo dyes in fixed-bed reactors, Water Res. 39 (2005) 487–493.10.1016/j.watres.2004.10.008
19. N.N.Fathima, R.Aravindhan, J.R.Rao, B.U.Nair, Dye house wastewater treatment through advanced oxidation process using Cu-exchanged Y zeolite:A heterogeneous catalytic approach, Chemosphere 70 (2008) 1146–1151.10.1016/j.chemosphere.2007.07.033
20. E.Rosales, M.Pazos, M.Sanromán, T.Tavares, Application of zeolite-Arthrobacter viscosus system for the removal of heavy metal and dye:Chromium and Azure B, Desalination 284 (2012) 150–156.10.1016/j.desal.2011.08.049
21. N.Sapawe, A.Jalil, S.Triwahyono, M.Shah, R.Jusoh, N.Salleh, B.Hameed, A.Karim, Cost-effective microwave rapid synthesis of zeolite NaA for removal of methylene blue, Chem. Eng. J. 229 (2013) 388–398.10.1016/j.cej.2013.06.005
22. S.Sohrabnezhad, A.Pourahmad, Comparison absorption of new methylene blue dye in zeolite and nanocrystal zeolite, Desalination 256 (2010) 84–89.10.1016/j.desal.2010.02.009
23. S.Wang, H.Li, S.Xie, S.Liu, L.Xu, Physical and chemical regeneration of zeolitic adsorbents for dye removal in wastewater treatment, Chemosphere 65 (2006) 82–87.10.1016/j.chemosphere.2006.02.043
24. S.Wang, H.Li, L.Xu, Application of zeolite MCM-22 for basic dye removal from wastewater, J. Colloid Interface Sci. 295 (2006) 71–78.10.1016/j.jcis.2005.08.006
25. S.Wang, Z.Zhu, Characterisation and environmental application of an Australian natural zeolite for basic dye removal from aqueous solution, J. Hazard. Mater. 136 (2006) 946–952.10.1016/j.jhazmat.2006.01.038
26. X.S.Wang, Y.Zhou, Y.Jiang, C.Sun, The removal of basic dyes from aqueous solutions using agricultural by-products, J. Hazard. Mater. 157 (2008) 374–385.10.1016/j.jhazmat.2008.01.004
27. M.Doğan, H.Abak, M.Alkan, Biosorption of methylene blue from aqueous solutions by hazelnut shells:Equilibrium, parameters and isotherms, Water Air Soil Pollut. 192 (2008) 141–153.10.1007/s11270-008-9641-z
28. A.R.Khan, H.Tahir, F.Uddin, U.Hameed, Adsorption of methylene blue from aqueous solution on the surface of the wool fiber and cotton fiber, J. Appl. Sci. Environ. Manage. 9 (2005) 29–35.
29. A.Mittal, J.Mittal, A.Malviya, D.Kaur, V.Gupta, Adsorption of hazardous dye crystal violet from wastewater by waste materials, J. Colloid Interface Sci. 343 (2010) 463–473.10.1016/j.jcis.2009.11.060
30. A.L.Prasad, T.Santhi, Adsorption of hazardous cationic dyes from aqueous solution onto Acacia nilotica leaves as an eco-friendly adsorbent, Sustain. Environ. Res. 22 (2012) 113–122.
31. P.Sudamalla, P.Saravanan, M.Matheswaran, Optimization of operating parameters using response surface methodology for adsorption of crystal violet by activated carbon prepared from mango kernel, Environ. Res. 22 (2012) 1–7.
32. J.Torres-Pérez, M.Solache-Ríos, A.Colín-Cruz, Sorption and desorption of Dye rem azole yellow onto a Mexican surfactant-modified clinoptilolite-rich stuff and a carbonaceous material from pyrolysis of sewage sludge, Water Air Soil Pollut. 187 (2008) 303–313.
