A green and simple method for preparation of an efficient palladium adsorbent based on cysteine functionalized 2,3-dialdehyde cellulose

Cellulose

Volumn 23, Issue 4, 2016, Pages 2627-2638

  Ruan, Changqing ^a   Strømme, Maria ^a   Lindh, Jonas ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

2,3 dialdehyde cellulose; Cellulose beads; Nanocellulose; Palladium adsorption

Indexed keywords

ADSORPTION; ALGAE; AMINES; AMINO ACIDS; CELLULOSE; IONS; PALLADIUM COMPOUNDS;

2 ,3-DIALDEHYDE CELLULOSE; ADSORBENT MATERIALS; ADSORPTION PROPERTIES; CELLULOSE BEADS; DEGREE OF OXIDATIONS; HIGH ADSORPTION CAPACITY; NANO-CELLULOSE; REDUCTIVE AMINATION;

GAS ADSORPTION;

AMINATION; CELLULOSE DERIVATIVES; CYSTEINE; OXIDATION; PALLADIUM;

EID: 84978895686     PISSN: 09690239     EISSN: 1572882X     Source Type: Journal    
DOI: 10.1007/s10570-016-0976-0     Document Type: Article

References (50)

1. Anpilogova GR, Bondareva SO, Khisamutdinov RA, Murinov YI (2014) Fatty imidazolines: a novel extractant for the recovery of palladium(ii) from hydrochloric acid solutions. Solv Extr Ion Exch 32:206–220. doi:10.1080/07366299.2013.838498
2. Awual MR, Yaita T, El-Safty SA, Shiwaku H, Okamoto Y, Suzuki S (2013) Investigation of palladium(II) detection and recovery using ligand modified conjugate adsorbent. Chem Eng J 222:172–179. doi:10.1016/j.cej.2013.02.058
3. Barakat MA, Mahmoud MHH, Mahrous YS (2006) Recovery and separation of palladium from spent catalyst. Appl Catal A 301:182–186. doi:10.1016/j.apcata.2005.11.028
4. Brunauer S, Emmett PH, Teller E (1938) Adsorption of gases in multimolecular layers. J Am Chem Soc 60:309–319. doi:10.1021/ja01269a023
5. Bruneel D, Schacht E (1993) Chemical modification of pullulan: 1. Periodate oxidation. Polymer 34:2628–2632. doi:10.1016/0032-3861(93)90600-F
6. Carlsson DO, Lindh J, Nyholm L, Strømme M, Mihranyan A (2014) Cooxidant-free TEMPO-mediated oxidation of highly crystalline nanocellulose in water. Rsc Advances 4:52289–52298. doi:10.1039/c4ra11182f
7. β-dominated cellulose to tempo-mediated oxidation. Biomacromolecules 16:1643–1649. doi:10.1021/acs.biomac.5b00274
8. Casu B, Naggi A, Torri G, Allegra G, Meille SV, Cosani A, Terbojevich M (1985) Stereoregular acyclic polyalcohols and polyacetates from cellulose and amylose. Macromolecules 18:2762–2767. doi:10.1021/ma00154a068
9. Cosenza VA, Navarro DA, Stortz CA (2011) Usage of alpha-picoline borane for the reductive amination of carbohydrates. Org Chem Argent 2011:182–194. doi:10.3998/ark.5550190.0012.716
10. Freundlich HMA (1906) Concerning adsorption in solutions. J Phys Chem 57:385–470
11. Fujiwara K, Ramesh A, Maki T, Hasegawa H, Ueda K (2007) Adsorption of platinum (IV), palladium (II) and gold (III) from aqueous solutions onto l-lysine modified crosslinked chitosan resin. J Hazard Mater 146:39–50. doi:10.1016/j.jhazmat.2006.11.049
12. Gericke M, Trygg J, Fardim P (2013) Functional cellulose beads: preparation, characterization, and applications. Chem Rev 113:4812–4836. doi:10.1021/cr300242j
13. Gupta VK, Jain CK, Ali I, Sharma M, Saini VK (2003) Removal of cadmium and nickel from wastewater using bagasse fly ash—a sugar industry waste. W Res 37:4038–4044. doi:10.1016/S0043-1354(03)00292-6
14. Gupta VK, Mittal A, Gajbe V, Mittal J (2006) Removal and recovery of the hazardous azo dye acid orange 7 through adsorption over waste materials: bottom ash and de-oiled soya. Ind Eng Chem Res 45:1446–1453. doi:10.1021/ie051111f
