Ethylensulfid

THIIRANE · thirane · Ethylene sulphide · ethylene sufide · Thiacyclopropane · DIMETHYLENE SULFIDE · thiiran · hiirane

Identifikatoren & physikalische Daten

CAS No.	420-12-2
Summenformel	C2H4S
Durchschnittliche Molmasse	60,12 g/mol
Monoisotopische Masse	60,00337113 g/mol
SMILES	C1CS1
InChIKey	VOVUARRWDCVURC-UHFFFAOYSA-N
PubChem CID	9865
ChEMBL	CHEMBL3184935
ChEBI	CHEBI:30977
EC No.	206-993-9
DTXSID	DTXSID3049411
Lokaler Name	Ethylensulfid

Chemische & physikalische Eigenschaften

XLogP	0,6
Polarare Oberfläche (TPSA)	25,3
H-Brücken-Donoren	0
H-Brücken-Akzeptoren	1
Frei drehbare Bindungen	0
Schwere Atome	3
Formalladung	0
Komplexität	10,3
Stoffklassen	Other Classes -> Sulfur Compounds
SpringerMaterials Properties	Schoenflies notation
Dichte	1.0130 g/cu cm at 20 °C1.01 g/mL at 25 °C (lit.)
Color/Form	Colorless liquid
Löslichkeit	Slightly soluble in ethanol and ethersoluble in acetone and chloroformInsoluble in waterChloroform (Soluble), Methanol (Sparingly)
Siedepunkt	decomposes at 57 °C55-56 °C (lit.)
Schmelzpunkt	-109 °C207-209℃
Polymerization	Polymerizes gradually.
Dampfdruck	250.0 [mmHg]250 mm Hg at 25 °C4.15 psi ( 20 °C)
Brechungsindex	Index of refraction: 1.4935 at 20 °Cn20/D 1.495(lit.)
Physical Description	Colorless liquid[HSDB]
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 graduallyreacts with 4(4'-nitrobenzyl) pyridine
Flammpunkt	50 °F
Lagerbedingungen	-20°C
Aggregatzustand	liquid
Farbe	Colorless to Almost colorless
Spezifische Wärmekapazität	Cp(gas): 0.89 J/(g·K), at 25℃
BRN	102379
Henry-Konstante	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 (Verteilungskoeffizient)	0.556 (est)
CAS Datenbank	420-12-2(CAS DataBase Reference)
EPA chemische Informationen	Thiirane (420-12-2)

Sicherheit & Vorschriften

GHS-Einstufung	DangerH225 (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.H225: Highly Flammable liquid and vapor [Danger Flammable liquids]
Gefahrenübersicht	A skin and eye irritantToxic by inhalation and ingestion[HSDB] An eye irritant that may cause serious injuryEffects after intraperitoneal injection (LD50 in rats = 42 mg/kg) include flaccid paralysis without anesthesia[MSDSonline]
Hazard Classes and Categories	Flam. Liq. 2 (100%)Flammable liquids - Category 2
Skin, Eye, and Respiratory Irritations	Ethylene sulfide is ... an eye and dermal irritant.
Hazardous Reactivities and Incompatibilities	May polymerize violently in presence of acids, especially when warm.Reacts with 4(4´-nitrobenzyl)pyridine.
Entsorgungsverfahren	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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand 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.
Wechselwirkungen	WHEN TESTED FOR ETHYLENE-LIKE ACTIVITY & ETHYLENE ANTAGONISM USING TOBACCO LEAVES, ETHYLENE SULFIDE SHOWED APPARENT ETHYLENE ACTIVITY.
Umweltverhalten	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).
Lebensmitteluntersuchungswerte	Ethylene sulfide has been identified, but not quantified, as a volatile flavor component of meat flavoring in mutton and beef products(1).
Unerwünschte Wirkungen	Neurotoxin - Other CNS neurotoxin
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.
Human Toxicity Excerpts	/OTHER TOXICITY INFORMATION/ Ethylene sulfide is highly toxic when ingested, highly to moderate by inhalation, and an eye and dermal irritant.
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 streamsits former use in the US as a biocide(1) may have resulted in its direct release to the environment(SRC).
Sediment/Soil Concentrations	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).
Carcinogen Classification	Ethylene sulfideGroup 3: Not classifiable as to its carcinogenicity to humansVolume 11: (1976) Cadmium, Nickel, Some Epoxides, Miscellaneous Industrial Chemicals and General Considerations on Volatile Anaesthetics1987
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 sulfidethese 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.
F	10-13-23
Wassergefährdungsklasse (WGK)	3
TSCA-Inventar-Status	TSCA listed
UN-Transportnummer	UN 1992 3/PG 2
Zollcode	29349990
RTECS-Nr.	KX3500000
R-Sätze (R)	11-23/25-41-43
Gefahrensymbole	F,T
Sicherheitshinweise (S)	16-36/37/39-45-39-26
Gefahrenklasse	6.1(a)Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Flam. Liq. 2
Verpackungsgruppe	I
Lagerklasse	3 - Flammable liquids
Gefahrstoffdaten	420-12-2(Hazardous Substances Data)

Anwendungen & Verwendung

Verwenden

Ethylene 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.