Solvent-free aerobic oxidation of hydrocarbons and alcohols with Pd@N-doped carbon from glucose

Nature Communications

Volumn 4, Issue , 2013, Pages

  Zhang, Pengfei ^a   Gong, Yutong ^a   Li, Haoran ^a,b   Chen, Zhirong ^b   Wang, Yong ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL; ALDEHYDE; CARBON; ESTER; GLUCOSE; HYDROCARBON; KETONE; NANOPARTICLE; NITROGEN; OXYGEN; PALLADIUM; PALLADIUM NANOPARTICLE; SOLVENT; UNCLASSIFIED DRUG;

ALCOHOL; AMBIENT AIR; CARBON; CATALYST; GLUCOSE; HYDROCARBON; OXIC CONDITIONS; OXIDATION; PERFORMANCE ASSESSMENT; SOLVENT;

AEROBIC METABOLISM; AIR; ALCOHOL OXIDATION; AMBIENT AIR; ARTICLE; ATMOSPHERE; CATALYSIS; CATALYST; CONTROLLED STUDY; DOPING; NANOFABRICATION; OXIDATION KINETICS; POROSITY; RECYCLING; SCANNING ELECTRON MICROSCOPY; SOLVENT FREE AEROBIC OXIDATION; TRANSMISSION ELECTRON MICROSCOPY; TURNOVER TIME; X RAY DIFFRACTION;

AEROBIOSIS; AIR; ALCOHOLS; CARBON; CATALYSIS; GLUCOSE; HYDROCARBONS; KINETICS; NANOSTRUCTURES; NITROGEN; OXIDATION-REDUCTION; OXYGEN; PALLADIUM; PHOTOELECTRON SPECTROSCOPY; SOLVENTS; TIME FACTORS;

EID: 84875838973     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms2586     Document Type: Article

References (53)

