| Revision as of 18:16, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,071 edits Saving copy of the {{chembox}} taken from revid 465661750 of page Sulfolane for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 22:17, 17 April 2024 edit Bernardirfan (talk | contribs)Extended confirmed users10,991 edits Extra white spaces, Replacing HTML with {{ubl}} |
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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 = 444126315 |
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|verifiedrevid = 470473749 |
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| Name = Sulfolane |
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| ImageFileL1 = Sulfolane-2D-skeletal.png |
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|Name = Sulfolane |
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|ImageFile1 = Sulfolane-2D-skeletal.png |
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| ImageSizeL1 = 80px |
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|ImageSize1 = 120px |
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| ImageNamL1e = Sulfolane |
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| ImageFileR1 = Sulfolane-3D-balls.png |
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|ImageName1 = Sulfolane |
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|ImageFile2 = Sulfolane-3D-balls.png |
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| ImageSizeR1 = 120px |
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| ImageNameR1 = Ball-and-stick model of the sulfolane molecule |
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|ImageName2 = Ball-and-stick model of the sulfolane molecule |
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|ImageCaption2 = {{legend|black|], C}}{{legend|white|], H}}{{legend|red|], O}}{{legend|yellow|], S}} |
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| IUPACName = Tetrahydrothiophene 1,1-dioxide |
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|PIN = 1λ<sup>6</sup>-Thiolane-1,1-dione |
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| OtherNames = sulfolane<br />tetramethylene sulfone |
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|OtherNames = {{ubl|Sulfolane|Tetrahydrothiophene 1,1-dioxide|Tetramethylene sulfone}} |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|CASNo_Ref = {{cascite|changed|CAS}} |
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| UNII = Y5L06AH4G5 |
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|CASNo = 126-33-0 |
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| SMILES = C1CCS(=O)(=O)C1 |
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|ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChEBI = 74794 |
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| ChemSpiderID = 29080 |
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| PubChem = 31347 |
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|ChEMBL = 3186899 |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChI = 1/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2 |
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|ChemSpiderID = 29080 |
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| InChIKey = HXJUTPCZVOIRIF-UHFFFAOYAA |
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|EC_number = 204-783-1 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|PubChem = 31347 |
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| StdInChI = 1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2 |
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|RTECS = XN0700000 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|UNNumber = 3334 |
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| StdInChIKey = HXJUTPCZVOIRIF-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = Y5L06AH4G5 |
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| CASNo = <!-- blanked - oldvalue: {{{CAS|126-33-0}}} --> |
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|SMILES = C1CCS(=O)(=O)C1 |
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|126-33-0}}} |
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|InChI = 1/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2 |
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}} |
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|InChIKey = HXJUTPCZVOIRIF-UHFFFAOYAA |
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| Section2 = {{Chembox Properties |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| Formula = C<sub>4</sub>H<sub>8</sub>O<sub>2</sub>S |
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|StdInChI = 1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2 |
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| MolarMass = 120.17 g/mol |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| Appearance = clear colorless liquid |
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|StdInChIKey = HXJUTPCZVOIRIF-UHFFFAOYSA-N |
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| Density = 1.261 g/cm<sup>3</sup>, liquid |
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| Solubility = fully soluble |
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| MeltingPt = 27.5 °C |
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| BoilingPt = 285 °C |
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| Viscosity = 0.01007 ] at 25 °C<!-- Liquids only, omit if data unavailable. You may use if you prefer --> |
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| Section3 = {{Chembox Structure |
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| Dipole = 4.35 ] |
