Acetone[1]
IUPAC name	Propanone
Other names	β-ketopropane Dimethyl ketone,
Identifiers
CAS number	[67-64-1]
RTECS number	AL31500000
SMILES	CC(=O)C
InChI	1/C3H6O/c1-3(2)4/h1-2H3
Properties
Molecular formula	CH3COCH3
Molar mass	58.08 g/mol
Appearance	Colorless liquid
Density	0.79 g/cm³, liquid
Melting point	−94.9 °C (178.2 K) Image File history File links Download high resolution version (681x679, 6 KB) Summary Description: Skeletal formula of acetone (CH3COCH3). ... Image File history File links Size of this preview: 796 × 600 pixelsFull resolution (1100 × 829 pixel, file size: 119 KB, MIME type: image/png) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Acetone ... Image File history File links Download high-resolution version (1100x942, 164 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Acetone User:Benjah-bmm27/Gallery User:Ben Mills/Gallery ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The IUPAC International Chemical Identifier (InChI), developed by IUPAC and NIST, is a digital equivalent of the IUPAC name for any particular covalent compound. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...
Boiling point	56.53 °C (329.4 K) Italic text This article is about the boiling point of liquids. ...
Solubility in water	miscible
Viscosity	0.32 cP at 20 °C
Structure
Molecular shape	trigonal planar at C=O
Dipole moment	2.91 D
Hazards
MSDS	External MSDS
EU classification	Flammable (F) Irritant (Xi)
NFPA 704	3 1 0
R-phrases	R11, R36, R66, R67
S-phrases	(S2), S9, S16, S26
Flash point	-18 °C
Autoignition temperature	465 °C
Related compounds
Related solvents	Water Ethanol Isopropanol Toluene
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is a colorless, mobile, flammable liquid. It is the simplest example of the ketones. Acetone is miscible with water, ethanol, ether, etc., and itself serves as an important solvent. The most familiar household use of acetone is as the active ingredient in nail polish remover and paint thinner. Acetone is also used to make plastic, fibers, drugs, and other chemicals. In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body. Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... For other uses, see Viscosity (disambiguation). ... The poise (P; IPA: ) is the unit of dynamic viscosity in the centimetre gram second system of units. ... Four sp3 orbitals. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... This page provides supplementary chemical data on acetone. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main European Union law concerning chemical safety. ... Flammable or Flammability refers to the ease at which a substance will ignite, causing fire or combustion. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... For other uses, see Flash point (disambiguation). ... The autoignition temperature, or the ignition temperature of a substance is the lowest temperature at which a chemical will spontaneously ignite in a normal atmosphere, without an external source of ignition, such as a flame or spark. ... For other uses, see Solvent (disambiguation). ... H2O and HOH redirect here. ... Grain alcohol redirects here. ... Isopropyl alcohol or isopropanol is a common name for 2-propanol, an alcohol commonly used for application to the skin, and popularly referred to as rubbing alcohol. ... Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ... This page provides supplementary chemical data on acetone. ... This page provides supplementary chemical data on acetone. ... The refractive index (or index of refraction) of a medium is a measure for how much the speed of light (or other waves such as sound waves) is reduced inside the medium. ... The relative dielectric constant of a material under given conditions is a measure of the extent to which it concentrates electrostatic lines of flux. ... This page provides supplementary chemical data on acetone. ... This page provides supplementary chemical data on acetone. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... Infrared spectroscopy (IR spectroscopy) is the subset of spectroscopy that deals with the infrared region of the electromagnetic spectrum. ... Nuclear magnetic resonance spectroscopy most commonly known as NMR spectroscopy is the name given to the technique which exploits the magnetic properties of certain nuclei. ... Mass spectrometry (previously called mass spectroscopy (deprecated) or informally, mass-spec and MS) is an analytical technique that measures the mass-to-charge ratio of ions. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... Ketone group A ketone (pronounced as key tone) is either the functional group characterized by a carbonyl group (O=C) linked to two other carbon atoms or a chemical compound that contains this functional group. ... The chemistry term miscible refers to the property of various liquids that allows them to be mixed together. ... H2O and HOH redirect here. ... Grain alcohol redirects here. ... This article is about the chemical compound. ... For other uses, see Solvent (disambiguation). ... In chemistry, acetone (also known as propanone, dimethyl ketone, 2-propanone, propan-2-one and β-ketopropane) is the simplest representative of the ketones. ... Turpentine substitute is a mineral based replacement for the vegetable based organic solvent turpentine. ... For other uses, see Plastic (disambiguation). ...

