Ko) Cuemicat Connections 5A Nitroglycerin: An Explosive and a Drug ‘in 1847, Ascanio Sobrero (1812-1888) discovered that 1,2,3-propanetriol, more commonly called glycerin, reacts with nitric acid in the presence of sulfuric acid to give a pale yellow, cily liquid called nitroglycerin. Sobrero also discovered the explo- sive properties ofthis compound; when he heated a small quantity oft, it exploded! cH, O8 Hs—ONO, CH—OH + 8HNO, > CH—ONO, + 3H,0 CH,—OH CH,—ONO, 1,2,3-Propanetriol (Glycerol, Glycerin) 1,2,3-Propanetriol trinitrate (Nitroglyeerin) Nitroglycerin very soon became widely used for blasting in the construction of canals, tunnels, roads, and mines and, of course, for warfare, One problem with the use of nitroglycerin was soon recognized It was difficult to handle safely, and accidental explosions occurred frequently. The Swedish chemist Alfred Nobel (1833-1896), who a ) discovered that a clay-like substance called diatomaceous earth absorbs nitroglycerin so that it wll not explode without a fuse, solved this problem. He gave the name dynamite to this mixture of nitroglycerin, diatomaceous earth, and sodium carbonate. Surprising as it may seem, nitroglycerin is used in medicine to treat angina pectoris, the symptoms of which are sharp chest pains caused by reduced flow of blood in the coronary artery. Nitroglycerin, which is available in liquid form (diluted with alcohol to render it nonexplosive, tablet form, or paste form, relaxes the smooth muscles of blood vessels, causing dilation of the coronary artery. This dilation, in turn, allows more blood to reach the heart. When Nobel became il with heart disease, his physicians advised him to take nitroglycerin to relieve his chest pains. He refused, saying he could not understand how the explosive could relieve chest pains. It took science more than 100 years to find the answer. We now know that nitric oxide, NO, derived from the nitro groups of nitroglycerin, relieves the pain (see Chemical Connections 16F). (a) Nitroglycern is more stable if absorbed onto an inet soli, a combination called dynamite, (b) The fortune of Alfred Nobel, 1833-1896, was built on the manufacture of dynamite and now funds the Nobel Prizes. i