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Wikipedia

Pentachlorobenzene

December 15, 2023

Pentachlorobenzene (PeCB) is a chemical compound with the molecular formula C6HCl5 which is a chlorinated aromatic hydrocarbon. It consists of a benzene ring substituted with five chlorine atoms. PeCB was once used industrially for a variety of uses, but because of environmental concerns there are currently no large scale uses of PeCB.[4] Pentachlorobenzene is a known persistent organic pollutant (POP) and banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009.[5]

Pentachlorobenzene
Names
Preferred IUPAC name
Pentachlorobenzene
Other names
PeCB
Identifiers
  • 608-93-5 Y
3D model (JSmol)
  • Interactive image
1911550
ChEBI
  • CHEBI:47136 Y
ChEMBL
  • ChEMBL44628 Y
ChemSpider
  • 21106570 Y
ECHA InfoCard 100.009.248
EC Number
  • 602-074-00-5
51144
KEGG
  • C18141
  • 11855
RTECS number
  • DA6640000
UNII
  • D62GWO6832 Y
  • DTXSID7024247
  • InChI=1S/C6HCl5/c7-2-1-3(8)5(10)6(11)4(2)9/h1H N
    Key: CEOCDNVZRAIOQZ-UHFFFAOYSA-N N
  • InChI=1/C6HCl5/c7-2-1-3(8)5(10)6(11)4(2)9/h1H
    Key: CEOCDNVZRAIOQZ-UHFFFAOYAV
  • c1c(Cl)c(Cl)c(Cl)c(Cl)c1Cl
Properties
C6HCl5
Molar mass 250.32 g·mol−1
Appearance White or colorless crystals
Density 1.8 g/cm3[1]
Melting point 86 °C (187 °F; 359 K)[1]
Boiling point 275 to 277 °C (527 to 531 °F; 548 to 550 K)[1]
0.68 mg/L[2]
Hazards
GHS labelling:
Danger
H228, H302, H410
P210, P240, P241, P264, P270, P273, P280, P301+P312, P330, P370+P378, P391, P501
Lethal dose or concentration (LD, LC):
rat: 1080 mg/kg[3]
mouse: 1175 mg/kg[3]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Production edit

PeCB can be produced as a byproduct of the manufacture of carbon tetrachloride and benzene. It is extracted by distillation and crystallization. The direct production of pure PeCB is not practical because of the simultaneous production of other chlorinated compounds. Since PeCB is generally produced in small quantities in the chlorination of benzene, it is also contained in other chlorobenzenes (dichlorobenzenes, trichlorobenzenes etc.)

Today, a majority of the PeCB released into the environment is a result of backyard trash burning and municipal waste incineration.[4]

Uses edit

PeCB was used as an intermediate in the manufacture of pesticides, particularly the fungicide pentachloronitrobenzene.[3] Pentachloronitrobenzene is now made by the chlorination of nitrobenzene in order to avoid the use of PeCB.[4]

PeCB was a component of a mixture of chlorobenzenes added to products containing polychlorinated biphenyls in order to reduce viscosity.[4] PeCB has also been used as a fire retardant.[3]

Safety and regulation edit

PeCB is a persistent organic pollutant, allowing an accumulation in the food chain.[1][4] Consequently, pentachlorobenzene was added in 2009 to the list of chemical compounds covered by the Stockholm Convention, an international treaty which restricts the production and use of persistent organic pollutants.[6][7] PeCB has been banned in the European Union since 2002.

PeCB is very toxic to aquatic organisms, and decomposes on heating or on burning with the formation of toxic, corrosive fumes including hydrogen chloride.[1] Combustion of PeCB may also result in the formation of polychlorinated dibenzodioxins ("dioxins") and polychlorinated dibenzofurans.

See also edit

References edit

  1. ^ a b c d e Pentachlorobenzene Safety Card, International Programme on Chemical Safety
  2. ^ Shen, L., Wania, F., Lei, Y. D., Teixeira, C., Muir, D. C. G., Bidleman, T. F. (2005). "Compilation, evaluation, and selection of physical-chemical property data for organochlorine pesticides". J. Chem. Eng. Data. 50 (3): 742–768. doi:10.1021/je049693f.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ a b c d Pentachlorobenzene Fact Sheet, U.S. Environmental Protection Agency
  4. ^ a b c d e Pentachlorobenzene – Sources, environmental fate and risk characterization 2008-12-27 at the Wayback Machine, Robert E. Bailey, EuroChlor, July 2007
  5. ^ Press Release – COP4 – Geneva, 8 May 2009: Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty, 2009.
  6. ^ Governments unite to step-up reduction on global DDT reliance and add nine new chemicals under international treaty, Stockholm Convention on Persistent Organic Pollutants, 9 May 2009
  7. ^ Adding the 'Nasty Nine' to the 'Dirty Dozen' 2013-12-06 at the Wayback Machine, thedailygreen.com

