Visualizing Nanocatalysts in Action from Color Change Reaction to Magnetic Recycling and Reuse

Journal of Chemical Education

Volumn 92, Issue 11, 2015, Pages 1892-1895

  Hudson, Reuben ^a   Bishop, Alexandra ^a,b   Glaisher, Samuel ^a,b   Katz, Jeffrey L ^a  

^a Health Services and Department of Biology   (United States)

^b Beyond Benign Foundation   (United States)

Author keywords

Catalysis; Demonstrations; First Year Undergraduate General; Green Chemistry; Inorganic Chemistry; Organic Chemistry; Public Understanding Outreach; Upper Division Undergraduate

Indexed keywords

EID: 84946924437     PISSN: 00219584     EISSN: 19381328     Source Type: Journal    
DOI: 10.1021/acs.jchemed.5b00106     Document Type: Article

References (43)

1. Shakhashiri, B. Z.; Dirreen, G. E.; Williams, L. G. Paramagnetism and color of liquid oxygen: A lecture demonstration J. Chem. Educ. 1980, 57 (5) 373 10.1021/ed057p373
2. Abu-Reziq, R.; Alper, H.; Wang, D.; Post, M. L. Metal supported on dendronized magnetic nanoparticles: highly selective hydroformylation catalysts J. Am. Chem. Soc. 2006, 128 (15) 5279-5282 10.1021/ja060140u
3. Lu, A. H.; Salabas, E. e. L.; Schüth, F. Magnetic nanoparticles: synthesis, protection, functionalization, and application Angew. Chem., Int. Ed. 2007, 46 (8) 1222-1244 10.1002/anie.200602866
4. Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Magnetically recoverable nanocatalysts Chem. Rev. 2011, 111 (5) 3036-3075 10.1021/cr100230z
5. Hudson, R.; Feng, Y.; Varma, R. S.; Moores, A. Bare magnetic nanoparticles: sustainable synthesis and applications in catalytic organic transformations Green Chem. 2014, 16 (10) 4493-4505 10.1039/C4GC00418C
6. Furlan, P. Y.; Melcer, M. E. Removal of Aromatic Pollutant Surrogate from Water by Recyclable Magnetite-Activated Carbon Nanocomposite: An Experiment for General Chemistry J. Chem. Educ. 2014, 91 (11) 1966-1970 10.1021/ed500246s
7. Andraos, J.; Dicks, A. P. Green chemistry teaching in higher education: a review of effective practices Chem. Educ. Res. Pract. 2012, 13 (2) 69-79 10.1039/C1RP90065J
8. Stacey, J. M.; Dicks, A. P.; Goodwin, A. A.; Rush, B. M.; Nigam, M. Green Carbonyl Condensation Reactions Demonstrating Solvent and Organocatalyst Recyclability J. Chem. Educ. 2013, 90 (8) 1067-1070 10.1021/ed300819r
9. Simeonov, S. P.; Afonso, C. A. M. Batch and Flow Synthesis of 5-Hydroxymethylfurfural (HMF) from Fructose as a Bioplatform Intermediate: An Experiment for the Organic or Analytical Laboratory J. Chem. Educ. 2013, 90 (10) 1373-1375 10.1021/ed300780h
10. Reed, S. M.; Hutchison, J. E. Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid J. Chem. Educ. 2000, 77 (12) 1627 10.1021/ed077p1627
11. Crumbie, R. L. Environmentally Responsible Redox Chemistry: An Example of Convenient Oxidation Methodology without Chromium Waste J. Chem. Educ. 2006, 83 (2) 268 10.1021/ed083p268
12. Ragsdale, R. O.; Vanderhooft, J. C.; Zipp, A. P. Small-Scale Kinetic Study of the Catalyzed Decomposition of Hydrogen Peroxide J. Chem. Educ. 1998, 75 (2) 215 10.1021/ed075p215
13. Abad, A.; Corma, A.; García, H. Bridging the gap between homogeneous and heterogeneous gold catalysis: supported gold nanoparticles as heterogeneous catalysts for the benzannulation reaction Top. Catal. 2007, 44 (1-2) 237-243 10.1007/s11244-007-0296-6
14. Roduner, E. Size matters: why nanomaterials are different Chem. Soc. Rev. 2006, 35 (7) 583-592 10.1039/b502142c
