Grafted Polyethylene Glycol-Graphene Oxide as a Novel Triphase Catalyst for Carbenes and Nucleophilic Substitution Reactions

被引:10
作者
Yang, Xiaohai [1 ]
Zhai, Jie [1 ]
Xu, Tongchun [1 ]
Xue, Bing [1 ]
Zhu, Jie [1 ]
Li, Yongxin [1 ]
机构
[1] Changzhou Univ, Sch Petrochem Engn, Jiangsu Key Lab Adv Catalyt Mat & Technol, Changzhou 213164, Peoples R China
基金
中国国家自然科学基金;
关键词
Polyethylene glycol; Graphene oxide; Triphase catalyst; Carbenes reaction; Nucleophilic substitution; PHASE-TRANSFER CATALYST; EFFICIENT; DERIVATIVES; SUPPORTS;
D O I
10.1007/s10562-019-02849-w
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
Separation and reusability had been main problems for the using of polyethylene glycol (PEG) as phase transfer catalysts (PTCs). To solve these problems, PEG was firstly and successfully grafted on graphene oxide (GO) using BF3 center dot C2H5OC2H5 as Lewis acid catalyst. The solid GO-PEG composites were systemically investigated by characterization techniques (TG, FT-IR, XPS, ICP-AES etc.) and then applied to some carbenes and nucleophilic substitution reactions as novel triphase catalysts. As the results, GO-PEG showed not only equally excellent catalytic activity (>= 93% yield of 7,7-dichlorobicyclo[4.1.0]heptane and iodooctane) but also incomparable reusability (>= 85% yield of iodooctane after using for four times) in comparison with traditional PTCs (PEG). [GRAPHICS] .
引用
收藏
页码:2767 / 2775
页数:9
相关论文
共 28 条
[1]   Synthesis of dialkyl peroxides in the presence of polyethylene glycol or its derivatives as phase-transfer catalyst in liquid-liquid-liquid system [J].
Baj, Stefan ;
Siewniak, Agnieszka .
APPLIED CATALYSIS A-GENERAL, 2007, 321 (02) :175-179
[2]   Polyethylene glycol and solutions of polyethylene glycol as green reaction media [J].
Chen, J ;
Spear, SK ;
Huddleston, JG ;
Rogers, RD .
GREEN CHEMISTRY, 2005, 7 (02) :64-82
[3]   Graphene oxide as an acid catalyst for the room temperature ring opening of epoxides [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Concepcion, Patricia ;
Fornes, Vicente ;
Garcia, Hermenegildo .
CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5443-5445
[4]   Polyethylene glycol (PEG) as a reusable solvent medium for an asymmetric organocatalytic Michael addition. Application to the synthesis of bioactive compounds [J].
Feu, Karla S. ;
de la Torre, Alexander F. ;
Silva, Sandrina ;
de Moraes Junior, Marco A. F. ;
Correa, Arlene G. ;
Paixao, Marcio W. .
GREEN CHEMISTRY, 2014, 16 (06) :3169-3174
[5]   Preparation of Polymer-Supported Polyethylene Glycol and Phase-Transfer Catalytic Activity in Benzoate Synthesis [J].
Gao, Baojiao ;
Zhuang, Rubin ;
Guo, Jianfeng .
AICHE JOURNAL, 2010, 56 (03) :729-736
[6]   Engineered Graphene Materials: Synthesis and Applications for Polymer Electrolyte Membrane Fuel Cells [J].
He, Daping ;
Tang, Haolin ;
Kou, Zongkui ;
Pan, Mu ;
Sun, Xueliang ;
Zhang, Jiujun ;
Mu, Shichun .
ADVANCED MATERIALS, 2017, 29 (20)
[7]   Simultaneous sulfonation and reduction of graphene oxide as highly efficient supports for metal nanocatalysts [J].
He, Daping ;
Kou, Zongkui ;
Xiong, Yuli ;
Cheng, Kun ;
Chen, Xu ;
Pan, Mu ;
Mu, Shichun .
CARBON, 2014, 66 :312-319
[8]   Nitrogen-doped reduced graphene oxide supports for noble metal catalysts with greatly enhanced activity and stability [J].
He, Daping ;
Jiang, Yulin ;
Lv, Haifeng ;
Pan, Mu ;
Mu, Shichun .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2013, 132 :379-388
[9]   Graphene oxide stabilized Cu2O for shape selective nanocatalysis [J].
Hong, Chenglin ;
Jin, Xin ;
Totleben, Jennifer ;
Lohrman, Jessica ;
Harak, Ethan ;
Subramaniam, Bala ;
Chaudhari, Raghunath V. ;
Ren, Shenqiang .
JOURNAL OF MATERIALS CHEMISTRY A, 2014, 2 (20) :7147-7151
[10]   Poly(ethylene glycol) Grafted onto Dowex Resin: An Efficient, Recyclable, and Mild Polymer-Supported Phase Transfer Catalyst for the Regioselective Azidolysis of Epoxides in Water [J].
Kiasat, Ali Reza ;
Badri, Rashid ;
Zargar, Behrouz ;
Sayyahi, Soheil .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (21) :8382-8385