Thiodiglycol

Last updated
Thiodiglycol
2,2'-thiodiethanol 200.svg
Thiodiglycol-3D-vdW.png
Names
IUPAC name
2-(2-Hydroxyethylsulfanyl)ethanol
Other names
2,2'-Thiodiethanol
β,β'-dihydroxydiethyl sulfide
β-thiodiglycol
thiodiethylene glycol
β-hydroxyethyl sulfide
2-hydroxyethyl sulfide
bis(2-hydroxyethyl) sulfide
bis(β-hydroxyethyl) sulfide
Glyecine A
Kromfax Solvent
Tedegyl
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.523 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2 Yes check.svgY
    Key: YODZTKMDCQEPHD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H10O2S/c5-1-3-7-4-2-6/h5-6H,1-4H2
    Key: YODZTKMDCQEPHD-UHFFFAOYAC
  • OCCSCCO
Properties
C4H10O2S
Molar mass 122.18 g·mol−1
Appearancecolorless liquid
Melting point −16 °C (3 °F; 257 K)
Boiling point 165 °C (329 °F; 438 K) at 14 mmHg (1.9 kPa) or decomposition at 282 °C at normal pressure
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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 and polar organic solvents. It is a colorless liquid. It is structurally similar to diethylene glycol.

Thiodiglycol is manufactured by reaction of 2-chloroethanol with sodium sulfide. [1]

Thiodiglycol is a polar protic solvent. It is used as a solvent in a variety of applications ranging from dyeing textiles to inks in some ballpoint pens. In chemical synthesis, it is used as a building block for protection products, dispersants, fibers, plasticizers, rubber accelerators, pesticides, dyes, and various other organic chemicals. In the manufacture of polymers, it is used as a chain transfer agent. As an antioxidant, it is used as an additive in lubricants.

Thiodiglycol is used as a mounting medium in microscopy. The ability to vary the refractive index 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). [2]

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 of the "mustard gas" bis(2-chloroethyl)sulfide and can be detected in the urine of casualties.

Related Research Articles

<span class="mw-page-title-main">Dye</span> Soluble chemical substance or natural material which can impart color to other materials

A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution and may require a mordant to improve the fastness of the dye on the fiber.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent 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 polar molecules and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent.

<span class="mw-page-title-main">Dimethyl sulfoxide</span> Organosulfur chemical compound used as a solvent

Dimethyl sulfoxide (DMSO) is an organosulfur compound with the formula (CH3)2SO. This colorless liquid is the sulfoxide most widely used commercially. It is an important polar aprotic solvent that dissolves both polar and nonpolar compounds and is miscible in a wide range of organic solvents as well as water. It has a relatively high boiling point. DMSO has the unusual property that many individuals perceive a garlic-like taste in the mouth after DMSO makes contact with their skin.

<span class="mw-page-title-main">Sodium acetate</span> Chemical compound

Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

<span class="mw-page-title-main">Polysulfide</span>

Polysulfides are a class of chemical compounds containing chains of sulfur atoms. There are two main classes of polysulfides: inorganic and organic. Among the inorganic polysulfides, there are ones which contain anions, which have the general formula S2−
n
. These anions are the conjugate bases of the hydrogen polysulfides H2Sn. Organic polysulfides generally have the formulae R1SnR2, where R = alkyl or aryl.

<span class="mw-page-title-main">Industrial wastewater treatment</span> Processes used for treating wastewater that is produced by industries as an undesirable by-product

Industrial wastewater treatment describes the processes used for treating wastewater that is produced by industries as an undesirable by-product. After treatment, the treated industrial wastewater may be reused or released to a sanitary sewer or to a surface water in the environment. Some industrial facilities generate wastewater that can be treated in sewage treatment plants. Most industrial processes, such as petroleum refineries, chemical and petrochemical plants have their own specialized facilities to treat their wastewaters so that the pollutant concentrations in the treated wastewater comply with the regulations regarding disposal of wastewaters into sewers or into rivers, lakes or oceans. This applies to industries that generate wastewater with high concentrations of organic matter, toxic pollutants or nutrients such as ammonia. Some industries install a pre-treatment system to remove some pollutants, and then discharge the partially treated wastewater to the municipal sewer system.

