Grundinformationen
- Standard-SMILES
C1CS1- InChIKey
VOVUARRWDCVURC-UHFFFAOYSA-N- Summenformel
- C2H4S
- Durchschnittliche Molmasse
- 60,12 g/mol
- Monoisotopische Masse
- 60,00337113
Überblick
Thiirane is a saturated organic heteromonocyclic parent and an organosulfur heterocyclic compound.
Namen und Bezeichner
- Bevorzugter Name
- Thiirane
- IUPAC
- thiirane
- Lokaler Name
- Ethylensulfid
- Englischer Name
- ETHYLENE SULFIDE
- Summenformel
- C2H4S
- Molmasse
- 60.12
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
420-12-2- PubChem CID
- 9865
- DTXSID
DTXSID3049411- ChEMBL
CHEMBL3184935- ChEBI
CHEBI:30977- UNII
- A2W5165740
- EC Number
- 206-993-9
- Nikkaji
- J2.585B
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 0,6
- Polarare Oberfläche (TPSA)
- 25,3 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 1
- Frei drehbare Bindungen
- 0
- Schwere Atome
- 3
- Formalladung
- 0
- Komplexität
- 10,3
Experimentelle und physikochemische Eigenschaften
Vapor Pressure
250.0 [mmHg]
250 mm Hg at 25 °C
Other Experimental Properties
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
Physikochemische Eigenschaften
- Schmelzpunkt
- 207 · 207-209℃
- Siedepunkt
- 55 · 55-56 °C (lit.)
- Dichte
- 1.01 g/mL · 1.01 g/mL at 25 °C (lit.)
- Dampfdruck
- 4.15 psi · 4.15 psi ( 20 °C)
- Brechungsindex
- 20 · n20/D 1.495(lit.)
- Flammpunkt
- 50 °F · 50 °F
- storage temp.
- -20 °C · -20°C
- Wasserlöslichkeit
- Insoluble in water
- Löslichkeit
- Chloroform (Soluble), Methanol (Sparingly)
- Aggregatzustand
- liquid
- Farbe
- Colorless to Almost colorless
- Spezifische Wärmekapazität
- 0.89 J/ · Cp(gas): 0.89 J/(g·K), at 25℃
- BRN
- 102379 · 102379
- Henry's Law Constant
- 2.8 · 2.8×10-2 mol/(m3Pa) at 25℃, HSDB (2015)
- Stabilität
- Stable at room temperature, but may have butylmercaptan added to enhance stability. Flammable.
- InChI
- 1S/C2H4S/c1-2-3-1/h1-2H2
- InChIKey
- VOVUARRWDCVURC-UHFFFAOYSA-N
- SMILES
- C1CS1
- LogP
- 0.556 · 0.556 (est)
- CAS Datenbank
- 420 · 420-12-2(CAS DataBase Reference)
- EPA chemische Informationen
- Thiirane (420-12-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]
P210, P233, P240, P241, P242, P243, P261, P264, P264+P265, P270, P271, P280, P301+P316, P303+P361+P353, P304+P340, P305+P354+P338, P316, P317, P321, P330, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
Gefahrenhinweise
Hazard Classes and Categories
Flam. Liq. 2 (100%)
Flammable liquids - Category 2
Hazardous Reactivities and Incompatibilities
May polymerize violently in presence of acids, especially when warm.
Reacts with 4(4´-nitrobenzyl)pyridine.
Sicherheit und Schutzausrüstung
Disposal Methods
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.
Preventive Measures
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.
Toxikologische Informationen
Environmental Fate
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).
Soil Adsorption/Mobility
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.
Artificial Pollution Sources
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).
Carcinogen Classification
Ethylene sulfide
Group 3: Not classifiable as to its carcinogenicity to humans
Volume 11: (1976) Cadmium, Nickel, Some Epoxides, Miscellaneous Industrial Chemicals and General Considerations on Volatile Anaesthetics
1987
1987
Environmental Bioconcentration
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).
Volatilization from Water/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).
Non-Human Toxicity Excerpts
/LABORATORY ANIMALS: Acute Exposure/ Ethylene and propylene sulfides are of about equal toxicity when administered as vapors by the respiratory route in 1 hr and 6 hr acute exposures.
/LABORATORY ANIMALS: Acute Exposure/ In rats, ingestion of high doses...caused depression of CNS with unconsciousness. It is irritating to surface tissues and mucous membranes. Inhalation... caused congestion, edema and hemorrhage in lungs.
/LABORATORY ANIMALS: Acute Exposure/ ... The thiiranes of greatest interest to industry are ethylene, propylene and chloropropylene sulfides. They may be prepared by interaction of the appropriate epoxide with potassium thiocyanate. A critical estimation of the vapor toxicities of these compounds was undertaken, utilizing dynamic gassing equipment and larger groups of rats in eposure periods of 1 and 6 hr. Rats exposed to the 3 episulfides showed marked similarities in the lesions found in tissues. In the lungs, congestion ranging from slight to severe was a common finding. Edema and slight to moderate hemorrhage were seen. A moderate to severe degree of cuffing was noted. A few instances of pneumonia and bronchitis were recorded. Degenerative changes in the trachea were slight or absent. No striking alterations were noted in the heart or liver. Kidney changes afforded some evidence of a difference in the action of chloropropylene sulfide as compared with the non-halogenated episulfides. Protein casts were seen in the cortex and the medullary region, with degeneration and necrosis, in animals exposed to chloropropylene sulfide; these changes were not conspicuous in rats exposed to ethylene and propylene sulfides. Ethylene and propylene sulfides are of about equal toxicity when administered as vapors by the respiratory route in 1 hr and 6 hr acute exposures. Chloropropylene sulfide is approximately twice as toxic as the non-halogenated episulfides under these conditions. A consistent departure from Haber's rule (Ct = constant) is evident for all 3 episulfides when the results from the 2 exposure duration are compared.
/LABORATORY ANIMALS: Acute Exposure/ Ethylene sulfide is a mild skin and eye irritant with recovery within 24 hr.
For more Non-Human Toxicity Excerpts (Complete) data for ETHYLENE SULFIDE (8 total), please visit the HSDB record page.
Sicherheitsdaten
- F
- 10-13-23
- wgk
- 3
- tsca
- TSCA listed
- ridadr
- UN 1992 3/PG 2
- hs_code
- 29349990
- RTECS-Nr.
- KX3500000
- risk_code
- 11-23/25-41-43
- hazard_code
- F,T
- safety_code
- 16-36/37/39-45-39-26
- hazard_class
- 6.1(a)
- packing_group
- I
- Speicherklasse
- 3 - Flammable liquids
- Giftige Stoffe Daten
- 420-12-2(Hazardous Substances Data)
- Hazard Classifications
- Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Flam. Liq. 2
Chemie und Industrie
Verwendung und Herstellung
Uses
Used as a chemical intermediate; [HSDB]
Chemical intermediate; biocide
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
(1979) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.
(1981) NO EVIDENCE OF COMMERCIAL PRODN IN U.S.
Methods of 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
General Manufacturing Information
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.
Anwendungen
VerwendenEthylene sulfide is generally used in the preparation of organosulfur compounds, especially for mercaptoethylation of primary and secondary amines to obtain aminothiols.It is used in the synthesis of dendritic thioether ligands to stabilize gold nanoparticles (Au NPs).Chitosan can be chemically modified by treating ethylene sulfide to obtain a biopolymer for the removal of divalent cations from aqueous solutions.
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