Pentachloroaniline

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 131 parts of a mixture of tetrachloroaniline and pentachloroaniline, corresponding to the composition given in Example 3, 200 parts of phenol and 9 parts of sodium iodide are reacted in the presence of 22 parts of a ruthenium-on-charcoal catalyst (5% strength) which is moist with water and has already been used for 6 similar reaction cycles, corresponding to 15 parts of dry catalyst, with hydrogen at 165° C. under a pressure of 40 to a maximum of 50 bars, during the course of 8 hours. After the usual working up, 91.5 parts of 3,5-dichloroaniline are obtained, with complete conversion of the starting material. Yield: 98% of theory.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 131 parts of a mixture of tetrachloroaniline and pentachloroaniline, corresponding to the composition given in Example 3, 200 parts of phenol and 9 parts of sodium iodide are reacted in the presence of 22 parts of a ruthenium-on-charcoal catalyst (5% strength) which is moist with water and has already been used for 6 similar reaction cycles, corresponding to 15 parts of dry catalyst, with hydrogen at 165° C. under a pressure of 40 to a maximum of 50 bars, during the course of 8 hours. After the usual working up, 91.5 parts of 3,5-dichloroaniline are obtained, with complete conversion of the starting material. Yield: 98% of theory.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 131 parts of a mixture of 2,3,4,5- and 2,3,5,6-tetrachloroaniline and pentachloroaniline in the ratio of 38:60:2 percent by weight and 200 parts of phenol are reacted with hydrogen over 20 parts of a 1% strength palladium/charcoal catalyst and a maximum pressure of 50 bar and at 170° C. in a tantalum autoclave, in the course of 10 hours, while stirring. After the autoclave has been cooled and the pressure released, the reaction mixture is diluted with 500 parts of water and separated off from the catalyst, and after the addition of toluene, the mixture is rendered alkaline with sodium hydroxide solution. The solution of 3,5-dichloroaniline in toluene, obtained by separation of the layers, is distilled. Yield: 90 g (=98%) of a 99% strength 3,5-dichloroaniline. The phenol can be recovered from the aqueous phase by acidifying the latter and extracting it by shaking with toluene. It was possible to re-use the catalyst 20 times without it losing any of its activity. After the autoclave has been cooled separated off from the catalyst after the addition of toluene