From Wikipedia, the free encyclopedia
n -Butyl glycidyl ether
Names
Preferred IUPAC name
Other names
1,2-Epoxy-3-butoxypropane 2,3-Epoxypropyl butyl ether (Butoxymethyl)oxirane 1-Butoxy-2,3-epoxypropane
Identifiers
ChemSpider
ECHA InfoCard
100.017.616
RTECS number
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
Properties
C 7 H 14 O 2
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):
TWA 50 ppm (270 mg/m3 )
[1]
5.6 ppm (30 mg/m3 ) [15 min]
[1]
250 ppm
[1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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 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
^
a
b
c
d
e
f
g
h
i
j NIOSH Pocket Guide to Chemical Hazards.
"#0081" .
National Institute for Occupational Safety and Health (NIOSH).
^
a
b
c
d
e
f
g
h
"Propane, 1-Butoxy-2,3-epoxy" . CDC/NIOSH. 28 March 2018.
^
a
b
c
"{{{2}}}" . Immediately Dangerous to Life or Health Concentrations (IDLH) .
National Institute for Occupational Safety and Health (NIOSH).
^ 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 .
^
a
b
CID 17049 from
PubChem
^ 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 .
^
International Chemical Safety Card 0115
^ 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
^ 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 .
^ 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 .
^ 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 .
^ 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
Mono-epoxy Di-epoxy Tri-epoxy