1. Sheldon, R. A. & Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds (Academic Press, 1981).
2. Muzart, J. Chromium-catalyzed oxidations in organic synthesis. Chem. Rev. 92, 113-140 (1992).
3. Saiman, M. et al. Involvement of surface-bound radicals in the oxidation of toluene using supported Au-Pd nanoparticles. Angew. Chem. Int. Ed. 51, 5981-5985 (2012).
4. Wang, Y., Zhang, J. S., Wang, X. C., Antonietti, M. & Li, H. R. Boron-and fluorine-containing mesoporous carbon nitride polymers: metal-free catalysts for cyclohexane oxidation. Angew. Chem. Int. Ed. 49, 3356-3359 (2010).
5. Zhou., H. et al. Defect-less, layered organo-titanosilicate with superhydrophobicity and its catalytic activity in room-temperature olefin epoxidation. Chem. Commun. 48, 6954-6956 (2012).
6. Tong, X., Xu, J. & Miao, H. Highly efficient and metal-free aerobic hydrocarbons oxidation process by an o-phenanthroline-mediated organocatalytic system. Adv. Synth. Catal. 347, 1953-1957 (2005). (Pubitemid 41803154)
7. Waser, M., Jary, W. G., Pöchlauer, P. & Falk, H. J. Mol. Catal. A Chem. 236, 187-193 (2005).
8. Shannon, S. S. Palladium-catalyzed oxidation of organic chemicals with O#inf#2#/inf#. Science 309, 1824-1826 (2005).
9. Peterson, K. P. & Larock, R. C. Palladium-catalyzed oxidation of primary and secondary allylic and benzylic alcohols. J. Org. Chem. 63, 3185-3189 (1998). (Pubitemid 128500461)
10. Schultz, M. J., Park, C. C. & Sigman, M. S. A convenient palladium-catalyzed aerobic oxidation of alcohols at room temperature. Chem. Commun. 3034-3035 (2002). (Pubitemid 36044172)
11. Bianchi, D., Bortolo, R., Aloisio, R. D. & Ricci, M. Biphasic synthesis of hydrogen peroxide from carbon monoxide, water, and oxygen catalyzed by palladium complexes with bidentate nitrogen ligands. Angew. Chem. Int. Ed. 38, 706-708 (1999). (Pubitemid 29129840)
12. ten Brink, G.-J., Arends, I. W. C. E. & Sheldon, R. A. Green, catalytic oxidation of alcohols in water. Science 287, 1636-1639 (2000).
13. Ferreira, E. M. & Stoltz, B. M. The palladium-catalyzed oxidative kinetic resolution of secondary alcohols with molecular oxygen. J. Am. Chem. Soc. 123, 7725-7726 (2001). (Pubitemid 32899418)
14. Iwasawa, T., Tokunaga, M., Obora, Y. & Tsuji, Y. Homogeneous palladium catalyst suppressing Pd black formation in air oxidation of alcohols. J. Am. Chem. Soc. 126, 6554-6555 (2004). (Pubitemid 38697347)
15. Shannon, S. S. Palladium oxidase catalysis: selective oxidation of organic chemicals by direct dioxygen-coupled turnover. Angew. Chem. Int. Ed. 43, 3400-3420 (2004).
16. Wight, A. P. & Davis, M. E. Design and preparation of organic-inorganic hybrid catalysts. Chem. Rev. 102, 3589-3614 (2002). (Pubitemid 35350660)
17. Mori, K., Hara, T., Mizugaki, T., Ebitani, K. & Kaneda, K. Hydroxyapatite-supported palladium nanoclusters: a highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen. J. Am. Chem. Soc. 126, 10657-10666 (2004). (Pubitemid 39129166)
18. Parlett, C. A., Bruce, D., Hondow, N., Lee, A. & Wilson, K. Support-enhanced selective aerobic alcohol oxidation over Pd/mesoporous silicas. ACS Catal. 1, 636-640 (2011).
19. Karimi, B., Abedi, S., Clark, J. & Budarin, V. Highly efficient aerobic oxidation of alcohols using a recoverable catalyst: the role of mesoporous channels of SBA-15 in stabilizing palladium nanoparticles. Angew. Chem. Int. Ed. 45, 4776-4779 (2006). (Pubitemid 44179111)
20. Hou, Z., Theyssen, N., Brinkmann, A. & Leitner, W. Biphasic aerobic oxidation of alcohols catalyzed by poly(ethylene glycol)-stabilized palladium nanoparticles in supercritical carbon dioxide. Angew. Chem. Int. Ed. 44, 1346-1349 (2005). (Pubitemid 40343544)
21. Uozumi, Y. & Nakao, R. Catalytic oxidation of alcohols in water under atmospheric oxygen by use of an amphiphilic resin-dispersion of a nanopalladium catalyst. Angew. Chem. Int. Ed. 42, 194-197 (2003). (Pubitemid 36125575)
22. Chen, Y., Bai, L., Zhou, C., Lee, J. & Yang, Y. Palladium-catalyzed aerobic oxidation of 1-phenylethanol with an ionic liquid additive. Chem. Commun. 47, 6452-6454 (2011).
23. Villa, A. et al. Pd on carbon nanotubes for liquid phase alcohol oxidation. Catal. Today 150, 8-15 (2010).
24. Chen, Y. et al. Pd catalysts supported on MnCeO#inf#x#/inf# mixed oxides and their catalytic application in solvent-free aerobic oxidation of benzyl alcohol: support composition and structure sensitivity. J. Catal. 283, 34-44 (2011).
25. Llabrés i Xamena, F., Abad, A., Corma, A. & Garcia, H. MOFs as catalysts: activity, reusability and shape-selectivity of a Pd-containing MOF. J. Catal. 250, 294-298 (2007). (Pubitemid 47238829)
26. Enache, D. et al. Solvent-free oxidation of primary alcohols to aldehydes using Au-Pd TiO#inf#2#/inf# catalysts. Science 311, 362-365 (2006). (Pubitemid 43132657)
27. Davis, S., Ide, M. & Davis, R. Selective oxidation of alcohols and aldehydes over supported metal nanoparticles. Green Chem. 15, 17-45 (2013).
