Citation: Yan-Xi Cui, Li-Dong Sun, Qi Sun, Lei Shi. Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K₂O[J]. Chinese Chemical Letters, ;2013, 24(12): 1127-1129. shu

Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K₂O

1.
Institute of Chemistry for Functionalized Materials, Liaoning Normal University, Dalian 116029, China

Corresponding author: Lei Shi,
Received Date: 26 March 2013
Available Online: 13 June 2013
Fund Project: We gratefully acknowledge the financial support provided by the National Natural Science Foundation of China (No. 21173110). (No. 21173110)

The vapor-phase synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K₂O was investigated. The catalysts were characterized by X-ray diffraction (XRD) and the temperatureprogrammed desorption of ammonia (NH3-TPD). The effect of the reaction temperature on the activity and selectivity of Cu/NaY-K₂O catalyst was also investigated. The results indicated that the addition of K₂O to Cu/NaY increased the selectivity of the catalyst remarkably because the amount of middle-strong acid sites decreased clearly. The decrease of the reaction temperature was beneficial for the increase of 3- methylindole selectivity. Over Cu/NaY-K₂O, the selectivity of 3-methylindole reached 75% and the yield of the target product was up to 47% at 220℃. A probable catalytic mechanism for the synthesis of 3- methylindole from glycerol and aniline was proposed.
- 3-Methylindole,
- Cu/NaY,
- K₂O promoter,
- Glycerol,
- Aniline
1. [1]
  [1] M. Howe-Grant, Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed, John Wiley & Sons, New York, 1995, pp. 161-162.
2. [2]
  [2] M. Howe-Grant, Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed, John Wiley & Sons, New York, 1989, pp. 213-214.
3. [3]
  [3] B.B. Aggarwal, S. Shishodia, Molecular targets of dietary agents for prevention and therapy of cancer, Biochem. Pharm. 71 (2006) 1397-1421.
4. [4]
  [4] Z.A. Kaplanclkl, G. Turan-Zitouni, A. Özdemir, G. Revial, New triazole and triazolothiadiazine derivatives as possible antimicrobial agents, Eur. J. Med. Chem. 43 (2008) 155-159.
5. [5]
  [5] G.R. Humphrey, J.T. Kuethe, Practical methodologies for the synthesis of indoles, Chem. Rev. 106 (2006) 2875-2911.
6. [6]
  [6] M. Bandini, A. Eichholzer, Catalytic functionalization of indoles in a new dimension, Angew. Chem. Int. Ed. 48 (2009) 9608-9644.
7. [7]
  [7] C.A. Simoneau, A.M. Strohl, B. Ganem, One-pot synthesis of polysubstituted indoles from aliphatic nitro compounds under mild conditions, Tetrahedron Lett. 48 (2007) 1809-1811.
8. [8]
  [8] P. Magnus, I.S. Mitchell, Synthesis of 3-methylindoles from N-aryl-N-(3-triisopropylsilylpropargyl) sulfonamides, Tetrahedron Lett. 39 (1998) 4595-4598.
9. [9]
  [9] C.S. Cho, J.H. Kim, T.J. Kim, S.C. Shim, Ruthenium-catalyzed heteroannulation of anilines with alkanolammonium chlorides leading to indoles, Tetrahedron 57 (2001) 3321-3329.
10. [10]
  [10] D.V. Gopal, B. Srinivas, V. Durgakumari, M. Subrahmanyam, Vapor-phase alkylation of indole with methanol over zeolites, Appl. Catal. A 224 (2002) 121-128.
11. [11]
  [11] M. Campanati, S. Franceschini, O. Piccolo, A. Vaccari, Reaction pathway in the vapor-phase synthesis of indole and alkylindoles, J. Catal. 232 (2005) 1-9.
12. [12]
