10324-58-0Relevant articles and documents
Unprecedented Pyridine Ring C-C Bond Cleavages by Formic Acid.
Siskin, Michael,Katritzky, Alan R.,Balasubramanian, Marudai,Ferrughelli, David T.,Brons, Glen,Singhal, Gopal H.
, p. 4739 - 4742 (1993)
Formic acid at 350 deg C converts pyridine and 4-methylpyridine into products deriving from both αβ and βγ C-C bond cleavages of the pyridine ring.
Pyridine hydrodenitrogenation catalysed, under atmospheric pressure, by Ni and Mo oxynitrides and MoNi, MoPNi, AlNi and AlPNi mixed oxynitrides
Elkamel,Elidrissi,Yacoubi,Nadiri,Abouarnadasse
, p. 2157 - 2179 (2007/10/03)
Hydrodenitrogenation of pyridine has been realized, under atmospheric pressure, in the presence of oxymtride catalysts of molybdenum, nickel and their solid solutions as well as on mixed catalysts MoNi, MoPNi, AlNi and AlPNi. In all cases, the main reaction products are n-pentane and N- pentylpiperidine, at any conversion. Kinetic results suggest that the conversion of pyridine, on nickel oxynitride, proceeds through successive steps with hydrogenation as rate-limiting. Molybdenum oxynitride and Mo-Ni-N solid solutions tested in the temperature range 500°C-540°C, showed a good structural and catalytic stability, but a low catalytic activity. On the other hand, nickel oxynitride catalyst yielded hitcher activity at much lower temperatures (190°C- 250°C). X-rays analysis indicates that the used catalyst was entirely reduced to metallic nickel, which is the active phase. Under the same experimental conditions, mixed catalysts are relatively less active but more selective than nickel oxynitride into n-pentane formation.
Reaction of tetrahydrofurfuryl alcohol with ammonia and hydrogen on heterogeneous catalysts
Glebov,Kliger,Shuikin,Zaikin
, p. 346 - 352 (2007/10/03)
A study has been made of the vapour-phase reaction of tetrahydrofurfuryl alcohol with ammonia and hydrogen on Cu-, Ni-, Co- and Fe-containing bifunctional catalysts at a temperature of 180-240°C. It has been established that, irrespective of the type of catalyst, the main reaction products are piperidine, tetrahydrofurfurylamine and their derivatives. Copyright
Aqueous high-temperature chemistry of carbo- and heterocycles: Part 24 [1]. First demonstration of specific C-C bond scission of the pyridine ring. Reactions of piperidine, pyridine and some of their methyl derivatives in aqueous formic acid
Katritzky, Alan R.,Parris, Roslyn L.,Ignatchenko, Elena S.,Balasubramanian, Marudai,Barcock, Richard A.,Siskin, Michael
, p. 220 - 230 (2007/10/03)
In its reactions with the title compounds, formic acid variously acts as a formylating, methylating, and reducing agent. Both pyridine and piperidine are converted in significant amounts into 1-methyl-, 1-ethyl-, 1-propyl- and 1-pentyl-piperidines. Of the N-alkyl groups, isotopic labeling shows that only N-methyl derives from the formic acid, while the N-ethyl and N-propyl arise from heterocyclic ring C-C bond scission by retro-vinylogous-bis-aza-Aldol reactions. Detailed analysis of the products for pyridine, piperidine, and their 4-methyl derivatives, reacted separately and mixed, supports mechanisms in which a piperidine adds 1,2 to a pyridinium cation, or to a di- or tetra-hydropyridine, to initiate reaction sequences leading to the product slates found.
FORMATION OF SULFUR COMPOUNDS IN THE HYDRODENITROGENATION OF PIPERIDINE, PYRIDINE, 1-PENTYLAMINE AND 1-PENT-4-ENYLAMINE ON A NICKEL-TUNGSTEN CATALYST IN THE PRESENCE OF HYDROGEN SULFIDE
Cerny, Mirko
, p. 928 - 935 (2007/10/02)
Hydrogenations of piperidine, pyridine, 1-pentylamine, and 1-pent-4-enylamine were carried out in an autoclave at 300 deg C on a sulfidized nickel-tungsten catalyst using either pure hydrogen or a mixture of hydrogen with hydrogen sulfide.Hydrogen sulfide was found to raise the degree of conversion of the starting substances and accelerate the hydrodenitrogenation by formation of sulfur compounds; 1-pentanethiol, di(1-pentyl)sulfide, 2-methylthiacyclopentane, thiacyclohexane and other sulfur compounds were detected in the reaction mixtures in the presence of hydrogensulfide.A reaction pathway is suggested of the hydrodenitrogenation of piperidine in the presence of hydrogen sulfide, accounting for the favourable effect of the latter on the hydrodenitrogenation of nitrogen compounds.
HYDROGENOLYTIC CLEAVAGE OF PYRIDINE ON DIFFERENT COBALT-MOLYBDENUM AND NICKEL-TUNGSTEN CATALYSTS
Cerny, Mirko,Kraus, Milos
, p. 1348 - 1354 (2007/10/02)
Composition of the reaction products formed by hydrogenation of pyridine at 300 deg C and 15 MPa in the presence of 15 sulphided and unsulphided molybdenum and tungsten catalysts promoted by cobalt and by nickel, respectively, using alumina as the support in most cases, has been examined.It has been proved that the catalyst composition affects both its hydrogenation activity and the ratio of transalkylation to cracking (or hydrocracking) reactions.Relations between the catalysts composition and its activity and selectivity found for the reaction of pyridine differ from those reported for hydrogenolytic cleavage of thiophene, hydrogenation and isomerisation of cyclohexene.
Hydrogenolysis of nitrogen-containing compounds on cobalt-molybdenium catalyst
Cerny, Mirko
, p. 2215 - 2218 (2007/10/02)
Hydrogenolysis of N-(1-hexyl)piperidine, N-(1-pentyl)piperidine and 1-pentyl-1-hexylamine on sulphidized CoO-MoO3 catalysts has been investigated.The primary reaction in the hydrogenolysis is the cleavage of the bond between the nitrogen atom and the methylene group of the alkyl substituent or of the methylene ring.Alkylation and transalkylation reactions on the nitrogen play also a role.
