A Novel Gemini Sulfonic Ionic Liquid Immobilized MCM-41 as Efficient Catalyst for Doebner-Von Miller Reaction to Quinoline

被引：14

作者：

Li, An ^{[1
]}

Wang, Xinyang ^{[1
]}

Li, Yuhang ^{[1
]}

Luo, Caiwu ^{[2
]}

Zhang, Jiance ^{[1
]}

Liu, Kun ^{[1
]}

Zhang, Cen ^{[1
]}

Zhou, Congshan ^{[1
]}

机构：

[1] Hunan Inst Sci & Technol, Coll Chem & Chem Engn, Yueyang 414000, Hunan, Peoples R China

[2] Univ South China, Coll Environm Protect & Safety Engn, Hengyang 421001, Hunan, Peoples R China

来源：

CHEMCATCHEM | 2021年 / 13卷 / 17期

基金：

中国国家自然科学基金;

关键词：

heterogeneous catalysis; ionic liquids; liquid phase synthesis; mesoporous materials; ordered mesopore; gemini sulfonic ionic liquid; immobilization; synergistic catalysis; quinoline; COLLISION-INDUCED DISSOCIATION; MICROWAVE-ASSISTED SYNTHESIS; DONOR LIGANDS PYRIDINE; NONCOVALENT INTERACTIONS; MESOPOROUS SILICA; DERIVATIVES; 1,10-PHENANTHROLINE; ESTERIFICATION; QUINALDINES; IMIDAZOLE;

D O I：

10.1002/cctc.202100424

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：

A novel 2,2 '-bipyridine-based gemini sulfonic ionic liquid was first synthesized and then immobilized on MCM-41 support (named IL1/MCM-41), which was further characterized using XRD, FT-IR, SEM, TEM, N-2-physisorption, XPS and TG techniques. These characterization results revealed that the IL1/MCM-41 presented a whole ordered mesoporous structure, excellent thermal stability as well as the interaction between ionic liquid with MCM-41. Catalytic activity of the obtained IL1/MCM-41 was systematically evaluated for the Doebner-Von Miller reaction to generate quinoline. Compared to conventional imidazole-type single sulfonic ionic liquid supported on MCM-41 (named IL2/MCM-41), IL1/MCM-41 exhibited higher catalytic activity and better reusability, which was probably due to the synergistic catalytic effect of the dual sulfonic acid group on IL2 and the stronger interaction between dipyridine ring of ionic liquid with MCM-41 support, respectively. Meanwhile, a plausible reaction routes for the synergistic catalytic action of dual sulfonic acid to quinoline over the IL1/MCM-41 catalyst was also proposed in this paper.

引用

页码：3772 / 3780

页数：9

共 53 条

[31] Microwave-assisted simple synthesis of quinolines from anilines and alkyl vinyl ketones on the surface of silica gel in the presence of indium(III) chloride [J].

Ranu, BC ;

Hajra, A ;

Jana, U .

TETRAHEDRON LETTERS, 2000, 41 (04) :531-533

[32] Synthesis and characterization of micro-mesoporous MCM-41 using various ionic liquids as co-templates [J].

Sanaeishoar, Haleh ;

Sabbaghan, Maryam ;

Mohave, Fouad .

MICROPOROUS AND MESOPOROUS MATERIALS, 2015, 217 :219-224

[33] Direct synthesis, characterization and catalytic application of SBA-15 mesoporous silica with heteropolyacid incorporated into their framework [J].

Sheng, Xiaoli ;

Kong, Jie ;

Zhou, Yuming ;

Zhang, Yiwei ;

Zhang, Zewu ;

Zhou, Shijian .

MICROPOROUS AND MESOPOROUS MATERIALS, 2014, 187 :7-13

[34] Synthesis of quinaldines and lepidines by a Doebner-Miller reaction under thermal and microwave irradiation conditions using phosphotungstic acid [J].

Sivaprasad, G ;

Rajesh, R ;

Perumal, PT .

TETRAHEDRON LETTERS, 2006, 47 (11) :1783-1785

[35] Bronsted acid ionic liquid-catalyzed reductive Friedel-Crafts alkylation of indoles and cyclic ketones without using an external reductant [J].

Taheri, Amir ;

Lai, Bingbing ;

Cheng Chenga ;

Gu, Yanlong .

GREEN CHEMISTRY, 2015, 17 (02) :812-816

[36]

Testa F, 2004, STUD SURF SCI CATAL, V154, P424

[37] Improved syntheses of quinaldines and 3-alkyl quinolines [J].

Utermohlen, WP .

JOURNAL OF ORGANIC CHEMISTRY, 1943, 8 (06) :544-549

[38] Production of eco-friendly poly(oxymethylene) dimethyl ethers catalyzed by acidic ionic liquid: A kinetic investigation [J].

Wang, Dan ;

Zhao, Feng ;

Zhu, Gangli ;

Xia, Chungu .

CHEMICAL ENGINEERING JOURNAL, 2018, 334 :2616-2624

[39] Bronsted-Lewis dual acidic ionic liquid immobilized on mesoporous silica materials as an efficient cooperative catalyst for Mannich reactions [J].

Wang, Hong Bo ;

Yao, Nan ;

Wang, Long ;

Hu, Yu Lin .

NEW JOURNAL OF CHEMISTRY, 2017, 41 (19) :10528-10531

[40] Ionic liquids in catalysis [J].

Welton, T .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2459-2477

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