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Revision as of 14:08, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{chembox}} taken from revid 456095740 of page Hexachloroethane for the Chem/Drugbox validation project (updated: 'KEGG').  Latest revision as of 12:05, 20 September 2024 edit 5.178.188.143 (talk) →External linksTag: Visual edit 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 408566085 | verifiedrevid = 461767493
| ImageFile_Ref = {{chemboximage|correct|??}} | ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Hexachloroethane-2D-stereo.png | ImageFile = Hexachloroethane-2D-stereo.png
| ImageFile1 = Hexachloroethane-3D-balls.png | ImageFile1 = Hexachloroethane-3D-balls.png
| IUPACName = Hexachloroethane | PIN = Hexachloroethane
| OtherNames = Carbon hexachloride, Ethane hexachloride, Perchloroethane, Sesquichloride of carbon
| OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| Beilstein = 1740341
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 5979 | ChemSpiderID = 5979
| PubChem = 6214 | PubChem = 6214
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| UNII = G30K3QQT4J | UNII = G30K3QQT4J
| InChI = 1/C2Cl6/c3-1(4,5)2(6,7)8 | InChI = 1/C2Cl6/c3-1(4,5)2(6,7)8
| ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 39227 | ChEBI = 39227
| SMILES = ClC(Cl)(Cl)C(Cl)(Cl)Cl | SMILES = ClC(Cl)(Cl)C(Cl)(Cl)Cl
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| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 160929 | ChEMBL = 160929
| Gmelin = 26648
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C2Cl6/c3-1(4,5)2(6,7)8 | StdInChI = 1S/C2Cl6/c3-1(4,5)2(6,7)8
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VHHHONWQHHHLTI-UHFFFAOYSA-N | StdInChIKey = VHHHONWQHHHLTI-UHFFFAOYSA-N
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = <!-- blanked - oldvalue: C19248 --> | KEGG = C19248
| EC_number = 200-666-4
| CASNo = 67-72-1 | CASNo = 67-72-1
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>2</sub>Cl<sub>6</sub> | Formula = C<sub>2</sub>Cl<sub>6</sub>
| MolarMass = 236.74 g/mol | MolarMass = 236.74 g/mol
| BoilingPtC =183 to 185
| MeltingPt_notes = sublimes
| Density = 2.091 g/mL at 25&nbsp;°C
| Appearance = colorless crystals<ref name=PGCH/>
| Odor = camphor-like<ref name=PGCH/>
| Solubility = 0.005% (22.2&nbsp;°C)<ref name=PGCH/>
| VaporPressure = 0.2 mmHg (20&nbsp;°C)<ref name=PGCH/>
| MagSus = -112.7·10<sup>−6</sup> cm<sup>3</sup>/mol
}} }}
|Section3={{Chembox Hazards
| PEL = TWA 1 ppm (10 mg/m<sup>3</sup>) <ref name=PGCH>{{PGCH|0316}}</ref>
| IDLH = Ca <ref name=PGCH/>
| REL = Ca TWA 1 ppm (10 mg/m<sup>3</sup>) <ref name=PGCH/>
| FlashPt_notes = noncombustible<ref name=PGCH/>
| MainHazards = Probable ], dangerous CNS depressant
| NFPA-H = 2
| NFPA-F = 0
| NFPA-R = 0
| LD50 = 4460 mg/kg (rat, oral)<br/>4970 mg/kg (guinea pig, oral)
<ref>{{IDLH|67721|Hexachloroethane}}</ref>
}} }}
}}
'''Hexachloroethane''' ('''perchloroethane''') is an ] with the chemical formula {{chem2|(CCl3)2}}. It is a white or colorless solid at room temperature with a camphor-like odor.<ref name="Kirk-Othmer">{{cite book |last1=Snedecor |first1=Gayle |editor1-first= Jacqueline I. |editor1-last= Kroschwitz |title=Kirk-Othmer Concise Encyclopedia of Chemical Technology |edition=4th |year=1999 |publisher= John Wiley & Sons, Inc.|location=New York|isbn=978-0471419617|pages=428 |chapter=Hexachloroethane}}</ref> It has been used by the military in ]s, such as base-eject ] (]).

Hexachloroethane was discovered along with ] by ] in 1820. Faraday obtained it by chlorinating ].<ref>{{Cite book| author=Faraday, Michael | title = Experimental Researches in Chemistry and Physics | page = 46 | year = 1859 | publisher=Taylor and Francis | url = https://archive.org/details/experimentalrese00fararich| isbn = 978-0-85066-841-4}}</ref>

==Manufacture==
Chlorination of ] at 100–140&nbsp;°C with the presence of ] is the most commonly used commercial production method, however several other methods exist. A high purity form can be produced in a small scale by reacting chlorine together with ].<ref name=":0">{{Cite web|date=September 1997|title=Hexachloroethane 101|url=https://www.atsdr.cdc.gov/ToxProfiles/tp97.pdf}}</ref>{{Rp|101}} In September 1997, it was reported as no longer being produced in the United States for commercial distribution, but was produced as a by-product of industrial chlorination process.<ref name=":0" />{{Rp|101}}
:

