C12–C14 alcohol glycidyl ether

C12-C14 alcohol glycidyl ether (AGE) is an organic chemical in the glycidyl ether family.^[2] It is a mixture of mainly 12 and 14 carbon chain alcohols, also called fatty alcohols that have been glycidated. It is an industrial chemical used as a surfactant but primarily for epoxy resin viscosity reduction.^[3] It has the CAS number 68609-97-2 but the IUPAC name is more complex as it is a mixture and is 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane.^[4] Other names include dodecyl and tetradecyl glycidyl ethers and alkyl (C12-C14) glycidyl ether.

C12–C14 alcohol glycidyl ether

n = 10-12
Names
IUPAC name 2-(dodecoxymethyl)oxirane;2-(tetradecoxymethyl)oxirane;2-(tridecoxymethyl)oxirane
Other names Alkyl glycidyl ether
Identifiers
CAS Number	68609-97-2
3D model (JSmol)	Interactive image
ChemSpider	22504671
ECHA InfoCard	100.065.295
PubChem CID	56846565
CompTox Dashboard (EPA)	DTXSID7028774
InChI InChI=1S/C17H34O2.C16H32O2.C15H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18-15-17-16-19-17;1-2-3-4-5-6-7-8-9-10-11-12-13-17-14-16-15-18-16;1-2-3-4-5-6-7-8-9-10-11-12-16-13-15-14-17-15/h17H,2-16H2,1H3;16H,2-15H2,1H3;15H,2-14H2,1H3 Key: CKNWGKWITWNVEY-UHFFFAOYSA-N
SMILES CCCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCCOCC1CO1.CCCCCCCCCCCCOCC1CO1
Properties
Chemical formula	C48H96O6
Molar mass	769.3 g/mol
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H317
Precautionary statements	P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Manufacture

A fatty alcohol mixture rich in C12-C14 alcohols is placed in a reactor with a Lewis acid catalyst. Then epichlorohydrin is added slowly to control exotherm which results in the formation of the halohydrins.^[5] This is followed by a caustic dehydrochlorination, to form C12-C14 alcohol glycidyl ether.^[6] The waste products are water and sodium chloride and excess caustic soda.^[7] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

As an epoxy modifier it is classed as an epoxy reactive diluent.^[8] It is one of a family of glycidyl ethers available used for viscosity reduction of epoxy resins.^[9] These are then further formulated into coatings, sealants, adhesives, and elastomers.^[10][11] Resins with this diluent tend to show improved workability.^[12] It is also used to synthesize other molecules.^[13][14] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[15][16]

Toxicology

The toxicology is well known, and it is classed as a skin irritant.^[17]

See also

• Epoxide
• Glycidol