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Butyl acrylate is an organic compound 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 poly(butyl acrylate). Especially as copolymers, such materials are used in paints, sealants, coatings, adhesives, fuel, textiles, plastics, and caulk.[4]
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| Names | |
|---|---|
| Preferred IUPAC name
Butyl prop-2-enoate | |
Other names
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| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.983 |
| EC Number |
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| KEGG | |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 2348 |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H12O2 | |
| Molar mass | 128.171 g·mol−1 |
| Appearance | Colorless liquid[1] |
| Odor | Strong, fruity[1] |
| Density | 0.89 g/mL (20°C)[1] |
| Melting point | −64 °C; −83 °F; 209 K[1] |
| Boiling point | 145 °C; 293 °F; 418 K[1] |
| 0.1% (20°C)[1] | |
| Solubility | organic solvents |
| Vapor pressure | 4 mmHg (20°C)[1] |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H226, H315, H317, H319, H335 | |
| P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501 | |
| Flash point | 39 °C; 103 °F; 313 K[1] |
| 267 °C (513 °F; 540 K)[2] | |
| Explosive limits | 1.5% - 9.9%[1] |
| Lethal dose or concentration (LD, LC): | |
LD50 (median dose) |
1800 mg/kg (dermal, rabbit)[3] |
LC50 (median concentration) |
1000 ppm (4 hr)[3] |
| NIOSH (US health exposure limits): | |
REL (Recommended) |
TWA 10 ppm (55 mg/m3)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Butyl acrylate can be produced by the acid-catalyzed esterification of acrylic acid with butanol. It polymerizes easily, therefore commercial preparations contain polymerization inhibitors such as hydroquinone, phenothiazine, or hydroquinone ethyl ether.[2][4]
Butyl acrylate is of low acute toxicity with an LD50 (rat) of 3143 mg/kg.[4]
In rodent models, butyl acrylate is metabolized by carboxylesterase or reactions with glutathione; this detoxification produces acrylic acid, butanol, and mercapturic acid waste, which are excreted.[5][6][7]
Exposure can occur through inhalation, skin and/or eye contact absorption, and ingestion.[8] Symptoms may be dependent on exposure route, with skin and eye contact manifesting in redness, pain, and sensitivity; inhalation resulting in burning sensations, cough, shortness of breath, and sore throat; and ingestion resulting in abdominal pain, nausea, vomiting, and diarrhoea.[8]
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