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Cellulose

, Volume 26, Issue 17, pp 9207–9227 | Cite as

Chemical modification of cellulose with zwitterion moieties used in the uptake of red Congo dye from aqueous media

  • Cesar M. Laureano-Anzaldo
  • Nadia B. Haro-Mares
  • Juan C. Meza-Contreras
  • Jorge R. Robledo-Ortíz
  • Ricardo Manríquez-GonzálezEmail author
Original Research
  • 112 Downloads

Abstract

Two zwitterionic celluloses were prepared by grafting amphoteric precursors AS (APTES with 1,4 butane sultone) and TAS (Trimethoxysilylpropyldiethylenetriamine with 1,4 butane sultone) onto activated cellulose with NH4OH in a heterogeneous system. Information about the zwitterionic modification in celluloses was achieved by FT-IR and 13C/29Si NMR CP/MAS spectroscopy. These analyses demonstrated the chemical structure and level of grafting of the zwitterionic precursors onto cellulose. Moreover, grafting degree (GD) of Cel-AS (31.5%) and Cel-TAS (16.6%) was evaluated by Elemental analysis. The amount of free amino groups from the grafted residues in both samples was tested by ninhydrin method. Here, results demonstrated that around a sixth part of the grafting in Cel-AS remains as aminopropylsilane. In the case of Cel-TAS, the half of butane sultone was bonded to a secondary nitrogen resulting in three possible zwitterionic configurations. These zwitterionic materials were used as adsorbents of Congo red dye in aqueous solution at different concentrations. Uptake experimental data fit well with Langmuir model, with a maximum theoretical adsorption capacity of 541.8 mg g−1 for Cel-TAS and 81.2 mg g−1 in Cel-AS at pH 6. Kinetics results for these systems showed the limiting rate step driven by chemisorption process, since they followed a pseudo-second order model. Finally, zwitterionic modification of cellulose with TAS conferred an increase on more than eightfold of Congo red adsorption capacity in comparison with unmodified cellulose.

Graphic abstract

Keywords

Zwitterionic moieties Cellulose modification Dye uptake Congo red 

Notes

Acknowledgments

Authors thank to the National Council of Science and Technology (CONACYT) in Mexico for the graduate scholarship of Cesar M. Laureano-Anzaldo as well as for the financial support received under the Basic Science project (CB2015/253376). Also, we acknowledge to Institute of transdisciplinary research (ITRANS) from University of Guadalajara for the NMR facilities.

Supplementary material

10570_2019_2717_MOESM1_ESM.docx (238 kb)
Supplementary material 1 (DOCX 237 kb)

