Copyright (c) 2018 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis of Zeolite Beta and Zeolite ZSM-5 from High Silica Raw Kaolinite and Their Catalytic Etherification of Ethylene Glycol
Corresponding Author(s) : Hamdallah A. Hodali
Asian Journal of Chemistry,
Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Abstract
Pure phases of zeolites Beta and ZSM-5 were synthesized from high silica raw kaolinite. Both zeolites were characterized by XRD, XRF, SEM and N2 adsorption/desorption isotherms. The acid forms of zeolites (H-zeolite) were used in the catalytic etherification of ethylene glycol with benzyl alcohol and with t-butanol. In the reaction of ethylene glycol with benzyl alcohol, ethylene glycol monobenzyl ether was the only detected product over H-ZSM-5, while in case of H-zeolite Beta, ethylene glycol monobenzyl ether and ethylene glycol dibenzyl ether were detected. The highest yield of ethylene glycol monobenzyl ether (58 %) was obtained from H-ZSM-5 prepared from raw kaolinite.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- (a) J. Perez-Pariente, J.A. Martens and P.A. Jacobs, Zeolites, 8, 46 (1988); https://doi.org/10.1016/S0144-2449(88)80029-0. (b) R.L. Wadlinger, G.T. Kerr and E.J. Rosinski, Catalytic Composition of a Crystalline Zeolite, US Patent 3,308,069 (1967).
- M.W. Kasture, P.S. Niphadkar, S.R. Kate, P.D. Godbole, K.R. Patil, G.M. Chaphekar and P.N. Joshi, Stud. Surf. Sci. Catal., 154, 3081 (2004); https://doi.org/10.1016/S0167-2991(04)80595-0.
- Y.J. Lee, S.D. Kim, S.C. Byun, J.W. Park, Y.J. Jeong, Y.J. Kwon, H.O. Song and W. Kim, J. Cryst. Growth, 297, 138 (2006); https://doi.org/10.1016/j.jcrysgro.2006.09.040.
- A. Sagarzazu and G. Gonzalez, Mater. Chem. Phys., 138, 640 (2013); https://doi.org/10.1016/j.matchemphys.2012.12.033.
- H.H. Murray, Clay Miner., 34, 39 (1999); https://doi.org/10.1180/000985599546055.
- Y. Zhang, W. Gao and L. Cui, Stud. Surf. Sci. Catal., 170, 420 (2007); https://doi.org/10.1016/S0167-2991(07)80870-6.
- A. Duan, G. Wan, Y. Zhang, Z. Zhao, G. Jiang and J. Liu, Catal. Today, 175, 485 (2011); https://doi.org/10.1016/j.cattod.2011.03.044.
- R.J. Argauer and G.R. Landolt, Crystalline Zeolite ZSM-5 and Method of preparing the Same. US Patent No. 3,702,886 (1972).
- N. Kumar, V. Nieminen, K. Demirkan, T. Salmi, D. Yu. Murzin and E. Laine, Appl. Catal. A, 235, 113 (2002); https://doi.org/10.1016/S0926-860X(02)00258-2.
- Q. Dai, S. Bai, X. Wang and G. Lu, J. Porous Mater., 21, 1041 (2014); https://doi.org/10.1007/s10934-014-9854-z.
- C. Liu, W. Gu, D. Kong and H. Guo, Micropor. Mesopor. Mater., 183, 30 (2014); https://doi.org/10.1016/j.micromeso.2013.08.037.
- C.D. Madhusoodana, Y. Kameshima, A. Yasumori and K. Okada, Clay Sci., 11, 369 (2001).
- C.D. Madhusoodana, R.N. Das, Y. Kameshima and K. Okada, J. Porous Mater., 12, 273 (2005); https://doi.org/10.1007/s10934-005-3125-y.
- E. Vessally, M.D. Esrafili, Z. Alimadadi and M. Rouhani, Green Chem. Lett. Rev., 7, 119 (2014); https://doi.org/10.1080/17518253.2014.895865.
- F. Pan, X. Lu, Y. Wang, S. Chen, T. Wang and Y. Yan, Mater. Lett., 115, 5 (2014); https://doi.org/10.1016/j.matlet.2013.10.007.
