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;
EC Number	205-480-7;
KEGG	C10921;
PubChem CID	8846;
RTECS number	UD3150000;
UNII	705NM8U35V;
UN number	2348
	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	Clear, 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	ethanol, ethyl ether, acetone, carbon tetrachloride (slight)
Vapor pressure	4 mmHg (20°C)
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H315, H317, H319, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P370+378, P403+233, P403+235
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 C
4H
9O
2CCH=CH
2. 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. Since it polymerizes easily, commercial preparations may contain a polymerization inhibitor 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 is 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

↑ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 ^1.6 ^1.7 ^1.8 ^1.9 NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0075.html.
↑ ^2.0 ^2.1 "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011. https://www.cdc.gov/niosh/pel88/141-32.html.
↑ ^3.0 ^3.1 "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014. https://www.cdc.gov/niosh/ipcsneng/neng0400.html.
↑ ^4.0 ^4.1 ^4.2 Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut et al. (2020). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4.
↑ "Screening Information Data Set for n-Butyl acrylate, CAS #141-32-2". Organization for Economic Cooperation and Development. October 2002. http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html.
↑ "Final report on the safety assessment of Acrylates Copolymer and 33 related cosmetic ingredients". Int. J. Toxicol. 21 Suppl 3: 1–50. 2002. doi:10.1080/10915810290169800. PMID 12537929.
↑ "Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans". Geneva: World Health Organization: IARC. 1999. http://monographs.iarc.fr/ENG/Classification/index.php.
↑ ^8.0 ^8.1 PubChem. "Butyl acrylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/8846.

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[NPG-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 ^1.6 ^1.7 ^1.8 ^1.9 NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0075.html.

[OSHA-2] 2.0 ^2.1 "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011. https://www.cdc.gov/niosh/pel88/141-32.html.

[ICSC-3] 3.0 ^3.1 "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014. https://www.cdc.gov/niosh/ipcsneng/neng0400.html.

[Ullmann-4] 4.0 ^4.1 ^4.2 Ohara, Takashi; Sato, Takahisa; Shimizu, Noboru; Prescher, Günter; Schwind, Helmut; Weiberg, Otto; Marten, Klaus; Greim, Helmut et al. (2020). "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. pp. 1–21. doi:10.1002/14356007.a01_161.pub4.

[5] "Screening Information Data Set for n-Butyl acrylate, CAS #141-32-2". Organization for Economic Cooperation and Development. October 2002. http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html.

[6] "Final report on the safety assessment of Acrylates Copolymer and 33 related cosmetic ingredients". Int. J. Toxicol. 21 Suppl 3: 1–50. 2002. 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. http://monographs.iarc.fr/ENG/Classification/index.php.

[PubChem-8] 8.0 ^8.1 PubChem. "Butyl acrylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/8846.

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
EC Number	205-480-7
KEGG	C10921
PubChem CID	8846
RTECS number	UD3150000
UNII	705NM8U35V
UN number	2348
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	Clear, 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]
Solubility in water	0.1% (20°C)^[1]
Solubility	ethanol, ethyl ether, acetone, carbon tetrachloride (slight)
Vapor pressure	4 mmHg (20°C)^[1]
Hazards
GHS pictograms
GHS Signal word	Warning
GHS hazard statements	H226, H315, H317, H319, H335
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P261, P264, P271, P272, P280, P302+352, P303+361+353, P304+340, P305+351+338, P312, P321, P332+313, P333+313, P337+313, P362, P363, P370+378, P403+233, P403+235
Flash point	39 °C; 103 °F; 313 K^[1]
Autoignition temperature	267 °C (513 °F; 540 K)^[3]
Explosive limits	1.5% - 9.9%^[1]
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	1800 mg/kg (dermal, rabbit)^[2]
LC₅₀ (median concentration)	1000 ppm (4 hr)^[2]
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).
Infobox references