Chemical Education Today
Isoamyl Nitrite Can Cause Serious Explosions Alkyl nitrites belong to a class of organic compounds with the general formula RONO, where R is an alkyl group. Thus, they are esters of nitrous acid. Alkyl nitrites are useful reagents for organic synthesis, of which isoamyl nitrite (isopentyl nitrite) is often used (1-3). The safety data sheets concerning isoamyl nitrite show that the compound is highly flammable and a vapor-air mixture can cause explosions (4, 5). However, the accident we experienced several months ago revealed that the reagent could explode even if kept in a closed container. The reagent was used for synthetic purposes and then the half-empty bottle was left closed in the refrigerator for few years. Three weeks before the accident, the refrigerator had broken down and the bottle had been kept at room temperature for a few days before it was transferred to another refrigerator. Shortly after the transfer, the bottle exploded causing devastation to the interior of the refrigerator. Fortunately, nobody was hurt, but the laboratory had to be closed for 2 weeks owing to the persistent smell. HPLC examination of the reagent remnants showed that the reagent was decomposed to a large extent and the residue was contaminated with a significant quantity of isoamyl alcohol (3-methylbutan-1-ol).
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There are two important conclusions that can be drawn from that accident: (1) great caution should be exercised when handling isoamyl nitrite, particularly if the reagent was sampled and then has been stored for long time or at temperatures above 4 °C and (2) the safety data sheet should be supplemented with a remark that the substance presents explosion hazards on prolonged storage. Literature Cited 1. Detty, M. R.; Logan, M. E. Isopentyl Nitrite. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley and Sons: New York 1995; Vol. 4, pp 2908-2911. 2. Pelter, M. W.; Pelter, L. S. W.; Colovic, D.; Strug, R. J. Chem. Educ. 2004, 81, 111–112. 3. Chen, Y. K.; Jeon, S.-J.; Walsh, P. J.; Nugent, W. A. Org. Synth. 2005, 82, 87–90. 4. Material Safety Data Sheet. Isoamyl nitrite MSDS. http://www. sciencelab.com (accessed Feb 2010). 5. International Chemical Safety Cards. http://www.cdc.gov/niosh/ ipcsneng/neng1012.html (accessed Feb 2010). Marek K. Bernard Department of Organic Chemistry, University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Pozna n, Poland
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r 2010 American Chemical Society and Division of Chemical Education, Inc. pubs.acs.org/jchemeduc Vol. 87 No. 6 June 2010 10.1021/ed800172b Published on Web 03/12/2010
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Journal of Chemical Education
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