Zirconium phosphate nanoparticles as a remarkable solid acid catalyst for selective solvent-free alkylation of phenol

doi:10.1016/S1872-2067(14)60060-7

摘要/Abstract

摘要：

A facile synthesis of α-zirconium phosphate (ZP) nanoparticles as an effective, eco-friendly, and recyclable solid acid catalyst is reported. Polyvinylpyrrolidone (PVP) and polyvinyl alcohol (PVA) were used as organic matrix as dispersing agents and served as a template for the nanoparticles. Hydrogen bonds between ZP and PVA or PVP, along the polymer chains, appear to play an important role for improving the dispersion of in situ formed ZP. Following calcination of PVA/ZP or PVP/ZP, pure hexagonal ZP nanoparticles were obtained. The catalysts were characterized by nitrogen sorption, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy, and transmission electron microscopy. Pyridine-FTIR and temperature-programmed desorption of NH₃ suggest the presence of Brönsted acid sites. The acidic properties of the catalyst were studied in Friedel-Crafts alkylation of phenol by tert-butanol, producing 2-tert-butylphenol, 4-tert-butylphenol, and 2,4-di-tert-butylphenol. The alkylation reaction was performed in the presence of catalysts P₂O₅/Al₂O₃, P₂O₅/SiO₂, α-ZrP (prepared in the absence of the polymers), and various ionic liquids. The use of the hexagonal ZP nanoparticle catalyst afforded an excellent phenol conversion (86%) and selectivity towards 4-tert-butylphenol (83%) under optimized reaction conditions. The catalyst was easily recovered from the reaction mixture, regenerated, and reused at least four times without significant loss in the catalytic activity.

关键词: Hexagonal zirconium phosphate, Nanoparticle, Solvent free, Phenol alkylation, eterogeneous catalyst, Polyvinyl alcohol, Polyvinylpyrrolidone

Abstract:

Key words: Hexagonal zirconium phosphate, Nanoparticle, Solvent free, Phenol alkylation, eterogeneous catalyst, Polyvinyl alcohol, Polyvinylpyrrolidone

Abdol R. Hajipour, Hirbod Karimi. Zirconium phosphate nanoparticles as a remarkable solid acid catalyst for selective solvent-free alkylation of phenol[J]. 催化学报, 2014, 35(7): 1136-1147.

Abdol R. Hajipour, Hirbod Karimi. Zirconium phosphate nanoparticles as a remarkable solid acid catalyst for selective solvent-free alkylation of phenol[J]. Chinese Journal of Catalysis, 2014, 35(7): 1136-1147.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(14)60060-7

