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Thiodiglykol
THIODIGLYCOL · 2-HYDROXYETHYL SULFIDE · Thiodiethanol · Ethanol, 2,2'-thiobis- · 2-(2-hydroxy-ethylsulfanyl)-ethanol · Tedegyl · Glycine A · glyecinea
Identifikatoren & physikalische Daten
| CAS No. | 111-48-8 |
|---|---|
| Summenformel | C4H10O2S |
| Durchschnittliche Molmasse | 122,19 g/mol |
| Monoisotopische Masse | 122,04015056 g/mol |
| SMILES | OCCSCCO |
| InChIKey | YODZTKMDCQEPHD-UHFFFAOYSA-N |
| PubChem CID | 5447 |
| ChEMBL | CHEMBL444480 |
| ChEBI | CHEBI:75184 |
| EC No. | 203-874-3 |
| DTXSID | DTXSID6026878 |
| Lokaler Name | Thiodiglykol |
Chemische & physikalische Eigenschaften
| XLogP | -0,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 65,8 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 7 |
| Formalladung | 0 |
| Komplexität | 28,9 |
| Stoffklassen | Other Classes -> Sulfur Compounds (Alcohols) |
| Kosmetika | Antioxidant |
| SpringerMaterials Properties | Boiling point |
| LogP (Verteilungskoeffizient) | log Kow = -0.63-0.75 |
| Geruch | Characteristic odorOdor similar to hydrogen sulfide |
| Dichte | 1.1793 g/cu cm at 25 °CBulk density: 9.85 lb/galRelative density (water = 1): 1.181.1847 @ 20°C1.221 g/mL at 25 °C(lit.) |
| Viscosity | 0.652 cP at 20 °C |
| Color/Form | LiquidSyrupy, colorless, liquid |
| Löslichkeit | In water, miscible at 20 °CMiscible with waterMiscible with ethanol, chloroform, ethyl acetatesoluble in etherslightly soluble in benzene1000 mg/mL at 20 °CSolubility in water, g/100ml at 20 °C: 100alcohol: miscible(lit.) |
| Flammpunkt | 113 °C (235 °F) - closed cup320 °F (160 °C) (Closed cup)160 °C o.c.>230 °F |
| Siedepunkt | 282 °C282.00 °C. @ 760.00 mm Hg164-166 °C20 mm Hg(lit.) |
| Decomposition | When heated to decomposition it emits highly toxic fumes of /sulfur oxide/.Decomposes on heating. This produces toxic and corrosive fumes including acetic acid fumes, hydrogen sulfide and sulfur oxides. |
| Schmelzpunkt | −16 °C(lit.) |
| Dampfdruck | 0.26Pa at 20℃ |
| Brechungsindex | n20/D 1.5215(lit.) |
| Lagerbedingungen | -20°C |
| Aggregatzustand | liquid |
| pKa (Säurekonstante) | 14.14±0.10(Predicted) |
| Merck | 14,9330 |
| BRN | 1236325 |
| Henry-Konstante | 5.2×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. Reacts with a wide variety of compounds. Flammable. |
| Kosmetik-Inhaltsstoffe Funktionen | ANTIOXIDANT |
| LogP (Verteilungskoeffizient) | -0.75 at 25℃ |
| Oberflächenspannung | 54mN/m at 20°C |
| CAS Datenbank | 111-48-8(CAS DataBase Reference) |
| NIST chemische Informationen | Thiodiglycol(111-48-8) |
| EPA chemische Informationen | Ethanol, 2,2'-thiobis- (111-48-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] |
|---|---|
| Regulatorische Informationen | Chemical: Ethanol, 2,2'-thiobis-Ethanol, 2,2'-thiobis- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Ethanol, 2,2'-thiobis- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 03-05-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/11663Thiodiglycol: Does not have an individual approval but may be used under an appropriate group standard |
| Brandgefahren | Combustible. |
| Brandpotenzial | Combustible when exposed to heat or flame.Combustible. |
| Gefahrenübersicht | A mild eye and respiratory tract irritant[ICSC] Causes mild skin irritation and moderate eye irritation in experimental animalsNot sensitizing in guinea pig maximization testNo evidence of mutagenicityEmergency treatment: Glycols[HSDB] An eye irritant[eChemPortal: ESIS] A mild skin and moderate eye irritantCauses diffuse hepatitis and other GI and endocrine changes in subcutaneous lethal-dose study of mice[RTECS] An eye irritant[Alfa Aesar MSDS] |
| Reaktive Gruppe | Alcohols and Polyols |
| EG-Einstufung | Symbol: XiR: 36S: (2) |
| Special Reports | Reddy G et alToxicity assessment of thiodiglycol. Int J Toxicol 24 (6): 435-42 (2005)Munro NB et alThe sources, fate, and toxicity of chemical warfare agent degradation products. Environ Health Perspect 107 (12): 933-74 (1999)Organization for the Prohibition of Chemical WeaponsConvention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and Their Destruction. The Chemical Weapons Convention (CWC) is an international treaty which bans the development, production, stockpiling, and transfer or use of chemical weapons. The Convention mandates the destruction and prohibition of chemical weapons and related facilities and provides for restrictions on international trade in toxic chemicals and precursors.[Available from, as of January 31, 2018: http://www.opcw.org/chemical-weapons-convention/] |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes including acetic acid fumes, hydrogen sulfide and sulfur oxides. Reacts violently with strong acids and strong oxidants. This produces hydrogen sulfide. |
