Design of Selective 1-Ethyl-2-nitromethylenepyrrolidine Hydrogenation for Pharmaceuticals Production
Science article
| Общее |
Language:
Английский,
Genre:
Full article,
Status:
Published,
Source type:
Original
|
| Conference |
4th International Symposium on Heterogeneous Catalysis and Fine Chemicals
08-12 Sep 1996
,
Basel
|
| Source |
Heterogeneous Catalysis and Fine Chemicals IV : Proceedings of the 4th International Symposium on Heterogeneous Catalysis and Fine Chemicals, 8-12 September 1996, Basel, Switzerland
Compilation,
1997.
675 c. ISBN 9780444823908.
|
| Journal |
Studies in Surface Science and Catalysis
ISSN: 0167-2991
|
| Output data |
Year: 1997,
Volume: 108,
Pages: 255-262
Pages count
: 8
DOI:
10.1016/S0167-2991(97)80912-3
|
| Authors |
Semikolenov V.A.
1
,
Simakova I.L.
1
,
Golovin A.V.
1
,
Burova O.A.
1
,
Smirnova N.M.
1
|
| Affiliations |
| 1 |
Boreskov Institute of Catalysis, Prospekt Akademika Lavrentieva 5,
Novosibirsk, 630090, Russia
|
|
The peculiarities of 1-ethyl-2-nitromethylenepyrrolidine (ENMP) hydrogenation over Pd/C catalyst were studied. Two routes of ENMP conversion resulting in 1-ethyl-2-aminomethylpyrrolidine (EAMP) and side products formation were found out. It was shown that the side reaction is the ENMP hydrolysis. This reaction proceeds via the acid-base mechanism and is accelerated by EAMP, producing the basic medium. The new method of EAMP preparation by ENMP hydrogenation in presence of CO2 was proposed. The kinetic peculiarities of this process were studied and parameters determining the EAMP selectivity were clarified. The role of CO2 in selective ENMP hydrogenation was studied using IR, 1H and 13C NMR methods. It was found that the reversible interaction of EAMP with CO2 produces the intermolecular salt of EAMP carbamic acid and thus prevents ENMP hydrolysis by maintaining the neutral pH of the reaction medium. The catalytic setup for the ENMP hydrogenation and the new method of EAMP separation and purification, which provides the high-purity EAMP for medicines synthesis, have been developed.