ChemCatChem
10.1002/cctc.201601637
FULL PAPER
5
50°C for 2 hours. Subsequently, it was cooled down to 50°C and then
[16]
D. P. Debecker, M. Stoyanova, F. Colbeau-Justin, U. Rodemerck, C.
Boissiãre, E. M. Gaigneaux, C. Sanchez, Angew. Chemie - Int. Ed.
-
1
-
exposed to a gaz mixture of 5% NH
3
in He (10 ml.min ) and Ar (20 ml.min
2012, 51, 2129–2131.
1
was removed by purging with Ar (30 ml.min-
)
)
for 45 min. Physisorbed NH
at 50°C for 90 min. The TPD measurement was conducted by heating
3
[
17]
F. Colbeau-Justin, C. Boissière, A. Chaumonnot, A. Bonduelle, C.
Sanchez, Adv. Funct. Mater. 2014, 24, 233–239.
D. P. Debecker, M. Stoyanova, U. Rodemerck, F. Colbeau-Justinc,
C. Boissère, A. Chaumonnot, A. Bonduelle, C. Sanchez, Appl. Catal.
A Gen. 2014, 470, 458–466.
1
-
1
the sample from 50 to 650°C with ramping rate of 5°C.min . Desorbed NH
was detected by a mass spectrometer (QGA model).
3
[18]
Production of ethyl lactate from dihydroxyacetone
[19]
[20]
M. Pagliaro, R. Ciriminna, H. Kimura, M. Rossi, C. Della Pina, Angew.
Chemie - Int. Ed. 2007, 46, 4434–4440.
S. Hirasawa, Y. Nakagawa, K. Tomishige, A. Corma, S. Iborra, A.
Velty, P. Gallezot, M. Schlaf, R. M. West, E. L. Kunkes, et al., Catal.
Sci. Technol. 2012, 2, 1150.
G. M. Lari, C. Mondelli, J. Pérez-Ramírez, ACS Catal. 2015, 5, 1453–
1461.
A. Villa, S. Campisi, C. E. Chan-Thaw, D. Motta, D. Wang, L. Prati,
Catal. Today 2015, 249, 103–108.
G.-Y. Yang, S. Shao, Y.-H. Ke, C.-L. Liu, H.-F. Ren, W.-S. Dong, RSC
Adv. 2015, 5, 37112–37118.
M. Dusselier, P. Van Wouwe, A. Dewaele, E. Makshina, B. F. Sels,
Energy Environ. Sci. 2013, 6, 1415–1442.
J. Coombs, K. Hall, Renew. Energy 1998, 15, 54–59.
R. A. Gross, B. Kalra, C. Bastoli, R. A. Gross, J.-D. Gu, D. Eberiel, S.
P. McCarthy, C. M. Buchanan, B. G. Pearcy, A. W. White, et al.,
Science 2002, 297, 803–7.
L.-T. Lim, R. Auras, M. Rubino, Prog. Polym. Sci. 2008, 33, 820–852.
E. Bang, J. Eriksen, L. Mønsted, O. Mønsted, Acta Chem. Scand.
The catalytic tests were performed in batch mode using a reflux apparatus.
In a typical experiment for the conversion of dihydroxyacetone (DHA) to
ethyl lactate (EL), 540 mg of DHA (6 mmol, in the form of 1,3-
dihydroxyacetone dimer) and 75 mg of nonane (0.58 mmol, as GC internal
standard) were dissolved in 11.76 g of absolute ethanol (as solvent and
reactant) at 45 °C for 30 min. Then, the selected amount of catalyst was
added to the solution at room temperature. The reaction mixture was
heated at 90 °C under vigorous stirring (1200 rpm) for the selected reaction
time. At the end of the test, the catalyst was separated by centrifugation
and the solution was analysed by gas chromatography (GC) on a Trace
GC Ultra from Interscience. Recycling tests were performed by separating
the catalyst from the reaction mixture by centrifugation followed by
washing with ethanol (2 x 10mL). Finally, the catalyst was dried overnight
at 100 °C. The catalyst was finally calcined in air at 500 °C for 2h (heating
rate 2 °C/ min). Leaching tests were carried out under the general reaction
conditions employed for the catalytic tests (vide supra). The catalyst was
removed from the reaction mixture after 30 min by centrifugation, followed
by hot filtration at the same temperature used for the catalytic test. The
filtrate was allowed to react for another 5 h 30 min. The products were
analysed by GC both after 1 h and at the end of the test (6h).
[
21]
[22]
[
[
23]
24]
[
[
25]
26]
[27]
[28]
1
994, 48, 12–19.
J. Eriksen, O. Mønsted, L. Mønsted, Transition. Met. Chem. 1998, 23,
83–787.
[
29]
7
[30]
[31]
Y. Hayashi, Y. Sasaki, Chem. Commun. (Camb). 2005, 2716–2718.
P. P. Pescarmona, K. P. F. Janssen, C. Delaet, C. Stroobants, K.
Houthoofd, A. Philippaerts, C. De Jonghe, J. S. Paul, P. A. Jacobs,
B. F. Sels, Green Chem. 2010, 12, 1083–1089.
[
[
32]
33]
X. Collard, P. Louette, S. Fiorilli, C. Aprile, Phys. Chem. Chem. Phys.
2015, 17, 26756–26765.
X. Collard, L. Li, W. Lueangchaichaweng, A. Bertrand, C. Aprile, P.
P. Pescarmona, Catal. Today 2014, 235, 184–192.
Acknowledgements
[34]
a) L. Li, C. Stroobants, K. Lin, P. A. Jacobs, B. F. Sels, P. P.
