Grundinformationen
- Standard-SMILES
OCCSCCO- InChIKey
YODZTKMDCQEPHD-UHFFFAOYSA-N- Summenformel
- C4H10O2S
- Durchschnittliche Molmasse
- 122,19 g/mol
- Monoisotopische Masse
- 122,04015056
Überblick
This material has many uses, including as a precursor to the sulfur mustard family of chemical weapons. It is chemically similar to thioglycol and is expected to react in a similar way to this material. See the chemical datasheet for thioglycol for more information.
Namen und Bezeichner
- Bevorzugter Name
- Thiodiglycol
- IUPAC
- 2-(2-hydroxyethylsulfanyl)ethanol
- Lokaler Name
- Thiodiglykol
- Englischer Name
- 2,2'-Thiodiethanol
- Summenformel
- C4H10O2S
- Molmasse
- 122.19
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
111-48-8- PubChem CID
- 5447
- DTXSID
DTXSID6026878- ChEMBL
CHEMBL444480- ChEBI
CHEBI:75184- UNII
- 9BW5T43J04
- EC Number
- 203-874-3
- Nikkaji
- J1.988G
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -0,6
- Polarare Oberfläche (TPSA)
- 65,8 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 3
- Frei drehbare Bindungen
- 4
- Schwere Atome
- 7
- Formalladung
- 0
- Komplexität
- 28,9
Experimentelle und physikochemische Eigenschaften
LogP
log Kow = -0.63
-0.63
-0.75
-0.63
Odor
Characteristic odor
Odor similar to hydrogen sulfide
Density
1.1793 g/cu cm at 25 °C
Bulk density: 9.85 lb/gal
Relative density (water = 1): 1.18
1.1847 @ 20°C
Color/Form
Liquid
Syrupy, colorless, liquid
Solubility
In water, miscible at 20 °C
Miscible with water
Miscible with ethanol, chloroform, ethyl acetate; soluble in ether; slightly soluble in benzene
1000 mg/mL at 20 °C
Solubility in water, g/100ml at 20 °C: 100
Flash Point
113 °C (235 °F) - closed cup
320 °F (160 °C) (Closed cup)
160 °C o.c.
Boiling Point
282 °C
282.00 °C. @ 760.00 mm Hg
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.
Physikochemische Eigenschaften
- Schmelzpunkt
- 16 °C · −16 °C(lit.)
- Siedepunkt
- 164 · 164-166 °C20 mm Hg(lit.)
- Dichte
- 1.221 g/mL · 1.221 g/mL at 25 °C(lit.)
- Dampfdruck
- 0.26 Pa · 0.26Pa at 20℃
- Brechungsindex
- 20 · n20/D 1.5215(lit.)
- Flammpunkt
- 230 °F · >230 °F
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- alcohol: miscible(lit.)
- Aggregatzustand
- liquid
- pka
- 14.14 · 14.14±0.10(Predicted)
- Merck
- 14 · 14,9330
- BRN
- 1236325 · 1236325
- Henry's Law Constant
- 5.2 · 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
- -0.75 at · -0.75 at 25℃
- Oberflächenspannung
- 54 mN/m · 54mN/m at 20°C
- CAS Datenbank
- 111 · 111-48-8(CAS DataBase Reference)
- NIST chemische Informationen
- Thiodiglycol(111-48-8)
- EPA chemische Informationen
- 2 · Ethanol, 2,2'-thiobis- (111-48-8)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Warning
H319: 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)
Warning
H319 (100%): 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)
Gefahrenhinweise
Regulatory Information
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/11663
Thiodiglycol: Does not have an individual approval but may be used under an appropriate group standard
Fire Potential
Combustible when exposed to heat or flame.
Combustible.
