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Wikipedia

Acetone

January 01, 1970

Not to be confused with Acetoin.
For the musical instrument company, see Ace Tone.

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.

Acetone[1]
Full structural formula of acetone with dimensions
Skeletal formula of acetone
Ball-and-stick model of acetone
Space-filling model of acetone
Names
IUPAC name
Acetone[7]
Preferred IUPAC name
Propan-2-one[8]
Systematic IUPAC name
2-Propanone
Other names
  • Acetonum (Latin pronunciation: [aˈkeːtonum])
  • Dimethyl ketone[2]
  • Dimethyl carbonyl
  • Ketone propane[3]
  • β-Ketopropane[2]
  • Propanone[4]
  • 2-Propanone[2]
  • Pyroacetic spirit (archaic)[5]
  • Spirit of Saturn (archaic)[6]
Identifiers
  • 67-64-1 Y
3D model (JSmol)
  • Interactive image
3DMet
  • B00058
635680
ChEBI
  • CHEBI:15347 Y
ChEMBL
  • ChEMBL14253 Y
ChemSpider
  • 175 Y
ECHA InfoCard 100.000.602
EC Number
  • 200-662-2
1466
KEGG
  • D02311 Y
MeSH Acetone
  • 180
RTECS number
  • AL3150000
UNII
  • 1364PS73AF Y
UN number 1090
  • DTXSID8021482
  • InChI=1S/C3H6O/c1-3(2)4/h1-2H3 Y
    Key: CSCPPACGZOOCGX-UHFFFAOYSA-N Y
  • InChI=1/C3H6O/c1-3(2)4/h1-2H3
    Key: CSCPPACGZOOCGX-UHFFFAOYAF
  • CC(=O)C
Properties
C3H6O
Molar mass 58.080 g·mol−1
Appearance Colourless liquid
Odor Pungent, fruity[9]
Density 0.7845 g/cm3 (25 °C)[10]
Melting point −94.9 °C (−138.8 °F; 178.2 K)[10]
Boiling point 56.08 °C (132.94 °F; 329.23 K)[10]
Miscible[10]
Solubility Miscible in benzene, diethyl ether, methanol, chloroform, ethanol[10]
log P −0.24[11]
Vapor pressure
  • 9.39 kPa (0 °C)
  • 30.6 kPa (25 °C)
  • 374 kPa (100 °C)
  • 2.8 MPa (200 °C)[2]
Acidity (pKa)
−33.8·10−6 cm3/mol[14]
Thermal conductivity 0.161 W/(m·K) (25 °C)[15]
1.3588 (20 °C)[10]
Viscosity 0.306 mPa·s (25 °C)[16]
Structure
Trigonal planar at C2
Dihedral at C2
2.88 D[17]
Thermochemistry[18]
126.3 J/(mol·K)
199.8 J/(mol·K)
−248.4 kJ/mol
−1.79 MJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Highly flammable
GHS labelling:
Danger
H225, H302, H319, H336, H373
P210, P235, P260, P305+P351+P338
NFPA 704 (fire diamond)
Health 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 −20 °C (−4 °F; 253 K)[19]
465[19] °C (869 °F; 738 K)
Explosive limits 2.5–12.8%[19]
250 ppm[20] (STEL), 500 ppm[20] (C)
Lethal dose or concentration (LD, LC):
  • 5800 mg/kg (rat, oral)
  • 3000 mg/kg (mouse, oral)
  • 5340 mg/kg (rabbit, oral)[21]
20,702 ppm (rat, 8 h)[21]
45,455 ppm (mouse, 1 h)[21]
NIOSH (US health exposure limits):
PEL (Permissible)
 1000 ppm (2400 mg/m3)[3]
REL (Recommended)
 TWA 250 ppm (590 mg/m3)[3]
IDLH (Immediate danger)
 2500 ppm[3]
Related compounds
Related compounds
Supplementary data page
Acetone (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)

Acetone is miscible with water and serves as an important organic solvent in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and for production of methyl methacrylate and bisphenol A, which are precursors to widely used plastics.[23][24] It is a common building block in organic chemistry. It serves as a solvent in household products such as nail polish remover and paint thinner. It has volatile organic compound (VOC)-exempt status in the United States.[25]

Acetone is produced and disposed of in the human body through normal metabolic processes. It is normally present in blood and urine. People with diabetic ketoacidosis produce it in larger amounts. Ketogenic diets that increase ketone bodies (acetone, β-hydroxybutyric acid and acetoacetic acid) in the blood are used to counter epileptic attacks in children who suffer from refractory epilepsy.[26]

Name edit

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]

Prior to the "acetone" name given by Antoine Bussy, it was named "mesit" (from the Greek μεσίτης, meaning mediator) by Carl Reichenbach who also claimed that methyl alcohol consisted of mesit and ethyl alcohol.[27][6] Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone.

