Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula(CH3)2CO.[22] It is the simplest and smallest ketone (>C=O). It is a colorless, highly volatile, and flammable liquid with a characteristic pungent odor.
From the 17th century and before modern developments in organic chemistry nomenclature, acetone was given many different names. Those names include spirit of Saturn, which was given when it was thought to be a compound of lead, and later pyro-acetic spirit and pyro-acetic ester.[6]
Unlike many compounds with the acet- prefix having a 2-carbon chain, acetone has a 3-carbon chain which has caused confusion since there cannot be a ketone with 2 carbons. The prefix refers to acetone's relation to vinegar (acetum in Latin, also the source of the words "acid" and "acetic"), rather than its chemical structure.[28]
In 1832, French chemist Jean-Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone.[31][32] In 1833, French chemists Antoine Bussy and Michel Chevreul decided to name acetone by adding the suffix -one to the stem of the corresponding acid (viz, acetic acid) just as a similarly prepared product of what was then confused with margaric acid was named margarone.[33][28] By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl;[34] the following year, the French chemist Charles Frédéric Gerhardt concurred.[35] In 1865, the German chemist August Kekulé published the modern structural formula for acetone.[36][37] Johann Josef Loschmidt had presented the structure of acetone in 1861,[38] but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the process for industrial production of acetone (Weizmann Process).[39]
Production
In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year.[40] With 1.56 million tonnes per year, the United States had the highest production capacity,[41] followed by Taiwan and mainland China. The largest producer of acetone is INEOS Phenol, owning 17% of the world's capacity, with also significant capacity (7–8%) by Mitsui, Sunoco and Shell in 2010.[40] INEOS Phenol also owns the world's largest production site (420,000 tonnes/annum) in Beveren (Belgium). Spot price of acetone in summer 2011 was 1100–1250 USD/tonne in the United States.[42]
Current method
Acetone is produced directly or indirectly from propene. Approximately 83% of acetone is produced via the cumene process;[24] as a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:
Other processes involve the direct oxidation of propylene (Wacker-Hoechst process), or the hydration of propylene to give 2-propanol, which is oxidized (dehydrogenated) to acetone.[24]
Like most ketones, acetone exhibits the keto–enol tautomerism in which the nominal keto structure (CH3)2C=O of acetone itself is in equilibrium with the enol isomer (CH3)C(OH)=(CH2) (prop-1-en-2-ol). In acetone vapor at ambient temperature, only 2.4×10−7% of the molecules are in the enol form.[45]
In the presence of suitable catalysts, two acetone molecules also combine to form the compound diacetone alcohol(CH3)C=O(CH2)C(OH)(CH3)2, which on dehydration gives mesityl oxide(CH3)C=O(CH)=C(CH3)2. This product can further combine with another acetone molecule, with loss of another molecule of water, yielding phorone and other compounds.[46]
Acetone is a weak Lewis base that forms adducts with soft acids like I2 and hard acids like phenol. Acetone also forms complexes with divalent metals.[47][48]
Polymerisation
One might expect acetone to also form polymers and (possibly cyclic) oligomers of two types. In one type, units could be acetone molecules linked by ether bridges −O− derived from opening of the double bond, to give a polyketal-like (PKA) chain [−O−C(CH3)2−]n. The other type could be obtained through repeated aldol condensation, with one molecule of water removed at each step, yielding a poly(methylacetylene) (PMA) chain [−CH=C(CH3)−]n.[49]
The conversion of acetone to a polyketal (PKA) would be analogous to the formation of paraformaldehyde from formaldehyde, and of trithioacetone from thioacetone. In 1960, Soviet chemists observed that the thermodynamics of this process is unfavourable for liquid acetone, so that it (unlike thioacetone and formol) is not expected to polymerise spontaneously, even with catalysts. However, they observed that the thermodynamics became favourable for crystalline solid acetone at the melting point (−96 °C). They claimed to have obtained such a polymer (a white elastic solid, soluble in acetone, stable for several hours at room temperature) by depositing vapor of acetone, with some magnesium as a catalyst, onto a very cold surface.[50] In 1962, Wasaburo Kawai reported the synthesis of a similar product, from liquid acetone cooled to −70 to −78 °C, using n-butyllithium or triethylaluminium as catalysts. He claimed that the infraredabsorption spectrum showed the presence of −O− linkages but no C=O groups.[51] However, conflicting results were obtained later by other investigators.[49]