Pescarmona, Green Chem. 2011, 13, 1175–1181; b) L. Li, D. Cani,
P. P. Pescarmona, Inorganica Chim. Acta 2015, 431, 289–296.
P. Y. Dapsens, C. Mondelli, J. Pérez-Ramirez, Chem. Soc. Rev. 2015,
Authors acknowledge the ‘Communauté française de Belgique’
for the financial support – including the PhD fellowship of A. Vivian
[
35]
44, 7025-7043.
–
through the ARC programme (15/20-069). F. Devred is
[36]
F. De Clippel, M. Dusselier, R. Van Rompaey, P. Vanelderen, J.
Dijkmans, E. Makshina, L. Giebeler, S. Oswald, G. V. Baron, J. F. M.
Denayer, et al., J. Am. Chem. Soc. 2012, 134, 10089–10101.
K. Chaudhari, T. K. Das, P. R. Rajmohanan, K. Lazar, S. Sivasanker,
A. J. Chandwadkar, J. Catal. 1999, 183, 281–291.
E. A. Alarcón, A. L. Villa, C. M. de Correa, Microporous Mesoporous
Mater. 2009, 122, 208–215.
R. Bermejo-Deval, R. Gounder, M. E. Davis, ACS Catal. 2012, 2,
acknowledged for the technical and logistical support.
[
[
[
37]
38]
39]
Keywords: mesoporous mixed oxide • sol-gel chemistry • EISA
•
spray drying • ethyl lactate
2705–2713.
References
[40]
P. Mulvaney, F. Grieser, D. Meisel, Langmuir 1990, 6, 567–572.
M. Luhmer, J. B. D’Espinose, H. Hommel, A. P. Legrand, Magn.
Reson. Imaging 1996, 14, 911–913.
M. Renz, T. Blasco, A. Corma, V. Fornés, R. Jensen, L. Nemeth,
Chem. - A Eur. J. 2002, 8, 4708–4717.
N. Kishor Mal, V. Ramaswamy, S. Ganapathy, A. V. Ramaswamy,
Appl. Catal. A, Gen. 1995, 125, 233–245.
P. Shah, A. V. Ramaswamy, K. Lazar, V. Ramaswamy, Microporous
Mesoporous Mater. 2007, 100, 210–226.
P. Y. Bruice, Organic Chemistry, Pearson Prentice Hall, 2007.
a) X. Yang, L. Wu, Z. Wang, J. Bian, T. Lu, L. Zhou, C. Chen, J. Xu,
Catal. Sci. Technol. 2016, 6, 1757-1763 ; b) E. Taarning, S.
Saravanamurugan, M. Spangsberg Holm, J. Xiong, R. M. West, C. H.
Christensen, ChemSusChem 2009, 2, 625-627.
[
[
[
[
41]
42]
43]
44]
[
[
1]
2]
G. Busca in Heterogeneous Catalytic Materials, Ch. 6, Elsevier, 2014,
pp. 103–195.
C. T. Kresge, M. E. Leonowicz, W. J. Roth, J. C. Vartuli, J. S. Beck,
Nature 1992, 359, 710–712.
[
[
3]
4]
N. Pal, A. Bhaumik, RSC Adv. 2015, 5, 24363–24391.
G. J. D. A. A. Soler-Illia, C. Sanchez, B. Lebeau, J. Patarin, Chem.
Rev. 2002, 102, 4093–4138.
[
[
45]
46]
[
[
5]
6]
P. Yang, Science (80-. ) 1998, 282, 2244–2246.
D. P. Debecker, C. Boissière, G. Laurent, S. Huet, P. Eliaers, C.
Sanchez, R. Backov, Chem. Commun. 2015, 51, 14018–21.
S. K. Jana, H. Takahashi, M. Nakamura, M. Kaneko, R. Nishida, H.
Shimizu, T. Kugita, S. Namba, Appl. Catal. A Gen. 2003, 245, 33–41.
Y. Jiang, Y. Zhao, X. Xu, K. Lin, D. Wang, RSC Adv. 2016, 6, 77481–
[
[
[
[
7]
[
47]
C. Cossement, J. Darville, J. M. Gilles, J. B. Nagy, C. Fernandez, J.
P. Amoureux, Magn. Reson. Chem.1992, 30(3), 263-270.
8]
77488.
9]
K. Lin, O. I. Lebedev, G. Vana Tendeloo, P. A. Jacobs, P. P.
Pescarmona, Chem. - A Eur. J. 2010, 16, 13509–13518.
D. P. Debecker, B. Schimmoeller, M. Stoyanova, C. Poleunis, P.
Bertrand, U. Rodemerck, E. M. Gaigneaux, J. Catal. 2011, 277, 154–
10]
163.
[
[
[
[
[
11]
12]
13]
14]
15]
R. Bermejo-Deval, M. Orazov, R. Gounder, S. J. Hwang, M. E. Davis,
ACS Catal. 2014, 4, 2288–2297.
S. Tolborg, I. Sádaba, C. M. Osmundsen, P. Fristrup, M. S. Holm, E.
Taarning, ChemSusChem 2015, 8, 613–617.
L. Li, X. Collard, A. Bertrand, B. F. Sels, P. P. Pescarmona, C. Aprile,
J. Catal. 2014, 314, 56–65.
C. Boissiere, D. Grosso, A. Chaumonnot, L. Nicole, C. Sanchez, Adv.
Mater. 2011, 23, 599–623.
Y. Lu, H. Fan, A. Stump, T. L. Ward, T. Rieker, C. J. Brinker, Nature
1999, 398, 223–226.
This article is protected by copyright. All rights reserved.