Butyl acrylate is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula C4H9O2CCH=CH2. A colorless liquid, it is the butyl ester of acrylic acid. It is used commercially on a large scale as a precursor to polybutylacrylate, which is used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.

Production and properties

Butyl acrylate can be produced by the acid-catalyzed esterification acrylic acid with butanol. Since it polymerizes easily, commercial preparations may contain a polymerization inhibitor such as

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''pa ...

, phenothiazine, or hydroquinone ethyl ether.

Safety

Butyl acrylate is of low acute toxicity with an

LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a toxin, radiation, or pathogen. The value of LD50 for a substance is the ...

(rat) of 3730 mg/kg. In rodent models, butyl acrylate is metabolized by carboxylesterase or reactions with

glutathione Glutathione (GSH, ) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, pe ...

; this detoxification produces

acrylic acid Acrylic acid (IUPAC: propenoic acid) is an organic compound with the formula CH2=CHCOOH. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a ...

butanol Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4 H9 O H, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a bu ...

, and mercapturic acid waste, which is excreted.

References

{{Authority control Acrylate esters Monomers Butyl compounds