A new method for green production of 2-aminomethylpiperidine from bio-renewable 2,5-bis(aminomethyl)furan

被引：4

作者：

Zhang, Shuxing ^{[1
]}

Ding, Xiaoshu ^{[1
]}

Wang, Yanji ^{[1
]}

机构：

[1] Hebei Univ Technol, Hebei Prov Key Lab Green Chem Technol & High Effic, Tianjin 300130, Peoples R China

来源：

GREEN CHEMISTRY | 2024年 / 26卷 / 04期

基金：

中国国家自然科学基金;

关键词：

REDUCTIVE AMINATION; HYDROGENOLYSIS; HYDROGENATION; 5-AMINO-1-PENTANOL; NANOPARTICLES; COMPLEXES; CATALYSTS;

D O I：

10.1039/d3gc03082b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

2-Aminomethylpiperidine is an important organic compound, which is the basic raw material for the synthesis of flecainide acetate. In this paper, a new method for synthesizing 2-aminomethylpiperidine by selective hydrogenolysis of bio-renewable 2,5-bis(aminomethyl)furan was developed. The catalytic performance of Pt catalysts supported on different carriers (including gamma-Al2O3, ZrO2, TiO2, H-ZSM-5) and several commercial hydrogenation catalysts was studied. It was found that the Pt/gamma-Al2O3 catalyst showed the best performance. The effects of the preparation method, reduction temperature and reaction parameters on the catalytic performance of the Pt/gamma-Al2O3 catalyst were studied. The results show that good Pt dispersion and more acidic sites favor the reactivity and selectivity of hydrogenolysis. The large size of Pt particles facilitates BAMF hydrogenation. The yield of 2-aminomethylpiperidine reached 72.0% at 140 degrees C and 1 MPa H2 in aqueous solution using direct hydrogen at 350 degrees C to reduce 2 wt% Pt/gamma-Al2O3 catalyst. In addition, the reaction pathways of selective hydrogenolysis of 2,5-bis(aminomethyl)furan to 2-aminomethylpiperidine were proposed. A new method for synthesizing 2-aminomethylpiperidine by selective hydrogenolysis of bio-renewable 2,5-bis(aminomethyl)furan was developed. The yield of 2-aminomethylpiperidine can reach 72% under mild conditions at 140 degrees C and 1 MPa H2 pressure.

引用

页码：2067 / 2077

页数：11

共 31 条

[1]

Antones S., 2008, CN Pat, Patent No. 101209989

[2]

Antons S., 2008, US Pat, Patent No. [20080188665A1, 20080188665]

[3] Selective hydrogenolysis of 2-furancarboxylic acid to 5-hydroxyvaleric acid derivatives over supported platinum catalysts [J].

Asano, Takehiro ;

Takagi, Hiroshi ;

Nakagawa, Yoshinao ;

Tamura, Masazumi ;

Tomishige, Keiichi .

GREEN CHEMISTRY, 2019, 21 (22) :6133-6145

[4] Alternative Monomers Based on Lignocellulose and Their Use for Polymer Production [J].

Delidovich, Irina ;

Hausoul, Peter J. C. ;

Deng, Li ;

Pfuetzenreuter, Rebecca ;

Rose, Marcus ;

Palkovits, Regina .

CHEMICAL REVIEWS, 2016, 116 (03) :1540-1599

[5] Use of Flecainide for the Treatment of Atrial Fibrillation [J].

Echt, Debra S. ;

Ruskin, Jeremy N. .

AMERICAN JOURNAL OF CARDIOLOGY, 2020, 125 (07) :1123-1133

[6] A State-of-the-Art Heterogeneous Catalyst for Efficient and General Nitrile Hydrogenation [J].

Formenti, Dario ;

Mocci, Rita ;

Atia, Hanan ;

Dastgir, Sarim ;

Anwar, Muhammad ;

Bachmann, Stephan ;

Scalone, Michelangelo ;

Junge, Kathrin ;

Beller, Matthias .

CHEMISTRY-A EUROPEAN JOURNAL, 2020, 26 (67) :15589-15595

[7] Insights on the One-Pot Formation of 1,5-Pentanediol from Furfural with Co-Al Spinel-based Nanoparticles as an Alternative to Noble Metal Catalysts [J].

Gavila, L. ;

Lahde, A. ;

Jokiniemi, J. ;

Constanti, M. ;

Medina, F. ;

del Rio, E. ;

Tichit, D. ;

Alvarez, M. G. .

CHEMCATCHEM, 2019, 11 (19) :4944-4953

[8] Selective hydrogenolysis of bio-renewable tetrahydrofurfurylamine to piperidine on ReOx-modified Rh catalysts [J].

Hong, Cheng-Bin ;

Li, Guoliang ;

Liu, Haichao .

GREEN CHEMISTRY, 2023, 25 (09) :3515-3523

[9] Metal-support interactions in Pt/Al2O3 and Pd/Al2O3 catalysts for CO oxidation [J].

Ivanova, A. S. ;

Slavinskaya, E. M. ;

Gulyaev, R. V. ;

Zaikovskii, V. I. ;

Stonkus, O. A. ;

Danilova, I. G. ;

Plyasova, L. M. ;

Polukhina, I. A. ;

Boronin, A. I. .

APPLIED CATALYSIS B-ENVIRONMENTAL, 2010, 97 (1-2) :57-71

[10] Electronic Effect of Ruthenium Nanoparticles on Efficient Reductive Amination of Carbonyl Compounds [J].

Komanoya, Tasuku ;

Kinemura, Takashi ;

kita, Yusuke ;

Kamata, Keigo ;

Hara, Michikazu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (33) :11493-11499

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