https://doi.org/10.15255/KUI.2006.021
Published: Kem. Ind. 56 (3) (2007) 151–162
Paper reference number: KUI-21/2006
Paper type: Conference paper
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Nitro Compounds as Solvents, Drugs, Intermediates and Explosives

S. Mutak

Abstract

This report is focused partly on the chemical development of some chemical functional groups, and partly on our own results connected with research by Vladimir Prelog in the last period of his work. The period Vladimir Prelog spent in Zagreb marked the beginning of the development of organic synthetic chemistry at the University of Zagreb and at the pharmaceutical company Kaštel, later PLIVA. One approach he took was the synthesis of new potentially active compounds, but more important was the development of a rational and economical procedure for the synthesis of known active compounds. A start was made with the synthesis of azo dyes and quinine analogs. In the last period of his work on chemistry, Prof. Prelog and visiting collaborators, mostly from PLIVA, studied the enantioselectivity of chiral ionophores, such as lyphophyl tartaric acid esters and spirobifluorene crown ethers towards some biologically active amino alcohols by intramolecular binding. The first and most successful result of the collaboration between Kaštel and Vladimir Prelog, was the early entry into the market with sulfanylamide. The key intermediate for the synthesis of sulfanylamide and other subsequently discovered sulfonamides was nitrobenzene. Organic nitro compounds now have a broad application in fine chemical production, as solvents, intermediates and final products. Simple aliphatic and aromatic nitro compounds are used as solvents and reagents; others have been used as intermediates in the synthesis of amino, hydroxy, halogen, sulpho, keto or other functional groups. Some nitro compounds are important active pharmaceuticals, including the Ca-antagonist nifedipine, the anthelmithic metronidazol or the coronary dilatator dinitroisosorbide, while others are explosives like hexogen, octogen or trinitrotoluene. It is known that some nitro compounds are both useful drugs and explosives including the nitro esters nitroglycerine or pentrite. In PLIVA, the nitration process was used in the production of various active pharmaceuticals, such as pyridoxine hydrochloride, metronidazole, methoprolol tartarate, chlortalidone, dinitroisosorbide and lampren. Further synthetic processes were developed in which purchased nitro compounds were used as intermediates for the production of active compounds with nitro or other functional groups. In 1991 when the war broke out in Croatia, some PLIVA chemists were involved in the development and production of explosives from nitro compounds. Thanks to the broad experience and tradition in organic synthesis, within a short time, a laboratory procedure was developed, a semi-production plant on a separate location was adapted and production of the most powerful brisant explosive, octogen had started. Later, an industrial process for the production of pentrite was developed and its trial production started. During this period, laboratory procedures for some other explosives were developed.

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Keywords

chiral ionophores, aminoalcohols, enantioselectivity, nitro compounds, reduction of nitro to amino, explosives