화학공학소재연구정보센터
홈 로그인 로그아웃 연락처 사이트맵
Journal of Industrial and Engineering Chemistry, Vol.46, 279-288, February, 2017
DOI10.1016/j.jiec.2016.10.040  Export Citation
Interconnected ruthenium dioxide nanoparticles anchored on graphite oxide: Highly efficient candidate for solvent-free oxidative synthesis of imines
Guohao Yuan, Mayakrishnan Gopiraman1, †, Hyung Joon Cha2, Hwang Dong Soo3, Ill-Min Chung1, and Ick Soo Kim†
  • Nano Fusion Technology Research Group, Division of Frontier Fibers, Institute for Fiber Engineering (IFES), Interdisciplinary Cluster for Cutting Edge Research (ICCER), Shinshu University, Tokida 3-15-1, Ueda, Nagano Prefecture 386-8567, Japan
  • 1Department of Applied Bioscience, College of Life & Environment Science, Konkuk University, 120 Neungdong-ro, Gwangjin-gu, Seoul 05029, South Korea
  • 2Department of Chemical Engineering, Pohang University of Science and Technology, Pohang 790-784, South Korea
  • 3Integrative Biosciences and Biotechnology, Pohang University of Science and Technology, Pohang 790-784, South Korea
E-mail:,
Interconnected ruthenium dioxide nanoparticles (RuO2NPs) anchored graphite oxide nanocatalyst (RuO2/GO) with good BET surface-area (285 m2/g) was prepared. Under feasible reaction conditions, the RuO2/GO worked well for oxidative synthesis of imines. The RuO2/GO catalyzed a broad range of amines including less reactive aliphatic amines in good yields (98.58%) with excellent selectivity (100%). This is the most efficient RuO2-based nanocatalyst for the synthesis of imines among those reported to date. An indirect two-step method was adopted for the coupling of alcohols and amines, and the results found to be excellent. The reusability, stability and heterogeneity of RuO2/GO were also investigated.
Keywords:Graphite oxide;Ruthenium dioxide;Nanocatalyst;Imines;Coupling reactions
  1. Monopoli A, Cotugno P, Iannone F, Ciminale F, Dell-Anna MM, Mastrorilli P, Nacci A, Eur. J. Org. Chem., 27, 5925 (2014)
  2. Biswas S, Dutta B, Mullick K, Kuo CH, Poyraz AS, Suib S, ACS Catal., 5, 4394 (2015)
  3. Kobayashi S, Mori Y, Fossey JS, Salter MM, Chem. Rev., 111(4), 2626 (2011)
  4. Chen B, Wang L, Gao S, ACS Catal., 5, 5851 (2015)
  5. Naeimi H, Salimi F, Rabiei K, J. Mol. Catal. A-Chem., 260(1-2), 100 (2006)
  6. Ryland BL, Stahl S, Angew. Chem.-Int. Edit., 53, 8824 (2014)
  7. Patil RD, Adimurthy S, RSC Adv., 2, 5119 (2012)
  8. Perez JM, Cano R, Yus M, Ramon DJ, Eur. J. Org. Chem., 2012, 4548 (2012)
  9. Al-Hmoud L, Jones CW, J. Catal., 301, 116 (2013)
  10. Dhakshinamoorthy A, Alvaro M, Garcia H, ChemCatChem, 2, 1438 (2010)
  11. Qiu X, Len C, Luque R, Li Y, ChemSusChem, 7, 1684 (2014)
  12. Chu G, Li C, Org. Biomol. Chem., 8, 4716 (2010)
  13. Rao BG, Sudarsanam P, Rangaswamy A, Reddy BM, Catal. Lett., 145(7), 1436 (2015)
  14. Ahmad S, Gopalaiah K, Chandrudu SN, Nagarajan R, Inorg. Chem., 53(4), 2030 (2014)
  15. Zhang Z, Wang F, Wang M, Xu S, Chen H, Zhang C, Xu J, Green Chem., 16, 2523 (2014)
  16. Biswas S, Dutta B, Mullick K, Kuo CH, Poyraz AS, Suib SL, ACS Catal., 5, 4394 (2015)
  17. Kwon MS, Kim S, Park S, Bosco W, Chidrala RK, Park J, J. Org. Chem., 74, 2877 (2009)
  18. Cui W, Zhaorigetu B, Jia M, Ao W, Zhu H, RSC Adv., 4, 2601 (2014)
  19. Zhu BL, Lazar M, Trewyn BG, Angelici RJ, J. Catal., 260(1), 1 (2008)
  20. Aschwanden L, Mallat T, Krumeich F, Baiker A, J. Mol. Catal. A-Chem., 309(1-2), 57 (2009)
  21. Wang M, Wang F, Ma J, Li M, Zhang Z, Wang Y, Zhang X, Xu J, Chem. Commun., 50, 292 (2013)
  22. So MH, Liu Y, Ho CM, Che CM, Chem. Asian J., 4, 1551 (2009)
