ZnAl2O4@SiO2 nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions

doi:10.1016/S1872-2067(12)60758-X

Abstract

Abstract:

A ZnAl₂O₄@SiO₂ nanocomposite was prepared from metal nitrates and tetraethyl orthosilicate by the sol-gel process, and characterized by X-ray diffraction, Fourier transform infrared, transmission electron microscopy, and N₂ adsorption-desorption measurements. The nanocomposite was tested as a heterogeneous catalyst for the acetylation of alcohols, phenols, and amines under solvent-free conditions. Under optimized conditions, efficient acetylation of these substrates with acetic anhydride over the ZnAl₂O₄@SiO₂ nanocomposite was obtained. Acetylation of anilines and primary aliphatic amines proceeded rapidly at room temperature, while the reaction time was longer for the acetylation of alcohols and phenols, showing that an amine NH₂ group can be selectively acetylated in the presence of alcoholic or phenolic OH groups. The catalyst can be reused without obvious loss of catalytic activity. The catalytic activity of the ZnAl₂O₄@SiO₂ nanocomposite was higher than that of pure ZnAl₂O₄. The method gives high yields, and is clean, cost effective, compatible with substrates having other functional groups and it is suitable for practical organic synthesis.

Key words: Spinel-type oxide, Zinc aluminate, Silica, Sol-gel process, Nanocomposite, Heterogeneous catalyst, Acetylation, Solvent-free condition

Saeed Farhadi, Kosar Jahanara. ZnAl₂O₄@SiO₂ nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions[J]. Chinese Journal of Catalysis, 2014, 35(3): 368-375.

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URL: https://www.cjcatal.com/EN/10.1016/S1872-2067(12)60758-X

