N-Butyl glycidyl ether

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
CAS Number	2426-08-6
3D model (JSmol)	Interactive image
ChemSpider	16149
ECHA InfoCard	100.017.616
PubChem CID	17049
RTECS number	TX4200000
UNII	M03777A62S  Y
UN number	1993
CompTox Dashboard (EPA)	DTXSID9024691
InChI InChI=1S/C7H14O2/c1-2-3-4-8-5-7-6-9-7/h7H,2-6H2,1H3 Key: YSUQLAYJZDEMOT-UHFFFAOYSA-N
SMILES CCCCOCC1CO1
Properties
Chemical formula	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]
Solubility in water	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] 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]
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). Infobox references

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]

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]

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, vol. 1, Dordrecht: Springer Netherlands, 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

• Epoxy resin technology. Paul F. Bruins, Polytechnic Institute of Brooklyn. New York: Interscience Publishers. 1968. ISBN   0-470-11390-1. OCLC   182890.
• Flick, Ernest W. (1993). Epoxy resins, curing agents, compounds, and modifiers : an industrial guide. Park Ridge, NJ. ISBN   978-0-8155-1708-5. OCLC   915134542.
• Lee, Henry (1967). Handbook of epoxy resins. Kris Neville ([2nd, expanded work] ed.). New York: McGraw-Hill. ISBN   0-07-036997-6. OCLC   311631322.