Alex.Greene-Log

Journal Article Analysis DOI

Introduction
Sarin is a one of the strongest actylecholine blockers and there are many different ways to prepare sarin, but some processes give impure products or have many steps. This paper will deal with two ways that give pure product and are relatively simple

First Process
Add carbonyl chloride to di-isoproply methylphosphonate to get an intermediate which you then react with sodium fluoride to get Sarin.

Second Process
2 propanol is reacted with equal moles of methphosphonic dichloride and methylphosphonic difluoride. This reaction takes place in an unreactive solvent and Sarin is the end product

Physical Properties
The physical properties of Sarin were determined using very pure samples The toxicity of the sarin was a concern and safety measures were taken to prevent exposure.

Experimental Section
The ends of the testing apparatus had drying tubes for protection and all glassware which would contact phosphonofluoridates was soaked in 10% NaOH for six hours before use.

Isoproply Methylphosponochloridate (II)
The carbonyl chloride was forced through the di-isopropyl methylphosphonate for 10 hours while stirring with the temperature between 20-30 degrees. The solution sat for a night and then the excess carbonyl and isopropyl chlorides were removed and the product of distillation was phosphonochloridate.

Isoproply-N-Phenylmethylphosphonoamidate
Aniline was added to phsophonochloridate drop wise, then the mixture was refluxed for 30 minutes, cooled, filtered, washed with dilute HCl and water, dried by calcium carbonate and then evaporated. The remainder was then crystallized in petroleum and the recrystallized from 50% ethanol

Methylphosphonic Difluoride
Methylphosphonic dichloride was melted and exposed to HF until the temperature reached 75, HCl was consistently given off. Under lower pressure the products were degassed, then refluxed for 30 minutes, and fractionated

Isopropyl Methylphosphonofluoridate
Isoproply Methylphosponochloridate was refluxed with NaF and methylene chloride for 4 hours; once cooled the product was washed with methylene chloride. Excess solvent was eliminated by reducing the pressure and the final product obtained.

Methylphosphonic Dichloride
Methylphosphonic Difluoride and methylene chloride were heated together to reflux temperature, then the heat was removed and 2 propanol was added so that the mixture boiled. The product was refluxed for 60 minutes, evaporated and the residue fractionated and obtained.

Physical Constants
Isopropyl methylphosphonofluoridate had two fractions with a 10:1 ratio The beginning and end portions equaled 10% of separation and after the second fraction all samples were within the error limits

Calculated properties all followed an appropriate method for determination

Acknowledgements
Help with the methylphosphonic difluoride preparation and microanalysis were noted

Log 1. http://dx.doi.org/10.1016/j.cbi.2013.09.015 -Limitation of Treating Chemcial weapons (used) 2. http://dx.doi.org/10.1038/nm1013-1194 -Article on Sarin Gas attacks=need better antodotes (used) 3. http://dx.doi.org/10.1039/JR9600001553 -Preperation of Sarin (used) 4. http://dx.doi.org/10.1002/jat.998 Inhailation Toxicity (used) 5. http://dx.doi.org/10.1016/S0196-0644(96)70052-5 Tokoyo Subway Victums (used) 6. http://dx.doi.org/10.1097/SMJ.0b013e31827cd12d Used 7. http://www.atsdr.cdc.gov/MMG/MMG.asp?id=523&tid=93 (used) 8. 9. http://dx.doi.org/10.1007/s11064-012-0896-9 (Used) 10. http://dx.doi.org/10.1021/jo00249a046 Synthesis of Sarin 11. http://dx.doi.org/10.1136/oem.54.10.697 - Affects of Sarin on Japan Rescue Workers (used) 12. http://dx.doi.org/10.1016/S0278-6915(02)00079-0 -Long Term affects of Sarin (used) 13. http://dx.doi.org/10.1021/bi982678l Atomic Affects of Sarin (Used) 14. http://dx.doi.org/10.1001/archneur.57.4.600. -History of Sarin (used) 15. http://dx.doi.org/10.1016/j.tox.2005.06.011 History of Sarin (used) 16. [|Link] Hazards of Chemcial Weapons Realeased During War (Used) 17. 10.1038/sj.bjp.0706474 Neutrotransmitters Brown (Used) 18. http://dx.doi.org/10.1006/taap.2000.9060 Intravenous and Inhalation Toxicokinetics of Sarin Stereoisomers in Atropinized Guinea Pigs (Used)

Outline-Sarin Chemical Classificatiaon History Chemical Make-up Synthesis Physiological Effects Detection Treatment History of Use Conclusions