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Sulfolane information


Sulfolane
Sulfolane
Ball-and-stick model of the sulfolane molecule
  Carbon, C
  Hydrogen, H
  Oxygen, O
  Sulfur, S
Names
Preferred IUPAC name
6-Thiolane-1,1-dione
Other names
  • Sulfolane
  • Tetrahydrothiophene 1,1-dioxide
  • Tetramethylene sulfone
Identifiers
CAS Number
  • 126-33-0 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:74794 ☒N
ChEMBL
  • ChEMBL3186899
ChemSpider
  • 29080 checkY
ECHA InfoCard 100.004.349 Edit this at Wikidata
EC Number
  • 204-783-1
PubChem CID
  • 31347
RTECS number
  • XN0700000
UNII
  • Y5L06AH4G5 checkY
UN number 3334
CompTox Dashboard (EPA)
  • DTXSID3027037 Edit this at Wikidata
InChI
  • InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2 checkY
    Key: HXJUTPCZVOIRIF-UHFFFAOYSA-N checkY
  • InChI=1/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
    Key: HXJUTPCZVOIRIF-UHFFFAOYAA
SMILES
  • C1CCS(=O)(=O)C1
Properties
Chemical formula
(CH2)4SO2
Molar mass 120.17 g·mol−1
Appearance Colorless liquid
Density 1.261 g/cm3, liquid
Melting point 27.5 °C (81.5 °F; 300.6 K)
Boiling point 285 °C (545 °F; 558 K)
Solubility in water
miscible
Viscosity 0.01007 Pa·s at 25 °C
Structure
Dipole moment
4.35 D
Hazards
GHS labelling:
Pictograms
GHS07: Exclamation mark
Signal word
Warning
Hazard statements
H302
Precautionary statements
P264, P270, P301+P312, P330, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Flash point 165 °C (329 °F; 438 K)
Autoignition
temperature
528 °C (982 °F; 801 K)
Related compounds
Related compounds
  • Methylsulfonylmethane
  • Tetrahydrothiophene
  • Sulfolene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Sulfolane (also tetramethylene sulfone, systematic name: 6-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula (CH2)4SO2. It is a colorless liquid commonly used in the chemical industry as a solvent for extractive distillation and chemical reactions. Sulfolane was originally developed by the Shell Oil Company in the 1960s as a solvent to purify butadiene.[1][2] Sulfolane is a polar aprotic solvent, and it is miscible with water.

  1. ^ Young, Eldred E. (Shell International Research) BE Patent 616856, 1962
  2. ^ Goodenbour, John W.; Carlson, George J. (Shell International Research) BE Patent 611850, 1962

and 25 Related for: Sulfolane information

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Sulfolane

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Sulfolane (also tetramethylene sulfone, systematic name: 1λ6-thiolane-1,1-dione) is an organosulfur compound, formally a cyclic sulfone, with the formula...

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Sulfone

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cycloaddition reactions with dienes. The industrially useful solvent sulfolane is prepared by addition of sulfur dioxide to buta-1,3-diene followed by...

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Tetrahydrothiophene

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Oxidation of THT gives the sulfone sulfolane, which is of interest as a polar, odorless solvent: C4H8S + 2 O → C4H8SO2 Sulfolane is, however, more conventionally...

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Water

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propanol, isopropanol, acetone, glycerol, 1,4-dioxane, tetrahydrofuran, sulfolane, acetaldehyde, dimethylformamide, dimethoxyethane, dimethyl sulfoxide...

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Sodium chloride

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30.2 Methanol 14 Ethanol 0.65 Dimethylformamide 0.4 Propan-1-ol 0.124 Sulfolane 0.05 Butan-1-ol 0.05 Propan-2-ol 0.03 Pentan-1-ol 0.018 Acetonitrile 0...

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Benzene

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with any one of a number of solvents, including diethylene glycol or sulfolane, and benzene is then separated from the other aromatics by distillation...

