Page last updated: 2024-12-06

sulfolane

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Sulfolane, also known as tetramethylene sulfone, is a colorless, odorless, hygroscopic, and highly polar aprotic solvent. It is synthesized through the reaction of butadiene with sulfur dioxide and water. Sulfolane has a wide range of applications in various industrial processes, including:
* Extraction of aromatic hydrocarbons from petroleum fractions
* Solvent for polymerization reactions
* Desulfurization of fuels
* Production of synthetic fibers
* Formulation of paints and coatings
* Battery electrolytes
Sulfolane is studied extensively due to its unique properties, including its high boiling point, excellent solvating ability, and ability to form stable complexes with various organic and inorganic compounds. Its high boiling point and non-flammability make it suitable for high-temperature applications. Its high dielectric constant makes it a good solvent for polar compounds. It is also used as a medium for carrying out organic reactions. Research on sulfolane continues to explore its potential applications in various fields, such as renewable energy, pharmaceutical development, and environmental remediation.'

sulfolane : 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 (285degreeC) 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. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID31347
CHEMBL ID3186899
CHEBI ID74794
SCHEMBL ID14301
MeSH IDM0061651

Synonyms (101)

Synonym
cyclobutylsulfone
1lambda6-thiolane-1,1-dione
EN300-18394
thiophan sulfone
sulfolan
tetrahydrothiophene dioxide
thiophane dioxide
1,1-dioxidetetrahydrothiophene
bondolane a
sulfalone
1,1-dioxidetetrahydrothiofuran
cyclic tetramethylene sulfone
thiocyclopentane-1,1-dioxide
nsc-46443
nsc46443
bondelane a
thiolane-1,1-dioxide
thiacyclopentane dioxide
sulphoxaline
sulfolane
1,1-dioxothiolan
dihydrobutadiene sulfone
sulpholane
cyclotetramethylene sulfone
wln: t5swtj
2,4,5-tetrahydrothiophene-1,1-dioxide
tetramethylene sulfone
thiolane 1,1-dioxide
tetrahydrothiophene, 1,1-dioxide
inchi=1/c4h8o2s/c5-7(6)3-1-2-4-7/h1-4h
thiophene, tetrahydro-, 1,1-dioxide
tetrahydrothiophene 1,1-dioxide
126-33-0
sulfolane, 99%
ai3-09541
dihydrobutadiene sulphone
hsdb 122
einecs 204-783-1
nsc 46443
dioxothiolan
brn 0107765
ccris 2310
tetrahydrothiofen-1,1-dioxid [czech]
tetrahydrothiophene 1-dioxide
2,3,4,5-tetrahydrothiophene-1,1-dioxide
T0115
AKOS002676003
NCGC00248771-01
tetrahydrothiofen-1,1-dioxid
ec 204-783-1
unii-y5l06ah4g5
y5l06ah4g5 ,
5-17-01-00039 (beilstein handbook reference)
tox21_200628
dtxsid3027037 ,
NCGC00258182-01
cas-126-33-0
dtxcid407037
AKOS015955444
FT-0689267
CHEBI:74794 ,
(ch2)4so2
STL268898
1??-thiolane-1,1-dione
SCHEMBL14301
sulfolane [usp-rs]
sulfolane [mi]
sulfolane [hsdb]
tetramethylenesulphone
tetra-hydrothiophene-1,1-dioxide
tetramethylene-sulfone
tetramethylene sufone
sulpholan
tetrahydrothiophen-1,1-dioxide
tetrahydro-thiophene-1,1-dioxide
tetrahydrothiophene-1,1-dioxide
tetramethylene-sulphone
tetramethylene sulphone
tetrahydothiophene-1,1-dioxide
thiophene, 1,1-dioxide-tetrahydro-
1,1-dioxide tetrahydrothiofuran
thiophane 1,1-dioxide
W-108395
CHEMBL3186899
mfcd00005484
F1294-0027
sulfolane, purum, >=98.0% (gc)
sulfolane, analytical standard
sulfolane, redistilled from glass
Q416239
residual solvent class 2 - sulfolane
tetrahydrothiophene1,1-dioxide
tetrahydrothiophene-s,s-dioxide
1-thiolane-1,1-dione
bondelane a; bondolane a; cyclic tetramethylene sulfone; cyclotetramethylene sulfone; nsc 46443
acetylthiocholinechloride
PS-11978
AMY33385
D78046
QXB ,
CS-0020029

Research Excerpts

Overview

Sulfolane is an industrial solvent commonly used for extraction of aromatic hydrocarbons in the oil refining process, as well in the purification of natural gas. It is a widely used industrial solvent that is often used for gas treatment (sour gas sweetening; hydrogen sulfide removal from shale and coal processes, etc.), and may be found in pharmaceuticals as a residual solvent used in the manufacturing processes.