  [12] W. Sun, D.Y. Liu, H.Y. Zhu, Q. Sun, L. Shi, A new efficient approach to 3-methylindole: vapor-phase synthesis from aniline and glycerol over Cu-based catalyst, Catal. Commun. 12 (2010) 147-150.
13. [13]
  [13] A. Behr, J. Eilting, K. Irawadi, J. Leschinski, F. Lindner, Improved utilisation of renewable resources: new important derivatives of glycerol, Green Chem. 10 (2008) 13-30.
14. [14]
  [14] A. Corma, G.W. Huber, L. Sauvanaud, P. O'Connor, Biomass to chemicals: catalytic conversion of glycerol/water mixtures into acrolein, reaction network, J. Catal. 257 (2008) 163-171.
15. [15]
  [15] C.B. Lu, J.Z. Yao, W.G. Lin, W.L. Song, Study on biomass catalytic pyrolysis for production of bio-gasoline by on-line FTIR, Chin. Chem. Lett. 18 (2007) 445-448.
16. [16]
  [16] M. Karthik, C.J. Magesh, P.T. Preumal, et al., Zeolite-catalyzed ecofriendly synthesis of vibrindole A and bis(indolyl)methanes, Appl. Catal. A 286 (2005) 137-141.
17. [17]
  [17] M.A. Alotaibi, E.F. Kozhevnikova, I.V. Kozhevnikov, Hydrogenation of methyl isobutyl ketone over bifunctional Pt-zeolite catalyst, J. Catal. 293 (2012) 141- 144.
18. [18]
  [18] H.F. Shi, Y.C. Hu, Y. Wang, H. Huang, KNaY-zeolite catalyzed dehydration of methyl lactate, Chin. Chem. Lett. 18 (2007) 476-478.
19. [19]
  [19] S.Y. Zhang, Q.Y. Liu, G.L. Fan, Highly-dispersed copper-based catalysts from Cu- Zn-Al layered double hydroxide precursor for gas-phase hydrogenation of dimethyl oxalate to ethylene glycol, Catal. Lett. 142 (2012) 1121-1127.
20. [20]
  [20] D.F. Jin, Z.Y. Hou, L.W. Zhang, X.M. Zheng, Selective synthesis of para-para0- dimethyldiphenylmethane over H-beta zeolite, Catal. Today 131 (2008) 378-384.
21. [21]
  [21] R.B. Mane, C.V. Rode, Simultaneous glycerol dehydration and in situ hydrogenolysis over Cu-Al oxide under an inert atmosphere, Green Chem. 14 (2012) 2780- 2789.
22. [22]
  [22] J. Zhao, W.Q. Yu, C. Chen, et al., Ni/NaX: a bifunctional efficient catalyst for selective hydrogenolysis of glycerol, Catal. Lett. 134 (2010) 184-189.
1. [1]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
2. [2]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
3. [3]
  Kaihui Huang , Boning Feng , Xinghua Wen , Lei Hao , Difa Xu , Guijie Liang , Rongchen Shen , Xin Li . Effective photocatalytic hydrogen evolution by Ti3C2-modified CdS synergized with N-doped C-coated Cu2O in S-scheme heterojunctions. Chinese Journal of Structural Chemistry, 2023, 42(12): 100204-100204. doi: 10.1016/j.cjsc.2023.100204
4. [4]
  Yuan ZHU , Xiaoda ZHANG , Shasha WANG , Peng WEI , Tao YI . Conditionally restricted fluorescent probe for Fe³⁺ and Cu²⁺ based on the naphthalimide structure. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 183-192. doi: 10.11862/CJIC.20240232
5. [5]
  Hao BAI , Weizhi JI , Jinyan CHEN , Hongji LI , Mingji LI . Preparation of Cu₂O/Cu-vertical graphene microelectrode and detection of uric acid/electroencephalogram. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1309-1319. doi: 10.11862/CJIC.20240001
6. [6]
  Qiang ZHAO , Zhinan GUO , Shuying LI , Junli WANG , Zuopeng LI , Zhifang JIA , Kewei WANG , Yong GUO . Cu₂O/Bi₂MoO₆ Z-type heterojunction: Construction and photocatalytic degradation properties. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 885-894. doi: 10.11862/CJIC.20230435
7. [7]
