Butanone

Last updated
Butanone [1]
Butanone-skeletal-structure.svg
Ball-and-stick model of butanone Butanone-3D-balls.png
Ball-and-stick model of butanone
Space-filling model of butanone Butanone-3D-vdW.png
Space-filling model of butanone
Methyl ethyl ketone 45ml.jpg
Names
Preferred IUPAC name
Butan-2-one [2]
Other names
  • 2-Butanone
  • Ethyl methyl ketone [2]
  • Ethylmethylketone
  • Methyl ethyl ketone (MEK; deprecated [2] )
  • Methylpropanone
  • Methylacetone
Identifiers
3D model (JSmol)
741880
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.054 OOjs UI icon edit-ltr-progressive.svg
25656
KEGG
PubChem CID
RTECS number
  • EL6475000
UNII
UN number 1193
  • InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 Yes check.svgY
    Key: ZWEHNKRNPOVVGH-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C4H8O/c1-3-4(2)5/h3H2,1-2H3
    Key: ZWEHNKRNPOVVGH-UHFFFAOYAW
  • O=C(C)CC
  • CCC(=O)C
Properties
C4H8O
Molar mass 72.107 g·mol−1
AppearanceColorless liquid
Odor Mint or acetone-like [3]
Density 0.8050 g/mL
Melting point −86 °C (−123 °F; 187 K)
Boiling point 79.64 °C (175.35 °F; 352.79 K)
27.5 g/100 mL
log P 0.37 [4]
Vapor pressure 78 mmHg (20 °C) [3]
Acidity (pKa)14.7
−45.58·10−6 cm3/mol
1.37880
Viscosity 0.43  cP
Structure
2.76  D
Hazards
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg [5]
Danger [5]
H225, H319, H336 [5]
P210, P233, P240, P241, P242, P243, P261, P264, P271, P280, P303+P361+P353, P304+P340, P305+P351+P338, P312, P337+P313, P370+P378, P403+P233, P403+P235, P405, P501 [5]
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
3
0
Flash point −9 °C (16 °F; 264 K)
505 °C (941 °F; 778 K)
Explosive limits 1.4–11.4% [3]
Lethal dose or concentration (LD, LC):
  • 2737 mg/kg (oral, rat)
  • 4050 mg/kg (oral, mouse) [6]
  • 12667 ppm (mammal)
  • 13333 ppm (mouse, 2 hr)
  • 7833 ppm (rat, 8 hr) [6]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 200 ppm (590 mg/m3) [3]
REL (Recommended)
TWA 200 ppm (590 mg/m3) ST 300 ppm (885 mg/m3) [3]
IDLH (Immediate danger)
3000 ppm [3]
Safety data sheet (SDS) Safety Data Sheet
Related compounds
Related ketones
Acetone; 3-pentanone; 3-methylbutanone
Supplementary data page
Butanone (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, [a] is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. [7] It is partially soluble in water, and is commonly used as an industrial solvent. [8] It is an isomer of another solvent, tetrahydrofuran.

Contents

Production

Butanone may be produced by oxidation of 2-butanol. The dehydrogenation of 2-butanol is catalysed by copper, zinc, or bronze:

CH3CH(OH)CH2CH3 → CH3C(O)CH2CH3 + H2

This is used to produce approximately 700 million kilograms yearly. Other syntheses that have been examined but not implemented include Wacker oxidation of 2-butene and oxidation of isobutylbenzene, which is analogous to the industrial production of acetone. [7] The cumene process can be modified to produce phenol and a mixture of acetone and butanone instead of only phenol and acetone in the original. [9]

Both liquid-phase oxidation of heavy naphtha and the Fischer–Tropsch reaction produce mixed oxygenate streams, from which 2-butanone is extracted by fractionation. [10]

Applications

Solvent

Butanone is an effective and common solvent [8] and is used in processes involving gums, resins, cellulose acetate and nitrocellulose coatings and in vinyl films. [11] For this reason it finds use in the manufacture of plastics, textiles, in the production of paraffin wax, and in household products such as lacquer, varnishes, paint remover, a denaturing agent for denatured alcohol, glues, and as a cleaning agent. It is a prime component of plumbers' priming fluid, used to clean PVC materials. It has similar solvent properties to acetone but boils at a higher temperature and has a significantly slower evaporation rate. [12] Unlike acetone, it forms an azeotrope with water, [13] [14] making it useful for azeotropic distillation of moisture in certain applications. Butanone is also used in dry erase markers as the solvent of the erasable dye.

