Sec-Butyl acetate

Last updated
sec-Butyl acetate
Sec-butyl acetate.svg
Sec-Butyl acetate 3D ball.png
Names
Preferred IUPAC name
Butan-2-yl acetate [1]
Other names
  • 2-Butyl acetate
  • sec-Butyl ester
  • s-Butyl acetate
  • sec-Butyl ester of acetic acid
  • 1-Methylpropyl acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.001 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3 Yes check.svgY
    Key: DCKVNWZUADLDEH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C6H12O2/c1-4-5(2)8-6(3)7/h5H,4H2,1-3H3
    Key: DCKVNWZUADLDEH-UHFFFAOYAV
  • O=C(OC(C)CC)C
Properties
C6H12O2
Molar mass 116.160 g·mol−1
AppearanceClear, liquid
Odor Fruity [2]
Density 0.87 g/cm3, liquid
Melting point −99 °C (−146 °F; 174 K)
Boiling point 112 °C (234 °F; 385 K)
0.80 g/100 mL
Vapor pressure 10 mmHg [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable
Flash point 17 °C; 62 °F; 290 K [2]
Explosive limits 1.7–9.8% [2]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm (950 mg/m3) [2]
REL (Recommended)
TWA 200 ppm (950 mg/m3) [2]
IDLH (Immediate danger)
1700 ppm [2]
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. [3] It is a clear flammable liquid with a sweet smell. [4]

Contents

sec-Butyl acetate has three isomers that are also acetate esters: n-butyl acetate, isobutyl acetate, and tert-butyl acetate.

History

The first method of production of sec-butyl acetate was the esterification of sec-butanol and acetic anhydride [5] It was experimentally determined and published in 1946 by Rolf Altschul. [6]

Toxicology

The LD50 for rats is 13 g/kg. [7] Exposure in humans to significant quantities of sec-butyl acetate can cause irritation to the eyes, mouth, throat, nose, and skin. [8] Ingestion and inhalation of sec-butyl acetate can cause central nervous system depression producing symptoms of dizziness and disorientation. [8]

Nomenclature

sec-Butyl acetate is chiral. It has one stereocenter, carbon 2 in the sec-butyl group. The names of the two enantiomers are:

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In organic chemistry, butyl is a four-carbon alkyl radical or substituent group with general chemical formula −C4H9, derived from either of the two isomers (n-butane and isobutane) of butane.

<span class="mw-page-title-main">Ethyl acetate</span> Organic compound (CH₃CO₂CH₂CH₃)

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

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

Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable liquid with a characteristically pleasant smell reminiscent of some glues and nail polish removers. Methyl acetate is occasionally used as a solvent, being weakly polar and lipophilic, but its close relative ethyl acetate is a more common solvent being less toxic and less soluble in water. Methyl acetate has a solubility of 25% in water at room temperature. At elevated temperature its solubility in water is much higher. Methyl acetate is not stable in the presence of strong aqueous bases or aqueous acids. Methyl acetate is not considered a VOC in the USA.

<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

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

Amyl acetate (pentyl acetate) is an organic compound and an ester with the chemical formula CH3COO[CH2]4CH3 and the molecular weight 130.19 g/mol. It is colorless and has a scent similar to bananas and apples. The compound is the condensation product of acetic acid and 1-pentanol. However, esters formed from other pentanol isomers (amyl alcohols), or mixtures of pentanols, are often referred to as amyl acetate. The symptoms of exposure to amyl acetate in humans are dermatitis, central nervous system depression, narcosis and irritation to the eyes and nose.

<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.

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

The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate or β-methylpropyl acetate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid. It is used as a solvent for lacquer and nitrocellulose. Like many esters it has a fruity or floral smell at low concentrations and occurs naturally in raspberries, pears and other plants. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache.

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

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

1-Propanol is a primary alcohol with the formula CH3CH2CH2OH and sometimes represented as PrOH or n-PrOH. It is a colourless liquid and an isomer of 2-propanol. It is formed naturally in small amounts during many fermentation processes and used as a solvent in the pharmaceutical industry, mainly for resins and cellulose esters, and, sometimes, as a disinfecting agent.

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

Isopropyl acetate is an ester, an organic compound which is the product of esterification of acetic acid and isopropanol. It is a clear, colorless liquid with a characteristic fruity odor.

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

tert-Butyl acetate, t-butyl acetate or TBAc is a colorless flammable liquid with a camphor- or blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners and industrial cleaners. It has recently gained EPA volatile organic compound (VOC) exempt status.

<span class="mw-page-title-main">Isoamyl acetate</span> Chemical compound with banana odor

Isoamyl acetate, also known as isopentyl acetate, is an ester formed from isoamyl alcohol and acetic acid, with the molecular formula . It is a colorless liquid that is only slightly soluble in water, but very soluble in most organic solvents. Isoamyl acetate has a strong odor which is described as similar to both banana and pear. Pure isoamyl acetate, or mixtures of isoamyl acetate, amyl acetate, and other flavors in ethanol may be referred to as banana oil or pear oil.

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

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Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

<span class="mw-page-title-main">Chloroacetyl chloride</span> Chemical compound

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

sec-Amyl acetate is an organic compound and an ester. It is formed in an esterification reaction of sec-amyl alcohol (2-pentanol) and acetic acid. It is a colorless liquid.

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.

References

  1. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 370. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 5 6 7 NIOSH Pocket Guide to Chemical Hazards. "#0073". National Institute for Occupational Safety and Health (NIOSH).
  3. ↑ "Acetic acid", Ullman's encyclopedia of industrial chemistry (2003, 6th ed., Vol. 1, pp. 170–171). Weinheim, Germany: Wiley-VCH.
  4. ↑ Howard, H. H. (1993). sec-Butyl acetate. In Handbook of environmental fate and exposure data for organic chemists (Vol. 5, pp. 60–65). Chelsea, MI: Lewis.
  5. ↑ Altschul, R. (1946). "The Reversible Esterification of Carboxylic Acids with Isobutene and Trimethylethylene. Quantitative Studies and Synthetic Applications", Journal of the American Chemical Society, 68(12), 2605–2609.
  6. ↑ "sec-butyl Acetate" . The Merck Index . Royal Society of Chemistry. 2013.
  7. ↑ Canadian Center for Occupational Health and Safety. (1996). 2-Butyl acetate. Retrieved February 20, 2009, from CHEMINFO database.
  8. 1 2 International Programme on Chemical Safety. (2003). sec-Butyl acetate. Retrieved February 20, 2009, from INCHEM database.
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