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234923

Sigma-Aldrich

Butyl acrylate

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

Synonyme(s) :

n-Butyl acrylate

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About This Item

Formule linéaire :
CH2=CHCOO(CH2)3CH3
Numéro CAS:
141-32-2
Poids moléculaire :
128.17
Numéro Beilstein :
1749970
Numéro CE :
205-480-7
Numéro MDL:
MFCD00009446
Code UNSPSC :
12162002
ID de substance PubChem :
24854065
Nomenclature NACRES :
NA.23

Densité de vapeur

>1 (vs air)

Niveau de qualité

200

Pression de vapeur

3.3 mmHg ( 20 °C)

Pureté

≥99%

Forme

liquid

Température d'inflammation spontanée

559 °F

Contient

10-60 ppm monomethyl ether hydroquinone as inhibitor

Limite d'explosivité

9.9 %

Indice de réfraction

n20/D 1.418 (lit.)

Point d'ébullition

145 °C (lit.)

Densité

0.894 g/mL at 25 °C (lit.)

Chaîne SMILES 

CCCCOC(=O)C=C

InChI

1S/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H,2-3,5-6H2,1H3

Clé InChI

CQEYYJKEWSMYFG-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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).

Pictogrammes

FlameExclamation mark
GHS02,GHS07

Mention d'avertissement

Warning

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

3 - Flammable liquids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

98.6 °F - closed cup

Point d'éclair (°C)

37 °C - closed cup

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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Articles

Continuous Flow Manufacturing for Monomer Synthesis

The manufacture of monomers for use in ophthalmic applications is driven by the need for higher purity, improved reliability of manufacturing supply, but ultimately by the need for the increased comfort, convenience, and safety of contact lens wearers. Daily wear contact lenses have the potential to fill this need for many customers; however, their widespread use is constrained by higher costs compared to weekly- or monthly-based lenses. New approaches that improve cost structure and result in higher quality raw materials are needed to help make contact lenses more affordable and accelerate growth of the contact lens market.

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.

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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