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]

History edit

Acetone was first produced by Andreas Libavius in 1606 by distillation of lead(II) acetate.[29][30]

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 edit

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 edit

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]

Older methods edit

Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate in ketonic decarboxylation.

 

After that time, during World War I, acetone was produced using acetone-butanol-ethanol fermentation with Clostridium acetobutylicum bacteria, which was developed by Chaim Weizmann (later the first president of Israel) in order to help the British war effort,[24] in the preparation of Cordite.[43] This acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found.[24]

Chemical properties edit

The flame temperature of pure acetone is 1980 °C.[44]

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 edit

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 infrared absorption 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 edit

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]

Metabolism edit

Acetone can then be metabolized either by CYP2E1 via methylglyoxal to D-lactate and pyruvate, and ultimately glucose/energy, or by a different pathway via propylene glycol to pyruvate, lactate, acetate (usable for energy) and propionaldehyde.[54][55][56]

Uses edit

Industrial edit

About a third of the world's acetone is used as a solvent, and a quarter is consumed as acetone cyanohydrin, a precursor to methyl methacrylate.[23]

Solvent edit

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]

Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol.[60] Acetone is also present as an excipient in some pharmaceutical drugs.[61][needs update]

Chemical intermediate edit

Acetone is used to synthesize methyl methacrylate. It begins with the initial conversion of acetone to acetone cyanohydrin via reaction with hydrogen cyanide (HCN):

 

In a subsequent step, the nitrile is hydrolyzed to the unsaturated amide, which is esterified:

 

The third major use of acetone (about 20%)[23] is synthesizing bisphenol A. Bisphenol A is a component of many polymers such as polycarbonates, polyurethanes, and epoxy resins. The synthesis involves the condensation of acetone with phenol:

 

Many millions of kilograms of acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone. These products arise via an initial aldol condensation to give diacetone alcohol.[24]

 

Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic terpenes and terpenoids.[62]

Laboratory edit

Chemistry edit

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 a low-temperature reactions.[65]

Physics edit

Under ultraviolet light, acetone fluoresces. Fluid flow experiments use its vapor as a tracer.[66]

Biology edit

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]

In pathology, acetone helps find lymph nodes in fatty tissues (such as the mesentery) for tumor staging.[68] The liquid dissolves the fat and hardens the nodes, making them easier to find.[69]

Acetone also removes certain stains from microscope slides.[70]

Medical edit

Dermatologists use acetone with alcohol for acne treatments to chemically peel dry skin. Common agents used today for chemical peeling are salicylic acid, glycolic acid, azelaic acid, 30% salicylic acid in ethanol, and trichloroacetic acid (TCA). Prior to chemexfoliation, the skin is cleaned and excess fat removed in a process called defatting. Acetone, hexachlorophene, or a combination of these agents was used in this process.[71]

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 edit

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 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.[75]

Acetone efficiently removes felt-tipped pen marks from glass and metals.

Safety edit

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.[76] 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.[77] 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.[76]

Acetone should be stored away from strong oxidizers, such as concentrated nitric and sulfuric acid mixtures.[78] It may also explode when mixed with chloroform in the presence of a base.[79][clarification needed] When oxidized without combustion, for example with hydrogen peroxide, acetone may form acetone peroxide, a highly unstable primary explosive. Acetone peroxide may be formed accidentally, e.g. when waste peroxide is poured into waste solvents.[80]

Toxicity edit

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.[81] It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled.[82] Acetone is not currently regarded as a carcinogen, a mutagen, or a concern for chronic neurotoxicity effects.[76]

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.[82]

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.[83] Acute toxicity for mice by ingestion (LD50) is 3 g/kg, and by inhalation (LC50) is 44 g/m3 over 4 hours.[84]

Environmental effects edit

Although acetone occurs naturally in the environment in plants, trees, volcanic gases, forest fires, and as a product of the breakdown of body fat,[85] 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.[86]) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways.[85]

EPA classification edit

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.[87] 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]

Extraterrestrial occurrence edit

On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67P's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which were seen for the first time on a comet, including acetamide, acetone, methyl isocyanate, and propionaldehyde.[88][89][90]

