Y. Huang et al. / Journal of Catalysis 292 (2012) 111–117
117
[
7] F.J. Urbano, J.M. Marinas, J. Mol. Catal. A 173 (2001) 329.
98
100
97
96
95
[8] M.A. Aramendía, V. Borau, I.M. García, C. Jimeénez, A. Marinas, J.M. Marinas, F.J.
Urbano, Surf. Chem. Catal. 3 (2000) 465.
92
[
9] C. Xia, Y. Liu, S. Zhou, C. Yang, S. Liu, J. Xu, J. Yu, J. Chen, X. Liang, J. Hazard.
Mater. 169 (2009) 1029.
80
60
40
20
0
[
[
10] S.S. Gupta, M. Stadler, C.A. Noser, A. Ghosh, B. Steinho, D. Lenoir, C.P. Horwitz,
K.W. Schramm, T.J. Collins, Science 296 (2002) 326.
11] X. Liang, D. Fu, R. Liu, Q. Zhang, T. Zhang, X. Hu, Angew. Chem. Int. Ed. 44
(2005) 5520.
12] C.E. Hetrick, J. Lichtenberger, M.D. Amiridis, Appl. Catal. B 77 (2008) 255.
13] S. Zinovyev, A. Shelepchikov, P. Tundo, Appl. Catal. B 72 (2007) 289.
14] A. Arcadi, G. Cerichelli, M. Chiarini, R. Vico, D. Zorzan, Eur. J. Org. Chem. (2004)
[
[
[
3404.
[
[
15] H. Hildebrand, K. Mackenzie, F.-D. Kopinke, Appl. Catal. B 91 (2009) 389.
16] Y. Lan, L. Yang, M. Zhang, W. Zhang, S. Wang, ACS Appl. Mater. Interfaces 2
(2010) 127.
17] Z. Jin, C. Yu, X. Wang, Y. Wan, D. Li, G. Lu, Chem. Commun. 45 (2009) 4438.
18] C.A. Ohlin, Z. Béni, G. Laurenczy, N. Ruiz, Anna M. Masdeu-Bultó, Appl.
Organomet. Chem. 21 (2007) 156.
[
[
[
[
19] K. Yang, B. Wang, L. Chen, X. Wang, Catal. Commun. 9 (2008) 431.
20] L. Chen, K. Yang, H. Liu, X. Wang, Carbon 46 (2008) 2137.
1
2
3
4
5
Run
[21] S. Gómez-Quero, E. Díaz, F. Cárdenas-Lizana, M.A. Keane, Chem. Eng. Sci. 65
2010) 3786.
(
Fig. 5. Recycling of Pd/MIL-101(Cr)–NH
-chlorophenol at room temperature for 3 h.
2
for five runs of the dehalogenation of
[22] R. Hartung, D. Lenoir, B. Henkelmann, S. Schulte-Hostede, K.-W. Schramm,
Clean 35 (2007) 235.
4
[
[
23] B. Immaraporn, P. Ye, A.J. Gellman, J. Catal. 223 (2004) 98.
24] P. Št eˇ pni cˇ ka, M. Semler, J. Demel, A. Zukal, J. Cˇ ejka, J. Mol. Catal. A 341 (2011)
9
7.
conveniently carried out in air and that the separation of the cata-
lyst can be achieved easily by centrifugation. After being recycled
for five runs of the dehalogenation reaction of 4-chlorophenol,
the Pd catalyst still exhibits remarkable activity (the yield de-
creased only 6%) (Fig. 5). The PXRD study shows that the crystalline
structure of the catalyst is mostly retained after five catalytic cy-
cles (Fig. 1). The TEM image of the reused catalyst reveals that
the Pd NPs size is very similar to the initial material (Fig. 3). This
may be ascribed to confinement of the Pd NPs in mesoporous cages
and thus restriction of their growth. These results indicate that the
reaction proceeds in a heterogeneous fashion [38–48].
[
25] Y. Monguchi, A. Kume, K. Hattori, T. Maegawa, H. Sajiki, Tetrahedron 62 (2006)
7926.
26] J.Y. Kim, Y. Jo, S. Lee, H.C. Choi, Tetrahedron Lett. 50 (2009) 6290.
27] S. Berardi, M. Carraro, M. Iglesias, A. Sartorel, G. Scorrano, M. Albrecht, M.
Bonchio, Chem. Eur. J. 16 (2010) 10662.
[
[
[28] J. Moon, S. Lee, J. Organomet. Chem. 694 (2009) 473.
[
29] W.M. Czaplik, S. Grupe, M. Mayer, A.J. von Wangelin, Chem. Commun. 46
2010) 6350.
30] Z. Zhang, Q. Shen, N. Cissoko, J. Wo, X. Xu, J. Hazard. Mater. 182 (2010) 252.
(
[
[31] Z. Zhang, N. Cissoko, J. Wo, X. Xu, J. Hazard. Mater. 165 (2009) 78.
32] R. Cheng, J. Wang, W. Zhang, Sci. China Ser. B 50 (2007) 574.