  Juan Guo , Mingyuan Fang , Qingsong Liu , Xiao Ren , Yongqiang Qiao , Mingju Chao , Erjun Liang , Qilong Gao . Zero thermal expansion in Cs₂W₃O₁₀. Chinese Chemical Letters, 2024, 35(7): 108957-. doi: 10.1016/j.cclet.2023.108957
8. [8]
  Zhijia Zhang , Shihao Sun , Yuefang Chen , Yanhao Wei , Mengmeng Zhang , Chunsheng Li , Yan Sun , Shaofei Zhang , Yong Jiang . Epitaxial growth of Cu_2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922
9. [9]
  Yi YANG , Shuang WANG , Wendan WANG , Limiao CHEN . Photocatalytic CO₂ reduction performance of Z-scheme Ag-Cu₂O/BiVO₄ photocatalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 895-906. doi: 10.11862/CJIC.20230434
10. [10]
  Renshu Huang , Jinli Chen , Xingfa Chen , Tianqi Yu , Huyi Yu , Kaien Li , Bin Li , Shibin Yin . Synergized oxygen vacancies with Mn2O3@CeO2 heterojunction as high current density catalysts for Li–O2 batteries. Chinese Journal of Structural Chemistry, 2023, 42(11): 100171-100171. doi: 10.1016/j.cjsc.2023.100171
11. [11]
  Ping Wang , Tianbao Zhang , Zhenxing Li . Reconstruction mechanism of Cu surface in CO2 reduction process. Chinese Journal of Structural Chemistry, 2024, 43(8): 100328-100328. doi: 10.1016/j.cjsc.2024.100328
12. [12]
  Wenhao Chen , Muxuan Wu , Han Chen , Lue Mo , Yirong Zhu . Cu₂Se@C thin film with three-dimensional braided structure as a cathode material for enhanced Cu²⁺ storage. Chinese Chemical Letters, 2024, 35(5): 108698-. doi: 10.1016/j.cclet.2023.108698
13. [13]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
14. [14]
  Haojie Duan , Hejingying Niu , Lina Gan , Xiaodi Duan , Shuo Shi , Li Li . Reinterpret the heterogeneous reaction of α-Fe₂O₃ and NO₂ with 2D-COS: The role of SDS, UV and SO₂. Chinese Chemical Letters, 2024, 35(6): 109038-. doi: 10.1016/j.cclet.2023.109038
15. [15]
  Cailiang Yue , Nan Sun , Yixing Qiu , Linlin Zhu , Zhiling Du , Fuqiang Liu . A direct Z-scheme 0D α-Fe₂O₃/TiO₂ heterojunction for enhanced photo-Fenton activity with low H₂O₂ consumption. Chinese Chemical Letters, 2024, 35(12): 109698-. doi: 10.1016/j.cclet.2024.109698
16. [16]
  Qinyu Zhao , Yunchao Zhao , Songjing Zhong , Zhaoyang Yue , Zhuoheng Jiang , Shaobo Wang , Quanhong Hu , Shuncheng Yao , Kaikai Wen , Linlin Li . Urchin-like piezoelectric ZnSnO₃/Cu₃P p-n heterojunction for enhanced cancer sonodynamic therapy. Chinese Chemical Letters, 2024, 35(12): 109644-. doi: 10.1016/j.cclet.2024.109644
17. [17]
  Jinyuan Cui , Tingting Yang , Teng Xu , Jin Lin , Kunlong Liu , Pengxin Liu . Hydrogen spillover enhances the selective hydrogenation of α,β-unsaturated aldehydes on the Cu-O-Ce interface. Chinese Journal of Structural Chemistry, 2025, 44(1): 100438-100438. doi: 10.1016/j.cjsc.2024.100438
18. [18]
  Dong-Xue Jiao , Hui-Li Zhang , Chao He , Si-Yu Chen , Ke Wang , Xiao-Han Zhang , Li Wei , Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304
19. [19]
  Fei ZHOU , Xiaolin JIA . Co₃O₄/TiO₂ composite photocatalyst: Preparation and synergistic degradation performance of toluene. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2232-2240. doi: 10.11862/CJIC.20240236
20. [20]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(617)
HTML views(31)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K2O

Metrics

通讯作者: 陈斌, bchen63@163.com

Highly selective synthesis of 3-methylindole from glycerol and aniline over Cu/NaY modified by K₂O