Heteropolyanion-based ionic liquid-functionalized mesoporous copolymer catalyst for Friedel-Crafts benzylation of arenes with benzyl alcohol

Chemical Engineering Journal

Volumn 254, Issue , 2014, Pages 54-62

  Li, Jing ^a   Zhou, Yu ^a   Mao, Dan ^a   Chen, Guojian ^a   Wang, Xiaochen ^a   Yang, Xiaoning ^a   Wang, Meng ^b   Peng, Luming ^b   Wang, Jun ^a  

^a NANJING TECH UNIVERSITY   (China)

^b NANJING UNIVERSITY   (China)

Author keywords

Friedel Crafts reactions; Heterogeneous catalysts; Heteropolyacids; Ionic copolymers; Ionic liquids; Mesoporous materials

Indexed keywords

COPOLYMERS; FOURIER TRANSFORM INFRARED SPECTROSCOPY; FRIEDEL-CRAFTS REACTION; HYBRID MATERIALS; MESOPOROUS MATERIALS; SCANNING ELECTRON MICROSCOPY; STABILITY; THERMOGRAVIMETRIC ANALYSIS;

12-PHOSPHOTUNGSTIC ACID; FRIEDEL-CRAFTS BENZYLATION; HETEROGENEOUS CATALYST; HETEROPOLY ACIDS; NITROGEN SORPTION ISOTHERMS; SOLVENT FREE CONDITIONS; STRUCTURAL STABILITIES; X RAY DIFFRACTOMETERS;

IONIC LIQUIDS;

EID: 84902331281     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2014.05.124     Document Type: Article

References (51)