<span class="mw-page-title-main">Aluminium sulfate</span> Chemical compound

Aluminium sulfate is a salt with the formula Al2(SO4)3. It is soluble in water and is mainly used as a coagulating agent (promoting particle collision by neutralizing charge) in the purification of drinking water and wastewater treatment plants, and also in paper manufacturing.

<span class="mw-page-title-main">Thioglycolic acid</span> Chemical compound

Thioglycolic acid (TGA) is the organic compound HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a thiol (mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly unpleasant odor. TGA is miscible with polar organic solvents.

<span class="mw-page-title-main">Sodium sulfide</span> Chemical compound

Sodium sulfide is a chemical compound with the formula Na2S, or more commonly its hydrate Na2S·9H2O. Both the anhydrous and the hydrated salts in pure crystalline form are colorless solids, although technical grades of sodium sulfide are generally yellow to brick red owing to the presence of polysulfides and commonly supplied as a crystalline mass, in flake form, or as a fused solid. They are water-soluble, giving strongly alkaline solutions. When exposed to moist air, Na2S and its hydrates emit hydrogen sulfide, an extremely toxic, flammable and corrosive gas which smells like rotten eggs.

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 odor. It is miscible with water. The molecule is bifunctional, consisting of both an alkyl chloride and an alcohol functional group.

<i>N</i>-Methyl-2-pyrrolidone Chemical compound

N-Methyl-2-pyrrolidone (NMP) is an organic compound consisting of a 5-membered lactam. It is a colorless liquid, although impure samples can appear yellow. It is miscible with water and with most common organic solvents. It also belongs to the class of dipolar aprotic solvents such as dimethylformamide and dimethyl sulfoxide. It is used in the petrochemical, polymer and battery industries as a solvent, exploiting its nonvolatility and ability to dissolve diverse materials.

Chloroalkyl ethers are a class of organic compounds with the general structure R-O-(CH2)n-Cl, characterized as an ether connected to a chloromethyl group via an alkane chain.

<span class="mw-page-title-main">Cleaning agent</span> Substance used to remove dirt or other contaminants

Cleaning agents or hard-surface cleaners are substances used to remove dirt, including dust, stains, foul odors, and clutter on surfaces. Purposes of cleaning agents include health, beauty, removing offensive odor, and avoiding the spread of dirt and contaminants to oneself and others. Some cleaning agents can kill bacteria and clean at the same time. Others, called degreasers, contain organic solvents to help dissolve oils and fats.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether.

Wet Processing Engineering is one of the major streams in Textile Engineering or Textile manufacturing which refers to the engineering of textile chemical processes and associated applied science. The other three streams in textile engineering are yarn engineering, fabric engineering, and apparel engineering. The processes of this stream are involved or carried out in an aqueous stage. Hence, it is called a wet process which usually covers pre-treatment, dyeing, printing, and finishing.

Green textiles are fabrics or fibres produced to replace environmentally harmful textiles and minimise the ecological impact. Green textiles are part of the sustainable fashion and eco-friendly trends, providing alternatives to the otherwise pollution-heavy products of conventional textile industry, which is deemed the most ecologically damaging industry.

Bis(2-chloroethyl)sulfide is the organosulfur compound with the formula (ClCH2CH2)2S. 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 incorrect: bis(2-chloroethyl)sulfide is a liquid at room temperature. In warfare it was dispersed in the form of a fine mist of liquid droplets.

References

  1. E. M. Faber and G. E. Miller (1932). "β-Thiodiglycol". Organic Syntheses. 12: 68. doi:10.15227/orgsyn.012.0068.
  2. Staudt T; et al. (2006). "2,2′-Thiodiethanol: A new water soluble mounting medium for high resolution optical microscopy". Microscopy Research and Technique. 70: 1–9. doi:10.1002/jemt.20396. PMID   17131355. S2CID   13553493.