https://www.cjcatal.com/CN/Y2014/V35/I7/1136

参考文献

[1] Chandler K, Deng F, Dillow A K, Liotta C L, Eckert C A. Ind Eng Chem Res, 1997, 36: 5175
[2] Mehraban Z, Farzaneh F, Ghandi M, Abbasi A. Chin J Catal (催化学报), 2007, 28: 357
[3] Wu S J, Huang J H, Wu T H, Song K, Wang H S, Xing L H, Xu H Y, Xu L, Guan J Q, Kan Q B. Chin J Catal (吴淑杰, 黄家辉, 吴通好, 宋科, 王虹苏, 邢丽红, 徐海燕, 徐玲, 管景奇, 阚秋斌. 催化学报), 2006, 27: 9
[4] Shinde A B, Shrigadi N B, Samant S D. Appl Catal A, 2004, 276: 5
[5] Shen H Y, Judeh Z M A, Ching C B, Xia Q H. J Mol Catal A, 2004, 212: 301
[6] Dumitriu E, Hulea V. J Catal, 2003, 218: 249
[7] Venkatachalam K, Visuvamithiran P, Sundaravel B, Palanichamy M, Murugesan V. Chin J Catal (催化学报), 2012, 33: 478
[8] Sakthivel A, Badamali S K, Selvam P. Microporous Mesoporous Mater, 2000, 39: 457
[9] Ghiaci M, Aghabarari B. Chin J Catal (催化学报), 2010, 31: 759
[10] Usha Nandhini K, Herbert Mabel J, Arabindoo B, Palanichamy M, Murugesan V. Microporous Mesoporous Mater, 2006, 96: 21
[11] Wang Y L, Song Y Y, Huo W T, Jia M J, Jing X Y, Yang P P, Yang Z, Liu G, Zhang W X. Chem Eng J, 2012, 181-182: 630
[12] Modrogan E, Valkenberg M H, Hoelderich W F. J Catal, 2009, 261: 177
[13] Chandra K G, Sharma M M. Catal Lett, 1993, 19: 309
[14] Mathew T, Rao B S, Gopinath C S. J Catal, 2004, 222: 107
[15] Vinu A, Devassy B M, Halligudi S B, Böhlmann W, Hartmann M. Appl Catal A, 2005, 281: 207
[16] Bhatt N, Sharma P, Patel A, Selvam P. Catal Commun, 2008, 9: 1545
[17] Gui J Z, Ban H Y, Cong X H, Zhang X T, Hu Z D, Sun Z L. J Mol Catal A, 2005, 225: 27
[18] Vinu A, Nandhini K U, Murugesan V, Böhlmann W, Umamaheswari V, Pöppl A, Hartmann M. Appl Catal A, 2004, 265: 1
[19] Sears C A Jr. J Org Chem, 1948, 13: 120
[20] Elavarasan P, Kondamudi K, Upadhyayula S. Chem Eng J, 2011, 166: 340
[21] Clark J H. Acc Chem Res, 2002, 35: 791
[22] Kumar G S, Vishnuvarthan M, Palanichamy M, Murugesan V. J Mol Catal A, 2006, 260: 49
[23] Devassy B M, Shanbhag G V, Halligudi S B. J Mol Catal A, 2006, 247: 162
[24] Subramanian S, Mitra A, Satyanarayana C V V, Chakrabarty D K. Appl Catal A, 1997, 159: 229
[25] Sakthivel A, Saritha N, Selvam P. Catal Lett, 2001, 72: 225
[26] Haldar S, Koner S. J Org Chem, 2010, 75: 6005
[27] Sun L, Boo W J, Sue H J, Clearfield A. New J Chem, 2007, 31: 39
[28] Sun L, Boo W J, Browning R L, Sue H J, Clearfield A. Chem Mater, 2005, 17: 5606
[29] Trobajo C, Khainakov S A, Espina A, García J R. Chem Mater, 2000, 12: 1787
[30] Shuai M, Mejia A F, Chang Y W, Cheng Z D. CrystEngComm, 2013, 15: 1970
[31] Mishra S P, Tiwari D, Prasad S K, Dubey R S, Mishra M. J Radioanal Nucl Chem, 2006, 268: 191
[32] Kremlyakova N Y, Komarevsky V M. J Radioanal Nucl Chem, 1997, 218: 197
[33] Kamiya Y, Sakata S, Yoshinaga Y, Ohnishi R, Okuhara T. Catal Lett, 2004, 94: 45
[34] Sinhamahapatra A, Sutradhar N, Pahari S, Bajaj H C, Panda A B. Appl Catal A, 2011, 394: 93
[35] Sinhamahapatra A, Sutradhar N, Roy B, Pal P, Bajaj H C, Panda A B. Appl Catal B, 2011, 103: 378
[36] Sinhamahapatra A, Sutradhar N, Roy B, Tarafdar A, Bajaj H C, Panda A B. Appl Catal A, 2010, 385: 22
[37] Sinhamahapatra A, Sinha A, Pahari S K, Sutradhar N, Bajaj H C, Panda A B. Catal Sci Technol, 2012, 2: 2375
[38] Zhang F Z, Xie Y R, Lu W, Wang X Y, Xu S L, Lei X D. J Colloid Interf Sci, 2010, 349: 571
[39] Díaz A, David A, Pérez R, González M L, Báez A, Wark S E, Zhang P, Clearfield A, Colón J L. Biomacromolecules, 2010, 11: 2465
