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ChemicalBook CAS DataBase List Aniline
62-53-3

Aniline synthesis

14synthesis methods
Aniline was obtained in 1826 by Unverdorben from distillation of indigo and was given the name aniline in 1841 by Fritzsche (Windholz et al 1983). The chemical was manufactured in the U. S. by the Bechamp reaction involving reduction of nitrobenzene in the presence of either copper/silica or hydrochloric acid/ferrous chloride catalysts; but in 1966, amination of chlorobenzene with ammonia was introduced (IARC 1982; Northcott 1978). Currently, aniline is produced in the U.S., several European countries and Japan by the catalytic hydrogenation of nitrobenzene in either the vapor phase or solvent system. This chemical is also produced by reacting phenol with ammonia (HSDB 1989). Production in 1982 amounted to 331,000 tons (HSDB 1989).
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Yield:62-53-3 95%

Reaction Conditions:

with 5%-palladium/activated carbon;hydrogen;sodium hydroxide in methanol at 20; under 750.075 Torr; for 2 h;Autoclave;Green chemistry;

Steps:

11 Example 11

In an autoclave, 220 g (1 mol) of N-Cbz-aniline was added to 1300 mL of methanol.Then add 1000 mL of saturated sodium hydroxide solution, and then add 22 g of palladium carbon in a content of 5%, and replace the gas in the reaction flask three times with nitrogen.Then replace it twice with hydrogen, pass hydrogen gas to make the pressure in the autoclave reach 0.1 MPa, and react at room temperature for 2 h. TLC monitors the reaction of the starting material completely and filters the reaction solution.Further, 50 g of activated carbon was added to the filtrate, stirred for 20 minutes, filtered, and the filtrate was concentrated to obtain 90 g of aniline in a yield of 95%.

References:

CN108440409,2018,A Location in patent:Paragraph 0041; 0042

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