RSC Advances
Please do not adjust margins
Page 4 of 5
COMMUNICATION
Journal Name
1
2
(CH3CH2COONa) showed a faster reaction rate than in
saturated solution of CH3COONa. Additionally, the solution of
1-propanesulfonic acid sodium (CH3CH2CH2SO3Na, 96.2%)
showed better chlorobenzen conversion than the solution of
methanesulfonic acid sodium (CH3SO3Na, 83.7%), which were
both higher than the solution of NaSO4 (67.8%). These results
proved that longer side chain in the salts was beneficial for the
transfer hydrodehalogenation of chlorobenzen. Therefore, we
concluded that CH3COONa indeed played similar role as
surfactants to some extent. Thirdly, the dissolution of
CH3COONa in water could increase the ionic strength of the
solutions, which was beneficial for activating the C-Cl bond in
DOI: 10.1039/C6RA24559E
Xia, Sci. Rep., 2016, 6, 25068.
(a) R. Baumgartner, G. K. Stieger and K. McNeill, Environ. Sci.
Technol., 2013, 47, 6545; (b) E. L. Teuten and C. M. Reddy,
Environ. Pollut., 2007, 145, 668.; (c) J. Luo, J. Hu, X. Wei, L. Fu
and L. Li, Chemosphere, 2015, 131, 17.
3
4
B. R. Stanmore, Combust. Flame, 2004, 136, 398.
(a) H. I. Gomes, C. Dias-Ferreira and A. B. Ribeiro, Sci. Total
Environ., 2013, 445-446, 237; (b) X. Chen, W. Ma, J. Li, Z.
Wang, C. Chen, H. Ji and J. Zhao, J. Phys. Chem. C, 2011, 115,
4089.
(a) F. Alonso, I. P. Beletskaya and M. Yus, Chem. Rev., 2002,
102, 4009; (b) R. Navon, S. Eldad, K. Mackenzie and F.-D.
Kopinke, Appl. Catal. B: Environ., 2012, 119-120, 241.
5
6
chlorobenzene
through
the
interaction
between
́
́
(a) M. A. Aramendıa, V. Boráu, I. M. Garcıa, C. Jiménez, A.
Marinas, J. M. Marinas and F. J. Urbano, Appl. Catal. B:
Environ., 2003, 43, 71; (b) C. Xia, J. Xu, W. Wu and X. Liang,
Catal. Commun., 2004, 5, 383.
chlorobenzene and solvated ions, and thus enhancing the
transfer hydrodehalogenation. Through these discussions, we
assumed that the improvement effect of the CH3COONa
solution on the transfer hydrodehalogenation may be resulted
from the surfactant-similar effect of CH3COONa and the
activation of C-Cl bond by the dissolved solvated ions.
7
8
9
Y. L. Ren, G. Y. Fan and C. Y. Wang, J. Hazard. Mater., 2014,
274, 32.
S. Gómez-Quero, F. Cárdenas-Lizana and M. A. Keane, J.
Catal., 2013, 303, 41.
T. Yoneda, T. Takido and K. Konuma, Appl. Catal. B: Environ.,
2008, 84, 667.
10 C. B. Molina, A. H. Pizarro, J. A. Casas and J. J. Rodriguez,
Appl. Catal. B: Environ., 2014, 148-149, 330.
11 X. Ma, S. Zhou, C. Yang, S. Liu, S. Liu, X. Bi and C. Xia, Catal.
Commun., 2010, 12, 282.
12 (a) Y. Deng, B. Yang, G. Yu, Q. Zhu, S. Deng and H. Zhang,
Prog. Chem., 2016, 28, 564; (b) R. Garrido, P. S. Hernández-
Montes, Á. Gordillo, P. Gómez-Sal, C. López-Mardomingo
and E. de Jesús, Organometallics, 2015, 34, 1855; (c) H.
Tsurugi, A. Hayakawa, S. Kando, Y. Sugino and K. Mashima,
Chem. Sci., 2015, 6, 3434.
Fig. 3. Structure of acetate at the interface of oil phase and water
phase.
13 (a) G. V. Lowry and M. Reinhard, Environ. Sci. Technol., 1999,
33, 1905; (b) L. Hizartzidis, P. J. Cossar, M. J. Robertson, M. I.
Simone, K. A. Young, A. McCluskey and C. P. Gordon, RSC
Adv., 2014, 4, 56743.
14 G. Chelucci and S. Figus, J. Mol. Catal. A: Chem., 2014, 393,
191.
15 A. C. Bényei, S. Lehel and F. Joó, J. Mol. Catal. A: Chem., 1997,
116, 349.
16 (a) S. Akzinnay, F. Bisaro and C. S. J. Cazin, Chem. Commun.,
2009, 5752; (b) R. Abazari, F. Heshmatpour and S. Balalaie,
ACS Catal., 2013, 3, 139.
17 P. A. Grieco, J. J. Nunes and M. D. Gaul, J. Am. Chem. Soc.,
1990, 112, 4595.
18 A. Kumar and S. S. Pawar, Tetrahedron, 2003, 59, 5019.
19 S. Tiwari and A. Kumar, Chem. Commun., 2008, 4445.
20 (a) K. C. Westaway, Y. Gao and Y.-R. Fang, J. Org. Chem.,
2003, 68, 3084; (b) M. J. Pregel and E. Buncel, J. Chem. Soc.,
Perkin Trans. 2, 1991, 307.
21 (a) Z. Xue, B. Cao, W. Zhao, J. Wang, T. Yu, T. Mu, RSC Adv.,
2016, 6, 64338. (b) T. vom Stein, P. Grande, F. Sibilla, U.
Commandeur, R. Fischer, W. Leitner and P. D. de María,
Green Chem., 2010, 12, 1844.
22 (a) A. Kumar, Chem. Rev., 2001, 101, 1; (b) C. Yan, T. Mu,
Phys. Chem. Chem. Phys., 2015, 17, 3241; (c) C. Yan, Z. Xue,
W. Zhao, J. Wang, T. Mu, ChemPhysChem, 2016, 17, 3309.
23 K. Mackenzie, H. Frenzel and F.-D. Kopinke, Appl. Catal. B:
Environ., 2006, 63, 161.
Conclusions
In summary, saturated aqueous solution of CH3COONa was
found to be an efficient and environmentally-friendly reaction
media for transfer hydrodehalogenation of aryl halides using
Pd/C as the catalyst. For various aryl chlorides, there was only
hydrodehalogenation reaction happened in the presence of
other unsaturated groups in the CH3COONa solution.
Meanwhile, the CH3COONa solution could even improve the
reaction of fluorobenzene, which could not be conducted in
pure water. Additionally, bromobenzene and iodobenzene
could generate biphenyl as by-product due to the high
reactivity of C-Br and C-I bonds. Detail discussion revealed that
the improvement effect of the CH3COONa solution on the
transfer hydrodehalogenation was resulted from the
surfactant-similar effect of CH3COONa and the activation of C-
Cl bond by the dissolved solvated ions. We believed that
saturated aqueous solution of CH3COONa could be applied as a
novel and efficient media in more other organic reactions.
Acknowledgements
24 V. R. Choudhary and C. Samanta, J. Catal., 2006, 238, 28.
25 S. Mukhopadhyay, S. Ratner, A. Spernat, N. Qafisheh and Y.
Sasson, Org. Process Res. Dev., 2002, 6, 297.
The authors thank National Natural Science Foundation of
China (21503016, 21473252) for financial support.
Notes and references
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins