Catalytic hydrogenation of 2,3,5-trimethylbenzoquinone over Pd nanoparticles confined in the cages of MIL-101(Cr)

Chemical Engineering Journal

Volumn 239, Issue , 2014, Pages 33-41

  Zhao, Xiaomin ^a   Jin, Yan ^a   Zhang, Fumin ^a   Zhong, Yijun ^a   Zhu, Weidong ^a  

^a ZHEJIANG NORMAL UNIVERSITY   (China)

Author keywords

2,3,5 Trimethylbenzoquinone; 2,3,5 Trimethylhydroquinone; Catalytic hydrogenation; Metal organic frameworks; Pd catalyst

Indexed keywords

ACTIVATED CARBON; BATCH REACTORS; CATALYST SELECTIVITY; CATALYST SUPPORTS; CHROMIUM METALLOGRAPHY; HYDROGENATION; METAL NANOPARTICLES; METAL-ORGANIC FRAMEWORKS; ORGANIC POLYMERS; ORGANOMETALLICS; PALLADIUM; REUSABILITY;

2,3,5-TRIMETHYLBENZOQUINONE; 2,3,5-TRIMETHYLHYDROQUINONE; ACTIVATED CARBON SUPPORTED; CATALYTIC HYDROGENATION; CO CHEMISORPTION; INCIPIENT WETNESS IMPREGNATION METHOD; INTRINSIC ACTIVITIES; PD CATALYST;

CATALYST ACTIVITY;

EID: 84888390886     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2013.11.003     Document Type: Article

References (62)

