Thiodiglycol

122.18600

122.19

203-874-3

9BW5T43J04

1601

758456|6289

DTXSID6026878

C75295

Liquid|Syrupy, colorless, liquid

2930909026

65.76000

-0.29580

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.

1.1819 g/cm³ @ Temp: 20 °C

-10.2 °C

282 °C

>230 °F

1.519-1.521

alcohol: miscible(lit.);Solubility in water, g/100ml at 20°C: 100

Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool

0.047mmHg at 25°C

Relative vapour density (air = 1): 4.22

vol% in air: 1.2.2

Characteristic odor

Henry's Law constant = 1.9X10-9 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 2.8X10-11 cu cm/molecule-sec at 25 °C (est)

No rapid reaction with air. No rapid reaction with water.

Alcohols and Polyols

568 °F (298 °C)|260 °C

UN1230 - class 3 - PG 2 - Methanol, solution

1

R36

S23; S26; S36/37/39; S45

KM2975000

Xi

See Chemical Dangers.

Stable. Incompatible with strong oxidizing agents. Reacts with a wide variety of compounds. Flammable.

P210-P260-P280-P301 + P310-P311

H225-H301 + H311 + H331-H370

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.

Reacts violently with strong acids and strong oxidants. This produces hydrogen sulfide.|Reacts violently with acetone + sodium peroxide. Can react with oxidizing materials.|Do not use with hydrochloric acid.|Thiodiglycol was being oxidized with an excess of hydrogen peroxide using acetone as a solvent. At the conclusion the acetone and excess hydrogen peroxide were removed under vacuum in a steam bath. After about 15 minutes of heating on a steam bath, a violent explosion occurred.|Reacts violently with acetone and sodium peroxide.

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/]

Combustible.

|Warning|H319: Causes serious eye irritation [Warning Serious eye damage/eye irritation]|P264, P280, P305+P351+P338, and P337+P313|H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]|Aggregated GHS information provided by 334 companies from 2 notifications to the ECHA C&L Inventory.|H335: May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]|P261, P271, P304+P340, P312, P403+P233, P405, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: Where risk assessment shows air-purifying respirators are appropriate use a full-face respirator with multipurpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Combustible when exposed to heat or flame.|Combustible.

Explosive limits , vol% in air: 1.2-5.2

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.

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.

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.

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.

A skin and eye irritant.|The substance is mildly irritating to the eyes and the respiratory tract.

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.

See Chemical Dangers.

Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly on spraying.

The substance is mildly irritating to the eyes and respiratory tract.

NO open flames.

Use ventilation, local exhaust or breathing protection.

Protective gloves.

Wear safety goggles.

| 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.

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).

Thiodiglycol is listed as an ingredient in home use printer ink cartridges(1). Thiodiglycol was detected at <10-55,000 ug/mL in old ton containers (high-strength, sealed steel barrels) of chemical weapons (sulfur mustard) stored on Johnston Atoll since 1971(2).

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.

LD50 Rat oral 6610 mg/kg|LD50 Rat sc 4000 mg/kg|LD50 Mouse sc 4000 mg/kg|LD50 Rabbit iv 3000 mg/kg|For more Non-Human Toxicity Values (Complete) data for Thiodiglycol (6 total), please visit the HSDB record page.

/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.

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).

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).

The rate constant for the vapor-phase reaction of thiodiglycol with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Thiodiglycol does not contain chromophores that absorb at wavelengths >290 nm(2) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC). Thiodiglycol did not undergo hydrolysis at pH 4, 7 or 11(3). Thiodiglycol did not undergo photolysis in aqueous solution after irradiation by sunlight for 14 days(3).

An estimated BCF of 3 was calculated in fish for thiodiglycol(SRC), using a log Kow of -0.63(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.

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#7146]

The Henry's Law constant for thiodiglycol is estimated as 1.9X10-9 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that thiodiglycol is expected to be essentially nonvolatile from water and moist soil surfaces(2). Thiodiglycol is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 5.09X10-4 mm Hg(3).

