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Butanone





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(Redirected from Methylethyl ketone)
 


Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone,[a] is an organic compound with the formulaCH3C(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.

Butanone[1]
Skeletal formula of butanone
Ball-and-stick model of butanone
Ball-and-stick model of butanone
Space-filling model of butanone
Space-filling model of butanone
methyl ethyl ketone
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

    CAS Number

    3D model (JSmol)

  • Interactive image
  • Beilstein Reference

    741880
    ChEBI
    ChEMBL
    ChemSpider
    ECHA InfoCard 100.001.054 Edit this at Wikidata

    Gmelin Reference

    25656
    KEGG

    PubChem CID

    RTECS number
    • EL6475000
    UNII
    UN number 1193

    CompTox Dashboard (EPA)

    • InChI=1S/C4H8O/c1-3-4(2)5/h3H2,1-2H3 checkY

      Key: ZWEHNKRNPOVVGH-UHFFFAOYSA-N checkY

    • InChI=1/C4H8O/c1-3-4(2)5/h3H2,1-2H3

      Key: ZWEHNKRNPOVVGH-UHFFFAOYAW

    • O=C(C)CC

    • CCC(=O)C

    Properties

    Chemical formula

    C4H8O
    Molar mass 72.107 g·mol−1
    Appearance Colorless 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)

    Solubility in water

    27.5 g/100mL
    log P 0.37[4]
    Vapor pressure 78 mmHg (20 °C)[3]
    Acidity (pKa) 14.7

    Magnetic susceptibility (χ)

    −45.58·10−6cm3/mol

    Refractive index (nD)

    1.37880
    Viscosity 0.43 cP
    Structure

    Dipole moment

    2.76 D
    Hazards
    GHS labelling:

    Pictograms

    GHS02: FlammableGHS07: Exclamation mark[5]

    Signal word

    Danger[5]

    Hazard statements

    H225, H319, H336[5]

    Precautionary statements

    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 four-colored diamondHealth 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)

    Autoignition
    temperature

    505 °C (941 °F; 778 K)
    Explosive limits 1.4–11.4%[3]
    Lethal dose or concentration (LD, LC):

    LD50 (median dose)

    • 2737 mg/kg (oral, rat)
  • 4050 mg/kg (oral, mouse)[6]
  • LC50 (median concentration)

    • 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).

    checkY verify (what is checkY☒N ?)

    Infobox references

    Production

    edit

    Butanonyl may be produced by oxidation of 2-butanol. The dehydrogenation of 2-butanol is catalysedbycopper, 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 oxidationof2-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

    edit

    Solvent

    edit

    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 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.

    Plastic welding

    edit

    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

    edit

    Butanone is the precursortomethyl 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]

     

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

     

    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

    edit

    Flammability

    edit

    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]

    Health effects

    edit

    Butanone is a constituent of tobacco smoke.[17] 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,[18] and no studies for carcinogenicity in animals breathing or drinking it.[19]: 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.[20]

    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

    edit

    Butanone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[21]

    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).[22][23][24]

    See also

    edit

    Notes

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

    References

    edit
    1. ^ Merck Index, 11th Edition, 5991.
  • ^ a b c d 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.
  • ^ a b c d e f NIOSH Pocket Guide to Chemical Hazards. "#0069". National Institute for Occupational Safety and Health (NIOSH).
  • ^ "butan-2-one_msds".
  • ^ a b c d "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.
  • ^ a b "2-Butanone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  • ^ a b Wilhelm Neier, Guenter Strehlke "2-Butanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.
  • ^ a b c d e 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.
  • ^ "Direct Routes to Phenol". Archived from the original on 2007-04-09. Retrieved 2017-12-13.
  • ^ Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, ISBN 978-0-9522674-3-0, pages 6013-4
  • ^ Apps, E. A. (1958). Printing Ink Technology. London: Leonard Hill [Books] Limited. pp. 101.
  • ^ a b c Fairhall, Lawrence T. (1957). Industrial Toxicology. Baltimore: The Williams and Wilkins Company. pp. 172–173.
  • ^ Lange's Handbook of Chemistry, 10th ed. pp1496-1505
  • ^ CRC Handbook of Chemistry and Physics, 44th ed. pp 2143-2184
  • ^ Semon, W. L.; Damerell, V. R. (1943). "Dimethylglyoxime". Organic Syntheses; Collected Volumes, vol. 2, p. 204.
  • ^ a b 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.
  • ^ 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.
  • ^ "Methyl ethyl ketone (MEK) (CASRN 78-93-3)". Integrated Risk Information System (IRIS). EPA. 26 September 2003. Retrieved 16 March 2015.
  • ^ "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.
  • ^ F D Dick. Solvent neurotoxicity, Occup Environ Med. 2006 Mar; 63(3): 221–226. doi:10.1136/oem.2005.022400, PMC 2078137
  • ^ 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
  • ^ Federal Register Volume 70, Issue 242 (December 19, 2005)
  • ^ 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]
  • ^ "EPA De-Lists MEK from CAA HAP List". www.pcimag.com. Retrieved 2016-07-30.
  • edit

    Retrieved from "https://en.wikipedia.org/w/index.php?title=Butanone&oldid=1220020596"
     



    Last edited on 21 April 2024, at 09:47  





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    This page was last edited on 21 April 2024, at 09:47 (UTC).

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