9.1 g of azine was stirred with 50 ml of benzene and 25 ml of saturated aqueous ammonia at 70 °C, where benzene was used to avoid crystallization of azine (mp 164 °C) and also to produce a difference in density between the organic and aqueous layers as the densities of benzophenone and azine are close to unity. Zinc and copper were extracted immediately and almost quantitatively. However, the extraction from actual reaction mixtures with similar composition was slow especially for copper. After six extractions with fresh aqueous ammonia (30 min per batch), about 14% Cu was found in the organic layer.Similar behavior was also observed in the extraction with aqueous ammonium chloride. Another troublesome problem in the use of aqueous ammonium chloride is the regeneration of recovered catalyst, which precipitates from the salt solution as a complex mass including ammonium chloride. For example, a precipitate, CuCU^N^Cl^^O or a mixture with CuC12-2H20, was obtained from cupric chloride and aqueous ammonium chloride. In the case of cuprous chloride with oxygen, much more complex behavior was observed. It is, therefore, undesirable to use aqueous ammonium chloride for recycling of the catalyst.Benzophenone azine is slightly soluble in ethanol and soluble in benzene; benzophenone is soluble and the catalysts are slightly soluble, in both solvents. Thus azine was isolated from the reaction mixture and the catalysts could be recycled as shown in the following example. (Zinc chloride is soluble in ethanol but precipitates from ethanol in the presence of ammonia or imine. Cuprous chloride is insoluble both in ethanol and benzene, but some slightly soluble complexes are formed in the presence of imine.)A mixture of ammonia and oxygen (NH3/O9 = 4:1) was passed through a mixture containing 18.2 g of benzophenone, 0.3 g of zinc chloride, and 0.5 g of cuprous chloride at 200 °C under 5 atm pressure at a rate of 10 l./h for 2 h. This condition results in a 49% one-pass yield of azine. The reaction mixture was diluted with 200 ml of ethanol to precipitate azine and catalyst. The precipitated catalyst was separated from the azine by washing with 150 ml of benzene to dissolve the azine. Unreacted benzophenone, intermediate imine, and a part of the catalyst remained in ethanol solution. The ethanol was evaporated off under vacuum, further benzophenone was added to make up for loss, and the recovered catalyst powder was returned. The procedure was repeated four times, and 36.5 g of azine was obtained from a total charge of 45.7 g of benzophenone. The overall yield of azine was 81%.