Thiodiglycol, or bis(2-hydroxyethyl)sulfide (also known as 2,2-thiodiethanol or TDE), is the organosulfur compound with the formula S(CH₂CH₂OH)₂. It is miscible with

water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...

and polar

organic solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

s. It is a colorless liquid. It is structurally similar to

diethylene glycol Diethylene glycol (DEG) is an organic compound with the formula (HOCH2CH2)2O. It is a colorless, practically odorless, and hygroscopic liquid with a sweetish taste. It is a four carbon dimer of ethylene glycol. It is miscible in water, alcohol, ...

. Thiodiglycol is manufactured by reaction of

2-chloroethanol 2-Chloroethanol (also called ethylene chlorohydrin or glycol chlorohydrin) is an organic chemical compound with the chemical formula HOCH2CH2Cl and the ''simplest'' beta-halohydrin (chlorohydrin). This colorless liquid has a pleasant ether-like od ...

with sodium sulfide. Thiodiglycol has both polar and nonpolar solvent properties. It is used as a

solvent A solvent (s) (from the Latin '' solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for ...

in a variety of applications ranging from dyeing

textile Textile is an umbrella term that includes various fiber-based materials, including fibers, yarns, filaments, threads, different fabric types, etc. At first, the word "textiles" only referred to woven fabrics. However, weaving is not the ...

s to

ink Ink is a gel, sol, or solution that contains at least one colorant, such as a dye or pigment, and is used to color a surface to produce an image, text, or design. Ink is used for drawing or writing with a pen, brush, reed pen, or quill. Thicker ...

s in some

ballpoint pen A ballpoint pen, also known as a biro (British English), ball pen (Hong Kong, Indian and Philippine English), or dot pen (Nepali) is a pen that dispenses ink (usually in paste form) over a metal ball at its point, i.e. over a "ball point". ...

s. In chemical synthesis, it is used as a building block for protection products, dispersants,

fiber Fiber or fibre (from la, fibra, links=no) is a natural or artificial substance that is significantly longer than it is wide. Fibers are often used in the manufacture of other materials. The strongest engineering materials often incorporate ...

plasticizer A plasticizer ( UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity, to decrease its viscosity, and/or to decrease friction during its handling in manufacture. Plasticiz ...

rubber accelerator Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Thailand, Malaysia, and ...

pesticide Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampri ...

s, dyes, and various other organic chemicals. In the manufacture of

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

s, it is used as a

chain transfer agent Chain transfer is a polymerization reaction by which the activity of a growing polymer chain is transferred to another molecule. :P• + XR' → PX + R'• Chain transfer reactions reduce the average molecular weight of the final polymer. Chain ...

. As an

antioxidant Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricant ...

, it is used as an additive in

lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, t ...

s. Thiodiglycol is used as a

mounting medium A microscope slide is a thin flat piece of glass, typically 75 by 26 mm (3 by 1 inches) and about 1 mm thick, used to hold objects for examination under a microscope. Typically the object is mounted (secured) on the slide, and then b ...

in microscopy. The ability to vary the

refractive index In optics, the refractive index (or refraction index) of an optical medium is a dimensionless number that gives the indication of the light bending ability of that medium. The refractive index determines how much the path of light is bent, or ...

of the medium by varying the concentration of TDE in an aqueous solution, plus its relative lack of toxicity makes it highly desirable for such use. The refractive index of the solution can be varied anywhere from near that of water (1.333) to that of glass (1.518). Thiodiglycol is a Chemical Weapons Convention schedule 2 chemical used in the production of sulfur-based mustard gases. Thiodiglycol is also a product of the

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

of the "mustard gas"

bis(2-chloroethyl)sulfide Bis(2-chloroethyl)sulfide is the organosulfur compound with the formula . It is a prominent member of a family of cytotoxic and blister agents known as mustard agents. Sometimes referred to as '' mustard gas'', the term is technically incorrec ...

and can be detected in the

urine Urine is a liquid by-product of metabolism in humans and in many other animals. Urine flows from the kidneys through the ureters to the urinary bladder. Urination results in urine being excretion, excreted from the body through the urethra. Cel ...

of casualties.

References

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External links

Blister agent degradation product/precursor: Thiodiglycol

Solvents Thioethers Diols