Heterogenization of Indium for the Friedel-Craft Benzoylation of Toluene

doi:10.1016/S1872-2067(11)60453-1

摘要/Abstract

摘要： Indium incorporated silica samples with different indium contents were synthesized using a template free sol-gel method. The silica used was extracted from rice husk (RH) and the resulting catalyst was labeled as RH-xIn (x = 5%, 10%, 15%, and 20%). From the N₂ adsorption analysis the presence of type IV isotherm in RH-blank and RH-xIn indicated the mesoporous nature of the catalysts. In the XRD pattern, a broad band at ca. 2θ = 25° was observed for all the catalysts which showed them to be amorphous. TEM micrographs revealed that the material is composed of nanoparticles. Friedel-Craft benzoylation of toluene was carried out using the RH-xIn catalyst. The optimum conditions for the benzoylation of toluene were determined and at 373 K, 100% conversion and 89% selectivity for the para-product (i.e. 4-methylbenzonphenone) were obtained.

关键词: rice husk, sol-gel, indium, Friedel-Craft benzoylation, Toluene

Abstract: Indium incorporated silica samples with different indium contents were synthesized using a template free sol-gel method. The silica used was extracted from rice husk (RH) and the resulting catalyst was labeled as RH-xIn (x = 5%, 10%, 15%, and 20%). From the N₂ adsorption analysis the presence of type IV isotherm in RH-blank and RH-xIn indicated the mesoporous nature of the catalysts. In the XRD pattern, a broad band at ca. 2θ = 25° was observed for all the catalysts which showed them to be amorphous. TEM micrographs revealed that the material is composed of nanoparticles. Friedel-Craft benzoylation of toluene was carried out using the RH-xIn catalyst. The optimum conditions for the benzoylation of toluene were determined and at 373 K, 100% conversion and 89% selectivity for the para-product (i.e. 4-methylbenzophenone) were obtained.

Key words: rice husk, sol-gel, indium, Friedel-Craft benzoylation, Toluene

Farook ADAM, Kei Lin SEK. Heterogenization of Indium for the Friedel-Craft Benzoylation of Toluene[J]. 催化学报, 2012, 33(11): 1802-1808.

Farook ADAM, Kei Lin SEK. Heterogenization of Indium for the Friedel-Craft Benzoylation of Toluene[J]. Chinese Journal of Catalysis, 2012, 33(11): 1802-1808.

×
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(11)60453-1

https://www.cjcatal.com/CN/Y2012/V33/I11/1802

参考文献

1 Liou T H, Yang C C. Mater Sci Eng B, 2011, 176: 521
2 Kim K D, Kim H T. J Sol-Gel Sci Technol, 2002, 25: 183
3 Markowitz M A, Schoen P E, Kust P, Gaber B P. Colloid Sur-face A, 1999, 150: 85
4 Nassar E J, Nassor E C De O, Ávila L R, Pereira P F S, Cestari A, Luz L M, Ciuffi K J, Calefi P S. J Sol-Gel Sci Technol, 2007, 43: 21
5 Baccile N, Babonneau F, Thomas B. J Mater Chem, 2009, 19: 8537
6 Moleski R, Leontidis E, Krumeich F. J Colloid Interface Sci, 2006, 302: 246
7 Chiarakorn S, Areerob T, Grisdanurak N. Sci Tech Adv Mater, 2007, 8: 110
8 Ahmed A E, Adam F. Microporous Mesoporous Mater, 2007, 103: 284
9 Amutha K, Ravibaskar R, Sivakumar G. Int J Technol Appl, 2010, 4: 61
10 Adam F, Chew T S, Andas J. J Sol-Gel Sci Technol, 2011, 59: 580
11 Dimitriev Y, Ivanova Y, Iordanova R. J Univ Chem Technol Metallurgy, 2008, 43: 181
12 Singh A P, Bhattacharya D, Sharma S. J Mol Catal A, 1995, 102: 139
13 Gawande M B, Deshpande S S, Sonavane S U, Jayaram R V. J Mol Catal A, 2005, 241: 151
14 Laidlawa P, Bethell P D, Brown S M, Hutchings G J. J Mol Catal A 2001, 174: 187
15 Arata K, Nakamura H, Shouji M. Appl Catal A, 2000, 197: 213
16 Choudhary V R, Jana S K, Narkhede V S. Appl Catal A, 2002, 235: 207
17 Nguyen L T L, Le K K A, Phan N T S. Chin J Catal, 2012, 33: 688
18 Bordoloi A, Mathew N T, Devassy B M, Mirajkar S P, Halligudi S B. J Mol Catal A, 2006, 247: 58
19 Liu E, Locke A J, Frost R L, Martens W N. J Mol Catal A, 2012, 353-354: 95
20 Choudhary V R, Jha R. Appl Catal A, 2007, 333: 42
21 Choudhary V R, Jana S K. J Mol Catal A, 2002, 184: 247
22 Jang D O, Moon K S, Choa D H, Kim J S. Tetrahedron Lett, 2006, 47: 6063
23 Wildermann A, Foricher Y, Netscher Y T, Bonrath W. Pure Appl Chem, 2007, 79, 11: 1839
24 Miyai T, Onishi Y, Baba A. Tetrahedron, 1999, 55: 1017
25 Miyai T, Onishi Y, Baba A. Tetrahedron Lett, 1998, 39: 6291
26 Xia Y, Dai H, Jiang H, Zhang L, Deng J, Liu Y. J Hazard Ma-ter, 2011, 186: 84
27 Chang S S, Clair B, Ruelle J, Beauchéne J, FRenzo F D, Quignard F, Zhao G J, Yamamoto H, Gril J. J Exp Bot, 2009, 60, 11: 3023
28 Vinu A, Krithiga T, Gokulakrishnan N, Srinivasu P, Anandan S, Ariga K, Murugesan V, Balasubramanian V V, Mori T. Microporous Mesoporous Mater, 2007, 100: 87
29 Waghmare A A, Bose P, Pati H N. Pharma Chem, 2010, 2: 212