15. Wang, D.; Astruc, D. Fast-Growing Field of Magnetically Recyclable Nanocatalysts Chem. Rev. 2014, 114, 6949 10.1021/cr500134h
16. Gawande, M. B.; Branco, P. S.; Varma, R. S. Nano-magnetite (Fe 3 O 4) as a support for recyclable catalysts in the development of sustainable methodologies Chem. Soc. Rev. 2013, 42 (8) 3371-3393 10.1039/c3cs35480f
17. Zeng, T.; Yang, L.; Hudson, R.; Song, G.; Moores, A. R.; Li, C.-J. Fe3O4 Nanoparticle-Supported Copper(I) Pybox Catalyst: Magnetically Recoverable Catalyst for Enantioselective Direct-Addition of Terminal Alkynes to Imines Org. Lett. 2011, 13 (3) 442-445 10.1021/ol102759w
18. Hudson, R.; Li, C.-J.; Moores, A. Magnetic copper-iron nanoparticles as simple heterogeneous catalysts for the azide-alkyne click reaction in water Green Chem. 2012, 14 (3) 622-624 10.1039/c2gc16421c
19. Ishikawa, S.; Hudson, R.; Masnadi, M.; Bateman, M.; Castonguay, A.; Braidy, N.; Moores, A.; Li, C.-J. Cyclopropanation of diazoesters with styrene derivatives catalyzed by magnetically recoverable copper-plated iron nanoparticles Tetrahedron 2014, 70 (36) 6162-6168 10.1016/j.tet.2014.03.090
20. Zhou, S.; Johnson, M.; Veinot, J. G. C. Iron/iron oxide nanoparticles: a versatile support for catalytic metals and their application in Suzuki-Miyaura cross-coupling reactions Chem. Commun. 2010, 46 (14) 2411-2413 10.1039/b922462a
21. Hudson, R.; Chazelle, V.; Bateman, M.; Roy, R.; Li, C.-J.; Moores, A. Sustainable Synthesis of Magnetic Ruthenium-Coated Iron Nanoparticles and Application in the Catalytic Transfer Hydrogenation of Ketones ACS Sustainable Chem. Eng. 2015, 3, 814 10.1021/acssuschemeng.5b00206
22. Kelsen, V.; Wendt, B.; Werkmeister, S.; Junge, K.; Beller, M.; Chaudret, B. The use of ultrasmall iron(0) nanoparticles as catalysts for the selective hydrogenation of unsaturated C-C bonds Chem. Commun. 2013, 49 (33) 3416-3418 10.1039/c3cc00152k
23. Hudson, R.; Hamasaka, G.; Osako, T.; Yamada, Y. M. A.; Li, C.-J.; Uozumi, Y.; Moores, A. Highly efficient iron(0) nanoparticle-catalyzed hydrogenation in water in flow Green Chem. 2013, 15 (8) 2141-2148 10.1039/c3gc40789f
24. Hudson, R.; Riviere, A.; Cirtiu, C. M.; Luska, K. L.; Moores, A. Iron-iron oxide core-shell nanoparticles are active and magnetically recyclable olefin and alkyne hydrogenation catalysts in protic and aqueous media Chem. Commun. 2012, 48 (27) 3360-3362 10.1039/c2cc16438h
25. Bedford, R. B.; Betham, M.; Bruce, D. W.; Davis, S. A.; Frost, R. M.; Hird, M. Iron nanoparticles in the coupling of alkyl halides with aryl Grignard reagents Chem. Commun. 2006, 13) 1398-1400 10.1039/b601014h
26. Sonnenberg, J. F.; Morris, R. H. Evidence for Iron Nanoparticles Catalyzing the Rapid Dehydrogenation of Ammonia-Borane ACS Catal. 2013, 3 (6) 1092-1102 10.1021/cs400115p
27. Shi, F.; Tse, M. K.; Pohl, M. M.; Brückner, A.; Zhang, S.; Beller, M. Tuning Catalytic Activity between Homogeneous and Heterogeneous Catalysis: Improved Activity and Selectivity of Free Nano-Fe2O3 in Selective Oxidations Angew. Chem., Int. Ed. 2007, 46 (46) 8866-8868 10.1002/anie.200703418
28. Rak, M. J.; Lerro, M.; Moores, A. Hollow iron oxide nanoshells are active and selective catalysts for the partial oxidation of styrene with molecular oxygen Chem. Commun. 2014, 50 (83) 12482-12485 10.1039/C4CC04749D
29. 3-H Bonds Using Molecular Oxygen Synlett 2010, 2010 (13) 2002-2008 10.1055/s-0030-1258128
