Chloropicrine

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Structural formula
Structural formula of chloropicrin
General
Surname Chloropicrine
other names
  • Trichloronitromethane
  • Nitrochloroform
  • Knock
Molecular formula Cl 3 CNO 2
Brief description

colorless, volatile liquid

External identifiers / databases
CAS number 76-06-2
EC number 200-930-9
ECHA InfoCard 100,000,847
PubChem 6423
ChemSpider 13861343
Wikidata Q423065
properties
Molar mass 164.38 g · mol -1
Physical state

liquid

density

1.64 g cm −3 (20 ° C)

Melting point

−64 ° C

boiling point

111.9 ° C

Vapor pressure

32 h Pa (25 ° C)

solubility

bad in water (2.27 g l −1 )

Refractive index

1.4611 (20 ° C)

safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic

danger

H and P phrases H: 302-330-315-319-335
P: 260-284-305 + 351 + 338-310
MAK
  • DFG : 0.1 ml m −3 or 0.68 mg m −3
  • Switzerland: 0.1 ml m −3 or 0.7 mg m −3
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

Chloropicrin , or according to IUPAC : trichloronitromethane , is a chemical warfare agent from the group of lung warfare agents . He was in World War I a . a. used under the designation " Grünkreuz-1 ". The common name of chloropicrin is in French also Aquinite and British PS .

history

Chloropicrin was discovered in 1848 by the British chemist John Stenhouse when chlorinated lime was reacted with picric acid .

Chloropicrin was used as a warfare agent Grünkreuz-1 in various German cannons , howitzers and mortars and was used for the first time in mid-1916. This warfare agent was originally introduced by the Russian army , but the German soon followed suit.

properties

Chloropicrine is a colorless, slightly oily and volatile liquid with a penetrating odor and high vapor pressure. According to Antoine, the vapor pressure function results from log 10 (P) = A− (B / (T + C)) (P in bar, T in K) with A = 4.35889, B = 1506.333 and C = −39.369 in the temperature range from 247.7 to 385.1 K. The compound is sparingly soluble in water. Chloropicrin can explode when distilled.

Manufacturing

Chloropicrin is accessible by reacting nitromethane with sodium hypochlorite .

use

Chloropicrin is used for disinfection used, and to soils and seeds to sterilize .

Biological importance

Chloropicrine causes skin blisters in humans and leads to eye irritation and breathing difficulties. The development of toxic pulmonary edema is specific to lung warfare agent poisoning, which is accompanied by shortness of breath, coarse-bubble breathing noises and foamy-red sputum. The victim is anxious, has chest pain, and shows signs of impending shock . Since symptoms can be delayed for hours, the possible exposure time must be taken into account. The poisoning can lead to serious illness and death from suffocation. Already 0.12 g per m³ of air are life-threatening.

As with all lung warfare agents, a filter mask provides adequate protection for a limited time. Alcoholic sodium sulfide solutions have proven effective for decontamination . This creates carbon and nitrogen oxides as well as some harmless sulfur compounds.

Individual evidence

  1. ↑ a b c d e f g h i Entry on chloropicrin in the GESTIS substance database of the IFA , accessed on February 1, 2016(JavaScript required) .
  2. ↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-494.
  3. ↑ Entry on trichloronitromethane in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  4. ↑ Swiss Accident Insurance Fund (Suva): Limit values ​​- current MAK and BAT values (search for 76-06-2 or chloropicrin ), accessed on November 2, 2015.
  5. ↑ J. Stenhouse, Ueber Chloropikrin in Journal für Praktische Chemie 45 , 56-61 (1848). - Chlorpicrin in Annalen der Chemie und Pharmacie 66 , 241-247 (1848).
  6. ↑ AW Hofmann, Ueber Synthesen des Guanidins in Annalen der Chemie und Pharmacie 139 , 107-115 (1866). - page 111.
  7. ↑ Stull, DR: Vapor Pressure of Pure Substances Organic Compounds in Ind. Eng. Chem. 39 (1947) 517-540.
  8. ↑ a b Entry on chloropicrin. In: Römpp Online . Georg Thieme Verlag, accessed on February 7, 2019.
  9. ↑ Sheldon B. Markofsky "Nitro Compounds, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. - R. Preibisch, About Nitrocarbol in Journal of Applied Chemistry 116 , 309-327 (1873).

See also