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| Section7 = {{Chembox Hazards |
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| Autoignition = 528 °C |
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| ExternalMSDS = |
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| NFPA-H = 2 |
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| NFPA-F = 1 |
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| NFPA-R = |
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| FlashPt = 165 °C |
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| RPhrases = {{R22}} |
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| SPhrases = {{S23}}, {{S24}}, {{S25}} |
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|Section2={{Chembox Properties |
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|Formula = {{chem2|(CH2)4SO2}} |
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|C=4|H=8|O=2|S=1 |
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|Appearance = Colorless liquid |
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|Density = 1.261 g/cm<sup>3</sup>, liquid |
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|Solubility = miscible |
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|MeltingPtC = 27.5 |
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|BoilingPtC = 285 |
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|Viscosity = 0.01007 ] at 25 °C<!-- Liquids only, omit if data unavailable. You may use if you prefer --> |
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|Section3={{Chembox Structure |
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|Dipole = 4.35 ] |
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|Section4={{Chembox Hazards |
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|NFPA-H = 2 |
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|NFPA-F = 1 |
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|NFPA-I = 0 |
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|AutoignitionPtC = 528 |
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|FlashPtC = 165 |
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|GHSPictograms = {{GHS07}} |
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|GHSSignalWord = Warning |
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|HPhrases = {{H-phrases|302}} |
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|PPhrases = {{P-phrases|264|270|301+312|330|501}} |
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|Section5={{Chembox Related |
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|OtherCompounds = {{ubl|]|]|]}} |
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'''Sulfolane''' (also '''tetramethylene sulfone''', ]: '''1λ<sup>6</sup>-thiolane-1,1-dione''') is an ], formally a cyclic ], with the formula {{chem2|(CH2)4SO2|auto=1}}. It is a colorless ] commonly used in the chemical industry as a ] for extractive distillation and chemical reactions. Sulfolane was originally developed by the ] in the 1960s as a solvent to purify ].<ref>Young, Eldred E. (Shell International Research) BE Patent 616856, 1962</ref><ref>Goodenbour, John W.; Carlson, George J. (Shell International Research) BE Patent 611850, 1962</ref> Sulfolane is a ], and it is miscible with water. |
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==Properties== |
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Sulfolane is classified as a ], a group of organosulfur compounds containing a sulfonyl ]. The sulfone group is a ] atom doubly bonded to two ] atoms and singly bonded to two carbon centers. The sulfur-oxygen double bond is polar, conferring good solubility in water, while the four carbon ring provides ] stability. These properties allow it to be miscible in both water and ]s, resulting in its widespread use as a solvent for purifying hydrocarbon mixtures. |
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==Synthesis== |
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The original method developed by the ] was to first allow butadiene to react with ] via a ] to give ]. This was then ] using ] as a catalyst to give sulfolane.<ref name=Ullmann>Hillis O. Folkins, "Benzene" in ''Ullmann’s Encyclopedia of Industrial Chemistry'', Wiley-VCH, Weinheim, 2005. {{doi|10.1002/14356007.a03_475}}</ref><ref>Earl Clark, ''Kirk-Othmer Encyclopedia of Chemical Technology'', "Sulfolane and Sulfones", John Wiley & Sons, NY, 1997</ref> |
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Shortly thereafter, it was discovered that both the product yield and the lifetime of the ] could be improved by adding ] and then ] to a ] of roughly 5-8 before hydrogenation. Developments have continued over the years, including in the catalysts used. Recently, it was found that Ni-B/MgO showed superior catalytic activity to that of Raney nickel and other common catalysts that have been used in the hydrogenation of sulfolene. |
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Other syntheses have also been developed, such as oxidizing ] with hydrogen peroxide. This reaction produces tetramethylene sulfoxide, which can then be further oxidized. Because the first ] occurs at low temperature and the second at higher temperature, the reaction can be controlled at each stage. This gives greater freedom for the manipulation of the reaction, which can potentially lead to higher yields and purity. |
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==Uses== |
