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Sulfolane

CAS No.
126-33-0
Chemical Name:
Sulfolane
Synonyms
TETRAMETHYLENE SULFONE;SULPHOLANE;TETRAHYDROTHIOPHENE 1,1-DIOXIDE;foL;SULFOLAN;TETRAHYDROTHIOPHEN-1,1-DIOXIDE;Sulfolone;Sulfalone;Thiophane dioxide;TETRAMETHYLENE SULPHONE
CBNumber:
CB3852996
Molecular Formula:
C4H8O2S
Molecular Weight:
120.17
MDL Number:
MFCD00005484
MOL File:
126-33-0.mol
MSDS File:
SDS
Last updated:2024-11-07 21:39:59

Sulfolane Properties

Melting point 20-26 °C (lit.)
Boiling point 104 °C/0.2 mmHg (lit.) 285 °C (lit.)
Density 1.261 g/mL at 25 °C (lit.)
vapor density 4.2 (vs air)
vapor pressure 0.01 mm Hg ( 20 °C)
refractive index n20/D 1.484(lit.)
Flash point 330 °F
storage temp. Store below +30°C.
solubility >=100g/l soluble
form Liquid After Melting
color Clear yellow
Water Solubility soluble
FreezingPoint 26℃
Sensitive Hygroscopic
Merck 14,8955
BRN 107765
Dielectric constant 44.0
Stability Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey HXJUTPCZVOIRIF-UHFFFAOYSA-N
LogP 0 at 20℃
CAS DataBase Reference 126-33-0(CAS DataBase Reference)
FDA UNII Y5L06AH4G5
NIST Chemistry Reference Thiophene, tetrahydro-, 1,1-dioxide(126-33-0)
EPA Substance Registry System Sulfolane (126-33-0)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS07,GHS08
Signal word  Danger
Hazard statements  H302-H360FD
Precautionary statements  P202-P264-P270-P280-P301+P312-P308+P313
Hazard Codes  Xn
Risk Statements  22
Safety Statements  23-25
WGK Germany  1
RTECS  XN0700000
TSCA  Yes
HS Code  29349990
Toxicity LD50 orally in rats: 1.54 ml/kg (Smyth)
NFPA 704
1
1 0

Sulfolane price More Price(47)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 8.07993 Sulfolane for synthesis 126-33-0 250ML $60.5 2024-03-01 Buy
Sigma-Aldrich 88965 Sulfolane analytical standard 126-33-0 5ml $70.1 2024-03-01 Buy
Sigma-Aldrich 8.07993 Sulfolane for synthesis 126-33-0 1L $182 2024-03-01 Buy
Sigma-Aldrich 8.07993 Sulfolane for synthesis 126-33-0 6kg $188 2024-03-01 Buy
Sigma-Aldrich 1601769 Residual Solvent Class 2 - Sulfolane 126-33-0 3x1.2ml $411 2024-03-01 Buy
Product number Packaging Price Buy
8.07993 250ML $60.5 Buy
88965 5ml $70.1 Buy
8.07993 1L $182 Buy
8.07993 6kg $188 Buy
1601769 3x1.2ml $411 Buy

Sulfolane Chemical Properties,Uses,Production

Uses

Sulfolane is widely used as an industrial solvent, especially in the extraction of aromatic hydrocarbons from 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 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.

Chemical Properties

colourless crystals

Chemical Properties

Sulfolane is a colorless oily liquid

Uses

Process solvent for extractions of aromatics and for purification of acid gases.

Uses

Sulfolane is used in lithium-ion batteries.

Uses

Selective solvent for liquid-vapor extractions.

Definition

ChEBI: Sulfolane is a member of the class of tetrahydrothiophenes that is tetrahydrothiophene in which the sulfur has been oxidised to give the corresponding sulfone. A colourless, high-boiling (285℃) liquid that is miscible with both water and hydrocarbons, it is used as an industrial solvent, particularly for the purification of hydrocarbon mixtures by liquid-vapour extraction. It has a role as a polar aprotic solvent. It is a sulfone and a member of tetrahydrothiophenes. It derives from a hydride of a tetrahydrothiophene.

