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Green Chemistry
Page 7 of 7
DOI: 10.1039/C8GC01917G
Journal Name
ARTICLE
14 A. Constantinou, G. Wu, A. Corredera, P. Ellis, D. Bethell, G. J.
Hutchings, S. Kuhn and A. Gavriilidis, Org. Process Res. Dev.,
2015, 19, 1973–1979.
15 M. O’Brien, N. Taylor, A. Polyzos, I. R. Baxendale and S. V.
Ley, Chem. Sci., 2011, 2, 1250–1257.
hydrolyzed product in 91% yield continuously, tripling the
hydrogenation productivity without any reaction condition
optimization.
16 A. Polyzos, M. O’Brien, T. P. Petersen, I. R. Baxendale and S.
V. Ley, Angew. Chem. Int. Ed., 2011, 50, 1190–1193.
17 I. Pinnau and L. G. Toy, J. Membr. Sci., 1996, 109, 125–133.
18 P. Bernardo, E. Drioli and G. Golemme, Ind. Eng. Chem. Res.,
2009, 48, 4638–4663.
Conclusion
This work presented the development and experimental
validation of a thin-layer membrane reactor with commonly
used heterogeneous Pd-catalyzed hydrogenations and 19 J. H. Lowry, J. S. Mendlowitz and N. S. (Mani) Subramanian,
Opt. Eng., 1992, 31, 1982–1986.
20 P. R. Resnick and W. H. Buck, in Fluoropolymers 2, Springer,
Boston, MA, 2002, pp. 25–33.
homogeneous Cu(I)/TEMPO aerobic alcohol oxidations. The
unique structure implemented a Teflon AF membrane and
porous carbon cloth in the membrane reactor to separate the
gas from the liquid, simplifying the multiphase hydrodynamics
21 L. Yang and K. F. Jensen, Org. Process Res. Dev., 2013, 17
927–933.
for predictable reactor performance and straightforward scale- 22 J. M. Hoover and S. S. Stahl, J. Am. Chem. Soc., 2011, 133
,
,
,
16901–16910.
23 J. M. Hoover, B. L. Ryland and S. S. Stahl, ACS Catal., 2013,
up. The thin-layer design minimized mass transfer resistance in
gas- liquid systems. Optimizing the carbon cloth thickness
according to the reaction kinetics balanced the trade-off
between reactor manufacturing cost and productivity. Both
3
2599–2605.
24 J. M. Hoover, B. L. Ryland and S. S. Stahl, J. Am. Chem. Soc.,
2013, 135, 2357–2367.
the membrane design and the detailed guidelines for safe 25 X. Ye, M. D. Johnson, T. Diao, M. H. Yates and S. S. Stahl,
Green Chem., 2010, 12, 1180–1186.
26 J. E. Steves, Y. Preger, J. R. Martinelli, C. J. Welch, T. W. Root,
operation of oxygenation reactions provided in this work could
potentially accelerate the adoption of oxygen and hydrogen as
cheap, green reagents in industrial applications. In addition, a
stackable membrane design demonstrated a possible scale-up
strategy.
J. M. Hawkins and S. S. Stahl, Org. Process Res. Dev., 2015, 19
1548–1553.
,
27 J. F. Greene, Y. Preger, S. S. Stahl and T. W. Root, Org.
Process Res. Dev., 2015, 19, 858–864.
28 C.-C. Chen, Ind. Eng. Chem. Res., 2011, 50, 10283–10291.
29 A. M. Polyakov, L. E. Starannikova and Y. P. Yampolskii, J.
Membr. Sci., 2004, 238, 21–32.
30 A. M. Polyakov, L. E. Starannikova and Y. P. Yampolskii, J.
Membr. Sci., 2003, 216, 241–256.
Acknowledgements
We thank the Novartis-MIT Center for Continuous
Manufacturing for financial support.
31 M. H. Al-Dahhan, F. Larachi, M. P. Dudukovic and A. Laurent,
Ind. Eng. Chem. Res., 1997, 36, 3292–3314.
32 V. Holler, D. Wegricht, I. Yuranov, L. Kiwi-Minsker and A.
Renken, Chem. Eng. Amp Technol., 2000, 23, 251–255.
33 N. de Mas, A. Günther, T. Kraus, M. A. Schmidt and K. F.
Jensen, Ind. Eng. Chem. Res., 2005, 44, 8997–9013.
34 M. Al-Rawashdeh, F. Yue, N. G. Patil, T. A. Nijhuis, V. Hessel,
J. C. Schouten and E. V. Rebrov, AIChE J., 2014, 60, 1941–1952.
References
1
C. Yang, A. R. Teixeira, Y. Shi, S. C. Born, H. Lin, Y. L. Song, B.
Martin, B. Schenkel, M. P. Lachegurabi and K. F. Jensen, Green
Chem., 2018, 20, 886–893.
2
D. P. Hruszkewycz, K. C. Miles, O. R. Thiel and S. S. Stahl,
Chem. Sci., 2017, , 1282–1287.
H. P. L. Gemoets, Y. Su, M. Shang, V. Hessel, R. Luque and T.
Noël, Chem. Soc. Rev., 2015, 45, 83–117.
M. O’Brien, I. R. Baxendale and S. V. Ley, Org. Lett., 2010, 12
1596–1598.
J. S. Carey, D. Laffan, C. Thomson and M. T. Williams, Org.
Biomol. Chem., 2006, , 2337–2347.
P. M. Osterberg, J. K. Niemeier, C. J. Welch, J. M. Hawkins, J.
8
3
4
,
5
4
6
R. Martinelli, T. E. Johnson, T. W. Root and S. S. Stahl, Org.
Process Res. Dev., 2015, 19, 1537–1543.
7 T. Tsubogo, H. Oyamada and S. Kobayashi, Nature, 2015,
520, 329–332.
8
9
C. Wiles and P. Watts, Green Chem., 2012, 14, 38–54.
Y. Mo and K. F. Jensen, React. Chem. Eng., 2016, , 501–507.
1
10 A. Adamo, R. L. Beingessner, M. Behnam, J. Chen, T. F.
Jamison, K. F. Jensen, J.-C. M. Monbaliu, A. S. Myerson, E. M.
Revalor, D. R. Snead, T. Stelzer, N. Weeranoppanant, S. Y. Wong
and P. Zhang, Science, 2016, 352, 61–67.
11 J. Imbrogno, L. Rogers, D. A. Thomas and K. F. Jensen, Chem.
Commun., 2017, 54, 70–73.
12 Y. Mo, H. Lin and K. F. Jensen, Chem. Eng. J., 2018, 335, 936–
944.
13 N. Zaborenko, R. J. Linder, T. M. Braden, B. M. Campbell, M.
M. Hansen and M. D. Johnson, Org. Process Res. Dev., 2015, 19
1231–1243.
,
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