Diethylene glycol

Diethylene glycol

Names
Preferred IUPAC name 2,2'-Oxydi(ethan-1-ol)
Other names 2,2'-Oxybis(ethan-1-ol) 2-(2-Hydroxyethoxy)ethan-1-ol Diethylene glycol Ethylene diglycol Diglycol 2,2'-Oxybisethanol 2,2'-Oxydiethanol 3-Oxa-1,5-pentanediol Dihydroxy diethyl ether
Identifiers
CAS Number	111-46-6 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:46807 Y
ChemSpider	13835180 Y
ECHA InfoCard	100.003.521
KEGG	C14689 Y
PubChem CID	8117
UNII	61BR964293 Y
InChI InChI=1S/C4H10O3/c5-1-3-7-4-2-6/h5-6H,1-4H2 Y Key: MTHSVFCYNBDYFN-UHFFFAOYSA-N Y InChI=1/C4H10O3/c5-1-3-7-4-2-6/h5-6H,1-4H2 Key: MTHSVFCYNBDYFN-UHFFFAOYAK
SMILES C(COCCO)O
Properties
Chemical formula	C4H10O3
Molar mass	106.12 g/mol
Appearance	Colorless liquid
Density	1.118 g/mL
Melting point	−10.45 °C (13.19 °F; 262.70 K)
Boiling point	244 to 245 °C (471 to 473 °F; 517 to 518 K)
Solubility in water	miscible
Hazards
Main hazards	Toxic
Safety data sheet	Diethylene-glycol MSDS
NFPA 704	1 3 0
Related compounds
Related diols	ethylene glycol, triethylene glycol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Diethylene glycol (DEG) is an organic compound with the formula (HOCH₂CH₂)₂O. It is a colorless, practically odorless, poisonous, and hygroscopic liquid with a sweetish taste. It is miscible in water, alcohol, ether, acetone, and ethylene glycol. DEG is a widely used solvent. It can be a contaminant in consumer products; this has resulted in numerous epidemics of poisoning since the early 20th century.

DEG is produced by the partial hydrolysis of ethylene oxide. Depending on the conditions, varying amounts of DEG and related glycols are produced. The resulting product is two ethylene glycol molecules joined by an ether bond.

"Diethylene glycol is derived as a co-product with ethylene glycol (MEG) and triethylene glycol. The industry generally operates to maximize MEG production. Ethylene glycol is by far the largest volume of the glycol products in a variety of applications. Availability of DEG will depend on demand for derivatives of the primary product, ethylene glycol, rather than on DEG market requirements."

Diethylene glycol is one of several glycols derived from ethylene oxide. Glycols related to and coproduced with diethylene glycol and have the formula HOCH₂CH₂(OCH₂CH₂)_nOH are:

These compounds are all hydrophilic, more so than most diols, by virtue of the ether functionality.

Diethylene glycol is used in the manufacture of unsaturated polyester resins, polyurethanes, and plasticizers. DEG is used as a building block in organic synthesis, e.g. of morpholine and 1,4-dioxane. It is a solvent for nitrocellulose, resins, dyes, oils, and other organic compounds. It is a humectant for tobacco, cork, printing ink, and glue. It is also a component in brake fluid, lubricants, wallpaper strippers, artificial fog solutions, and heating/cooking fuel. In personal care products (e.g. skin cream and lotions, deodorants), DEG is often replaced by selected diethylene glycol ethers. A dilute solution of diethylene glycol can also be used as a cryoprotectant; however, ethylene glycol is much more commonly used. Most ethylene glycol antifreeze contains a few percent diethylene glycol, present as an byproduct of ethylene glycol production.