Zoman is an organophosphorus substance, a colorless liquid, which, according to various sources, has the smell of apples, camphor or a faint smell of mowed hay. Poisonous nerve agent. In many properties, it is very similar to sarin , but it is more toxic by more than 2.5 times. The resistance of soman is slightly higher than that of sarin. A mixture of four stereoisomers without separation is used.
| Soman | |
|---|---|
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| Are common | |
| Systematic name | 2- (Fluoromethylphosphoryl) hydroxy-3,3-dimethylbutane |
| Abbreviations | GD, EA 1210, PFMP |
| Traditional names | Methylphosphonic Acid Fluoride Pinacolinic Ester |
| Chem. formula | C₇H₁₆FO₂P |
| Physical properties | |
| condition | liquid |
| Molar mass | 182.17 g / mol |
| Density | 1,0131 [1] |
| Thermal properties | |
| T. melt. | −80 ° C |
| T. bale. | about 190 ° C (with decomposition) [1] ° C |
| T. decomp. | more than 150 [1] |
| Steam pressure | 0.3 mmHg Art. at +20 ° C |
| Chemical properties | |
| Solubility in water | bad |
| Solubility in alcohols, ketones, esters, alkyl halides | good |
| Optical properties | |
| Refractive index | 1.4080 (sodium D-line) [1] |
| Classification | |
| Reg. CAS number | |
| PubChem | |
| Smiles | |
| Inchi | |
| Chebi | |
| ChemSpider | |
| Security | |
| MPC | 5 · 10 -7 mg / m 3 (in air) |
| NFPA 704 |  one four one |
Synthesis and Properties
Soman is an analogue of sarin , both of these compounds are esters of methyl fluorophosphonic acid: soman - pinacolyl ether, sarin - isopropyl. The chemical properties of soman are similar to those of sarin, however, its reactivity with respect to nucleophiles is reduced due to steric difficulties created by the more voluminous pinacolyl substituent.
Soman is poorly soluble in water (1.5% at +25 ° C), readily soluble in alcohols and ketones, as well as in esters and alkyl halides. In acidic, neutral, and slightly alkaline media, it hydrolyzes slowly; the slowest hydrolysis is observed at pH = 4 . The hydrolysis time by 50% at +30 ° C and pH 2, 4 and 7 is respectively 6.4, 250 and 41 hours. At pH> 10, it hydrolyzes rapidly; in 5% NaOH, the reaction is completed after 5 minutes, easily reacts with solutions of ammonia and amines. At a temperature> 150 ° C it decomposes completely, the destruction is accelerated in the presence of acidic substances. The boiling point at atmospheric pressure is about 190 ° C, at a pressure of 0.1 mm RT. Art. 42 ° C. Density 1.0131 g / cm 3 (at +20 ° C). The refractive index is 1.4080 (for the yellow doublet of sodium) [1] .
The synthesis of soman is similar to the synthesis of sarin - it is carried out by the esterification of pinacolyl alcohol (3,3-dimethylbutan-2-ol) with a mixture of methylphosphonic acid dichloro and difluorohydrides:
- CH 3 POCl 2 + CH 3 POF 2 + 2CH 3 CH (OH) C (CH 3 ) 3 2CH 3 P (= O) (F) OCH (CH 3 ) C (CH 3 ) 3
Toxicity
Soman is a cholinesterase inhibitor. The first signs of damage are observed at concentrations of about 0.0005 mg / l after a minute (narrowing of the pupils of the eyes, difficulty breathing). The lethal concentration when acting through the respiratory system of 0.03 mg · min / L. The lethal concentration during resorption through the skin is 2 mg / kg . Protection against soman - gas mask and skin protection, as well as antidotes . It was first synthesized in Germany by Richard Kuhn in 1944 for use as a chemical warfare agent .
As atropine or pralidoxime can be used as antidotes , diazepam can be used to relieve side symptoms (anxiety, emotional stress).
GD Agent Synthesis
Zoman metabolism.
Notes
- ↑ 1 2 3 4 5 Emelyanov V.I. Zoman // Chemical Encyclopedia: 5 t / Knunyants I.L. - M .: Soviet Encyclopedia , 1990. - T. 2: Duffa-Copper. - S. 175 .-- 671 p. - 100,000 copies. - ISBN 5-85270-035-5 .