References edit

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Common sources edit

Further reading edit

 
Wikimedia Commons has media related to Acetone.
  • International Chemical Safety Card 0087
  • NIOSH Pocket Guide to Chemical Hazards
  • Hazardous substances databank entry at the national library of medicine 2018-12-04 at the Wayback Machine
  • SIDS Initial Assessment Report for Acetone from the Organisation for Economic Co-operation and Development (OECD)
  • Calculation of vapor pressure, liquid density, dynamic liquid viscosity, surface tension of acetone

January 01, 1970
acetone, confused, with, acetoin, musical, instrument, company, tone, propanone, dimethyl, ketone, organic, compound, with, formula, simplest, smallest, ketone, colorless, highly, volatile, flammable, liquid, with, characteristic, pungent, odor, full, structur. Not to be confused with Acetoin For the musical instrument company see Ace Tone Acetone 2 propanone or dimethyl ketone is an organic compound with the formula CH3 2CO 22 It is the simplest and smallest ketone gt C O It is a colorless highly volatile and flammable liquid with a characteristic pungent odor Acetone 1 Full structural formula of acetone with dimensions Skeletal formula of acetone Ball and stick model of acetone Space filling model of acetone Names IUPAC name Acetone 7 Preferred IUPAC name Propan 2 one 8 Systematic IUPAC name 2 Propanone Other names Acetonum Latin pronunciation aˈkeːtonum Dimethyl ketone 2 Dimethyl carbonyl Ketone propane 3 b Ketopropane 2 Propanone 4 2 Propanone 2 Pyroacetic spirit archaic 5 Spirit of Saturn archaic 6 Identifiers CAS Number 67 64 1 Y 3D model JSmol Interactive image 3DMet B00058 Beilstein Reference 635680 ChEBI CHEBI 15347 Y ChEMBL ChEMBL14253 Y ChemSpider 175 Y ECHA InfoCard 100 000 602 EC Number 200 662 2 Gmelin Reference 1466 KEGG D02311 Y MeSH Acetone PubChem CID 180 RTECS number AL3150000 UNII 1364PS73AF Y UN number 1090 CompTox Dashboard EPA DTXSID8021482 InChI InChI 1S C3H6O c1 3 2 4 h1 2H3 YKey CSCPPACGZOOCGX UHFFFAOYSA N YInChI 1 C3H6O c1 3 2 4 h1 2H3Key CSCPPACGZOOCGX UHFFFAOYAF SMILES CC O C Properties Chemical formula C 3H 6O Molar mass 58 080 g mol 1 Appearance Colourless liquid Odor Pungent fruity 9 Density 0 7845 g cm3 25 C 10 Melting point 94 9 C 138 8 F 178 2 K 10 Boiling point 56 08 C 132 94 F 329 23 K 10 Solubility in water Miscible 10 Solubility Miscible in benzene diethyl ether methanol chloroform ethanol 10 log P 0 24 11 Vapor pressure 9 39 kPa 0 C 30 6 kPa 25 C 374 kPa 100 C 2 8 MPa 200 C 2 Acidity pKa 19 16 H2O 12 26 5 DMSO 13 Magnetic susceptibility x 33 8 10 6 cm3 mol 14 Thermal conductivity 0 161 W m K 25 C 15 Refractive index nD 1 3588 20 C 10 Viscosity 0 306 mPa s 25 C 16 Structure Coordination geometry Trigonal planar at C2 Molecular shape Dihedral at C2 Dipole moment 2 88 D 17 Thermochemistry 18 Heat capacity C 126 3 J mol K Std molarentropy S 298 199 8 J mol K Std enthalpy offormation DfH 298 248 4 kJ mol Std enthalpy ofcombustion DcH 298 1 79 MJ mol Hazards Occupational safety and health OHS OSH Main hazards Highly flammable GHS labelling Pictograms Signal word Danger Hazard statements H225 H302 H319 H336 H373 Precautionary statements P210 P235 P260 P305 P351 P338 NFPA 704 fire diamond 130 Flash point 20 C 4 F 253 K 19 Autoignitiontemperature 465 19 C 869 F 738 K Explosive limits 2 5 12 8 19 Threshold limit value TLV 250 ppm 20 STEL 500 ppm 20 C Lethal dose or concentration LD LC LD50 median dose 5800 mg kg rat oral 3000 mg kg mouse oral 5340 mg kg rabbit oral 21 LC50 median concentration 20 702 ppm rat 8 h 21 LCLo lowest published 45 455 ppm mouse 1 h 21 NIOSH US health exposure limits PEL Permissible 1000 ppm 2400 mg m3 3 REL Recommended TWA 250 ppm 590 mg m3 3 IDLH Immediate danger 2500 ppm 3 Related compounds Related compounds ButanoneIsopropyl alcoholFormaldehydeUreaCarbonic acid Supplementary data page Acetone data page Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Y verify what is Y N Infobox references Acetone is miscible with water and serves as an important organic solvent in industry home and laboratory About 6 7 million tonnes were produced worldwide in 2010 mainly for use as a solvent and for production of methyl methacrylate and bisphenol A which are precursors to widely used plastics 23 24 It is a common building block in organic chemistry It serves as a solvent in household products such as nail polish remover and paint thinner It has volatile