Ring alkylation of aniline or an aniline derivative using ionic liquid catalysts
A technology of aniline derivatives and ionic liquids, applied in the preparation of amino compounds from amines, organic chemistry, etc., can solve problems that do not involve cycloalkylation of aniline or aniline derivatives
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Examples
Embodiment 1
[0027] Alkylation of Aniline Using 1-Decene, Aluminum Chloride and 3-Butyl-1-methylimidazolium Chloride
[0028]To a 1 L 4-neck round bottom flask equipped with a heating mantle, temperature controller, water-cooled reflux condenser with positive nitrogen pressure inlet at the top, mechanical stirrer, and thermocouple was added aniline (46.52 g, 0.50 mol ), 1-decene (245.54 g, 1.75 moles, 3.5 equivalents relative to aniline), aluminum chloride (33.38 g, 0.25 moles, 50 mole % relative to aniline) and finally 3-butyl chloride -1-Methylimidazolium (BMIM chloride, 10.89 g, 0.0625 mol, 12.5 mol% relative to aniline). Stir at about 200-300 rpm and heat the mixture first to 100°C, then to 160°C and finally to 180°C. 1-Decene undergoes gentle reflux at this temperature. Heating was continued at 167-180°C for a total of 23.4 hours.
[0029] The reaction mixture was allowed to cool to room temperature and diluted with 400 mL of n-heptane. The reaction product separated into two phas...
Embodiment 2
[0031] Alkylation of Aniline Using Nonene, Aluminum Chloride, and Methyltributylammonium Chloride
[0032] To an apparatus similar to that described in Example 1, aniline, nonene, and aluminum chloride were sequentially added under a nitrogen atmosphere. Stirring at 200-300 rpm was started and then solid methyltributylammonium chloride was added. Then start heating to 160°C. Reflux started at a pot temperature of 137.5°C and steadily increased as the aniline was alkylated. Heating between 137-160°C was continued for 28.2 hours, then the reaction mixture was allowed to cool to room temperature.
[0033] The reaction mixture was diluted with 300 mL of n-heptane and 200 mL of dichloromethane, and the two phases were separated. When the heptane phase was washed with 500 mL of water, no reaction occurred. Careful addition of 500 mL of water to the lower dichloromethane phase resulted in a vigorous reaction, indicating that this phase contained the catalyst. After the reaction ...
Embodiment 3
[0036] Alkylation of Aniline Using Dodecene, Aluminum Chloride and Methyltributylammonium Chloride
[0037] Into an apparatus similar to that described in Example 1 was added aniline, dodecene, followed by aluminum chloride under positive nitrogen pressure, and slow stirring was started. After stirring with an exotherm of up to 46°C, methyltributylammonium chloride was added. The reaction mixture was heated to 160°C and maintained at this temperature for 27.8 hours. The reaction mixture was then allowed to cool to room temperature and diluted with 300 mL of n-heptane - 200 mL of dichloromethane.
[0038] The reaction mixture separated into a bulky upper phase and a dark red-orange lower phase. The upper layer was washed with 2×500 mL water, 500 mL ammonia water (400 mL water / 100 mL concentrated ammonia water), and then dried over anhydrous sodium sulfate.
[0039] The sodium sulfate was removed by suction filtration and the filtrate was evaporated in vacuo on a rotary evapo...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More