:Butanone

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. 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.{{Cite web |url=http://www.chemistry.org/portal/a/c/s/1/feature_pro.html?id=c373e908e6e847ac8f6a17245d830100 |title=Direct Routes to Phenol |access-date=2017-12-13 |archive-url=https://web.archive.org/web/20070409042033/http://www.chemistry.org/portal/a/c/s/1/feature_pro.html?id=c373e908e6e847ac8f6a17245d830100 |archive-date=2007-04-09 |url-status=dead }}

Both liquid-phase oxidation of heavy naphtha and the Fischer–Tropsch reaction produce mixed oxygenate streams, from which 2-butanone is extracted by fractionation.Ashford's Dictionary of Industrial Chemicals, Third edition, 2011, {{ISBN|978-0-9522674-3-0}}, pages 6013-4

Butanone is an effective and common solvent{{Cite book| last = Turner| first = Charles F.|author2=McCreery, Joseph W.| title = The Chemistry of Fire and Hazardous Materials| publisher = Allyn and Bacon, Inc.| year = 1981| location = Boston, Massachusetts| pages = 118| isbn = 0-205-06912-6}} and is used in processes involving gums, resins, cellulose acetate and nitrocellulose coatings and in vinyl films.{{Cite book| last = Apps| first = E. A.| title = Printing Ink Technology| publisher = Leonard Hill [Books] Limited| year = 1958|location = London| pages = [https://archive.org/details/printinginktechn00apps/page/101 101]| url =https://archive.org/details/printinginktechn00apps| url-access = registration}} 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.{{Cite book| last = Fairhall| first = Lawrence T.| title = Industrial Toxicology| publisher = The Williams and Wilkins Company| year = 1957| location = Baltimore| pages = 172–173}} Unlike acetone, it forms an azeotrope with water,Lange's Handbook of Chemistry, 10th ed. pp1496-1505CRC Handbook of Chemistry and Physics, 44th ed. pp 2143-2184 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.

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:{{OrgSynth | author = Semon, W. L. | author2 = Damerell, V. R. | title = Dimethylglyoxime | collvol = 2 | collvolpages = 204 | year = 1943 | prep = cv2p0204}}

:File: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.

:File: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

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

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.{{cite web |url=https://www.csb.gov/file.aspx?DocumentId=5703 |title=Investigation Report: Xcel Energy Hydroelectric Plant Penstock Fire |author=U.S. Chemical Safety and Hazard Investigation Board |author-link=U.S. Chemical Safety and Hazard Investigation Board |date=August 2010 |publisher=U.S. Chemical Safety and Hazard Investigation Board}}

Butanone is a constituent of tobacco smoke.{{cite journal|last1=Talhout|first1=Reinskje|last2=Schulz|first2=Thomas|last3=Florek|first3=Ewa|last4=Van Benthem|first4=Jan|last5=Wester|first5=Piet|last6=Opperhuizen|first6=Antoon|title=Hazardous Compounds in Tobacco Smoke|journal=International Journal of Environmental Research and Public Health|volume=8|issue=12|year=2011|pages=613–628|issn=1660-4601|doi=10.3390/ijerph8020613|pmid=21556207|pmc=3084482|doi-access=free}} It is an irritant, causing irritation to the eyes and nose of humans. Serious animal health effects have been seen only at very high levels. There are no long-term studies with animals breathing or drinking it,{{cite web|title=Methyl ethyl ketone (MEK) (CASRN 78-93-3)|url=http://www.epa.gov/iris/subst/0071.htm|website=Integrated Risk Information System (IRIS)|publisher=EPA|access-date=16 March 2015|date=26 September 2003}} and no studies for carcinogenicity in animals breathing or drinking it.{{cite web|title=US Toxicological review of Methyl ethyl ketone In Support of Summary Information on the Integrated Risk Information System (IRIS)|date= September 2003|url=http://www.epa.gov/iris/toxreviews/0071tr.pdf|publisher=US Environmental Protection Agency|access-date=16 March 2015|pages=152}}{{rp|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.{{cite journal | doi = 10.1136/oem.2005.022400| title = Solvent neurotoxicity| date = 2006| last1 = Dick| first1 = F. D.| journal = Occupational and Environmental Medicine| volume = 63| issue = 3| pages = 221–226| pmid = 16497867| pmc = 2078137}}

{{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.{{cite journal |archive-url=https://web.archive.org/web/20220121103345/http://www.jofcr.com/jcrarchives/vol28/v28i4thompson.pdf|archive-date=2022-01-21|url=http://www.jofcr.com/jcrarchives/vol28/v28i4thompson.pdf|title=Implications for cognitive rehabilitation and brain injury from exposure to Methyl Ethyl Ketone (MEK): a review|author=Simon B.N. Thompson|journal=Journal of Cognitive Rehabilitation|date=Winter 2010|volume=28(Winter)|pages=4–14}}

Butanone is listed as a Table II precursor under the United Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances.[http://www.incb.org/pdf/e/list/red.pdf List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control] {{webarchive |url=https://web.archive.org/web/20080227224025/http://www.incb.org/pdf/e/list/red.pdf |date=February 27, 2008 }}, International Narcotics Control Board

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).Federal Register Volume 70, Issue 242 (December 19, 2005){{cite web|author1=Barbara Kanegsberg |title=MEK No Longer a HAP |url=http://www.bfksolutions.com/index.php/newsletter/archived-newsletters/133-mek-no-longer-a-hap |publisher=Bfksolutions newsletter |access-date=2 April 2015 |date=n.d. |url-status=dead |archive-url=https://web.archive.org/web/20150402144959/http://www.bfksolutions.com/index.php/newsletter/archived-newsletters/133-mek-no-longer-a-hap |archive-date=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|date=March 2015}}{{Cite web|url=http://www.pcimag.com/articles/85504-epa-de-lists-mek-from-caa-hap-list|title=EPA De-Lists MEK from CAA HAP List|website=www.pcimag.com|access-date=2016-07-30}}

• Butyraldehyde
• Butane
• n-Butanol
• 2-Butanol

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{{Reflist|30em}}

• [http://www.inchem.org/documents/icsc/icsc/eics0179.htm International Chemical Safety Card 0179]
• [https://web.archive.org/web/20060302121404/http://www.npi.gov.au/database/substance-info/profiles/57.html National Pollutant Inventory: Methyl Ethyl Ketone Fact Sheet]
• [https://www.cdc.gov/niosh/npg/npgd0069.html NIOSH Pocket Guide to Chemical Hazards]
• [http://www.epa.gov/ttn/atw/hlthef/methylet.html US EPA Datasheet]
• {{CPID|id=215|name=Methyl ethyl ketone}}

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Category:Alkanones

Category:Ketone solvents

Category:Pollutants

Category:Commodity chemicals

Category:Sweet-smelling chemicals