Synthesis of Modified Mesoporous Zeolites FSM-16 Series and Their Catalytic Performance for Michael Addition of 2-Methyl Indole and Cyclohex-2-enone

doi:10.3724/SP.J.1095.2014.30458

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Synthesis of Modified Mesoporous Zeolites FSM-16 Series and Their Catalytic Performance for Michael Addition of 2-Methyl Indole and Cyclohex-2-enone

LIU Jie, QIU Jun^*

(College of Chemistry and Pharmaceutical Engineering,Jilin Institute of Chemical Technology,Jilin 132022,China)

Received:2013-09-10 Revised:2013-11-25 Published:2014-07-10 Online:2014-07-10
Contact: Jun QIU

Abstract

Abstract: The modified mesoporous zeolites Al-FSM-16, Zr-FSM-16, and Al-Zr-ESM-16 were synthesized using cetyltrimethyl ammonium bromide(CTMAB) as the template, and characterized by XRD, IR, SEM, and BET. These catalysts were evaluated for synthesis of 3-(2-methyl-1H-indol-3-yl) cyclohexanone by catalytic Michael addition of 2-methylindole to cyclohex-2-enone under a solvent free condition. Al and Zr doping into the skeleton of the molecular sieve leads to larger pores molecular sieve, but the skeleton structure does not change significantly. Al or Zr doping increases the catalytic activity of FSM-16 molecular sieves and the Zr-FSM-16 molecular sieve has better activity. Under the following optimum reaction conditions: catalyst dosage 7.5%, molar ratio of cyclohex-2-enone to 2-methylindole being 1∶1.1, reaction temperature 80 ℃ and reaction time 120 min, the yield of 3-(2-methyl-1H-indol-3-yl) cyclohexanone is up to 75.4%.

Key words: modified mesoporous zeolites FSM-16, catalysis, methyl indole, cyclohex-enone, Michael addition, (methyl-1H-indol-yl)cyclohexanone

CLC Number:

O643

LIU Jie, QIU Jun*. Synthesis of Modified Mesoporous Zeolites FSM-16 Series and Their Catalytic Performance for Michael Addition of 2-Methyl Indole and Cyclohex-2-enone[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2014.30458.

References

[1] Yanagisawa T,Shimizu T,Kuroda K,et al. The Preparation of Alkyltrimethylammonium -Kanemite Complexes and Their Conversion to Microporous Materials[J]. Bull Chem Soc Jpn,1990,63(4):988-992.

[2] Inagaki S,Koiwai A，Suzuki N,et al. Syntheses of Highly Ordered Mesoporous Materials, FSM-16, Derived from Kanemite[J]. Bull Chem Soc Jpn,1996,65(5):1449-1557.

[3] Chatterjee M,Iwasaki T,Onodera Y,et al. Hydrothermal Synthesis and Characterization of Copper Containing Crystalline Silicate Mesoporous Materials from Gel Mixture[J]. Appl Clay Sci,2004,25(3/4):195-205.

[4] JIANG Guodong,LIAO Shijun,JIAN Qifei. Synthesis of Zr-FSM-16 Mesoporous Zeolites and Its Catalytic Performance for Hydroxylation of Benzene[J]. Chinese J Catal,2005,26(2):123-126(in Chinese).

江国东，廖世军，简弃非. Zr-FSM-16中孔分子筛的合成及其对苯羟基化的催化性能[J]. 催化学报，2005,26(2):123-126.

[5] DU Jimin,QI Qiaofang,LIU Jingling. Synthesis, Characterization and Catalytic Activities of Metal Modified FSM-16 Molecular Sieves[J]. J Salt Lake Res,2010,18(2):47-51(in Chinese).

杜记民，齐乔芳，刘景玲. 金属改性的FSM-16分子筛的合成、表征及催化性能研究[J]. 盐湖研究，2010,18(2):47-51.

[6] GAO Xiaohan，XU Jie. Hydroxylation of Benzene with H2O2 to Phenol over Zeolite FSM-16 Modified by Metal[J]. Fine Chem,2007,24(6):621-624(in Chinese).

高肖汉，徐杰. 金属改性的FSM-16分子筛催化苯与过氧化氢合成苯酚[J]. 精细化工，2007,24(6):621-624.

[7] ZHOU Qun,SUN Fang,CHUAI Bingjie,et al. Synthesis and Characterization of Zeolite FSM-16 and TiO2/FSM-16[J]. Chem J Chinese Univ,2001,22(8):1400-1402(in Chinese).

周群，孙芳，揣冰洁，等. FSM-16沸石和纳米TiO2/FSM-16沸石的合成与光谱表征[J]. 高等化学学报，2001,22(8):1400-1402.

