Sulfolane
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Sulfolane
structure -
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CAS No:
126-33-0
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Formula:
C4H8O2S
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Chemical Name:
Sulfolane
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Synonyms:
Thiophene,tetrahydro-,1,1-dioxide;Cyclic tetramethylene sulfone;Cyclotetramethylene sulfone;Sulfolan;Sulfolane;Tetrahydrothiophene 1,1-dioxide;Tetramethylene sulfone;1,1-Dioxothiolan;Bondolane A;Thiacyclopentane dioxide;Tetrahydrothiophene dioxide;Sulpholane;Thiophane dioxide;Bondelane A;Thiophane 1,1-dioxide;Thiolane 1,1-dioxide;Tetrahydrothiophene S,S-dioxide;NSC 46443;Sulfolane SG;1λ6-Thiolane-1,1-dione;208252-54-4
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CAS No:
Description
colourless crystals Sulfolane is a colorless oily liquidColorless oily liquid with a weak oily odor. Solidifies (freezing point is 79°) and sinks on first contact with water, then mixes with water. F.
Sulfolane is a colorless oily liquid with a weak oily odor. Solidifies (freezing point is 79° F) and sinks on first contact with water, then mixes with water. (USCG, 1999)|Liquid; OtherSolid
Sulfolane is a colorless oily liquid with a weak oily odor. Solidifies (freezing point is 79° F) and sinks on first contact with water, then mixes with water. (USCG, 1999)|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.
Sulfolane Basic Attributes
120.166
120.17
204-783-1
Y5L06AH4G5
46443
3334
DTXSID3027037
White or creamy white, crystalline powder
29349990
Characteristics
42.5
-0.8
Sulfolane is a colorless oily liquid with a weak oily odor. Solidifies (freezing point is 79° F) and sinks on first contact with water, then mixes with water. (USCG, 1999)
1.2606 g/cm3 @ Temp: 30 °C
27.4-27.8 °C
285 °C
177 DEG C (350 DEG F) (OPEN CUP)
n 20/D 1.484(lit.)
H2O: >=100g/l soluble ;Freely soluble in alcohol, soluble in dilute mineral acids
Store in a cool, dry place. Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.
0.01 mm Hg ( 20 °C)
4.2 (vs air)
LD50 orally in rats: 1.54 ml/kg (Smyth)
Odorless
Slightly bitter taste
Henry's Law constant = 4.8X10-6 atm-cu m/mole (est)
HIGHLY POLAR CMPD WITH OUTSTANDING SOLVENT PROPERTIES|Heat of solution = -22 Btu/lg = -12 Cal/g|Heat of fusion: 11.44 kJ/kg; dielectric constant: 43.3|Hydroxyl radical reaction rate constant = 1.3X10-11 cu cm/molecule-sec at 25 deg (est)
Water soluble.
Sulfonates, Phosphonates, and Thiophosphonates, Organic
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].
-9,500 Btu/lb= -5,300 Cal/g
Safety Information
Ⅲ
UN3334 Aviation regulated liquid, n.o.s., Hazard class: 9; Labels: 9-Miscellaneous hazardous material. Technical Name Required.
1
6.1
23-25
XN0700000
Xn
Stable. Combustible. Incompatible with strong oxidizing agents.
P301 + P312 + P330
H302
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
Nitronium tetrafluoroborate /is potentially explosive/ in sulfolane.
USEPA; Chemical Hazard Information Profile Draft Report: Sulfolane (1984). Available data on the hazards of sulfolane is reviewed.|European Chemicals Bureau; IUCLID Dataset, Tetrahydrothiophene 1,1-dioxide (126-33-0) (2000 CD-ROM edition). Available from the database query page: http://ecb.jrc.it/esis/esis.php as of June 27, 2005.
Special Hazards of Combustion Products: Toxic, irritating gases may be generated in fires. (USCG, 1999)
|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P273, P281, P301+P310, P301+P312, P304+P340, P308+P313, P312, P330, P331, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 550 companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H320: Causes eye irritation [Warning Serious eye damage/eye irritation]|P201, P202, P264, P281, P305+P351+P338, P308+P313, P337+P313, P405, and P501
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent dust cloud. Avoid inhalation of asbestos dust. SMALL DRY SPILL: With clean shovel, place material into clean, dry container and cover loosely; move containers from spill area. SMALL SPILL: Pick up with sand or other non-combustible absorbent material and place into containers for later disposal. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Cover powder spill with plastic sheet or tarp to minimize spreading. Prevent entry into waterways, sewers, basements or confined areas. (ERG, 2016)
Goggles or face shield; rubber gloves. (USCG, 1999)
Combustible when exposed to heat or flame.
