Magnetic nanoparticles modified by polyamidoamine-immobilized TEMPO for catalytic oxidation of monomethoxy poly (ethylene glycol)
Source abstract
Abstract
Magnetic nanoparticles (MNPs) modified by polyamidoamine (PAMAM)-immobilized 2,2,6,6-tetramethyl-1-piperidinyl-oxyl (TEMPO) as recoverable catalysts for catalytic oxidation of polyethylene glycol were designed and prepared, which were expected to combine the advantages of easy recovery of MNPs and high activity of PAMAM-immobilized TEMPO. The catalysts of MNPs modified by PAMAM-immobilized TEMPO (MNPs-PAMAM-T) were characterized by Fourier transform infrared spectroscopy (FT-IR), thermal gravimetric analyzer (TGA), and transmission electron microscopy (TEM). The mean particle size of MNPs was about 10 nm. MNPs-PAMAM-T/NaBr/NaClO was used as catalytic system for catalytic oxidation of monomethoxy poly (ethylene glycol). The catalytic performances were affected by the loading amounts of TEMPO and PAMAM generations. It was shown that the catalyst with TEMPO loading of 5.198 mmol/g using G2.0 PAMAM-modified MNPs as carrier had the best catalytic performance, which could be up to 94% of the free TEMPO level. The efficient recovery of catalyst could be achieved by magnetic separation and the recycling performance was good.
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Research context
OpenAlex topics: Catalytic Processes in Materials Science · Mesoporous Materials and Catalysis · Nanomaterials for catalytic reactions
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
References (43)
Show source-provided references
1. Araki J, Iida M (2016) Surface carboxylation of cellulose nanowhiskers using mPEG-TEMPO: its recovery and recycling. Polym J 48:1029–103310.1038/pj.2016.65 ↗
2. Araki J, Zhao CM, Ito K (2005) Efficient production of polyrotaxanes from α-cyclodextrin and poly (ethylene glycol). Macromolecules 38:7524–752710.1021/ma050290+ ↗
3. Beejapur HA, Zhang Q, Hu K, Zhu L, Wang J, Ye Z (2019) TEMPO in chemical transformations: from homogeneous to heterogeneous. ACS Catal 9:2777–283010.1021/acscatal.8b05001 ↗
4. Bolm C, Fey T (1999) TEMPO oxidations with a silica-supported catalyst. Chem Commun 18:1795–179610.1039/a905683a ↗
5. Chen P, Chen G, Zhao YQ (2015) A method for preparing terminal carboxylated polyethylene glycol. CN Pat. 104761716 A.
6. Chou CM, Lien HL (2010) Dendrimer-conjugated magnetic nanoparticles for removal of zinc (II) from aqueous solutions. J Nanopart Res 13:2099–210710.1007/s11051-010-9967-5 ↗
7. Christophe M, Daniel S, Michel B (2001) 2,2,6,6-Tetramethyl-1-piperidinyl-oxyl/[Bis (acetoxy)-iodo] benzene-mediated oxidation: a versatile and convenient route to poly (ethylene glycol) aldehyde or carboxylic acid derivatives. J Polym Sci A Polym Chem 39:4022–402410.1002/pola.10049 ↗
8. Cui Y, Zhang J, Yu Q, Guo X, Chen S, Sun H, Liu S, Wang LG, Lai X, Gao D (2019) Highly biocompatible zwitterionic dendrimer-encapsulated platinum nanoparticles for sensitive detection of glucose in complex medium. New J Chem 43:9076–908310.1039/C9NJ01101C ↗
9. Elouarzaki K, Mandoc LRP, Gorgy K, Holzinger M, Amarandei CA, Ungureanu EM, Cosnier S (2015) Synthesis and electrochemical characterization of original “TEMPO” functionalized multiwall carbon nanotube materials: application to iron (II) detection. Electrochem Commun 60:131–13410.1016/j.elecom.2015.08.024 ↗