organic compound VOC exempt status in the United States 25 Acetone is produced and disposed of in the human body through normal metabolic processes It is normally present in blood and urine People with diabetic ketoacidosis produce it in larger amounts Ketogenic diets that increase ketone bodies acetone b hydroxybutyric acid and acetoacetic acid in the blood are used to counter epileptic attacks in children who suffer from refractory epilepsy 26 Contents 1 Name 2 History 3 Production 3 1 Current method 3 2 Older methods 4 Chemical properties 4 1 Polymerisation 5 Natural occurrence 5 1 Metabolism 6 Uses 6 1 Industrial 6 1 1 Solvent 6 1 2 Chemical intermediate 6 2 Laboratory 6 2 1 Chemistry 6 2 2 Physics 6 2 3 Biology 6 3 Medical 6 4 Domestic and other niche uses 7 Safety 7 1 Toxicity 7 2 Environmental effects 7 3 EPA classification 8 Extraterrestrial occurrence 9 References 9 1 Common sources 9 2 Further readingName editFrom 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 Prior to the acetone name given by Antoine Bussy it was named mesit from the Greek mesiths meaning mediator by Carl Reichenbach who also claimed that methyl alcohol consisted of mesit and ethyl alcohol 27 6 Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone 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 History editAcetone was first produced by Andreas Libavius in 1606 by distillation of lead II acetate 29 30 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 Frederic Gerhardt concurred 35 In 1865 the German chemist August Kekule 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 editIn 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 edit 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 nbsp 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 Older methods edit Previously acetone was produced by the dry distillation of acetates for example calcium acetate in ketonic decarboxylation Ca CH 3 COO 2 CaO s CO 2 g CH 3 2 CO displaystyle ce Ca CH3COO 2 gt CaO s CO2 g CH3 2CO v nbsp After that time during World War I acetone was produced using acetone butanol ethanol fermentation with Clostridium acetobutylicum bacteria which was developed by Chaim Weizmann later the first president of Israel in order to help the British war effort 24 in the preparation of Cordite 43 This acetone butanol ethanol fermentation was eventually abandoned when newer methods with better yields were found 24 Chemical properties editThe flame temperature of pure acetone is 1980 C 44 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 nbsp 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 edit 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 infrared absorption spectrum showed the presence of O linkages but no C O groups 51 However conflicting results were obtained later by other investigators 49 nbsp 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 editHumans 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 Metabolism edit Acetone can then be metabolized either by CYP2E1 via methylglyoxal to D lactate and pyruvate and ultimately glucose energy or by a different pathway via propylene glycol to pyruvate lactate acetate usable for energy and propionaldehyde 54 55 56 Uses editIndustrial edit About a third of the world s acetone is used as a solvent and a quarter is consumed as acetone cyanohydrin a precursor to methyl methacrylate 23 Solvent edit 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 Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol 60 Acetone is also present as an excipient in some pharmaceutical drugs 61 needs update Chemical intermediate edit Acetone is used to synthesize methyl methacrylate It begins with the initial conversion of acetone to acetone cyanohydrin via reaction with hydrogen cyanide HCN CH 3 2 CO HCN CH 3 2 C OH CN displaystyle ce CH3 2CO HCN gt CH3 2C OH CN nbsp In a subsequent step the nitrile is hydrolyzed to the unsaturated amide which is esterified CH 3 2 C OH CN CH 3 OH CH 2 C CH 3 CO 2 CH 3 NH 3 displaystyle ce CH3 2C OH CN CH3OH gt CH2 C CH3 CO2CH3 NH3 nbsp The third major use of acetone about 20 23 is synthesizing bisphenol A Bisphenol A is a component of many polymers such as polycarbonates polyurethanes and epoxy resins The synthesis involves the condensation of acetone with phenol CH 3 2 CO 2 C 6 H 5 OH CH 3 2 C C 6 H 4 OH 2 H 2 O displaystyle ce CH3 2CO 2 C6H5OH gt CH3 2C C6H4OH 2 H2O nbsp Many millions of kilograms of acetone are consumed in the