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[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

Tracking categories (test):

* SizeSet

Butyl acrylate is an organic compound with the formula C

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. Tt polymerizes easily, therefore, commercial preparations contain a 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 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. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0075.html.
2. ↑ 2.0 2.1 "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011. https://www.cdc.gov/niosh/pel88/141-32.html.
3. ↑ 3.0 3.1 "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014. https://www.cdc.gov/niosh/ipcsneng/neng0400.html.
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.
8. ↑ 8.0 8.1 PubChem. "Butyl acrylate" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/8846.

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Butyl_acrylate&oldid=825334"
*[CID]: Compound ID
*[H226]: Flammable liquid and vapour
*[H315]: Causes skin irritation
*[H317]: May cause an allergic skin reaction
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P210]: Keep away from heat/sparks/open flames/hot surfaces – No smoking
*[P233]: Keep container tightly closed
*[P240]: Ground/bond container and receiving equipment
*[P241]: Use explosion-proof electrical/ventilating/light/…/equipment
*[P242]: Use only non-sparking tools
*[P243]: Take precautionary measures against static discharge
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P272]: Contaminated work clothing should not be allowed out of the workplace
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P303+361+353]: IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P333+313]: If skin irritation or a rash occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P363]: Wash contaminated clothing before reuse
*[P370+378]: In case of fire: Use … for extinction
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P403+235]: Store in a well ventilated place. Keep cool