- A.S. Kovo, O. Hernandez and S.M. Holmes, Mater. Chem., 19, 6207 (2009); https://doi.org/10.1039/b907554b.
- A.F. Lafi, S.K. Matam and H.A. Hodali, Ind. Eng. Chem. Res., 54, 3754 (2015); https://doi.org/10.1021/ie505004k.
- T. Tejero, C. Fité, M. Iborra, J.F. Izquierdo, F. Cunill and R. Bringué, Micropor. Mesopor. Mater., 117, 650 (2009); https://doi.org/10.1016/j.micromeso.2008.08.055.
- E. Medina, R. Bringue, J. Tejero, M. Iborra and C. Fite, Appl. Catal. A, 374, 41 (2010); https://doi.org/10.1016/j.apcata.2009.11.024.
- I. Hoek, T.A. Nijhuis, A.I. Stankiewicz and J.A. Moulijn, Appl. Catal. A, 266, 109 (2004); https://doi.org/10.1016/j.apcata.2004.02.005.
- J.F. Knifton and P.E. Dai, One-Step Synthesis of Methyl t-Butyl ether from t-Butanol using β-zeolite catalysts Modified with Lithium Plus Rare Earths, US Patent 5,387,723 (1995).
- S. Assabumrungrat, D. Wongwattanasate, V. Pavarajarn, P. Praserthdam, A. Arpornwichanop and S. Goto, Korean J. Chem. Eng., 21, 1139 (2004); https://doi.org/10.1007/BF02719485.
- J.W. Kim, D.J. Kim, J.U. Han, M. Kang, J.M. Kim and J.E. Yie, Catal. Today, 87, 195 (2003); https://doi.org/10.1016/j.cattod.2003.10.006.
- C. Gonzalez-Arellano, A. Grau-Atienza, E. Serrano, A.A. Romero, J. Garcia-Martinez and R. Luque, J. Mol. Catal. A-Chem., 406, 40 (2015); https://doi.org/10.1016/j.molcata.2015.05.011.
- M. Kubota, A. Sakamoto, M. Komatsu, K. Maeno and A. Masuyama, J. Oleo Sci., 63, 1057 (2014); https://doi.org/10.5650/jos.ess13214.
- N. Ozbay, N. Oktar, G. Dogu and T. Dogu, Top. Catal., 56, 1790 (2013); https://doi.org/10.1007/s11244-013-0116-0.
- M.D. Gonzalez, P. Salagre, M. Linares, R. Garcia, D. Serrano and Y. Cesteros, Appl. Catal. A, 473, 75 (2014); https://doi.org/10.1016/j.apcata.2013.12.038.
- B. Guruswamy and R. Arul, Lett. Drug Des. Discov., 10, 86 (2013); https://doi.org/10.2174/157018013804142492.
- K. Huang, M. Ortiz-Marciales, W. Correa, E. Pomales and X.Y. López, J. Org. Chem., 74, 4195 (2009); https://doi.org/10.1021/jo900666r.
- J.M. Bobbitt, A.L. Bartelson, W.F. Bailey, T.A. Hamlin and C.B. Kelly, J. Org. Chem., 79, 1055 (2014); https://doi.org/10.1021/jo402519m.
- G.D. Yadav and S. Singh, Tetrahedron Lett., 55, 3979 (2014); https://doi.org/10.1016/j.tetlet.2014.05.017.
- D.R. Billodeaux, T.J. Devon, J.M. Penney, D.L. Terrill, R.T. Hembre and J.L. Stavinoha, Production of Hydroxy Ether Hydrocarbons by Liquid Phase Hydrogenolysis of Cyclic Acetals or Cyclic Ketals, WO Patent 177,469 (2012).
- H. Kotsuki, Y. Ushio, N. Yoshimura and M. Ochi, J. Org. Chem., 52, 2594 (1987); https://doi.org/10.1021/jo00388a049.
- T. Yoshino, S. Inaba and Y. Ishido, Bull. Chem. Soc. Jpn., 46, 553 (1973); https://doi.org/10.1246/bcsj.46.553.
- Y. Liu, S.K. Park, Y. Xiao and J. Chae, Org. Biomol. Chem., 12, 4747 (2014); https://doi.org/10.1039/c4ob00649f.
