N-Butyl glycidyl ether
Chemical compound
From Wikipedia, the free encyclopedia
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.[4]
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| Names | |
|---|---|
| Preferred IUPAC name
2-(Butoxymethyl)oxirane | |
| Other names
1,2-Epoxy-3-butoxypropane 2,3-Epoxypropyl butyl ether (Butoxymethyl)oxirane 1-Butoxy-2,3-epoxypropane | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
| ECHA InfoCard | 100.017.616 |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 1993 |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H14O2 | |
| Molar mass | 130.187 g·mol−1 |
| Appearance | Colorless liquid[1] |
| Odor | Irritating[1] |
| Density | 0.91 g/cm3[1] |
| Boiling point | 164 °C; 327 °F; 437 K[1] |
| 2% (20 °C)[1] | |
| Vapor pressure | 3 mmHg (25 °C)[1] |
| Hazards | |
| Flash point | 130 °F[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
260 mg/m3 (inhalation, mouse)[2] 1030 ppm (inhalation, rat, 8 hours)[2] |
LC50 (median concentration) |
>3500 ppm (mouse, 4 hr)[3] 1030 ppm (rat, 8 hr)[3] |
| NIOSH (US health exposure limits): | |
PEL (Permissible) |
TWA 50 ppm (270 mg/m3)[1] |
REL (Recommended) |
5.6 ppm (30 mg/m3) [15 min][1] |
IDLH (Immediate danger) |
250 ppm[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis
n-Butyl alcohol and epichlorohydrin react to form a halohydrin. This is followed by a caustic dehydrochlorination, to form n-butyl glycidyl ether.[5]
Metabolism
n-Butyl glycidyl ether is metabolized renally to butoxyacetic acid, 3-butoxy-2-hydroxypropionic acid and 3-butoxy-2-acetylaminopropionic acid.[5][6]
Safety
Exposure to n-butyl glycidyl ether through inhalation, eye contact, or skin exposure can cause a cough, sore throat, eye and skin redness, and pain. It is flammable and reacts with strong oxidants, strong bases, strong acids, and amines.[7]
Uses
As an epoxy modifier it is classed as an epoxy reactive diluent.[8] It is also used to synthesize other molecules.[9] The use of the diluent does effect mechanical properties and microstructure of epoxy resins.[10][11] It has been used to simultaneously increase cryogenic strength, ductility and impact resistance of epoxy resins.[12]