Diglycidyl ether

Last updated
Diglycidyl ether
Diglycidyl ether.svg
Names
Preferred IUPAC name
2,2′-[Oxybis(methylene)]bis(oxirane)
Other names
Glycidyl ether; Bis-(2,3-epoxypropyl)ether; Diallyl ether dioxide; Diepoxy propyl ether, DGE, 2-Epoxypropyl ether
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.094 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 218-802-6
PubChem CID
RTECS number
  • KN2350000
UNII
UN number 2922
  • InChI=1S/C6H10O3/c1(5-3-8-5)7-2-6-4-9-6/h5-6H,1-4H2
    Key: GYZLOYUZLJXAJU-UHFFFAOYSA-N
  • InChI=1/C6H10O3/c1(5-3-8-5)7-2-6-4-9-6/h5-6H,1-4H2
    Key: GYZLOYUZLJXAJU-UHFFFAOYAO
  • O1CC1COCC2OC2
Properties
C6H10O3
Molar mass 130.143 g·mol−1
Appearancecolorless liquid [1]
Odor strong, irritating [1]
Density 1.12 g/mL [1]
Boiling point 260 °C; 500 °F; 533 K [1]
Vapor pressure 0.09 mmHg (25°C) [1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
carcinogen
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg
Danger
H302, H311, H314, H315, H317, H330
P260, P261, P264, P270, P271, P272, P280, P284, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P403+P233, P405, P501
Flash point 64 °C; 147 °F; 337 K [1]
Lethal dose or concentration (LD, LC):
30 ppm (mouse, 4 hr)
86 ppm (mouse, 4 hr)
30 ppm (mouse, 8 hr)
200 ppm (rat, 4 hr)
68 ppm (rat, 8 hr) [2]
NIOSH (US health exposure limits):
PEL (Permissible)
C 0.5 ppm (2.8 mg/m3) [1]
REL (Recommended)
Ca TWA 0.1 ppm (0.5 mg/m3) [1]
IDLH (Immediate danger)
Ca [10 ppm] [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diglycidyl ethers are chemical compounds used as a reactive diluents for epoxy resin. Other uses include treating textiles and stabilizing chlorinated organic compounds. Diglycidyl ether itself is extremely toxic, and can prove fatal or cause permanent damage if inhaled or consumed orally. As a class of compounds, there are a number of them available commercially with much lower toxicity profiles. [3] [4] One such example is epoxy resin itself Bisphenol A diglycidyl ether.

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3
H
8
O
2
that is used mainly as a solvent. It is a clear, colorless liquid with an ether-like odor. It is in a class of solvents known as glycol ethers which are notable for their ability to dissolve a variety of different types of chemical compounds and for their miscibility with water and other solvents. It can be formed by the nucleophilic attack of methanol on protonated ethylene oxide followed by proton transfer:

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<span class="mw-page-title-main">Bisphenol A diglycidyl ether</span> Chemical compound

Bisphenol A diglycidyl ether is an organic compound and is a liquid epoxy resin. The compound is a colorless viscous liquid. It is a key component of many epoxy resin formulations. Addition of further Bisphenol A and a catalyst and heat can produce Bisphenol A glycidyl ether epoxy resins of higher molecular weight that are solid.

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<i>m</i>-Xylylenediamine Chemical compound

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n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

1,4-Butanediol diglycidyl ether (B14DODGE) is an organic chemical in the glycidyl ether family. It is aliphatic and a colorless liquid. It has two epoxide (oxirane) groups per molecule. Its main use is in modifying epoxy resins especially viscosity reduction.

<span class="mw-page-title-main">Diglycidyl resorcinol ether</span> Chemical compound

Diglycidyl resorcinol ether, also called Resorcinol diglycidyl ether (RDGE) is a liquid aromatic organic chemical compound and chemically a glycidyl ether.

<span class="mw-page-title-main">Phenyl glycidyl ether</span> Chemical compound

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds. It has the formula C9H10O2. It has the CAS Registry Number 122-60-1 and the IUPAC name of 2-(phenoxymethyl)oxirane. A key use is in the viscosity reduction of epoxy resin systems. It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.

References

  1. 1 2 3 4 5 6 7 8 9 NIOSH Pocket Guide to Chemical Hazards. "#0215". National Institute for Occupational Safety and Health (NIOSH).
  2. "Diglycidyl ether". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  3. "Poly(ethylene glycol) diglycidyl ether (PEGDGE 600)". www.polysciences.com. Retrieved 2020-05-01.
  4. Berdasco, Nancy Anne M.; Waechter, John M. (2012), "Epoxy Compounds: Aromatic Diglycidyl Ethers, Polyglycidyl Ethers, Glycidyl Esters, and Miscellaneous Epoxy Compounds", Patty's Toxicology, American Cancer Society, pp. 491–528, doi:10.1002/0471435139.tox083.pub2, ISBN   978-0-471-12547-1 , retrieved 2020-05-01