Advertisement

Adsorption of paraquat from water by insoluble cyclodextrin polymer crosslinked with 1,2,3,4-butanetetracarboxylic acid

  • Jatupol JunthipEmail author
  • Warangkana Promma
  • Somchai Sonsupap
  • Chaichat Boonyanusith
Original Research
  • 10 Downloads

Abstract

An insoluble polymer was elaborated by crosslinking reaction between β-CD (β-cyclodextrin) and BTCA (1,2,3,4-butanetetracarboxylic acid) and it was firstly applied in adsorption of paraquat (PQ) from water. This insoluble polymer was synthesized at 180 °C for 30 min which displayed 74.1% of reaction yield, 3.80 mmol g− 1 of ion exchange capacity (IEC) and 0.18 mmol g− 1 of β-CD content. Physicochemical properties were evaluated by attenuated total reflection–Fourier transform infrared spectroscopy (ATR-FTIR), carbon-13 nuclear magnetic resonance (13C NMR), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), Brunauer–Emmett–Teller (BET) method and stereoscopic microscopy. The optimal pH was 8 and the equilibrium time was 120 min. At 30 °C, the adsorption capacity was enhanced (10.8, 19.7, and 25.8 mg g− 1) when the initial concentration of paraquat was increased (25, 50 and 200 mg L− 1, respectively). Adsorption kinetics was described by the pseudo-second-order model and adsorption isotherm was appropriated to the Langmuir model. The negative standard enthalpy change (∆Hº) showed an exothermic process, the positive standard entropy change (∆Sº) displayed an increased disorder and the negative standard Gibbs free energy change (∆Gº) indicated a spontaneous adsorption method. Ultimately, the regeneration efficiency of polymer in methanol was 87.3% after four cycles. This polymer could be used as a potential adsorbent for removal of other cationic pesticides.

Keywords

Insoluble cyclodextrin polymer 1,2,3,4-Butanetetracarboxylic acid Paraquat Adsorption Water contamination 

Notes

Acknowledgements

The authors would like to thank technical staffs for kindly support to achieve experiments. This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