According to the 2016 TSCA Inventory Update Reporting data, 3 reporting facilities estimate the number of persons reasonably likely to be exposed in the manufacturing, processing, or use of thiodiglycol in the United States may be as low as 10-25 workers up to the range of 100-500 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).|NIOSH (NOES Survey 1974) has statistically estimated that 5259 workers were potentially exposed to thiodiglycol in the US(1). Occupational exposure to thiodiglycol may occur through inhalation and dermal contact with this compound at workplaces where thiodiglycol is produced or used(SRC). Because thiodiglycol is a hydrolysis product of the chemical weapon sulfur mustard(2), decontamination workers or individuals in an area that experienced a sulfur mustard attack maybe be exposed to residual thiodiglycol(SRC).|Thiodiglycol was found in decontamination wastes from chemical weapons agents(1). Thiodiglycol is a hydrolysis product of the chemical weapon sulfur mustard(2). Occupational exposure to thiodiglycol may occur during decontamination procedures at sites where chemical weapons are stored(SRC).|Thiodiglycol was identified in the dichloromethane extracts of samples of soil collected in November 1989 from a site of chemical warfare incident involving sulfur mustard in Iraq close to the borders of Turkey and Iran(1). Individuals in an area that experienced a sulfur mustard attack maybe be exposed to thiodiglycol(SRC).

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

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.

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.

The apparent half-life of thiodiglycol in the urine of rats after cutaneous application of sulfur mustard is 2.4 days

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.

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.

Treatment with ethanol will compete with thiodiglycol for the enzyme alcohol dehydrogenase and can slow down the formation of acidic metabolites. ... This may be administered orally or intravenously.|No data available about treatment of thiodiglycol exposure. The chemical structure of thiodiglycol is similar to that of ethylene glycol (1,2-ethanediol) (HO-CH2-CH2-OH) ... in that both compounds contain ethanol groups. Both compounds are substrates for the alcohol dehydrogenase enzyme and both compounds forms acidic metabolites ... Based on this information it would be relevant to look at the main treatment options for ethylene glycol.|Life supportive procedures and symptomatic/specific treatment: Make a proper assessment of airway, breathing, circulation and neurological status of the patient. Adminster oxygen. Monitor vital signs. Monitor acid-base balance.|... Neither lavage nor ipecac should be used ... Activated charcoal poorly absorbs alcohol, it is probably not indicated for thiodiglycol intoxication..|For more Antidote and Emergency Treatment (Complete) data for Thiodiglycol (8 total), please visit the HSDB record page.

/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)]

2,2'-sulfobisethanol

Cough. Nausea.

Redness. Pain.

All other basic organic chemical 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).