[
[
33] M.S.M.M. Rahuman, L. Pistone, F. Trifirò, S. Miertus, Destruction Technologies
for Polychlorinated Biphenyls (PCBS), in: ICS-UNIDO PUBLICATIONS
‘‘Proceedings of Expert Group Meetings on POPs and Pesticides
Contamination: Remediation Technologies (April 2000) and on Clean
4
. Conclusions
[
34] G. Férey, C. Mellot-Draznieks, C. Serre, F. Millange, J. Dutour, S. Surblé, I.
Margiolaki, Science 309 (2005) 2040.
In summary, highly dispersed Pd NPs encapsulated in amine-
[
[
35] L. Ma, C. Abney, W. Lin, Chem. Soc. Rev. 38 (2009) 1248.
36] A. Corma, H. Garcia, F.X.L. i Xamena, Chem. Rev. 110 (2010) 4606.
functionalized mesoporous MOFs MIL-101(Cr)–NH
2
have been pre-
9
pared easily with the help of NaBH under mild conditions. The
4
[37] M. Meilikhov, K. Yusenko, D. Esken, S. Turner, G.V. Tendeloo, R.A. Fischer, Eur. J.
Inorg. Chem. (2010) 3701.
well-dispersed Pd NPs confined in mesoporous cages showed high
activity for dehalogenation of aryl chlorides in water under mild
conditions. Furthermore, the catalyst is easily recoverable and
can be reused several times without leaching or loss of activity.
[
[
38] B. Yuan, Y. Pan, Y. Li, B. Yin, H. Jiang, Angew. Chem. Int. Ed. 49 (2010) 4054.
39] Y.K. Hwang, D.Y. Hong, J.S. Chang, S.H. Jhung, Y.K. Seo, J. Kim, A. Vimont, C.
Serre, G. Férey, Angew. Chem. Int. Ed. 47 (2008) 4144.
[
[
40] M.S. El-Shall, V. Abdelsayed, A.E.R.S. Khder, H.M.A. Hassan, H.M. El-Kaderi, T.E.
Reich, J. Mater. Chem. 19 (2009) 7625.
41] A. Henschel, K. Gedrich, R. Kraehnert, S. Kaskel, Chem. Commun. 44 (2008)
4192.
Acknowledgments
[
[
42] J. Hermannsdörfer, R. Kempe, Chem. Eur. J. 17 (2011) 8071.
43] S. Opelt, S. Türk, E. Dietzsch, A. Henschel, S. Kaskel, E. Klemm, Catal. Commun.
We acknowledge financial support from the 973 Program
9
(2008) 1286.
(
9
(
2011CB932504 and 2012CB821705), the NSFC (21003128 and
1022007), the Fujian Key Laboratory of Nanomaterials
2006L2005), and the Key Project from CAS.
[44] S. Hermes, F. Schröder, S. Amirjalayer, R. Schmid, R.A. Fischer, J. Mater. Chem.
16 (2006) 2464.
[
[
45] M. Müller, O.I. Lebedev, R.A. Fischer, J. Mater. Chem. 18 (2008) 5274.
46] D. Esken, X. Zhang, O.I. Lebedev, F. Schröoder, R.A. Fischer, J. Mater. Chem. 19
(
2009) 1314.
[
[
47] F.X.L. i Xamena, A. Abad, A. Corma, H. Garcia, J. Catal. 250 (2007) 294.
48] M. Sabo, A. Henschel, H. Fröde, E. Klemmb, S. Kaskel, J. Mater. Chem. 17 (2007)
Appendix A. Supplementary material
3
827.
[49] D. Esken, S. Turner, O.I. Lebedev, G.V. Tendeloo, R.A. Fischer, Chem. Mater. 22
2010) 6393.
[
[
(
50] X. Zhang, F.X.L. i Xamena, A. Corma, J. Catal. 265 (2009) 155.
51] Y. Huang, Z. Lin, R. Cao, Chem. Eur. J. 17 (2011) 12706.
References
[52] Y. Huang, Z. Zheng, T. Liu, J. Lü, Z. Lin, H. Li, R. Cao, Catal. Commun. 14 (2011)
7.
2
[
[
1] P. Selvam, S.K. Mohapatra, S.U. Sonavane, R.V. Jayaram, Appl. Catal. B 49 (2004)
51.
3] W. Zhou, D. Fu, Z. Sun, Res. Environ. Sci 6 (1991) 9.
4] H.-Y. Wee, J.A. Cunningham, J. Hazard. Mater. 155 (2008) 1.
5] V.I. Kovalchuk, J.L. d’Itri, Appl. Catal. A 271 (2004) 13.
6] F. Alonso, I.P. Beletskaya, M. Yus, Chem. Rev. 102 (2002) 4009.
[53] Y. Huang, S. Gao, T. Liu, J. Lü, X. Lin, H. Li, R. Cao, ChemPlusChem 77 (2012) 106.
[54] J. Gascon, U. Aktay, M.D. Hernandez-Alonso, G.P.M. van Klink, F. Kapteijn, J.
Catal. 261 (2009) 75.
[55] S. Bernt, V. Guillerm, C. Serreb, N. Stock, Chem. Commun. 47 (2011) 2838.
[56] O.V. Zalomaeva, K.A. Kovalenko, Y.A. Chesalov, M.S. Mel’gunov, V.I. Zaikovskii,
V.V. Kaichev, A.B. Sorokin, O.A. Kholdeeva, V.P. Fedin, Dalton Trans. 40 (2011)
1441.
2
[
[
[
[