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Indian Institute of Petroleum

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through nmp 2000. Propane deasphalting 1999. Visbreaking technology 1998. Sulfolane production technology 1997. Business development and technology marketing...

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Potassium chloride

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Liquid sulfur dioxide 0.41 Methanol 5.3 Ethanol 0.37 Formic acid 192 Sulfolane 0.04 Acetonitrile 0.024 Acetone 0.00091 Formamide 62 Acetamide 24.5 Dimethylformamide...

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Halex process

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fluoride. Typical solvents are dimethylsulfoxide, dimethylformamide, and sulfolane. Potassium chloride is generated in the process. The reaction is mainly...

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Polar aprotic solvent

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C5H5N 115 °C 13.3 0.982 g/cm3 2.22 reacts with protic and Lewis acids sulfolane C4H8SO2 286 °C ? 1.27 g/cm3 4.8 high boiling point tetrahydrofuran C4H8O...

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Properties of water

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propanol, isopropanol, acetone, glycerol, 1,4-dioxane, tetrahydrofuran, sulfolane, acetaldehyde, dimethylformamide, dimethoxyethane, dimethyl sulfoxide...

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Sulfur

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sulfoxide, dimethyl sulfoxide, is a common solvent; a common sulfone is sulfolane. Sulfonic acids are used in many detergents. Compounds with carbon–sulfur...

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Raney nickel

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hexamethylenediamine; Olefins to paraffins, for example, sulfolene to sulfolane; Acetylenes to paraffins, for example, 1,4-butynediol to 1,4-butanediol...

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Methylsulfonylmethane

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Related compounds Related compounds DMSO dimethyl sulfide dimethyl sulfate sulfolane Except where otherwise noted, data are given for materials in their standard...

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Sulfur dioxide

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This reaction is exploited on an industrial scale for the synthesis of sulfolane, which is an important solvent in the petrochemical industry. Sulfur dioxide...

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Kerosene

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hydrocarbons. A common method is solvent extraction with methanol, DMSO or sulfolane. Aromatic kerosene is a grade of kerosene with a large concentration of...

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Benzylamine

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with nitronium tetrafluoroborate and nitrosonium tetrafluoroborate in sulfolane to produce HNIW. The hydrochloride salt of benzylamine, C6H5CH2NH3Cl or...

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Trifluoroperacetic acid

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162 °C. It is soluble in acetonitrile, dichloromethane, diethyl ether, and sulfolane, and readily reacts with water. Like all peroxy acids, it is potentially...

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Butadiene

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process is called hydrocyanation. Butadiene is used to make the solvent sulfolane. Butadiene is also useful in the synthesis of cycloalkanes and cycloalkenes...

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Sulfur compounds

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sulfoxide, dimethyl sulfoxide, is a common solvent; a common sulfone is sulfolane. Sulfonic acids are used in many detergents. Compounds with carbon–sulfur...

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Fast atom bombardment

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3-nitrobenzyl alcohol (3-NBA), 18-crown-6 ether, 2-nitrophenyloctyl ether, sulfolane, diethanolamine, and triethanolamine. This technique is similar to secondary...

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Claisen rearrangement

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ethanol/water solvent mixtures give rate constants 10-fold higher than sulfolane. Trivalent organoaluminium reagents, such as trimethylaluminium, have...

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Girolami method

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(2×2)+(8×1)+(2×2)=16 Two primary amine groups = 120% d=1.2×60/5×16=0.90 0.899 Sulfolane 120 (4×2)+(8×1)+(2×2)+(1×4)=24 One ring and two S=O bonds = 130% d=1.3×120/5×24=1...

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Wacker process

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ISSN 0022-3263. Fahey, Darryl R.; Zeuch, Ernest A. (November 1974). "Aqueous sulfolane as solvent for rapid oxidation of higher .alpha.-olefins to ketones using...

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Ethylene oxide

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adding a catalyst, such as platinum, platinum-palladium, or iodine with sulfolane. 2-methyl-1,3-dioxolane is formed as a side product in the last case....

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