The hydroxylamine derivative of butanone is methylethyl ketone oxime (MEKO), which also find use in paints and varnishes as an anti-skinning agent.

Plastic welding

As butanone dissolves polystyrene and many other plastics, it is sold as "model cement" for use in connecting parts of scale model kits. Though often considered an adhesive, it is functioning as a welding agent in this context.

Other uses

Butanone is the precursor to methyl ethyl ketone peroxide, which is a catalyst for some polymerization reactions such as crosslinking of unsaturated polyester resins. Dimethylglyoxime can be prepared from butanone first by reaction with ethyl nitrite to give diacetyl monoxime followed by conversion to the dioxime: [15]

Preparation of dimethylglyoxime.png

In the peroxide process on producing hydrazine, the starting chemical ammonia is bonded to butanone, oxidized by hydrogen peroxide, bonded to another ammonia molecule.

Pechiney-Ugine-Kuhlmann process.png

In the final step of the process, hydrolysis produces the desired product, hydrazine, and regenerates the butanone.

Me(Et)C=NN=C(Et)Me + 2 H2O → 2 Me(Et)C=O + N2H4

Safety

Flammability

Butanone can react with most oxidizing materials and can produce fires. [8] It is moderately explosive, requiring only a small flame or spark to cause a vigorous reaction. [8] The vapor is heavier than air, so it can accumulate at low points. It is explosive at concentrations between 1.4 and 11.4%. [16] Concentrations in the air high enough to be flammable are intolerable to humans due to the irritating nature of the vapor. [12] Butanone fires should be extinguished with carbon dioxide, dry agents, or alcohol-resistant foam. [8]

The ignition of butanone vapor was the proximate cause of the 2007 Xcel Energy Cabin Creek fire, resulting in the deaths of five workers in a hydroelectric penstock. After the incident, the U.S. Chemical Safety and Hazard Investigation Board specifically noted the danger posed by butanone in confined spaces, and suggested 1,1,1-trichloroethane or limonene as safer alternatives. [17]

Health effects

Butanone is a constituent of tobacco smoke. [18] It is an irritant, causing irritation to the eyes and nose of humans. [12] Serious animal health effects have been seen only at very high levels. There are no long-term studies with animals breathing or drinking it, [19] and no studies for carcinogenicity in animals breathing or drinking it. [20] : 96  There is some evidence that butanone can potentiate the toxicity of other solvents, in contrast to the calculation of mixed solvent exposures by simply adding exposures. [21]

As of 2010, the United States Environmental Protection Agency (EPA) listed butanone as a toxic chemical. There are reports of neuropsychological effects. It is rapidly absorbed through undamaged skin and lungs. It contributes to the formation of ground-level ozone, which is toxic in low concentrations. [16]

Regulation

Butanone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances. [22]

Emission of butanone was regulated in the US as a hazardous air pollutant, because it is a volatile organic compound contributing to the formation of tropospheric (ground-level) ozone. In 2005, the US Environmental Protection Agency removed butanone from the list of hazardous air pollutants (HAPs). [23] [24] [25]

See also

Notes

  1. ↑ The international standards group IUPAC has deprecated the term methyl ethyl ketone, and now recommends using ethyl methyl ketone instead. [2]

Related Research Articles

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.

A paint thinner is a solvent used to dilute oil-based paints or varnish. In this context, to dilute is also known as to 'thin'. Paint thinners are diluents. Solvents labeled "paint thinner" are usually white or mineral spirits.