References

  1. Acemioğlu B (2004) Adsorption of Congo red from aqueous solution onto calcium-rich fly ash. J Colloid Interface Sci 274:371–379.  https://doi.org/10.1016/j.jcis.2004.03.019 CrossRefPubMedGoogle Scholar
  2. Afkhami A, Moosavi R (2010) Adsorptive removal of Congo red, a carcinogenic textile dye, from aqueous solutions by maghemite nanoparticles. J Hazard Mater 174:398–403.  https://doi.org/10.1016/j.jhazmat.2009.09.066 CrossRefPubMedGoogle Scholar
  3. Allan G, Delgado E, Lopez-Dellamary F (1993) A new interfibre system for paper involving zwitterions. Prod Papermak 2:1101–1138Google Scholar
  4. Ansari M, Kumar R, Ansari S, Ansari S, Barakat M, Alshahrie A, Cho M (2017) Anion selective pTSA polyanilineraphene oxide-multiwalled carbon nanotube composite for Cr(VI) and Congo red adsorption. J Colloid Interface Sci 496:407–415.  https://doi.org/10.1016/j.jcis.2017.02.034 CrossRefPubMedGoogle Scholar
  5. Arami M, Yousefi N, Mahmoodi N, Tabrizi N (2006) Equilibrium and kinetics studies for the adsorption of direct and acid dyes from aqueous solution by soy meal hull. J Hazard Mater 135:171–179.  https://doi.org/10.1016/j.jhazmat.2005.11.044 CrossRefPubMedGoogle Scholar
  6. Arasawa H, Odawara C, Yokoyama R, Saitoh H, Yamauchi T, Tsubokawa N (2004) Grafting of zwitterion-type polymers onto silica gel surface and their properties. React Funct Polym 61:153–161.  https://doi.org/10.1016/j.reactfunctpolym.2004.04.006 CrossRefGoogle Scholar
  7. Bhattacharyya R, Kumar S (2013) Kinetic and equilibrium modeling for adsorption of textile dyes in aqueous solutions by carboxymethyl cellulose/poly(acrylamide-co-hydroxyethylmethacrylate) semi-interpenetrating network hydrogel. Polym Sci 53:2439–2454.  https://doi.org/10.1002/pen.23501 CrossRefGoogle Scholar
  8. Brotzel F, Chu Y, Mayr H (2007) Nucleophilicities of primary and secondary amines in water. J Org Chem 72:3679–3688.  https://doi.org/10.1021/jo062586z CrossRefPubMedGoogle Scholar
  9. Chakraborty S, Chowdhury S, Saha P (2011) Adsorption of crystal violet from aqueous solution onto NaOH-modified rice husk. Carbohydr Polym 86:1533–1541.  https://doi.org/10.1016/j.carbpol.2011.06.058 CrossRefGoogle Scholar
  10. Chatterjee S, Chatterjee S, Chatterjee B, Guha A (2007) Adsorptive removal of congo red, a carcinogenic textile dye by chitosan hydrobeads: binding mechanism, equilibrium and kinetics. Colloids Surfaces A: Physicochem Eng Aspects 299:146–152.  https://doi.org/10.1016/j.colsurfa.2006.11.036 CrossRefGoogle Scholar
  11. Chatterjee S, Lee D, Lee M, Woo S (2009) Congo red adsorption form aqueous solutions by using chitosan hydrogel beads impregnated with nonionic or anionic surfactant. Bioresour Technol 100:3862–3868.  https://doi.org/10.1016/j.biortech.2009.03.023 CrossRefPubMedGoogle Scholar
  12. Chiong T, Lau S, Lek Z, Koh B, Danquah M (2016) Enzymatic treatment of methyl orange dye in synthetic wastewater by plant-based peroxidase enzymes. J Environ Chem Eng 4:2500–2509.  https://doi.org/10.1016/j.jece.2016.04.030 CrossRefGoogle Scholar
  13. Chowdhury S, Mishra R, Saha P, Kushwaha P (2011) Adsorption thermodynamics, kinetics and isosteric heat of adsorption of malachite green onto chemically modified rice husk. Desalination 265:159–168.  https://doi.org/10.1016/j.desal.2010.07.047 CrossRefGoogle Scholar
  14. Da Fonseca M, Airoldi C (2000) New layered inorganic-organic nanocomposites containing n-propylmercapto copper phyllosilicates. J Mater Chem 10:1457–1463.  https://doi.org/10.1039/B001556N CrossRefGoogle Scholar