10. Gao BJ, Zhang LQ, Chen T (2015) TEMPO immobilized on polymer microspheres-catalyzed oxidation of cyclohexanol by molecular oxygen. Chin J Catal 36:1230–123610.1016/S1872-2067(15)60902-0 ↗
11. Guo X, Zhang J, Cui Y, Chen S, Sun H, Yang Q, Ma G, Wang L, Kang J (2019) Highly biocompatible jujube polysaccharide-stabilized palladium nanoparticles with excellent catalytic performance. New J Chem 43:7646–765210.1039/C9NJ00950G ↗
12. Hövelmann CH, Gooβen S, Allgaier J (2017) Scale-up procedure for the efficient synthesis of highly pure cyclic poly (ethylene glycol). Macromolecules 50:4169–417910.1021/acs.macromol.7b00361 ↗
13. Huang J, Chen SF, Zeng T, Li JW (2007) Acid-Base titration applied in characterization of poly (amidoamine). Polym Mater Sci Eng 23:185–191
14. Karimi B, Farhangi E (2013) One−pot oxidative passerini reaction of alcohols using a magnetically recyclable TEMPO under metal− and halogen−free conditions. Adv Synth Catal 355:508–51610.1002/adsc.201200449 ↗
15. Karimi B, Biglari A, Clark JH, Budarin V (2007) Green, transition-metal-free aerobic oxidation of alcohols using a highly durable supported organocatalyst. Angew Chem Int Ed 46:7210–721310.1002/anie.200701918 ↗
16. Khodadust R, Unsoy G, Yalcin S, Gunduz G, Gunduz U (2013) PAMAM dendrimer-coated iron oxide nanoparticles: synthesis and characterization of different generations. J Nanopart Res 15:1488–150110.1007/s11051-013-1488-6 ↗
17. Khorramabadi-zad A, Daliran S, Oveisi AR (2013) Aerial oxidation of bisnaphthols to spironaphthalenones by a recyclable magnetic core-sell nanoparticle-supported TEMPO catalyst. CR Chim 16:972–97610.1016/j.crci.2013.02.002 ↗
18. Kim SY, Ha JC, Lee YM (2000) Poly (ethylene oxide)-poly (propylene oxide)-poly (ethylene oxide)/poly(ϵ-caprolactone)(PCL) amphiphilic block copolymeric nanospheres. J Control Release 65:345–35810.1016/S0168-3659(99)00207-2 ↗
19. Lewis LN (1993) Chemical catalysis by colloids and clusters. Chem Rev 93:2693–273010.1021/cr00024a006 ↗
20. Liu SJ, Hu QQ, Zhao FQ, Tang EJ (2014) Nitroxide polymer brushes prepared by surface-initiated ARGET ATRP and their selective oxidation performances. Express Polym Lett 8:862–86810.3144/expresspolymlett.2014.87 ↗
21. Liu SJ, Chu XM, Wang HL, Zhao FQ, Tang EJ (2015) Preparation of nitroxide polymer brushes and their applications in the synthesis of an epoxidized soybean oil acrylate as an inhibitor. Ind Eng Chem Res 54:5475–548010.1021/acs.iecr.5b00824 ↗
22. Liu SJ, Xing YB, Han JZ, Tang EJ (2017) Catalytic oxidation of cellulose with a novel amphiphilic nitroxide block copolymer as a recoverable catalyst. Cellulose 24:3635–364410.1007/s10570-017-1375-x ↗
23. Liu SJ, Liang HZ, Sun TT, Yang DS, Cao M (2018a) A recoverable dendritic polyamidoamine immobilized TEMPO for efficient catalytic oxidation of cellulose. Carbohydr Polym 202:563–57010.1016/j.carbpol.2018.09.016 ↗
24. Liu SJ, Sun TT, Yang DS, Cao M, Liang HZ (2018b) Polyacrylic acid supported TEMPO for selective catalytic oxidation of cellulose: recovered by its pH sensitivity. Cellulose 25:5687–569610.1007/s10570-018-2012-z ↗
25. Lv WQ, Geng C, Xu JW (2019) Ozonation of polyethylene glycol aldehyde derivatives. Chin J Appl Chem 36:120–122
26. Megiel E (2017) Surface modification using TEMPO and its derivatives. Adv Colloid Interface Sci 250:158–18410.1016/j.cis.2017.08.008 ↗
27. Pan BF, Gao F, Gu HC (2005) Dendrimer modified magnetite nanoparticles for protein immobilization. J Colloid Interface Sci 284:1–610.1016/j.jcis.2004.09.073 ↗