References

  1. 1.
    Liu G, Li L, Huang X, Zheng S, Xu X, Liu Z, Zhang Y, Wang J, Lin H, Xu D (2018) Adsorption and removal of organophosphorus pesticides from environmental water and soil samples by using magnetic multi-walled carbon nanotubes organic framework ZIF-8. J Mater Sci 53:10772–10783CrossRefGoogle Scholar
  2. 2.
    Wei M, Yan X, Liu S, Liu Y (2018) Preparation and evaluation of superparamagnetic core–shell dummy molecularly imprinted polymer for recognition and extraction of organophosphorus pesticide. J Mater Sci 53:4897–4912CrossRefGoogle Scholar
  3. 3.
    Nanseu-Njiki CP, Dedzo GK, Ngameni E (2010) Study of the removal of paraquat from aqueous solution by biosorption onto Ayous (Triplochiton schleroxylon) sawdust. J Hazard Mater 179:63–71CrossRefGoogle Scholar
  4. 4.
    Mhammedi MAE, Bakasse M, Chtaini A (2007) Electrochemical studies and square wave voltammetry of paraquat at natural phosphate modified carbon paste electrode. J Hazard Mater 145:1–7CrossRefGoogle Scholar
  5. 5.
    Recena MCP, Caldas ED, Pires DX, Pontes ERJC (2006) Pesticides exposure in Culturama, Brazil–Knowledge, attitudes, and practices. Environ Res 102:230–236CrossRefGoogle Scholar
  6. 6.
    Núñez O, Kim JB, Moyano E, Galceran MT, Terabe S (2002) Analysis of the herbicides paraquat, diquat and difenzoquat in drinking water by micellar electrokinetic chromatography using sweeping and cation selective exhaustive injection. J Chromatogr A 961:65–75CrossRefGoogle Scholar
  7. 7.
    Dinis-Oliveira RJ, Duarte JA, Sánchez-Navarro A, Remião F, Bastos ML, Carvalho F (2008) Paraquat poisonings: mechanisms of lung toxicity, clinical features, and treatment. Crit Rev Toxicol 38:13–71CrossRefGoogle Scholar
  8. 8.
    Brown R, Clapp M, Dyson J, Scott D, Wheals I, Wilks M (2004) Paraquat in perspective. Outlooks Pest Manag 15:259–267CrossRefGoogle Scholar
  9. 9.
    Smeyne RJ, Breckenridge CB, Beck M, Jiao Y, Butt MT, Wolf JC, Zadory D, Minnema DJ, Sturgess NC, Travis KZ, Cook AR, Smith LL, Botham PA (2016) Assessment of the effects of MPTP and paraquat on dopaminergic neurons and microglia in the substantia nigra pars compacta of C57BL/6 mice. PLoS One 11:e0164094CrossRefGoogle Scholar
  10. 10.
    Lacerda ACR, Rodrigues-Machado M, da G, Mendes, Novaes PL, Carvalho RD, Zin GMC, Gripp WA, Coimbra F CC (2009) Paraquat (PQ)-induced pulmonary fibrosis increases exercise metabolic cost, reducing aerobic performance in rats. J Toxicol Sci 34:671–679CrossRefGoogle Scholar
  11. 11.
    Cho IK, Jeong M, You AS, Park KH, Li QX (2015) Pulmonary proteome and protein networks in response to the herbicide paraquat in rats. J Proteom Bioinform 8:067–079Google Scholar
  12. 12.
    Zhang X, Thompson M, Xu Y (2016) Multifactorial theory applied to the neurotoxicity of paraquat and paraquat-induced mechanisms of developing Parkinson’s disease. Lab Invest 96:496–507CrossRefGoogle Scholar
  13. 13.
    Dinis-Oliveira RJ, Remião F, Carmo H, Duarte JA, Navarro AS, Bastos ML, Carvalho F (2006) Paraquat exposure as an etiological factor of Parkinson’s disease. NeuroToxicol 27:1110–1122CrossRefGoogle Scholar
  14. 14.
    Akhtar M, Hasany SM, Bhanger MI, Iqbal S (2007) Low cost sorbents for the removal of methyl parathion pesticide from aqueous solutions. Chemosphere 66:1829–1838CrossRefGoogle Scholar
  15. 15.
    Carr RJ, Bilton RF, Atkinson T (1985) Mechanism of biodegradation of paraquat by Lipomyces starkeyi. Appl Environ Microbiol 49:1920–1924Google Scholar
  16. 16.
    Santos MSF, Schaule G, Alves A, Madeira LM (2013) Adsorption of paraquat herbicide on deposits from drinking water networks. Chem Eng J 229:324–333CrossRefGoogle Scholar
  17. 17.
    Burns IG, Hayes MHB, Stacey M (1973) Studies of the adsorption of paraquat on soluble humic fractions by gel filtration and ultrafiltration techniques. Pestic Sci 4:629–641CrossRefGoogle Scholar
  18. 18.
    Cocenza DS, de Moraes MA, Beppu MM, Fraceto LF (2012) Use of biopolymeric membranes for adsorption of paraquat herbicide from water. Water Air Soil Pollut 223:3093–3104CrossRefGoogle Scholar
  19. 19.
    Leite MP, dos Reis LGT, Robaina NF, Pacheco WF, Cassella RJ (2013) Adsorption of paraquat from aqueous medium by Amberlite XAD-2 and XAD-4 resins using dodecylsulfate as counter ion. Chem Eng J 215–216:691–698CrossRefGoogle Scholar
