1,3-Dichloropropene

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1,3-Dichloropropene
Skeletal formula of the trans isomer
Skeletal formula of the cis isomer
Ball-and-stick model of the trans isomer
Ball-and-stick model of the cis isomer
Names
IUPAC name
1,3-dichloroprop-1-ene
Systematic IUPAC name
1-Propene, 1,3-dichloro-, (1E)-
Other names
AQL Agrocelhone, DD92, 1,3-D, Dorlone, Nematox, Telone, Nemex, cis-Dichloropropene, Di-Trapex CP, Vorlex 201, dichloro-1,3-propene, 1,3-dichloro-1-propene, 1,3-dichloro-2-propene, alpha-chloroallylchloride, chloroallylchloride, gamma-chloroallylchloride, chloroallyl chloride, chloroorpropenyl chloride, 1,3-dichloropropylene, 3-D, DCP, 3-Chloroallyl chloride
Identifiers
542-75-6 YesY
ChEBI CHEBI:18918 N
ChEMBL ChEMBL155926 YesY
ChemSpider 23117 YesY
EC number 208-826-5
Jmol-3D images Image
KEGG C18627 YesY
MeSH 1,3-dichloro-1-propene
PubChem 24726
RTECS number UC8310000
UNII 9H780918D0 YesY
Properties
C3H4Cl2
Molar mass 110.97 g/mol
Appearance Colorless to straw-colored liquid
Odor sweet, chloroform-like
Density 1.217 g/mL (cis); 1.224 g/mL (trans)
Melting point −84.5 °C (−120.1 °F; 188.7 K)
Boiling point 104 °C (219 °F; 377 K) (cis); 112 °C (trans)
2.18 g/L (cis) @ 25 °C; 2.32 g/L (trans) @ 25 °C
log P 1.82
Vapor pressure 34.4 mm Hg @ 25 °C (cis); 23.0 mm Hg @ 25 °C (trans)
Hazards
EU Index 208-826-5
EU classification T,N
R-phrases 10-20/21-25-36/37/38-43-50/53
S-phrases (1/2-)-36/37-45-60-61
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 28 °C (82 °F; 301 K)
> 500 °C (932 °F; 773 K)
Explosive limits 5.3% - 14.5% (80 °C)
US health exposure limits (NIOSH):
none[1]
Ca TWA 1 ppm (5 mg/m3) [skin][1]
Ca [N.D.][1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

1,3-Dichloropropene, sold under diverse trade names, is an organochlorine compound. It is colorless liquid with a sweet smell. It dissolves in water and evaporates easily. It is used mainly in farming as a pesticide, specifically as a preplant fumigant and nematicide. It is widely used in the US and other countries, but is in the process of being phased out in the European Union.[2]

Production, chemical properties, biodegradation[edit]

It is a byproduct in the chlorination of propene to make allyl chloride.[3]

It is usually obtained as a mixture of the geometric isomers, called Z-1,3-dichloropropene, and E-1,3-dichloropropene. Although it was first applied in agriculture in the 1950s, at least two biodegradation pathways have evolved. One pathway degrades the chlorocarbon to acetaldehyde via chloroacrylic acid.[4]

Safety[edit]

The TLV-TWA for 1,3-dichloropropene (DCP) is 1 ppm.[5] It is a contact irritant. A wide range of complications have been reported.[6]

Carcinogenicity[edit]

Evidence for the carcinogenicity of 1,3-dichloropropene in humans is inadequate, but results from several cancer bioassays provide adequate evidence of carcinogenicity in animals. In the US, the Department of Health and Human Services (DHHS) has determined that 1,3-dichloropropene may reasonably be anticipated to be a carcinogen. The International Agency for Research on Cancer (IARC) has determined that 1,3-dichloropropene is possibly carcinogenic to humans. The EPA has classified 1,3-dichloropropene as a probable human carcinogen.[6]

Use[edit]

1,3-Dichloropropene is used as a pesticide in the following crops: [1]

1,3-Dichloropropene Use in Crops
Crop Pounds (lb) Primary Pesticide?
Tobacco 12,114,887 Yes
Potatoes 12,044,736 Yes
Sugar Beets 5,799,613 Yes
Cotton 3,735,543 Yes
Peanuts 3,463,003 Yes
Sweet Potatoes 1,210,872 Yes
Onions 674,183 Yes
Carrots 531,752 Yes
Watermelons 133,801 No
Cantaloups 121,395 No
Cucumbers 76,735 No
Strawberries 71,753 No
Sweet Peppers 28,247 No
Melons 12,471 No
Blueberries 3,090 No
Asparagus 1,105 No

Contamination[edit]

The ATSDR has extensive contamination information available.[7]

Frequency of NPL Sites with 1,3-Dichloropropene Contamination

References[edit]

  1. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0199". National Institute for Occupational Safety and Health (NIOSH). 
  2. ^ COMMISSION DECISION of 20 September 2007 concerning the non-inclusion of 1,3-dichloropropene in Annex I to Council Directive 91/414/EEC and the withdrawal of authorisations for plant protection products containing that substance, Official Journal of the European Union, 25 September 2007.
  3. ^ Ludger Krähling, Jürgen Krey, Gerald Jakobson, Johann Grolig, Leopold Miksche “Allyl Compounds” in Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH, Weinheim, 2005. Published online: 15 June 2000. doi:10.1002/14356007.a01 425
  4. ^ Gerrit J. Poelarends, Christian P. Whitman "Evolution of enzymatic activity in the tautomerase superfamily: mechanistic and structural studies of the 1,3-dichloropropene catabolic enzymes" Bioorganic Chemistry 2004, Volume 32, Pages 376–392 doi:10.1016/j.bioorg.2004.05.006.
  5. ^ Robert L. Metcalf “Insect Control” in Ullmann’s Encyclopedia of Industrial Chemistry” Wiley-VCH, Wienheim, 2002. doi:10.1002/14356007.a14_263
  6. ^ a b [2]
  7. ^ [3]

Further reading[edit]