Butyl acrylate

Last updated
Butyl acrylate
Butyl acrylate 200.svg
Names
Preferred IUPAC name
Butyl prop-2-enoate
Other names
  • n-Butyl acrylate
  • Butyl ester of acrylic acid
  • Butyl-2-propenoate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.983 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-480-7
KEGG
PubChem CID
RTECS number
  • UD3150000
UNII
UN number 2348
  • 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
  • CCCCOC(=O)C=C
Properties
C7H12O2
Molar mass 128.171 g·mol−1
AppearanceColorless 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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
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):
1800 mg/kg (dermal, rabbit) [3]
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).

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]

Contents

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. [2] [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]

Related Research Articles

Butanol (also called butyl alcohol) is a four-carbon alcohol with a formula of C4H9OH, which occurs in five isomeric structures (four structural isomers), from a straight-chain primary alcohol to a branched-chain tertiary alcohol; all are a butyl or isobutyl group linked to a hydroxyl group (sometimes represented as BuOH, sec-BuOH, i-BuOH, and t-BuOH). These are 1-butanol, two stereoisomers of sec-butyl alcohol, isobutanol and tert-butyl alcohol. Butanol is primarily used as a solvent and as an intermediate in chemical synthesis, and may be used as a fuel. Biologically produced butanol is called biobutanol, which may be n-butanol or isobutanol.

Acrylonitrile is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N. It is a colorless, volatile liquid. It has a pungent odor of garlic or onions. Its molecular structure consists of a vinyl group linked to a nitrile. It is an important monomer for the manufacture of useful plastics such as polyacrylonitrile. It is reactive and toxic at low doses.

Acrylates are the salts, esters, and conjugate bases of acrylic acid. The acrylate ion is the anion CH2=CHCO−2. Often, acrylate refers to esters of acrylic acid, the most common member being methyl acrylate. These acrylates contain vinyl groups. These compounds are of interest because they are bifunctional: the vinyl group is susceptible to polymerization and the carboxylate group carries myriad functionalities.

<span class="mw-page-title-main">Acrylic acid</span> Chemical compound

Acrylic acid (IUPAC: prop-2-enoic 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 characteristic acrid or tart smell. It is miscible with water, alcohols, ethers, and chloroform. More than a million tons are produced annually.

<span class="mw-page-title-main">Barium nitrate</span> Chemical compound

Barium nitrate is the inorganic compound with the chemical formula Ba(NO3)2. It, like most barium salts, is colorless, toxic, and water-soluble. It burns with a green flame and is an oxidizer; the compound is commonly used in pyrotechnics.

<span class="mw-page-title-main">Methyl methacrylate</span> Chemical compound

Methyl methacrylate (MMA) is an organic compound with the formula CH2=C(CH3)COOCH3. This colorless liquid, the methyl ester of methacrylic acid (MAA), is a monomer produced on a large scale for the production of poly(methyl methacrylate) (PMMA).

<i>p</i>-Xylene Chemical compound

p-Xylene (para-xylene) is an aromatic hydrocarbon. It is one of the three isomers of dimethylbenzene known collectively as xylenes. The p- stands for para-, indicating that the two methyl groups in p-xylene occupy the diametrically opposite substituent positions 1 and 4. It is in the positions of the two methyl groups, their arene substitution pattern, that it differs from the other isomers, o-xylene and m-xylene. All have the same chemical formula C6H4(CH3)2. All xylene isomers are colorless and highly flammable. The odor threshold of p-xylene is 0.62 parts per million (ppm).

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">Butyl acetate</span> Chemical compound

n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.

<i>sec</i>-Butyl acetate Chemical compound

sec-Butyl acetate, or s-butyl acetate, is an ester commonly used as a solvent in lacquers and enamels, where it is used in the production of acyclic polymers, vinyl resins, and nitrocellulose. It is a clear flammable liquid with a sweet smell.

<span class="mw-page-title-main">1-Butanol</span> Chemical compound

1-Butanol, also known as butan-1-ol or n-butanol, is a primary alcohol with the chemical formula C4H9OH and a linear structure. Isomers of 1-butanol are isobutanol, butan-2-ol and tert-butanol. The unmodified term butanol usually refers to the straight chain isomer.

<span class="mw-page-title-main">Butane-1-thiol</span> Chemical compound

Butane-1-thiol, also known as butyl mercaptan, is a volatile, clear to yellowish liquid with a fetid odor, commonly described as "skunk" odor. In fact, 1-butanethiol is structurally similar to several major constituents of a skunk's defensive spray but is not actually present in the spray. The scent of 1-butanethiol is so strong that the human nose can easily detect it in the air at concentrations as low as 10 parts per billion. The threshold level for 1-butanethiol is reported as 1.4 ppb

<span class="mw-page-title-main">Ethyl acrylate</span> Chemical compound

Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.

<span class="mw-page-title-main">Methyl acrylate</span> Chemical compound

Methyl acrylate is an organic compound, more accurately the methyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced to make acrylate fiber, which is used to weave synthetic carpets. It is also a reagent in the synthesis of various pharmaceutical intermediates. Owing to the tendency of methyl acrylate to polymerize, samples typically contain an inhibitor such as hydroquinone.

Methacrylonitrile, MeAN in short, is a chemical compound that is an unsaturated aliphatic nitrile, widely used in the preparation of homopolymers, copolymers, elastomers, and plastics and as a chemical intermediate in the preparation of acids, amides, amines, esters, and other nitriles. MeAN is also used as a replacement for acrylonitrile in the manufacture of an acrylonitrile/butadiene/styrene-like polymer. It is a clear and colorless liquid, that has a bitter almond smell.

<i>m</i>-Xylylenediamine Chemical compound

m-Xylylenediamine is an organic compound with the formula C6H4(CH2NH2)2. A colorless oily liquid, it is produced by hydrogenation of isophthalonitrile.

n-Butyl glycidyl ether is an industrial chemical used in adhesives, sealants, and as a paint or coating additive. It is principally used to reduce the viscosity of epoxy resin systems.

<i>n</i>-Butyl lactate Chemical compound

n-Butyl lactate is an industrial chemical and food additive.

<span class="mw-page-title-main">2-Ethylhexyl acrylate</span> Chemical compound

2-Ethylhexyl acrylate is a colorless liquid acrylate used in the making of paints, plastics and adhesives. It has an odor that has been variously described as pleasant or acrid and musty.

<span class="mw-page-title-main">Butyl propionate</span> Butyl ester of propionic acid

Butyl propionate is a butyl ester of propionic acid. This ester has the chemical formula CH3CH2COO(CH2)3CH3.

References

  1. 1 2 3 4 5 6 7 8 9 10 NIOSH Pocket Guide to Chemical Hazards. "#0075". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 "Butyl Acrylate". International Chemical Safety Cards. NIOSH. July 1, 2014.
  3. 1 2 "N-Butyl Acrylate". OSHA/NIOSH. September 28, 2011.
  4. 1 2 3 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.
  8. 1 2 PubChem. "Butyl acrylate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-03-27.
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