Hazards Summary
A mild eye and respiratory tract irritant; [ICSC] Causes mild skin irritation and moderate eye irritation in experimental animals; Not sensitizing in guinea pig maximization test; No evidence of mutagenicity; Emergency treatment: Glycols; [HSDB] An eye irritant; [eChemPortal: ESIS] A mild skin and moderate eye irritant; Causes diffuse hepatitis and other GI and endocrine changes in subcutaneous lethal-dose study of mice; [RTECS] An eye irritant; [Alfa Aesar MSDS]
Special Reports
Reddy G et al; Toxicity assessment of thiodiglycol. Int J Toxicol 24 (6): 435-42 (2005)
Munro NB et al; The sources, fate, and toxicity of chemical warfare agent degradation products. Environ Health Perspect 107 (12): 933-74 (1999)
Organization for the Prohibition of Chemical Weapons; Convention 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/]
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.
Hazard Classes and Categories
Eye Irrit. 2 (100%)
Eye irritation - category 2
Specific target organ toxicity - Single exposure - Category 3 (Respiratory tract irritation)
Eye Irrit. 2
Sicherheit und Schutzausrüstung
First Aid Measures
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.
Firefighting Hazards
Evaporation at 20 °C is negligible; a 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.
Fire Fighting Procedures
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.
Cleanup Methods
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.
Disposal Methods
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 quality; potential migration in air, soil or water; effects on animal, aquatic and plant life; and 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 material; Contaminated 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 mustard; the 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.
Spillage 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.
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.
Toxikologische Informationen
Ecotoxicity Values
EC50; Species: Pseudomonas putida (bacterium); Concentration: >10,000 mg/L for 17 hr; Effects: cell multiplication inhibition test /Conditions of bioassay not specified in source examined/
EC50; Species: Scenedesmus subspicatus (algae); Concentration: >500 mg/L for 72 hr; Effects: cell multiplication inhibition test /Conditions of bioassay not specified in source examined/
LC50; Species: Leuciscu idus (cyprinoid fish); Conditions: static; Concentration: >10,000 mg/L for 96 hr
Environmental Fate
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).
Toxicity Summary
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.
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/[USEPA; ICSS Dashboard Application; Available 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 al; Chemical 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).
Regulatorische Informationen
DHS Chemicals of Interest (COI)
Thiodiglycol
30
2.2000000000000002
Chemical Weapons/Chemical Weapons Precursors chemical material that, if stolen or diverted, can be converted into weapons using simple chemistry, equipment, or techniques.
Sicherheitsdaten
- F
- 3-13-23
- wgk
- 1
- tsca
- TSCA listed
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29309090
- RTECS-Nr.
- KM2975000
- risk_code
- 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.
- hazard_code
- Xi,T,F
- safety_code
- 23-26-36/37/39-45-36-36/37-16-7
- Giftige Stoffe Daten
- 111-48-8(Hazardous Substances Data)
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
The mechanism of vesication from sulfur mustard remains unknown in spite of 80 years of investigation. /The authors/ recently reported sulfur mustard-related inhibition of one or more protein (serine/threonine) phosphatases in tissue cytosol in vitro, suggesting a mechanism common to other vesicants such as cantharidin and Lewisite. /Their/ investigation showed that this inhibition was related to the concentration of 2,2'-thiobis-ethanol (thiodiglycol), the hydrolysis product of sulfur mustard, rather than to the concentration of mustard itself. Related work showed an increase in the rate of NAD (but not NADP) reduction upon the addition of thiodiglycol to mouse liver cytosol. This result provided evidence that metabolism beyond thiodiglycol may be contributing to protein phosphatase inhibition. This observation indicated that metabolism involving one or more dehydrogenases may be necessary to produce the ultimate inhibitor of the protein phosphatases. /The authors/ report here that thiodiglycol is a substrate for horse liver alcohol dehydrogenase (Km = 3.68+/-0.45 mM and Vmax = 0.22 +/-0.01 umol/ min/ mg protein) and for pyridine nucleotide-linked enzymes in mouse liver and human skin cytosol. The alcohol dehydrogenase-specific inhibitor 4-methylpyrazole inhibited the oxidation of thiodiglycol by the pure horse liver enzyme as well as by the enzymes in human skin and mouse liver cytosol, indicating that the activity in the tissue preparations is also alcohol dehydrogenase.
