F:Highly flammable;
109-74-0Relevant academic research and scientific papers
Microwave-assisted efficient one-pot synthesis of nitriles from aldehydes in the presence of P2O5/SiO2 in solvent-free media
Eshghi, Hossein,Gordi, Zinat
, p. 619 - 623 (2005)
A rapid and efficient procedure is developed for a one-pot synthesis of nitrites by condensation of aldehydes with hydroxylamine hydrochloride in the presence of P2O5/SiO2 in solvent-free media under microwave irradiation. Copyright Taylor & Francis Inc.
Studies of the chemical selectivity of hapten, reactivity, and skin sensitization potency. 1. Synthesis and studies on the reactivity toward model nucleophiles of the 13c-labeled skin sensitizers hex-1-ene- and hexane-1,3-sultones
Meschkat, Emmanuel,Barratt, Martin D.,Lepoittevin, Jean-Pierre
, p. 110 - 117 (2001)
The potent skin sensitizers hex-1-ene- and hexane-1,3-sultone have been synthesized isotopically labeled with 13C at reactive sites. The reactivity of 2-[13C]- and 3-[13C]hex-1-ene-1,3-sultones and of 3-[13C]hexane-1,3-sultone toward a series of model nucleophiles for protein amino acid residues, i.e., butylamine, diethylamine, imidazole, propanethiol, and phenol, was followed by 13C NMR spectroscopy. The reactivity in water of hex-1-ene-1,3-sultone toward model nucleophiles follows the hard and soft acid and base theory with the hard nucleophiles (primary and secondary amine and phenate) mainly reacting at position 3 by SN substitution, and the soft nucleophiles (thiolate and imidazole) mainly reacting at position 2 by a Michael addition reaction. Hexane-1,3-sultone reacts with model nucleophiles at position 3 by SN substitution. Both saturated and unsaturated sultones are sensitive to hydrolysis when reacted in water.
Reaction of interstitial cyanide ions in a hydrotalcite-like material with organic chlorides
Suzuki, Eiichi,Inoue, Atsushi,Ono, Yoshio
, p. 1291 - 1292 (1998)
A hydrotalcite-like material, Mg6Al2(OH)16Cl2-xCN x·4H2O (x= 1.53-1.94), was prepared and tested as a reagent for the nucleophilic substitution for chlorine atom of C6H5CH2Cl, C4H9Cl, and C3H7Cl by the CN ions in the interlayer of the material. The corresponding organic cyanides were obtained at 353 K in a non-polar solvent, toluene.
A Beckmann-Type Dehydration of n-Butyraldoxime Catalyzed by Cytochrome P-450
DeMaster, Eugene G.,Shirota, Frances N.,Nagasawa, Herbert T.
, p. 5074 - 5075 (1992)
n-Butyraldoxime undergoes a unique NADPH-dependent, Beckmann-type dehydration catalyzed by rat liver microsomes to give n-butyronitrile.
Rhodium-Catalysed Asymmetric Hydroformylation of Unsaturated Nitriles
Lambers-Verstappen, Marielle M.H.,De Vries, Johannes G.
, p. 478 - 482 (2003)
Asymmetric hydroformylation of crotononitrile (1) and ally cyanide (2) was probed with the view to develop a synthesis for (R)-4-amino-2-methyl-butan-1-ol. Hydroformylation of 1 under a variety of conditions mainly led to hydrogenated product. Hydroformylation of 2 with Rh/tris(2,4-di-tert-butylphenyl) phosphite gave good selectivity to the formylated nitrile with an n/iso of 77:23. Asymmetric hydroformylation of 2 could be accomplished in 66% ee using Rh/(R,S)-BINAPHOS.
The Question of Tautomerism of Alkylnitrile and Isonitrile Cations
Chess, Edward K.,Lapp, R. L.,Gross, Michael L.
, p. 475 - 480 (1982)
The isomeric pairs+. and +. and +. and +. have been established as stable, noninterconverting structures.The conclusion derives from studies of collision induced decomposition spectra.The same conclusion pertains for the ions +. and +., and for +., +. and HNCCHCHCNH>+..The energy barrier of a -hydrogen shift, a possible isomerization mechanism, is determined to be at least 163kJ mol-1 for the +. and +. pair, and the barrier may be as high as 318kJ*mol-1.The C3H5N and C4H4N2 radical cations decompose before they can be activated with 318 kJ mol-1 of internal energy.
