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Revision as of 13:58, 10 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'ChEBI_Ref') per   Latest revision as of 16:15, 31 August 2022 edit Smokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,728 edits sodium analogue 
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{{chembox {{chembox
| Watchedfields = changed
| verifiedrevid = 444060996 | verifiedrevid = 444062584
| Name = Potassium ethyl xanthate | Name = Potassium amyl xanthate
| ImageFile = Potassium_ethyl_xanthate.png
| ImageFile = Potassium amyl xanthate.svg
| ImageSize =
| ImageName = | ImageSize = 200px
| IUPACName = potassium ''O''-ethylcarbonodithioate | PIN = Potassium ''O''-pentyl carbonodithioate
| OtherNames = potassium ethylxanthogenate<br/> | OtherNames = potassium pentylxanthogenate<br/>
potassium-''O''-ethyl dithiocarbonate potassium-''O''-pentyl dithiocarbonate
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = 140-89-6 | CASNo = 2720-73-2
| CASNo_Ref = | CASNo_Ref = {{cascite|correct|CAS}}
| CASOther = | CASNoOther =
| MeSHName = | MeSHName =
| PubChem = 2735045 | PubChem = 493949
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 8491 | ChemSpiderID = 16668
| EC_number = 220-329-5
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| ChEMBL = 2380741
| StdInChI = 1S/C3H6OS2.K/c1-2-4-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| SMILES = .C(=S)OCC
| InChI = 1S/C3H6OS2.K/c1-2-4-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1 | StdInChI = 1S/C6H12OS2.K/c1-2-3-4-5-7-6(8)9;/h2-5H2,1H3,(H,8,9);/q;+1/p-1
| SMILES = CCCCCOC(=S).
| InChI = 1S/C6H12OS2.K/c1-2-3-4-5-7-6(8)9;/h2-5H2,1H3,(H,8,9);/q;+1/p-1
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JCBJVAJGLKENNC-UHFFFAOYSA-M | StdInChIKey = YIBBMDDEXKBIAM-UHFFFAOYSA-M
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=3|H=5|O=1|S=2|Na=1 | C=6 | H=11 | O=1 | S=2 | K=1
| Appearance = Pale yellow or yellow powder
| ExactMass =
| Density = 1.073 g/cm3
| Appearance = Pale yellow powder
| MeltingPtC =
| Density = 1.263 g/cm<sup>3</sup><ref name=r5p5>Report 5 (1995) p. 5</ref>
| MeltingPt_notes =
| MeltingPt = 225 – 226 °C
| BoilingPtC =
| BoilingPt = decomposes
| Solubility = | Solubility = Soluble
| pKa = approximately 1.6 | pKa =
| pKb = }} | pKb = }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = | AutoignitionPt =
| RPhrases = {{R15}} {{R21}} {{R22}} {{R29}} {{R36}} {{R38}} | GHSPictograms = {{GHS02}}{{GHS07}}{{GHS09}}
| GHSSignalWord = Warning
| SPhrases = {{S3}} {{S9}} {{S35}} {{S36}} {{S37}} {{S38}} {{S39}} {{S16}} {{S23}} {{S51}}
| HPhrases = {{H-phrases|228|302|312|315|319|335|411 }}
| PPhrases = {{P-phrases|210|240|241|261|264|270|271|273|280|301+312|302+352|304+340|305+351+338|312|321|322|330|332+313|337+313|362|363|370+378|391|403+233|405|501}}
}} }}
}} }}


'''Potassium ethyl xanthate''' is an ] with the chemical formula CH<sub>3</sub>CH<sub>2</sub>OCS<sub>2</sub>K. It is a pale yellow powder that is used in the mining industry for the separation of ]s. Unlike the related ], the potassium salt exists as an ] salt<!--, which is more convenient?-->. '''Potassium amyl xanthate''' (/pəˈtæsiəm ˌæmɪl ˈzænθeɪt/) is an ] with the chemical formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>OCS<sub>2</sub>K. It is a pale yellow powder with a pungent odor that is soluble in water. It is widely used in the mining industry for the separation of ]s using the ].


==Production and properties== ==Production and properties==
Xanthate saltss are prepared by the action of alcohols on carbon disulfide. The alkoxide is generated in situ from potassium hydroxide:<ref>This report gives a detailed procedure {{OrgSynth|author=Charles C. Price and Gardner W. Stacy|year=1948|title=p-nitrophenyl) sulfide As typical for ]s, potassium amyl xanthate is prepared by reacting ''n''-] with ] and ].<ref>{{OrgSynth |author=Charles C. Price and Gardner W. Stacy|year=1948|title=p-nitrophenyl sulfide |volume =28 |pages=82 |collvol=3 |collvolpages=667 |prep=CV3P0667}}</ref>
: CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>OH + CS<sub>2</sub> + KOH → CH<sub>3</sub>(CH<sub>2</sub>)<sub>4</sub>OCS<sub>2</sub>K + H<sub>2</sub>O
|volume=28|pages=82|collvol=3|collvolpages=667|prep=CV3P0667}}</ref>
:CH<sub>3</sub>CH<sub>2</sub>OH + CS<sub>2</sub> + KOH → CH<sub>3</sub>CH<sub>2</sub>OCS<sub>2</sub>K + H<sub>2</sub>O


Potassium ethyl xanthate is a pale yellow powder that is relatively stable at high pH but rapidly hydrolyses at pH <9 at 25 °C. Unlike the sodium derivative, potassium xanthate crystallizes as the anhydrous salt and is nonhygroscopic. Potassium amyl xanthate is a pale yellow powder. Its solutions are relatively stable between pH 8 and 13 with a maximum of stability at pH 10.<ref> J. Dyer, L. H. Phifer, Macromolecules 2 (1969) 111. R. J. Millican, C. K. Sauers, J. Org. Chem. '''44''' (1979) 1964.</ref>

==Applications==
==Related compounds==
Potassium ethyl xanthate is predominantly used in the mining industry as ] for extraction of the ores of copper, nickel, and silver.<ref name=Ullmann/> The method exploits the affinity of these ] metals for the organosulfur ligand.
*Sodium amyl xanthate is used in the separation of nickel and copper from their ores.<ref>{{Ullmann|author=Kerfoot, Derek G. E. |title=Nickel|doi=10.1002/14356007.a17_157|year=2005}}</ref>
Potassium xanthate is a useful ] for preparing xanthate esters from alkyl and aryl halides. The resulting xanthate estes are useful intermediates in ].<ref>One of several procedures using xanthate esters: {{OrgSynth|author=Fabien Gagosz and Samir Z. Zard|year=1948|title=A Xanthate-Transfer Approach to α-Trifluoromethylamines |volume=84|pages=32|collvol=11|collvolpages=212|prep=V84P0032}}</ref>


==Safety== ==Safety==
Xanthates are poisonous because they release carbon disulfide. The ] is 683 mg/kg (oral, rats) for potassium ethyl xanthate.<ref name=Ullmann>Kathrin-Maria Roy "Xanthates" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a28 423}}</ref> The {{LD50}} is 90-148 mg/kg (oral, rat). <ref name=Ullmann>Kathrin-Maria Roy "Xanthates" in Ullmann's Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim.</ref>

It is a biodegradable compound.


==References== ==References==
{{reflist|2}} {{reflist}}


] ]
] ]
]
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