The reduction of nitro compounds by the use of platinum oxide-platinum black as a catalyst, and the conditions necessary for satisfactory yields by Adams and co-workers at the University of Illinois in 1927. They have made studies of the relative rates of reduction when two reducible groups are present. The reduction of compounds in which three potentially reducible groups are present, and the reduction of organic compounds containing both aliphatic and aromatic nitro groups have been studied in this work.

The work described in this paper is a continuation of that started in this laboratory last year by James W. Ferguson (1). While the use of platinum oxide is only recent (since 1922 (2)) hydrogenation of a large number of nitro compounds using platinum black catalyst has been studied. It has been pointed out in Ferguson0́9s thesis (1) that a study of the hydrogenation of a compound containing both an aliphatic and an aromatic nitro group would be particularly informative. It was found necessary to synthesize such a compound as none available were suitable for the purpose. In this paper the reductions of nitromethane and of the compound made by Ferguson are described.

Catalytic reductions of nitro compounds using platinum black and platinum oxide as catalysts have been studied for some time. Attempts have been made to determine the steps of the reduction of both aliphatic nitro and aromatic nitro groups in presence of other potentially reducible groups, such as ketone, aldehyde, and ethylene linkage. Studies have been made of the reduction of compounds containing two nitro groups on the benzene ring. In none of these studies, however, have any attempts been made to find data concerning the relative rates of reduction of a compound containing both an aromatic and an aliphatic nitro group until Ferguson in this laboratory synthesized such a compound (Îø-m-nitrophenyl- r-nitrobutyrophenone) in 1931. Both Ferguson and Dutton did some work on the complete reduction of this compound but very little on the partial reduction. The purpose of this piece of work was to study more fully the complete reduction and partial reduction of Îø-m-nitrophenyl-nitrobutyrophenone. With the completion of the study of this compound, a new compound containing the nitro group in a different position on the benzene ring and having a chlorine atom also on the ring should yield some interesting data when reduced.