| Revision as of 04:48, 17 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 456949256 of page Aliquat_336 for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 15:57, 5 April 2024 edit 38.27.127.42 (talk) →Solvent extraction of metalsTags: Mobile edit Mobile web edit |
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{{Chembox |
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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.}} |
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| verifiedrevid = 453454732 |
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| verifiedrevid = 477314600 |
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| Name = Aliquat 336 |
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| ImageFile = Aliquat 336.png |
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| Name = Aliquat 336 |
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| ImageFile = Aliquat 336.svg |
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| ImageSize = 200px |
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| ImageFile1 = Aliquat-336-3D-vdW.png |
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| ImageName = |
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| IUPACName = ''N''-Methyl-''N,N''-dioctyloctan-1-ammonium chloride |
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| ImageName = |
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| OtherNames = Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride |
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| IUPACName = ''N''-Methyl-''N,N,N''-trioctylammonium chloride |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride |
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| SMILES = CCCCCCCC(CCCCCCCC)(C)CCCCCCCC. |
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| SystematicName = |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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| SMILES = CCCCCCCC(CCCCCCCC)(C)CCCCCCCC. |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 19948 |
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| ChemSpiderID = 19948 |
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| PubChem = 21218 |
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| InChI = 1/C25H54N.ClH/c1-5-8-11-14-17-20-23-26(4,24-21-18-15-12-9-6-2)25-22-19-16-13-10-7-3;/h5-25H2,1-4H3;1H/q+1;/p-1 |
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| InChI = 1/C25H54N.ClH/c1-5-8-11-14-17-20-23-26(4,24-21-18-15-12-9-6-2)25-22-19-16-13-10-7-3;/h5-25H2,1-4H3;1H/q+1;/p-1 |
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| InChIKey = XKBGEWXEAPTVCK-REWHXWOFAD |
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| InChIKey = XKBGEWXEAPTVCK-REWHXWOFAD |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = XKBGEWXEAPTVCK-UHFFFAOYSA-M |
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| StdInChIKey = XKBGEWXEAPTVCK-UHFFFAOYSA-M |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| CASNo = <!-- blanked - oldvalue: 63393-96-4 --> |
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| RTECS = UZ2997500 |
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| UNII = YNE6ALT384 |
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| CASNo = 63393-96-4<!-- 5137-55-3 is for the pure trioctyl... chemical; Aliquat336 is a mixture with its own number --> |
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| RTECS = UZ2997500 |
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| Section2 = {{Chembox Properties |
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| Section2 = {{Chembox Properties |
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|C=25|H=54|Cl=1|N=1 |
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| C=25 | H=54 | Cl=1 | N=1 |
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| Appearance = Colorless viscous liquid |
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| Appearance = Colorless viscous liquid |
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| Density = 0.884 g/cm³ |
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| Density = 0.884 g/cm<sup>3</sup> |
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| Solubility = |
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| MeltingPtC = -20 |
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| MeltingPtC = −20 |
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| BoilingPtC = 225 |
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| BoilingPtC = 225 |
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| Viscosity = 1500 ] at 30 °C |
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| Viscosity = 1500 ] at 30 °C |
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| Section7 = {{Chembox Hazards |
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| MainHazards = Toxic (USA) |
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| EUClass = Harmful ('''Xn''') |
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| Section7 = {{Chembox Hazards |
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| FlashPt = 113 °C (closed cup) |
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| ExternalSDS = |
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| RPhrases = {{R22}} {{R38}} {{R41}} {{R50/53}} |
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| MainHazards = Toxic (USA) |
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| SPhrases = {{S26}} {{S39}} {{S60}} {{S61}} |
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| FlashPtC = 113 |
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| FlashPt_notes = (closed cup) |
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| GHSPictograms = {{GHS05}}{{GHS06}}{{GHS07}}{{GHS09}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|301|315|318|319|410}} |
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| PPhrases = {{P-phrases|264|270|273|280|301+310|302+352|305+351+338|310|321|330|332+313|337+313|362|391|405|501}} |
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| Section8 = {{Chembox Related |
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| OtherFunction = ], ], ], ] |
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'''Aliquat 336''' (Starks' catalyst) is a ] used as a ] and metal extraction reagent. It contains a mixture of C<sub>8</sub> (octyl) and C<sub>10</sub> (decyl) chains with C<sub>8</sub> predominating. It is an ].<ref>{{Cite journal | doi = 10.1080/01932691.2013.862170| title = Physicochemical Properties of an Hydrophobic Ionic Liquid (Aliquat 336) in a Polar Protic Solvent (Formamide) at Different Temperatures| journal = Journal of Dispersion Science and Technology| volume = 36| issue = 5| pages = 641| year = 2015| last1 = Litaiem| first1 = Yousra| last2 = Dhahbi| first2 = Mahmoud| s2cid = 95868263}}</ref> |
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==Applications== |
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===Organic Chemistry=== |
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Aliquat 336 is used as a phase transfer catalyst,<ref>{{cite journal | doi = 10.1021/ja00730a033 | author = C. M. Starks | title = Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts | journal = J. Am. Chem. Soc. | year = 1971 | volume = 93 | pages = 195–199}}</ref> including in the catalytic oxidation of ] to ].<ref>{{cite journal | author = S. M. Reed | author2=J. E. Hutchison | title = An Environmentally Benign Synthesis of Adipic Acid | journal = ] | year = 2000 | volume = 77 | pages = 1627–8 | doi = 10.1021/ed077p1627 | issue = 12}}</ref> This reaction is an example of ], as it is more environmentally friendly than the traditional method of oxidizing ] or ] with ] or ], which produce hazardous wastes.<ref>{{cite book|url=https://books.google.com/books?id=HokcDQAAQBAJ&dq=green+aliquat++cyclohexene&pg=PA76|title=Green Chemistry: Fundamentals and Applications|isbn=9781466578265|last1=Ameta|first1=Suresh C|last2=Ameta|first2=Rakshit|date=2013-09-11|publisher=CRC Press }}</ref> |
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Aliquat 336 was used in the total synthesis of ] by Darren Dixon.<ref>{{cite journal |title=Total Synthesis of Manzamine A and Related Alkaloids| first1=Pavol |last1=Jakubec |first2=Alison |last2=Hawkins |first3=Wolfgang |last3=Felzmann |first4=Darren J. |last4=Dixon | journal = ] | year = 2012 | volume = 134 |issue=42| pages = 17482–17485 | doi = 10.1021/ja308826x | pmid=23039372 }}</ref> |
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===Solvent extraction of metals=== |
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{{Main|Liquid–liquid extraction}} |
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Aliquat 336 has been used for the extraction of metals by acting as a liquid ]. It is commonly used as a solution in hydrocarbon solvents such as aromatic ]. Aliphatic kerosene can also be used, but requires the addition of a phase modifier (typically a long chain alcohol) to prevent the formation of third phase. |
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=== Waste treatment === |
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Several applications have been successfully carried out with Aliquat 336, such as the recovery of acids or ], or the removal of certain metals from ]. In addition, foaming has also been controlled by using this agent during the treatment of wastewater containing ] surfactants. |
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==References== |
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<references/> |
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