Aniline → Aniline

HRID 511892Notes

Reaction equation

HRID 511892 reaction equation
[CH3:1][N+:2]([CH3:5])([CH3:4])[CH3:3].[OH-:6].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O>[CH3:1][NH:2][C:5]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1.[CH3:1][N+:2]([CH3:5])([CH3:4])[CH3:3].[OH-:6].[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 2

HCID 6115AnilineHCID 60966Tetramethylammonium hydroxide3×

Product 3

HCID 6115AnilineHCID 7515N-MethylanilineHCID 60966Tetramethylammonium hydroxide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The present inventors have found that TMAH is relatively stable in the presence of aniline and water, particularly at a water to TMAH mole ratio of about 4:1 and that TMAH decomposition occurs when this ratio is reduced to 3.5:1 or less, with concomitant formation of a proportional amount of N-methyl aniline which results from the decomposition of TMAH in the presence of aniline, as shown in Table 4 below. The TMAH decomposition can be decreased by reducing the hold period. As shown in the working examples, the stability of TMAH in the presence of aniline was evaluated by stage-wise distillation of water from a mixture of aqueous TMAH (35% w/w) in aniline to obtain a water to TMAH molar ratio of about 4:1, then about 3.5:1 and then about 3:1, successively at 75° C. under 55 mm Hg pressure (similar to the process conditions mentioned in the first TMAH concentration step of Example 13 of the '111 patent as well as Example 1 of the '538 patent) and subsequently maintaining the reaction mass under atmospheric pressure for a hold period of 4 hours

Sources & evidence

ORD record
ord-72363357188e43b98309ce7c2374277a
Source dataset
uspto-grants-2015_08
Patent number
US09102585B2

Reaction notes

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