  15. Dawood S, Kanti T (2012) Removal of anionic dye Congo red from aqueous solution by raw pine and acid-treated pine cone powder as adsorbent: equilibrium, thermodynamic, kinetics, mechanism and process design. Water Res 46:1933–1946.  https://doi.org/10.1016/j.watres.2012.01.009 CrossRefPubMedGoogle Scholar
  16. De Lima A, Mbengue A, San Gil R, Ronconi C, Mota C (2014) Synthesis of amine functionalized mesoporous silica basic catalysts for biodiesel production. Catal Today 226:210–216.  https://doi.org/10.1016/j.cattod.2014.01.017 CrossRefGoogle Scholar
  17. Dey R, Oliveira F, Airoldi C (2008) Mesoporous silica functionalized with diethylentriamine moieties for metal removal and thermodynamics of cation-basic center interactions. Colloids Surfaces A: Physicochem Eng Aspects 324:41–46.  https://doi.org/10.1016/j.colsurfa.2008.03.030 CrossRefGoogle Scholar
  18. Dos Santos T, Bourrelly S, Llewellyn P, Carneiro J, Machado C (2015) Adsorption of CO2 on amine-functionalised MCM-41: experimental and theoretical studies. Phys Chem Chem Phys 17:11095–11102.  https://doi.org/10.1039/c5cp00581g CrossRefPubMedGoogle Scholar
  19. Du Q, Sun J, Li Y, Yang X, Wang X, Wang Z, Xia L (2014) Highly enhanced adsorption of congo red onto graphene oxide/chitosan fibers by wet-chemical etching off silica nanoparticles. Chem Eng J 245:99–106.  https://doi.org/10.1016/j.cej.2014.02.006 CrossRefGoogle Scholar
  20. Ek S, Iiskola E, Niinistö L (2004) A 29Si and 13C CP/MAS NMR study on the Surface species of gas-phase-deposited γ-aminopropylalkoxysilanes on heat-treated silica. J Phys Chem B 108:11454–11463.  https://doi.org/10.1021/jp048927z CrossRefGoogle Scholar
  21. El-Zahhar A, Awwad N, El-Katori E (2014) Removal of bromophenol blue dye from industrial wastewater by synthesizing polymer-clay composite. J Mol Liq 199:454–461.  https://doi.org/10.1016/j.molliq.2014.07.034 CrossRefGoogle Scholar
  22. Estephan Z, Jaber J, Schlenoff J (2010) Zwitterion-stabilized silica nanoparticles: toward nonstick nano. Langmuir 26:16884–16889.  https://doi.org/10.1021/la103095d CrossRefPubMedGoogle Scholar
  23. French AD (2014) Idealized powder diffraction patterns for cellulose polymorphs. Cellulose 21:885–896.  https://doi.org/10.1007/s10570-013-0030-4 CrossRefGoogle Scholar
  24. French AD, Santiago Cintrón M (2013) Cellulose polymorphy, crystallite size, and the segal crystallinity index. Cellulose 20:583–588.  https://doi.org/10.1007/s10570-012-9833-y CrossRefGoogle Scholar
  25. Freundlich H (1906) Über die adsorption in lösungen. Z Phys Chem 57:385–470.  https://doi.org/10.1515/zpch-1907-5723 CrossRefGoogle Scholar
  26. Friedman M (2004) Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences. J Agric Food Chem 52:385–406.  https://doi.org/10.1021/jf030490p CrossRefPubMedGoogle Scholar
  27. Garg V, Kumar R, Gupta R (2004) Removal of malachite Green dye from aqueous solution by adsorption using agro-industry waste: a case study of pProsopis cineraria. Dyes and Pigm 62:1–10.  https://doi.org/10.1016/S0143-7208(03)00224-9 CrossRefGoogle Scholar
  28. Gupta V, Khamparia S, Tyagi I, Jaspal D, Malviya A (2015) Decolorization of mixtures: a critical review. Glob J Environ Sci Manag 1:71–94.  https://doi.org/10.7508/gjesm.2015.01.007 CrossRefGoogle Scholar
  29. Gürses A, Açikyildiz M, Güneş K, Gürses S (2016) Dyes and pigments. Springer, SwitzerlandCrossRefGoogle Scholar