28. Patankar SC, Renneckar S (2017) Greener synthesis of nanofibrillated cellulose using magnetically separable TEMPO nanocatalyst. Green Chem 19:4792–479710.1039/C7GC02383A ↗
29. Schatz A, Grass RN, Stark WJ, Reiser O (2008) TEMPO supported on magnetic C/Co−nanoparticles: a highly active and recyclable organocatalyst. Chem – Eur J 14: 8262−826610.1002/chem.200801001 ↗
30. Shakir AJ, Paraschivescu C, Matache M, Tudose M, Mischie A, Spafiu F, Ionita P (2015) A convenient alternative for the selective oxidation of alcohols by silica supported TEMPO using dioxygen as the final oxidant. Tetrahedron Lett 56:6878–688110.1016/j.tetlet.2015.10.099 ↗
31. Shylesh S, Schunemann V, Thiel WR (2010) Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis. Angew Chem Int Ed 49:3428–345910.1002/anie.200905684 ↗
32. Subhani MA, Beigi M, Eilbracht P (2008) Polyurethane-and polystyrene-supported 2,2,6,6-tetramethyl-piperidine-1-oxyl (TEMPO): facile preparation, catalytic oxidation and application in a membrane reactor. Adv Synth Catal 350:2903–290910.1002/adsc.200800369 ↗
33. Tang J, Zhang Q, Hu K, Zhang P, Wang J (2017) Novel high TEMPO loading magneto-polymeric nanohybrids: an efficient and recyclable Pickering interfacial catalyst. J Catal 353:192–19810.1016/j.jcat.2017.07.020 ↗
34. Tucker-Schwartz AK, Garrell RL (2010) Simple preparation and application of TEMPO-coated Fe3O4 superparamagnetic nanoparticles for selective oxidation of alcohols. Chem Eur J 16:12718–1272610.1002/chem.200903527 ↗
35. Veronese FM (2001) Peptide and protein PEGylation: a review of problems and solutions. Biomaterials 22:405–41710.1016/S0142-9612(00)00193-9 ↗
36. Wan C, Chung Y, Toy PH (2007) Multipolymer reaction system for selective aerobic alcohol oxidation: simultaneous use of multiple different polymer-supported ligands. J Comb Chem 9:115–12010.1021/cc060111f ↗
37. Wang YM, Song XY, Shao SH, Zhong HM, Lin F (2012) An efficient, soluble, and recyclable multiwalled carbon nanotubes-supported TEMPO for oxidation of alcohols. RSC Adv 2:7693–769810.1039/c2ra21206d ↗
38. Wang LY, Li J, Zhao XP, Lv Y, Zhang HY, Gao S (2013) An efficient and scalable room temperature aerobic alcohol oxidation catalyzed by iron chloride hexahydrate/mesoporous silica supported TEMPO. Tetrahedron 69:6041–604510.1016/j.tet.2013.05.076 ↗
39. Yang C, Guenzi M, Cicogna F, Gambarotti C, Filippone G, Pinzino C, Passaglia E, Dintcheva NT, Carroccio S, Coiai S (2016) Grafting of polymer chains on the surface of carbon nanotubes via nitroxide radical coupling reaction. Polym Int 65:48–5610.1002/pi.5023 ↗
40. Yu YL, Gao BJ, Li YF (2014) Immobilized 2,2,6,6-tetramethyl-piperidinyl-1-oxy catalyst on polymer microspheres and its catalytic oxidation of benzyl alcohol with molecular oxygen. Chin J Catal 34:1776–178610.1016/S1872-2067(12)60651-2 ↗
41. Zhao HL, Zhang ZG, Zhao ZJ, Yu RH, Wan YY, Lan MB (2012) Preparation and characterization of novel spin labeled magnetic nanoparticles. Adv Mater Lett 2:172–17510.5185/amlett.2011.1210 ↗
42. Zheng Z, Wang J, Zhang M, Xu L, Ji J (2013) Magnetic polystyrene nanosphere immobilized TEMPO: a readily prepared, highly reactive and recyclable polymer catalyst in the selective oxidation of alcohols. ChemCatChem 5:307–31210.1002/cctc.201200459 ↗
43. Zhu J, Wang PC, Lu M (2012) Synthesis of novel magnetic silica supported hybrid ionic liquid combining TEMPO and polyoxometalate and its application for selective oxidation of alcohols. RSC Adv 2:8265–826810.1039/c2ra20588b ↗