15. Jermakowicz-Bartkowiak D, Kolarz BN, Serwin A (2005) Sorption of precious metals from acid solutions by functionalised vinylbenzyl chloride–acrylonitryle–divinylbenzene copolymers bearing amino and guanidine ligands. React Funct Polym 65:135–142. doi:10.1016/j.reactfunctpolym.2004.11.010
16. Kitkulnumchai Y, Ajavakom A, Sukwattanasinitt M (2008) Treatment of oxidized cellulose fabric with chitosan and its surface activity towards anionic reactive dyes. Cellulose 15:599–608. doi:10.1007/s10570-008-9214-8
17. Klemm D, Heublein B, Fink HP, Bohn A (2005) Cellulose: fascinating biopolymer and sustainable raw material. Angew Chem-Int Edit 44:3358–3393. doi:10.1002/anie.200460587
18. Lagergren S (1898) Kungliga Svenska Vetenskapsakademiens, vol 24. Vetensk, Handl
19. Langmuir I (1918) The adsorption of gases on plane surfaces of glass, mica and platinum. J Am Chem Soc 40:1361–1403. doi:10.1021/ja02242a004
20. Li GQ, Konishi S, Saito K, Sugo T (1994) High collection rate of Pd in hydrochloric-acid medium using chelating microporous membrane. J Membr Sci 95:63–69. doi:10.1016/0376-7388(94)85029-1
21. Lim JS, Kim SM, Lee SY, Stach EA, Culver JN, Harris MT (2011) Surface functionalized silica as a toolkit for studying aqueous phase palladium adsorption and mineralization on thiol moiety in the absence of external reducing agents. J Coll Interf Sci 356:31–36. doi:10.1016/j.jcis.2010.12.064
22. Lindh J, Carlsson DO, Strømme M, Mihranyan A (2014) Convenient one-pot formation of 2,3-dialdehyde cellulose beads via periodate oxidation of cellulose in water. Biomacromolecules 15:1928–1932. doi:10.1021/bm5002944
23. Lindh J, Ruan C, Strømme M, Mihranyan A (2016) Preparation of porous cellulose beads via introduction of diamine spacers. Langmuir. doi:10.1021/acs.langmuir.6b01288
24. Liu K, Yen W, Shibayama A, Fujita T (2003) Selective leaching of platinum and palladium by chloride solution. In: Proceedings of the TMS Fall Extraction and Processing Conference, pp 1617–1628
25. Maekawa E, Koshijima T (1984) Properties of 2,3-dicarboxy cellulose combined with various metallic ions. J Appl Polym Sci 29:2289–2297. doi:10.1002/app.1984.070290705
26. Metreveli G, Wagberg L, Emmoth E, Belak S, Stromme M, Mihranyan A (2014) A size-exclusion nanocellulose filter paper for virus removal. Adv Healthc Mater 3:1546–1550. doi:10.1002/adhm.201300641
27. Mihranyan A (2011) Cellulose from Cladophorales green algae: from environmental problem to high-tech composite materials. J Appl Polym Sci 119:2449–2460. doi:10.1002/app.32959
28. Moulder JF, Stickle WF, Sobol PE, Bomben KD (1992) Handbook of X-ray photoelectron spectroscopy. Perkin-Elmer Corp, Palo Alto
29. Nada A, Hassan ML (2006) Ion exchange properties of carboxylated bagasse. J Appl Polym Sci 102:1399–1404. doi:10.1002/app.24255
30. Nolan EM, Lippard SJ (2008) Tools and tactics for the optical detection of mercuric ion. Chem Rev 108:3443–3480. doi:10.1021/cr068000q
31. Nyholm L, Nyström G, Mihranyan A, Strømme M (2011) Toward flexible polymer and paper-based energy storage devices. Adv Mater 23:3751–3769. doi:10.1002/adma.201004134
32. Paiva AP, Carvalho GI, Costa MC, da Costa AMR, Nogueira C (2014) Recovery of platinum and palladium from chloride solutions by a thiodiglycolamide derivative. Solv Extr Ion Exch 32:78–94. doi:10.1080/07366299.2013.810969
33. Panchompoo J, Aldous L, Compton RG (2011) Irreversible uptake of palladium from aqueous systems using l-cysteine methyl esterphysisorbed on carbon black. J Mater Chem 21:9513–9522. doi:10.1039/C0JM04493H
