Topics in Catalysis

, Volume 57, Issue 17–20, pp 1505–1511 | Cite as

Hydrogenation of Cinnamaldehyde over Pd/Al2O3 Catalysts Modified with Thiol Monolayers

  • Karl R. Kahsar
  • Stephanie Johnson
  • Daniel K. Schwartz
  • J. Will MedlinEmail author
Original Paper


Modification of supported Pt catalysts with thiols has recently been shown to improve the hydrogenation selectivity of α,β-unsaturated aldehydes to unsaturated alcohols. Here, we apply a variety of organic thiol coatings to Pd/Al2O3 catalysts that typically have a much lower intrinsic selectivity for desired product formation. Thiol monolayers were found to increase hydrogenation selectivity to cinnamyl alcohol; however, unlike with Pt catalysts, the increase was independent of the identity of the organic tail.


Cinnamaldehyde Selective hydrogenation Self-assembled monolayer Palladium platinum Alumina 



This research was supported by the Department of Energy, Office of Science, Basic Energy Sciences Program, Chemical Sciences, Geosciences, and Biosciences Division under Grant Number DE-FG02-10ER16206.


  1. 1.
    Besson M, Gallezot P (2000) Catal Today 57:127CrossRefGoogle Scholar
  2. 2.
    de Jong KP (2009) Synthesis of solid catalysts. Wiley-VCH, DarmstadtCrossRefGoogle Scholar
  3. 3.
    Gallezot P, Richard D (1998) Catal Rev 40:81CrossRefGoogle Scholar
  4. 4.
    Haubrich J, Loffreda D, Delbecq F, Sautet P, Jugnet Y, Krupski A, Becker C, Wandelt K (2008) J Phys Chem C 112:3701CrossRefGoogle Scholar
  5. 5.
    Ponec V (1997) Appl Catal A 149:27CrossRefGoogle Scholar
  6. 6.
    Pham-Huu C, Keller N, Ehret G, Charbonniere LJ, Ziessel R, Ledoux MJ (2001) J Mol Catal A: Chem 170:155CrossRefGoogle Scholar
  7. 7.
    Marshall ST, O’Brien M, Oetter B, Corpuz A, Richards RM, Schwartz DK, Medlin JW (2010) Nat Mater 9:853CrossRefGoogle Scholar
  8. 8.
    Kwon SG, Krylova G, Sumer A, Schwartz MM, Bunel EE, Marshall CL, Chattopadhyay S, Lee B, Jellinek J, Shevchenko EV (2012) Nano Lett 12:5382CrossRefGoogle Scholar
  9. 9.
    Torborg C, Beller M (2009) Adv Synth Catal 351:3027CrossRefGoogle Scholar
  10. 10.
    Wu B, Huang H, Yang J, Zheng N, Fu G (2012) Angew Chem Int Ed 51:3440CrossRefGoogle Scholar
  11. 11.
    Kahsar KR, Schwartz DK, Medlin JW (2012) Appl Catal A 445–446:102CrossRefGoogle Scholar
  12. 12.
    Taguchi T, Isozaki K, Miki K (2012) Adv Mater 24:6462CrossRefGoogle Scholar
  13. 13.
    Schoenbaum CA, Schwartz DK, Medlin JW (2013) J Catal 303:92CrossRefGoogle Scholar
  14. 14.
    Allara DL, Nuzzo RG (1985) Langmuir 1:45CrossRefGoogle Scholar
  15. 15.
    Ulman A (1996) Chem Rev 96:1533CrossRefGoogle Scholar
  16. 16.
    Schwartz DK (2001) Annu Rev Phys Chem 52:107CrossRefGoogle Scholar
  17. 17.
    Kodama C, Hayashi T, Nozoye H (2001) Appl Surf Sci 169–170:264CrossRefGoogle Scholar
  18. 18.
    Love JC, Wolfe DB, Haasch R, Chabinyc ML, Paul KE, Whitesides GM, Nuzzo RG (2003) J Am Chem Soc 125:2597CrossRefGoogle Scholar
  19. 19.
    Ulman A, Eilers JE, Tillman N (1989) Langmuir 5:1147CrossRefGoogle Scholar
  20. 20.
    Petrovykh DY, Kimura-Suda H, Opdahl A, Richter LJ, Tarlov MJ, Whitman LJ (2006) Langmuir 22:2578CrossRefGoogle Scholar
  21. 21.
    Kahsar KR, Schwartz DK, Medlin JW (2013) ACS Catal 3:2041CrossRefGoogle Scholar
  22. 22.
    Kliewer CJ, Bieri M, Somorjai GA (2009) J Am Chem Soc 131:9958CrossRefGoogle Scholar
  23. 23.
    Kahsar KR, Schwartz DK, Medlin JW (2013) J Am Chem Soc 136:520CrossRefGoogle Scholar
  24. 24.
    da Silva AB, Jordão E, Mendes MJ, Fouilloux P (1997) Appl Catal A 148:253CrossRefGoogle Scholar
  25. 25.
    Zhao F, Ikushima Y, Chatterjee M, Shirai M, Arai M (2003) Green Chem 5:76CrossRefGoogle Scholar
  26. 26.
    Haubrich J, Loffreda D, Delbecq F, Sautet P, Jugnet Y, Becker C, Wandelt K (2009) J Phys Chem C 114:1073CrossRefGoogle Scholar
  27. 27.
    Medlin JW (2011) ACS Catal 1:1284CrossRefGoogle Scholar
  28. 28.
    Marshall ST, Horiuchi CM, Zhang WY, Medlin JW (2008) J Phys Chem C 112:20406CrossRefGoogle Scholar
  29. 29.
    Shirai M, Tanaka T, Arai M (2001) J Mol Catal A: Chem 168:99CrossRefGoogle Scholar
  30. 30.
    Delbecq F, Sautet P (1995) J Catal 152:217CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Karl R. Kahsar
    • 1
  • Stephanie Johnson
    • 1
  • Daniel K. Schwartz
    • 1
  • J. Will Medlin
    • 1
    Email author
  1. 1.University of Colorado BoulderBoulderUSA

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