28. ten Brink, G.-J., Arends, I. W. C. E., Papadogianakis, G. & Sheldon, R. A. Catalytic conversions in water Part 13. aerobic oxidation of olefins to methyl ketones catalysed by a water-soluble palladium complex-mechanistic investigations. Appl. Catal. A Gen. 194-195, 435-442 (2000).
29. Bueno, A., de Souza, A. & Gusevskaya, E. Palladium-catalyzed oxidation of phenyl-substituted alkenes using molecular oxygen as the sole oxidant. Adv. Synth. Catal. 351, 2491-2495 (2009).
30. Gligorich, K. & Sigman, M. Recent advancements and challenges of palladium#sup#II#/sup#-catalyzed oxidation reactions with molecular oxygen as the sole oxidant. Chem. Commun. 3854-3867 (2009).
31. Fu, B., Zhu, X. & Xiao, G. Solvent-free selective aerobic oxidation of toluene by ultra fine nano-palladium catalyst. Appl. Catal. A Gen. 415-416, 47-52 (2012).
32. Campbell, A. & Stahl, S. Overcoming the 'oxidant problem': strategies to use O#inf#2#/inf# as the oxidant in organometallic C-H oxidation reactions catalyzed by Pd (and Cu). Acc. Chem. Res. 45, 851-863 (2012).
33. Kesavan, L. et al. Solvent-free oxidation of primary carbon-hydrogen bonds in toluene using Au-Pd alloy nanoparticles. Science 331, 195-199 (2011).
34. Antonietti, M. & Müllen, K. Carbon: the sixth element. Adv. Mater. 22, 787 (2010).
35. Wan, Y. et al. Ordered mesoporous Pd/silica-carbon as a highly active heterogeneous catalyst for coupling reaction of chlorobenzene in aqueous media. J. Am. Chem. Soc. 131, 4541-4550 (2009).
36. Hao, Y. et al. Bimetallic Au-Pd nanoparticles confined in tubular mesoporous carbons as highly selective and reusable benzyl alcohol oxidation catalysts. Chem. Cat. Chem. 4, 1595-1602 (2012).
37. Zhao, L. et al. Nitrogen-containing hydrothermal carbons with superior performance in supercapacitors. Adv. Mater. 22, 5202-5206 (2010).
38. Wang, Y., Yao, J., Li, H. R., Su, D. & Markus, A. Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media. J. Am. Chem. Soc. 133, 2362-2365 (2011).
39. Gong, K. P., Du, F., Xia, Z. H., Durstock, M. & Dai, L. M. Nitrogen-doped carbon nanotube arrays with high electrocatalytic activity for oxygen reduction. Science 323, 760-764 (2009).
40. Paraknowitsch, J. P., Thomas, A. & Antonietti, M. A detailed view on the polycondensation of ionic liquid monomers towards nitrogen doped carbon materials. J. Mater. Chem. 20, 6746-6758 (2010).
41. Titirici, M. & Antonietti, M. Chemistry and materials options of sustainable carbon materials made by hydrothermal carbonization. Chem. Soc. Rev. 39, 103-116 (2010).
42. White, R., Yoshizawa, N., Antonietti, M. & Titirici, M. A sustainable synthesis of nitrogen-doped carbon aerogels. Green Chem. 13, 2428-2434 (2011).
43. Fellinger, T.-P., White, R., Titirici, M.-M. & Antonietti, M. Borax-mediated formation of carbon aerogels from glucose. Adv. Funct. Mater. 22, 3254-3260 (2012).
44. Long, J. et al. Nitrogen-doped graphene nanosheets as metal-free catalysts for aerobic selective oxidation of benzylic alcohol. ACS Catal. 2, 622-631 (2012).
45. Xuan, X. et al. Synthesis of palladium nanoparticles supported on mesoporous N-doped carbon and their catalytic ability for biofuel upgrade. J. Am. Chem. Soc. 134, 16987-16990 (2012).
46. Estrada, A. et al. Iron-substituted polyoxotungstates as catalysts in the oxidation of indane and tetralin with hydrogen peroxide. Appl. Catal. A Gen. 366, 275-281 (2009).
47. Llabrés i Xamena, F. X., Casanova, O., Galiasso Tailleur, R., Garcia, H. & Corma, A. Metal organic frameworks (MOFs) as catalysts: A combination of Cu#sup#2+#/sup# and Co#sup#2+#/sup# MOFs as an efficient catalyst for tetralin oxidation. J. Catal. 255, 220-227 (2008).
48. Dimitratos, N. et al. Solvent free liquid phase oxidation of benzyl alcohol using Au-supported catalysts prepared using a sol immobilization technique. Catal. Today 122, 317-324 (2007). (Pubitemid 46702498)
49. Chen, Y. et al. Formation of monometallic Au and Pd and bimetallic Au-Pd nanoparticles confined in mesopores via Ar glow-discharge plasma reduction and their catalytic applications in aerobic oxidation of benzyl alcohol. J. Catal. 289, 105-117 (2012).
50. Abad, A., Concepción, P., Corma, A. & García, H. A collaborative effect between gold and a support induces the selective oxidation of alcohols. Angew. Chem. Int. Ed. 44, 4066-4069 (2005). (Pubitemid 40886449)
51. Xie, X. et al. Nitrogen-doped graphene stabilized gold nanoparticles for aerobic selective oxidation of benzylic alcohols. RSC Adv. 2, 12438-12446 (2012).
52. Zope, B. N., Hibbits, D. D., Neurock, M. & Davis, R. J. Reactivity of the gold/water interface during selective oxidation catalysis. Science 330, 74-78 (2010).
53. Yuan, J., Giordano, C. & Antonietti, M. Ionic liquid monomers and polymers as precursors of highly conductive, mesoporous, graphitic carbon nanostructures. Chem. Mater. 22, 5003-5012 (2010).