Selective liquid phase oxidation of benzyl alcohol catalyzed by carbon nanotubes

Chemical Engineering Journal

Volumn 204-205, Issue , 2012, Pages 98-106

  Luo, Jin ^a   Peng, Feng ^a   Yu, Hao ^a   Wang, Hongjuan ^a  

^a SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

Benzyl alcohol; Carbon catalysis; Carbon nanotubes; Nitric acid; Selective oxidation

Indexed keywords

ADSORPTION DESORPTION; BENZYL ALCOHOL; BENZYL ALCOHOL CONVERSION; CARBON CATALYSTS; CATALYST LOADINGS; CATALYTIC PERFORMANCE; ELECTRON TRANSFER; GRAPHENE SHEETS; LIQUID-PHASE OXIDATION; MILD REACTION CONDITIONS; OPTIMAL CONDITIONS; REACTION PATHWAYS; REACTION TEMPERATURE; SELECTIVE LIQUID PHASE OXIDATION; SELECTIVE OXIDATION; TEM (TRANSMISSION ELECTRON MICROSCOPY); TERMINAL OXIDANTS;

ALDEHYDES; CARBON NANOTUBES; CATALYSIS; CATALYSTS; CATALYTIC OXIDATION; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GRAPHENE; LIQUIDS; LOADING; OXIDATION; PRECIOUS METALS; REUSABILITY; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

NITRIC ACID;

EID: 84865292417     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2012.07.098     Document Type: Article

References (58)

