Sulfolane



Sulfolane
General
Systematic name Tetrahydrothiophene 1,1-dioxide
Other names sulfolane
tetramethylene sulfone
Molecular formula C4H8O2S
SMILES O=S1(CCCC1)=O
Molar mass 120.17 g/mol
Appearance clear colorless liquid
CAS number 126-33-0
Properties
Density and phase 1.261 g/cm3, liquid
water fully soluble
Melting point 27.5 °C
Boiling point 285 °C
Autoignition temperature 528 °C
Viscosity 0.01007 Pa·s at 25°C
Structure
Symmetry group D26h
Dipole moment 4.35 D
Hazards
MSDS External MSDS
NFPA 704
1
2
0
 
Flash point 165 °C
R/S statement S25
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Infobox disclaimer and references

Sulfolane (also tetramethylene sulfone, butadiene. Sulfolane is an aprotic organosulfur compound, and it is readily soluble in water.

Chemical Properties

Sulfolane is classified as a hydrocarbon mixtures.

Synthesis

The original method developed by the Raney nickel as a catalyst to give sulfolane.


Shortly thereafter, it was discovered that both the product yield and the lifetime of the hydrogenation.

Developments have continued over the years, including in the hydrogenation of sulfolene.

Other syntheses have also been developed, such as oxidizing oxidation takes place at low temperature and the second at relatively 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.

Uses

Sulfolane is widely used as an industrial hydrocarbon mixtures and to purify natural gas.

The first large scale commercial use of sulfolane, the sulfinol process, was first implemented by Shell Oil Company in March of 1964 at the Person gas plant near Karnes City, Texas. The sulfinol process purifies natural gas by removing H2S, CO2, COS and mercaptans from natural gas with a mixture of alkanolamine and sulfolane.

Shortly after the sulfinol process was implemented, sulfolane was found to be highly effective in separating high purity aromatics, they operate at the lowest solvent-to-feed ratio, making sulfolane units highly cost effective. In addition, it is selective in a range that complements distilliation; where sulfolane can’t separate two compounds, distillation easily can and vice versa, keeping sulfolane units useful for a wide range of compounds with minimal additional cost.

While sulfolane is highly stable and can therefore be reused many times, it does eventually break down into acidic 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.

See also

References

  • UOP Document: Sulfolane Process
  • RohMax.com: Sulfolane, a specialty solvent
  • ChemicalLand21.com: Sulfolane Industrial Chemical Data
  • ChemIndustry.com search: Sulfolane
  • Young, Eldred E. (Shell International Research) BE Patent 616856, 1962
  • Goodenbour, John W.; Carlson, George J. (Shell International Research) BE Patent 611850, 1962
  • Ge, Shaohui; Wu, Zhijie; Zhang, Minghui; Li, Wei; Tao, Keyi. Industrial & Engineering Chemistry Research, 2006 45(7), 2229-2234,
  • Sharipov, A. Kh. Russian Journal of Applied Chemistry 2003, 76(1), 108-113.
  • 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
  • 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
  • Lal, Raj Kumar Jagadamba; Bhat, Sodankoor Garadi Thirumaleshwara. (Indian Petrochemicals Corp. Ltd., India). Eur. Pat. Appl. 1989-308019 (1991)
  • Van der Wiel, A. Nature 1960, 187 142-3.
  • Block, E. Reactions of Organosulfur Compounds; Academic: New York, 1978
  • Belen'kii, L.I. Chemistry of Organosulfur Compounds; Horwood: New York, 1990
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sulfolane". A list of authors is available in Wikipedia.