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Sulfolane is widely used as an industrial ], especially in the extraction of ] hydrocarbons from hydrocarbon mixtures and to purify ].<ref name=Ullmann/> The first large scale commercial use of sulfolane, the sulfinol process, was first implemented by ] in March 1964 at the Person gas plant near Karnes City, Texas. The sulfinol process purifies natural gas by removing {{chem2|], ], ]}} and mercaptans from natural gas with a mixture of ] and sulfolane. |
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Shortly after the sulfinol process was implemented, sulfolane was found to be highly effective in separating high purity aromatic compounds from hydrocarbon mixtures using ]. This process is widely used in ] and the ]. Because sulfolane is one of the most efficient industrial solvents for purifying aromatics, the process operates at a relatively low solvent-to-feed ratio, making sulfolane relatively cost effective compared to similar-purpose solvents. In addition, it is selective in a range that complements ]; where sulfolane cannot separate two compounds, distillation easily can and vice versa, keeping sulfolane units useful for a wide range of compounds with minimal additional cost. |
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Whereas sulfolane is highly stable and can therefore be reused many times, it does eventually degrade into ] byproducts. A number of measures have been developed to remove these byproducts, allowing the sulfolane to be reused and increase the lifetime of a given supply. Some methods that have been developed to regenerate spent sulfolane include vacuum and steam distillation, back extraction, adsorption, and anion-cation exchange resin columns. |
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Sulfolane is also added to hydrofluoric acid as a vapor suppressant,<ref>{{Cite web|url=http://www.cpchem.com/bl/specchem/en-us/tdslibrary/FactSheet%20Sulfolane.pdf|title=Sulfolane Fact Sheet|website=Chevron Phillips Chemical Company}}</ref> commonly for use in a refinery's ]. This "modified" hydrofluoric acid is less prone to vaporization if released in its liquid form. |
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== As a pollutant == |
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Groundwater in parts of the city of ], has been contaminated with sulfolane due to pollution from a now-closed petroleum refinery.<ref name=":0">{{Cite web|title=Human Health and Toxicology - Sulfolane and PFAS|url=https://dec.alaska.gov/spar/csp/sites/north-pole-refinery/health/|access-date=2020-10-23|website=dec.alaska.gov}}</ref> Due to this contamination, affected residents have been supplied with alternative potable water sources.<ref name=":0" /> Animal studies on the toxicity of sulfolane are ongoing, funded through the US federal government's ].<ref>{{Cite web|date=|title=Sulfolane|url=https://ntp.niehs.nih.gov/whatwestudy/topics/sulfolane/index.html|archive-url=|archive-date=|access-date=2020-10-23|website=National Toxicology Program: U.S. Department of Health and Human Services}}</ref> No long-term ''in vivio'' animal studies have been done, which prevents any firm conclusion as to whether sulfolane is a carcinogen, although ''in vitro'' studies have failed to demonstrate any cancerous changes in bacterial or animal cells. In animal studies, high doses of sulfolane have induced negative impacts on the central nervous system, including hyperactivity, convulsions and hypothermia; the impacts of lower doses, especially over the long-term, are still being studied.<ref>{{Cite web|date=November 2019|title=Sulfolane: Research Efforts by the National Toxicology Program|url=https://dec.alaska.gov/media/21202/ntp-sulfolane-fact-sheet-11-19.pdf|archive-url=|archive-date=|access-date=2020-10-23|website=Alaska Department of Environmental Conservation}}</ref> |
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==See also== |
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*] |
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==References== |
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{{more footnotes|date=November 2019}} |
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{{reflist}} |
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*Ge, Shaohui; Wu, Zhijie; Zhang, Minghui; Li, Wei; Tao, Keyi.''Industrial & Engineering Chemistry Research'','''2006'''''45(7)'', 2229-2234, |
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*Sharipov, A. Kh.''Russian Journal of Applied Chemistry'''''2003''',''76(1)'', 108-113. |
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*Dunn, C. L.; Freitas, E. R.; Hill, E. S.; Sheeler, J. E. R., Jr. Proc., Ann. Conv. Nat. Gas Processors Assoc. Am.,''Tech. Papers'''''1965''',''44'' 55-8 |
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*Broughton, Donald B.; Asselin, George F. UOP Process Div., Universal Oil Prod. Co., Des Plaines, IL, USA. World Petrol. Congr., Proc., 7th'''1968''', Meeting Date 1967,''4'' 65-73. Publisher: Elsevier Publ. Co. Ltd., Barking, Engl |
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*Lal, Raj Kumar Jagadamba; Bhat, Sodankoor Garadi Thirumaleshwara. (Indian Petrochemicals Corp. Ltd., India). Eur. Pat. Appl. 1989-308019 (1991) |
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*Van der Wiel, A.''Nature'''''1960''',''187'' 142-3. |
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*Block, E.''Reactions of Organosulfur Compounds''; Academic: New York, 1978 |
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*Belen'kii, L.I.''Chemistry of Organosulfur Compounds''; Horwood: New York, 1990 |
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==External links== |
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* Calculation of , , , of sulfolane |
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