Organic Process Research & Development
Article
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concentrations. The initial rates were determined using a 2 and
3 min residence time.
Representative Procedure for Alcohol Oxidation in
Flow (Heterogeneous Catalyst). The Ru(OH)x/Al2O3 (900
mg) was placed into a 45 cm tube using a slurry (900 mg
Ru(OH)x/Al2O3 + 20 mL acetone). The packed bed was dried
overnight using air. The substrate (30 mmol, 0.15 M) was
prepared as a stock solution in toluene (200 mL) containing
tetradecane (1.96 mL, 10 mmol, 0.05 M) as an internal
standard. The substrate solution was fed into the reactor using
an HPLC pump. The reactor operating procedure was the same
as for the homogeneous catalyst, but with toluene as the
quench solvent.
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AUTHOR INFORMATION
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Corresponding Authors
Noel, T. Org. Lett. 2014, 16, 5800−5803. (q) Su, Y.; Hessel, V.; Noel,
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(8) For examples of liquid phase aerobic oxidation in membrane
reactors, see: (a) Park, C. P.; Kim, D. J. Am. Chem. Soc. 2010, 132,
10102−10106. (b) Tomaszewski, B.; Schmid, A.; Buehler, K. Org.
Process Res. Dev. 2014, 18, 1516−1526. (c) Chaudhuri, S. R.; Hartwig,
J.; Kupracz, L.; Kodanek, T.; Wegner, J.; Kirschning, A. Adv. Synth.
Catal. 2014, 356, 3530−3538. (d) Wu, G.; Constantinou, A.; Cao, E.;
Kuhn, S.; Morad, M.; Sankar, M.; Bethell, D.; Hutchings, G. J.;
Gavriilidis, A. Ind. Eng. Chem. Res. 2015, 54, 4183−4189.
(9) A commercially available tube-in-tube flow reactor is available
from Vapourtec, and has been used in other reactions employing
gaseous reagents. For a representative example of its application to
hydrogenation, see: Mercadante, M. A.; Kelly, C. B.; Lee, C.;
Leadbeater, N. E. Org. Process Res. Dev. 2012, 16, 1064−1068.
(10) For a highlight of recent applications of membrane micro-
Notes
The authors declare no competing financial interest.
ACKNOWLEDGMENTS
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We are grateful to David Mannel for the Ru(OH)x/Al2O3
catalyst and Drs. Anna Davis and William J. Kruper (Dow
Chemical) for helpful discussions. The research was funded by
the Dow Chemical Company. Instrumentation was partially
funded by NSF CHE-1048642.
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