production of the solvents methyl isobutyl alcohol and methyl isobutyl ketone These products arise via an initial aldol condensation to give diacetone alcohol 24 2 CH 3 2 CO CH 3 2 C OH CH 2 C O CH 3 displaystyle ce 2 CH3 2CO gt CH3 2C OH CH2C O CH3 nbsp Condensation with acetylene gives 2 methylbut 3 yn 2 ol precursor to synthetic terpenes and terpenoids 62 Laboratory edit Chemistry edit 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 a low temperature reactions 65 Physics edit Under ultraviolet light acetone fluoresces Fluid flow experiments use its vapor as a tracer 66 Biology edit Proteins precipitate in acetone 67 The chemical modifies peptides both at a or e amino groups and in a poorly understood but rapid modification of certain glycine residues 67 In pathology acetone helps find lymph nodes in fatty tissues such as the mesentery for tumor staging 68 The liquid dissolves the fat and hardens the nodes making them easier to find 69 Acetone also removes certain stains from microscope slides 70 Medical edit Dermatologists use acetone with alcohol for acne treatments to chemically peel dry skin Common agents used today for chemical peeling are salicylic acid glycolic acid azelaic acid 30 salicylic acid in ethanol and trichloroacetic acid TCA Prior to chemexfoliation the skin is cleaned and excess fat removed in a process called defatting Acetone hexachlorophene or a combination of these agents was used in this process 71 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 edit 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 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 75 Acetone efficiently removes felt tipped pen marks from glass and metals Safety editAcetone 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 76 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 77 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 76 Acetone should be stored away from strong oxidizers such as concentrated nitric and sulfuric acid mixtures 78 It may also explode when mixed with chloroform in the presence of a base 79 clarification needed When oxidized without combustion for example with hydrogen peroxide acetone may form acetone peroxide a highly unstable primary explosive Acetone peroxide may be formed accidentally e g when waste peroxide is poured into waste solvents 80 Toxicity edit 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 81 It is generally recognized to have low acute and chronic toxicity if ingested and or inhaled 82 Acetone is not currently regarded as a carcinogen a mutagen or a concern for chronic neurotoxicity effects 76 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 82 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 83 Acute toxicity for mice by ingestion LD50 is 3 g kg and by inhalation LC50 is 44 g m3 over 4 hours 84 Environmental effects edit Although acetone occurs naturally in the environment in plants trees volcanic gases forest fires and as a product of the breakdown of body fat 85 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 86 Consumption by microorganisms contributes to the dissipation of acetone in soil animals or waterways 85 EPA classification edit 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 87 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 Extraterrestrial occurrence editOn 30 July 2015 scientists reported that upon the first touchdown of the Philae lander on comet 67P s surface measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds four of which were seen for the first time on a comet including acetamide acetone methyl isocyanate and propionaldehyde 88 89 90 References edit The Merck Index 15th Ed 2013 p 13 Acetone Monograph 65 O Neil The Royal Society of Chemistry subscription required a b c d Acetone 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 a b c d NIOSH Pocket Guide to Chemical Hazards 0004 National Institute for Occupational Safety and Health NIOSH Klamt Andreas 2005 COSMO RS From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design Elsevier pp 92 94 ISBN 978 0 444 51994 8 Myers Richard L 2007 The 100 Most Important Chemical Compounds A Reference Guide Greenwood pp 4 6 ISBN 978 0 313 08057 9 a b c Mel Gorman History of acetone 1600 1850 1962 ChemSpider lists acetone as a valid expert verified name for what would systematically be called propan 2 one Nomenclature of Organic Chemistry IUPAC Recommendations and Preferred Names 2013 Blue Book Cambridge The Royal Society