Butyl acrylate

Butyl acrylate
Names
	Preferred IUPAC name Butyl prop-2-enoate
	Other names n-Butyl acrylate; Butyl ester of acrylic acid; Butyl-2-propenoate;
Identifiers
CAS Number	141-32-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:3245;
ChEMBL	ChEMBL1546388;
ChemSpider	8514;
ECHA InfoCard	100.004.983
EC Number	205-480-7;
KEGG	C10921;
PubChem CID	8846;
RTECS number	UD3150000;
UNII	705NM8U35V;
UN number	2348
CompTox Dashboard (EPA)	DTXSID6024676 ;
	InChI InChI=1S/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H, 2-3,5-6H2,1H3 Key: CQEYYJKEWSMYFG-UHFFFAOYSA-N; InChI=1/C7H12O2/c1-3-5-6-9-7(8)4-2/h4H, 2-3,5-6H2,1H3 Key: CQEYYJKEWSMYFG-UHFFFAOYAL;
	SMILES CCCCOC(=O)C=C;
Properties
Chemical formula	C7H12O2
Molar mass	128.171 g·mol−1
Appearance	Colorless liquid
Odor	Strong, fruity
Density	0.89 g/mL (20°C)
Melting point	−64 °C; −83 °F; 209 K
Boiling point	145 °C; 293 °F; 418 K
Solubility in water	0.1% (20°C)
Solubility	organic solvents
Vapor pressure	4 mmHg (20°C)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H226, H315, H317, H319, H335
Precautionary statements	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
Autoignition; temperature	267 °C (513 °F; 540 K)
Explosive limits	1.5% - 9.9%
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	1800 mg/kg (dermal, rabbit)
LC50 (median concentration)	1000 ppm (4 hr)
	NIOSH (US health exposure limits):
REL (Recommended)	TWA 10 ppm (55 mg/m3)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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]

Production and properties

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.^[3]^[4]

Safety

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]

References

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH).
^ ^a ^b "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011.
^ ^a ^b "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014.
^ ^a ^b ^c Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 9783527303854.
^ "Screening Information Data Set for n-Butyl acrylate, CAS #141-32-2". Organization for Economic Cooperation and Development. October 2002. Archived from the original on 2015-11-07.
^ Zondlo Fiume M (2002). "Final report on the safety assessment of Acrylates Copolymer and 33 related cosmetic ingredients". Int. J. Toxicol. 21 Suppl 3: 1–50. doi:10.1080/10915810290169800. PMID 12537929.
^ "Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans". Geneva: World Health Organization: IARC. 1999.
^ ^a ^b PubChem. "Butyl acrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-27.

[NPG-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH).

[OSHA-2] "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011.

[ICSC-3] "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014.

[Ullmann-4] Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut; Shaffer, Timothy D.; Nandi, Partha (2020). "Acrylic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4. ISBN 9783527303854.

[5] "Screening Information Data Set for n-Butyl acrylate, CAS #141-32-2". Organization for Economic Cooperation and Development. October 2002. Archived from the original on 2015-11-07.

[6] Zondlo Fiume M (2002). "Final report on the safety assessment of Acrylates Copolymer and 33 related cosmetic ingredients". Int. J. Toxicol. 21 Suppl 3: 1–50. doi:10.1080/10915810290169800. PMID 12537929.

[7] "Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans". Geneva: World Health Organization: IARC. 1999.

[PubChem-8] PubChem. "Butyl acrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-27.

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