==Applications==

Hexachloroethane has been used in the formulation of extreme pressure ]. It has also been used as a ] in the ] of propylene–tetrafluoroethylene copolymer. Hexachloroethane has been used as an ] in ] (under the tradename ''Avlothane''), a rubber accelerator, a component of fungicidal and insecticidal formulations as well as a moth repellant and a plasticizer for cellulose esters.<ref Name=Kirk-Othmer/>

Hexachloroethane has been used in the manufacture of degassing pellets to remove hydrogen gas bubbles from molten aluminum in aluminum foundries. This use, as well as similar uses in ], is being phased out in the ].<ref>ECHA, </ref>

===Use as smoke agent===
Smoke grenades, called hexachloroethane smoke or HC smoke, utilize a mixture containing roughly equal parts of hexachloroethane and ] and approximately 6% granular ]. These smokes are toxic, which is attributed to the production of ] ({{chem2|ZnCl2}}).<ref>{{cite web|url=http://www.dva.gov.au/aboutDVA/publications/health_research/SAS_Report/Documents/AppendixE.pdf |title=Appendix E: Smoke And Masking Agents |date=December 2003 |publisher=Australian Department of Veteran Affairs |page=E-3 |access-date=2012-10-04 |url-status=dead |archive-url=https://web.archive.org/web/20140213130143/http://www.dva.gov.au/aboutDVA/publications/health_research/SAS_Report/Documents/AppendixE.pdf |archive-date=2014-02-13 }}</ref><ref>National Research Council (1997). . Subcommittee on Military Smokes and Obscurants. Washington, DC: National Academy Press. p. 127</ref> According to Steinritz et al., "Due to its potential pulmonary toxicity," zinc chloride producing smoke grenades "have been discharged from the armory of most western countries (...)."<ref>Steinritz, D., Zehfuß, F., Stenger, B., Schmidt, A., Popp, T., Kehe, K., Mückter, H., Thiermann, H., Gudermann, T. (2018). Zinc chloride-induced TRPA1 activation does not contribute to toxicity in vitro. Toxicology Letters, 293, 133–139. doi:10.1016/j.toxlet.2017.09.008</ref>

=== Use as a riot control agent ===
Most documented uses of HC smoke as a riot control agent have occurred in the United States; its purchase towards that end has occurred in Milwaukee, Denver and Portland.<ref>{{Cite web|date=2021-02-21|title=Police deployed potentially lethal chemical during Black Lives Matter protests|url=https://www.salon.com/2021/02/21/police-deployed-potentially-lethal-chemical-during-black-lives-matter-protests_partner/|access-date=2021-06-16|website=Salon|language=en}}</ref>

] (FPS) and forces from the ] are believed to have used HC smoke grenades against protesters during various protests in 2020.<ref>{{Cite web|date=October 10, 2020|first=Sharon|last=Lerner|title=Toxic Chemical Smoke Grenades Used in Portland|url=https://theintercept.com/2020/10/10/portland-tear-gas-chemical-grenades-protests/|access-date=2021-06-16|website=The Intercept|language=en}}</ref> At the time, journalists photographed numerous smoke canisters labeled "HC", and measured unusually high levels of zinc and chloride in the area. However, FPS communications director Rob Sperling has denied the use of HC smoke, arguing that, of the two organizations, "FPS doesn't have any items that contain HC."<ref name=":1">{{Cite web|date=2020-10-20|title=Military-grade HC smoke used against Portland protesters|url=https://www.koin.com/news/protests/military-grade-hc-smoke-used-against-portland-protesters/|access-date=2021-06-16|website=KOIN.com|language=en-US}}</ref>

== Toxicity ==
Hexachloroethane is not particularly toxic when taken orally,<ref name=CDC>{{cite web |url= https://www.cdc.gov/niosh/idlh/67721.HTML |title= Documentation for Immediately Dangerous To Life or Health Concentrations (IDLHs) Hexachloroethane |date=May 1994 |publisher= NIOSH |access-date=2012-10-04}}</ref> but is considered to be quite toxic by skin adsorption. The primary effect is depression of the central nervous system.<ref Name=Kirk-Othmer/> The concentration that is ] is 300 ] and the ] according to the ] is 1 ] (skin).<ref name=CDC/> It is reasonably anticipated to be a carcinogen.<ref name="NIH">{{cite web|year=2011|title=Report on Carcinogens, Twelfth Edition, Hexachloroethane|url=https://ntp.niehs.nih.gov/ntp/roc/content/profiles/hexachloroethane.pdf|access-date=2012-10-04|publisher=NIH}}</ref>

==References==
{{reflist}}

==External links==
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* {{Webarchive|url=https://web.archive.org/web/20200805042347/http://www.scorecard.org/chemical-profiles/summary.tcl?edf_substance_id=67-72-1 |date=2020-08-05 }}
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{{Authority control}}{{Chlorides}}
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