  30. Heinze T (1998) New ionic polymers by cellulose functionalization. Macromol Chem Phys 199:2341–2364.  https://doi.org/10.1002/(SICI)1521-3935(19981101)199:11%3c2341:AID-MACP2341%3e3.0.CO;2-J CrossRefGoogle Scholar
  31. Heinze T, Genco T, Petzold-Welcke K, Wondraczek H (2012) Synthesis and characterization of aminocellulose sulfates. Cellulose 19:1305–1313.  https://doi.org/10.1007/s10570-012-9725-1 CrossRefGoogle Scholar
  32. Ho Y, McKay G (1999) Pseudo-second order model for sorption processes. Process Biochem 34:451–465.  https://doi.org/10.1016/S0032-9592(98)00112-5 CrossRefGoogle Scholar
  33. Holkar C, Jadhav A, Pinjari D, Mahamuni N, Pandit A (2016) A critical review on textile wastewater treatments: possible approaches. J Environ Manag 182:351–366.  https://doi.org/10.1016/j.jenvman.2016.07.090 CrossRefGoogle Scholar
  34. Hwang M, Chen K (1993) The removal of color from effluents using polyamide-epichlorohydrin-cellulose polymer. I. Preparation and use in direct dye removal. J Appl Polym Sci 48:299–311.  https://doi.org/10.1002/app.1993.070480214 CrossRefGoogle Scholar
  35. Jin L, Li W, Xu Q, Sun Q (2015) Amino-functionalized nanocrystalline cellulose as an adsorbent for anionic dyes. Cellulose 22:2443–2456.  https://doi.org/10.1007/s10570-015-0649-4 CrossRefGoogle Scholar
  36. Kanthasamy R, Mbaraka I, Shanks B, Larsen S (2007) Solid-state MAS NMR studies of sulfonic acid-functionalized SBA-15. Appl Magn Reson 32:513–526.  https://doi.org/10.1007/s00723-007-0034-z CrossRefGoogle Scholar
  37. Koga H, Kitaoka T, Isogai A (2011) In situ modification of cellulose paper with amino groups for catalytic applications. J Mater Chem 21:9356–9361.  https://doi.org/10.1039/c1jm10543d CrossRefGoogle Scholar
  38. Kyzas G, Lazaridis N, Bikiaris D (2013) Optimization od chitosan and β-cyclodectrin molecularly imprinted polymer synthesis for dye adsorption. Carbohydr Polym 91:198–208.  https://doi.org/10.1016/j.carbpol.2012.08.016 CrossRefPubMedGoogle Scholar
  39. Lagregen S (1898) Zur theorie der sogenannten adsorption gelöster stoffe. Kungliga Svenska Vetenskapsakademiens Handligar 24:1–39Google Scholar
  40. Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403.  https://doi.org/10.1021/ja02242a004 CrossRefGoogle Scholar
  41. Lian L, Guo L, Guo C (2009) Adsorption of Congo red from aqueous solutions onto Ca-bentonite. J Hazard Mater 161:126–131.  https://doi.org/10.1016/j.jhazmat.2008.03.063 CrossRefPubMedGoogle Scholar
  42. Litt M, Matsuda T (1975) Siloxane zwitterions: synthesis and Surface properties of crosslinked polymers. J Appl Polym Sci 19:1221–1225.  https://doi.org/10.1002/app.1975.070190502 CrossRefGoogle Scholar
  43. Liu S, Ding Y, Li P, Diao K (2014) Adsorption of the anionic dye congo red from aqueous solution onto natural zeolites modified with N, N-dimethyldehydroabietylamine oxide”. Chem Eng J 248:135–144.  https://doi.org/10.1016/j.cej.2014.03.026 CrossRefGoogle Scholar
  44. Mane V, Babu V (2013) Kinetic and equilibrium studies on the removal of congo red from aqueous solution using Eucalyptus Wood (eucaliptus globulus) saw dust. J Taiwan Inst Chem Eng 44:81–88.  https://doi.org/10.1016/j.jtice.2012.09.013 CrossRefGoogle Scholar
  45. Manriquez R, López-Dellamary F, Frydel J, Emmler T, Breitzke H, Buntkowsky G, Limbach H, Shenderovich I (2009) Solid-state NMR studies of aminocarboxylic saltt bridges in l-Lysine modified cellulose. J Phys Chem B 113:934–940.  https://doi.org/10.1021/jp8081968 CrossRefPubMedGoogle Scholar
