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Ethylene glycol

Ethylene glycol
Wireframe model of ethylene glycol
Spacefill model of ethylene glycol
Ball and stick model of ethylene glycol
Sample of ethylene glycol
Names
Preferred IUPAC name
Ethane-1,2-diol
Other names
Ethylene glycol
1,2-Ethanediol
Ethylene alcohol
Hypodicarbonous acid
Monoethylene glycol
1,2-Dihydroxyethane
Identifiers
107-21-1 YesY
3D model (Jmol) Interactive image
3DMet B00278
Abbreviations MEG
505945
ChEBI CHEBI:30742 YesY
ChEMBL ChEMBL457299 YesY
ChemSpider 13835235 YesY
ECHA InfoCard 100.003.159
EC Number 203-473-3
943
KEGG C01380 N
MeSH Ethylene+glycol
PubChem 174
RTECS number KW2975000
UNII FC72KVT52F YesY
Properties
C2H6O2
Molar mass 62.07 g·mol−1
Appearance Clear, colorless liquid
Odor Odorless
Density 1.1132 g/cm3
Melting point −12.9 °C (8.8 °F; 260.2 K)
Boiling point 197.3 °C (387.1 °F; 470.4 K)
Miscible
Solubility Soluble in most organic solvents
Vapor pressure 0.06 mmHg (20 °C)
Viscosity 1.61 × 10−2 N*s / m2
Hazards
Main hazards Harmful
Safety data sheet See: data page
External MSDS
Harmful (Xn)
R-phrases R22 R36
S-phrases S26 S36 S37 S39 S45 S53
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 111 °C (232 °F; 384 K) closed cup
410 °C (770 °F; 683 K)
Explosive limits 3.2%-15.2%
US health exposure limits (NIOSH):
PEL (Permissible)
None
REL (Recommended)
None established
IDLH (Immediate danger)
None
Related compounds
Related diols
Propylene glycol
Diethylene glycol
Triethylene glycol
Polyethylene glycol
Supplementary data page
Refractive index (n),
Dielectric constantr), etc.
Thermodynamic
data
Phase behaviour
solid–liquid–gas
UV, IR, NMR, MS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound with the formula (CH2OH)2. It is mainly used for two purposes, as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, sweet-tasting syrup. Ethylene glycol is moderately toxic.

Ethylene glycol is produced from ethylene (ethene), via the intermediate ethylene oxide. Ethylene oxide reacts with water to produce ethylene glycol according to the chemical equation:

This reaction can be catalyzed by either acids or bases, or can occur at neutral pH under elevated temperatures. The highest yields of ethylene glycol occur at acidic or neutral pH with a large excess of water. Under these conditions, ethylene glycol yields of 90% can be achieved. The major byproducts are the ethylene glycol oligomers diethylene glycol, triethylene glycol, and tetraethylene glycol. About 6.7 billion kilograms are produced annually.

A higher selectivity is achieved by use of Shell's OMEGA process. In the OMEGA process, the ethylene oxide is first converted with carbon dioxide (CO2) to ethylene carbonate to then react with water in a second step to selectively produce mono-ethylene glycol. The carbon dioxide is released in this step again and can be fed back into the process circuit. The carbon dioxide comes in part from the ethylene oxide production, where a part of the ethylene is completely oxidized.


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