A Comparative Study of the Hydrogenation of 1,3,5-Trinitrobenzene and 2,4,6-Trinitrotoluene over a Copper–Alumina Catalyst in a Flow Reactor Full article
| Journal |
Kinetics and Catalysis
ISSN: 0023-1584 , E-ISSN: 1608-3210 |
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| Output data | Year: 2023, Volume: 64, Number: 1, Pages: 25-31 Pages count : 7 DOI: 10.1134/S0023158423010044 | ||||||
| Tags | hydrogenation; copper–alumina catalyst; 1,3,5-trinitrobenzene; 2,4,6-trinitrotoluene; triaminobenzenes; phloroglucinol derivatives; flow reactor | ||||||
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| Affiliations |
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Funding (1)
| 1 | Russian Science Foundation | 22-23-00127 |
Abstract:
The catalytic properties of a copper–alumina catalyst prepared from double layered hydroxide have been studied in the hydrogenation of 1,3,5-trinitrobenzene (TNB) and 2,4,6-trinitrotoluene (TNT) in a flow reactor. The reaction was carried out at a temperature of 120°C, a total pressure of 30 bar, and a substrate concentration of 0.10–0.15 M using methanol as a solvent. 1,3,5-Triaminobenzene (TAB) and 2,4,6-triaminotoluene (TAT) were isolated from the reaction mixture in the form of the double salts with sulfuric acid TAB⋅2H2SO4 and TAT⋅2H2SO4, the yields of which were 92 and 98%, respectively. At an initial trinitroarene concentration of 0.10 M, the hydrolysis of triaminobenzene salts made it possible to synthesize phloroglucinol and methylphloroglucinol in 78 and 91% yields, respectively. Increasing the concentration to 0.15 M reduced the yields to 71 and 88%, respectively. According to thermal analysis data, the observed differences in the yields of triaminobenzene salts and polyphenols were explained by the formation of different amounts of resinous by-products on the catalyst surface in the course of trinitroarene hydrogenation. In the hydrogenation of TNT, a smaller amount of resins was formed, and this led to higher yields of TAT⋅2H2SO4 and methylphloroglucinol. This was probably due to the presence of an electron-donating methyl substituent, which slowed down the polycondensation of TAT molecules.
Cite:
Nuzhdin A.L.
, Shchurova I.A.
, Bukhtiyarova M.V.
, Plyusnin P.E.
, Alekseyeva N.A.
, Sysolyatin S.V.
, Bukhtiyarova G.A.
A Comparative Study of the Hydrogenation of 1,3,5-Trinitrobenzene and 2,4,6-Trinitrotoluene over a Copper–Alumina Catalyst in a Flow Reactor
Kinetics and Catalysis. 2023. V.64. N1. P.25-31. DOI: 10.1134/S0023158423010044 WOS Scopus РИНЦ ANCAN OpenAlex
A Comparative Study of the Hydrogenation of 1,3,5-Trinitrobenzene and 2,4,6-Trinitrotoluene over a Copper–Alumina Catalyst in a Flow Reactor
Kinetics and Catalysis. 2023. V.64. N1. P.25-31. DOI: 10.1134/S0023158423010044 WOS Scopus РИНЦ ANCAN OpenAlex
Original:
Нуждин А.Л.
, Щурова И.А.
, Бухтиярова М.В.
, Плюснин П.Е.
, Алексеева Н.А.
, Сысолятин С.В.
, Бухтиярова Г.А.
Сравнительное исследование гидрирования 1,3,5-тринитробензола и 2,4,6-тринитротолуола на медно-алюминиевом оксидном катализаторе в проточном реакторе
Кинетика и катализ. 2023. Т.64. №1. С.31-38. DOI: 10.31857/S0453881123010045 РИНЦ OpenAlex
Сравнительное исследование гидрирования 1,3,5-тринитробензола и 2,4,6-тринитротолуола на медно-алюминиевом оксидном катализаторе в проточном реакторе
Кинетика и катализ. 2023. Т.64. №1. С.31-38. DOI: 10.31857/S0453881123010045 РИНЦ OpenAlex
Dates:
| Submitted: | Aug 8, 2022 |
| Accepted: | Sep 27, 2022 |
| Published print: | Feb 1, 2023 |
| Published online: | Jun 14, 2023 |
Identifiers:
| Web of science: | WOS:001010587400003 |
| Scopus: | 2-s2.0-85161961875 |
| Elibrary: | 54050056 |
| Chemical Abstracts: | 2023:1256577 |
| Chemical Abstracts (print): | 183:226145 |
| OpenAlex: | W4380550762 |