Efficient Vapor-Phase Synthesis of 3-Methylindole over Fe Promoted Cu/SiO2-Al2O3 Catalyst

doi:10.3724/SP.J.1095.2013.30045

Chinese Journal of Applied Chemistry

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Efficient Vapor-Phase Synthesis of 3-Methylindole over Fe Promoted Cu/SiO2-Al2O3 Catalyst

BAO Zhuoran¹, HUO Xiaomin², SUN Lidong¹, SUN Qi¹, SHI Lei^1*

(1.Institute of Chemistry for Functionalized Materials,Liaoning Normal University,Dalian 116029,China;
2.Dalian Institute of Product Quality Supervision & Inspection,Dalian 116021,China)

Received:2013-01-17 Revised:2013-03-03 Published:2013-10-10 Online:2013-10-10

Abstract

Abstract: 3-Methylindole was synthesized by vapor-phase method from aniline and biomass-derived glycerol over Fe promoted Cu/SiO2-Al2O3 catalyst. The catalysts were characterized by X-ray photoelectron spectroscopy(XPS), H2 temperature-programmed-reduction(H2-TPR), X-ray diffraction(XRD), transmission electron microscopy(TEM), inductively coupled plasma(ICP) emission spectroscopy, temperature-programmed-desorption of ammonia(NH3-TPD) and thermogravimetric(TG) analysis techniques. The results indicated that the addition of Fe to Cu/SiO2-Al2O3 could not only increase the activity and selectivity clearly, but also improve the stability of the catalyst remarkably. Over Cu-Fe/SiO2-Al2O3, the yield of 3-methylindole reached 48% after three hours reaction and the catalyst could be reused by regeneration without obvious loss of the yield even after 43 h reaction. The characterizations revealed that the addition of Fe to Cu/SiO2-Al2O3 could reinforce the interaction between copper and the support, which greatly improved the dispersion of Cu particles on the surface of the support and efficiently decreased the loss of copper component during the reaction. Furthermore, Fe promoter could decrease the amount of middlestrong acid sites remarkably and increase the amount of the weak acid sites of the catalyst, which was propitious to the high selectivity of 3-methylindole and inhibited the formation of the coke.

Key words: Cu/SiO2-Al2O3, iron promoter, methylindole, Glycerol, aniline

CLC Number:

O643.3

BAO Zhuoran1, HUO Xiaomin2, SUN Lidong1, SUN Qi1, SHI Lei1*. Efficient Vapor-Phase Synthesis of 3-Methylindole over Fe Promoted Cu/SiO2-Al2O3 Catalyst[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.30045.

References

[1] Howe-Grant M. Kirk-Othmer Encyclopedia of Chemical Technology[M]. 4th Ed. New York:John Wiley & Sons,1995:161.

[2] Howe-Grant M. Kirk-Othmer Encyclopedia of Chemical Technology[M]. 3rd Ed. New York:John Wiley & Sons,1989:213.

[3] Aggarwal B B,Shishodia S. Molecular Targets of Dietary Agents for Prevention and Therapy of Cancer[J]. Biochem Pharm,2006,71(10):1397-1421.

[4] Kaplanclkl Z A,Turan-Zitouni G,zdemir A,et al. New Triazole and Triazolothiadiazine Derivatives as Possible Antimicrobial Agents[J]. Eur J Med Chem,2008,43(1):155-159.

[5] Humphrey G R,Kuethe J T. Practical Methodologies for the Synthesis of Indoles[J]. Chem Rev,2006,106(7):2875-2911.

[6] Robinson B. The Fischer Indole Synthesis[J]. Chem Rev,1963,63(4):373-401.

[7] Gopal D V,Srinivas B,Durgakumari V,et al. Vapor-Phase Alkylation of Indole with Methanol over Zeolites[J]. Appl Catal A,2002,224(1/2):121-128.

[8] Campanati M,Franceschini S,Piccolo O,et al. Reaction Pathway in the Vapor-Phase Synthesis of Indole and Alkylindoles[J]. J Catal,2005,232(1):1-9.

[9] ZHENG Jiacong,LIU Jing,TAN Wei,et al. Vapor Phase Synthesis of 3-Methylindole over a Ag/SiO2 Catalyst[J]. J Chinese Catal,2008,29(12):1199-1201(in Chinese).

郑佳聪,刘静,谭伟,等. Ag/SiO2催化剂上气相合成3-甲基吲哚[J]. 催化学报,2008,29(12):1199-1201.

