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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 |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 444060996 |
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| verifiedrevid = 444062584 |
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| Name = Potassium ethyl xanthate |
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| Name = Potassium amyl xanthate |
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| ImageFile = Potassium_ethyl_xanthate.png |
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| ImageFile = Potassium amyl xanthate.svg |
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| ImageSize = |
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| ImageName = |
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| ImageSize = 200px |
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| IUPACName = potassium ''O''-ethylcarbonodithioate |
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| PIN = Potassium ''O''-pentyl carbonodithioate |
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| OtherNames = potassium ethylxanthogenate<br/> |
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| OtherNames = potassium pentylxanthogenate<br/> |
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potassium-''O''-ethyl dithiocarbonate |
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potassium-''O''-pentyl dithiocarbonate |
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|Section1= {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = 140-89-6 |
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| CASNo = 2720-73-2 |
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| CASNo_Ref = |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASOther = |
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| CASNoOther = |
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| MeSHName = |
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| MeSHName = |
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| PubChem = 2735045 |
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| PubChem = 493949 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8491 |
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| ChemSpiderID = 16668 |
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| EC_number = 220-329-5 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL = 2380741 |
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| StdInChI = 1S/C3H6OS2.K/c1-2-4-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| SMILES = .C(=S)OCC |
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| InChI = 1S/C3H6OS2.K/c1-2-4-3(5)6;/h2H2,1H3,(H,5,6);/q;+1/p-1 |
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| StdInChI = 1S/C6H12OS2.K/c1-2-3-4-5-7-6(8)9;/h2-5H2,1H3,(H,8,9);/q;+1/p-1 |
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| SMILES = CCCCCOC(=S). |
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| InChI = 1S/C6H12OS2.K/c1-2-3-4-5-7-6(8)9;/h2-5H2,1H3,(H,8,9);/q;+1/p-1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = JCBJVAJGLKENNC-UHFFFAOYSA-M |
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| StdInChIKey = YIBBMDDEXKBIAM-UHFFFAOYSA-M |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=3|H=5|O=1|S=2|Na=1 |
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| C=6 | H=11 | O=1 | S=2 | K=1 |
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| Appearance = Pale yellow or yellow powder |
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| ExactMass = |
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| Density = 1.073 g/cm3 |
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| Appearance = Pale yellow powder |
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| MeltingPtC = |
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| Density = 1.263 g/cm<sup>3</sup><ref name=r5p5>Report 5 (1995) p. 5</ref> |
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| MeltingPt_notes = |
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| MeltingPt = 225 – 226 °C |
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| BoilingPtC = |
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| BoilingPt = decomposes |
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| Solubility = |
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| Solubility = Soluble |
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| pKa = approximately 1.6 |
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| pKa = |
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| pKb = }} |
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| pKb = }} |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| FlashPt = |
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| Autoignition = |
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| AutoignitionPt = |
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| RPhrases = {{R15}} {{R21}} {{R22}} {{R29}} {{R36}} {{R38}} |
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| GHSPictograms = {{GHS02}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Warning |
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| SPhrases = {{S3}} {{S9}} {{S35}} {{S36}} {{S37}} {{S38}} {{S39}} {{S16}} {{S23}} {{S51}} |
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| HPhrases = {{H-phrases|228|302|312|315|319|335|411 }} |
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| 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}} |
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'''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?-->. |
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'''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 ]. |
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==Production and properties== |
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==Production and properties== |
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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 |
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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> |
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: 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 |
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|volume=28|pages=82|collvol=3|collvolpages=667|prep=CV3P0667}}</ref> |
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: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 |
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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. |
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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> |
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==Applications== |
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==Related compounds== |
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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. |
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*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> |
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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> |
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==Safety== |
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==Safety== |
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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> |
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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> |
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It is a biodegradable compound. |
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==References== |
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==References== |
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{{reflist|2}} |
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