Synthesis Reference(s)

Journal of the American Chemical Society, 63, p. 2939, 1941 DOI: 10.1021/ja01856a021

General Description

Colorless oily liquid with a weak oily odor. Solidifies (freezing point is 79°) and sinks on first contact with water, then mixes with water. F.

Air & Water Reactions

Water soluble.

Reactivity Profile

Mixing Sulfolane in equal molar portions with any of the following substances in a closed container caused the temperature and pressure to increase: chlorosulfonic acid and oleum [NFPA 1991]. With nitrating agents (nitronium tetrafluoroborate in Sulfolane) very highly exothermic reactions are known to occur, [J. Org. Chem., 1978, 43, 4677].

Hazard

Combustible. Toxic by ingestion.

Health Hazard

Very mildly irritating to the eyes.

Fire Hazard

Special Hazards of Combustion Products: Toxic, irritating gases may be generated in fires.

Industrial uses

Sulfolane is the most common commercially available sulfone solvent. The solvent, also known as tetrahydrothiophene-1,1-dioxide, is a colorless, highly polar liquid consisting of a fully hydrogenated five-member sulfur-carbon heterocyclic thiophene ring. The solvent is available as both anhydrous sulfolane and as sulfolane containing 3 wt% deionized water. Sulfolane is used as a reaction medium, as a solvent for a wide variety of organic chemicals and polymers, and as an extraction solvent.
Sulfolane is a very high boiling point, colorless liquid with a very high viscosity (10.3 centipoises) and medium surface tension value (35.5 dynes/cm).Sulfolane is miscible with water and many organic solvents.
Sulfolane is used to separate aromatic hydrocarbons from aliphatic hydrocarbons. The extraction process first developed by Shell Oil in 1959 and which is referred to as the "Sulfolane" process is used worldwide. The solvency of sulfolane for certain fatty acids and fatty acid esters is the basis for upgrading animal and vegetable fatty acids used in food products, paints, plastics, resins, and soaps.
Sulfolane is used to remove acidic components like hydrogen sulfide and carbon dioxide from gas feed stocks. Sulfolane is used as a polymerization solvent for the production of polysulfones, polysiloxanes, polyphenylene ethers, and other polymers. Sulfolane is said to increase the reaction rates, afford easier polymer purification, and improved thermal stability. Sulfolane is a solvent for dissolving a variety of polymers for use in the fiberspinning process.Cellulose and cellulose ester polymers can be plasticized with sulfolane to give improved flexibility and other physical property improvements. Other application areas that have used sulfolane include electronic and electrical uses, textile dye uses, curing of polysulfide sealant, and as a catalyst in certain synthetic reactions.

Potential Exposure

Sulfolane is used primarily as a process solvent for extraction of aromatics and for purification of acid gases. Used as a curing agent for epoxy resins, in medicine ash an antibacterial; fractionation of wood tars, tall oil, and other fatty acids; a component of hydraulic fluid; in textile finishing.

Carcinogenicity

Sulfolane was not mutagenic in bacterial assays with or without metabolic activation.

Shipping

UN3334 Aviation regulated liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material. Technical Name Required.

Purification Methods

prepared commercially by a Diels-Alder reaction of between 1,3-butadiene and sulfur dioxide, followed by Raney nickel hydrogenation. The principal impurities are water, 3-sulfolene, 2-sulfolene and 2-isopropyl sulfolanyl ether. It is dried by passage through a column of molecular sieves. Distil it under reduced pressure through a column packed with stainless steel helices. Again dry it with molecular sieves and distil. [Cram et al. J Am Chem Soc 83 3678 1961, Coetzee Pure Appl Chem 49 211 1977.] Alternatively, it is stirred at 50o, and small portions of solid KMnO4 are added until the colour persists during 1hour. Dropwise addition of MeOH then destroys the excess KMnO4; the solution is filtered, freed from potassium ions by passage through an ion-exchange column and dried under vacuum. It has also been distilled in a vacuum from KOH pellets. It is hygroscopic. [See Sacco et al. J Phys Chem 80 749 1976, J Chem Soc, Faraday Trans 1 73 1936 1977, 74 2070 1978, Trans Faraday Soc 62 2738 1966.] Coetzee has reviewed the methods of purification of sulfolane, and also the removal of impurities. [Coetzee in Recommended Methods of Purification of Solvents and Tests for Impurities, Coetzee Ed. Pergamon Press, 1982, Beilstein 17 I 5, 17 III/IV 37, 17/1 V 39.]