Purification and characterization of aldoxime dehydratase of the head blight fungus, Fusarium graminearum
Kato, Yasuo,Asano, Yasuhisa
, p. 2254 - 2257 (2005)
Fungal aldoxime dehydratase (Oxd) of Fusarium graminearum MAFF305135 was purified and characterized for the first time from its overexpressing Escherichia coli transformant. The enzyme showed about 20% identity with known Oxds, and had similar enzymatic properties with nitrilase-linked Oxd from the Bacillus strain. It belongs to a group of phenylacetaldoxime dehydratases (EC 4.99.1.7), based on its substrate specificity and kinetic analysis.
Study on alumina-supported cobalt-nickel oxide catalyst for synthesis of acetonitrile from ethanol
Feng, Cheng,Zhang, Yuecheng,Zhang, Yining,Wen, Yanlong,Zhao, Jiquan
, p. 168 - 177 (2011)
A new alumina-supported cobalt-nickel oxide catalyst for the synthesis of acetonitrile from ethanol and ammonia was prepared by coprecipitation-kneading method. The parameters influencing the reaction were studied thoroughly and an optimized process, which is running the reaction at 380 °C under atmospheric pressure while keeping the ammonia/alcohol molar ratio of 5 and GHSV of 1,163 h-1, was obtained. Under the optimized conditions the catalyst reached its best performance when being on stream for 40 h, at which the yield of acetonitrile was 92.6%. Then the selectivity to acetonitrile decreased gradually but the yield of acetonitrile always remained higher than 81% within 720 h. The samples of the fresh and used catalyst were characterized by XRD, XPS, TEM, EDX and N2 adsorption-desorption analysis. The results revealed that carbon deposition and formation of metal carbides from the active species in the catalytic runs led to the deterioration of the catalyst. Graphical Abstract: A new Co-Ni/γ-Al2O3 catalyst for the amination of ethanol to acetonitrile was studied in a continuous fixed-bed reactor and the reaction parameters were optimized. The mechanisms for the formation of acetonitrile and butyronitrile were discussed. The reasons leading to the deterioration of the catalyst were investigated through the characterization of the fresh, used and regenerated samples of the catalyst by means of XRD, XPS, TEM and N2 adsorption-desorption techniques.
Thermal Desorption and Infrared Studies of Primary Aliphatic Amines adsorbed on Haematite (α-Fe2O3)
Marx, Ute,Sokoll, Rolf,Hobert, Hartmut
, p. 2505 - 2514 (1986)
The adsorption of n-octadecylamine on α-Fe2O3 at the solid/liquid interface, and of n-butylamine at the solid/liquid and solid/vapour interfaces has been studied by infrared spectroscopy.To obtain further information about the nature of desorbing products, temperature-programmed desorption experiments were made with n-butylamine-α-Fe2O3 adsorbates.No difference could be detected by i.r. spectroscopy between the nature of adsorbates formed under the various mentioned conditions.Adsorption of n-octadecylamine and n-butylamine on α-Fe2O3 mainly involves coordinative interactions between amine and Lewis-acidic surface sites (Fe(3+) cations).Furthermore, hydrogen bonds are formed between surface hydroxy groups and adsorbed amine molecules. n-Butylamine adsorbed on α-Fe2O3 gave four different desorption peaks (I-IV) which are formed by n-butylamine (I:423 K), butyronitrile (II:530 K), CO2 (III:630K) and H2O (IV:713 K).Desorption of CO2 and H2O is caused by the oxidation of amine molecules strongly adsorbed on two different types of coordination sites.
Ambient Hydrogenation and Deuteration of Alkenes Using a Nanostructured Ni-Core–Shell Catalyst
Beller, Matthias,Feng, Lu,Gao, Jie,Jackstell, Ralf,Jagadeesh, Rajenahally V.,Liu, Yuefeng,Ma, Rui
supporting information, p. 18591 - 18598 (2021/06/28)
A general protocol for the selective hydrogenation and deuteration of a variety of alkenes is presented. Key to success for these reactions is the use of a specific nickel-graphitic shell-based core–shell-structured catalyst, which is conveniently prepared by impregnation and subsequent calcination of nickel nitrate on carbon at 450 °C under argon. Applying this nanostructured catalyst, both terminal and internal alkenes, which are of industrial and commercial importance, were selectively hydrogenated and deuterated at ambient conditions (room temperature, using 1 bar hydrogen or 1 bar deuterium), giving access to the corresponding alkanes and deuterium-labeled alkanes in good to excellent yields. The synthetic utility and practicability of this Ni-based hydrogenation protocol is demonstrated by gram-scale reactions as well as efficient catalyst recycling experiments.
