Salen- Zr(IV) complex grafted into amine-tagged MIL-101(Cr) as a robust multifunctional catalyst for biodiesel production and organic transformation reactions

被引:67
作者
Hassan, Hassan M. A. [1 ]
Betiha, Mohamed A. [2 ]
Mohamed, Shaimaa K. [1 ]
El-Sharkawy, E. A. [1 ]
Ahmed, Emad A. [1 ]
机构
[1] Suez Univ, Dept Chem, Fac Sci, Suez, Egypt
[2] Egyptian Petr Res Inst, Nasr City 11727, Egypt
关键词
NH2-MIL-101(Cr); Zr(IV)-Sal Schiff base; Biodiesel production; Knoveonagel condensation; Friedel-Crafts acylation; POST-SYNTHETIC MODIFICATION; FUNCTIONALIZED MIL-101(CR); UNFUNCTIONALIZED OLEFINS; COORDINATION POLYMERS; SCHIFF-BASE; FRAMEWORKS; EPOXIDATION; ACID; HYDROGEN; SIZES;
D O I
10.1016/j.apsusc.2017.03.247
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The synthesis of metal-organic frameworks (MOFs), porous coordination polymers with functional groups has received immense interest due to the functional groups can offer desirable properties and allow post synthetic modification. Herein, for the first time, Zr(IV)-Sal Schiff base complex incorporated into amino-functionalized MIL-101(Cr) framework by salicylaldehyde condensing to amino group, and coordinating Zr(IV) ion have been successfully synthesized. The worthiness of the synthesized material as a catalyst has been examined for the esterification of oleic acid (free fatty acid) with methanol producing biodiesel (methyl oleate), Knoveonagel condensation reaction of aldehydes and Friedel Crafts acylation of anisole. Our findings demonstrated that Salen-Zr(IV) grafted to framework of NH2-MIL-101(Cr) as a solid acid catalyst exhibited distinct catalytic performance for the production of biodiesel by esterification of oleic acid with methanol, Knoveonagel condensation and Friedel Crafts acylation. These could be attributed to high surface area which allow high distribution of Zr(IV) species lead to a sufficient contact with the reactants species. Furthermore, the catalyst showed excellent recycling efficiency due to the strong interaction between the Zr(IV) ions and chelating groups in the NH2-MIL-101(Cr)-Sal. (C) 2017 Elsevier B.V. All rights reserved.
引用
收藏
页码:394 / 404
页数:11
相关论文
共 47 条
[1]   Bis[(amidomethyl)pyridine] Zirconium(IV) Complexes: Synthesis, Characterization, and Activity as Olefin Polymerization Catalysts [J].
Annunziata, Liana ;
Pappalardo, Daniela ;
Tedesco, Consiglia ;
Pellecchia, Claudio .
ORGANOMETALLICS, 2009, 28 (03) :688-697
[2]  
Bader N.R., 2010, Rasayan J. Chem, V3, P660
[3]   Direct covalent post-synthetic chemical modification of Cr-MIL-101 using nitrating acid [J].
Bernt, Stephan ;
Guillerm, Vincent ;
Serre, Christian ;
Stock, Norbert .
CHEMICAL COMMUNICATIONS, 2011, 47 (10) :2838-2840
[4]   A new approach to polymer-supported phosphotungstic acid: Application for glycerol acetylation using robust sustainable acidic heterogeneous-homogenous catalyst [J].
Betiha, M. A. ;
Hassan, Hassan M. A. ;
El-Sharkawy, E. A. ;
Al-Sabagh, A. M. ;
Menoufy, M. F. ;
Abdelmoniem, H-E. M. .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2016, 182 :15-25
[5]  
Bhadauria Jyoti., 2011, Journal of Chemical and Pharmaceutical Research, V3, P245
[6]   Highly enantioselective Friedel-Crafts alkylations of indoles with simple enones catalyzed by zirconium(IV)-BINOL complexes [J].
Blay, Gonzalo ;
Fernandez, Isabel ;
Pedro, Jose R. ;
Vila, Carlos .
ORGANIC LETTERS, 2007, 9 (13) :2601-2604
[7]   Synthesis, crystal structure and ethylene polymerization activity of zirconium complexes bearing mono-Cp and tridentate Schiff base [ONO] ligands [J].
Chen, QH ;
Huang, JL ;
Yu, J .
INORGANIC CHEMISTRY COMMUNICATIONS, 2005, 8 (05) :444-448
[8]   Postsynthetic Methods for the Functionalization of Metal-Organic Frameworks [J].
Cohen, Seth M. .
CHEMICAL REVIEWS, 2012, 112 (02) :970-1000
[9]   Metal-Salen Schiff base complexes in catalysis: practical aspects [J].
Cozzi, PG .
CHEMICAL SOCIETY REVIEWS, 2004, 33 (07) :410-421
[10]   Metallic and bimetallic nanocatalysts incorporated into highly porous coordination polymer MIL-101 [J].
El-Shall, M. Samy ;
Abdelsayed, Victor ;
Khder, Abd El Rahman S. ;
Hassan, Hassan M. A. ;
El-Kaderi, Hani M. ;
Reich, Thomas E. .
JOURNAL OF MATERIALS CHEMISTRY, 2009, 19 (41) :7625-7631