33. X.Wang, Invasive freshwater macrophyte alligator weed:Novel adsorbent for removal of malachite green from aqueous solution, Water Air Soil Pollut. 206 (2010) 215–223.10.1007/s11270-009-0097-6
34. G.Crini, Non-conventional low-cost adsorbents for dye removal:A review, Bioresour. Technol. 97 (2006) 1061–1085.10.1016/j.biortech.2005.05.001
35. L.D.Fiorentin, D.E.G.Trigueros, A.N.Módenes, F.R.Espinoza-Quiñones, N.C.Pereira, S.T.D.Barros, O.A.A.Santos, Biosorption of reactive blue 5G dye onto drying orange bagasse in batch system:Kinetic and equilibrium modeling, Chem. Eng. J. 163 (2010) 68–77.10.1016/j.cej.2010.07.043
36. C.P.Kaushik, R.Tuteja, N.Kaushik, J.K.Sharma, Minimization of organic chemical load in direct dyes effluent using low cost adsorbents, Chem. Eng. J. 155 (2009) 234–240.10.1016/j.cej.2009.07.042
37. G.Z.Kyzas, A decolorization technique with spent “Greek Coffee” Grounds as zero-cost adsorbents for industrial textile wastewaters, Materials 5 (2012) 2069–2087.10.3390/ma5112069
38. G.Z.Kyzas, M.Kostoglou, A.A.Vassiliou, N.K.Lazaridis, Treatment of real effluents from dyeing reactor:Experimental and modeling approach by adsorption onto chitosan, Chem. Eng. J. 168 (2011) 577–585.10.1016/j.cej.2011.01.026
39. G.Z.Kyzas, N.K.Lazaridis, A.C.Mitropoulos, Removal of dyes from aqueous solutions with untreated coffee residues as potential low-cost adsorbents:Equilibrium, reuse and thermodynamic approach, Chem. Eng. J. 189–190 (2012) 148–159.10.1016/j.cej.2012.02.045
40. R.S.Juang, R.L.Tseng, F.C.Wu, S.H.Lee, Adsorption behavior of reactive dyes from aqueous solutions on chitosan, J. Chem. Technol. Biotechnol. 70 (1997) 391–399.10.1002/(ISSN)1097-4660
41. D.Knorr, Dye binding properties of chitin and chitosan, J. Food Sci. 48 (1983) 36–37.10.1111/jfds.1983.48.issue-1
42. G.Annadurai, L.Y.Ling, J.F.Lee, Adsorption of reactive dye from an aqueous solution by chitosan:Isotherm, kinetic and thermodynamic analysis, J. Hazard. Mater. 152 (2008) 337–346.10.1016/j.jhazmat.2007.07.002
43. S.Chatterjee, S.Chatterjee, B.P.Chatterjee, A.K.Guha, Adsorptive removal of congo red, a carcinogenic textile dye by chitosan hydrobeads:Binding mechanism, equilibrium and kinetics, Colloids Surf., A:Physicochem. Eng. Aspects 299 (2007) 146–152.10.1016/j.colsurfa.2006.11.036
44. F.A.A.Tirkistani, Thermal analysis of some chitosan Schiff bases, Polym. Degrad. Stab. 60 (1998) 67–70.10.1016/S0141-3910(97)00020-7
45. J.E.dos Santos, E.R.Dockal, É.T.G.Cavalheiro, Synthesis and characterization of Schiff bases from chitosan and salicylaldehyde derivatives, Carbohydr. Polym. 60 (2005) 277–282.10.1016/j.carbpol.2004.12.008
46. A.M.Donia, A.A.Atia, K.Z.Elwakeel, Selective separation of mercury(II) using magnetic chitosan resin modified with Schiff's base derived from thiourea and glutaraldehyde, J. Hazard. Mater. 151 (2008) 372–379.10.1016/j.jhazmat.2007.05.083
47. H.M.Zalloum, Z.Al-Qodah, M.S.Mubarak. Copper adsorption on chitosan—Derived schiff bases, J. Macromol. Sci., Part A 46 (2008) 46-57.10.1080/10601320802515225
48. M.M.Islam, S.M.Masum, M.M.Rahman, M.A.I.Molla, A.A.Shaikh, S.K.Roy, Preparation of chitosan from shrimp shell and investigation of its properties, Int. J. Basic Appl. Sci. 11 (2011) 1–9.
