Applied Chemistry for Engineering (공업화학)

The Korean Society of Industrial and Engineering Chemistry (한국공업화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis of Pd-Ag on Charcoal Catalyst for Aerobic Benzyl Alcohol Oxidation Using [Hmim][PF6]

[Hmim][PF6]를 사용한 벤질 알코올의 호기성 산화반응용 팔라듐-은 차콜 촉매 제조

  • Choo, Yunjun (Department of Chemical & Biomolecular Engineering, Seoul National University of Science & Technology) ;
  • Yoo, Kye Sang (Department of Chemical & Biomolecular Engineering, Seoul National University of Science & Technology)
  • 추연준 (서울과학기술대학교 화공생명공학과) ;
  • 유계상 (서울과학기술대학교 화공생명공학과)
  • Received : 2014.06.20
  • Accepted : 2014.07.14
  • Published : 2014.08.10
Download PDF
⟨ Previous Next ⟩

Abstract

Pd on charcoal particles were prepared by wet impregnation to develop commercial catalyst for aerobic benzyl alcohol oxidation. Especially, one of room temperature ionic liquids, [Hmim][$PF_6$], was used as an effective solvent in the synthesis to improve the metal dispersion of the catalysts. Among the Pd/Charcoal with various Pd concentrations, 7.5 wt% catalyst showed the higher catalytic activity and stability. Moreover, Ag was used as a promoter with various ratios in catalyst preparation. Under identical reaction conditions, the catalyst with 9 : 1 of Pd and Ag weight ratios was most active due to higher metal dispersion.

호기성 벤질 알코올 산화반응용 상용촉매 개발을 위하여 팔라듐이 담지된 차콜 입자를 제조하였다. 특히 촉매의 팔라듐 분산도를 높이기 위해서 상온 이온성액체 중 하나인 [Hmim][$PF_6$]을 기능성 용매로 사용하여 입자를 합성하였다. 다양한 농도의 팔라듐을 함침하여 제조된 입자의 반응성을 측정한 결과 7.5 wt%의 촉매가 가장 우수한 반응 활성과 안정성을 나타내었다. 또한 조촉매로서 다양한 농도의 은입자를 합침하여 촉매를 제조하였다. 동일한 반응조건에서 팔라듐과 은의 질량 비율이 9 : 1인 촉매가 높은 금속 분산도로 인하여 가장 반응성이 우수하였다.