1. Topka P., Karban J., Soukup K., Jirátová K., Šolcová O. Preparation of Al-SBA-15 pellets with low amount of additives: effect of binder content on texture and mechanical properties. Application to Friedel-Crafts alkylation. Chem. Eng. J. 2011, 168:433-440.
2. Leng K., Wang Y., Hou C., Lancelot C., Lamonier C., Rives A., Sun Y. Enhancement of catalytic performance in the benzylation of benzene with benzyl alcohol over hierarchical mordenite. J. Catal. 2013, 306:100-108.
3. Adam F., Ahmed A.E. The benzylation of xylenes using heterogeneous catalysts from rice husk ash silica modified with gallium, indium and iron. Chem. Eng. J. 2008, 145:328-334.
4. Ramesh Kumar Ch., Sai Prasad P.S., Lingaiah N., Heteropoly tungstate supported on tin oxide catalysts for liquid phase benzylation of anisole with benzyl alcohol. Appl. Catal. A 2010, 384:101-106.
5. Van der Beken S., Dejaegere E., Tehrani K.A., Paul J.S., Jacobs P.A., Baron G.V., Denayer J.F.M. Alkylation of deactivated aromatic compounds on zeolites. Adsorption, deactivation and selectivity effects in the alkylation of bromobenzene and toluene with bifunctional alkylating agents. J. Catal. 2005, 235:128-138.
6. Olah G.A., Kobayashi S., Tashiro M. Aromatic substitution. XXX. Friedel-Crafts benzylation of benzene and toluene with benzyl and substituted benzyl halides. J. Am. Chem. Soc. 1972, 94:7448-7461.
7. Chen X., Arrueboc M., Yeung K.L. Flow-synthesis of mesoporous silicas and their use in the preparation of magnetic catalysts for Knoevenagel condensation reactions. Catal. Today 2013, 204:140-147.
8. Mantri K., Komura K., Kubota Y., Sugi Y. Friedel-Crafts alkylation of aromatics with benzyl alcohols catalyzed by rare earth metal triflates supported on MCM-41 mesoporous silica. J. Mol. Catal. A 2005, 236:168-175.
9. Choudhary V.R., Jana S.K., Patil N.S., Bhargava S.K. Friedel-Crafts type benzylation and benzoylation of aromatic compounds over Hβ zeolite modified by oxides or chlorides of gallium and indium. Microporous Mesoporous Mater. 2003, 57:21-35.
10. Kang Z., Zhang X., Liu H., Qiu J., Yeung K.L. A rapid synthesis route for Sn-Beta zeolites by steam-assisted conversion and their catalytic performance in Baeyer-Villiger oxidation. Chem. Eng. J. 2013, 218:425-432.
11. Rao Y., Trudeau M., Antonelli D. Sulfated and phosphated mesoporous Nb oxide in the benzylation of anisole and toluene by benzyl alcohol. J. Am. Chem. Soc. 2006, 128:13996-13997.
12. Candu N., Wuttke S., Kemnitz E., Coman S.M., Pârvulescu V.I. Replacing benzyl chloride with benzyl alcohol in heterogeneous catalytic benzylation of aromatic compounds. Pure Appl. Chem. 2012, 84:427-437.
13. Deng M., Ling Y., Xia B., Chen Z., Zhou Y., Liu X., Yue B., He H. Synthesis of isoreticular Zinc(II)-phosphonocarboxylate frameworks and their application in the Friedel-Crafts benzylation reaction. Chem. Eur. J. 2011, 17:10323-10328.
14. Wang F., Ueda W. High catalytic efficiency of nanostructured molybdenum trioxide in the benzylation of arenes and an investigation of the reaction mechanism. Chem. Eur. J. 2009, 15:742-753.
15. 2. Chem. Eng. J. 2014, 245:65-70.
16. Hoo P.Y., Abdullah A.Z. Direct synthesis of mesoporous 12-tungstophosphoric acid SBA-15 catalyst for selective esterification of glycerol and lauric acid to monolaurate. Chem. Eng. J. 2014, 250:274-287.
17. Vafaeezadeh M., Hashemi M.M. Efficient fatty acid esterification using silica supported Brønsted acidic ionic liquid catalyst: experimental study and DFT modeling. Chem. Eng. J. 2014, 250:35-41.
18. Hallett J.P., Welton T. Room-temperature ionic liquids: solvents for synthesis and catalysis. 2. Chem. Rev. 2011, 111:3508-3576.
19. Hu L., Wu Z., Xu J., Sun Y., Lin L., Liu S. Zeolite-promoted transformation of glucose into 5-hydroxymethylfurfural in ionic liquid. Chem. Eng. J. 2014, 244:137-144.
20. Song C.E., Shim W.H., Roh E.J., Choi J.H. Scandium (III) triflate immobilised in ionic liquids: a novel and recyclable catalytic system for Friedel-Crafts alkylation of aromatic compounds with alkenes. Chem. Commun. 2000, 1695-1696.
21. Gao J., Wang J.-Q., Song Q.-W., He L.-N. Iron(III)-based ionic liquid-catalyzed regioselective benzylation of arenes and heteroarenes. Green Chem. 2011, 13:1182-1186.
22. Liu Q.Y., Wu W.L., Wang J., Ren X.Q., Wang Y.R. Characterization of 12-tungstophosphoric acid impregnated on mesoporous silica SBA-15 and its catalytic performance in isopropylation of naphthalene with isopropanol. Microporous Mesoporous Mater. 2004, 76:51-60.
23. Mukai S.R., Lin L., Masuda T., Hashimoto K. Key factors for the encapsulation of Keggin-type heteropoly acids in the supercages of Y-type zeolite. Chem. Eng. Sci. 2001, 56:779-804.
24. Sartori G., Maggi R. Update 1 of: use of solid catalysts in Friedel-Crafts acylation reactions. Chem. Rev. 2011, 111:PR181-PR214.