Metabolism/Metabolites
Thiodiglycol is oxidized to four metabolites. In three of the four metabolites sulfur undergoes oxidation and in two of them acetic acid is formed. No information of toxic effects of the metabolites is recorded ... In rodents thiodiglycol can conjugate with glucuronic acid and sulfate or it can be converted to thiodiglycolic acid which can conjugate with glycine and glucuronic acid ... The major metabolite was thiodiglycol sulfoxide, minor metabolites were thiodiglycol sulfone, S-(2-hydroxyethylsulfinyl)acetic acid and S-(2-hydroxyethylthio)acetic acid. Only around 0.5 to 1% of thiodiglycol was excreted unchanged.
Skin blisters /from mustard gas exposure/ may be aspirated and the fluid obtained analyzed for thiodiglycol. The same estimation may be performed in blood and urine in order to differentiate blistering produced by ... other agents such as Lewisite ...
Metabolic studies with radioactively labelled mustard gas were performed in rodents ... The following metabolic pathways were proposed: hydrolyses to thiodiglycol and S-oxidation to sulfoxide and sulfone, followed by conjugation. Urinary metabolites in rats consisted of thiodiglycol and conjugates (15%), glutathione-bis-beta-chloroethylsulfide conjugates (45%), glutathione-bis-beta chloroethylsulfone (7%), bis-beta-chloroethylsulfone and conjugates (8%), and small amounts of cysteine conjugates. Urinary metabolites formed from intraperitoneal injection in rats were bis-cysteinylethylsulfone and thiodiglycol.
Urine, from human volunteers with no known exposure to sulfur mustard, contained detectable but very low concentrations (<0.2ng/mL) of thiodiglycol, consistent with previous observations using different methodologies. Combined concentrations of thiodiglycol and thiodiglycol sulfoxide were determined after reduction of the latter with titanium trichloride. In this case higher background levels (up to 3ng/mL) were observed, consistent with the sulfoxide being the major excretion product of the two metabolites. The method was applied to urine samples, stored frozen for 13 years, from two casualties of accidental mustard poisoning. Levels of thiodiglycol were 1 and 3 ng/mL, which increased to 78 and 104 ng/mL after treatment of the urine with titanium trichloride.
For more Metabolism/Metabolites (Complete) data for Thiodiglycol (7 total), please visit the HSDB record page.
Absorption, Distribution and Excretion
The procedure was applied to urine samples obtained from Iranian patients who were the alleged victims of an attack by chemical warfare agents (probably mustard gas). A number of control samples were investigated as well. Thiodiglycol was found in the urine of the Iranian patients in concentrations varying between 3 and 140 ng/mL. However, the detection of thiodiglycol in concentrations up to 55 ng/mL in control samples excluded the unambiguous verification of the use of mustard gas against the Iranian patients.
The modified procedure was applied to urine samples of several Iranian patients who were victims of an alleged attack with mustard gas and who were treated in European hospitals in 1986. With the exception of one relatively high value (330 ng/mL), the thiodiglycol concentrations were in the same range (10 to 100 ng/mL) as those found during an investigation in 1984. The urine of 20 male controls contained thiodiglycol amounts not above 20 ng/mL. The combined data obtained in 1984 and 1986 (25 Iranian patients and 25 controls) show statistically significant differences. Approximately 80% of the Iranian patients had levels above the 95% confidence limit calculated from the control group.
The purpose of this study was to develop an assay to study the flux of sulfur mustard (HD) through the skin and determine if metabolites are formed due to the epidermal metabolism of HD after topical exposure of the isolated perfused porcine skin flap (IPPSF) to 14C-HD. Four IPPSFs were topically dosed with 2.85 mg of 14C-HD in ethanol. Venous perfusate samples were collected and added to a 34% solution of NaCl and snap-frozen to inhibit the metabolism of HD until time for assay. Perfusate samples were extracted using a solid-phase extraction cartridge with ethyl acetate and then assayed using gas chromatography. Two of the 4 IPPSFs showed detectable levels of HD in the venous perfusate 15 min after dosing, with 1 of these 2 IPPSFs showing detectable levels of HD in the perfusate 2 hours after dosing. All 4 IPPSFS had no more than 3 metabolites of HD appearing in the perfusate throughout the 2 hr experiment, with one of the these metabolites identified as thiodiglycol. These experiments showed that little, if any, HD appears in the venous perfusate intact after percutaneous absorption and that epidermal metabolism of HD does occur to a significant degree in the IPPSF.