December 15, 2023
pentachlorobenzene, pecb, chemical, compound, with, molecular, formula, c6hcl5, which, chlorinated, aromatic, hydrocarbon, consists, benzene, ring, substituted, with, five, chlorine, atoms, pecb, once, used, industrially, variety, uses, because, environmental,. Pentachlorobenzene PeCB is a chemical compound with the molecular formula C6HCl5 which is a chlorinated aromatic hydrocarbon It consists of a benzene ring substituted with five chlorine atoms PeCB was once used industrially for a variety of uses but because of environmental concerns there are currently no large scale uses of PeCB 4 Pentachlorobenzene is a known persistent organic pollutant POP and banned globally by the Stockholm Convention on Persistent Organic Pollutants in 2009 5 Pentachlorobenzene NamesPreferred IUPAC name PentachlorobenzeneOther names PeCBIdentifiersCAS Number 608 93 5 Y3D model JSmol Interactive imageBeilstein Reference 1911550ChEBI CHEBI 47136 YChEMBL ChEMBL44628 YChemSpider 21106570 YECHA InfoCard 100 009 248EC Number 602 074 00 5Gmelin Reference 51144KEGG C18141PubChem CID 11855RTECS number DA6640000UNII D62GWO6832 YCompTox Dashboard EPA DTXSID7024247InChI InChI 1S C6HCl5 c7 2 1 3 8 5 10 6 11 4 2 9 h1H NKey CEOCDNVZRAIOQZ UHFFFAOYSA N NInChI 1 C6HCl5 c7 2 1 3 8 5 10 6 11 4 2 9 h1HKey CEOCDNVZRAIOQZ UHFFFAOYAVSMILES c1c Cl c Cl c Cl c Cl c1ClPropertiesChemical formula C 6H Cl 5Molar mass 250 32 g mol 1Appearance White or colorless crystalsDensity 1 8 g cm3 1 Melting point 86 C 187 F 359 K 1 Boiling point 275 to 277 C 527 to 531 F 548 to 550 K 1 Solubility in water 0 68 mg L 2 HazardsGHS labelling PictogramsSignal word DangerHazard statements H228 H302 H410Precautionary statements P210 P240 P241 P264 P270 P273 P280 P301 P312 P330 P370 P378 P391 P501Lethal dose or concentration LD LC LD50 median dose rat 1080 mg kg 3 mouse 1175 mg kg 3 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Production 2 Uses 3 Safety and regulation 4 See also 5 ReferencesProduction editPeCB can be produced as a byproduct of the manufacture of carbon tetrachloride and benzene It is extracted by distillation and crystallization The direct production of pure PeCB is not practical because of the simultaneous production of other chlorinated compounds Since PeCB is generally produced in small quantities in the chlorination of benzene it is also contained in other chlorobenzenes dichlorobenzenes trichlorobenzenes etc Today a majority of the PeCB released into the environment is a result of backyard trash burning and municipal waste incineration 4 Uses editPeCB was used as an intermediate in the manufacture of pesticides particularly the fungicide pentachloronitrobenzene 3 Pentachloronitrobenzene is now made by the chlorination of nitrobenzene in order to avoid the use of PeCB 4 PeCB was a component of a mixture of chlorobenzenes added to products containing polychlorinated biphenyls in order to reduce viscosity 4 PeCB has also been used as a fire retardant 3 Safety and regulation editPeCB is a persistent organic pollutant allowing an accumulation in the food chain 1 4 Consequently pentachlorobenzene was added in 2009 to the list of chemical compounds covered by the Stockholm Convention an international treaty which restricts the production and use of persistent organic pollutants 6 7 PeCB has been banned in the European Union since 2002 PeCB is very toxic to aquatic organisms and decomposes on heating or on burning with the formation of toxic corrosive fumes including hydrogen chloride 1 Combustion of PeCB may also result in the formation of polychlorinated dibenzodioxins dioxins and polychlorinated dibenzofurans See also editChlorobenzenes different numbers of chlorine substituents Pentafluorobenzene PentachlorobenzenethiolReferences edit a b c d e Pentachlorobenzene Safety Card International Programme on Chemical Safety Shen L Wania F Lei Y D Teixeira C Muir D C G Bidleman T F 2005 Compilation evaluation and selection of physical chemical property data for organochlorine pesticides J Chem Eng Data 50 3 742 768 doi 10 1021 je049693f a href Template Cite journal html title Template Cite journal cite journal a CS1 maint multiple names authors list link a b c d Pentachlorobenzene Fact Sheet U S Environmental Protection Agency a b c d e Pentachlorobenzene Sources environmental fate and risk characterization Archived 2008 12 27 at the Wayback Machine Robert E Bailey EuroChlor July 2007 Press Release COP4 Geneva 8 May 2009 Governments unite to step up reduction on global DDT reliance and add nine new chemicals under international treaty 2009 Governments unite to step up reduction on global DDT reliance and add nine new chemicals under international treaty Stockholm Convention on Persistent Organic Pollutants 9 May 2009 Adding the Nasty Nine to the Dirty Dozen Archived 2013 12 06 at the Wayback Machine thedailygreen com Retrieved from https en wikipedia org w index php title Pentachlorobenzene amp oldid 1161716501, wikipedia, wiki, book, books, library,

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