https://www.cjcatal.com/EN/Y2014/V35/I3/368

References

[1] Hanson J R. Protecting Groups in Organic Synthesis. 1st Ed. Malden: Blackwell Science, 1999
[2] Greene T W, Wuts P G M. Protective Groups in Organic Synthesis. 3rd Ed. New York: Wiley, 1999
[3] Orita A, Tanahashi C, Kakuda A, Otera J. Angew Chem Int Ed, 2000, 39: 2877
[4] Nakae Y, Kusaki I, Sato T. Synlett, 2001: 1584
[5] Chandra K L, Saravanan P, Singh R K, Singh V K. Tetrahedron, 2002, 58: 1369
[6] Dalpozzo R, De Nino A, Maiuolo L, Procopio A, Nardi M, Bartoli G, Romeo R. Tetrahedron Lett, 2003, 44: 5621
[7] Chakraborti A K, Gulhane R. Tetrahedron Lett, 2003, 44: 6749
[8] Bartoli G, Bosco M, Dalpozzo R, Marcantoni E, Massaccesi M, Rinaldi S, Sambri L. Synlett, 2003: 39
[9] Bartoli G, Bosco M, Dalpozzo R, Marcantoni E, Massaccesi M, Sambri L. Eur J Org Chem, 2003: 4611
[10] De S K. Tetrahedron Lett, 2004, 45: 2919
[11] Phukan P. Tetrahedron Lett, 2004, 45: 4785
[12] Heravi M M, Behbahani F K, Bamoharram F F. J Mol Catal A, 2006, 253: 16
[13] Moghadam M, Tangestaninejad S, Mirkhani V, Mohamadpoor-Baltork I, Taghavi S A. J Mol Catal A, 2007, 274: 217
[14] Sartori G, Ballini R, Bigi F, Bosica G, Maggi R, Righi P. Chem Rev, 2004, 104: 199
[15] Sakakura A, Kawajiri K, Ohkubo T, Kosugi Y, Ishihara K. J Am Chem Soc, 2007, 129: 14775
[16] Chakraborti A K, Gulhane R. Chem Commun, 2003, 15: 1896
[17] Choudary B M, Bhaskar V, Kantam M L, Rao K K, Raghavan K V. Green Chem, 2000, 2: 67
[18] Bhaskar P M, Loganathan D. Tetrahedron Lett, 1998, 39: 2215
[19] Kantam M L, Ranganath K V S, Sateesh M, Sreedhar B, Choudary B M. J Mol Catal A, 2006, 244: 213
[20] Sarvari M H, Sharghi H. Tetrahedron, 2005, 61: 10903
[21] Thakuria H, Borah B M, Das G. J Mol Catal A, 2007, 274: 1
[22] Moghaddam F M, Saeidian H. Mater Sci Eng B, 2007, 139: 265
[23] Shirini F, Zolfigol M A, Mohammadi K. Bull Korean Chem Soc, 2004, 25: 325
[24] Ballini R, Bosica G, Carloni S, Ciaralli L, Maggi R, Sartori G. Tetrahedron Lett, 1998, 39: 6049
[25] Chavan S P, Anand R, Pasupathy K, Rao B S. Green Chem, 2001, 3: 320
[26] Chakraborti A K, Gulhane R. Tetrahedron Lett, 2003, 44: 3521
[27] Joseph J K, Jain S L, Sain B. J Mol Catal A, 2007, 267: 108
[28] Das B, Thirupathi P. J Mol Catal A, 2007, 269: 12
[29] Ratnam K J, Reddy R S, Sekhar N S, Kantam M L, Figueras F. J Mol Catal A, 2007, 276: 230
[30] Satam J R, Jayaram R V. Catal Commun, 2008, 9: 2365
[31] Rajabi F. Tetrahedron Lett, 2009, 50: 395
[32] Niknam K, Saberi D. Tetrahedron Lett, 2009, 50: 5210
[33] Niknam K, Saberi D. Appl Catal A, 2009, 366: 220
[34] Ghaffari-Khaligh N. J Mol Catal A, 2012, 363-364: 90
[35] Rahmatpour A. CR Chim, 2012, 15: 1048
[36] Osiglio L, Sathicq A G, Romanelli G P, Blanco M N. J Mol Catal A. 2012, 359: 97
[37] Shirini F, Akbari-Dadamahaleh S, Mohammad-Khah A, Aliakbar A R. CR Chim, 2013, 16: 207
[38] Taghavi S A, Moghadam M, Mohammadpoor-Baltork I, Tangestaninejad S, Mirkhani V, KhosropourA R. Inorg Chim Acta, 2011, 377: 159
[39] Yadegari M, Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I. Polyhedron, 2011, 30: 2237.
[40] Moghadam M, Tangestaninejad S, Mirkhani V, Mohammadpoor-Baltork I, Gharaati S. CR Chim, 2011, 14: 1080
[41] Ghorbani-Choghamarani A, Pourbahar N. Chin J Catal (催化学报), 2012, 33: 1470
[42] Pushpaletha P, Lalithambika M. Appl Clay Sci, 2011, 51: 424
[43] Shirini F, Ghaffari-Khaligh N. Chin J Catal (催化学报), 2013, 34: 695
[44] Nowrouzi N, Alizadeh S Z. Chin J Catal (催化学报), 2013, 34: 1787
[45] Iranpoor N, Firouzabadi H, Etemadi-Davan E. Tetrahedron Lett, 2013, 54: 1813
[46] Hajjami M, Ghorbani-Choghamarani A. Norouzi M. Chin J Catal (催化学报), 2012, 33: 1661
[47] Zareyee D, Alizadeh P, Ghandali M S, Khalilzadeh M A. Chem Papers, 2013, 67: 713
[48] Rajabi F, Luque R. Catal Commun, 2014, 45: 129
[49] Alam M, Rahman A, Alandis N M, Shaik M R. Arab J Chem, 2014, 7: 53
[50] Singh S J, Kale S R, Gawande M B, Velhinho A, Jayaram R V. Catal Commun, 2014, 44: 24
[51] Spinicci R, Faticanti M, Marini P, DeRossi S, Porta P. J Mol Catal A, 2003, 197: 147
[52] Barbero B P, Gamboa J A, Cadus L E. Appl Catal B, 2006, 65: 21
[53] Merino N A, Barbero B P, Ruiz P, Cadus L E. J Catal, 2006, 240: 245
[54] Grabowska H, Zawadzki M, Syper L. Appl Catal A, 2006, 314: 226
[55] Farhadi S, Zaidi M. J Mol Catal A, 2009, 299: 18
[56] Farhadi S, Panahandehjoo S. Appl Catal A, 2010, 382: 293
[57] Landau M V, Titelman L, Vradman L, Wilson P. Chem Commun, 2003: 594
[58] Liu Y M, Cao Y, Yi N, Feng W L, Dai W L, Yan R S, He H Y, Fan K N. J Catal, 2004, 224: 417
[59] Wang X G, Landau M V, Rotter H, Vradman L, Wolfson A, Erenberg A. J Catal, 2004, 222: 565
[60] Cullity B D, Stock S R. Elements of X-ray Diffraction. 3rd Ed. New Jersey: Prentice-Hall, Englewood Cliffs, 2001
[61] Duan X L, Yuan D R, Sun Z H, Sun H Q, Xu D, Lü M K. J Cryst Growth, 2003, 252: 4
[62] Mazza D, Vallino M, Busca G. J Am Ceram Soc, 1992, 75: 1929

ZnAl₂O₄@SiO₂ nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions

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