Production

Acetone is produced primarily in the cumene process. Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate. During World War I a new process of producing acetone through bacterial fermentation was developed by Chaim Weizmann, later the first president of Israel, in order to help the British war effort. This Acetone Butanol Ethanol process was abandoned due to the small yield of Acetone Butanol compared to the organic waste. Cumene process is an industrial process of producing phenol (C6H5-OH) and acetone (CH3-CO-CH3) from benzene (C6H6) and propene (C3H6). ... Dry distillation is the heating of solid materials to produce liquid or gaseous products (which may condense into solids). ... For other uses, see Acetate (disambiguation). ... The chemical compound calcium acetate is the calcium salt of acetic acid. ... “The Great War ” redirects here. ... Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... For other uses, see Fermentation. ... Chaim Azriel Weizmann (Hebrew: חיים עזריאל ויצמן) November 27, 1874 – November 9, 1952) was a chemist, statesman, President of the World Zionist Organization, first President of Israel (elected February 1, 1949, served 1949 - 1952) and founder of a research institute in Israel that eventually became the Weizmann Institute of Science. ... Clostridium acetobutylicum () is a commercially valuable bacterium, included in the genus Clostridium. ... Butanol or butyl alcohol (sometimes also called biobutanol when produced biologically), is an alcohol with a 4 carbon structure and the molecular formula of C4H10O. It is primarily used as a solvent, as an intermediate in chemical synthesis, and as a fuel. ...

Biosynthesis

See also: ketosis

Small amounts of acetone are produced in the body by the decarboxylation of ketone bodies. Ketosis (IPA pronunciation: ) is a stage in metabolism occurring when the liver converts fat into fatty acids and ketone bodies which can be used by the body for energy. ... A Decarboxylation is any chemical reaction in which a carboxyl group (-COOH) is split off from a compound as carbon dioxide (CO2). ... Ketone bodies are three chemicals that are produced as by-products when fatty acids are broken down for energy. ...

Uses

Cleaning fluid

Acetone is often the primary (or only) component in nail polish remover. Ethyl acetate, another organic solvent, is sometimes used as well. Acetone is also used as a superglue remover. It can be used for thinning and cleaning fiberglass resins and epoxies. It is a strong solvent for most plastics and synthetic fibres. Pink nail polish. ... R-phrases , , , S-phrases , , Flash point −4 °C Related Compounds Related carboxylate esters Methyl acetate, Butyl acetate Related compounds Acetic acid, ethanol Supplementary data page Structure and properties n, εr, etc. ... Cyanoacrylate is the generic name for substances such as methyl-2-cyanoacrylate, which is usually sold under the trademarks Superglue and Krazy Glue, and 2-octyl cyanoacrylate, which is used in medical glues such as Dermabond and Traumaseal. ...

It is ideal for thinning fiberglass resin, cleaning fiberglass tools and dissolving two-part epoxies and superglue before hardening. A heavy-duty degreaser, it is useful in the preparation of metal prior to painting; it also thins polyester resins, vinyl and adhesives. It easily removes residues from glass and porcelain. In biological research contexts, buffers that contain acetone (such as citrate-buffered formalin) use the acetone to lyse cells for further experimentation. In chemistry, epoxy or polyepoxide is a thermosetting epoxide polymer that cures (polymerizes and crosslinks) when mixed with a catalyzing agent or hardener. Most common epoxy resins are produced from a reaction between epichlorohydrin and bisphenol-A. The first commercial attempts to prepare resins from epichlorohydrin occurred in 1927 in... Cyanoacrylate is the generic name for substances such as methyl-2-cyanoacrylate, which is usually sold under the trademarks Superglue and Krazy Glue, and 2-octyl cyanoacrylate, which is used in medical glues such as Dermabond and Traumaseal. ... This article is about the biological definition of the word Lysis. ...

Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers.

Solvent

Acetone can also dissolve many plastics, including those used in Nalgene bottles made of polystyrene, polycarbonate and some types of polypropylene.^[2] Nalgene (sometimes referred to as Nalge Nunc International) is a distributor and manufacturer of plastic laboratory containers that has diversified into the field of containers for outdoor sports. ...

In the laboratory, acetone is used as a polar aprotic solvent in a variety of organic reactions, such as S_N2 reactions. The use of acetone solvent is also critical for the successful Jones oxidation. Technical grade acetone is inexpensive. Because of acetone's medium polarity, it dissolves a wide range of compounds. Thus, it is commonly loaded into squeezebottles and used as a general solvent in rinsing laboratory glassware. A commonly-used example of a polar compound is water (H2O). ... In chemistry any solvent that carries hydrogen attached to oxygen as in a hydroxyl group or nitrogen as in a amine group is called a protic solvent. ... Organic reactions are chemical reactions involving organic compounds. ... Structure of the SN2 transition state The SN2 reaction (also known as bimolecular substitution nucleophilic) is a type of nucleophilic substitution, where a lone pair from a nucleophile attacks an electron deficient electrophilic center and bonds to it, expelling another group called a leaving group. ... The Jones oxidation is a chemical reaction described as the chromic acid oxidation of primary and secondary alcohols to carboxylic acids and ketones, respectively. ... Brown glass jars with some clear lab glassware in the background Laboratory glassware refers to a variety of equipment, traditionally made of glass, used for scientific experiments and other work in science, especially in chemistry and biology laboratories. ...