[1]	Wan-Kuen Jo, Hyun-Jung Kang. Aluminum sheet-based S-doped TiO₂ for photocatalytic decomposition of toxic organic vapors[J]. 催化学报, 2014, 35(7): 1189-1195.
[2]	Saeed Farhadi, Kosar Jahanara. ZnAl₂O₄@SiO₂ nanocomposite catalyst for the acetylation of alcohols, phenols and amines with acetic anhydride under solvent-free conditions[J]. 催化学报, 2014, 35(3): 368-375.
[3]	Sharifah Bee Abd Hamid, Tong Ling Tan, Chin Wei Lai, Emy Marlina Samsudin. Multiwalled carbon nanotube/TiO₂ nanocomposite as a highly active photocatalyst for photodegradation of Reactive Black 5 dye[J]. 催化学报, 2014, 35(12): 2014-2019.
[4]	Ehsan Amini, Mehran Rezaei, Mohammad Sadeghinia. Low temperature CO oxidation over mesoporous CuFe₂O₄nanopowders synthesized by a novel sol-gel method[J]. 催化学报, 2013, 34(9): 1762-1767.
[5]	Muhammad Asgher, Bazgha Aslam, Hafiz Muhammad Nasir Iqbal. Novel catalytic and effluent decolorization functionalities of sol-gel immobilized Pleurotus ostreatus IBL-02 manganese peroxidase produced from bio-processing of wheat straw[J]. 催化学报, 2013, 34(9): 1756-1761.
[6]	Ho-Hwan CHUN, Wan-Kuen JO. Visible-light-responsive carbon-embedded photocatalyst coupled with plug-flow reactor for decomposition of vaporous aromatics[J]. 催化学报, 2013, 34(6): 1256-1261.
[7]	Zsolt PAP, Andreea RADU, Izabella Jolan HIDI, Georgian MELINTE, Lucian DIAMANDESCU, Traian POPESCU, Lucian BAIA, Virginia DANCIU, Monica BAIA. 金纳米粒子在TiO₂气凝胶基质上的行为: 光催化活性评价和结构研究[J]. 催化学报, 2013, 34(4): 734-740.
[8]	Farhad Shirini, Somayeh Akbari-Dadamahaleh, Ali Mohammad-Khah. Rice husk ash supported FeCl₂·2H₂O：A mild and highly efficient heterogeneous catalyst for the synthesis of polysubstituted quinolines by Friedländer heteroannulation[J]. 催化学报, 2013, 34(12): 2200-2208.
[9]	Hakimeh MIRZAEI, Abolghasem DAVOODNIA. Microwave Assisted Sol-Gel Synthesis of MgO Nanoparticles and Their Catalytic Activity in the Synthesis of Hantzsch 1,4-Dihydropyridines[J]. 催化学报, 2012, 33(9): 1502-1507.
[10]	Ezzat RAFIEE, Shabnam SHAHEBRAHIMI. Nano Silica with High Surface Area from Rice Husk as a Support for 12-Tungstophosphoric Acid: An Efficient Nano Catalyst in Some Organic Reactions[J]. 催化学报, 2012, 33(8): 1326-1333.
[11]	G. R. MORADI*, F. KHOSRAVIAN, M. RAHMANZADEH. Effect of Partial Substitution of Ni by Cu in LaNiO₃ Perovskite Catalyst for Dry Methane Reforming[J]. 催化学报, 2012, 33(5): 797-801.
[12]	Farook ADAM, Thiam-Seng CHEW, Jeyashelly ANDAS. Liquid Phase Oxidation of Acetophenone over Rice Husk Silica Vanadium Catalyst[J]. 催化学报, 2012, 33(3): 518-522.
[13]	Madhukar NAVGIRE, Ajeet YELWANDE, Deepak TAYDE, Balasaheb ARBAD, Machhindra LANDE. Photodegradation of Molasses by a MoO₃-TiO₂ Nanocrystalline Composite Material[J]. 催化学报, 2012, 33(2): 261-266.
[14]	Taymaz TABARI, Haman TAVAKKOLI. Fabrication and Characterization of Perovskite-type Oxide LaFe_0.9Co_0.1O₃ Nanoparticles and Its Performance in Aerobic Oxidation of Thiols to Disulfide[J]. 催化学报, 2012, 33(11): 1791-1796.
[15]	Seyed Ali HOSSEINI, Mohammad Taghi SADEGHI-SORKHANI, Leila KAFI-AHMADI, Abdolali ALEMI, Aligholi NIAEI, Dariush SALARI. Synthesis, Characterization, and Catalytic Activity of Nanocrystalline La_1-xEuxFeO₃ during the Combustion of Toluene[J]. 催化学报, 2011, 32(9): 1465-1468.