| Air and Water Reactions | No rapid reaction with air. No rapid reaction with water. |
| NFPA Hazard Classification | 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. |
| Toxic Combustion Products | Special hazards arising from the substance or mixture: Carbon oxides, sulfur oxides. |
| Hazard Classes and Categories | Eye Irrit. 2 (100%)Eye irritation - category 2Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation) |
| Brandbekämpfung | Use water spray, foam, alcohol-resistant foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest.Rinse skin with plenty of water or shower.First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.Rinse mouth. Do NOT induce vomiting. |
| Sichere Lagerung | See Chemical Dangers. |
| Firefighting Hazards | Evaporation at 20 °C is negligiblea harmful concentration of airborne particles can, however, be reached quickly on spraying.Decomposes on heating. This produces toxic and corrosive fumes including acetic acid fumes, hydrogen sulfide and sulfur oxides. |
| Brandbekämpfungsverfahren | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.To fight fire, use alcohol foam, carbon dioxide, dry chemical. |
| Lagerbedingungen | Keep container tightly closed in a dry and well-ventilated place. |
| Reinigungsverfahren | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Soak up with inert absorbent material and dispose of as hazardous waste. Keep in suitable, closed containers for disposal.Personal protection: protective gloves and safety goggles. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Entsorgungsverfahren | SRP: 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 air, soil or watereffects on animal, aquatic and plant lifeand conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this materialContaminated packaging: Dispose of as unused product.The U.S. Army is pilot testing chemical hydrolysis as a method for destroying the chemical agents stockpiled at Aberdeen, Maryland (HD mustard agent) ... The chemical agents ...which are stored only in bulk ton containers, will be hydrolyzed (using ... water for HD) at slightly below the boiling temperature of the solution. The resulting hydrolysate at Aberdeen, which will contain thiodiglycol as the primary reaction product, will be treated by activated sludge biodegradation in sequencing batch reactors to oxidize organic constituents prior to discharge to an on-site federally owned wastewater treatment facility.In January 2002, the Army announced plans to accelerate the destruction of the mustard agent stockpile located at Aberdeen Proving Ground in Maryland ... . Step 1: Container Draining: Workers drain the mustard agent from the steel containers by manually removing the containers' plugs through a glove box system that has been used safely by the Army for agent handling for more than 10 years. A tube is inserted and the agent is pumped to an agent holding tank. Step 2: Agent Destruction and Confirmation: The mustard agent is fed into a tank containing hot water where it is vigorously mixed, causing the mustard agent to react with the water to form a biodegradableliquid byproduct called hydrolysate. ... Thiodiglycol, an organic chemical used in the paint and ink industry, is readily biodegradable. A large batch made up of four well-mixed, small batches is tested to confirm complete agent destruction. Step 3: Hydrolysate Disposal: Although free of mustard agent, the hydrolysate still is considered an industrial hazardous waste and requires further treatment. This post-treatment step - where the hydrolysate is added to a mixture of ordinary sewage treatment bacteria that "digests" the thiodiglycol to form carbon dioxide and wet solids - /will be conducted offsite/.The principles of complex, ecologically-safe technology for the destruction of battle gas mustard were worked out. This technology was based on the reaction alkaline detoxication of mustardthe major component of reaction mixture obtained after detoxication was thiodiglycol. Thorough thiodiglycol mineralization was achieved by electrochemical treatment. Electrolysis products were biologically utilized in biosorber. |
| Verschüttetes entsorgen | Personal protection: protective gloves and safety goggles. Collect leaking and spilled liquid in covered containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations. |
