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102-82-9Relevant articles and documents
Effect of the catalyst preparation method on the performance of Ni-supported catalysts for the synthesis of saturated amines from nitrile hydrogenation
Segobia,Trasarti,Apesteguía
, p. 1693 - 1703 (2019)
The liquid-phase hydrogenation of butyronitrile to saturated amines was studied on silica-supported Ni catalysts prepared by either incipient-wetness impregnation (Ni/SiO2-I) or ammonia (Ni/SiO2-A) methods. A Ni/SiO2-Al2O3-I sample was also used. Ni/SiO2-I was a non-acidic catalyst containing large Ni0 particles of low interaction with the support, while Ni/SiO2-A was an acidic catalyst due to the presence of Ni2+ species in Ni phyllosilicates of low reducibility. Ni/SiO2-I formed essentially butylamine (80%), and dibutylamine as the only byproduct. In contrast, Ni/SiO2-A yielded a mixture of dibutylamine (49%) and tributylamine (45%), being the formation of butylamine almost completely suppressed. The selective formation of secondary and tertiary amines on Ni/SiO2-A was explained by considering that butylamine is not release to the liquid phase during the reaction because it is strongly adsorbed on surface acid sites contiguous to Ni0 atoms, thereby favoring the butylimine/butylamine condensation to higher amines between adsorbed species.
Deoxygenation of amine N-oxides using gold nanoparticles supported on carbon nanotubes
Donck, Simon,Gravel, Edmond,Shah, Nimesh,Jawale, Dhanaji V.,Doris, Eric,Namboothiri, Irishi N. N.
, p. 50865 - 50868 (2015)
Deoxygenation of a variety of aromatic and aliphatic amine N-oxides has been carried out in excellent yield using dimethylphenylsilane as the reducing agent under the catalytic influence of a carbon nanotube-gold nanohybrid at room temperature. Low catalyst loading, good TON and TOF values, and recyclability of the catalyst are some of the salient features of our methodology.
RUTHENIUM CATALYZED N-ALKYLATION OF AMIDES WITH ALCOHOLS.
Watanabe,Ohta,Tsuji
, p. 2647 - 2651 (1983)
Amides reacted with primary alcohols in the presence of a catalytic amount of RuCl//2(PPh//3)//3 at 180 degree C to give the corresponding N-monoalkyl amides in fairly good yields. Thus, benzamide reacted with l-octanol to give N-octylbenzamide in 76% yield with excellent product selectivity. Little esterification of amides with alcohols occurred and selectivity to the N-alkylation was high. Most of the amides gave N-monoalkyl amides but no N,N-dialkyl amides. But formamide reacted with l-butanol to give N,N-dibutylformamide, as well as N-butylformamide, in low yield. RuCl//2(PPh//3)//3 was the most effective catalyst for this reaction and RuHCl(PPh//3)//3 also had some catalytic activity.
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Ashby
, p. 4791,4794 (1959)
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Hofmann Decomposition of Queternary Ammonium Salts under Phase-transfer Catalytic Conditions
Zerda, Jaime de la,Neumann, Ronny,Sasson, Yoel
, p. 823 - 826 (1986)
The known Hofmann degradation of quaternary ammonium salts under basic phase-transfer catalytic conditions has been studied.The base-catalysed isomerization of p-allylanisole to p-methoxy-β-methylstyrene was used as a kinetic probe to find experimentally the rate constant and activation energy of the Hofmann decomposition without isolating the quaternary ammonium basic salt R4N+B- (B- = base anion).Reactions performed at various temperatures showed that the higher the temperature the greater was the initial rate but the lower the final conversion in the isomerization reaction.The quaternary ammonium hydroxide was found to catalyse the isomerization and the Hofmann degradation more effectively than the corresponding alkoxide.This indicates that the former is a stronger base in the non-polar aprotic solvents common in phase-transfer catalysis.
Synthesis of n-butylamine from butyronitrile on Ni/SiO2: Effect of solvent
Segobia, Darío J.,Trasarti, Andrés F.,Apesteguía, Carlos R.
, p. 2272 - 2279 (2014)
The effect of solvent on Ni(10.5percent)/SiO2 activity and selectivity for the liquid-phase hydrogenation of butyronitrile to butylamines was studied at 373 K and 13 bar using ethanol, benzene, toluene and cyclohexane as solvents. In ethanol, a protic solvent, the Ni catalyst yielded n-butylamine (84percent) and dibutylamine (16percent). When non-polar solvents, such as cyclohexane, toluene or benzene, were used, the solvent-catalyst interaction strength determined the selectivity to n-butylamine: the stronger the solvent-catalyst interaction the higher the n-buylamine production. The yield to n-butylamine in non-polar solvents varied between 39percent (cyclohexane) and 63percent (benzene).
ELECTROCHEMICAL REDUCTION OF TRIPHENYL PHOSPHATE
Yanilkin, V. V.,Budnikova, Yu. G.,Kargin, Yu. M.,Gritsenko, E. I.,Strelets, V. V.
