Chloropicrin

Chloropicrin
Chloropicrin
Identifiers
CAS number 76-06-2 YesY
ChemSpider 13861343 YesY
UNII I4JTX7Z7U2 YesY
KEGG C18445 YesY
ChEBI CHEBI:39285 YesY
Jmol-3D images Image 1
Properties
Molecular formula CCl3NO2
Molar mass 164.375
Appearance colorless liquid
Density 1.692 g/ml[1]
Melting point

-69 °C

Boiling point

112 °C (dec)

Hazards
Main hazards Extremely toxic and irritating to skin, eyes, and lungs.
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chloropicrin, also known as PS, is a chemical compound with the structural formula Cl3CNO2. This colourless highly toxic liquid was once used in chemical warfare and is currently used as a fumigant and nematocide.[2][3]

Contents

History

Chloropicrin was first discovered in 1848 by a Scottish chemist John Stenhouse. He prepared it by the reaction of a chlorinating agent with picric acid:

HOC6H2(NO2)3 + 11 NaOCl → 3 Cl3CNO2 + 3 Na2CO3 + 3 NaOH + 2 NaCl

Because of the precursor he used, Stenhouse named the compound chloropicrin, although the two compounds are structurally dissimilar.

Arguably[weasel words], chloropicrin's most famous use was in World War I. In 1917, there were reports that the Germans were testing and using a new chemical in warfare.[4] That chemical was chloropicrin. While not as lethal as other chemical weapons, it caused vomiting and was a lachrymatory agent.[4] This combination of properties forced Allied soldiers to remove their masks to vomit, exposing them to toxic gases.[4] This caused a large number of casualties on the Italian front.[4]

Preparation

Chloropicrin is manufactured by the reaction of nitromethane with sodium hypochlorite:[5]

H3CNO2 + 3 NaOCl → Cl3CNO2 + 3 NaOH

Properties

As listed in the Table, chloropicrin is a colorless liquid that is insoluble in water, with which it is stable. With a vapor pressure of 24 mm Hg, its volatility is between that of phosgene and mustard gas in persistency, although closer to phosgene because it is related to the compound.[6] Tests have shown that chloropicrin causes humans to shut their eyes involuntarily.[4] Chloropicrin can be absorbed systemically through inhalation, ingestion, and the skin. It is severely irritating to the lungs, eyes, and skin.[7] Because of these properties, chloropicrin can only be delivered in shell form as a chemical weapon.[6]

Application

Chloropicrin, today, is used as a fumigant to control pests found in the soil.[2] Although less common, it can be used as a poison for vertebrates, such as rabbits.[2] Chloropicrin is commonly used in combination with other fumigants, such as methyl bromide and sulfuryl fluoride, for increased potency and as a warning agent.[2]

Chloropicrin has been used in chemical warfare. It first appeared in 1917 when the Germans tested a new chemical weapon on the Italian front.[6] The new chemical weapon was devastating to the Allies at first, since they had never encountered it before.

Safety

Chloropicrin is a highly toxic chemical: NIOSH 1995 states that:

  • Chloropicrin is a lacrimator and a severe irritant of the respiratory system in humans; it also causes severe skin irritation on contact. When splashed onto the eye chloropicrin has caused corneal oedema and liquification of the cornea.
  • Exposure to concentrations of 15 ppm cannot be tolerated for more than 1 minute, and exposure to 4 ppm for a few seconds is temporarily disabling.
  • Exposure to 0.3-0.37 ppm chloropicrin for 3 to 30 seconds causes tearing and eye pain. Exposure to 15 ppm for a few seconds can cause respiratory tract injury.
  • Exposure to 119 ppm in air for 30 minutes is lethal; death is caused by pulmonary oedema.

Examples of industrial exposure in humans: 27 workers in a cellulose factory who were exposed to high levels of chloropicrin for 3 minutes developed pneumonitis after 3 to 12 hours of irritated coughing and difficulty on breathing; they subsequently developed pulmonary oedema, and one died.

EU classification of chloropicrin is: R22 Harmful if swallowed, R26 Very toxic by inhalation, R36/37/38 Irritating to eyes, skin and respiratory system, R43 May cause sensitisation by skin contact, R50/53 Very toxic to aquatic organisms, may cause long term adverse effects in the aquatic environment.

Because of chloropicrin's stability, protection requires highly effective absorbents, such as activated charcoal.[4] Chloropicrin, unlike its relative compound phosgene, is absorbed readily at any temperature, which may pose a threat in low or high temperature climates.[6]

The use of the substance has been restricted by the U.S. government, although such restriction is outdated now [8]

Portrayal in Media

In the 1987 Movie Dragnet, detectives Joe Friday (Dan Aykroyd) and Pep Streebeck (Tom Hanks) thwart an attempt by mad cultists to release a tanker truck of trichloronitromethane at a party attended by several prominent Los Angeles city officials.

The effects cited in explaining the substance (vomiting, suffocation, and death) are consistent with the actual chemical.

References


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Look at other dictionaries:

  • chloropicrin — [klôr΄ō pik′rin] n. [ CHLORO + PICR(IC ACID) + IN1] a colorless liquid, CCl3NO2, prepared by treating chloroform with concentrated nitric acid, and used in chemical warfare as a poison gas, and in insecticides, fungicides, etc …   English World dictionary

  • chloropicrin — /klawr euh pik rin, puy krin, klohr /, n. Chem., Mil. a colorless, somewhat oily, water insoluble, poisonous liquid, CCl3NO2, that causes lachrymation and headache: used as an insecticide, a fungicide, in organic synthesis, and as a war gas. Also …   Universalium

  • chloropicrin — chlorpikrinas statusas T sritis chemija formulė CCl₃NO₂ atitikmenys: angl. chloropicrin rus. хлорпикрин ryšiai: sinonimas – trichlornitrometanas …   Chemijos terminų aiškinamasis žodynas

  • chloropicrin — noun Etymology: German Chlorpikrin, from chlor + Greek pikros sharp more at paint Date: circa 1889 a colorless liquid CCl3NO2 that causes tears and vomiting and is used especially as a soil fumigant …   New Collegiate Dictionary

  • chloropicrin — noun The chlorinated derivative of nitromethane CClNO that is used as a pesticide and tear gas Syn: nitrochloroform, trichloronitromethane …   Wiktionary

  • chloropicrin — A toxic lung irritant and lacrimatory gas; it also causes vomiting, colic, and diarrhea, and therefore is called vomiting gas. SYN: nitrochloroform. * * * chlo·ro·pic·rin .klōr ə pik rən, .klȯr n a heavy colorl …   Medical dictionary

  • chloropicrin — n. poisonous chemical compound …   English contemporary dictionary

  • chloropicrin — chlo·ro·pic·rin …   English syllables

  • chloropicrin — chlo•ro•pic•rin [[t]ˌklɔr əˈpɪk rɪn, ˌkloʊr [/t]] also chlorpicrin n. chem. a poisonous liquid, CCl3NO2, used as an insecticide and fungicide and in chemical warfare • Etymology: 1885–90; chloro II+picr(ic acid)+ in I …   From formal English to slang

  • chloropicrin — /klɔroʊˈpɪkrən/ (say klawroh pikruhn), / ˈpaɪkrən/ (say puykruhn) noun a colourless liquid, CCl3NO2, used as an insecticide and as a chemical agent in warfare; nitrochloroform; trichloronitromethane. Also, chlorpicrin. {chloro 2 + picr(ic acid) + …  

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