30. Zeng, T.; Chen, W.-W.; Cirtiu, C. M.; Moores, A.; Song, G.; Li, C.-J. Fe3O4 nanoparticles: a robust and magnetically recoverable catalyst for three-component coupling of aldehyde, alkyne and amine Green Chem. 2010, 12 (4) 570-573 10.1039/b920000b
31. 4) Nanoparticles Synlett 2013, 24 (10) 1309-1310 10.1055/s-0033-1338949
32. Kantam, M. L.; Yadav, J.; Laha, S.; Jha, S. Synthesis of Propargylamines by Three-Component Coupling of Aldehydes, Amines and Alkynes Catalyzed by Magnetically Separable Copper Ferrite Nanoparticles Synlett 2009, 2009 (11) 1791-1794 10.1055/s-0029-1217362
33. Hudson, R.; Ishikawa, S.; Li, C.-J.; Moores, A. Magnetically Recoverable CuFe2O4 Nanoparticles as Highly Active Catalysts for Csp3-Csp and Csp3-Csp3 Oxidative Cross-Dehydrogenative Coupling Synlett 2013, 24 (13) 1637-1642 10.1055/s-0033-1339278
34. Anil Kumar, B. S. P.; Harsha Vardhan Reddy, K.; Madhav, B.; Ramesh, K.; Nageswar, Y. V. D. Magnetically separable CuFe2O4 nano particles catalyzed multicomponent synthesis of 1,4-disubstituted 1,2,3-triazoles in tap water using click chemistry Tetrahedron Lett. 2012, 53 (34) 4595-4599 10.1016/j.tetlet.2012.06.077
35. Li, C.-J.; Moores, A.; Ishikawa, S.; Hudson, R. Ligand Modified CuFe2O4 Nanoparticles as Magnetically Recoverable and Reusable Catalyst for Azide-Alkyne Click Condensation Heterocycles 2012, 86 (2) 1023-1030 10.3987/COM-12-S(N)125
36. Kantam, M. L.; Yadav, J.; Laha, S.; Srinivas, P.; Sreedhar, B.; Figueras, F. Asymmetric Hydrosilylation of Ketones Catalyzed by Magnetically Recoverable and Reusable Copper Ferrite Nanoparticles J. Org. Chem. 2009, 74 (12) 4608-4611 10.1021/jo9002823
37. Kumar, A. S.; Reddy, M. A.; Knorn, M.; Reiser, O.; Sreedhar, B. Magnetically Recoverable CuFe2O4 Nanoparticles: Catalyzed Synthesis of Aryl Azides and 1,4-Diaryl-1,2,3-triazoles from Boronic Acids in Water Eur. J. Org. Chem. 2013, 2013 (21) 4674-4680 10.1002/ejoc.201300343
38. Panda, N.; Jena, A. K.; Mohapatra, S.; Rout, S. R. Copper ferrite nanoparticle-mediated N-arylation of heterocycles: a ligand-free reaction Tetrahedron Lett. 2011, 52 (16) 1924-1927 10.1016/j.tetlet.2011.02.050
39. Zhang, R.; Liu, J.; Wang, S.; Niu, J.; Xia, C.; Sun, W. Magnetic CuFe2O4 Nanoparticles as an Efficient Catalyst for C-O Cross-Coupling of Phenols with Aryl Halides ChemCatChem 2011, 3 (1) 146-149 10.1002/cctc.201000254
40. Swapna, K.; Murthy, S. N.; Jyothi, M. T.; Nageswar, Y. V. D. Nano-CuFe2O4 as a magnetically separable and reusable catalyst for the synthesis of diaryl/aryl alkyl sulfidesvia cross-coupling process under ligand-free conditions Org. Biomol. Chem. 2011, 9 (17) 5989-5996 10.1039/c1ob05597f
41. Swapna, K.; Murthy, S. N.; Nageswar, Y. V. D. Magnetically Separable and Reusable Copper Ferrite Nanoparticles for Cross-Coupling of Aryl Halides with Diphenyl Diselenide Eur. J. Org. Chem. 2011, 2011 (10) 1940-1946 10.1002/ejoc.201001639
42. Liang, M.; Fan, K.; Pan, Y.; Jiang, H.; Wang, F.; Yang, D.; Lu, D.; Feng, J.; Zhao, J.; Yang, L.; Yan, X. Fe3O4 magnetic nanoparticle peroxidase mimetic-based colorimetric assay for the rapid detection of organophosphorus pesticide and nerve agent Anal. Chem. 2013, 85 (1) 308-312 10.1021/ac302781r
43. Hudson, R.; Luska, K. L. Recording Tutorials To Increase Student Use and Incorporating Demonstrations To Engage Live Participants J. Chem. Educ. 2013, 90 (5) 527-530 10.1021/ed300497g