Phenyl glycidyl ether

Phenyl glycidyl ether, is a liquid aromatic organic chemical in the glycidyl ether class of compounds.^[2] 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.^[3][4] It is REACH registered and on EINECS under the name 2,3-epoxypropyl phenyl ether.^[5]

Phenyl glycidyl ether

Names
IUPAC name 2-(phenoxymethyl)oxirane
Other names Phenyl glycidyl ether; Phenylglycidyl ether; Phenol glycidyl ether; Phenol-glycidaether; Phenoxypropene oxide; Phenoxypropylene oxide; Phenyl 2,3-epoxypropyl ether; Phenylglycydyl ether; Propane, 1,2-epoxy-3-phenoxy-; Oxirane, 2-(phenoxymethyl)-
Identifiers
CAS Number	122-60-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:82367
ChEMBL	ChEMBL1568222
ChemSpider	28958
ECHA InfoCard	100.004.144
EC Number	204-557-2
KEGG	C19291
PubChem CID	31217
RTECS number	TZ3675000
UNII	44KJQ1655I
UN number	2810
CompTox Dashboard (EPA)	DTXSID8021145
InChI InChI=1S/C9H10O2/c1-2-4-8(5-3-1)10-6-9-7-11-9/h1-5,9H,6-7H2 Key: FQYUMYWMJTYZTK-UHFFFAOYSA-N
SMILES C1C(O1)COC2=CC=CC=C2
Properties
Chemical formula	C9H10O2
Molar mass	150.177 g·mol−1
Melting point	3.5 °C (38.3 °F; 276.6 K)
Boiling point	245 °C (473 °F; 518 K)
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H317, H332, H335, H341, H350, H412
Precautionary statements	P203, P261, P264, P271, P272, P273, P280, P281, P302+P352, P304+P340, P317, P318, P319, P321, P332+P317, P333+P313, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Manufacture

Phenol and epichlorohydrin are reacted in the presence of a base and not a Lewis acid catalyst as normal with glycidyl ethers. A halohydrin is formed. This is followed by washing with sodium hydroxide in dehydrochlorination step. This forms phenyl glycidyl ether. The waste products are water and sodium chloride and excess caustic soda. One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.^[6]

Other names

• phenyl glycidyl ether
• phenol glycidyl ether
• 1,2-Epoxy-3-phenoxypropane
• 1-Phenoxy-2,3-epoxypropane
• 2,3-Epoxy-1-phenoxypropane
• 2,3-Epoxypropyl phenyl ether
• 3-phenoxy-1,2-epoxypropane
• benzene, (2,3-epoxypropoxy)-
• Ether, 2,3-epoxypropyl phenyl
• Glycidyl phenyl ether
• Oxirane, (phenoxymethyl)-
• propane, 1,2-epoxy-3-phenoxy-

^[7]

Uses

It has been used for lowering the viscosity of epoxy resins.^{[8][9][10][11][12]} It undergoes anionic polymerization.^[13] It is one of a number of glycidyl ethers available commercially that are used to reduce the viscosity of epoxy resins.^[14][15] These are then further used in coatings, sealants, adhesives and elastomers.^[16] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[17][18]

Toxicology

It has caused cancer in laboratory animals.^[19] It is also listed as a California Proposition 65 chemical.^[20] It is specifically mentioned by OSHA.^[21][22]

See also

• Epoxide
• Glycidol