Acetone is also used extensively for the safe transporting and storing of acetylene. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One liter of acetone can dissolve around 250 liters of acetylene. Acetylene (systematic name: ethyne) is a hydrocarbon belonging to the group of alkynes. ...

Feedstock

An important industrial use for acetone involves its reaction with phenol for the manufacture of bisphenol A. Bisphenol A is an important component of many polymers such as polycarbonates, polyurethanes and epoxy resins. Acetone has also been used in the manufacture of cordite. Phenol, also known under an older name of carbolic acid, is a colourless crystalline solid with a typical sweet tarry odor. ... This article needs to be wikified. ... Polycarbonates are a particular group of thermoplastic polyesters. ... A polyurethane is any polymer consisting of a chain of organic units joined by urethane links. ... Epoxy or polyepoxide is a thermosetting epoxide polymer that cures when mixed with a catalyzing agent or hardener. Most common epoxy resins are produced from a reaction between Epichorohydrin & Bisphenol A. The first commercial attempts to prepare resins from epichlorohydrin occurred in 1927 in the United States. ... Cordite is a family of smokeless propellants developed and produced in the United Kingdom from the late 19th Century to replace gunpowder as a military propellant for large weapons, such as tank guns, artillery and naval guns. ...

Automotive fuel additive

Some automotive enthusiasts add acetone at around 1 part in 500 to their fuel, following claims of dramatic improvement in fuel economy and engine life.^[3] This practice is controversial as there are counterclaims that acetone has no measurable effect or may in fact reduce engine life by adversely affecting fuel system parts.^[4][5][6] Debates on this subject and claims of Big Oil cover-up intensified when the practice was addressed on the popular American TV show MythBusters in 2006, and shown to have negative effect in the televised fuel economy test.^[7]. MythBusters is an American popular science television program on the Discovery Channel starring American special effects experts Adam Savage and Jamie Hyneman, who use basic elements of the scientific method to test the validity of various rumors, urban legends and news stories in popular culture. ...

Some cars that are prone to incomplete fuel burning because they are badly tuned or getting old (clogged carburator, air filter or fuel line, etc.) may experience improvement of fuel consumption because acetone will act as a parts cleaner and dessicant by adsorbing water present in fuel. To expect any fuel consumption benefits, the acetone or any high octane fuel additive (ethanol, etc.) would have to be put in a higher compression ratio engine. Since only the compression ratio can make any energy efficiency difference in a carefully tuned engine. So only a volume reduction of the combustion room when the piston is in the max compression position would make a more efficient thermodynamic cycle and better fuel consumption. A tuned compression ratio engine would then requires only high octane fuel to avoid self fuel ignition by pressure (engine knocking).^{[citation needed]}

Other uses

Acetone is also used as a drying agent, due to the readiness with which it mixes with water, and its volatility. A desiccant is a substance that adsorbs moisture from the air. ...

It can be used as an artistic agent; when rubbed on the back of a laser print or photocopy placed face-down on another surface and burnished firmly, the toner of the image is allowed to transfer to the destination surface.

Safety

Acetone peroxide

Main article: acetone peroxide

When oxidized, acetone forms acetone peroxide as a by-product, which is a highly unstable compound. It may be formed accidentally, e.g. when waste hydrogen peroxide is poured into a carboy containing waste acetone solvent. Acetone peroxide is more than ten times as friction and shock sensitive as nitroglycerin. Due to its unstability, it is rarely used, despite its easy chemical synthesis. Acetone peroxide Ball-and-stick model of the acetone peroxide trimer (TATP) Acetone peroxide (triacetone triperoxide, peroxyacetone, TATP, TCAP) is an organic peroxide and a primary high explosive. ... R-phrases , , , , S-phrases , , , , , , , , Flash point Non-flammable Related Compounds Related compounds Water Ozone Hydrazine Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Hydrogen peroxide (H2O2) is a very pale blue liquid which appears colorless in... Nitroglycerin (NG), also known as nitroglycerine, trinitroglycerin, and glyceryl trinitrate, is a chemical compound. ...