[40] Saxena V, Diaz A, Clearfield A, Batteas J D, Hussain M D. Nanoscale, 2013, 5: 2328
[41] Díaz A, Saxena V, González J, David A, Casańas B, Carpenter C, Batteas J D, Colón J L, Clearfield A, Hussain M D. Chem Commun, 2012, 48: 1754
[42] Kumar C V, Chaudhari A. J Am Chem Soc, 2000, 122: 830
[43] Feng Y J, He W, Zhang X D, Jia X T, Zhao H S. Mater Lett, 2007, 61: 3258
[44] Gupta V K, Pathania D, Singh P, Rathore B S, Chauhan P. Carbohydrate Polym, 2013, 95: 434
[45] Wei S Y, Lizu M, Zhang X, Sampathi J, Sun L Y, Milner M F. High Perform Polym, 2013, 25: 25
[46] Yang Y J, Liu C H, Chang P R, Chen Y, Anderson D P, Stumborg M. J Appl Polym Sci, 2010, 115: 1089
[47] Lu H D, Wilkie C A, Ding M, Song L. Polym Degrad Stab, 2011, 96: 1219
[48] Dana S F, Nguyen D V, Kochhar J S, Liu X Y, Kang L F. Soft Matter, 2013, 9: 6270
[49] Topkaya R, Kurtan U, Baykal A, Toprak M S. Ceram Int, 2013, 39: 5651
[50] Wang Z H, Tao D L, Guo G S, Jin S, Wei F, Qian W Z, Hong S, Guo J. Mater Lett, 2006, 60: 3104
[51] Adam F, Hello K M, Ali T H. Appl Catal A, 2011, 399: 42
[52] Zhao Q, Wang Q, Wu D L, Fu X Q, Jiang T S, Yin H B. J Ind Eng Chem, 2012, 18: 1326
[53] Hajipour A R, Azizi G. Green Chem, 2013, 15: 1030
[54] Hajipour A R, Zarei A, Khazdooz L, Pourmousavi S A, Mirjalili B B F, Ruoho A E. Phosphorus, Sulfur Silicon Relat Elem, 2005, 180: 2029
[55] Zarei A, Hajipour A R, Khazdooz L. Tetrahedron Lett, 2008, 49: 6715
[56] Hajipour A R, Khazdooz L, Ruoho A E. Catal Commun, 2008, 9: 89
[57] Hajipour A R, Nasresfahani Z. Synth Commun, 2012, 42: 1995
[58] Hajipour A R, Ghayeb Y, Sheikhan N, Ruoho A E. Tetrahedron Lett, 2009, 50: 5649
[59] Kirumakki S R, Nagaraju N, Chary K V R, Narayanan S. J Catal, 2004, 221: 549
[60] Venuto P B. Microporous Mater, 1994, 2: 297
[61] Sridevi U, Bhaskar Rao B K, Pradhan N C. Chem Eng J, 2001, 83: 185
[62] Becker K A, Karge H G, Streubel W D. J Catal, 1973, 28: 403
[63] Sing K S, Everett D H, Haul R A W, Pierotti R A, Rouquerol J, Siemieniewska T. Pure Appl Chem, 1985, 57: 603
[64] Segawa K, Nakata S, Asaoka S. Mater Chem Phys, 1987, 17: 181
[65] Tarafdar A, Panda A B, Pradhan N C, Pramanik P. Microporous Mesoporous Mater, 2006, 95: 360
[66] Tyagi B, Chudasama C D, Jasra R V. Appl Clay Sci, 2006, 31: 16
[67] Corma A. Chem Rev, 1995, 95: 559
[68] Segawa K i, Kurusu Y, Nakajima Y, Kinoshita M. J Catal, 1985, 94: 491
[69] Tahara S, Takakura Y, Sugahara Y. Chem Lett, 2012, 41: 555
[70] Yang X S, Chen X, Yang L, Yang W S. Bioelectrochemistry, 2008, 74: 90
[71] Reddy K S N, Rao B S, Shiralkar V P. Appl Catal A, 1993, 95: 53
[72] Luque R, Budarin V, Clark J H, Shuttleworth P, White R J. Catal Commun, 2011, 12: 1471
[73] Graça I, Fernandes A, Lopes J M, Ribeiro M F, Laforge S, Magnoux P, Ramôa Ribeiro F. Appl Catal A, 2010, 385: 178
[74] Yadav G D, Nair J J. Microporous Mesoporous Mater, 1999, 33: 1
[75] Iglesia E, Soled S L, Kramer G M. J Catal, 1993, 144: 238
[76] Zhang K, Huang C, Zhang H, Xiang S, Liu S, Xu D, Li H. Appl Catal A, 1998, 166: 89
[77] Bhatt N, Patel A. J Taiwan Inst Chem Eng, 2011, 42: 356
[78] Parton R F, Jacobs J M, Huybrechts D R, Jacobs P A. Shape-Selective Catalysis in Zeolites with Organic Substrates Containing Oxygen. Amsterdam: Elsevier, 1989. 163
[79] Devassy B M, Shanbhag G V, Mirajkar S P, Böhringer W, Fletcher J, Halligudi S B. J Mol Catal A, 2005, 233: 141