  20. 20.
    Humbert H, Gallard H, Suty H, Croué JP (2008) Natural organic matter (NOM) and pesticides removal using a combination of ion exchange resin and powdered activated carbon (PAC). Water Res 42:1635–1643CrossRefGoogle Scholar
  21. 21.
    Cantavenera MJ, Catanzaro I, Loddo V, Palmisano L, Sciandrello G (2007) Photocatalytic degradation of paraquat and genotoxicity of its intermediate products. J Photochem Photobiol Chem 185:277–282CrossRefGoogle Scholar
  22. 22.
    Sorolla MG, Dalida ML, Khemthong P, Grisdanurak N (2012) Photocatalytic degradation of paraquat using nano-sized Cu–TiO2/SBA-15 under UV and visible light. J Environ Sci 24:1125–1132CrossRefGoogle Scholar
  23. 23.
    Zayats MF, Leschev SM, Petrashkevich NV, Zayats MA, Kadenczki L, Szitás R, Dobrik HS, Keresztény N (2013) Distribution of pesticides in n-hexane/water and n-hexane/acetonitrile systems and estimation of possibilities of their extraction isolation and preconcentration from various matrices. Anal Chim Acta 774:33–43CrossRefGoogle Scholar
  24. 24.
    Dhaouadi A, Adhoum N (2009) Degradation of paraquat herbicide by electrochemical advanced oxidation methods. J Electroanal Chem 637:33–42CrossRefGoogle Scholar
  25. 25.
    Santos MSF, Alves A, Madeira LM (2011) Paraquat removal from water by oxidation with Fenton’s reagent. Chem Eng J 175:279–290CrossRefGoogle Scholar
  26. 26.
    Dhaouadi A, Adhoum N (2010) Heterogeneous catalytic wet peroxide oxidation of paraquat in the presence of modified activated carbon. Appl Catal B Environ 97:227–235CrossRefGoogle Scholar
  27. 27.
    Lan S, Zhan S, Ding J, Ma J, Ma D (2017) Pillar[n]arene-based porous polymers for rapid pollutant removal from water. J Mater Chem A 5:2514–2518CrossRefGoogle Scholar
  28. 28.
    Tsai WT, Chen HR (2013) Adsorption kinetics of herbicide paraquat in aqueous solution onto a low-cost adsorbent, swine-manure-derived biochar. Int J Environ Sci Technol 10:1349–1356CrossRefGoogle Scholar
  29. 29.
    Hamadi NK, Swaminathan S, Chen XD (2004) Adsorption of paraquat dichloride from aqueous solution by activated carbon derived from used tires. J Hazard Mater 112:133–141CrossRefGoogle Scholar
  30. 30.
    Nakamura T, Kawasaki N, Ogawa H, Tanada S, Kogirima M, Imaki M (1999) Adsorption removal of paraquat and diquat onto activated carbon at different adsorption temperature. Toxicol Environ Chem 70:275–280CrossRefGoogle Scholar
  31. 31.
    Tsai WT, Lai CW, Hsien KJ (2004) Adsorption kinetics of herbicide paraquat from aqueous solution onto activated bleaching earth. Chemosphere 55:829–837CrossRefGoogle Scholar
  32. 32.
    Iglesias A, López R, Gondar D, Antelo J, Fiol S, Arce F (2010) Adsorption of paraquat on goethite and humic acid-coated goethite. J Hazard Mater 183:664–668CrossRefGoogle Scholar
  33. 33.
    Brigante M, Zanini G, Avena M (2010) Effect of humic acids on the adsorption of paraquat by goethite. J Hazard Mater 184:241–247CrossRefGoogle Scholar
  34. 34.
    Ait Sidhoum D, Socías-Viciana MM, Ureña-Amate MD, Derdour A, González-Pradas E, Debbagh-Boutarbouch N (2013) Removal of paraquat from water by an Algerian bentonite. Appl Clay Sci 83–84:441–448CrossRefGoogle Scholar
  35. 35.
    Hao Y, Wang Z, Gou J, Wang Z (2015) Kinetics and thermodynamics of diquat removal from water using magnetic graphene oxide nanocomposite. Can J Chem Eng 93:1713–1720CrossRefGoogle Scholar
  36. 36.
    Fernandes T, Soares SF, Trindade T, Daniel-da-Silva AL (2017) Magnetic hybrid nanosorbents for the uptake of paraquat from water. Nanomaterials 7:68CrossRefGoogle Scholar
  37. 37.
    Rongchapo W, Keawkumay C, Osakoo N, Deekamwong K, Chanlek N, Prayoonpokarach S, Wittayakun J (2017) Comprehension of paraquat adsorption on faujasite zeolite X and Y in sodium form. Adsorpt Sci Technol 36:684–693CrossRefGoogle Scholar
  38. 38.
    Morin-Crini N, Crini G (2013) Environmental applications of water-insoluble β-cyclodextrin–epichlorohydrin polymers. Prog Polym Sci 38:344–368CrossRefGoogle Scholar
  39. 39.
    Leudjo Taka A, Pillay K, Yangkou Mbianda X (2017) Nanosponge cyclodextrin polyurethanes and their modification with nanomaterials for the removal of pollutants from waste water: a review. Carbohydr Polym 159:94–107CrossRefGoogle Scholar
  40. 40.