[10] Hu Y,Lv W H,Liu D Y,et al. Effect of ZnO on the Performance of Ag/SiO2 Catalyst for the Vapor-Phase Synthesis of 3-Methylindole[J]. J Nat Gas Chem,2009,18(4):445-448.

[11] LV Wenhui,LIU Xinghai,LIU Dongyan,et al. Vapor-Phase Synthesis of 3-Methylindole over Fe-, Co-, or Ni-Promoted Ag/SiO2 Catalysts[J]. Chinese J Catal,2009,30(12):1287-1290(in Chinese).

吕文辉,刘兴海,刘冬妍,等. 铁、钴或镍助剂促进的Ag/SiO2催化剂上气相催化合成3-甲基吲哚[J]. 催化学报,2009,30(12):1287-1290.

[12] Sun W,Liu D Y,Zhu H Y,et al. A New Efficient Approach to 3-Methylindole:Vapor-Phase Synthesis from Aniline and Glycerol over Cu-Based Catalyst[J]. Catal Commun,2010,12(2):147-150.

[13] WANG Guimin,SHAN Yuhua,ZHANG Yuanyuan,et al. Acid-Catalyzed Synthesis of Six-Membered Cyclic Acetal from Condensation of Benzaldehyde and Glycerol[J]. Chinese J Appl Chem,2010,27(7):764-768(in Chinese).

王桂敏,单玉华,张元元,等. 酸催化甘油与苯甲醛缩合制备六元环缩醛的研究[J]. 应用化学,2010,27(7):764-768.

[14] Guo X H,Li Y,Song W,et al. Glycerol Hydrogenolysis over Co Catalysts Derived from a Layered Double Hydroxide Precursor[J]. Catal Lett,2011,141(10):1458-1463.

[15] Zhu S H,Zhu Y L,Hao S L,et al. Aqueous-Phase Hydrogenolysis of Glycerol to 1,3-Propanediol over Pt-H4SiW12O40/SiO2[J]. Catal Lett,2012,142(10):267-274.

[16] ZHAO Jing,YU Weiqiang,LI Decai,et al. Catalytic Dehydration-Hydrogenation of Glycerol to 1,2-Propylene Glycol at Ambient Hydrogen Pressure[J]. Chinese J Catal,2010,31(2):74-78(in Chinese).

赵静,于维强,李德财,等. 常压两步法催化丙三醇脱水-加氢制备1,2-丙二醇[J]. 催化学报,2010,31(2):74-78.

[17] Wang N,Fang K G,Lin M G,et al. Synthesis of Higher Alcohols from Syngas over Fe/K/b-Mo2C Catalyst[J]. Catal Lett,2010,136(1):9-13.

[18] Haider M A,Gogate M R,Davis R G. Fe-Promotion of Supported Rh Catalyst for Direct Conversion of Syngas to Ethanol[J]. J Catal,2009,261(1):9-16.

[19] Wu Y Q,Lu G X,Li S B. The Role of Cu(Ⅰ) Species for Photocatalytic Hydrogen Generation over CuOx/TiO2[J]. Catal Lett,2009,133(1/2):97-105.

[20] Zhang S Y,Liu Q Y,Fan G L. Highly-Dispersed Copper-Based Catalysts from Cu-Zn-Al Layered Double Hydroxide Precursor for Gas-Phase Hydrogenation of Dimethyl Oxalate to Ethylene Glycol[J]. Catal Lett,2012,142(1):1121-1127.

[21] ZHANG Guangxu,MA Peisheng,WU Yuanxin,et al. Study on Direct Synthesis of Diphenyl Carbonate through Heterogeneous Catalysis:Ⅳ.Effects of Active Components and Their Supporting Methods on Catalyst Activity[J]. Chinese J Catal,2002,23(5):414-416(in Chinese).

张光旭,马沛生,吴元欣,等. 非均相催化一步合成碳酸二苯酯的研究:Ⅳ.活性组分及其负载方法对催化剂性能的影响[J]. 催化学报,2002,23(5):414-416.

[22] Tian P,Liu Z M,Wu Z B,et al. Characterization of Metal-Containning Moleculor Sieves and Their Catalytic Properties in the Selective Oxidation of Cyclohexane[J]. Catal Tod,2004,93/95:735-742.

Efficient Vapor-Phase Synthesis of 3-Methylindole over Fe Promoted Cu/SiO2-Al2O3 Catalyst

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