- G.D. Yadav, S.O. Katole and A.K. Dalai, Appl. Catal. A, 477, 18 (2014); https://doi.org/10.1016/j.apcata.2014.02.017.
- V.I. Parvulescu, S.M. Coman, N.C. Candu, J. El Haskouri, D. Beltran and P. Amoros, J. Mater. Sci., 44, 6693 (2009); https://doi.org/10.1007/s10853-009-3599-0.
- M.A. Camblor and J. Perez-pariente, Zeolites, 11, 202 (1991); https://doi.org/10.1016/S0144-2449(05)80220-9.
References
(a) J. Perez-Pariente, J.A. Martens and P.A. Jacobs, Zeolites, 8, 46 (1988); https://doi.org/10.1016/S0144-2449(88)80029-0. (b) R.L. Wadlinger, G.T. Kerr and E.J. Rosinski, Catalytic Composition of a Crystalline Zeolite, US Patent 3,308,069 (1967).
M.W. Kasture, P.S. Niphadkar, S.R. Kate, P.D. Godbole, K.R. Patil, G.M. Chaphekar and P.N. Joshi, Stud. Surf. Sci. Catal., 154, 3081 (2004); https://doi.org/10.1016/S0167-2991(04)80595-0.
Y.J. Lee, S.D. Kim, S.C. Byun, J.W. Park, Y.J. Jeong, Y.J. Kwon, H.O. Song and W. Kim, J. Cryst. Growth, 297, 138 (2006); https://doi.org/10.1016/j.jcrysgro.2006.09.040.
A. Sagarzazu and G. Gonzalez, Mater. Chem. Phys., 138, 640 (2013); https://doi.org/10.1016/j.matchemphys.2012.12.033.
H.H. Murray, Clay Miner., 34, 39 (1999); https://doi.org/10.1180/000985599546055.
Y. Zhang, W. Gao and L. Cui, Stud. Surf. Sci. Catal., 170, 420 (2007); https://doi.org/10.1016/S0167-2991(07)80870-6.
A. Duan, G. Wan, Y. Zhang, Z. Zhao, G. Jiang and J. Liu, Catal. Today, 175, 485 (2011); https://doi.org/10.1016/j.cattod.2011.03.044.
R.J. Argauer and G.R. Landolt, Crystalline Zeolite ZSM-5 and Method of preparing the Same. US Patent No. 3,702,886 (1972).
N. Kumar, V. Nieminen, K. Demirkan, T. Salmi, D. Yu. Murzin and E. Laine, Appl. Catal. A, 235, 113 (2002); https://doi.org/10.1016/S0926-860X(02)00258-2.
Q. Dai, S. Bai, X. Wang and G. Lu, J. Porous Mater., 21, 1041 (2014); https://doi.org/10.1007/s10934-014-9854-z.
C. Liu, W. Gu, D. Kong and H. Guo, Micropor. Mesopor. Mater., 183, 30 (2014); https://doi.org/10.1016/j.micromeso.2013.08.037.
C.D. Madhusoodana, Y. Kameshima, A. Yasumori and K. Okada, Clay Sci., 11, 369 (2001).
C.D. Madhusoodana, R.N. Das, Y. Kameshima and K. Okada, J. Porous Mater., 12, 273 (2005); https://doi.org/10.1007/s10934-005-3125-y.
E. Vessally, M.D. Esrafili, Z. Alimadadi and M. Rouhani, Green Chem. Lett. Rev., 7, 119 (2014); https://doi.org/10.1080/17518253.2014.895865.
F. Pan, X. Lu, Y. Wang, S. Chen, T. Wang and Y. Yan, Mater. Lett., 115, 5 (2014); https://doi.org/10.1016/j.matlet.2013.10.007.
A.S. Kovo, O. Hernandez and S.M. Holmes, Mater. Chem., 19, 6207 (2009); https://doi.org/10.1039/b907554b.
A.F. Lafi, S.K. Matam and H.A. Hodali, Ind. Eng. Chem. Res., 54, 3754 (2015); https://doi.org/10.1021/ie505004k.
T. Tejero, C. Fité, M. Iborra, J.F. Izquierdo, F. Cunill and R. Bringué, Micropor. Mesopor. Mater., 117, 650 (2009); https://doi.org/10.1016/j.micromeso.2008.08.055.