Structure of possible acetone polymer
The PMA type polymers of acetone would be equivalent to the product of polymerisation of propyne, except for a keto end group.[49]
Natural occurrence
Humans exhale several milligrams of acetone per day. It arises from decarboxylation of acetoacetate.[52][53] Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies. Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue. Certain health conditions, such as alcoholism and diabetes, can produce ketoacidosis, uncontrollable ketosis that leads to a sharp, and potentially fatal, increase in the acidity of the blood. Since it is a byproduct of fermentation, acetone is a byproduct of the distillery industry.[52]
Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning polyester resin, cleaning tools used with it, and dissolving two-part epoxies and superglue before they harden. It is used as one of the volatile components of some paints and varnishes. As a heavy-duty degreaser, it is useful in the preparation of metal prior to painting or soldering, and to remove rosin flux after soldering (to prevent adhesion of dirt and electrical leakage and perhaps corrosion or for cosmetic reasons), although it may attack some electronic components, such as polystyrene capacitors.[57]
Although itself flammable, acetone is used extensively as a solvent for the safe transportation and storage of acetylene, which cannot be safely pressurized as a pure compound. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One litre of acetone can dissolve around 250 litres of acetylene at a pressure of 10 bars (1.0 MPa).[58][59]
A variety of organic reactions employ acetone as a polar, aprotic solvent. It is critical in the Jones oxidation. Because acetone is cheap, volatile, and dissolves or decomposes with most laboratory chemicals, an acetone rinse is the standard technique to remove solid resides from laboratory glassware before a final wash.[63] Despite common desiccatory use, acetone dries only via bulk displacement and dilution. It forms no azeotropes with water (see azeotrope tables).[64]
Acetone freezes well below −78 °C. An acetone/dry ice mixture cools many low-temperature reactions.[65]
Physics
Under ultraviolet light, acetone fluoresces. Fluid flow experiments use its vapor as a tracer.[66]
Biology
Proteins precipitate in acetone.[67] The chemical modifies peptides, both at α- or ε-amino groups, and in a poorly understood but rapid modification of certain glycine residues.[67]
Acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.[72] It has been hypothesized that the high-fat low-carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain.[72] Because of their higher energy requirements, children have higher acetone production than most adults – and the younger the child, the higher the expected production. This indicates that children are not uniquely susceptible to acetone exposure. External exposures are small compared to the exposures associated with the ketogenic diet.[73]
Domestic and other niche uses
Make-up artists use acetone to remove skin adhesive from the netting of wigs and mustaches by immersing the item in an acetone bath, then removing the softened glue residue with a stiff brush.[74] Acetone is a main ingredient in many nail polish removers because it breaks down nail polish.[75] It is used for all types of nail polish removal, like gel nail polish, dip powder and acrylic nails.[76]
Acetone is often used for vapor polishing of printing artifacts on 3D-printed models printed with ABS plastic. The technique, called acetone vapor bath smoothing, involves placing the printed part in a sealed chamber containing a small amount of acetone, and heating to around 80 degrees Celsius for ten minutes. This creates a vapor of acetone in the container. The acetone condenses evenly all over the part, causing the surface to soften and liquefy. Surface tension then smooths the semi-liquid plastic. When the part is removed from the chamber, the acetone component evaporates leaving a glassy-smooth part free of striation, patterning, and visible layer edges, common features in untreated 3D printed parts.[77]
Acetone efficiently removes felt-tipped pen marks from glass and metals.
Safety
Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a dull blue flame; in larger amounts, fuel evaporation causes incomplete combustion and a bright yellow flame. When hotter than acetone's flash point of −20 °C (−4 °F), air mixtures of 2.5‑12.8% acetone (by volume) may explode or cause a flash fire. Vapors can flow along surfaces to distant ignition sources and flash back.