| Preventive Measures | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Environmental precautions: Do not let product enter drains.Precautions for safe handling: Avoid contact with skin and eyes. Avoid inhalation of vapor or mist.Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.For more Preventive Measures (Complete) data for Thiodiglycol (7 total), please visit the HSDB record page. |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Ökotoxizitätswerte | EC50Species: Pseudomonas putida (bacterium)Concentration: >10,000 mg/L for 17 hrEffects: cell multiplication inhibition test /Conditions of bioassay not specified in source examined/Species: Scenedesmus subspicatus (algae)Concentration: >500 mg/L for 72 hrLC50Species: Leuciscu idus (cyprinoid fish)Conditions: staticConcentration: >10,000 mg/L for 96 hr |
| Umweltverhalten | TERRESTRIAL FATE: Koc values of 0.12-13.70 indicate that thiodiglycol is expected to have very high mobility in soil(1). Volatilization of thiodiglycol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(2). Thiodiglycol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.09X10-4 mm Hg at 25 °C(3). Thiodiglycol was biologically transformed to thiodiglycolic acid at zero-order rate coefficients of 9.41X10-7 to 6.26X10-6 mol/L hr in 3 soils, with lag periods of 2 to 3.75 days, biodegradation was noted in 2 other soils, but transformation rates were not reported(1). The optimum pH for the biodegradation of thiodiglycol in soil has been reported as 8.25(4).AQUATIC FATE: Koc values of 0.12-13.70(1) indicate that thiodiglycol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 1.9X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). Thiodiglycol did not undergo hydrolysis at pH 4, 7 or 11(1). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow of -0.63(5) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low. Thiodiglycol did not undergo photolysis in aqueous solution after irradiation by sunlight for 14 days(1). Based on studies done in aerobic sludge with 19% biodegradation in 4 weeks(6), anaerobic sludge with 42% biodegradation in 185 days(7) and in soil where biodegradation was noted in 5 soils(1), biodegradation may be an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), thiodiglycol, which has a vapor pressure of 5.09X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase thiodiglycol 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 14 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC), that was derived using a structure estimation method(3). Thiodiglycol 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). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Toxizitätsübersicht | IDENTIFICATION AND USE: Thiodiglycol is a syrupy, colorless, liquid. It is used as chemical intermediate, additive for textile printing. It is also a Schedule 2B precursor (dual-use chemicals with low to moderate commercial use and high-risk precursors) to mustard gas, sesquimustard, HT, T, and Q. It is used to manufacture ball-point pen ink. HUMAN STUDIES: The hydrolysis products of mustard gas are reported to exhibit toxicity. However, thiodiglycol, the major breakdown product, exhibits low toxicity. Therefore, it is likely that the majority of the toxic effects attributed to the hydrolysis products are due to unreacted mustard and bis(chloroethyl)polysulfides present in the original material. ANIMAL STUDIES: Acute dermal irritation was tested on rabbits. A very slight erythema was noted in 1 out of 3 animals 1 hour after treatment until day 4. The effect was completely reversible within 5 days. No cutaneous reactions were observed in the other 2 animals. In a guinea pig maximization test the challenge resulted in no skin reaction in thiodiglycol treated animals. In the Rat Inhalation Hazard Test, no mortality was reported after 8 hr exposure to a saturated atmosphere at room temperature. Immediately after the start of exposure, the animals showed attempts to escape. Irritation of the mucous membranes was observed 1 hr after start of exposure. In a prenatal developmental toxicity study in rats a significant increase in dumbbell ossifications of thoracic vertebral bodies was noted (12% versus 5.2% in control). Other significant increases in skeletal variations, such as rudimentary cervical ribs were also observed (7.1% versus 1.2% in control) as well as a general increase in total variations (concerning affected fetuses/litter: 52.9% versus 38.6% in control). Thiodiglycol did not induce reverse gene mutations in Salmonella typhimurium strains TA98, TA100, TA1535, TA1537, and E. coli WP2uvrA at concentrations up to 5 mg/plate in the presence or