1. Carril M., Altmann P., Bonrath W., Netscher T., Schutz J., Euhn F. Methyltrioxorhenium-catalysed oxidation of pseudocumene in the presence of amphiphiles for the synthesis of vitamin E. Catal. Sci. Technol. 2012, 2:722-724.
2. Carril M., Altmann P., Drees M., Bonrath W., Netscher T., Schutz J., Kuhn F.E. Methyltrioxorhenium-catalyzed oxidation of pseudocumene for vitamin E synthesis: a study of solvent and ligand effects. J. Catal. 2011, 283:55-67.
3. Bonrath W., Eggersdorfer M., Netscher T. Catalysis in the industrial preparation of vitamins and nutraceuticals. Catal. Today 2007, 121:45-57.
4. Bonrath W., Netscher T. Catalytic processes in vitamins synthesis and production. Appl. Catal. A 2005, 280:55-73.
5. Mukhopadhyay S., Chandnani K.H., Chandalia S.B. Kinetics of highly selective catalytic hydrogenation of 2,3,5-trimethylbenzoquinone on Raney nickel catalyst. Org. Process Res. Dev. 2000, 4:254-258.
6. P. Karrer, O. Isler, Process for the preparation of synthetic dl-a-tocopherols, US2411969[P], 1946-11-03.
7. G. L. Olson, G. Saucy, Synthesis of vitamin E, US4243598[P], 1981-01-06.
8. F. Jung, Process of preparing durohydroquinone, US2259936[P], 1941-10-21.
9. R. Oster, L. Schuster, Manufacture of trimethyl hydroquinone, CA880364[P], 1971-07-09.
10. Y. Tamai, K. Itoi, Process for producing 2,3,6-trimethylhydroquinone, US3839468[P], 1974-10-01.
11. T. Yui, A. Ito, Process of 2,3,5-trimethylhydroquinone, US4769500[P], 1988-09-06.
12. F.J. Bröecker, P. Tavs, H. Laas, W.K. Aders, Preparation of trimethyl hydroquinone, US4600799[P], 1986-07-15.
13. J.G.A. Bitter, R.J. Maas, J.H. Scheerman, Preparation of 2,3,5-trimethyl hydroquinone, US4250335[P], 1981-02-10.
14. F. Jung, Process for the production of trimethylhydroquinones, US2229573[P], 1941-01-21.
15. Z.Q. Zhu, Z.F. Yuan, Q.F. Xu, A method for the preparation of 2,3,5-trimethylhydroquinone, CN102241577[P], 2011-11-16.
16. W.D. Zhu, F.M. Zhang, L. Wu, Y.J. Zhong, Pd/C catalyst for producing TMHQ by virtue of hydrogenation of TMBQ and preparation method thereof, CN102294240[P], 2013-02-13.
17. Yaghi O.M., O'Keeffe M., Ockwig N.W., Chae H.K., Eddaoudi M., Kim J. Reticular synthesis and the design of new materials. Nature 2003, 423:705-714.
18. Kitagawa S., Kitaura R., Noro S. Functional porous coordination polymers. Angew. Chem. Int. Ed. 2004, 43:2334-2375.
19. Corma A., Garcia H., Xamena F.X.L. Engineering metal organic frameworks for heterogeneous catalysis. Chem. Rev. 2010, 110:4606-4655.
20. Meilikhov M., Yusenko K., Esken D., Turner S., Van Tendeloo G., Fischer R.A. Metals@MOFs-loading MOFs with metal nanoparticles for hybrid functions. Eur. J. Inorg. Chem. 2010, 2010:3701-3714.
21. Li J.R., Sculley J., Zhou H.C. Metal-organic frameworks for separations. Chem. Rev. 2012, 112:869-932.
22. Song Y.F., Cronin L. Postsynthetic covalent modification of metal-organic framework (MOF) materials. Angew. Chem. Int. Ed. 2008, 47:4635-4637.
23. Férey G., Mellot-Draznieks C., Serre C., Millange F., Dutour J., Surble S., Margiolaki I. A chromium terephthalate-based solid with unusually large pore volumes and surface area. Science 2005, 309:2040-2042.
24. Maksimchuk N.V., Kovalenko K.A., Fedin V.P., Kholdeeva O.A. Cyclohexane selective oxidation over metal-organic frameworks of MIL-101 family: superior catalytic activity and selectivity. Chem. Commun. 2012, 48:6812-6814.
25. Hasan Z., Jeon J., Jhung S.H. Adsorptive removal of naproxen and clofibric acid from water using metal-organic frameworks. J. Hazard. Mater. 2012, 209-210:151-157.
26. Li B.Y., Zhang Y.M., Ma D.X., Li L., Li G.H., Li G.D., Shi Z., Feng S.H. A strategy toward constructing a bifunctionalized MOF catalyst: post-synthetic modification of MOFs on organic ligands and coordinatively unsaturated metal sites. Chem. Commun. 2012, 48:6151-6153.
27. Goesten M.G., Juan-Alcaniz J., Ramos-Fernandez E.V., Gupta K., Stavitski E., van Bekkum H., Gascon J., Kapteijn F. Sulfation of metal-organic frameworks: opportunities for acid catalysis and proton conductivity. J. Catal. 2011, 281:177-187.
28. Taylor-Pashow K.M.L., Della Rocca J., Xie Z.G., Tran S., Lin W.B. Postsynthetic modifications of iron-carboxylate nanoscale metal-organic frameworks for imaging and drug delivery. J. Am. Chem. Soc. 2009, 131:14261-14263.
29. Khan N.A., Kang I.J., Seok H.Y., Jhung S.H. Facile synthesis of nano-sized metal-organic frameworks, chromium-benzenedicarboxylate, MIL-101. Chem. Eng. J. 2011, 166:1152-1157.
30. Zhao Z., Li X., Li Z. Adsorption equilibrium and kinetics of p-xylene on chromium-based metal organic framework MIL-101. Chem. Eng. J. 2011, 173:150-157.
31. Saha D., Zacharia R., Lafi L., Cossement D., Chahine R. Synthesis, characterization and hydrogen adsorption on metal-organic frameworks Al, Cr, Fe and Ga-BTB. Chem. Eng. J. 2011, 171:517-525.
32. Munusamy K., Sethia G., Patil D.V., Rallapalli P.B.S., Somani R.S., Bajaj H.C. Sorption of carbon dioxide, methane, nitrogen and carbon monoxide on MIL-101(Cr): volumetric measurements and dynamic adsorption studies. Chem. Eng. J. 2012, 195:359-368.
33. Hasan Z., Choi E.J., Jhung S.H. Adsorption of naproxen and clofibric acid over a metal-organic framework MIL-101 functionalized with acidic and basic groups. Chem. Eng. J. 2013, 219:537-544.
