Synthesis and Storage Stability of Diisopropylfluorophosphate

• Main Authors: Derik R. Heiss, Donald W. Zehnder, David A. Jett, Gennady E. Platoff, David T. Yeung, Bobby N. Brewer
• Format: Article
• Language: English
• Published: Hindawi Limited 2016-01-01
• Series: Journal of Chemistry
• Online Access: http://dx.doi.org/10.1155/2016/3190891
• ISSN: 2090-9063; 2090-9071

Diisopropylfluorophosphate (DFP) is a potent acetylcholinesterase inhibitor commonly used in toxicological studies as an organophosphorus nerve agent surrogate. However, LD50 values for DFP in the same species can differ widely even within the same laboratory, possibly due to the use of degraded DFP. The objectives here were to identify an efficient synthesis route for high purity DFP and assess the storage stability of both the in-house synthesized and commercial source of DFP at the manufacturer-recommended storage temperature of 4°C, as well as −10°C and −80°C. After 393 days, the commercial DFP stored at 4°C experienced significant degradation, while only minor degradation was observed at −10°C and none was observed at −80°C. DFP prepared using the newly identified synthesis route was significantly more stable, exhibiting only minor degradation at 4°C and none at −10°C or −80°C. The major degradation product was the monoacid derivative diisopropylphosphate, formed via hydrolysis of DFP. It was also found that storing DFP in glass containers may accelerate the degradation process by generating water in situ as hydrolytically generated hydrofluoric acid attacks the silica in the glass. Based on the results here, it is recommended that DFP be stored at or below −10°C, preferably in air-tight, nonglass containers.