Green Chemistry
Paper
M. Micušik, Appl. Catal., A, 2013, 468, 426; (e) X. L. Li,
J. Deng, T. Pan, C. G. Yu, H. J. Xu and Y. Fu, Green Chem.,
2015, 17, 1038; (f) H. Y. Zhu, M. H. Zhou, Z. Zeng,
G. M. Xiao and R. Xiao, Korean J. Chem. Eng., 2014, 31, 593;
(g) C. Y. Liu, R. P. Wei, G. L. Geng, M. H. Zhou, L. J. Gao
that, as a consequence of the undesired decarbonylation
pathway that occurred under the conditions of the
standard assay, a trace amount of the resultant CO can
severely restrict the ability of PGM-based catalysts to
initiate FFA conversion.
and G. M. Xiao, Fuel Process. Technol., 2015, 134, 168; 12 (a) A. Kulkarni and B. Török, Curr. Org. Synth., 2011, 8, 187;
(h) R. Q. Fang, H. L. Liu, R. Luque and Y. W. Li, Green
Chem., 2015, 17, 4183; (i) M. Hronec, K. Fulajtárová,
I. Vávra, T. Soták and E. Dobročka, Appl. Catal., B, 2016,
181, 210.
(b) M. Irfan, T. N. Glasnov and C. O. Kappe, ChemSusChem,
2011, 4, 300; (c) J. Pritchard, G. A. Filonenko, R. van Putten,
E. J. M. Hensen and E. A. Pidko, Chem. Soc. Rev., 2015, 44,
3808.
5 (a) M. Renz, Eur. J. Org. Chem., 2005, 979; 13 Selected examples of recent reports using TiO2 as an
(b) O. Nagashima, S. Sato, R. Takahashi, T. Sodesawa and
T. Akashi, Appl. Catal., A, 2006, 312, 175; (c) P. Sudarsanam,
L. Katta, G. Thrimurthulu and B. M. Reddy, J. Ind. Eng.
Chem., 2013, 19, 1517; (d) M. Hronec, K. Fulajtarová,
T. Liptaj, M. Štolcová, N. Prónayová and T. Soták, Biomass
Bioenergy, 2014, 63, 291; (e) J. F. Yang, N. Li, G. Y. Li,
W. T. Wang, A. Q. Wang, X. D. Wang, Y. Cong and T. Zhang,
Chem. Commun., 2014, 50, 2572.
efficient water-compatible heterogeneous Lewis acid cata-
lyst: (a) K. Nakajima, R. Noma, M. Kitano and M. Hara,
J. Phys. Chem. C, 2013, 117, 16028; (b) R. Noma, K. Nakajima,
K. Kamata, M. Kitano, S. Hayashi and M. Hara, J. Phys.
Chem. C, 2015, 119, 17117; (c) H. Hirakawa, M. Katayama,
Y. Shiraishi, H. Sakamoto, K. L. Wang, B. Ohtani,
S. Ichikawa, S. Tanaka and T. Hirai, ACS Appl. Mater. Inter-
faces, 2015, 7, 3797.
6 (a) G. Piancatelli, A. Scettri, G. David and M. Dauria, Tetra- 14 (a) J. Oliver-Meseguer, J. R. Cabrero-Antoniono,
hedron, 1978, 34, 2775; (b) O. N. Faza, C. S. López,
R. Álvarez and Á. R. de Lera, Chem. – Eur. J., 2004, 10, 4324;
(c) G. K. Veits, D. R. Wenz and J. R. de Alaniz, Angew.
Chem., Int. Ed., 2010, 49, 9484; (d) M. Masayoshi, US Patent,
4970345, 1990.
7 (a) C. Mohr, H. Hofmeister, J. Radnik and P. Claus, J. Am.
Chem. Soc., 2003, 125, 1905; (b) A. Corma and P. Serna,
Science, 2006, 313, 332; (c) A. Negoi, S. Wuttke, E. Kemnitz,
I. Domínguez, A. Leyva-Pérez and A. Corma, Science, 2012,
338, 1452; (b) M. C. B. Jaimes, C. R. N. Böhling,
J. M. Serrano-Becerra and A. S. K. Hashmi, Angew. Chem.,
Int. Ed., 2013, 52, 7963.
15 (a) K. Weissermel and H.-J. Arpe, Industrial Organic
Chemistry, Wiley-VCH, Weinheim, 2003; (b) A. Castellan,
J. C. J. Bart and S. Cavallaro, Catal. Today, 1991, 9,
237.