49. G.Rigby, Patent Substantially Undegraded Deacetylated Chitin and Processes for Producing the Same, USA 2,040,879, (1936) 1–7.
50. E.A.Soliman, S.M.El-Kousy, H.M.Abd-Elbary, A.R.Abou-zeid, Low molecular weight chitosan-based schiff bases:Synthesis, characterization and antibacterial activity, Am. J. Food Technol. 8 (2013) 17–30.
51. I.Langmuir, The adsorption of gases on plane surfaces of glass, mica and platinum, J. Am. Chem. Soc. 40 (1918) 1361–1403.10.1021/ja02242a004
52. M.S.Elgeundi, Colour removal from textile effluents by adsorption techniques, Water Res. 25 (1991) 271–273.10.1016/0043-1354(91)90006-C
53. K.S.Low, C.K.Lee, Quaternized rice husk as sorbent for reactive dyes, Bioresour. Technol. 61 (1997) 121–125.10.1016/S0960-8524(97)00054-0
54. Z.Aksu, Biosorption of reactive dyes by dried activated sludge:Equilibrium and kinetic modelling, Biochem. Eng. J. 7 (2001) 79–84.10.1016/S1369-703X(00)00098-X
55. C.Namasivayam, D.Kavitha, Removal of Congo Red from water by adsorption onto activated carbon prepared from coir pith, an agricultural solid waste, Dyes Pigm. 54 (2002) 47–58.10.1016/S0143-7208(02)00025-6
56. H.Freundlich, Adsorption in solution, Z. Phys. Chemie 57 (1906) 384–470.
57. A.Pawlak, M.Mucha, Thermogravimetric and FTIR studies of chitosan blends, Thermochim. Acta 396 (2003) 153–166.10.1016/S0040-6031(02)00523-3
58. J.Zawadzki, H.Kaczmarek, Thermal treatment of chitosan in various conditions, Carbohydr. Polym. 80 (2010) 394–400.10.1016/j.carbpol.2009.11.037
59. K.Sreenivasan, Thermal stability studies of some chitosanmetal ion complexes using differential scanning calorimetry, Polym. Degrad. Stab. 52 (1996) 85–87.10.1016/0141-3910(95)00220-0
60. F.S.Kittur, K.V.Harish Prashanth, K.Udaya Sankar, R.N.Tharanathan, Characterization of chitin, chitosan and their carboxymethyl derivatives by differential scanning calorimetry, Carbohydr. Polym. 49 (2002) 185–193 10.1016/S0144-8617(01)00320-4
61. R.Riham, A.M.Fekry, Antimicrobial and anticorrosive activity of adsorbents based on chitosan schiff’s base, Int. J. Electrochem. Sci. 6 (2011) 2489–2508.
62. M.Diab, A.El-Sonbati, M.Al-Halawany, D.Bader, Thermal stability and degradation of chitosan modified by cinnamic acid, Open J. Polym. Chem. 02 (2012) 14–20.10.4236/ojpchem.2012.21003
63. W.Sajomsang, S.Tantayanon, V.Tangpasuthadol, M.Thatte, W.H.Daly, Synthesis and characterization of N-aryl Chitosan derivatives, Int. J. Biolog. Macromol. 43 (2008) 79–87.
64. S.Sashikala, S.Syed Shafi, Synthesis and characterization of chitosan schiff base derivatives, Der. Pharm. Lett. 6 (2014) 90-97.
65. T.F.Jiao, J.Zhou, J.Zhou, L.Gao, Y.Xing, X.Li, Synthesis and characterization of chitosan-based schiff base compounds with aromatic substituent groups, Iran. Polym. J. 20 (2011) 123–136.
