n-Butyl glycidyl ether

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive.

n-Butyl glycidyl ether
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)
ChemSpider
ECHA InfoCard 100.017.616
RTECS number
  • TX4200000
UNII
UN number 1993
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):
260 mg/m3 (inhalation, mouse)[2]

1030 ppm (inhalation, rat, 8 hours)[2]
700 mg/kg (intraperitoneal, mouse)[2]
1140 mg/kg (intraperitoneal, rat)[2]
1530 mg/kg (oral, mouse)[2]
1660 mg/kg (oral, rat)[2]
2520 µL/kg (skin, rabbit)[2]
>2150 mg/kg (skin, rat)[2]
2050 mg/kg (oral, rat)[3]

>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).
Infobox references

Synthesis

n-Butyl alcohol and epichlorohydrin react in a condensation reaction to form a halohydrin. This is followed by a caustic dehydrochlorination, to form n-butyl glycidyl ether.[4]

Metabolism

n-Butyl glycidyl ether is metabolized renally to butoxyacetic acid, 3-butoxy-2-hydroxypropionic acid and 3-butoxy-2-acetylaminopropionic acid.[4][5]

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.[6]

References
  1. NIOSH Pocket Guide to Chemical Hazards. "#0081". National Institute for Occupational Safety and Health (NIOSH).
  2. "Propane, 1-Butoxy-2,3-epoxy". CDC/NIOSH.
  3. "{{{2}}}". Immediately Dangerous to Life and Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. CID 17049 from PubChem
  5. Eadsforth, C. V.; Hutson, D. H.; Logan, C. J.; Morrison, B. J. (1985). "The metabolism of n-butyl glycidyl ether in the rat and rabbit". Xenobiotica. 15 (7): 579–89. doi:10.3109/00498258509045887. PMID 4049898.
  6. International Chemical Safety Card 0115
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