34. Products CfPM (17th December, 2002) European agency for the evaluation of medicinal products. Evaluation of Medicines for Human Use, London, UK
35. Qishu Q, Qian G, Zuli G, Yuqi S, Chengyin W, Xiaoya H (2012) Efficient removal of heavy metal from aqueous solution by sulfonic acid functionalized nonporous silica microspheres. Coll Surf Physicochem Eng Asp 415:41–46. doi:10.1016/j.colsurfa.2012.08.059
36. Razaq A, Nyholm L, Sjödin M, Strømme M, Mihranyan A (2012) Paper-based energy-storage devices comprising carbon fiber-reinforced polypyrrole-Cladophora nanocellulose composite electrodes. Adv Energy Mater 2:445–454. doi:10.1002/aenm.201100713
37. Rowen JW, Forziati FH, Reeves RE (1951) Spectrophotometric evidence for the absence of free aldehyde groups in periodate-oxidized cellulose. J Am Chem Soc 73:4484–4487. doi:10.1021/ja01153a535
38. Ruhaak LR, Steenvoorden E, Koeleman CAM, Deelder AM, Wuhrer M (2010) 2-Picoline-borane: a non-toxic reducing agent for oligosaccharide labeling by reductive amination. Proteomics 10:2330–2336. doi:10.1002/pmic.200900804
39. Sabzalian Z, Alam MN, van de Ven TGM (2014) Hydrophobization and characterization of internally crosslink-reinforced cellulose fibers. Cellulose 21:1381–1393. doi:10.1007/s10570-014-0178-6
40. Sağ Y (2001) Biosorption of heavy metals by fungal biomass and modeling of fungal biosorption: a review. Sep Purif Rev 30:1–48. doi:10.1081/SPM-100102984
41. Sato S, Sakamoto T, Miyazawa E, Kikugawa Y (2004) One-pot reductive amination of aldehydes and ketones with alpha-picoline-borane in methanol, in water, and in neat conditions. Tetrahedron 60:7899–7906. doi:10.1016/j.tet.2004.06.045
42. Segal L, Creely J, Martin A, Conrad C (1959) An empirical method for estimating the degree of crystallinity of native cellulose using the X-ray diffractometer. Text Res J 29:786–794
43. Sharma S, Rajesh N (2014) 2-Mercaptobenzothiazole impregnated cellulose prepared by ultrasonication for the effective adsorption of precious metal palladium. Chem Eng J 241:112–121. doi:10.1016/j.cej.2013.12.002
44. Sparks DL (ed) (1986) Kinetics of reactions in pure and in mixed systems. In: Soil physical chemistry. CRC Press, Boca Raton, pp 83–145
45. Spedding H (1960) Infrared spectra of periodate-oxidised cellulose. J Chem Soc 73:3147–3152. doi:10.1039/JR9600003147
46. Su SX, Nutiu R, Filipe CDM, Li YF, Pelton R (2007) Adsorption and covalent coupling of ATP-binding DNA aptamers onto cellulose. Langmuir 23:1300–1302. doi:10.1021/la060961c
47. Takaichi S, Hiraoki R, Inamochi T, Isogai A (2014) One-step preparation of 2,3,6-tricarboxy cellulose. Carbohydr Polym 110:499–504. doi:10.1016/j.carbpol.2014.03.085
48. Venkatesan KA, Selvan BR, Antony MP, Srinivasan TG, Rao PRV (2005) Extraction of palladium from nitric acid medium by commercial resins with phosphinic acid, methylene thiol and isothiouronium moieties attached to polystyrene-divinylbenzene. J Radioanal Nucl Chem 266:431–440. doi:10.1007/s10967-005-0928-x
49. Vincent T, Guibal E, Chiarizia R (2007) Palladium recovery by reactive precipitation using a cyanex 301-based stable emulsion. Sep Sci Technol 42:3517–3536. doi:10.1080/01496390701626735
50. Wasikiewicz JM, Mitomo H, Seko N, Tamada M, Yoshii F (2007) Platinum and palladium ions adsorption at the trace amounts by radiation crosslinked carboxymethylchitin and carboxymethylchitosan hydrogels. J Appl Polym Sci 104:4015–4023. doi:10.1002/app.26034