Water or foam may cause frothing.|Wear goggles and self-contained breathing apparatus. Extinguish with water, foam, dry chemical, or carbon dioxide.
Poisonous gases are produced in fire.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
Liquid irritating to eyes, not irritating to skin.
This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Sulfolane is produced, as an intermediate or a final product, by process units covered under this subpart.
| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.
Sulfolane was detected in effluents of advanced waste water treatment plants in Orange county, CA(1). Sulfolane was detected in landfill leachate from municipal waste in Japan at 1200 ug/L(2).
Toxicity
After oral or parenteral admin to rodents, analeptic effects of sulfolane were nearly additive with those of metrazol. When injected simultaneously with phenobarbital, it decr phenobarbital sleeping time in mice, but incr time when admin 1 hr before.|Rats receiving sulfolane at 240-300 mg/kg, ip, 20 min before irradiation showed 3 times as many bone marrow karyocytes as did control animals after receiving 300-900 rads gamma-irradiation. Mice receiving 120-240 mg/kg showed twice as many as controls.
LD50 Rat oral 1941 mg/kg|LD50 Rat ip 1600 mg/kg|LD50 Rat sc 1606 mg/kg|LC50 Rat inhalation >12 mg/L/4 hr|For more Non-Human Toxicity Values (Complete) data for SULFOLANE (14 total), please visit the HSDB record page.
Sulfolane's use as a solvent for the extraction of benzene, toluene, and xylene from mixtures with aliphatic hydrocarbons and its use in the extraction of acidic components, eg, hydrogen sulfide, carbon dioxide, carbonyl sulfide, carbon dioxide and mercaptans, from sour gas streams(1), may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), Koc values in the range of 4-35 measured in aquifer material from a natural gas plant(2), indicates that sulfolane is expected to have very high mobility in soil(SRC). Volatilization of sulfolane from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.8X10-6 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Sulfolane is not expected to volatilize from dry soil surfaces given a vapor pressure of 0.0062 mm Hg(4). Microcosms constructed of groundwater and sediment obtained from natural gas plants suggest that sulfolane degrades readily under aerobic conditions (half-lives of 2-3 days), but was shown to be recalcitrant under anaerobic conditions(5,6).|AQUATIC FATE: Based on a classification scheme(1), Koc values in the range of 4-35 measured in aquifer material from a natural gas plant(2), indicates that sulfolane is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 4.8X10-6 atm-cu m/mole (SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 6 and 64 days, respectively(SRC). Sulfolane is not expected to undergo hydrolysis in water due to the lack of hydrolyzable functional groups(3). According to a classification scheme(5), BCF values of <13, measured in carp(6) suggest that bioconcentration in aquatic organisms is low(SRC). Sulfolane did not pass the OECD ready biodegradation test(6), suggesting that biodegradation will not be fast. However, aquifer slurries constructed with soil and groundwater from a natural gas plant were shown to be capable of degrading sulfolane under aerobic conditions (half-lives of approximately 2-3 days); no degradation was observed under anaerobic conditions(7,8).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfolane, which has a vapor pressure of 0.0062 mm Hg at 25 °C (2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase sulfolane is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 29 hours(SRC), calculated from its rate constant of 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3).
The rate constant for the vapor-phase reaction of sulfolane with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 29 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Sulfolane is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2) nor to directly photolyze due to the lack of absorption in the environmental UV spectrum (>290 nm).
7.08|BCFs of <1.3 and <13 were measured for sulfolane at concentrations of 2.5 mg/L and 0.25 mg/L, respectively, using carp which were exposed over a 6-week period(1). According to a classification scheme(2), these BCF data suggest that bioconcentration in aquatic organisms is low(SRC).
Sulfolane exhibited very high mobility in batch adsorption experiments using aquifer material from 3 natural gas plants in Canada(1). In each experiment, the soil adsorption isotherms were linear and the soil adsorption coefficient (Kd) of sulfolane was very low (Kd < 1). The corresponding Koc values in these low organic (0.2-0.9% organic carbon) materials were in the range of 4-35. The Koc value of sulfolane using a humus rich soil (pH = 6.9, 3.6% organic carbon) was 3(1). According to a classification scheme(2), this range of Koc values suggests that sulfolane is expected to have very high mobility in soil(SRC).