1. Paraskevopoulou P., Psaroudakis N., Koinis S., Stavropoulos P., Mertis K. Catalytic selective oxidation of benzyl alcohols to aldehydes with rhenium complexes. J. Mol. Catal. A: Chem. 2005, 240:27-32.
2. Hutchings G.J., Li G., Enache D.I., Edwards J., Carley A.F., Knight D.W. Solvent-free oxidation of benzyl alcohol with oxygen using zeolite-supported Au and Au-Pd catalysts. Catal. Lett. 2006, 110:7-13.
3. Chen Y., Lim H., Tang Q., Gao Y., Sun T., Yan Q., Yang Y. Solvent-free aerobic oxidation of benzyl alcohol over Pd monometallic and Au-Pd bimetallic catalysts supported on SBA-16 mesoporous molecular sieves. Appl. Catal. A: Gen. 2010, 380:55-65.
4. Zhan G., Huang J., Du M., Sun D., Abdul-Rauf I., Lin W., Hong Y., Li Q. Liquid phase oxidation of benzyl alcohol to benzaldehyde with novel uncalcined bioreduction Au catalysts: high activity and durability. Chem. Eng. J. 2012, 187:232-238.
5. Kuang Y.B., Islam N.M., Nabae Y., Hayakawa T., Kakimoto M. Selective aerobic oxidation of benzylic alcohols catalyzed by carbon-based catalysts: a nonmetallic oxidation system. Angew. Chem. Int. Ed. 2010, 49:436-440.
6. Dileep R., Bhat B.R. Palladium-schiff base-triphenylphosphine catalyzed oxidation of alcohols. Appl. Organomet. Chem. 2010, 24:663-666.
7. Cao E., Sankar M., Firth S., Lam K.F., Bethell D., Knight D.K., Hutchings G.J., McMillan P.F., Gavriilidis A. Reaction and Raman spectroscopic studies of alcohol oxidation on gold-palladium catalysts in microstructured reactors. Chem. Eng. J. 2011, 167:734-743.
8. Sheldon R.A., Dijksman A., Marino-Gonzalez A., Payeras A.M.I., Arends I.W.C.E. Efficient and selective aerobic oxidation of alcohols into aldehydes and ketones using ruthenium/TEMPO as the catalytic system. J. Am. Chem. Soc. 2001, 123:6826-6833.
9. Fukahori S., Morikawa M., Ninomiya J. Preparation of ruthenium-containing sheet composites using a papermaking technique for selective oxidation of alcohol. Chem. Eng. J. 2010, 157:311-315.
10. Villa A., Wang D., Dimitratos N., Su D., Trevisan V., Prati L. Pd on carbon nanotubes for liquid phase alcohol oxidation. Catal. Today 2010, 150:8-15.
11. Tsuruya S., Yamamoto R., Sawayama Y., Shibahara H., Ichihashi Y., Nishiyama S. Promoted partial oxidation activity of supported Ag catalysts in the gas-phase catalytic oxidation of benzyl alcohol. J. Catal. 2005, 234:308-317.
12. Choudhary V.R., Dhar A., Jana P., Jha R., Uphade B.S. A green process for chlorine-free benzaldehyde from the solvent-free oxidation of benzyl alcohol with molecular oxygen over a supported nano-size gold catalyst. Green Chem. 2005, 7:768-770.
13. 2, FeAPO-5 and NaBr for selective oxidation of benzyl alcohols. Catal. Commun. 2011, 16:225-228.
14. Rahimi R., Gholamrezapor E. Oxidation of benzyl alcohols to the corresponding carbonyl compounds catalyzed by copper (II) meso-tetra phenyl porphyrin as Cytochrome P-450 model reaction. Inorg. Chem. Commun. 2011, 14:1561-1568.
15. Liu S.X., Jia A.Z., Lou L.L., Zhang C., Zhang Y.Q. Selective oxidation of benzyl alcohol to benzaldehyde with hydrogen peroxide over alkali-treated ZSM-5 zeolite catalysts. J. Mol. Catal. A: Chem. 2009, 306:123-129.
16. Yu Y., Lu B., Wang X., Zhao J., Cai Q. Highly selective oxidation of benzyl alcohol to benzaldehyde with hydrogen peroxide by biphasic catalysis. Chem. Eng. J. 2010, 162:738-742.
17. Kuang Y.B., Rokubuichi H., Nabae Y., Hayakawa T., Kakimoto M. A nitric acid-assisted carbon-catalyzed oxidation system with nitroxide radical cocatalysts as an efficient and green protocol for selective aerobic oxidation of alcohols. Adv. Synth. Catal. 2010, 352:2635-2642.
18. 2 catalyst: a transition-metal-free approach to efficient aerobic oxidation of alcohols to aldehydes and ketones under mild conditions. Chem. Eur. J. 2008, 14:2679-2685.
19. Serp P., Castillejos E. Catalysis in carbon nanotubes. ChemCatChem 2010, 2:41-47.
20. Maksimova N., Mestl G., Schlögl R. Catalytic activity of carbon nanotubes and other carbon materials for oxidative dehydrogenation of ethylbenzene to styrene. Stud. Surf. Sci. Catal. 2001, 133:383-389.
21. Zhang J., Liu X., Blume R., Zhang A.H., Schlogl R., Su D.S. Surface-modified carbon nanotubes catalyze oxidative dehydrogenation of n-butane. Science 2008, 322:73-77.
22. Goettmann F., Fischer A., Antonietti M., Thomas A. Chemical synthesis of mesoporous carbon nitrides using hard templates and their use as a metal-free catalyst for Friedel-Crafts reaction of benzene. Angew. Chem. Int. Ed. 2006, 45:4467-4471.
23. Yu H., Peng F., Tan J., Hu X.W., Wang H.J., Yang J., Zheng W.X. Selective catalysis of the aerobic oxidation of cyclohexane in the liquid phase by carbon nanotubes. Angew. Chem. Int. Ed. 2011, 50:3978-3982.
24. Li X.H., Chen J.S., Wang X., Sun J., Antonietti M. Metal-free activation of dioxygen by graphene/g-C(3)N(4) nanocomposites: functional dyads for selective oxidation of saturated hydrocarbons. J. Am. Chem. Soc. 2011, 133:8074-8077.
25. Aellig C., Girard C., Hermans I. Aerobic alcohol oxidations mediated by nitric acid. Angew. Chem. Int. Ed. 2011, 50:12355-12360.
26. 3-mediated aerobic oxidation of benzyl alcohol. ChemCatChem 2012, 4:525-529.
27. Kuang Y.B., Nabae Y., Hayakawa T., Kakimoto M. Solvent free aerobic oxidation of alcohols with 1-methyl-2-azaadamantane N-oxyl as a recyclable catalyst through phase separation. Green Chem. 2011, 13:1659-1663.
