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234923

Sigma-Aldrich

Butyl acrylate

≥99%, contains 10-60 ppm monomethyl ether hydroquinone as inhibitor

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Synonym(s):
n-Butyl acrylate
Linear Formula:
CH2=CHCOO(CH2)3CH3
CAS Number:
Molecular Weight:
128.17
Beilstein/REAXYS Number:
1749970
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.23

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

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1 of 4

This Item
327182M273018.00832
vibrant-m

234923

Butyl acrylate

vibrant-m

327182

tert-Butyl acrylate

vibrant-m

M27301

Methyl acrylate

vibrant-m

8.00832

Butyl acrylate

form

liquid

form

liquid

form

liquid

form

liquid

bp

145 °C (lit.)

bp

61-63 °C/60 mmHg (lit.)

bp

80 °C (lit.)

bp

147-148 °C/1013 hPa

refractive index

n20/D 1.418 (lit.)

refractive index

n20/D 1.410 (lit.)

refractive index

n20/D 1.402 (lit.)

refractive index

-

density

0.894 g/mL at 25 °C (lit.)

density

0.875 g/mL at 25 °C (lit.)

density

0.956 g/mL at 25 °C (lit.)

density

0.90 g/cm3 at 20 °C

vapor density

>1 (vs air)

vapor density

-

vapor density

3 (vs air)

vapor density

-

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.

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.
Butyl acrylate is used to prepare:
  • 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).

pictograms

FlameExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Storage Class

3 - Flammable liquids

wgk_germany

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


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Customers Also Viewed

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
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)
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
Atom transfer radical copolymerization of styrene and n-butyl acrylate.
Arehart SV and Matyjaszewski K.
Macromolecules, 32(7), 2221-2231 (1999)
Conducting polyaniline composite: From syntheses in waterborne systems to chemical sensor devices
Joubert M, et al.
Polymer, 51(8), 1716-1722 (2010)

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