Thiirane
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Thiirane
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CAS No:
420-12-2
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Formula:
C2H4S
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Chemical Name:
Thiirane
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Synonyms:
Thiirane;Ethylene sulfide;Thiacyclopropane;Thiirene,2,3-dihydro-;Ethylene episulfide;NSC 89690
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CAS No:
Description
clear colourless liquid
Thiirane is a saturated organic heteromonocyclic parent and an organosulfur heterocyclic compound.
Thiirane Basic Attributes
60.12
60.12
206-993-9
A2W5165740
89690
DTXSID3049411
Colorless liquid
29349990
Characteristics
25.3
0.81 (est)
1.0368 g/cm3 @ Temp: 0 °C
203-208 °C
55-56 °C
50 °F
1.574
In water, 2.8X10+4 mg/L at 25 deg C (est)
Freezer
4.15 psi ( 20 °C)
Henry's Law constant = 3.46X10-4 atm-cu m/mol at 25 °C (est)
Heat of formation = 51.6 kJ/mol (liq); 82.0 kJ/mol (gas). Gibbs free energy = 96.8 kJ/mol (gas). Entropy = 255.2 J/molK (gas)|Specific heat = 53.3 J/molK (gas)|Polymerizes gradually; reacts with 4(4'-nitrobenzyl) pyridine|Hydroxyl radical reaction rate constant = 2.06X10-12 cu cm/molec-sec at 25 °C (est)
Safety Information
I
6.1(a)
UN 1992 3/PG 2
3
11-23/25-41-43
16-36/37/39-45-39-26
KX3500000
F,T
Stable at room temperature, but may have butylmercaptan added to enhance stability. Flammable.
P210-P261-P280-P301 + P310-P305 + P351 + P338-P311
H225-H301 + H331-H318
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.
May polymerize violently in presence of acids, especially when warm.|Reacts with 4(4´-nitrobenzyl)pyridine.
|Danger|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P280, P301+P310, P303+P361+P353, P304+P340, P305+P351+P338, P307+P311, P311, P321, P330, P337+P313, P370+P378, P403+P233, P403+P235, P405, and P501
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.
Ethylene sulfide is ... an eye and dermal irritant.
SOIL: Ethylene sulfide was identified but not quantified in soil samples, using GC-MS, collected in November 1998 from a hillside site of an impacted bomb where chemical warfare was used in August 1998(1).
Toxicity
WHEN TESTED FOR ETHYLENE-LIKE ACTIVITY & ETHYLENE ANTAGONISM USING TOBACCO LEAVES, ETHYLENE SULFIDE SHOWED APPARENT ETHYLENE ACTIVITY.
LD50 Mouse oral 35.6 mg/kg|LD50 Rat oral 178 mg/kg|LC50 Rat inhalation 4000 ppm/30 min|LC50 Rat inhalation 2800 ppm/1 hr|For more Non-Human Toxicity Values (Complete) data for ETHYLENE SULFIDE (7 total), please visit the HSDB record page.
