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Basic Information

Molecular Structure:
CAS No.:	126-33-0
Name:	Sulfolane
Article Data:	98

Formula:	C₄H₈O₂S
Molecular Weight:	120.172
Synonyms:	1,1-Dioxothiolan;Bondelane A;Bondolane A;Cyclic tetramethylene sulfone;Cyclotetramethylenesulfone;NSC 46443;Sulfolan;Sulpholane;Tetrahydrothiophene1,1-dioxide;Tetrahydrothiophene S,S-dioxide;Tetrahydrothiophene dioxide;tetramethylene sulfone;Thiacyclopentane dioxide;Thiolane 1,1-dioxide;Thiophane 1,1-dioxide;Thiophane dioxide;
EINECS:	204-783-1
Density:	1.261 g/cm³
Melting Point:	27.4 °C
Boiling Point:	285.568 °C at 760 mmHg
Flash Point:	170.678 °C
Solubility:	soluble in water
Appearance:	colourless crystals
Hazard Symbols:	Xn
Risk Codes:	22
Safety:	23-25
PSA:	42.52000
LogP:	1.27580

Synthetic route

: 110-01-0
thiophene

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With silica gel; magnesium monoperoxyphthalate hexahydrate In dichloromethane for 0.833333h; Heating;	100%
With sodium tungstate (VI) dihydrate; dihydrogen peroxide In methanol; water at 40℃;	100%
With selenium(IV) oxide; dihydrogen peroxide In water; ethyl acetate chemoselective reaction;	99%

: 77-79-2
3-Sulfolene

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With triethylsilane; 1% Pd on activated carbon In water at 45℃; for 20h; Green chemistry; chemoselective reaction;	100%
With ethanol; platinum Hydrogenation;
With water; palladium Hydrogenation;

: 110-01-0
thiophene

A: 1600-44-8
1-oxothiolane

B: 126-33-0
sulfolane

Conditions

Conditions	Yield
With urea-hydrogen peroxide at 85℃; for 0.116667h;	A 87% B 9%
With dihydrogen peroxide In water at 30 - 35℃; for 24h; Sealed tube; Green chemistry;	A 66% B 60%
With dihydrogen peroxide; titanium(IV) isopropylate; L-Tartaric acid; silica gel In methanol; water at 25℃; for 4h; Title compound not separated from byproducts;	A 96 % Spectr. B 2%

: 1600-44-8
1-oxothiolane

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With nitronium tetrafluoborate In dichloromethane at 25℃; for 5h;	68%
With peroxynitrous acid at 25℃; for 0.166667 - 4h; pH=7.4 - 12.7; Reactivity; phosphate buffer;	3.14%
With bromine In water at 20℃; Equilibrium constant; Thermodynamic data; ΔH, ΔS, various temperature;

tetramethylenebis(dimethylglyoximato)(pyridine)cobalt(III) (45): tetramethylenebis(dimethylglyoximato)(pyridine)cobalt(III) (45)

A: 126-33-0
sulfolane

B mono- and bis(sulfur dioxide) insertion products: mono- and bis(sulfur dioxide) insertion products

Conditions

Conditions	Yield
With sulfur dioxide for 24h; Ambient temperature;	A 20% B n/a

: 17200-23-6
3-Isopropoxythiolane 1,3-dioxide

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With nickel; isopropyl alcohol at 175℃; under 51485.6 Torr; Hydrogenation;

: 110-52-1
1,4-dibromo-butane

A: 126-33-0
sulfolane

B: 24308-29-0
1,2-oxathiane-2-oxide

Conditions

Conditions	Yield
With sulfur dioxide; tetraethylammonium bromide In acetonitrile at 60 - 80℃; electrolysis;	A 45 % Turnov. B 54 % Turnov.

: 1192-16-1
2,3-dihydrothiophene-1,1-dioxide

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With hydrogen; nickel at 20℃; Kinetics; rate of hydrogenation as a function of deformation of crystal structure of the catalyst; other catalysts : Rh, Pd and Pt;

: 4724-56-5
1,4-ditosyloxybutane

A: 126-33-0
sulfolane

B: 24308-29-0
1,2-oxathiane-2-oxide

Conditions

Conditions	Yield
With sulfur dioxide; tetraethylammonium bromide In acetonitrile at 60 - 80℃; electrolysis;	A 45 % Turnov. B 45 % Turnov.