Toxicology

Acetone is an irritant and inhalation may lead to hepatotoxic effects (causing liver damage). The vapors should be avoided. In no circumstance should it be consumed directly or indirectly. Always use goggles when handling acetone; it can cause permanent eye damage (corneal clouding). Hepatotoxicity (from hepatic toxicity) is chemical-driven liver damage. ...

Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production (see ketosis). Acetone can be elevated in diabetes. Contamination of water, food (e.g. milk), or the air (acetone is volatile) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Relatively speaking, acetone is not a very toxic compound; it can, however, damage the mucosa of the mouth and can irritate and damage skin. Accidental intake of large amounts of acetone may lead to unconsciousness and death. Ketosis (IPA pronunciation: ) is a stage in metabolism occurring when the liver converts fat into fatty acids and ketone bodies which can be used by the body for energy. ... This article is about the disease that features high blood sugar. ... The mucous membranes (or mucosa) are linings of ectodermic origin, covered in epithelium, that line various body cavities and internal organs. ... For other uses, see Mouth (disambiguation). ...

The effects of long-term exposure to acetone are known mostly from animal studies. Kidney, liver, and nerve damage, increased birth defects, and lowered reproduction ability of males (only) occurred in animals exposed long-term. It is not known if these same effects would be exhibited in humans. Pregnant women should avoid contact with acetone and acetone fumes in order to avoid the possibility of birth defects, including brain damage. The kidneys are the organs that filter wastes (such as urea) from the blood and excrete them, along with water, as urine. ... The liver is the largest internal organ in the human body, and is an organ present in vertebrates and some other animals. ... For other uses, see Nerve (disambiguation). ... A congenital disorder is a medical condition or defect that is present at or before birth (for example, congenital heart disease). ...

Interestingly, acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations.^[8] 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.^[8] The anticonvulsants, sometimes also called antiepileptics, belong to a diverse group of pharmaceuticals used in prevention of the occurrence of epileptic seizures. ... The ketogenic diet is a very high fat diet that relies on inducing a state of ketosis. ...

References

1. ^ Merck Index, 11th Edition, 58.
2. ^ NALGENE Labware - Technical Data
3. ^ Louis LaPonte (2007-02-13). Acetone in Fuels (A Study of Dimethylketone or Propanone). Smartgas.net. Retrieved on 2007-06-06.
4. ^ Acetone as a Fuel Additive. Pure Energy Systems Wiki. Retrieved on 2007-06-06.
5. ^ Tom and Ray Magliozzi (2006-01-21). Click and Clack Talk Cars. Independent Record. Retrieved on 2007-06-06.
6. ^ Can adding Acetone to fuel increase mpg by 15 to 35%?. Snopes.com Message Board. Retrieved on 2007-06-06.
7. ^ MythBusters (Season 4, Episode 53)
8. ^ ^{a b} Likhodii SS, Serbanescu I, Cortez MA, Murphy P, Snead OC 3rd, Burnham WM (2003). "Anticonvulsant properties of acetone, a brain ketone elevated by the ketogenic diet". Ann Neurol. 54 (2): 219–226. doi:10.1002/ana.10634. 

Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 44th day of the year in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 157th day of the year (158th in leap years) in the Gregorian calendar. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 157th day of the year (158th in leap years) in the Gregorian calendar. ... Year 2006 (MMVI) was a common year starting on Sunday of the Gregorian calendar. ... is the 21st day of the year in the Gregorian calendar. ... The Independent Standard is a daily newspaper printed in Helena, Montana. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 157th day of the year (158th in leap years) in the Gregorian calendar. ... Snopes, also known as the Urban Legends Reference Pages, is a website dedicated to determining the truth about many urban legends, Internet rumors, email forwards, and other such stories of uncertain or questionable origin. ... Year 2007 (MMVII) is the current year, a common year starting on Monday of the Gregorian calendar and the AD/CE era in the 21st century. ... is the 157th day of the year (158th in leap years) in the Gregorian calendar. ... MythBusters is an American popular science television program on the Discovery Channel starring American special effects experts Adam Savage and Jamie Hyneman, who use basic elements of the scientific method to test the validity of various rumors, urban legends and news stories in popular culture. ... Wikiquote has a collection of quotations related to: MythBusters The cast/crew of the television series MythBusters performs experiments to verify or debunk urban legends, old wives tales, and the like. ... A digital object identifier (or DOI) is a standard for persistently identifying a piece of intellectual property on a digital network and associating it with related data, the metadata, in a structured extensible way. ...

External links

• International Chemical Safety Card 0087
• National Pollutant Inventory – Acetone
• NIOSH Pocket Guide to Chemical Hazards