화학공학소재연구정보센터
Journal of Industrial and Engineering Chemistry, Vol.40, 40-46, August, 2016
cis-Cyclooctene epoxidation catalyzed by bulk metallophthalocyanines, metallohexadecafluorophthalocyanines and hollow silica-supported metallohexadecafluorophthalocyanine
E-mail:
We employed a variety of catalysts including metallophthalocyanines and metallohexadecafluor- ophthalocyanines for epoxidation of cis-cyclooctene in water as a green solvent. Manganese phthalocyanine and poly(copper phthalocyanine) are highly active while other metallophthalocyanines (Zn, Cu, Ni, Li) are nearly not active. Similarly, copper and cobalt hexadecafluorophthalocyanines show highly catalytic activity, but zinc hexadecafluorophthalocyanine is inactive. Moreover, iron phthalocya-nine chloride is also a good catalyst while nickel phthalocyanine-tetrasulfonic acid tetrasodium is a poor catalyst. Copper hexadecafluorophthalocyanine incorporated into hollow silica exhibits much better catalytic activity than bulk copper hexadecafluorophthalocyanine. This supported catalyst also gives a stable conversion until the fourth cycle of reaction.
  1. Nappa MJ, Tolman CA, Inorg. Chem., 24, 4711 (1985)
  2. Stochel G, Brindell M, Macyk W, Stasicka Z, Szaciłowski K, Therapeutic Strategies, John Wiley & Sons Ltd, 2009p. 293.
  3. Piroozmand M, Safari N, Samadi AA, Iran. J. Chem. Chem. Eng., 25, 85 (2006)
  4. Xue J, Wang A, Yin H, Wang J, Zhang D, Chen W, Yu L, Jiang T, J. Ind. Eng. Chem., 16(2), 288 (2010)
  5. Ansmann A, Kawa R, Neuss M, Cosmetic composition containing hydroxyethers, Cognis Deutschland GmbH & Co. KG (Duesseldorf DE), United States, 2006.
  6. Parrodi CAD, Juaristi E, Synlett, 2699 (2006)
  7. Guo QX, Nakajima K, Takahashi T, Chem. Lett., 32(11), 1044 (2003)
  8. Hodgson DM, Wisedale R, Tetrahedron: Asymmetry, 7, 1275 (1996)
  9. Liao ZK, Boriack CJ, Epoxidation process for aryl allyl ethers, The Dow Chemical Company (Midland MI), United States, 2000.
  10. Luo W, Sun J, Ye J, Deng W, Liu Q, Guo C, J. Ind. Eng. Chem., 20(5), 3061 (2014)
  11. Lyons JE, Ellis PE, Myers HK, J. Catal., 155(1), 59 (1995)
  12. Ellis PE, Lyons JE, Coord. Chem. Rev., 105, 181 (1990)
  13. Meunier B, Chem. Rev., 92, 1411 (1992)
  14. Sorokin AB, Chem. Rev., 113(10), 8152 (2013)
  15. Balkus KJ, Eissa M, Levado R, J. Am. Chem. Soc., 117(43), 10753 (1995)
  16. Bedioui F, Coord. Chem. Rev., 144, 39 (1995)
  17. Zalomaeva OV, Kovalenko KA, Chesalov YA, Mel’gunov MS, Zaikovskii VI, Kaichev VV, Sorokin AB, Kholdeeva OA, Fedin VP, J. Chem. Soc.-Dalton Trans., 40, 1441 (2011)
  18. Sorokin A, Meunier B, J. Chem. Soc.-Chem. Commun., 1799 (1994)
  19. Sanchez M, Chap N, Cazaux JB, Meunier B, Eur. J. Inorg. Chem., 2001, 1775 (2001)
  20. Sorokin AB, Tuel A, Catal. Today, 57(1-2), 45 (2000)
