One-Pot Synthesis of Secondary Amines from Nitroarenes and Aldehydes on Supported Copper Catalysts in a Flow Reactor: The Effect of the Support Full article
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Kinetics and Catalysis
ISSN: 0023-1584 , E-ISSN: 1608-3210 |
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| Output data | Year: 2018, Volume: 59, Number: 5, Pages: 593-600 Pages count : 8 DOI: 10.1134/s0023158418050014 | ||||
| Tags | one-stage synthesis, secondary amines, nitroarenes, aldehydes, flow reactor, molecular hydrogen, supported copper catalysts, support effect | ||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | Federal Agency for Scientific Organizations | 0303-2016-0006 (V.44.1.6) |
Abstract:
The effect of the support on the properties of copper catalysts supported on γ-Al2O3, SiO2, and TiO2–SiO2 with a ~5 wt % Cu content was studied in the one-pot synthesis of N-heptyl-p-toluidine from p-nitrotoluene and n-heptanal. The catalysts were characterized by elemental analysis, X-ray diffraction analysis, transmission electron microscopy, temperature-programmed reduction, and low-temperature nitrogen adsorption. The reaction was carried out in a flow reactor with the use of molecular hydrogen as a reducing agent. It was established that the nature of the support exerts a profound effect on the yield of the target secondary amine; in this case, 5%Cu/Al2O3 was found the most active catalyst. A combination of high catalyst activity in the hydrogenation of a nitro group to an amino group with the presence of acid sites, which facilitate imine formation as a result of the interaction of n-heptanal with p-toluidine, on the catalyst surface is necessary for reaching the greatest yield of N-heptyl-p-toluidine. The study of reaction mechanism on the 5%Cu/Al2O3 catalyst showed that p-nitrotoluene inhibits the hydrogenation of n-heptanal, and aldehyde hydrogenation into alcohol begins only after the conversion of the major portion of p-nitrotoluene as a result of the selective adsorption of the nitroarene under the conditions of the simultaneous presence of p-nitrotoluene and n-heptanal in the reaction mixture.
Cite:
Artyukha E.A.
, Nuzhdin A.L.
, Bukhtiyarova G.A.
, Derevyannikova E.A.
, Gerasimov E.Y.
, Gladkii A.Y.
, Bukhtiyarov V.I.
One-Pot Synthesis of Secondary Amines from Nitroarenes and Aldehydes on Supported Copper Catalysts in a Flow Reactor: The Effect of the Support
Kinetics and Catalysis. 2018. V.59. N5. P.593-600. DOI: 10.1134/s0023158418050014 WOS Scopus РИНЦ ANCAN OpenAlex
One-Pot Synthesis of Secondary Amines from Nitroarenes and Aldehydes on Supported Copper Catalysts in a Flow Reactor: The Effect of the Support
Kinetics and Catalysis. 2018. V.59. N5. P.593-600. DOI: 10.1134/s0023158418050014 WOS Scopus РИНЦ ANCAN OpenAlex
Original:
Артюха Е.А.
, Нуждин А.Л.
, Бухтиярова Г.А.
, Деревянникова Е.А.
, Герасимов Е.Ю.
, Гладкий А.Ю.
, Бухтияров В.И.
Одностадийный синтез вторичных аминов из нитроаренов и альдегидов на нанесенных медных катализаторах в проточном реакторе: влияние носителя
Кинетика и катализ. 2018. Т.59. №5. С.583-590. DOI: 10.1134/S0453881118050015 РИНЦ OpenAlex
Одностадийный синтез вторичных аминов из нитроаренов и альдегидов на нанесенных медных катализаторах в проточном реакторе: влияние носителя
Кинетика и катализ. 2018. Т.59. №5. С.583-590. DOI: 10.1134/S0453881118050015 РИНЦ OpenAlex
Dates:
| Submitted: | Mar 1, 2018 |
| Published print: | Sep 1, 2018 |
| Published online: | Sep 26, 2018 |
Identifiers:
| Web of science: | WOS:000445762600008 |
| Scopus: | 2-s2.0-85053897737 |
| Elibrary: | 35736802 |
| Chemical Abstracts: | 2018:1804581 |
| Chemical Abstracts (print): | 170:586507 |
| OpenAlex: | W2892624216 |