n-Butyl glycidyl ether

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]

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
  • InChI=1S/C7H14O2/c1-2-3-4-8-5-7-6-9-7/h7H,2-6H2,1H3
    Key: YSUQLAYJZDEMOT-UHFFFAOYSA-N
  • CCCCOCC1CO1
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.[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]

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. 28 March 2018.
  3. "{{{2}}}". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  4. Jagtap, Ameya Rajendra; More, Aarti (2022-08-01). "Developments in reactive diluents: a review". Polymer Bulletin. 79 (8): 5667–5708. doi:10.1007/s00289-021-03808-5. ISSN 1436-2449. S2CID 235678040.
  5. CID 17049 from PubChem
  6. 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.
  7. International Chemical Safety Card 0115
  8. Monte, Salvatore J. (1998), Pritchard, Geoffrey (ed.), "Diluents and viscosity modifiers for epoxy resins", Plastics Additives: An A-Z reference, Polymer Science and Technology Series, Dordrecht: Springer Netherlands, vol. 1, pp. 211–216, doi:10.1007/978-94-011-5862-6_24, ISBN 978-94-011-5862-6, retrieved 2022-03-29
  9. Urata, Kouichi; Takaishi, Naotake (September 1994). "The alkyl glycidyl ether as synthetic building blocks". Journal of the American Oil Chemists' Society. 71 (9): 1027–1033. doi:10.1007/BF02542274. S2CID 96776835.
  10. Pastarnokienė, Liepa; Jonikaitė-Švėgždienė, Jūratė; Lapinskaitė, Neringa; Kulbokaitė, Rūta; Bočkuvienė, Alma; Kochanė, Tatjana; Makuška, Ričardas (2023-07-01). "The effect of reactive diluents on curing of epoxy resins and properties of the cured epoxy coatings". Journal of Coatings Technology and Research. 20 (4): 1207–1221. doi:10.1007/s11998-022-00737-4. ISSN 1935-3804. S2CID 256749849.
  11. Khalina, Morteza; Beheshty, Mohammad Hosain; Salimi, Ali (2019-08-01). "The effect of reactive diluent on mechanical properties and microstructure of epoxy resins". Polymer Bulletin. 76 (8): 3905–3927. doi:10.1007/s00289-018-2577-6. ISSN 1436-2449. S2CID 105389177.
  12. Chen, Zhen-Kun; Yang, Guo; Yang, Jiao-Ping; Fu, Shao-Yun; Ye, Lin; Huang, Yong-Gang (2009-02-23). "Simultaneously increasing cryogenic strength, ductility and impact resistance of epoxy resins modified by n-butyl glycidyl ether". Polymer. 50 (5): 1316–1323. doi:10.1016/j.polymer.2008.12.048. ISSN 0032-3861.

Further reading
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