A novel method based on CE with precolumn derivatization and direct UV detection for the determination of thiodiglycol (TDG), TDG sulfoxide, and TDG sulfone in water samples was developed. The lack of a UV chromophore of target analytes was overcome by derivatization with phthalic anhydride. The reactant concentrations, as well as the derivatization dependence on heating temperature and time, were carefully investigated. The baseline separation of three derivatives was achieved in less than 8 min by applying a simple BGE composed of a 30 mM borate buffer at pH 8.5. Several parameters affecting the separation efficiency (buffer pH and concentration, capillary temperature, and applied voltage) were evaluated. Calibration curves of all compounds showed good linear correlations (R(2) > 0.9994). The LODs of the TDG and its oxidation products were in the range of 98-154 ng/mL. The precision tests resulted in RSDs for migration times and peak areas of less than 1.2 and 3.6%, respectively. The developed method was successfully applied for the analysis of TDG and oxidation products in seawater, utilizing the carbon aerogel-based adsorbents for sample purification and concentration. Additionally, the method has the potential to be transformed into a portable CE format.|An LC-UV-SPE NMR method for the analysis of polar hydrolysis products of the chemical warfare agents known as sulfur mustards at low ppm levels in environmental samples is developed. The hydrolysis products thiodiglycol (I), bis(2-hydroxyethylthio)methane (II), 1,2-bis(2-hydroxyethylthio)ethane (III), 1,3-bis(2-hydroxyethylthio)propane (IV), 1,4-bis(2-hydroxyethylthio)butane (V), 1,5-bis(2-hydroxyethylthio)pentane (VI), bis(2-hydroxymethylthioethyl)ether (VII) and bis(2-hydroxyethylthioethyl)ether (VIII) are baseline separated within 11 min by the LC gradient program and trapped post-column on SPE cartridges. After elution in 2 mm o.d. NMR tubes (1)H NMR spectra were recorded. Recoveries vary from 43 +/- 5 for I to 102 +/- 5% for VI and are limited by volume breakthrough. The detection limits of the LC-SPE NMR method vary between 200 ng for V and 450 ng for I. Increasing the injection volume is shown to be more effective than multiple trapping for the analytes I-VIII to increase the amount of material trapped on the SPE cartridges. The applicability of the developed method to the analysis of environmental samples was tested by the analysis of sample 293 provided by the 29th Official OPCW (Organization for the Prohibition of Chemical Weapons) Proficiency Test. The chromatographic and (1)H NMR data obtained by the method are highly reproducible and provide acceptable data for the identification of chemicals related to CWC (Chemical Weapons Convention) in case an off-site analysis for the verification of the CWC or OPCW Proficiency Tests according to the OPCW criteria for the acceptance of chromatographic and (1)H NMR spectral data.|Sulfur mustard (HD), bis(2-chloroethyl)sulfide, is one of a class of mustard agents which are chemical warfare agents. The main chemical warfare hydrolysis degradation products of sulfur mustards are: thiodiglycol, bis(2-hydroxyethylthio)methane, 1,2-bis(2-hydroxyethylthio)ethane, 1,3-bis(2-hydroxyethylthio)propane, and 1,4-bis(2-hydroxyethylthio)butane. The aim of this study is to identify these five hydrolysis degradation products utilizing reversed-phase high-performance liquid chromatography coupled with inductively coupled plasma mass spectrometry (ICP-MS) for element-specific sulfur detection using a collision/reaction cell and electrospray ionization mass spectrometry to confirm the identification. To date, this is the first study utilizing ICP-MS with (32)S element-specific detection for the analysis of vesicant chemical warfare agent degradation products.|A method for determining thiodiglycol (TDG), a mustard gas hydrolysis product in water, serum and urine samples using gas chromatography-mass spectrometry (GC-MS) after tert-butyldimethylsilylation (TBDMS) is described. Quantitation of TDG was performed by measuring the respective peak area on the extracted ion chromatogram of m/z 293, using an internal standard, the TDG homologue, thiodipropanol, peak area of which was measured as m/z 321. The presence of salts in the sample solution not only suppressed the loss of TDG by vaporization during the evaporation of water, but also facilitated the rate of production of di-silylated derivative, bis(tert-butyldimethylsilyoxylethyl)sulfide (TDG-(TBDMS)2). Under the pretreatment conditions used, in which 0.5 mL of water sample supplemented with 100 uM potassium chloride was evaporated to dryness under reduced pressure, followed by reaction with N-methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide at 60 degrees C for 1 hr, TDG-(TBDMS)2 was reproducibly detected with about a 55% recovery and a limit of detection (LOD, scan mode, S/N = 3) of 5.4 ng/mL. TDG was also determined by GC-MS from a 0.5 mL serum sample (after perchloric acid deproteinization) and from a 0.1 mL urine sample, after TBDMS derivatization. The LOD was determined to be 7.0 and 110 ng/mL for serum and urine, respectively.|For more Analytic Laboratory Methods (Complete) data for Thiodiglycol (7 total), please visit the HSDB record page.

Four HD urinary metabolites including hydrolysis metabolite thiodiglycol (TDG), glutathione-derived metabolite 1,1'-sulfonylbis[2-S-(N-acetylcysteinyl)ethane] (SBSNAE), as well as the beta-lyase metabolites 1,1'-sulfonylbis[2-(methylsulfinyl)ethane] (SBMSE) and 1-methylsulfinyl-2-[2-(methylthio) ethylsulfonyl]ethane (MSMTESE) are considered as important biomarkers for short-term retrospective detection of HD exposure. In this study, a single method for simultaneous quantification of the four HD metabolites in urine samples was developed using ultra high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). The four urinary metabolites were simultaneously extracted from urinary samples using a solid phase extraction (SPE) method with high extraction recoveries for all four metabolites varied in the range of 71.1-103% followed by UHPLC-MS/MS analysis. The SPE is simple and high effective only requiring 0.1 mL of urinary samples and 0.5 hr time consuming. The problem of previous co-elution of TDG and SBSNAE in UHPLC was well solved, and complete separation of TDG, SBSNAE, SBMSE and MSMTESE from SPE-processed urine matrix was obtained to increase specificity and sensitivity. A full method validation was performed for each analyte in urine matrix. The linear range of calibration curves for the four analytes were respectively from 0.50-500 ng/mL for TDG and SBSNAE, 0.05-500 ng/mL for SBMSE and MSMTESE with coefficient of determination value (R2) >/= 0.990. The limit of detection was 0.25 ng/mL for TDG and SBSNAE, 0.01 ng/mL for SBMSE and MSMTESE spiked in normal urine. The intra/inter-day precision for each analyte at three QC levels had relative standard deviation (%RSD) of

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