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

2-Pentanone or methyl propyl ketone (MPK) is a ketone and solvent of minor importance. It is comparable to methyl ethyl ketone, but has a lower solvency and is more expensive. It occurs naturally in Nicotiana tabacum (Tobacco) and blue cheese as a metabolic product of Penicillium mold growth.

<span class="mw-page-title-main">3-Pentanone</span> Chemical compound

3-Pentanone is a simple, symmetrical dialkyl ketone. It is a colorless liquid ketone with an odor like that of acetone. It is soluble in about 25 parts water, but miscible with organic solvents.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

<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">Cyclohexanone</span> Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has a sweet odor reminiscent of benzaldehyde. Over time, samples of cyclohexanone assume a pale yellow color.

<span class="mw-page-title-main">Acetone</span> Organic compound ((CH3)2CO); simplest ketone

Acetone is an organic compound with the formula (CH3)2CO. It is the simplest and smallest ketone. It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.

<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">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK, 4-methylpentan-2-one) is an organic compound with the condensed chemical formula (CH3)2CHCH2C(O)CH3. This ketone is a colourless liquid that is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

<span class="mw-page-title-main">Mesityl oxide</span> Chemical compound

Mesityl oxide is a α,β-unsaturated ketone with the formula CH3C(O)CH=C(CH3)2. This compound is a colorless, volatile liquid with a honey-like odor.

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

Isobutanol (IUPAC nomenclature: 2-methylpropan-1-ol) is an organic compound with the formula (CH3)2CHCH2OH (sometimes represented as i-BuOH). This colorless, flammable liquid with a characteristic smell is mainly used as a solvent either directly or as its esters. Its isomers are 1-butanol, 2-butanol, and tert-butanol, all of which are important industrially.

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

2-Ethylhexanol is an organic compound with the chemical formula CH3CH2CH2CH2CH(CH2CH3)CH2OH. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and as a co-solvent in lithium-ion batteries. Notably, dimethyl carbonate is a weak methylating agent, and is not considered as a carcinogen. Instead, dimethyl carbonate is often considered to be a green reagent, and it is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the United States.

<span class="mw-page-title-main">Isophorone</span> Alpha-beta unsaturated cyclic ketone

Isophorone is an α,β-unsaturated cyclic ketone. It is a colorless liquid with a characteristic peppermint-like odor, although commercial samples can appear yellowish. Used as a solvent and as a precursor to polymers, it is produced on a large scale industrially.

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

3-Methyl-2-butanone is a ketone and solvent of minor importance. It is comparable to MEK, but has a lower solvency and is more expensive.

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

Methyl cyanoacrylate is an organic compound that contains several functional groups: a methyl ester, a nitrile, and an alkene. It is a colorless liquid with low viscosity. Its chief use is as the main component of cyanoacrylate glues. It can be encountered under many trade names. Methyl cyanoacrylate is less commonly encountered than ethyl cyanoacrylate.

Isopropyl alcohol is a colorless, flammable, organic compound with a pungent alcoholic odor.

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

2-Hexanone is a ketone used as a general solvent and in paints. It dissolves cellulose nitrate, vinyl polymers and copolymers, and natural and synthetic resins. It is recommended as a solvent because it is photochemically inactive; however it has a very low safe threshold limit value. 2-Hexanone is absorbed through the lungs, orally and dermally and its metabolite, 2,5-hexanedione, is neurotoxic. Animal tests have shown that the neurotoxic effect of 2-hexanone may be potentiated by simultaneous administration of 2-butanone.

<span class="mw-page-title-main">3-Heptanone</span> Chemical compound


3-Heptanone, is a seven carbon ketone. It is a colorless liquid with a "green odor," also described to have a fruity scent. It is often used as a perfume/fragrance, as a solvent for cellulose, nitrocellulose, or vinyl resins, and as a synthetic building block in the preparation of other organic molecules.

