Tetraethyl pyrophosphate

Structural formula
General
Surname	Tetraethyl pyrophosphate
other names	Tetraethyl diphosphate TEPP Bladan
Molecular formula	C 8 H 20 O 7 P 2
Brief description	hygroscopic colorless liquid
External identifiers / databases
CAS number 107-49-3 EC number 203-495-3 ECHA InfoCard 100.003.179 PubChem 7873 Wikidata Q933664
properties
Molar mass	290.19 g mol −1
Physical state	liquid
density	1.18 g cm −3
Melting point	0 ° C
boiling point	124 ° C
Vapor pressure	2.0664 Pa (° C)
solubility	miscible with water (decomposes) soluble in non-polar solvents ( acetone , benzene , chloroform )
Refractive index	1.4071
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 300-310-400 P: 264-273-280-301 + 310-302 + 350-310
MAK	Switzerland: 0.005 ml m −3 or 0.05 mg m −3
Toxicological data	0.5 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Tetraethyl pyrophosphate , abbreviated TEPP, is a chemical compound from the group of phosphoric acid esters . Its toxicity is based on the inhibition of acetylcholinesterase in nerve cells .

history

TEPP was first synthesized in the mid-19th century by the Russian chemist Vladimir Petrovich Moschnin, a student of Charles Adolphe Wurtz , in his Paris laboratory. The synthesis was repeated by Philippe de Clermont and reported to the Académie des sciences . It was not until 1932 that the enormous toxicity of the substance was reported. In 1938, Gerhard Schrader developed TEPP into one of the first organic insecticides .

presentation

TEPP can be made from diethyl chlorophosphate and water in the presence of pyridine to scavenge the hydrogen chloride .

Admission

There was never an EU approval, in Germany, Austria and Switzerland no pesticides with this active substance are approved.

Individual evidence

1. ↑ ^{a b c d} Entry on tetraethyl pyrophosphate in ChemicalBook , accessed January 20, 2014.
2. ↑ ^{a b c} data sheet TEPP, PESTANAL at Sigma-Aldrich , accessed on May 19, 2017 ( PDF ).
3. ↑ International Chemical Safety Card (ICSC) for TEPP at the National Institute for Occupational Safety and Health (NIOSH), accessed January 18, 2016.
4. ↑ ^{a b c} Entry on TEPP in the GESTIS substance database of the IFA , accessed on February 13, 2017(JavaScript required) .
5. ↑ VI Boiko, LN Onikiichuk, AV Yakovenko, VI Kal'chenko: New Syntheses of 1,1-Dichloro-2,2,2-trifluoroethyl Isocyanate and Its Reaction with Triethyl Phosphite . In: Russian Journal of General Chemistry . tape 72 , no. 8 , August 2002, p. 1313-1314 , doi : 10.1023 / A: 1020816905116 .
6. ↑ Entry on TEPP in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
7. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 107-49-3 or tetraethyl pyrophosphate ), accessed on November 2, 2015.
8. ↑ Ladislaus Szinicz: History of chemical and biological warfare agents . In: Toxicology . tape 214 , no. 3 , October 30, 2005, p. 167-181 , doi : 10.1016 / j.tox.2005.06.011 ( PDF ).
9. ↑ George Petroianu: History of organophosphorus cholinesterase inhibitor & Reactivators . In: Military Medical Science Letters . tape 84 , no. 4 , 2015, p. 182-185 ( PDF ).
10. ↑ General Directorate Health and Food Safety of the European Commission: Entry on Tetraethyl pyrophosphate (TEPP) in the EU pesticide database; Entry in the national registers of plant protection products in Switzerland , Austria and Germany ; accessed on February 22, 2016.