E. Medina, R. Bringue, J. Tejero, M. Iborra and C. Fite, Appl. Catal. A, 374, 41 (2010); https://doi.org/10.1016/j.apcata.2009.11.024.
I. Hoek, T.A. Nijhuis, A.I. Stankiewicz and J.A. Moulijn, Appl. Catal. A, 266, 109 (2004); https://doi.org/10.1016/j.apcata.2004.02.005.
J.F. Knifton and P.E. Dai, One-Step Synthesis of Methyl t-Butyl ether from t-Butanol using β-zeolite catalysts Modified with Lithium Plus Rare Earths, US Patent 5,387,723 (1995).
S. Assabumrungrat, D. Wongwattanasate, V. Pavarajarn, P. Praserthdam, A. Arpornwichanop and S. Goto, Korean J. Chem. Eng., 21, 1139 (2004); https://doi.org/10.1007/BF02719485.
J.W. Kim, D.J. Kim, J.U. Han, M. Kang, J.M. Kim and J.E. Yie, Catal. Today, 87, 195 (2003); https://doi.org/10.1016/j.cattod.2003.10.006.
C. Gonzalez-Arellano, A. Grau-Atienza, E. Serrano, A.A. Romero, J. Garcia-Martinez and R. Luque, J. Mol. Catal. A-Chem., 406, 40 (2015); https://doi.org/10.1016/j.molcata.2015.05.011.
M. Kubota, A. Sakamoto, M. Komatsu, K. Maeno and A. Masuyama, J. Oleo Sci., 63, 1057 (2014); https://doi.org/10.5650/jos.ess13214.
N. Ozbay, N. Oktar, G. Dogu and T. Dogu, Top. Catal., 56, 1790 (2013); https://doi.org/10.1007/s11244-013-0116-0.
M.D. Gonzalez, P. Salagre, M. Linares, R. Garcia, D. Serrano and Y. Cesteros, Appl. Catal. A, 473, 75 (2014); https://doi.org/10.1016/j.apcata.2013.12.038.
B. Guruswamy and R. Arul, Lett. Drug Des. Discov., 10, 86 (2013); https://doi.org/10.2174/157018013804142492.
K. Huang, M. Ortiz-Marciales, W. Correa, E. Pomales and X.Y. López, J. Org. Chem., 74, 4195 (2009); https://doi.org/10.1021/jo900666r.
J.M. Bobbitt, A.L. Bartelson, W.F. Bailey, T.A. Hamlin and C.B. Kelly, J. Org. Chem., 79, 1055 (2014); https://doi.org/10.1021/jo402519m.
G.D. Yadav and S. Singh, Tetrahedron Lett., 55, 3979 (2014); https://doi.org/10.1016/j.tetlet.2014.05.017.
D.R. Billodeaux, T.J. Devon, J.M. Penney, D.L. Terrill, R.T. Hembre and J.L. Stavinoha, Production of Hydroxy Ether Hydrocarbons by Liquid Phase Hydrogenolysis of Cyclic Acetals or Cyclic Ketals, WO Patent 177,469 (2012).
H. Kotsuki, Y. Ushio, N. Yoshimura and M. Ochi, J. Org. Chem., 52, 2594 (1987); https://doi.org/10.1021/jo00388a049.
T. Yoshino, S. Inaba and Y. Ishido, Bull. Chem. Soc. Jpn., 46, 553 (1973); https://doi.org/10.1246/bcsj.46.553.
Y. Liu, S.K. Park, Y. Xiao and J. Chae, Org. Biomol. Chem., 12, 4747 (2014); https://doi.org/10.1039/c4ob00649f.
G.D. Yadav, S.O. Katole and A.K. Dalai, Appl. Catal. A, 477, 18 (2014); https://doi.org/10.1016/j.apcata.2014.02.017.
V.I. Parvulescu, S.M. Coman, N.C. Candu, J. El Haskouri, D. Beltran and P. Amoros, J. Mater. Sci., 44, 6693 (2009); https://doi.org/10.1007/s10853-009-3599-0.
M.A. Camblor and J. Perez-pariente, Zeolites, 11, 202 (1991); https://doi.org/10.1016/S0144-2449(05)80220-9.