Synthesis of N,N-Dimethylaniline from Aniline and Methanol

Bhattacharyya, Asish K.; Nandi, Dilip K.

doi:10.1021/i360059a013

Cited by 7 publications

(3 citation statements)

References 5 publications

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“…In particular, methanol has been widely used because of its ready availability and ease of handling. Conventional liquid acids such as sulfuric, hydrochloric, hydrobromic, and hydroiodic acids have been reported to catalyze the methylation of amines [102]. On the other hand, solid acids such as alumina [103][104][105][106], silica-alumina [107], faujasite [108], beta zeolite, EMT zeolites [109], AlPO 4 -5 [110,111], and niobic acid [112] have been used as catalysts in the gas-phase flow system, which requires no solvent, circumvents tedious separation procedures, and recycles the catalyst.…”

Section: Methylation Of Toluene (Equationmentioning

confidence: 99%

Catalytic Reactions over Halide Cluster Complexes of Group 5–7 Metals

Nagashima

Kamiguchi

Chihara

2014

Metals

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Halide clusters of Group 5-7 metals develop catalytic activity above 150-250 °C, and the activity is retained up to 350-450 °C by taking advantage of their thermal stability, low vapor pressure, and high melting point. Two types of active site function: the solid Brønsted acid site and a coordinatively unsaturated site that catalyzes like the platinum metals do. Various types of catalytic reactions including new reactions and concerted catalyses have been observed over the clusters: hydrogenation, dehydrogenation, hydrogenolysis, isomerization of alkene and alkyne, and alkylation of toluene, amine, phenol, and thiol. Ring-closure reactions to afford quinoline, benzofuran, indene, and heterocyclic common rings are also catalyzed. Beckmann rearrangement, S-acylation of thiol, and dehydrohalogenation are also catalyzed. Although the majority of the reactions proceed over conventional catalysts, closer inspection shows some conspicuous features, particularly in terms of selectivity. Halide cluster catalysts are characterized by some aspects: cluster counter anion is too large to abstract counter cation from the protonated reactants, cluster catalyst is not poisoned by halogen and sulfur atoms. Among others, cluster catalysts are stable at high temperatures up to 350-450 °C. At high temperatures, apparent activation energy decreases, and hence weak acid can be a catalyst without decomposing reactants. OPEN ACCESSMetals 2014, 4 236

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Section: Methylation Of Toluene (Equationmentioning

confidence: 99%

Catalytic Reactions over Halide Cluster Complexes of Group 5–7 Metals

Nagashima

Kamiguchi

Chihara

2014

Metals

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“…PhCH,NMe,+ MeOHF---PhCH,OMe+NHMe, (9) Firstly, if reactions (7) and (8) happen to be parallel, (8) may predominate in the presence of a large amount of methanol, resulting in the formation of mostly BME. Secondly, if BME happens to be a thermodynamically more stable product than DMBA, then even if DMBA is a kinetically controlled product and is formed in large amounts initially, it may subsequently be converted to BME by reaction (9) in the presence of a large excess of methanol.…”

Section: Effect Of Mol Ratio Of Benzylamine To Methanolmentioning

confidence: 99%

Acid catalyzed pressure synthesis of N,N‐dimethylbenzylamine from benzylamine and methanol

Nandi

Palit

Deka

1987

J of Chemical Tech & Biotech

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The synthesis of N,N‐dimethylbenzylamine from benzylamine and methanol in the presence of hydrochloric acid catalyst has been carried out under pressure. Nitrogen pressure is helpful only to a limited extent, beyond which it is neither helpful nor detrimental. Under optimum conditions (517 K, 6.0295 MPa, residence period 2 h, benzylamine‐to‐methanol‐to‐hydrochloric acid mol ratio 1:2:1) the conversion of benzylamine to N,N‐dimethylbenzylamine is 57.09%.

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“…Moreover, these methods require not only harmful reagents but also a stoichiometic amount of a strong base to neutralize acid by-products. The N-methylation of aniline with methanol in the presence of a strong acid catalyst [5] or a heterogenous catalyst in gas-phase at high temperature has been extensively studied [6][7][8][9][10][11]. In most of these reactions, the conversions of aniline were low and the methylation of aniline gave toluidine, N-methylaniline (NMA), and N,N-dimethylaniline as major products.…”

Section: Introductionmentioning

confidence: 99%