Ethylene sulfide's former US production and use as a chemical intermediate(1) may have resulted in its release to the environment through various waste streams; its former use in the US as a biocide(1) may have resulted in its direct release to the environment(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 26(SRC), determined from a structure estimation method(2), indicates that ethylene sulfide is expected to have very high mobility in soil(SRC). Volatilization of ethylene sulfide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-4 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Ethylene sulfide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.50X10+2 mm Hg(4). Ethylene oxide hydrolyzes slowly in fresh and salt water(5); by analogy, ethylene sulfide may act similarly and therefore hydrolysis on moist soil may be a slow environmental fate process(SRC). Biodegradation data were not available(SRC, 2008).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 26(SRC), determined from a structure estimation method(2), indicates that ethylene sulfide 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 3.5X10-4 atm-cu m/mole, 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 8 hours and 5 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 0.81(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Ethylene oxide hydrolyzes slowly in fresh and salt water(8); by analogy ethylene sulfide may act similarly(SRC). The half-life for this reaction is 12-14 days for pH's between 5-7 in fresh water and 9-11 days in salt water(8-10). Biodegradation data were not available(SRC, 2008).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), ethylene sulfide, which has a vapor pressure of 250 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase ethylene sulfide 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 8 days (SRC), calculated from its rate constant of 2.0X10-12 cu cm/molecule-sec at 25 °C, that was derived using a structure estimation method(3). Ethylene sulfide does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of ethylene sulfide with photochemically-produced hydroxyl radicals has been estimated as 2.0X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). The rate constant for the vapor-phase reaction of ethylene sulfide with ozone has been estimated as <1.7X10-20 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(1). This corresponds to an atmospheric half-life of about 8 days at an atmospheric concentration of 7X10+11 ozone molecules per cu cm(2). Ethylene sulfide is expected to undergo hydrolysis in the environment due to the presence of a functional group that hydrolyzes under environmental conditions(3). Ethylene oxide hydrolyzes slowly in fresh and salt water(4); by analogy ethylene sulfide may act similarly(SRC). The half-life for this reaction is 12-14 days for pH's between 5-7 in fresh water and 9-11 days in salt water(4-6). Ethylene sulfide does not contain chromophores that absorb at wavelengths >290 nm(3) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
An estimated BCF of 3 was calculated in fish for ethylene sulfide(SRC), using an estimated log Kow of 0.81(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
Using a structure estimation method based on molecular connectivity indices(1), the Koc of ethylene sulfide can be estimated to be 26(SRC). According to a classification scheme(2), this estimated Koc value suggests that ethylene sulfide is expected to have very high mobility in soil.
The Henry's Law constant for ethylene sulfide is estimated as 3.5X10-4 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that ethylene sulfide is expect 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 8 hours(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 approximately 5 days(SRC). Ethylene sulfide 's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). Ethylene sulfide is expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 250 mm Hg(3).
Ethylene sulfide has been identified, but not quantified, as a volatile flavor component of meat flavoring in mutton and beef products(1).
Occupational exposure to ethylene sulfide may occur through inhalation and dermal contact with this compound at workplaces where ethylene sulfide was produced or used. Limited monitoring data indicate that the general population may be exposed to ethylene sulfide via ingestion of food. (SRC)
Drug Information
/OTHER TOXICITY INFORMATION/ Ethylene sulfide is highly toxic when ingested, highly to moderate by inhalation, and an eye and dermal irritant.
divinyl sulfide
Thiirane Use and Manufacturing
...SYNTHESIZED BY REACTION OF 2-HALOETHYLTHIOCYANATES WITH SODIUM SULFIDE. OTHER METHODS...INCL...(1) REACTION OF ETHYLENE CARBONATE WITH SODIUM OR POTASSIUM THIOCYANATE; (2) REACTION OF ETHYLENE MONOTHIOCARBONATE WITH SODIUM CARBONATE... ...METHODS OF SYNTHESIS INCL...(3) REACTION OF ETHYLENE OXIDE WITH THIOUREA, INORGANIC THIOCYANATES OR CARBONYL SULFIDE.|PROBABLY BY REACTION OF ETHYLENE OXIDE WITH POTASSIUM THIOCYANATE OR THIOUREA IN AQUEOUS SOLUTION
Chemical intermediate; biocide
(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.|(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.
Thiirane: ACTIVE|PATENTS HAVE BEEN FILED FOR USE OF ETHYLENE SULFIDE AS MONOMER... (EG, IN THE PRODN OF HOMOPOLYMERS & COPOLYMERS), AS A MODIFYING AGENT FOR OTHER POLYMERS (EG, CELLULOSE), AS CHEMICAL INTERMEDIATE (EG, FOR PESTICIDES AND LUBRICANT ADDITIVES) & AS DIRECT-ACTING DISINFECTANT.
RAULIN F, TOUPANCE G; SIMULTANEOUS GAS CHROMATOGRAPHIC SEPARATION OF VOLATILE ORGANIC SULFUR COMPOUNDS AND C1-C4 HYDROCARBONS; J CHROMAT 90: 218 (1974). GAS CHROMATOGRAPHY CAN BE USED FOR THE DETERMINATION OF ETHYLENE SULFIDE.
Computed Properties
Molecular Weight:60.12
XLogP3:0.6
Hydrogen Bond Acceptor Count:1
Exact Mass:60.00337130
Monoisotopic Mass:60.00337130
Topological Polar Surface Area:25.3
Heavy Atom Count:3
Complexity:10.3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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