25. Narasimharaoa K., Brownb D.R., Leea A.F., Newmana A.D., Sirilb P.F., Tavenera S.J., Wilson K. Structure-activity relations in Cs-doped heteropolyacid catalysts for biodiesel production. J. Catal. 2007, 248:226-234.
26. Ramesh Kumar Ch., Jagadeeswaraiah K., Sai Prasad P.S., Lingaiah N. Samarium-exchanged heteropoly tungstate: an efficient solid acid catalyst for the synthesis of glycerol carbonate from glycerol and benzylation of anisole. Chem. Catal. Chem. 2012, 4:1360-1367.
27. Zhao P., Leng Y., Wang J. Heteropolyanion-paired cross-linked ionic copolymer: an efficient heterogeneous catalyst for hydroxylation of benzene with hydrogen peroxide. Chem. Eng. J. 2012, 204-206:72-78.
28. Huang W., Zhu W., Li H., Shi H., Zhu G., Liu H., Chen G. Heteropolyanion-based ionic liquid for deep desulfurization of fuels in ionic liquids. Ind. Eng. Chem. Res. 2010, 49:8998-9003.
29. Chen G., Zhou Y., Zhao P., Long Z., Wang J. Mesostructured dihydroxy-functionalized guanidinium based polyoxometalate with enhanced heterogeneous catalytic activity in epoxidation. Chem. Plus. Chem. 2013, 78:561-569.
30. 2. Chem. Eng. J. 2014, 239:19-25.
31. Leng Y., Wang J., Zhu D., Ren X., Ge H., Shen L. Heteropolyanion-based ionic liquids: reaction-induced self-separation catalysts for esterification. Angew. Chem. Int. Ed. 2009, 48:168-171.
32. Leng Y., Wang J., Zhu D., Wu Y., Zhao P. Sulfonated organic heteropolyacid salts: recyclable green solid catalysts for esterification. J. Mol. Catal. A 2009, 313:1-6.
33. Zhang W., Leng Y., Zhu D., Wu Y., Wang J. Phosphotungstic acid salt of triphenyl(3-sulfopropyl)phosphonium: an efficient and reusable solid catalyst for esterification. Catal. Commun. 2009, 11:151-154.
34. Zhang W., Leng Y., Zhao P., Wang J., Zhu D., Huang J. Heteropolyacid salts of N-methyl-2-pyrrolidonium as highly efficient and reusable catalysts for Prins reactions of styrenes with formalin. Green Chem. 2011, 13:832-834.
35. Zhang X., Mao D., Leng Y., Zhou Y., Wang J. Heterogeneous Beckmann rearrangements catalyzed by a sulfonated imidazolium salt of phosphotungstate. Catal. Lett. 2013, 143:193-199.
36. Liu F., Zheng A., Noshadi I., Xiao F. Design and synthesis of hydrophobic and stable mesoporous polymeric solid acid with ultra strong acid strength and excellent catalytic activities for biomass transformation. Appl. Catal. B 2013, 136-137:193-201.
37. Liu F., Kong W., Qi C., Zhu L., Xiao F. Design and synthesis of mesoporous polymer-based solid acid catalysts with excellent hydrophobicity and extraordinary catalytic activity. ACS Catal. 2012, 2:565-572.
38. Liang X. Novel efficient procedure for biodiesel synthesis from waste oils using solid acidic ionic liquid polymer as the catalyst. Ind. Eng. Chem. Res. 2013, 52:6894-6900.
39. Yuan J., Antonietti M. Poly(ionic liquid)s: polymers expanding classical property profiles. Polymer 2011, 52:1469-1482.
40. Liu F., Wang L., Sun Q., Zhu L., Meng X., Xiao F. Transesterification catalyzed by ionic liquids on superhydrophobic mesoporous polymers: heterogeneous catalysts that are faster than homogeneous catalysts. J. Am. Chem. Soc. 2012, 134:16948-16950.
41. Leng Y., Jiang P., Wang J. A novel Brønsted acidic heteropolyanion-based polymeric hybrid catalyst for esterification. Catal. Commun. 2012, 25:41-44.
42. Rao G.R., Rajkumar T., Varghese B. Synthesis and characterization of 1-butyl 3-methyl imidazolium phosphomolybdate molecular salt. Solid State Sci. 2009, 11:36-42.
43. Wu K.H., Wang Y.R., Hwu W.H. FTIR and TGA studies of poly(4-vinylpyridine-co-divinylbenzene)-Cu(II) complex. Polym. Degrad. Stab. 2003, 79:195-200.
44. Liu F., Meng X., Zhang Y., Ren L., Nawaz F., Xiao F. Efficient and stable solid acid catalysts synthesized from sulfonation of swelling mesoporous polydivinylbenzenes. J. Catal. 2010, 271:52-58.
45. Leng Y., Liu J., Jiang P., Wang J. Carboxylic acid-functionalized phosphovanadomolybdate- paired ionic polymer as a green heterogeneous catalyst for hydroxylation of benzene. Catal. Commun. 2013, 40:84-87.
46. Misono M. Unique acid catalysis of heteropoly compounds (heteropolyoxometalates) in the solid state. Chem. Commun. 2011, 1141-1152.
47. Xing R., Liu N., Liu Y., Wu H., Jiang Y., Chen L., He M., Wu P. Novel solid acid catalysts: sulfonic acid group-functionalized mesostructured polymers. Adv. Funct. Mater. 2007, 17:2455-2461.
48. Elavarasan P., Kondamudi K., Upadhyayula S. Kinetics of phenol alkylation with tert-butyl alcohol using sulfonic acid functional ionic liquid catalysts. Chem. Eng. J. 2011, 166:340-347.
49. Deshpande A.B., Bajpai A.R., Samant S.D. The enhanced activity of Sb after supporting on K10 in the benzylation of benzene using benzyl chloride and benzyl alcohol. Appl. Catal. A 2001, 209:229-235.
50. Mizuno N., Misono M. Heterogeneous catalysis. Chem. Rev. 1988, 98:199-218.
51. Okuhara T. Water-tolerant solid acid catalysts. Chem. Rev. 2002, 102:3641-3666.