D. Macovei, V. I. Parvulescu, C. M. Teodorescu and 16 (a) K. Sato, M. Aoki and R. Noyori, Science, 1998, 281, 1646;
S. M. Coman, Angew. Chem., Int. Ed., 2010, 49, 8134;
(d) G. Li, C. Zeng and R. Jin, J. Am. Chem. Soc., 2014, 136,
3673.
(b) S. O. Lee, R. Raja, K. D. M. Harris, J. M. Thomas,
B. F. G. Johnson and G. Sankar, Angew. Chem., Int. Ed.,
2003, 42, 1520; (c) S. Van de Vyver and Y. Román-Leshkov,
Catal. Sci. Technol., 2013, 3, 1465.
8 (a) L. He, L. C. Wang, H. Sun, J. Ni, Y. Cao, H. Y. He and
K. N. Fan, Angew. Chem., Int. Ed., 2009, 48, 9538; (b) D. Ren, 17 (a) T. Polen, M. Spelberg and M. Bott, J. Biotechnol., 2013,
L. He, R. L. S. Ding, Y. M. Liu, Y. Cao, H. Y. He and
K. N. Fan, J. Am. Chem. Soc., 2012, 134, 17592; (c) X. Liu,
167, 75; (b) R. Beerthuis, G. Rothenberg and N. R. Shiju,
Green Chem., 2015, 17, 1341.
L. He, Y. M. Liu and Y. Cao, Acc. Chem. Res., 2014, 47, 793; 18 (a) J. Bian, M. Xiao, S. J. Wang, Y. X. Lu and Y. Z. Meng,
(d) S. S. Li, X. Liu, Y. M. Liu, H. Y. He, K. N. Fan and
Y. Cao, Chem. Commun., 2014, 50, 5626; (e) X. Liu, H. Q. Li,
S. Ye, Y. M. Liu, H. Y. He and Y. Cao, Angew. Chem., Int. Ed.,
2014, 53, 7624; (f) L. Yu, Q. Zhang, S. S. Li, J. Huang,
Y. M. Liu, H. Y. He and Y. Cao, ChemSusChem, 2015, 8,
3029.
Catal. Commun., 2009, 10, 1142; (b) D. Ballivet-Tkatchenko,
F. Bernard, F. Demoisson, L. Plasseraud and
S. R. Sanapureddy, ChemSusChem, 2011, 4, 1316;
(c) A. Bansode and A. Urakawa, ACS Catal., 2014, 4,
3877.
19 (a) H. X. Mai, L. D. Sun, Y. W. Zhang, R. Si, W. Feng,
H. P. Zhang, H. C. Liu and C. H. Yan, J. Phys. Chem. B,
2005, 109, 24380; (b) J. L. He, T. Xu, Z. H. Wang,
Q. H. Zhang, W. P. Deng and Y. Wang, Angew. Chem., Int.
Ed., 2012, 51, 2438.
9 J. Ohyama, R. Kanao, A. Esakia and A. Satsuma, Chem.
Commun., 2014, 50, 5633.
10 An evaluation of the acidic properties by NH3-temperature-
programmed desorption (NH3-TPD, Fig. S2†) coupled with
IR spectroscopic measurement of adsorbed pyridine 20 Although we are aware that there is one precedent of sub-
(Fig. S3†) revealed that TiO2-A possesses only mild Lewis
acidic sites with a much lower population density as com-
pared to other supports, thus verifying the distinguished
bifunctional character of the Au/TiO2-A catalyst.
jecting the CPO–DMC mixture to MgO, we emphasize that
in this case only a modest yield (<40%) of DAP was attain-
able: (a) D. D. Wu, Z. Chen, Z. B. Jia and L. Shuai, Sci.
China: Chem., 2012, 55, 380.
11 We have confirmed in a set of separate experiments that 21 (a) X. Zhang, H. Shi and B. Q. Xu, Angew. Chem., Int. Ed.,
the TiO2-A supported Pt and Pd NPs exhibited much
higher intrinsic FFA hydrogenation activity than Au/TiO2-A
at 80 °C (Table S3†). It is therefore reasonable to assume
2005, 44, 7132; (b) X. L. Du, L. He, S. Zhao, Y. M. Liu,
Y. Cao, H. Y. He and K. N. Fan, Angew. Chem., Int. Ed.,
2011, 50, 7815; (c) Q. Y. Bi, X. L. Du, Y. M. Liu, Y. Cao,
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Green Chem.