234923
Butyl acrylate
≥99%, contains 10-60 ppm monomethyl ether hydroquinone as inhibitor
Synonym(s):
n-Butyl acrylate
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About This Item
Linear Formula:
CH2=CHCOO(CH2)3CH3
CAS Number:
Molecular Weight:
128.17
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
EC Number:
205-480-7
Beilstein/REAXYS Number:
1749970
MDL number:
vapor density
>1 (vs air)
Quality Level
vapor pressure
3.3 mmHg ( 20 °C)
assay
≥99%
form
liquid
autoignition temp.
559 °F
contains
10-60 ppm monomethyl ether hydroquinone as inhibitor
expl. lim.
9.9 %
refractive index
n20/D 1.418 (lit.)
bp
145 °C (lit.)
density
0.894 g/mL at 25 °C (lit.)
SMILES string
CCCCOC(=O)C=C
InChI
1S/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H,2-3,5-6H2,1H3
InChI key
CQEYYJKEWSMYFG-UHFFFAOYSA-N
General description
Butyl acrylate is commonly used as a monomer, or building block, in the production of various types of polymers, including acrylate and methacrylate polymers. It is also used in combination with other monomers to achieve specific properties in the resulting polymers. These polymers can be used in a wide range of applications such as paints and coatings, textiles, adhesives, lithium-ion batteries, actuators, and biomedical devices and packaging materials. In the polymerization of butyl acrylate, the most common inhibitor used is monomethyl ether hydroquinone (MEHQ). It is typically added in small quantities (10-60 ppm) to hinder undesirable side reactions during the polymerization, ensuring controlled and high-quality polymer formation. It can also effectively increase the storage stability of butyl acrylate by reacting with free radicals that may initiate polymerization.
Butyl acrylate undergoes radical copolymerization with benzoxazine containing a vinyl group to afford copolymers. Heck coupling reactions of aryl bromides with n-butyl acrylate mediated by phosphine-imidazolium salt have been reported. Copolymerization of styrene and n-butyl acrylate by ATRP catalyzed by CuBr/4,4′-di(5-nonyl)-2,2′-bipyridine has been described.
Butyl acrylate undergoes radical copolymerization with benzoxazine containing a vinyl group to afford copolymers. Heck coupling reactions of aryl bromides with n-butyl acrylate mediated by phosphine-imidazolium salt have been reported. Copolymerization of styrene and n-butyl acrylate by ATRP catalyzed by CuBr/4,4′-di(5-nonyl)-2,2′-bipyridine has been described.
Application
Butyl acrylate (BA) can be used as:
- An electrolyte additive in lithium-ion batteries to improve their low-temperature performance. The addition of BA to the electrolyte led to a significant improvement in the low-temperature performance of the battery, including enhanced ionic conductivity and improved rate capability.
- A monomer to synthesize a shape memory polymer network that contains magnetic nanoparticles for various applications, including actuators and biomedical devices.
- A monomer for the preparation of a polymeric semiconductor with intrinsically stretchable properties. This polymer material is used as a component in field-effect transistor applications.
- Poly(butyl acrylate) particles.
- Poly(butyl acrylate-b-acrylic acid) block copolymer.
- Amphiphilic charged diblock copolymers poly(butyl acrylate)-b-poly(acrylic acid).
- Poly(n-butyl acrylate), via atom transfer radical polymerization (ATRP) of n-butyl acrylate in the presence of CuIBr/4,4′-di(5-nonyl)-2,2′-bipyridine (catalyst).
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signalword
Warning
target_organs
Respiratory system
Storage Class
3 - Flammable liquids
wgk
WGK 1
flash_point_f
98.6 °F - closed cup
flash_point_c
37 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Classifications
Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
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Controlling the Melting of Kinetically Frozen Poly(butyl acrylate-b-acrylic acid) Micelles via Addition of Surfactant
Jacquin M, et al.
Langmuir, 223, 9939-9948 (2007)
C Yang et al.
Organic letters, 3(10), 1511-1514 (2001-06-05)
[reaction: see text] A new phosphine-imidazolium salt, L.HBr (1, L = (1-ethylenediphenylphosphino-3-(mesityl))imidazol-2-ylidene), has been prepared. A combination of 0.5 mol % of Pd(dba)(2) and 0.5 mol % of L.HBr in the presence of 2 equiv of Cs(2)CO(3) as base has
M Jacquin et al.
Journal of colloid and interface science, 316(2), 897-911 (2007-10-02)
We have linked the structural and dynamic properties in aqueous solution of amphiphilic charged diblock copolymers poly(butyl acrylate)-b-poly(acrylic acid), PBA-b-PAA, synthesized by controlled radical polymerization, with the physico-chemical characteristics of the samples. Despite product imperfections, the samples self-assemble in melt