Diphosgene

Monoclinic

P21 / n

A = 5.5578 (5 ) Å, b = 14.2895 (12 ) Å, c = 8.6246 (7 ) Å, β = 102.443 ( 2) °, Z = 4

  • Chloroformate
  • Trichloromethylchloroformate
  • Trichlormethylchlorkohlensäureester
  • Perstoff
  • Palit

Colorless, pungent -smelling fluid

Liquid

1.64 g · cm -3 ( 20 ° C)

-57 ° C

127.5 ° C

13.73 hPa ( 20 ° C)

  • Decomposition in water
  • Soluble in benzene, toluene and carbon tetrachloride

1.4584

Risk

Template: Infobox chemical / molecular formula search available

Diphosgene is a chlorinated, toxic chemical compound. It was like phosgene in the First World War used as a choking agent. It is also called Perstoff.

History

Diphosgene was used for the first time on 23 June 1916 by the German army at Verdun in the Fort Souville and Fort Tavannes on the Western Front as a green cross warfare agent in garnet fillings.

Production

A synthesis is obvious the chlorination of methyl formate under UV light:

Due to the high volatility of the methyl and its high, sometimes explosive reactivity of the radical chlorination of methyl chloroformate is preferred, at least in the laboratory. This is cheaply available and is obtained from phosgene and methanol:

Chemical Properties

Diphosgene decomposes on heating in 2 molecules of phosgene ( thermolysis ).

Use

Diphosgene is used as a substitute for less hazardous phosgene for example, in the preparation of carbonates, isocyanates, and isocyanides. Militarily, it was used as a chemical warfare agent (see also Green Cross).

It is also used in the laboratory as a synthetic equivalent of phosgene ( " dimeric phosgene "); However, in practice the triphosgene is more manageable.

Biological Significance

Symptoms of poisoning with phosgene or Diphosgene: Hours after inhaling troublesome cough, brownish discharge (blood admixture ), blueing of the skin ( cyanosis), pulmonary edema (accumulation of fluid in the lungs ). If left untreated, the poisoning ends with phosgene or Diphosgene in agonizing suffocation.

Safety

Diphosgene is highly toxic. The LD100 is 6 mg / L (treatment time 1 minute), the LCT50 3200 mg x min / m³ and ICT50 1600 mg x min / m³.

Proof

The resulting phosgene can be detected with test tubes.

Lattice constant CAS registry number Vapor pressure Dangerous Substances Directive (67/548/EEC) Chlorine Pulmonary agent Western Front (World War I) Thermal decomposition List of chemical warfare agents Digital Object Identifier
290363
de