66. R.Aravindhan, N.N.Fathima, J.R.Rao, B.U.Nair, Equilibrium and thermodynamic studies on the removal of basic black dye using calcium alginate beads, Colloids Surf., A:Physicochem. Eng. Aspects 299 (2007) 232–238.10.1016/j.colsurfa.2006.11.045
67. M.S.Mohy Eldin, S.A.El-Sakka, M.M.El-Masry, I.I.Abdel-Gawad, S.S.Garybe, Removal of methylene blue dye from the aqueous medium by nano polyacrylonitrile particles, Desalin. Water Treat. 44 (2012) 1–3.
68. G.L.Dotto, L.A.A.Pinto, Adsorption of food dyes onto chitosan:Optimization process and kinetic, Carbohydr. Polym. 84 (2011) 231–238.10.1016/j.carbpol.2010.11.028
69. H.Yoshida, A.Okamoto, T.Kataoka, Adsorption of acid dye on cross-linked chitosan fibers:Equilibria, Chem. Eng. Sci. 48 (1993) 2267–2272.10.1016/0009-2509(93)80242-I
70. F.C.Wu, R.L.Tseng, R.S.Juang, Comparative adsorption of metal and dye on flake- and bead-types of chitosans prepared from fishery wastes, J. Hazard. Mater. 73 (2000) 63–75.10.1016/S0304-3894(99)00168-5
71. M.S.Chiou, H.O.Pang-Yen, H.-Y.Li, Adsorption of anionic dyes in acid solutions using chemically cross-linked chitosan beads, Dyes Pigm. 60 (2004) 69–84.10.1016/S0143-7208(03)00140-2
72. E.Assaad, A.Azzouz, D.Nistor, A.V.Ursu, T.Sajin, D.N.Miron, F.Monette, P.Niquette, R.Hausler, Metal removal through synergic coagulation–flocculation using an optimized chitosan–montmorillonite system, Appl. Clay Sci. 37 (2007) 258–274.10.1016/j.clay.2007.02.007
73. A.Szyguła, E.Guibal, M.A.Palacın, M.Ruiz, A.M.Sastre, Removal of an anionic dye (Acid Blue 92) by coagulation–flocculation using chitosan, J. Environ. Manage. 90 (2009) 2979–2986.10.1016/j.jenvman.2009.04.002
74. M.Salman, M.Athar, U.Shafique, R.Rehman, S.Ameer, S.Z.Ali, M.Azeem, Removal of formaldehyde from aqueous solution by adsorption on kaolin and bentonite:A comparative study, Turk. J. Eng. Environ. Sci. 36 (2012) 263–270.
75. H.Hou, R.Zhou, P.Wu, L.Wu, Removal of Congo red dye from aqueous solution with hydroxyapatite/chitosan composite, Chem. Eng. J. 211–212 (2012) 336–342.10.1016/j.cej.2012.09.100
76. D.M.Ruthven, Principles of Adsorption and Adsorption Processes, John Wiley & Sons, New York, NY, 1984.
77. I.Uzun, Kinetics of the adsorption of reactive dyes by chitosan, Dyes Pigm. 70 (2006) 76–83.10.1016/j.dyepig.2005.04.016
78. W.J.Weber, J.C.Morris, Kinetics of adsorption of carbon from solutions, J. Sanit. Eng. Div. Am. Soc. Civ. Eng. 89 (1963) 31–63.
79. B.Noroozi, G.A.Sorial, H.Bahrami, M.Arami, Equilibrium and kinetic adsorption study of a cationic dye by a natural adsorbent—Silkworm pupa, J. Hazard. Mater. 139 (2007) 167–174.10.1016/j.jhazmat.2006.06.021
80. M.N.V.R.Kumar, A review of chitin and chitosan applications, React. Funct. Polym. 46 (2000) 1–27.10.1016/S1381-5148(00)00038-9
81. E.O.Augustine, S.H.Yuh, Equilibrium sorption of anionic dye from aqueous solution by palm kernel fiber as sorbent, Dyes Pigm. 74 (2007) 60–66.