The Henry's Law constant for sulfolane is estimated as 4.8X10-6 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sulfolane is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 6 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 64 days(SRC). Sulfolane's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Sulfolane is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure 0.0062 mm Hg(3).
NIOSH (NOES Survey 1981-1983) has statistically estimated that 6,461 workers (315 of these are female) are potentially exposed to sulfolane in the US(1). Occupational exposure to sulfolane may occur through inhalation and dermal contact with this compound at workplaces where sulfolane is produced or used(SRC).
Drug Information
Convulsants; Radiation-protective Agents|Antibacterial|Sulfolane dosages that alter seizure susceptibility were determined using audiogenic (AG), pentylenetetrazol (PTZ) and hippocampal afterdischarge (AD) seizure models. The presence of AG seizures and potentiation of PTZ seizures were investigated in rats injected IP with 0, 200, 400 or 800 mg/kg; AD activity was assessed only at the highest and lowest dosages. The dose-dependent hypothermia associated with sulfolane treatment was controlled in Experiment I and a replication study (Experiment II) by testing under isothermic conditions. The effect of body temperature was measured directly in Experiment III by comparing AG seizure incidence and characteristics exhibited by hypothermic and normothermic animals. Audiogenic seizures were elicited in nearly half of the 800 mg/kg animals in both Experiments I and II. Sulfolane-induced hypothermia, maximal at 3 hours, partially protected against AG seizure characteristics. Potentiation of PTZ seizure severity (800 mg/kg) and duration (800 and 400 mg/kg) also were observed. None of the hippocampal AD parameters was affected significantly by sulfolane treatment.
Substances that act in the brain stem or spinal cord to produce tonic or clonic convulsions, often by removing normal inhibitory tone. They were formerly used to stimulate respiration or as antidotes to barbiturate overdose. They are now most commonly used as experimental tools. (See all compounds classified as Convulsants.)|Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)
Absorbed rapidly and completely by the gastrointestinal tract. Passed easily through the blood-brain barrier. ...Urine and fecal elimination /times/ were 36.5 and 59 hours respectively. ...Sulfolane is rapidly absorbed by the blood and excreted in urine. ...Excreted mainly as 3-hydroxysulfolane, with some unchanged sulfolane, the percentage of the latter increasing with increasing oral doses.|When administered intraperitoneally, sulfolane is excreted both unchanged and as 3-hydroxysulfolane.
When administered intraperitoneally, sulfolane is excreted both unchanged and as 3-hydroxysulfolane.
Plasma half-life is between 3 1/2-5 hours.
Very mildly irritating to the eyes. (USCG, 1999)
INGESTION: induce vomiting. SKIN OR EYE CONTACT: flush with water. (USCG, 1999)
Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/
sulfolane
Sulfolane Use and Manufacturing
Prepared by catalytic hydrogenation of sulfolene oxides: Mahan, Fauske, US 2578565 (1951 to Phillips Petroleum).|... From butadiene and sulfur dioxide ... Evans, Morris, US 2360859 (1944 to Shell).|Sulfolane ... is made by reacting sulfur dioxide and butadiene to form sulfolene, which is then hydrogenated to give sulfolane
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
Fuels and fuel additives
Fuels and related products
1,000,000 - 10,000,000 lb|Thiophene, tetrahydro-, 1,1-dioxide is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|(1986) >1 million - 10 million pounds|(1990) >1 million - 10 million pounds|(1994) >1 million - 10 million pounds|For more U.S. Production (Complete) data for SULFOLANE (7 total), please visit the HSDB record page.
Commercially available as anhydrous sulfolane and as sulfolane containing 3% wt deionized water|Grade: Technical|Sulfolane-W (97% 1,1-tetrahydrothiophenedioxide and 3% water)
Computer and electronic product manufacturing|Thiophene, tetrahydro-, 1,1-dioxide: ACTIVE
Computed Properties
Molecular Weight:120.17
XLogP3:-0.8
Hydrogen Bond Acceptor Count:2
Exact Mass:120.02450067
Monoisotopic Mass:120.02450067
Topological Polar Surface Area:42.5
Heavy Atom Count:7
Complexity:128
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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