References

  1. ↑ Merck Index , 11th Edition, 5991.
  2. 1 2 3 4 Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 725. doi:10.1039/9781849733069-FP001. ISBN   978-0-85404-182-4.
  3. 1 2 3 4 5 6 NIOSH Pocket Guide to Chemical Hazards. "#0069". National Institute for Occupational Safety and Health (NIOSH).
  4. ↑ "butan-2-one_msds".
  5. 1 2 3 4 "Safety Data Sheet - Klean Strip - Methyl Ethyl Ketone (MEK)" (PDF). Kleanstrip.com. Klean Strip. 15 April 2015. Archived from the original (PDF) on 17 April 2018. Retrieved 5 November 2019.
  6. 1 2 "2-Butanone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  7. 1 2 Wilhelm Neier, Guenter Strehlke "2-Butanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.
  8. 1 2 3 4 5 Turner, Charles F.; McCreery, Joseph W. (1981). The Chemistry of Fire and Hazardous Materials. Boston, Massachusetts: Allyn and Bacon, Inc. p. 118. ISBN   0-205-06912-6.
  9. ↑ "Direct Routes to Phenol". Archived from the original on 2007-04-09. Retrieved 2017-12-13.
  10. ↑ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, ISBN   978-0-9522674-3-0, pages 6013-4
  11. ↑ Apps, E. A. (1958). Printing Ink Technology . London: Leonard Hill [Books] Limited. pp.  101.
  12. 1 2 3 Fairhall, Lawrence T. (1957). Industrial Toxicology. Baltimore: The Williams and Wilkins Company. pp. 172–173.
  13. ↑ Lange's Handbook of Chemistry, 10th ed. pp1496-1505
  14. ↑ CRC Handbook of Chemistry and Physics, 44th ed. pp 2143-2184
  15. ↑ Semon, W. L.; Damerell, V. R. (1943). "Dimethylglyoxime". Organic Syntheses ; Collected Volumes, vol. 2, p. 204.
  16. 1 2 Simon B.N. Thompson (Winter 2010). "Implications for cognitive rehabilitation and brain injury from exposure to Methyl Ethyl Ketone (MEK): a review" (PDF). Journal of Cognitive Rehabilitation. 28(Winter): 4–14. Archived from the original (PDF) on 2022-01-21.
  17. ↑ U.S. Chemical Safety and Hazard Investigation Board (August 2010). "Investigation Report: Xcel Energy Hydroelectric Plant Penstock Fire". U.S. Chemical Safety and Hazard Investigation Board.
  18. ↑ Talhout, Reinskje; Schulz, Thomas; Florek, Ewa; Van Benthem, Jan; Wester, Piet; Opperhuizen, Antoon (2011). "Hazardous Compounds in Tobacco Smoke". International Journal of Environmental Research and Public Health. 8 (12): 613–628. doi: 10.3390/ijerph8020613 . ISSN   1660-4601. PMC   3084482 . PMID   21556207.
  19. ↑ "Methyl ethyl ketone (MEK) (CASRN 78-93-3)". Integrated Risk Information System (IRIS). EPA. 26 September 2003. Retrieved 16 March 2015.
  20. ↑ "US Toxicological review of Methyl ethyl ketone In Support of Summary Information on the Integrated Risk Information System (IRIS)" (PDF). US Environmental Protection Agency. September 2003. p. 152. Retrieved 16 March 2015.
  21. ↑ Dick, F. D. (2006). "Solvent neurotoxicity". Occupational and Environmental Medicine. 63 (3): 221–226. doi:10.1136/oem.2005.022400. PMC   2078137 . PMID   16497867.
  22. ↑ List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control Archived February 27, 2008, at the Wayback Machine , International Narcotics Control Board
  23. ↑ Federal Register Volume 70, Issue 242 (December 19, 2005)
  24. ↑ Barbara Kanegsberg (n.d.). "MEK No Longer a HAP". Bfksolutions newsletter. Archived from the original on 2 April 2015. Retrieved 2 April 2015. After technical review and consideration of public comments, EPA concluded that potential exposures to butanone emitted from industrial processes may not reasonably be anticipated to cause human health or environmental problems.[ citation needed ]
  25. ↑ "EPA De-Lists MEK from CAA HAP List". www.pcimag.com. Retrieved 2016-07-30.
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