, p. 1149 - 1152 (1990)
The electrolytic reduction of triphenyl phosphate proceeds with the participation of tetrabutylammonium cations with the formation of butyl diphenyl phosphate in DMF.It was concluded that the step involving electron transfer to the triphenyl phosphate molecule has retarded character.
Epoxide as precatalyst for metal-free catalytic transesterification
Tanaka, Shinji,Nakashima, Takuya,Satou,Oono, Hiromi,Kon, Yoshihiro,Tamura, Masanori,Sato, Kazuhiko
, p. 2009 - 2013 (2019)
Transesterification of methyl esters was accelerated by an in situ-generated metal-free catalyst comprising a quaternary alkylammonium salt and an epoxide. The combination of a quaternary alkylammonium acetate and glycidol is optimal, and various esters were synthesized from methyl esters with alcohols in good to excellent yield. Analysis of the catalyst solution revealed that basic species are generated by the ring-opening reaction of epoxide.
AMINATION OF BUTANOL ON Na FORMS OF ZEOLITES
Minachev, Kh. M.,Maksimov, A. I.,Mishin, I. V.,Levitskii, I. I.
, p. 2484 - 2488 (1985)
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Polyethylene glycol-enhanced chemoselective synthesis of organic carbamates from amines, CO2, and alkyl halides
Kong, De-Lin,He, Liang-Nian,Wang, Jin-Quan
, p. 3298 - 3307 (2011)
An efficient and environmentally benign method for the synthesis of organic carbamates was developed. Amines, CO2, and alkyl halides underwent a three-component reaction with the aid of K2CO3 and polyethylene glycol (PEG, MW=400), affording the organic carbamates under ambient conditions. PEG could presumably act as a solvent and phase-transfer catalyst (PTC). Notably, the presence of PEG could also depress the alkylation of both the amine and the carbamate, thus resulting in enhanced selectivity toward the target carbamate. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
The synthesis of N-ethyl-n-butylamine by amines disproportionation
Xu, Lu-Feng,Huang, Jia-Min,Qian, Chao,Chen, Xin-Zhi,Feng, Lie,Chen, Yun-Bin,He, Chao-Hong
, p. 2697 - 2704 (2013)
A synthesis of N-ethyl-n-butylamine with simple separation method in a fixed-bed reactor using CuO-NiO-PtO/γ-Al2O3 as the catalyst was proposed and investigated. The present catalytic system gave high activity and good selectivity, and the reaction conditions such as temperature and liquid hourly space velocity were optimized. Since no water was generated, the protocol proved to be easy to separate, and N-ethyl-n-butylamine was collected at 110 °C by distillation. The yield and the purity were 60.7 and 99.5 %, respectively.
Investigation of the stability of quaternary ammonium methyl carbonates
Weisshaar, Duane E.,Earl, Gary W.,Amolins, Michael W.,Mickalowski, Kyle L.,Norberg, Justin G.,Rekken, Brian D.,Burgess, Angela M.,Kaemingk, Bethany D.,Behrens, Katherine C.
, p. 199 - 205 (2012)
Quaternary ammonium compounds are used commercially for a variety of applications and some are of interest as ionic liquids. For many years dimethyl carbonate has been touted as a green reagent, including its use for methylation (quaternization) of tertiary amines. In addition, substitution of the methyl carbonate by other anions can be efficiently and cleanly accomplished by reaction with the corresponding acid. How stable are these methyl carbonate quaternary compounds? High field 13C NMR shows that in the presence of water, the methyl carbonate is converted to bicarbonate. Headspace GCMS indicates that the alkylammonium methyl carbonate salts are stable below 170-180 °C while the bicarbonate salts are stable to only about 140 °C. Thermal decomposition occurs by decarboxylation and by dealkylation. AOCS 2011.
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Snyder,Speck
, p. 2895 (1939)
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A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics
García-Domínguez, Andrés,Gonzalez, Jorge A.,Leach, Andrew G.,Lloyd-Jones, Guy C.,Nichol, Gary S.,Taylor, Nicholas P.
supporting information, (2022/01/04)
The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.
Synthesis process of tetrabutylammonium bromide
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Paragraph 0048-0053; 0058-0059, (2020/12/06)
The invention discloses a synthesis process of tetrabutylammonium bromide. The process is characterized by comprising the following steps: (1) taking dibutylamine and n-butyraldehyde as initial raw materials, taking water as a hydrogen source and butanol as a sacrificial reagent under the action of a modified titanium dioxide photocatalyst, and preparing tributylamine by a photocatalytic continuous micro-channel reactor through a reductive amination mechanism; and (2) after concentrating the obtained tributylamine, making the tributylamine directly dissolved in the solvent and mixed with a certain proportion of n-bromobutane, and then enter the next step continuous micro-channel reactor, such that the target product TBAB can be obtained at the high yield after the reaction is performed for3-5 h at the temperature of 60-90 DEG C. Compared with the kettle type reaction, the continuous reaction temperature is low, the reaction time is short, and the process is safe and efficient.