Synthesis of Alkyl Methylphosphonic Acid Esters

Journal Article · Mon Aug 01 04:00:00 EDT 2005 · Phosphorus, Sulfur and Silicon and the Related Elements, 180(8):1885-1891

DOI:https://doi.org/10.1080/104265090889602· OSTI ID:15017396

Mong, Gary M; Harvey, Scott D; Campbell, James A

This manuscript describes a simple synthesis and purification of cyclohexyl methylphosphonic and isopropyl methylphosphonic acids that provides high purity (>95% purity) product in gram quantities. Based on needs for improved analytical methods for indirect detection of nerve agent use, there is an increasing demand for these nerve agent hydrolysis products. These products are not commercially available. Synthesis is based on reaction of equimolar amounts of alcohol with methylphosphonic dichloride in toluene followed by the addition of excess water (two mole equivalents). The product was then extracted from the resulting aqueous layer into chloroform. The extraction scheme proved highly effective in removing unreacted starting materials and reaction by-products.

• Research Organization: Pacific Northwest National Laboratory (PNNL), Richland, WA (US)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 15017396
• Report Number(s): PNNL-SA-40031
• Journal Information: Phosphorus, Sulfur and Silicon and the Related Elements, 180(8):1885-1891, Journal Name: Phosphorus, Sulfur and Silicon and the Related Elements, 180(8):1885-1891 Journal Issue: 8 Vol. 180
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
45 MILITARY TECHNOLOGY, WEAPONRY, AND NATIONAL DEFENSE
BIOLOGICAL WARFARE AGENTS
BY-PRODUCTS
CHEMICAL ANALYSIS
DETECTION
EXTRACTION
HYDROLYSIS
PHOSPHONIC ACID ESTERS
PURIFICATION
SYNTHESIS