90% of an intraperitoneal dose of thiodiglycol in rats was excreted in the urine within 24 hr and by 8 days virtually all of the dose had been excreted. There was no significant excretion in the feces ... Only around 0.5 to 1% of thiodiglycol was excreted unchanged.
Background levels of thiodiglycol in human urine are normally <1 ng/mL ... Others have reported background levels of thiodiglycol to be from 1 to 55 ng/mL ... The source of these background levels is unknown.
Verwendung und Herstellung
Uses
A hydrolysis product of sulfur mustard (chemical weapon); Used as an intermediate for elastomers and antioxidants, a solvent for dyes in textile printing, to make ink for ball-point pens, and a precursor to mustard gas; Also used in the paint, lacquer, and varnish industry; in the polymers industry; and as a fixing agent, process regulator, and stabilizer; [HSDB] Used to make pulp, paper products, furniture, paints, pigments, dyestuffs, varnishes, coatings, and inks; Also used as a solvent for coloring paper, a softener for special rubbers, and possibly as an antioxidant in cosmetics; [OECD SIDS: Thiodiglycol - 2004]
Manufacture and export strictly controlled under the International Chemical Weapons Convention (can be used to make sulfur mustard); [OECD SIDS: Thiodiglycol - 2004]
Pulp and Paper Processing [Category: Industry]
Intermediate for elastomers and antioxidants; solvent for dyes in textile printing.
Thiodiglycol is used as a precursor for sulfur mustard ... It is also an important primary metabolite of sulfur mustard formed by simple hydrolysis.
/SRP: Chemical Weapons Convention/ schedule 2B precursor to mustard gas, sesquimustard, HT, T, and Q.
U.S. Production
2023: 75,000 - <500,000 lb
In 2004, participating countries declared 50.96 metric tons of thiodiglycol and reported that 50.96 metric tons of this Schedule 2 B chemical were destroyed.
This chemical is listed as a High Production Volume (HPV) (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).
Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7137]
Non-confidential 2016 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Ethanol, 2,2'-thiobis-:
Methods of Manufacturing
Prepared from ethylene oxide and hydrogen sulfide.
Hydrolysis of dichloroethyl sulfide, interaction of ethylene chlorohydrin and sodium sulfide.
General Manufacturing Information
Paint and Coating Manufacturing
Ethanol, 2,2'-thiobis-: ACTIVE
Thiodiglycol is a /SRP: Chemical Weapons Convention/ schedule 2B precursor: chemicals, except for those listed in Schedule 1, containing a phosphorus atom to which is bonded one methyl, ethyl, or propyl (normal or iso) group but no further carbon atoms.
/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./ The Convention's monitoring and verification measures involve submission of declarations regarding ... /Schedule 1, 2, and 3 chemicals/ and inspections by the Organization for the Prohibition of Chemical Weapons of the facilities where these chemicals are produced. ... Schedule 2 lists toxic chemicals and precursors deemed to pose a significant risk to the object and purpose of the CWC because of their lethal or incapacitating properties. Precursors may be used in the final stage for formation, or may be important for the production, of any of the chemicals listed in Schedule 1 or toxic chemicals listed in Schedule 2. Schedule 2 chemicals are not produced in large quantities for commercial ... purposes ... but may be used to manufacture such things as insecticides, herbicides, lubricants or pharmaceutical products (2). BZ is listed in the CWC Annex on Chemicals under Schedule 2 (1).
Anwendungen
Verwendenantineoplastic, alkylating agent
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Nachgelagerte Produkte
Ergänzende Hinweise
DefinitionChEBI: A diol that is pentane-1,5-diol in which the methylene group at position 3 is replaced by a sulfur atom
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