  21. Sorokin AB, Mangematin S, Pergrale C, J. Mol. Catal. A-Chem., 182-183, 267 (2002)
  22. Perollier C, Sorokin AB, Chem. Commun., 1548 (2002)
  23. DeOliveira E, Neri CR, Ribeiro AO, Garcia VS, Costa LL, Moura AO, Prado AGS, Serra OA, Iamamoto Y, J. Colloid Interface Sci., 323(1), 98 (2008)
  24. Remy B, Deby-Dupont G, Lamy M, Brit. Med. Bull., 55, 277 (1999)
  25. Riess JG, Vox Sang., 61, 225 (1991)
  26. Riess JG, Chem. Rev., 101(9), 2797 (2001)
  27. Solovyeva VA, Vu KB, Merican Z, Sougrat R, Rodionov VO, ACS Comb. Sci., 16, 513 (2014)
  28. Staniford MC, Lezhnina MM, Gruener M, Stegemann L, Kuczius R, Bleicher V, Strassert CA, Kynast UH, Chem. Commun., 51, 13534 (2015)
  29. Collman J, Zhang X, Lee V, Uffelman E, Brauman J, Science, 261, 1404 (1993)
  30. Reid N, Barat R, Chem. Eng. Commun., 203(6), 714 (2016)
  31. Bartoli JF, Battioni P, De Foor WR, Mansuy D, J. Chem. Soc.-Chem. Commun., 23 (1994)
  32. Lyons J, Ellis P, Catal. Lett., 8, 45 (1991)
  33. Traylor PS, Dolphin D, Traylor TG, J. Chem. Soc.-Chem. Commun., 279 (1984)
  34. Traylor TG, Tsuchiya S, Inorg. Chem., 26, 1338 (1987)
  35. Chibwe M, Pinnavaia TJ, J. Chem. Soc.-Chem. Commun., 278 (1993)
  36. Tatsuno Y, Sekiya A, Tani K, Saito T, Chem. Lett., 889 (1986)
  37. Hue QS, Margolese DI, Ciesla U, Feng PY, Gier TE, Sieger P, Leon R, Petroff PM, Schuth F, Stucky GD, Nature, 368(6469), 317 (1994)
  38. Kosmulski M, J. Colloid Interface Sci., 337(2), 439 (2009)
  39. Shin YC, Lee DK, Lee KT, Ahn KH, Kim BS, J. Ind. Eng. Chem., 14(4), 515 (2008)
  40. Bai L, Li K, Yan Y, Jia X, Lee JM, Yang Y, ACS Sustain. Chem. Eng., 4, 437 (2016)
  41. Mizuno N, Nozaki C, Kiyoto I, Misono M, J. Catal., 182(1), 285 (1999)
  42. Bai L, Yao L, Yang Y, Lee JM, Chem. Commun., 51, 4259 (2015)
  43. Bawaked S, Dummer NF, Dimitratos N, Bethell D, He Q, Kiely CJ, Hutchings GJ, Green Chem., 11, 1037 (2009)
  44. Bawaked S, He Q, Dummer NF, Carley AF, Knight DW, Bethell D, Kiely CJ, Hutchings GJ, Catal. Sci. Technol., 1, 747 (2011)
  45. Bawaked S, Dummer NF, Bethell D, Knight DW, Hutchings GJ, Green Chem., 13, 127 (2011)
  46. Mahajan SS, Sharma MM, Sridhar T, Ind. Eng. Chem. Res., 44(5), 1390 (2005)
  47. Herron N, Stucky GD, Tolman CA, J. Chem. Soc.-Chem. Commun., 1521 (1986)
  48. Parton RF, Uytterhoeven L, Jacobs PA, Stud. Surf. Sci. Catal., 59, 395 (1991)
  49. Nakamura M, Tatsumi T, Tominaga HO, Bull. Chem. Soc. Jpn., 63, 3334 (1990)
  50. Seelan S, Sinha AK, Srinivas D, Sivasanker S, J. Mol. Catal. A-Chem., 157(1-2), 163 (2000)
  51. Bach RD, Knight JW, Org. Synth., 60, 63 (1981)
  52. Brauer HD, Eilers B, Lange A, J. Chem. Soc.-Perkin Trans. 2, 1288 (2002)
  53. Finazzo C, Calle C, Stoll S, Van Doorslaer S, Schweiger A, Phys. Chem. Chem. Phys., 8, 1942 (2006)