: 110-01-0
thiophene

ozone containing oxygen: ozone containing oxygen

: 126-33-0
sulfolane

Conditions

Conditions	Yield
With chloroform

Raw Materials

17200-23-6

4724-56-5

1600-44-8

110-52-1

110-01-0

Downstream Products

350-30-1

375-72-4

129-40-8

393-01-1

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Sulfolane is an organic compound with the formula C₄H₈O₂S. The IUPAC name of this chemical is thiolane 1,1-dioxide. With the CAS registry number 126-33-0, it is also named as 2,3,4,5-Tetrahydrothiophene-1,1-dioxide. The product's category is Organics. Besides, it is a colourless crystal.

Physical properties about Sulfolane are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 13.961; (4)ACD/KOC (pH 7.4): 13.961; (5)#H bond acceptors: 2; (6)Polar Surface Area: 42.52 Å²; (7)Index of Refraction: 1.486; (8)Molar Refractivity: 27.337 cm³; (9)Molar Volume: 95.289 cm³; (10)Polarizability: 10.837×10^-24cm³; (11)Surface Tension: 35.61 dyne/cm; (12)Density: 1.261 g/cm³; (13)Flash Point: 170.678 °C; (14)Enthalpy of Vaporization: 50.357 kJ/mol; (15)Boiling Point: 285.568 °C at 760 mmHg; (16)Vapour Pressure: 0.005 mmHg at 25°C.

Preparation: the original method was to first allow butadiene to react with sulfur dioxide. This yields sulfolene, which was then hydrogenated using Raney nickel as a catalyst to give sulfolane.

Uses of Sulfolane: it is widely used as an industrial solvent, especially in the extraction of aromatic hydrocarbons from hydrocarbon mixtures and to purify natural gas. Sulfolane was found to be highly effective in separating high purity aromatic compounds from hydrocarbon mixtures using liquid-liquid extraction. This process is still widely used today in refineries and the petrochemical industry. 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 distillation; 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.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed. When you are using it, do not breathe gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer) and avoid contact with eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: C1CCS(=O)(=O)C1
(2)InChI: InChI=1/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
(3)InChIKey: HXJUTPCZVOIRIF-UHFFFAOYAA
(4)Std. InChI: InChI=1S/C4H8O2S/c5-7(6)3-1-2-4-7/h1-4H2
(5)Std. InChIKey: HXJUTPCZVOIRIF-UHFFFAOYSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1250mg/kg (1250mg/kg)		Russian Pharmacology and Toxicology Vol. 42, Pg. 97, 1979.
mouse	LD50	intravenous	1080mg/kg (1080mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Archives Internationales de Pharmacodynamie et de Therapie. Vol. 119, Pg. 423, 1959.
mouse	LD50	oral	1900mg/kg (1900mg/kg)		"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 560, 1969.
rabbit	LD50	skin	3180uL/kg (3.18mL/kg)	LIVER: OTHER CHANGES KIDNEY, URETER, AND BLADDER: OTHER CHANGES SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	National Technical Information Service. Vol. OTS0535072,
rat	LC	inhalation	> 250mg/m³/8H (250mg/m³)		National Technical Information Service. Vol. OTS0535072,
rat	LD50	intraperitoneal	1600mg/kg (1600mg/kg)		Toxicologist. Vol. 4, Pg. 22, 1984.
rat	LD50	oral	1540uL/kg (1.54mL/kg)		American Industrial Hygiene Association Journal. Vol. 30, Pg. 470, 1969.
rat	LD50	skin	> 3800mg/kg (3800mg/kg)		British Journal of Industrial Medicine. Vol. 23, Pg. 302, 1966.
rat	LD50	subcutaneous	1620uL/kg (1.62mL/kg)		National Technical Information Service. Vol. OTS0535072,

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