234923

Butyl acrylate

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

• Synonym(s): n-Butyl acrylate
• Linear Formula: CH₂=CHCOO(CH₂)₃CH₃
• CAS Number: 141-32-2
• Molecular Weight: 128.17
• UNSPSC Code: 12162002
• NACRES: NA.23
• PubChem Substance ID: 24854065
• EC Number: 205-480-7
• Beilstein/REAXYS Number: 1749970
• MDL number: MFCD00009446

Properties

• vapor density: >1 (vs air)
• Quality Segment: 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

Description

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.[1] Heck coupling reactions of aryl bromides with n-butyl acrylate mediated by phosphine-imidazolium salt have been reported.[2] 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).[3]
• 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).[1]

Safety Information

• pictograms: GHS02,GHS07
• signalword: Warning
• pcodes: P210 - P273 - P280 - P303 + P361 + P353 - P304 + P340 + P312 - P305 + P351 + P338
• 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
• hcodes: H226,H315,H317,H319,H332,H335,H412
• Hazard Classifications: Acute Tox. 4 Inhalation - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3