[8] Habib F,Nasser I,Massoumeh J,et al. ZrOCl2·8H2O as a Highly Efficient and the Moisture Tolerant Lewis Acid Catalyst for Michael Addition of Amines and Indoles to α,β-Unsaturated Ketones Under Solvent-free Conditions[J]. J Mol Catal A:Chem,2006,252(1/2):150-155.

[9] Thangaraj A,Kumar R,Mirajkar S P,et al. Catalytic Properties of Crystalline Titanium Silicalites:I.Synthesis and Characterization of Titanium-rich Zeolites with MFI Structure[J]. J Catal,1991,130(1):1-8.

[1]	Yi-Cheng ZHANG, Fei ZHA, Xiao-Hua TANG, Yue CHANG, Hai-Feng TIAN, Xiao-Jun GUO. Research Progress of Heterogeneous Catalytic Preparation of Organic Peroxides [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 769-788.
[2]	Xing-Quan XIONG, Hui ZHANG, Li-Zhu GAO. Progress in Chemical Modification and Application of Lignin [J]. Chinese Journal of Applied Chemistry, 2023, 40(6): 806-819.
[3]	Xue-Bo LEI, Hui-Jing LIU, He-Yu DING, Guo-Dong SHEN, Run-Jun SUN. Research Progress on Photocatalysts for Degradation of Organic Pollutants in Printing and Dyeing Wastewater [J]. Chinese Journal of Applied Chemistry, 2023, 40(5): 681-696.
[4]	Zhen-Bang LIU, Shuo ZHANG, Yu BAO, Ying-Ming MA, Wei-Qi LIANG, Wei WANG, Ying HE, Li NIU. Progress of Application Research on Cheminformatics in Deep Learning [J]. Chinese Journal of Applied Chemistry, 2023, 40(3): 360-373.
[5]	Yan-Qin CHENG, Zhuo-Xi LI, You-Di WANG, Juan-Juan XU, Zheng BIAN. Structurally Simplified 4-Hydroxyprolinamide for Highly Efficient Asymmetric Michael Addition of Aldehydes to Nitroolefins [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 146-154.
[6]	Hong-Mei BI. Research Progress of Assembly of Phospholipid Tube in Vitro and Its Potential Application in the Field of Biology and Chemistry [J]. Chinese Journal of Applied Chemistry, 2023, 40(1): 40-51.
[7]	Ye LIU, Shao-Bo GUO, Yan-Li LIANG, Hong-Guang GE, Jian-Qi MA, Zhi-Feng LIU, Bo LIU. Preparation and Catalytic Performance of Core‑Shell CuFe₂O₄@NH₂@Pt Nanocomposites [J]. Chinese Journal of Applied Chemistry, 2022, 39(8): 1237-1245.
[8]	Wang LI. Morphology Control and Catalytic Dehydrogenation Performance of Zeolitic Imidazolate Frameworks⁃8 [J]. Chinese Journal of Applied Chemistry, 2022, 39(7): 1065-1072.
[9]	Chao ZHANG. Research Prospect of Single Atom Catalysts Towards Electrocatalytic Reduction of Carbon Dioxide [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 871-887.
[10]	Yan WANG, Shu-Cong ZHANG, Xing-Kun WANG, Zhi-Cheng LIU, Huan-Lei WANG, Ming-Hua HUANG. Research Progress on Transition Metal⁃Based Catalysts for Hydrogen Evolution Reaction via Seawater Electrolysis [J]. Chinese Journal of Applied Chemistry, 2022, 39(6): 927-940.
[11]	Ya-Li FENG, Lie-Jin ZHOU, Zhong-Yan CAO. Transition Metal⁃Catalyzed Cross⁃Coupling Reactions of Alkenyl Fluorides： Advances and Perspectives [J]. Chinese Journal of Applied Chemistry, 2022, 39(5): 749-759.
[12]	Ke WANG, Xiao WANG, Shu-Yan SONG. Recent Advances in Direct Oxidation of Methane to Methanol [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 540-558.
[13]	Lin-Jie SHANG, Jiang LIU, Ya-Qian LAN. Covalent Organic Framework Materials for Photo/ Electrocatalytic Carbon Dioxide Reduction [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 559-584.
[14]	Xue-Ting WU, Yang YU, Shu-Yan SONG, Hong-Jie ZHANG. Artificial Carbon Sequestration Technology—Research Progress on the Catalysts for Thermal Catalytic Reduction of CO₂ [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 599-615.
[15]	Jia-He WANG, Da-Yong LIU, Wei LIU, Lin WANG, Biao DONG. Research Progress on Photocatalytic Antibacterial Application of TiO₂ Nano Materials [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 629-646.

Synthesis of Modified Mesoporous Zeolites FSM-16 Series and Their Catalytic Performance for Michael Addition of 2-Methyl Indole and Cyclohex-2-enone

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments