Synlett 2013; 24(17): 2225-2228
DOI: 10.1055/s-0033-1339798
letter
© Georg Thieme Verlag Stuttgart · New York

Micro and Nanobubble Based Strategy for Gas–Liquid–Solid Multiphase Reactions: Palladium-Catalysed Hydrogenation of Carbon–Carbon Unsaturated Bonds

Nobuyuki Mase*
Department of Applied Chemistry and Biochemical Engineering, Graduate School of Engineering, and Green Energy Research Division, Research Institute of Green Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan   Fax: +81(53)4781196   Email: tnmase@ipc.shizuoka.ac.jp
,
Shogo Isomura
Department of Applied Chemistry and Biochemical Engineering, Graduate School of Engineering, and Green Energy Research Division, Research Institute of Green Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan   Fax: +81(53)4781196   Email: tnmase@ipc.shizuoka.ac.jp
,
Mitsuo Toda
Department of Applied Chemistry and Biochemical Engineering, Graduate School of Engineering, and Green Energy Research Division, Research Institute of Green Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan   Fax: +81(53)4781196   Email: tnmase@ipc.shizuoka.ac.jp
,
Naoharu Watanabe
Department of Applied Chemistry and Biochemical Engineering, Graduate School of Engineering, and Green Energy Research Division, Research Institute of Green Science and Technology, Shizuoka University, 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan   Fax: +81(53)4781196   Email: tnmase@ipc.shizuoka.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 05 August 2013

Accepted after revision: 22 August 2013

Publication Date:
30 September 2013 (online)


Abstract

An autoclave-free, gas–liquid–solid multiphase hydrogenation of carbon–carbon unsaturated bonds using hydrogen micro and nanobubbles (MNBs) is developed. The process allows the liquid phase of the reaction mixture to maintain a high concentration of hydrogen gas.

Supporting Information

 
  • References

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  • 5 Typical procedure for the hydrogenation of unsaturated carbon–carbon bonds using the H2-MNB strategy. The hydrogenation was carried out in a 100 mL vial equipped with an MNB generator without additional stirring. Alkene or alkyne 1 (20 mmol) was dissolved in MeOH (80 mL) and the soln warmed to 30 °C. Using the MNB generator (MA3-FS), H2-MNBs were introduced into the reactor in the presence of palladium on alumina spheres (Pd/Al2O3) (0.5% Pd, 2–4 mm, 0.1 mmol, 0.5 mol%) at a H2 flow rate of 5 mL/min. Aliquots were taken from the mixture periodically to monitor the reaction progress using GC analysis. After the completion of the hydrogenation reaction, the MeOH was evaporated in vacuo to afford the desired alkane 1 in excellent purity. We further examined the hydrogenation of styrene (1a) in the presence of the following heterogeneous catalysts: 5% Pd/C, 5% Pd/C E type, 5% Pd/C NX type, 5% Pd/C K type and 2.7 wt% Pd/C spheres, however, increasing back pressure then clogging of the flow system occurred during operation.
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  • 7 The preliminary results were discussed at the 42nd Annual Meeting of the Union of Chemistry-Related Societies in Chubu Area, Nagano, Japan, 2011, 1P-08.
  • 8 Preliminary experimental determinations of the average size (158 nm) and concentration (0.27 × 108 particles/mL) of H2 nanobubbles using the MA3-FS generator were performed using a NanoSight LM10-HS. On the other hand, no formation of H2 nanobubbles was observed under standard bubbling or balloon conditions.