82. G.McKay, G.Ramprasad, P.P.Mowli, Equilibrium studies for the adsorption of dyestuffs from aqueous solutions by low-cost materials, Water Air Soil Pollut. 29 (1986) 273–283.10.1007/BF00158759
83. Y.Ho, T.Chiang, Y.Hsueh, Removal of basic dye from aqueous solution using tree fern as a biosorbent, Process Biochem. 40 (2005) 119–124.10.1016/j.procbio.2003.11.035
84. H.Yoshida, S.Fukuda, O.Okamoto, T.Kataoka, Recovery of a direct dye and acid dye by adsorption on Chitosan fiber—Equilibria, Water Sci. Technol. 23 (1991) 1667–1676.
85. Y.C.Wong, Y.S.Szeto, W.H.Cheung, G.McKay, Adsorption of acid dyes on chitosan—Equilibrium isotherm analyses, Process Biochem. 39 (2004) 695–704.10.1016/S0032-9592(03)00152-3
86. G.Gibbs, J.M.Tobin, E.Guibal, Influence of Chitosan pre-protonation on reactive black five sorption isotherm and kinetics, Ind. Eng. Chem. Res. 43 (2004) 1–11.10.1021/ie030352p
87. A.W.Adamson, Physical Chemistry of Surface, Interscience Publishers Inc, New York, NY, 1960.
88. L.Y.Fraiji, D.M.Hayes, T.C.Werner, Static and dynamic fluorescence quenching experiments for the physical chemistry laboratory, J. Chem. Educ. 69 (1992) 424–428.10.1021/ed069p424
89. S.M.Venkat, D.M.Indra, C.S.Vimal, Use of bagasse fly ash as an adsorbent for the removal of brilliant green dye from aqueous solution, Dyes Pigm. 73 (2007) 269–278.
90. Y.Yao, H.Bing, X.Feifei, C.Xiaofeng, Equilibrium and kinetic studies of methyl orange adsorption on multiwalled carbon nanotubes, Chem. Eng. J. 170 (2011) 82–89.10.1016/j.cej.2011.03.031
91. H.Mahmoodian, O.Moradi, I.Tyagi, A.Maity, M.Asif, V.K.Gupta, Enhanced removal of methyl orange from aqueous solutions by polyHEMA–chitosan-MWCNT nano-composite, J. Mol. Liquids 202 (2015) 189–198.10.1016/j.molliq.2014.10.040
92. R.Deepika, M.Venkatesh Prabhu, M.Nandi Devi, Studies on the behavior of reactive dyes onto the cross-linked chitosan using adsorption isotherms, Int. J. Environ. Sci. 4 (2013) 323–351.
93. L.Zhang, P.Hu, J.Wang, Q.Liu, R.Huang, Adsorption of methyl orange (MO) by Zr (IV)-immobilized cross-linked chitosan/bentonite composite, Int. J. Biol. Macromol. 81 (2015) 818–827.10.1016/j.ijbiomac.2015.09.017
94. T.K.Saha, N.C.Bhoumik, S.Karmaker, M.G.Ahmed, H.Ichikawa, Y.Fukumori, Adsorption of methyl orange onto chitosan from aqueous solution, J. Water Resour. Prot. 2 (2010) 898–906.10.4236/jwarp.2010.210107
95. Y.Wang, G.Xia, C.Wu, J.Sun, R.Song, W.Huang, Porous chitosan doped with graphene oxide as highly effective adsorbent for methyl orange and amido black 10B, Carbohydr. Polym. 115 (2015) 686–693.10.1016/j.carbpol.2014.09.041
96. 3/magnetite nanoparticles composite adsorbent for kinetic, thermodynamic and isotherm studies of Methyl Orange adsorption, Chem. Eng. J. 259 (2015) 1–10.10.1016/j.cej.2014.07.109