ExcerptReferenceRelevance
"Sulfolane is an industrial solvent and emerging organic contaminant affecting groundwater around the world, but little is known about microbes capable of biodegrading sulfolane or the pathways involved. "( Identification and Characterization of a Dominant Sulfolane-Degrading Rhodoferax sp. via Stable Isotope Probing Combined with Metagenomics.
Collins, RE; Kasanke, CP; Leigh, MB, 2019
)
2.21
"Sulfolane is an industrial solvent commonly used for extraction of aromatic hydrocarbons in the oil refining process, as well in the purification of natural gas. "( Development and Validation of an Analytical Method for Quantitation of Sulfolane in Rat and Mouse Plasma by GC-MS.
Cooper, SD; Fernando, RA; Robinson, VG; Silinski, MAR; Uenoyama, T; Waidyanatha, S, 2019
)
2.19
"Sulfolane is a widely used industrial solvent that is often used for gas treatment (sour gas sweetening; hydrogen sulfide removal from shale and coal processes, etc.), and in the manufacture of polymers and electronics, and may be found in pharmaceuticals as a residual solvent used in the manufacturing processes. "( Development of a chronic noncancer oral reference dose and drinking water screening level for sulfolane using benchmark dose modeling.
Carakostas, MC; Gaylor, DW; Haws, LC; Perry, C; Tachovsky, JA; Thompson, CM, 2013
)
2.05
"Sulfolane is a solvent which produces hypothermia and decreased oxygen consumption following acute exposure. "( Acute behavioral toxicity of sulfolane: influence of hypothermia.
Dyer, RS; Ruppert, PH, 1985
)
2

Effects

ExcerptReferenceRelevance
"Sulfolane has leached into groundwaters at sour gas treatment plant sites, and poses a risk for off-site contamination."( Nutrient stimulation of sulfolane biodegradation in a contaminated soil from a sour natural gas plant and in a pristine soil.
Fedorak, PM; Greene, EA, 2001
)
1.34

Dosage Studied

The study looked at the pretreatment conditions such as temperature, sulfolane/water ratio, and alkaline catalyst (NaOH) dosage. It is anticipated that these values, along with the hazard identification and dose-response modeling, should be informative for risk assessors and regulators.

ExcerptRelevanceReference
" This hyperthermia was significant at a dosage of 3000 micrograms."( Thermoregulatory responses of the rabbit to central neural injections of sulfolane.
Gordon, CJ; Mohler, FS, 1989
)
0.51
" Motor activity in figure-of-eight mazes was assessed 1 h after dosing in testing rooms maintained at either 20."( Acute behavioral toxicity of sulfolane: influence of hypothermia.
Dyer, RS; Ruppert, PH, 1985
)
0.56
" It is anticipated that these values, along with the hazard identification and dose-response modeling described herein, should be informative for risk assessors and regulators interested in setting health-protective drinking water guideline values for sulfolane."( Development of a chronic noncancer oral reference dose and drinking water screening level for sulfolane using benchmark dose modeling.
Carakostas, MC; Gaylor, DW; Haws, LC; Perry, C; Tachovsky, JA; Thompson, CM, 2013
)
0.79
" Optimization of the pretreatment conditions such as temperature, sulfolane/water ratio, and alkaline catalyst (NaOH) dosage were comprehensively investigated for effective lignin extraction from willow."( Pretreatment of willow using the alkaline-catalyzed sulfolane/water solution for high-purity and antioxidative lignin production.
Chen, J; Ji, X; Jiang, W; Lyu, G; Mao, J; Shao, L; Wang, C; Xu, F; Xu, M; Yang, G; Yoo, CG; Zhong, L, 2020
)
1.05
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
polar aprotic solventA solvent with a comparatively high relative permittivity (or dielectric constant), greater than ca. 15, and a sizable permanent dipole moment, that cannot donate suitably labile hydrogen atoms to form strong hydrogen bonds.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
sulfoneAn organosulfur compound having the structure RS(=O)2R (R =/= H).
tetrahydrothiophenes
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency17.94580.002541.796015,848.9004AID1347395
thyroid stimulating hormone receptorHomo sapiens (human)Potency27.47270.001628.015177.1139AID1259385
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (72)

TimeframeStudies, This Drug (%)All Drugs %
pre-199018 (25.00)18.7374
1990's5 (6.94)18.2507
2000's8 (11.11)29.6817
2010's27 (37.50)24.3611
2020's14 (19.44)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 61.78

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index61.78 (24.57)
Research Supply Index4.39 (2.92)
Research Growth Index4.95 (4.65)
Search Engine Demand Index100.92 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (61.78)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (1.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational1 (1.25%)0.25%
Other78 (97.50%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]