  23. Zhang B, Guo XW, Liang H, Ge H, Gu X, Chen S, Yang H, Qin Y, ACS Catal., 6, 6560 (2016)
  24. Mielby J, Poreddy R, Engelbrekt C, Kegnæs S, Chin. J. Catal., 35, 670 (2014)
  25. Hammond C, Schumperli MT, Hermans I, Chem.-Eur. J., 19, 13193 (2013)
  26. He W, Wang L, Sun C, Wu K, He S, Chen J, Wu P, Yu Z, Chem.-Eur. J., 17, 13308 (2011)
  27. Chen B, Wang L, Dai W, Shang S, Lv Y, Gao S, ACS Catal., 5, 2788 (2015)
  28. Rard J, Chem. Rev., 85, 1 (1985)
  29. Meng QY, Zhong JJ, Liu Q, Gao XW, Zhang HH, Lei T, Li ZJ, Feng K, Chen B, Tung CH, Wu LZ, J. Am. Chem. Soc., 135(51), 19052 (2013)
  30. Meng QY, Liu Q, Zhong JJ, Zhang HH, Li ZJ, Chen B, Tung CH, Wu LZ, Org. Lett., 14, 5992 (2012)
  31. Schumperli MT, Hammond C, Hermans I, ACS Catal., 2, 1108 (2012)
  32. Kim JW, He J, Yamaguchi K, Mizuno N, Chem. Lett., 38(3), 920 (2009)
  33. Cano R, Ramon DJ, Yus M, J. Org. Chem., 76, 5547 (2011)
  34. Sun H, Su FZ, Ni J, Cao Y, He HY, Fan KN, Angew. Chem.-Int. Edit., 48, 4390 (2009)
  35. Gopiraman M, Karvembu R, Kim IS, ACS Catal., 4, 2118 (2014)
  36. Jin IK, Dao VD, Larina LL, Choi HS, J. Ind. Eng. Chem., 36, 238 (2016)
  37. Bao C, Zhou L, Shao Y, Wu Q, Zhu H, Li K, J. Ind. Eng. Chem., 38, 132 (2016)
  38. Pourjavadi A, Safaie N, Hosseini SH, Bennett C, J. Ind. Eng. Chem., 38, 82 (2016)
  39. Dong L, Gari RRS, Li Z, Craig MM, Hou S, Carbon, 48, 781 (2010)
  40. Siamaki AR, Khder AES, Abdelsayed V, El-Shall MS, Gupton BF, J. Catal., 279(1), 1 (2011)
  41. Yang J, Tian C, Wang L, Fu H, J. Mater. Chem., 21, 3384 (2011)
  42. Esteban RM, Schutte K, Marquardt D, Barthel J, Beckert F, Mulhaupt R, Janiak C, Nano-Struct. Nano-Objects, 2, 28 (2015)
  43. Marquardt D, Vollmer C, Thomann R, Steurer P, Mulhaupt R, Redel E, Janiak C, Carbon, 49, 1326 (2011)
  44. Gopiraman M, Deng D, Babu SG, Hayashi T, Karvembu R, Kim IS, ACS Sustain. Chem. Eng., 3, 2478 (2015)
  45. Gopiraman M, Babu SG, Khatri Z, Wei K, Kim YA, Endo M, Karvembu R, Kim IS, J. Phys. Chem. C, 117, 23582 (2013)
  46. Gopiraman M, Bang H, Babu SG, Wei K, Karvembu R, Kim IS, Catal. Sci. Technol., 4, 2099 (2014)
  47. Wang J, Chen B, Xing B, Environ. Sci. Technol., 50, 3798 (2016)
  48. Fan XB, Peng WC, Li Y, Li XY, Wang SL, Zhang GL, Zhang FB, Adv. Mater., 20(23), 4490 (2008)
  49. Zhou X, Huang X, Qi X, Wu S, Xue C, Boey FYC, Yan Q, Chen P, Zhang H, J. Phys. Chem. C, 113, 10842 (2009)
  50. Kurian M, Kunjachan C, Nano-Struct. Nano-Objects, 1, 15 (2015)
  51. Manhas M, Kumar V, Sharma V, Ntwaeaborwa OM, Swart HC, Nano-Struct. Nano-Objects, 3, 9 (2015)
  52. Makinson JD, Lee JS, Magner SH, De Angelis RJ, Weins WN, Hieronymus AS, Adv. X-ray Anal., 42, 407 (2000)
  53. Zhang F, Chan SW, Spanier JE, Apak E, Jin Q, Robinson RD, Herman IP, Appl. Phys. Lett., 80, 127 (2002)
  54. Reddy KM, Manorama SV, Reddy AR, Mater. Chem. Phys., 78, 239 (2002)
  55. Muneeswaran M, Jegatheesan P, Gopiraman M, Kim IS, Giridharan NV, Appl. Phys. A-Mater. Sci. Process., 114, 853 (2014)
  56. Akhavan O, Carbon, 48, 509 (2010)
  57. Datsyuk V, Kalyva M, Papagelis K, Tasis D, Siokou A, Kallitsis I, Galiotis C, Carbon, 46, 833 (2008)
  58. Gopiraman M, Babu SG, Khatri Z, Kai W, Kim YA, Endo M, Karvembu R, Kim IS, Carbon, 62, 135 (2013)
  59. Sankar J, Sham TK, Puddephatt RJ, J. Mater. Chem., 9, 2439 (1999)
  60. Blume R, Havecker M, Zafeiratos S, Teschner D, Kleimenov E, Knop-Gericke A, Schlogl R, Barinov A, Dudin P, Kiskinova M, J. Catal., 239(2), 354 (2006)
  61. Over H, Chem. Rev., 112(6), 3356 (2012)
  62. Gopiraman M, Babu SG, Karvembu R, Kim IS, Appl. Catal. A: Gen., 484, 84 (2014)
  63. Huang H, Huang J, Liu YM, He HY, Cao Y, Fan KN, Green Chem., 14, 930 (2012)