1,4-Butanediol diglycidyl ether

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.^[1] Its main use is in modifying epoxy resins especially viscosity reduction.^[2]

1,4-Butanediol diglycidyl ether

Names
IUPAC name 2-[4-(Oxiran-2-ylmethoxy)butoxymethyl]oxirane
Other names 1,4-Bis(2,3-epoxypropoxy)butane (Tetramethylenebis(oxymethylene))dioxirane 1,4-Bis(2,3-epoxypropyloxy)butane 1,4-Bis(glycidyloxy)butane 1,4-Bis(oxiranylmethyloxy)butane 1,4-Butane diglycidyl ether 1,4-Butanediol diglycidyl ether 1,4-Diglycidyloxybutane Butane-1:4-diol diglycidyl ether Butanediol diglycidyl ether Tetramethylene glycol diglycidyl ether 2,2'-(1,4-Butanediylbis(oxymethylene)bisoxirane)
Identifiers
CAS Number	2425-79-8
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL1450123
ChemSpider	16147
ECHA InfoCard	100.017.611
EC Number	219-371-7
KEGG	D88722
PubChem CID	17046
CompTox Dashboard (EPA)	DTXSID7024667
InChI InChI=1S/C10H18O4/c1(3-11-5-9-7-13-9)2-4-12-6-10-8-14-10/h9-10H,1-8H2 Key: SHKUUQIDMUMQQK-UHFFFAOYSA-N
SMILES C1C(O1)COCCCCOCC2CO2
Properties
Chemical formula	C10H18O4
Molar mass	202.250 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

It is REACH registered.^[3] The IUPAC name is 2-[4-(oxiran-2-ylmethoxy)butoxymethyl]oxirane.

Synthesis

1,4-Butanediol and epichlorohydrin are reacted in the presence of a Lewis acid as catalyst to form a halohydrin: each hydroxyl group of the diol reacts with an epoxide on epichlorohydrin. This process is followed by washing with sodium hydroxide to re-form the epoxide rings in dehydrochlorination reaction.^[4] One of the quality control tests would involve measuring the Epoxy value by determination of the epoxy equivalent weight.

Uses

A key use is modifying the viscosity and properties of epoxy resins^[5] which may then be formulated into CASE applications: Coatings,^[6] Adhesives, Sealants, Elastomers, composite materials, fillers, putties, plasters, modelling clay and semiconductors. It also has a number of medical applications.^[7][8][9] The molecule is also used to synthesize other molecules.^[10][11] As an Epoxy modifier it is classed as an epoxy reactive diluent.The use of the diluent does effect mechanical properties and microstructure of epoxy resins.^[12][13]

Toxicity

The toxicity is fairly well known and understood and is rated as a severe skin and eye irritant. Contact dermatitis is also possible.^[14][15][16]