Static discharge may also ignite acetone vapors, though acetone has a very high ignition initiation energy and accidental ignition is rare.[78] Acetone's auto-ignition temperature is the relatively high 465 °C (869 °F);[19] moreover, auto-ignition temperature depends upon experimental conditions, such as exposure time, and has been quoted as high as 535 °C.[79] Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high vapour concentration and the cooling effect of evaporation.[78]
Acetone occurs naturally as part of certain metabolic processes in the human body, and has been studied extensively and is believed to exhibit only slight toxicity in normal use. There is no strong evidence of chronic health effects if basic precautions are followed.[83] It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.[84] Acetone is not currently regarded as a carcinogen, a mutagen, or a concern for chronic neurotoxicity effects.[78]
Acetone can be found as an ingredient in a variety of consumer products ranging from cosmetics to processed and unprocessed foods. Acetone has been rated as a generally recognized as safe (GRAS) substance when present in drinks, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L.[84]
Acetone is however an irritant, causing mild skin and moderate-to-severe eye irritation. At high vapor concentrations, it may depress the central nervous system like many other solvents.[85] Acute toxicity for mice by ingestion (LD50) is 3 g/kg, and by inhalation (LC50) is 44 g/m3 over 4 hours.[86]
Environmental effects
Although acetone occurs naturally in the environment in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat,[87] the majority of the acetone released into the environment is of industrial origin.[clarification needed] Acetone evaporates rapidly, even from water and soil. Once in the atmosphere, it has a 22-day half-life and is degraded by UV light via photolysis (primarily into methane and ethane.[88]) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.[87]
EPA classification
In 1995, the United States Environmental Protection Agency (EPA) removed acetone from the list of volatile organic compounds. The companies requesting the removal argued that it would "contribute to the achievement of several important environmental goals and would support EPA's pollution prevention efforts", and that acetone could be used as a substitute for several compounds that are listed as hazardous air pollutants (HAP) under section 112 of the Clean Air Act.[89] In making its decision EPA conducted an extensive review of the available toxicity data on acetone, which was continued through the 2000s. It found that the evaluable "data are inadequate for an assessment of the human carcinogenic potential of acetone".[9]
^ abcdAcetone in Linstrom, Peter J.; Mallard, William G. (eds.); NIST Chemistry WebBook, NIST Standard Reference Database Number 69, National Institute of Standards and Technology, Gaithersburg (MD)
^Chiang, Yvonne; Kresge, A. Jerry; Tang, Yui S.; Wirz, Jakob (1984). "The pKa and keto-enol equilibrium constant of acetone in aqueous solution". Journal of the American Chemical Society. 106 (2): 460–462. doi:10.1021/ja00314a055.
^Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004. S2CID26624076.
^Allen, P .W.; Bowen, H. J. M.; Sutton, L. E.; Bastiansen, O. (1952). "The molecular structure of acetone". Transactions of the Faraday Society. 48: 991. doi:10.1039/TF9524800991.
^ abcAcetone, World Petrochemicals report, January 2010
^ abcdefStylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
^C. Reichenbach (1834) "Ueber Mesit (Essiggeist) und Holzgeist" (On mesit (spirit of vinegar) and wood spirits), Annalen der Pharmacie, vol. 10, no. 3, pages 298–314.
^ abGreiner, Camara; Funada, C (June 2010). "CEH Marketing Research Report: ACETONE". Chemical Economics Handbook. SRI consulting. Retrieved 2 September 2016.(subscription required)
^Driessen, W.L.; Groeneveld, W.L. (1969). "Complexes with ligands containing the carbonyl group. Part I: Complexes with acetone of some divalent metals containing tetrachloro-ferrate(III) and -indate(III) anions". Recueil des Travaux Chimiques des Pays-Bas. 88 (8): 77977–988. doi:10.1002/recl.19690880811.
^ abcCataldo, Franco (1996). "Synthesis of ketonic resins from self-polymerization of acetone, 1 Action of protic and Lewis acids on acetone". Die Angewandte Makromolekulare Chemie. 236 (1): 1–19. doi:10.1002/apmc.1996.052360101.
^Kargin, V. A.; Kabanov, V. A.; Zubov, V. P.; Papisov, I. M. (1960). "Polymerisation of acetone". Doklady Akademii Nauk SSSR. 134 (5): 1098–1099.
^Addison, Ault (1998). Studyguide for Techniques and Experiments for Organic Chemistry. Sausalito, CA. p. 310. ISBN9780935702767.{{cite book}}: CS1 maint: location missing publisher (link)
^ abSimpson, Deborah M.; Beynon, Robert J. (2009-12-14). "Acetone Precipitation of Proteins and the Modification of Peptides". Journal of Proteome Research. 9 (1). American Chemical Society (ACS): 444–450. doi:10.1021/pr900806x. ISSN1535-3893. PMID20000691.
^Davis, Gretchen; Hall, Mindy (2012). The makeup artist handbook : techniques for film, television, photography, and theatre. Waltham, MA: Focal Press. p. 3. ISBN978-0-240-81894-8. OCLC776632427.
^"Acetone". Chemical Safety Facts. Retrieved 2024-05-27.
^ abAcetone, Agency for Toxic Substances and Disease Registry ToxFAQs, 1995
^Darwent, B. deB.; Allard, M. J.; Hartman, M. F.; Lange, L. J. (1960). "The Photolysis of Acetone". Journal of Physical Chemistry. 64 (12): 1847–1850. doi:10.1021/j100841a010.
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