28. Frank B., Zhang J., Blume R., Schloegl R., Su D.S. Heteroatoms increase the selectivity in oxidative dehydrogenation reactions on nanocarbons. Angew. Chem. Int. Ed. 2009, 48:6913-6917.
29. Cho H.H., Smith B.A., Wnuk J.D., Fairbrother D.H., Ball W.P. Influence of surface oxides on the adsorption of naphthalene onto multiwalled carbon nanotubes. Environ. Sci. Technol. 2008, 42:2899-2905.
30. Rinaldi A., Zhang J., Frank B., Su D.S., Hamid S.B.A., Schloegl R. Oxidative purification of carbon nanotubes and its impact on catalytic performance in oxidative dehydrogenation reactions. ChemSusChem 2010, 3:254-260.
31. Raymundo-Pinero E., Azais P., Cacciaguerra T., Cazorla-Amoros D., Linares-Solano A., Beguin F. KOH and NaOH activation mechanisms of multiwalled carbon nanotubes with different structural organisation. Carbon 2005, 43:786-795.
32. Lillo-Ródenas M., Cazorla-Amoros D., Linares-Solano A. Understanding chemical reactions between carbons and NaOH and KOH: an insight into the chemical activation mechanism. Carbon 2003, 41:267-275.
33. Fujisawa S., Kadoma Y., Yokoe I. Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. Chem. Phys. Lipids 2004, 130:189-195.
34. 2 adsorption. Chem. Eng. Sci. 2009, 64:3721-3728.
35. Kosa S.A., Al-Zhrani G., Salam M.A. Removal of heavy metals from aqueous solutions by multi-walled carbon nanotubes modified with 8-hydroxyquinoline. Chem. Eng. J. 2012, 181:159-168.
36. Sing K., Everett D., Haul R., Moscou L., Pierotti R., Rouquerol J., Siemieniewska T. Reporting physisorption data for gas/solid systems. Pure Appl. Chem. 1985, 57:603-619.
37. Wu G.Q., Zhang X., Hui H., Yan J., Zhang Q.S., Wan J.L., Dai Y. Adsorptive removal of aniline from aqueous solution by oxygen plasma irradiated bamboo based activated carbon. Chem. Eng. J. 2012, 185-186:201-210.
38. Baltrusaitis J., Jayaweera P.M., Grassian V.H. XPS study of nitrogen dioxide adsorption on metal oxide particle surfaces under different environmental conditions. Phys. Chem. Chem. Phys. 2009, 11:8295-8305.
39. 3: an in situ FTIR/MS study. J. Phys. Chem. C 2007, 111:2661-2669.
40. Joshi S.R., Kataria K.L., Sawant S.B., Joshi J.B. Kinetics of oxidation of benzyl alcohol with dilute nitric acid. Ind. Eng. Chem. Res. 2005, 44:325-333.
41. Mudgal P.K., Bansal S., Gupta K. Kinetics of atmospheric oxidation of nitrous acid by oxygen in aqueous medium. Atmos. Environ. 2007, 41:4097-4105.
42. Ren X., Chen C., Nagatsu M., Wang X. Carbon nanotubes as adsorbents in environmental pollution management: a review. Chem. Eng. J. 2011, 170:395-410.
43. Chen W., Duan L., Zhu D. Adsorption of polar and nonpolar organic chemicals to carbon nanotubes. Environ. Sci. Technol. 2007, 41:8295-8300.
44. D'Angelo F.A., Brunet L., Cognet P., Cabassud M. Modelling and constraint optimisation of an aromatic nitration in liquid-liquid medium. Chem. Eng. J. 2003, 91:75-84.
45. Liu L., Ma J., Xia J., Li L., Li C., Zhang X., Gong J., Tong Z. Confining task-specific ionic liquid in silica-gel matrix by sol-gel technique: a highly efficient catalyst for oxidation of alcohol with molecular oxygen. Catal. Commun. 2011, 12:323-326.
46. Krupke R., Hennrich F., Löhneysen H., Kappes M.M. Separation of metallic from semiconducting single-walled carbon nanotubes. Science 2003, 301:344-347.
47. Kong J., Franklin N.R., Zhou C., Chapline M.G., Peng S., Cho K., Dai H. Nanotube molecular wires as chemical sensors. Science 2000, 287:622-625.
48. Prato M., Kostarelos K., Bianco A. Functionalized carbon nanotubes in drug design and discovery. Acc. Chem. Res. 2008, 41:60-68.
49. Eitan A., Jiang K., Dukes D., Andrews R., Schadler L.S. Surface modification of multiwalled carbon nanotubes: toward the tailoring of the interface in polymer composites. Chem. Mater. 2003, 15:3198-3201.
50. Deng J., Shao Y., Gao N., Deng Y., Tan C., Zhou S., Hu X. Multiwalled carbon nanotubes as adsorbents for removal of herbicide diuron from aqueous solution. Chem. Eng. J. 2012, 193-194:339-347.
51. Baleizão C., Gigante B., Garcia H., Corma A. Vanadyl salen complexes covalently anchored to single-wall carbon nanotubes as heterogeneous catalysts for the cyanosilylation of aldehydes. J. Catal. 2004, 221:77-84.
52. Zhang J., Su D., Zhang A., Wang D., Schloegl R., Hebert C. Nanocarbon as robust catalyst: mechanistic insight into carbon-mediated catalysis. Angew. Chem. Int. Ed. 2007, 46:7319-7323.
53. Yang S., Li X., Zhu W., Wang J., Descorme C. Catalytic activity, stability and structure of multi-walled carbon nanotubes in the wet air oxidation of phenol. Carbon 2008, 46:445-452.
54. Dreyer D.R., Jia H.P., Bielawski C.W. Graphene oxide: a convenient carbocatalyst for facilitating oxidation and hydration reactions. Angew. Chem. Int. Ed. 2010, 49:6813-6816.
55. Figueiredo J., Pereira M., Freitas M., Orfao J. Modification of the surface chemistry of activated carbons. Carbon 1999, 37:1379-1389.
56. Zhang H., Sun C.H., Li F., Li H.X., Cheng H.M. Purification of multiwalled carbon nanotubes by annealing and extraction based on the difference in van der Waals potential. J. Phys. Chem. B 2006, 110:9477-9481.
57. Andrews R., Jacques D., Qian D., Dickey E. Purification and structural annealing of multiwalled carbon nanotubes at graphitization temperatures. Carbon 2001, 39:1681-1687.
58. Kim Y., Hayashi T., Osawa K., Dresselhaus M., Endo M. Annealing effect on disordered multi-wall carbon nanotubes. Chem. Phys. Lett. 2003, 380:319-324.