  46. Mazeau K, Wyszomirsky M (2012) Modelling of Congo red adsorption on the hydrophobic surface of cellulose using molecular dynamics. Cellulose 19:1495–1506.  https://doi.org/10.1007/s10570-012-9757-6 CrossRefGoogle Scholar
  47. Meza-Contreras JC, Manríquez-González R, Gutiérrez-Ortega JA, González-García Y (2018) XRD and solid state 13C-NMR evaluation of the crystallinity enhancement of 13C-labeled bacterial cellulose biosynthesized by Komagataeibacter xylinus under different stimuli: a comparative strategy of analyses. Carbohyd Res 461:51–59.  https://doi.org/10.1016/j.carres.2018.03.005 CrossRefGoogle Scholar
  48. Mittal N, Samanta A, Sarkar P (2015) Gupta R (2015) Post combustion CO2 using N-(3-trimethoxysilylpropyl) diethylenetriamine-grafted solid adsorbent. Energy Sci Eng 3:207–220.  https://doi.org/10.1002/ese3.64 CrossRefGoogle Scholar
  49. Moore S, Stein W (1954) A modified ninhydrin reagent for the photometric determination of amino acids and related compounds. J Biol Chem 211:907–913PubMedGoogle Scholar
  50. Muskoya S, Ngila J, Moodley B, Petrik L, Kindness A (2011) Synthesis, characterization, and adsorption kinetic studies of ethylendiamine modified cellulose for removal of Cd and Pb. Anal Lett 44:1925–1936.  https://doi.org/10.1080/00032719.2010.539736 CrossRefGoogle Scholar
  51. Muthu S (2014) Roadmap to sustainable textiles and clothing: Eco-friendly raw materials, technologies, and processing methods. Springer, BerlinCrossRefGoogle Scholar
  52. Nair V, Panigrahy A, Vinu R (2014) Development of novel chitosan-lignin composites for adsorption of dyes and metal ions from wastewater. Chem Eng J 254:491–502.  https://doi.org/10.1016/j.cej.2014.05.045 CrossRefGoogle Scholar
  53. Ng N, Mohd S, Marie O, Mukti R, Juan J (2013) Sulfonic acid functionalized MCM-41 as solid acid catalyst for tert-butylation of hydroquinone enhanced by microwave heating. Appl Catal A General 450:34–41.  https://doi.org/10.1016/j.apcata.2012.09.055 CrossRefGoogle Scholar
  54. Parasuraman D, Serpe M (2011) Poly (N-isopropylacrylamide) microgels for organic dye removal from water. ACS Appl Mater Interfaces 3:2732–2737.  https://doi.org/10.1021/am2005288 CrossRefPubMedGoogle Scholar
  55. Pasternack R, Amy S, Chabal Y (2008) Attachment of 3-(aminopropyl)triethoxysilane on silicon oxide surfaces: dependence on solution temperature. Langmuir 24:12963–12971.  https://doi.org/10.1021/la8024827 CrossRefPubMedGoogle Scholar
  56. Pavan F, Dias S, Lima E, Benvenutti E (2008) Removal of Congo red from aqueous solution by anilinepropylsilica xerogel. Dyes Pigm 76:64–69.  https://doi.org/10.1016/j.dyepig.2006.08.027 CrossRefGoogle Scholar
  57. Peña-Alonso R, Rubio F, Rubio J, Oteo J (2007) Study of the hydrolysis and condensation of γ-aminopropyltriethoxysilane by FT-IR spectroscopy. J Mater Sci 42:595–603.  https://doi.org/10.4236/jbnb.2014.54028 CrossRefGoogle Scholar
  58. Robinson T, McMullan G, Marchant R, Nigam P (2001) Remediation of dyes in textile effluent: a critical review on current treatment technologies with a proposed alternative. Bioresour Technol 77:247–255.  https://doi.org/10.1016/S0960-8524(00)00080-8 CrossRefPubMedGoogle Scholar
  59. Roy D, Semasarilar M, Gurhrie J, Perrier S (2009) Cellulose modification by polymer grafting: a review. Chem Soc Rev 38:2046–2064.  https://doi.org/10.1039/B808639G CrossRefPubMedGoogle Scholar
  60. Shanghi R, Bhattacharya B (2002) Review on decolorization of aqueous dye solutions by low cost adsorbents. Color Technol 118:256–270.  https://doi.org/10.1111/j.1478-4408.2002.tb00109.x CrossRefGoogle Scholar
