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234923

Sigma-Aldrich

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:
141-32-2
Molecular Weight:
128.17
Beilstein:
1749970
EC Number:
205-480-7
MDL number:
MFCD00009446
UNSPSC Code:
12162002
PubChem Substance ID:
24854065
NACRES:
NA.23

vapor density

>1 (vs air)

Quality Level

200

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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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
GHS02,GHS07

Signal Word

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 Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

98.6 °F - closed cup

Flash Point(C)

37 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Conducting polyaniline composite: From syntheses in waterborne systems to chemical sensor devices
Joubert M, et al.
Polymer, 51(8), 1716-1722 (2010)
Atom transfer radical copolymerization of styrene and n-butyl acrylate.
Arehart SV and Matyjaszewski K.
Macromolecules, 32(7), 2221-2231 (1999)
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
Tsutomu Takeichi et al.
Molecules (Basel, Switzerland), 20(4), 6488-6503 (2015-04-14)
A benzoxazine containing a vinyl group (P-4va) was prepared by the reaction of phenol, 4-vinylaniline, and paraformaldehyde. A differential scanning calorimetry (DSC) study revealed that ring-opening polymerization of the benzoxazine and chain polymerization of the vinyl group occurred in the
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
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Heck Reaction

The Heck reaction is the palladium catalyzed cross-coupling reaction between alkenes and aryl or vinyl halides (or triflates) to afford substituted alkenes.

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