34. Chen C., Zhang M., Guan Q., Li W. Kinetic and thermodynamic studies on the adsorption of xylenol orange onto MIL-101 (Cr). Chem. Eng. J. 2012, 183:60-67.
35. Anbia M., Hoseini V. Development of MWCNT@MIL-101 hybrid composite with enhanced adsorption capacity for carbon dioxide. Chem. Eng. J. 2012, 191:326-330.
36. Dhakshinamoorthy A., Garcia H. Catalysis by metal nanoparticles embedded on metal-organic frameworks. Chem. Soc. Rev. 2012, 41:5262-5284.
37. Jiang H.L., Liu B., Akita T., Haruta M., Sakurai H., Xu Q. Au@ZIF-8: CO oxidation over gold nanoparticles deposited to metal-organic framework. J. Am. Chem. Soc. 2009, 131:11302-11305.
38. Sabo M., Henschel A., Frode H., Klemm E., Kaskel S. Solution infiltration of palladium into MOF-5: synthesis, physisorption and catalytic properties. J. Mater. Chem. 2007, 17:3827-3832.
39. Li H., Zhu Z.H., Zhang F., Xie S.H., Li H.X., Li P., Zhou X.G. Palladium nanoparticles confined in the cages of MIL-101: an efficient catalyst for the one-pot indole synthesis in water. ACS Catal. 2011, 1:1604-1612.
40. El-Shall M.S., Abdelsayed V., Khder A.E.R.S., Hassan H.M.A., El-Kaderi H.M., Reich T.E. Metallic and bimetallic nanocatalysts incorporated into highly porous coordination polymer MIL-101. J. Mater. Chem. 2009, 19:7625-7631.
41. Pan Y., Yuan B., Li Y., He D. Multifunctional catalysis by Pd@MIL-101: One-step synthesis of methyl isobutyl ketone over palladium nanoparticles deposited on a metal-organic framework. Chem. Commun. 2010, 46:2280-2282.
42. Hwang Y.K., Hong D.Y., Chang J.S., Jhung S.H., Seo Y.K., Kim J., Vimont A., Daturi M., Serre C., Férey G. Amine grafting on coordinatively unsaturated metal centers of MOFs: consequences for catalysis and metal encapsulation. Angew. Chem. Int. Ed. 2008, 47:4144-4148.
43. Huang Y., Liu S., Lin Z., Li W., Li X., Cao R. Facile synthesis of palladium nanoparticles encapsulated in amine-functionalized mesoporous metal-organic frameworks and catalytic for dehalogenation of aryl chlorides. J. Catal. 2012, 292:111-117.
44. Henschel A., Gedrich K., Kraehnert R., Kaskel S. Catalytic properties of MIL-101. Chem. Commun. 2008, 44:4192-4194.
45. Jiang H.L., Xu Q. Porous metal-organic frameworks as platforms for functional applications. Chem. Commun. 2011, 47:3351-3370.
46. Liu H.L., Li Y.W., Luque R., Jiang H.F. A tunable bifunctional water-compatible heterogeneous catalyst for the selective aqueous hydrogenation of phenols. Adv. Synth. Catal. 2011, 353:3107-3113.
47. Park T.H., Hickman A.J., Koh K., Martin S., Wong-Foy A.G., Sanford M.S., Matzger A.J. Highly dispersed palladium(II) in a defective metal-organic framework: application to C-H activation and functionalization. J. Am. Chem. Soc. 2011, 133:20138-20141.
48. 2-methanol solution: highly efficient catalyst. Green Chem. 2011, 13:2078-2082.
49. 2-MIL-101(Al) containing phosphotungstic acid: characterization and catalytic performance. J. Catal. 2012, 289:42-52.
50. Liu H., Li Y., Jiang H., Vargas C., Luque R. Significant promoting effects of Lewis acidity on Au-Pd systems in the selective oxidation of aromatic hydrocarbons. Chem. Commun. 2012, 48:8431-8433.
51. Hermannsdörfer J., Kempe R. Selective palladium-loaded MIL-101 catalysts. Chem. Eur. J. 2011, 17:8071-8077.
52. Yuan B.Z., Pan Y.Y., Li Y.W., Yin B.L., Jiang H.F. A highly active heterogeneous palladium catalyst for the Suzuki-Miyaura and Ullmann coupling reactions of aryl chlorides in aqueous media. Angew. Chem. Int. Ed. 2010, 49:4054-4058.
53. Cirujano F.G., Xamena F.X.L.I., Corma A. MOFs as multifunctional catalysts: One-pot synthesis of menthol from citronellal over a bifunctional MIL-101 catalyst. Dalton Trans. 2012, 41:4249-4254.
54. Hu X., Lu Y., Dai F., Liu C., Liu Y. Host-guest synthesis and encapsulation of phosphotungstic acid in MIL-101 via "bottle around ship": an effective catalyst for oxidative desulfurization. Microporous Mesoporous Mater. 2013, 170:36-44.
55. van Attekum P.M.T.M., Trooster J.M. Bulk- and surface-plasmon-loss intensities in photoelectron, Auger, and electron-energy-loss spectra of Mg metal. Phys. Rev. B 1979, 20:2335-2340.
56. Gniewek A., Trzeciak A.M., Ziółkowski J.J., Kepiński L., Wrzyszcz J., Tylus W. Pd-PVP colloid as catalyst for Heck and carbonylation reactions: TEM and XPS studies. J. Catal. 2005, 229:332-343.
57. Voogt E.H., Mens A.J.M., Gijzeman O.L.J., Geus J.W. XPS analysis of palladium oxide layers and particles. Surf. Sci. 1996, 350:21-31.
58. Cairns G.R., Cross R.J., Stirling D. Characterisation of catalysts and their precursors prepared from supported palladium phosphine complexes. J. Mol. Catal. A 2001, 172:207-218.
59. Ganesan M., Freemantle R.G., Obare S.O. Monodisperse thioether-stabilized palladium nanoparticles: synthesis, characterization, and reactivity. Chem. Mater. 2007, 19:3464-3471.
60. Küsgens P., Rose M., Senkovska I., Fröde H., Henschel A., Siegle S., Kaskel S. Characterization of metal-organic frameworks by water adsorption. Microporous Mesoporous Mater. 2009, 120:325-330.
61. Liu H., Jiang T., Han B., Liang S., Zhou Y. Selective phenol hydrogenation to cyclohexanone over a dual supported Pd-Lewis acid catalyst. Science 2009, 326:1250-1252.
62. Tarakeshwar P., Lee J.Y., Kim K.S. Role of Lewis acid (AlCl3)-aromatic ring interactions in Friedel-Craft's reaction: an ab initio study. J. Phys. Chem. A 1998, 102:2253-2255.