  61. Shi H, Li W, Zhong L, Xu C (2014) Methylene blue adsorption from aqueous solution by magnetic cellulose/graphene oxide composite: equilibrium, kinetics, and thermodynamics. Ind Eng Chem Res 53:1108–1118.  https://doi.org/10.1021/ie4027154 CrossRefGoogle Scholar
  62. Silva L, Lima L, Silva F, Matos J, Santos M, Santos L, Sousa K, Filho E (2013) Dye anionic sorption in aqueous solution onto a cellulose surface chemically modified with aminoethanethiol. Chem Eng J 218:89–98.  https://doi.org/10.1016/j.cej.2012.11.118 CrossRefGoogle Scholar
  63. Socrates G (2001) Infrared and raman characteristic group frequencies. Wiley, HobokenGoogle Scholar
  64. Suzuki T, Nakamura T, Sudo E, Akimoto Y, Yano K (2008) Enhancement of catalytic performance by creating Shell layers on sulfonic acid-functionalized monodispersed mesoporous silica spheres. J Catal 258:265–272.  https://doi.org/10.1016/j.jcat.2008.06.021 CrossRefGoogle Scholar
  65. Tripathi B, Shahi V (2009) 3-[[3-(triethoxysilyl)propyl]amino]propane-1-sulfonic acid-poly(vinyl alcohol) cross-linked zwitterionic polymer electrolyte membranes for direct methanol fuel cell applications. ACS Appl Mater Interfaces 1:1002–1012.  https://doi.org/10.1021/am800228s CrossRefPubMedGoogle Scholar
  66. Vimonses S, Lei S, Jin B, Chow C, Saint C (2009) Kinetic and equilibrium isotherm analysis of Congo red adsorption by clay materials. Chem Eng J 148:354–364.  https://doi.org/10.1016/j.cej.2008.09.009 CrossRefGoogle Scholar
  67. Wang L, Li J (2013) Adsorption of C.I. reactive red 228 dye from aqueous solution by modified cellulose from flax shive: kinetics, equilibrium, and thermodynamics. Ind Crops Prod 42:153–158.  https://doi.org/10.1016/j.indcrop.2012.05.031 CrossRefGoogle Scholar
  68. Wang L, Mao C, Sui N, Liu M, Yu W (2016) Graphene oxide/ferroferric oxide/polyethylenimine nanocomposites for congo red adsorption from water. Environ Technol 38:996–1004.  https://doi.org/10.1080/09593330.2016.1215352 CrossRefPubMedGoogle Scholar
  69. Weber W, Morris J (1963) Kinetics of adsorption on carbon from solution. J Sanit Eng Div 89:31–60Google Scholar
  70. Woodcock S, Henrissat B, Sugiyama J (1995) Docking of congo red to the surface of crystalline cellulose using molecular mechanics. Biopolymers 36:201–210.  https://doi.org/10.1002/bip.360360208 CrossRefPubMedGoogle Scholar
  71. Yamaki S, Barros D, Garcia C, Socoloski P, Oliveira O, Atvars T (2005) Spectroscopic studies of the intermolecular interactions of congo red and tinopal CBS with modified cellulose fibers. Langmuir 21:5414–5420.  https://doi.org/10.1021/la046842j CrossRefPubMedGoogle Scholar
  72. Yang X, Zhao X, Liu C, Zheng Y, Qian S (2009) Decolorization of azo, triphenylmethane and anthraquinone dyes by a newly isolated Trametes sp. SQ01 and its laccase. Process Biochem 44:1185–1189.  https://doi.org/10.1016/j.procbio.2009.06.015 CrossRefGoogle Scholar
  73. Yang M, Xu F, Wang C, Liu X, Yan P, Li P, Welz-Biermann U (2012) Synthesis, characterization, and catalytic properties of two zwitterionic hybrid SBA-15 mesoporous silicas. Eur J Inorg Chem 2012:4500–4506.  https://doi.org/10.1002/ejic.201200498 CrossRefGoogle Scholar
  74. Zhu Z, Li W (2013) Efficient adsorption and desorption of Pb 2+ from aqueous solution. J Environ Chem Eng 1:838–843.  https://doi.org/10.1016/j.jece.2013.07.022 CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Department of Wood, Cellulose and Paper, CUCEIUniversity of GuadalajaraGuadalajaraMexico

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