absence of metabolic activation. Thiodiglycol was not mutagenic in mouse lymphoma, and in vivo mouse micronucleus assays, but it induced chromosomal aberrations in Chinese hamster ovarian (CHO) cells. The mechanism of vesication from sulfur mustard remains unknown in spite of 80 years of investigation. It was reported that sulfur mustard-related inhibition of one or more protein (serine/threonine) phosphatases in tissue cytosol in vitro, could be a mechanism common to other vesicants such as cantharidin and Lewisite. This inhibition was related to the concentration of thiodiglycol, the hydrolysis product of sulfur mustard, rather than to the concentration of mustard itself. ECOTOXICITY STUDIES: It was not toxic to bluegill sunfish at 1,000 mg/L. |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ ... It was slowly biodegraded under anaerobic conditions. It was not toxic to bluegill sunfish at 1,000 mg/L and its metabolism and environmental and biochemical effects are summarized. |
| Signs and Symptoms | Cough. Nausea.Redness. Pain.Diarrhoea. Nausea. Vomiting. |
| Ongoing Test Status | EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPAICSS Dashboard ApplicationAvailable from, as of March 27, 2018: http://actor.epa.gov/dashboard/] |
| Soil Adsorption/Mobility | Four soils obtained from US military installations and two soils from an interlaboratory collaborative exercise were tested for Koc of thiodiglycol(1). Soils included Dugway Proving Ground (DPG), Fort McClellan (FMC), Rocky Mountain Arsenal (RMA), woodstone sandy loam (WSL), treaty soil 1 (TS1) and treaty soil 2 (TS2). Soil characteristics and Koc values are shown below. These results indicate that thiodiglycol could be very mobile in the environment(1).[Table#7135] |
| Human Toxicity Excerpts | /OTHER TOXICITY INFORMATION/ The hydrolysis products of mustard gas are also reported to exhibit toxicity. However, thiodiglycol (2,2'-thiobis[ethanol]), the major breakdown product, exhibits low toxicity. Therefore, it is likely that the majority of the toxic effects attributed to the hydrolysis products are due to unreacted mustard and bis(chloroethyl)polysulfides present in the original material.[Marrs, T. C. et alChemical Warfare Agents: Toxicology and Treatment, John Wiley and Sons: Chichester, p. 144-73 (1996)] |
| Artificial Pollution Sources | Thiodiglycol's production and use as an intermediate for elastomers and antioxidants(1), as a solvent for dyes in textile printing(1), in the manufacture of ball-point pen ink(2), and as an ingredient in printer ink cartridges(3) may result in its release to the environment through various waste streams(SRC). Thiodiglycol is used as a precursor for sulfur mustard(4) and is a hydrolysis product of the chemical weapon sulfur mustard(5). |
| Environmental Biodegradation | Thiodiglycol, present at 100 mg/L, reached 19% of its Theoretical BOD in 4 weeks using an activated sludge inoculum at 30 mg/L in the Japanese MITI test(1). Thiodiglycol was biological transformed to thiodiglycolic acid at zero-order rate coefficients of 9.41X10-7 to 6.26X10-6 mol/L hr in 3 soils, with lag periods of 2 to 3.75 days(2). Biodegradation was noted in 2 other soils, but transformation rates were not reported(2). The optimum pH for the biodegradation of thiodiglycol in soil has been reported as 8.25(3).ANAEROBIC: Thiodiglycol was biodegraded 42% after incubation in anaerobic sludge for 185 days with a 52 day lag period(1). |
| Sediment/Soil Concentrations | SOIL: Thiodiglycol was identified in soil samples collected in November 1988 from a site of chemical warfare incident involving sulfur mustard in Iraq close to the borders of Turkey and Iran(1). Thiodiglycol is a hydrolysis product of the chemical weapon sulfur mustard(2). |
| DHS Chemicals of Interest (COI) | Thiodiglycol302.2000000000000002Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques. |
| F | 3-13-23 |
| Wassergefährdungsklasse (WGK) | 1 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN1230 - class 3 - PG 2 - Methanol, solution |
| Zollcode | 29309090 |
| RTECS-Nr. | KM2975000 |
| R-Sätze (R) | 36-36/37/38-39/23/24/25-23/24/25-11 |
| Toxizität | guinea pig,LD50,oral,3960mg/kg (3960mg/kg),KIDNEY, URETER, AND BLADDER: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)GASTROINTESTINAL: OTHER CHANGES,Journal of Industrial Hygiene and Toxicology. Vol. 23, Pg. 259, 1941. |
| Gefahrensymbole | Xi,T,F |
| Sicherheitshinweise (S) | 23-26-36/37/39-45-36-36/37-16-7 |
| Gefahrstoffdaten | 111-48-8(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
antineoplastic, alkylating agent