    Shirsath N, Raghuvanshi D, Patil C, Gite V, Meshram J (2018) Biocomposite formation using β-cyclodextrin as a biomaterial in poly(acrylamide-co-acrylic acid): preparation, characterization, and salinity profile. Iran Polym J 27:217–224CrossRefGoogle Scholar
  41. 41.
    He C, Zhou Q, Duan Z, Xu X, Wang F, Li H (2018) One-step synthesis of a β-cyclodextrin derivative and its performance for the removal of Pb(II) from aqueous solutions. Res Chem Intermed 44:2983–2998CrossRefGoogle Scholar
  42. 42.
    Mahlambi MM, Malefetse TJ, Mamba BB, Krause RW (2010) β-cyclodextrin-ionic liquid polyurethanes for the removal of organic pollutants and heavy metals from water: synthesis and characterization. J Polym Res 17:589–600CrossRefGoogle Scholar
  43. 43.
    Chen S, Guo H, Yang F, Di X (2016) Cyclodextrin-grafted thiacalix [4]arene netty polymer based on the click chemistry: preparation and efficient adsorption for organic dyes. J Polym Res 23:28CrossRefGoogle Scholar
  44. 44.
    Ye H, Zhang X, Zhao Z, Song B, Zhang Z, Song W (2017) Pervaporation performance of surface-modified zeolite/PU mixed matrix membranes for separation of phenol from water. Iran Polym J 26:193–203CrossRefGoogle Scholar
  45. 45.
    Shang S, Chiu KL, Jiang S (2017) Synthesis of immobilized poly(vinyl alcohol)/cyclodextrin eco-adsorbent and its application for the removal of ibuprofen from pharmaceutical sewage. J Appl Polym Sci 134:44861Google Scholar
  46. 46.
    Liu H, Cai X, Wang Y, Chen J (2011) Adsorption mechanism-based screening of cyclodextrin polymers for adsorption and separation of pesticides from water. Water Res 45:3499–3511CrossRefGoogle Scholar
  47. 47.
    Garrido EM, Rodrigues D, Milhazes N, Borges F, Garrido J (2017) Molecular encapsulation of herbicide terbuthylazine in native and modified β-cyclodextrin. J Chem 2017:1–9CrossRefGoogle Scholar
  48. 48.
    Kalia S, Kango S, Kumar A, Haldorai Y, Kumari B, Kumar R (2014) Magnetic polymer nanocomposites for environmental and biomedical applications. Colloid Polym Sci 292:2025–2052CrossRefGoogle Scholar
  49. 49.
    Celebioglu A, Yildiz ZI, Uyar T (2017) Electrospun crosslinked poly-cyclodextrin nanofibers: highly efficient molecular filtration thru host-guest inclusion complexation. Sci Rep 7:7369CrossRefGoogle Scholar
  50. 50.
    Martel B, Ruffin D, Weltrowski M, Lekchiri Y, Morcellet M (2005) Water-soluble polymers and gels from the polycondensation between cyclodextrins and poly(carboxylic acid)s: a study of the preparation parameters. J Appl Polym Sci 97:433–442CrossRefGoogle Scholar
  51. 51.
    Ducoroy L, Martel B, Bacquet M, Morcellet M (2007) Ion exchange textiles from the finishing of PET fabrics with cyclodextrins and citric acid for the sorption of metallic cations in water. J Incl Phenom Macrocycl Chem 57:271–277CrossRefGoogle Scholar
  52. 52.
    Euvrard É, Morin-sCrini N, Druart C, Bugnet J, Martel B, Cosentino C, Moutarlier V, Crini G (2016) Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters. Beilstein J Org Chem 12:1826–1838CrossRefGoogle Scholar
  53. 53.
    Tsai WT, Hsien KJ, Chang YM, Lo CC (2005) Removal of herbicide paraquat from an aqueous solution by adsorption onto spent and treated diatomaceous earth. Bioresour Technol 96:657–663CrossRefGoogle Scholar
  54. 54.
    Brigante M, Schulz PC (2011) Adsorption of paraquat on mesoporous silica modified with titania: effects of pH, ionic strength and temperature. J Colloid Interface Sci 363:355–361CrossRefGoogle Scholar
  55. 55.
    Draoui K, Denoyel R, Chgoura M, Rouquerol J (1999) Adsorption of paraquat on minerals: a thermodynamic study. J Therm Anal Calorim 58:597–606CrossRefGoogle Scholar
  56. 56.
    Zhao F, Repo E, Yin D, Meng Y, Jafari S, Sillanpää M (2015) EDTA-cross-linked β-cyclodextrin: an environmentally friendly bifunctional adsorbent for simultaneous adsorption of metals and cationic dyes. Environ Sci Technol 49:10570–10580CrossRefGoogle Scholar

Copyright information

© Iran Polymer and Petrochemical Institute 2019

Authors and Affiliations

  1. 1.Faculty of Science and TechnologyNakhon Ratchasima Rajabhat UniversityNakhon RatchasimaThailand
  2. 2.The Petroleum and Petrochemical CollegeChulalongkorn UniversityBangkokThailand
  3. 3.School of PhysicsSuranaree University of TechnologyNakhon RatchasimaThailand

Personalised recommendations