Keywords

References

  1. R. A. Sheldon, I. Arends, and A. Dijksman, New developments in catalytic alcohol oxidations for fine chemicals synthesis, Catal. Today, 57, 157-166 (2000). https://doi.org/10.1016/S0920-5861(99)00317-X
  2. R. A. Sheldon, I. W. C. E. Arends, G. J. T. Brink, and A. Dijksman, Green, catalytic oxidations of alcohols, Acc. Chem. Res., 35, 774-781 (2002). https://doi.org/10.1021/ar010075n
  3. R. A. Sheldon and J. K. Kochi, Metal-catalyzed oxidation of organic compounds, Academic Press, New York (1981).
  4. R. V. Stevens, K. T. Chapman, and H. N. Weller, Convenient and inexpensive procedure for oxidation of secondary alcohols to ketones, J. Org. Chem., 45, 2030-2032 (1980). https://doi.org/10.1021/jo01298a066
  5. J. R. Holum, Study of the chromium (VI) oxide-pyridine complex, J. Org. Chem., 26, 4814-4816 (1961). https://doi.org/10.1021/jo01070a009
  6. D. G. Lee and U. A. Spitzer, Aqueous dichromate oxidation of primary alcohols, J. Org. Chem., 35, 3589-3590 (1970). https://doi.org/10.1021/jo00835a101
  7. R. J. Highet and W. C. Wildman, Solid manganese dioxide as an oxidizing agent, J. Am. Chem. Soc., 77, 4399-4401 (1955). https://doi.org/10.1021/ja01621a062
  8. F. M. Menger and C. Lee, Synthetically useful oxidations at solid sodium permanganate surfaces, Tetrahedron Lett., 22, 1655-1656 (1981). https://doi.org/10.1016/S0040-4039(01)90402-2
  9. K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda, Creation of a monomeric Ru species on the surface of hydroxyapatite as an efficient heterogeneous catalyst for aerobic alcohol oxidation, J. Am. Chem. Soc., 122, 7144-7145 (2000). https://doi.org/10.1021/ja001325i
  10. T. Nishimura, T. Onoue, K. Ohe, and S. Uemura, Palladium (II)-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen, J. Org. Chem., 64, 6750-6755 (1999). https://doi.org/10.1021/jo9906734
  11. M. Hasan, M. Musawir, P. N. Davey, and I. V. Kozhevnikov, Oxidation of primary alcohols to aldehydes with oxygen catalysed by tetra-n-propylammonium perruthenate, J. Mol. Catal. A Chem., 180, 77-84 (2002). https://doi.org/10.1016/S1381-1169(01)00410-1
  12. K. Mori, T. Hara, T. Mizugaki, K. Ebitani, and K. Kaneda, Hydroxyapatite-supported palladium nanoclusters: a highly active heterogeneous catalyst for selective oxidation of alcohols by use of molecular oxygen, J. Am. Chem. Soc., 126, 10657-10666 (2004). https://doi.org/10.1021/ja0488683
  13. A. Abad, P. Concepcion, A. Corma, and H. Garcia, A collaborative effect between gold and a support induces the selective oxidation of alcohols, Angew. Chem. Int. Ed., 44, 4066-4069 (2005). https://doi.org/10.1002/anie.200500382
  14. W. Liu and M. Flytzani-Stephanopoulos, Cu-and Ag-modified cerium oxide catalysts for methane oxidation, J. Catal., 153, 304-316 (1995). https://doi.org/10.1006/jcat.1995.1132
  15. A. Arcadi and S. Di Giuseppe, Recent applications of gold catalysis in organic synthesis, Curr. Org. Chem., 8, 795-812 (2004). https://doi.org/10.2174/1385272043370564
  16. Z. Q. Tian, B. Ren, and D. Y. Wu, Surface-enhanced Raman scattering: from noble to transition metals and from rough surfaces to ordered nanostructures, J. Phys. Chem. B., 106, 9463-9483 (2002).
  17. P. Vonmatt and A. Pfaltz, Chiral phosphinoaryldihydrooxazoles as ligands in asymmetric catalysis: Pd catalyzed allylic substitution, Angew. Chem. Int. Ed., 32, 566-568 (1993). https://doi.org/10.1002/anie.199305661
  18. D. Astruc, F. Lu, and J. R. Aranzaes, Nanoparticles as recyclable catalysts: the frontier between homogeneous and heterogeneous catalysis, Angew. Chem. Int. Ed., 44, 7852-7872 (2005). https://doi.org/10.1002/anie.200500766
  19. M. Fernandez-Garcia, A. Martinez-Arias, L. N. Salamanca, J. M. Coronado, J. A. Anderson, J. C. Conesa, and J. Soria, Influence of ceria on Pd activity for the CO + $O_2$ reaction, J. Catal., 187, 474-485 (1999). https://doi.org/10.1006/jcat.1999.2624
  20. Y. Nishihata, J. Mizuki, T. Akao, H. Tanaka, M. Uenishi, M. Kimura, T. Okamoto, and N. Hamada, Self-regeneration of a Pd-perovskite catalyst for automotive emissions control, Nature, 418, 164-167 (2002). https://doi.org/10.1038/nature00893
  21. J. M. Thomas, B. F. G. Johnson, R. Raja, G. Sankar, and P. A. Midgley, High-performance nanocatalysts for single-step hydrogenations, Acc. Chem. Res., 36, 20-30 (2003). https://doi.org/10.1021/ar990017q
  22. R. Narayanan and M. A. El-Sayed, Shape-dependent catalytic activity of platinum nanoparticles in colloidal solution, Nano Lett., 4, 1343-1348 (2004). https://doi.org/10.1021/nl0495256
  23. S. E. Habas, H. Lee, V. Radmilovic, G. A. Somorjai, and P. Yang, Shaping binary metal nanocrystals through epitaxial seeded growth, Nat. Mater., 6, 692-697 (2007). https://doi.org/10.1038/nmat1957
  24. K. M. Bratlie, H. Lee, K. Komvopoulos, P. Yang, and G. A. Somorjai, Platinum nanoparticle shape effects on benzene hydrogenation selectivity, Nano Lett., 7, 3097-3101 (2007). https://doi.org/10.1021/nl0716000
  25. C. Wang, H. Daimon, T. Onodera, T. Koda, and S. Sun, A general approach to the size-and shape-controlled synthesis of platinum nanoparticles and their catalytic reduction of oxygen, Angew. Chem, Int. Ed., 47, 3588-3591 (2008). https://doi.org/10.1002/anie.200800073
  26. P. Wasserscheid and W. Keim, Ionic liquids-new "Solutions" for transition metal catalysis, Angew. Chem. Int. Ed., 39, 3773-3789 (2000).
  27. T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev., 99, 2071-2084 (1999). https://doi.org/10.1021/cr980032t
  28. J. B. Jeong and K. S. Yoo, Development of hexafluoropropylene hydrogenation with Pd/C particles prepared with 1-hexyl-3-methylimidazolium tetrafluoroborate, Appl. Chem. Eng., 24, 412-415 (2013).