Tabun ( tabun ) - an organophosphorus compound , dimethylamide cyanophosphoric acid ethyl ester, colorless, mobile, with a pleasant fruity odor liquid with a boiling point of 220 ° C, a melting point of −50 ° C, poorly soluble in water (about 12%), good in organic solvents. It belongs to the nerve agents , was in service under the symbols "Trilon 83", "T83", "D7" and "Gelan" [1] .
Herd | |
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Are common | |
| Chem. formula | C₅H₁₁N₂O₂P |
Classification | |
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| Chemspider | |
SMILES | |
CCOP (= O) (C # N) N (C) C | |
Inchi | |
1S / C5H11N2O2P / c1-4-9-10 (8.5-6) 7 (2) 3 / h4H2.1-3H3 | |
| Data are given for standard conditions (25 ℃, 100 kPa) , unless otherwise specified. | |
After appearing in service in the early 50s of the 20th century, Zoman and Sarin lost its military significance, however, it was included by the UN Convention on the Prohibition of Chemical Weapons of 1993 into the list of toxic chemicals 1-A [1] .
Content
Appearance history
Tabun was first synthesized in 1936 by the German chemist Gerhard Schrader ( Third Reich ) [1] . Before the Second World War, he headed the research laboratory of the IG Farbenindustry concern in Leverkusen and, in searching for effective insecticides, he discovered a number of highly toxic fluorine-containing compounds, among which were fluoride-organic phosphorus acids. This find immediately found application in the military chemical field, and G. Schrader completely switched to the study of organophosphorus substances [2] . In the same year, the first samples of the Trilon 83, later called a herd, were transferred to the chemical laboratory of the military technical institute in Spandau (not far from Berlin ) to assess the combat effectiveness. In September 1939, the concern “ IG Farbenindustry ” received a state order for the construction of an industrial plant for the production of a herd with a design capacity of 1000 tons per month. The first 138 tons of herd were received in September 1942, and in May 1943 the plant reached the declared capacity, although it continued to work with underloading. However, this did not prevent Nazi Germany from accumulating a stock of 8770 tons of herd by the end of World War II [2] .
Synthesis and properties
Tabun is obtained by sequential interaction of phosphorus oxychloride POCl 3 with an excess of dimethylamine , then with ethanol and potassium cyanide :
- POCl 3 + 2 (CH 3 ) 2 NH (CH 3 ) 2 NP (O) Cl 2 + (CH 3 ) 2 NH • HCl
- (CH 3 ) 2 NP (O) Cl 2 + C 2 H 5 OH (CH 3 ) 2 NP (O) ClOC 2 H 5 + HCl
- (CH 3 ) 2 NP (O) ClOC 2 H 5 + KCN (CH 3 ) 2 NP (O) (CN) OC 2 H 5 + KCl
- (CH 3 ) 2 NP (O) Cl 2 + C 2 H 5 OH (CH 3 ) 2 NP (O) ClOC 2 H 5 + HCl
Slowly hydrolyzed with water, in an acidic environment, the hydrolysis is accelerated, while dimethylamine is cleaved:
- (CH 3 ) 2 NP (O) (CN) OC 2 H 5 + H 2 O + HCl (CH 3 ) 2 NH • HCl + HOP (O) (CN) OC 2 H 5
Quickly hydrolyzed in alkali solutions, cleaving cyanide ion:
- (CH 3 ) 2 NP (O) (CN) OC 2 H 5 + NaOH (CH 3 ) 2 NP (O) (OH) OC 2 H 5 + NaCN
It easily interacts with ammonia and amine solutions, which is used for degassing a herd. Degassing products are poisonous because they contain hydrocyanic acid salts.
Toxicity
The herd is poisonous, highly toxic, a nerve agent , or a cholinesterase inhibitor. The lethal concentration of the herd in the air is 0.4 mg / l (1 min.), When it comes into contact with the skin in liquid form, it is 50-70 mg / kg; at a concentration of 0.01 mg / l (2 min.), the herd causes strong miosis (constriction of the pupil). Protection against herd is a gas mask in combination with protective overalls, antidotes , for example, atropine .
Notes
- ↑ 1 2 3 Tabun // Military Encyclopedia / S. B. Ivanov . - Moscow : Military Publishing House , 2003. - Vol. 7. - p. 727. - ISBN 5-203-01874-X .
- ↑ 1 2 Volkovsky NL Poisonous substances of nerve action // Encyclopedia of modern weapons and military equipment. - St. Petersburg: Polygon-Ast, 1997. - T. 1. - p. 69. - ISBN 5-89173-004-9 .
See also
- Sarin
- Soman
- VX
- Gv