Incompatibilities

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Contact with nitronium tetrafluoroborate(1-) is potentially explosive.

26978-64-3
126-33-0
Synthesis of Sulfolane from 1-Butanesulfonic acid, 4-hydroxy-
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View Lastest Price from Sulfolane manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Sulfolane pictures 2024-12-03 Sulfolane
126-33-0
US $990.00-800.00 / g 1g 99% 5000 HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Sulfolane pictures 2024-12-03 Sulfolane
126-33-0
US $5.00 / KG 1KG 99.5% 1000mt/year Jinan Finer Chemical Co., Ltd
sulfolane pictures 2024-12-02 sulfolane
126-33-0
US $10.00 / kg 1kg 99% 5000 Hebei Zhuanglai Chemical Trading Co.,Ltd
  • Sulfolane pictures
  • Sulfolane
    126-33-0
  • US $990.00-800.00 / g
  • 99%
  • HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
  • Sulfolane pictures
  • Sulfolane
    126-33-0
  • US $5.00 / KG
  • 99.5%
  • Jinan Finer Chemical Co., Ltd
  • sulfolane pictures
  • sulfolane
    126-33-0
  • US $10.00 / kg
  • 99%
  • Hebei Zhuanglai Chemical Trading Co.,Ltd
2,3,4,5-TETRAHYDROTHIOPHENE-1,1-DIOXIDE LABOTEST-BB LT00239038 1,1-Dioxide tetrahydrothiofuran 1,1-Dioxidetetrahydrothiophene Thioxyclopentane-1,1-dioxide SULFOLANE, STANDARD FOR GC SULFOLANE SULFOLANE-W thiophanedioxide Thiophanesulfone thiophansulfone Thiophene, 1,1-dioxide-tetrahydro- thiophene,tetrahydro-,1,1-dioxide 1,1-Dioxothiolan Tetramethylene sulfone, 99+% tetrahydrothiophene-1,1-dioxide sulpholane Tetrahydrothiophene 1,1-dioxide, Tetramethylene sulfone tetrahydrothiophene1-dioxide tetrahydrothiophenedioxide tetrahydrothiophene-S,S-dioxide Tetramethy-leneaulphone Thiacyclopentane dioxide thiacyclopentanedioxide Thiocyclopentane-1,1-dioxide Thiophan sulfone Thiophane 1,1-dioxide TETRAMETHYLENE SULFONE GC STANDARD SulfolaneAnhydrous 2,3,4,5-Tetrahydrothiophene-1,1-dioxide=Thioxyclopentane-1,1-dioxide CYCLOBUTYLSULFONE TETRAMETHYLENE SULFONE (SULFOLANE) Sulfolane ,99% Sulfolane,Tetrahydrothiophene 1,1-dioxide, Tetramethylene sulfone Sulfolane, 80% w/w aq. soln. TetraMethylene sulfone, 99+% 250ML SULFOLANE FOR SYNTHESIS Thiolane 1,1-dioxide, Sulpholane Sulfolane, Standard for GC,>=99.5%(GC) Residual Solvent Class 2 - Sulfolane Sulfolane in dimethyl sulfoxide Sulfolane solution sulfolane:tetramethylene sulfone: tetrahydrothiophene 1,1-dioxide 1-Thiolane-1,1-dione 5-sulfoisophthalicacid,lithiumsaltsulfolane Bondelane A bondelanea Bondolane A bondolanea Cyclic tetramethylene sulfone cyclictetramethylenesulfone Cyclotetramethylene sulfone cyclotetramethylenesulfone Dihydrobutadiene sulfone Dihydrobutadiene sulphone dihydrobutadienesulphone Dioxothiolan Sulphoxaline Tetrahydothiophene-1,1-dioxide