of Chemistry 2014 p 723 doi 10 1039 9781849733069 FP001 ISBN 978 0 85404 182 4 a b Toxicological Profile for Acetone U S Environmental Protection Agency June 2022 p 7 a b c d e f Haynes p 3 4 Haynes p 5 173 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 S2CID 26624076 Haynes p 3 576 Haynes p 6 254 Haynes p 6 243 Haynes p 9 60 Haynes pp 5 3 5 67 a b c d Haynes p 15 13 a b Haynes p 16 34 a b c Acetone Immediately Dangerous to Life or Health Concentrations IDLH National Institute for Occupational Safety and Health NIOSH 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 a b c Acetone World Petrochemicals report January 2010 a b c d e f Stylianos Sifniades Alan B Levy Acetone in Ullmann s Encyclopedia of Industrial Chemistry Wiley VCH Weinheim 2005 Update U S EPA Exempt Volatile Organic Compounds American Coatings Association 2018 01 30 Archived from the original on 2021 02 08 Retrieved 2019 03 20 Freeman JM Kossoff EH Hartman AL Mar 2007 The ketogenic diet one decade later Pediatrics 119 3 535 43 doi 10 1542 peds 2006 2447 PMID 17332207 S2CID 26629499 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 a b Acetone 28 September 2018 Libavius Andreas 1606 Alchymia in Latin Frankfurt Germany printed by Joannes Saurius at the expense of Peter Kopff p 123 Aceton Chemgapedia Dumas J 1832 Sur l esprit pyro acetique On pyro acetic spirit Annales de Chimie et de Physique 2nd series 49 208 210 Liebig Justus 1832 Sur les combinaisons produites par l action du gas olefiant et l esprit acetique On compounds produced by the action of ethylene and acetic spirit Annales de Chimie et de Physique 2nd series 49 146 204 especially 193 204 Bussy Antoine 1833 De quelques Produits nouveaux obtenus par l action des Alcalis sur les Corps gras a une haute temperature On some new products obtained by the action of alkalies on fatty substances at a high temperature Annales de Chimie et de Physique 2nd series 53 398 412 see footnote on pp 408 409 Williamson A W 1852 On Etherification Journal of the Chemical Society 4 229 239 especially pp 237 239 Gerhardt Charles 1853 Researches sur les acids organiques anhydres Research on anhydrous organic acids Annales de Chimie et de Physique 3rd series 37 285 342 see p 339 Kekule Auguste 1865 Sur la constitution des substances aromatiques Bulletin de la Societe chimique de Paris 1 98 110 especially p 110 Kekule Auguste 1866 Untersuchungen uber aromatischen Verbindungen Investigations into aromatic compounds Annalen der Chemie und Pharmacie 137 129 196 especially pp 143 144 Loschmidt J 1861 Chemische Studien Vienna Austria Hungary Carl Gerold s Sohn Chaim Weizmann chemistryexplained com a b Greiner Camara Funada C June 2010 CEH Marketing Research Report ACETONE Chemical Economics Handbook SRI consulting Retrieved 2 September 2016 subscription required Acetone Uses and Market Data ICIS com October 2010 Archived from the original on 2009 05 15 Retrieved 2011 03 21 Acetone US Gulf Price Report Chemical pricing information Archived 2013 05 16 at the Wayback Machine ICIS Pricing Retrieved on 2012 11 26 Wittcoff M M Green H A 2003 Organic chemistry principles and industrial practice 1 ed 1 reprint ed Weinheim Wiley VCH p 4 ISBN 3 527 30289 1 Haynes p 15 49 Hine Jack Arata Kazushi 1976 Keto Enol Tautomerism II The Calorimetrical Determination of the Equilibrium Constants for Keto Enol Tautomerism for Cyclohexanone and Acetone Bulletin of the Chemical Society of Japan 49 11 3089 3092 doi 10 1246 bcsj 49 3089 Sowa John R 2005 Catalysis of organic reactions Boca Raton Taylor amp Francis p 363 ISBN 978 0 8247 2729 1 OCLC 67767141 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 Kilner C A Halcrow M A 2006 An unusual example of a linearly coordinated acetone ligand in a six coordinate iron II complex Acta Crystallographica C 62 9 1107 1109 Bibcode 2006AcCrC 62M 437K doi 10 1107 S0108270106028903 PMID 16954630 a b c Cataldo 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 Kawai Wasaburo 1962 Polymerization of Acetone Bulletin of the Chemical Society of Japan 35 3 516A doi 10 1246 bcsj 35 516a a b Karch Steven B 1998 Drug abuse handbook Boca Raton Fla CRC Press p 369 ISBN 978 1 4200 4829 2 OCLC 61503700 Amann Anton Costello Ben de Lacy Miekisch Wolfram Schubert Jochen Buszewski Boguslaw Pleil Joachim Ratcliffe Norman Risby Terence 2014 The human volatilome Volatile organic compounds VOCs in exhaled breath skin emanations urine feces and saliva Journal of Breath Research 8 3 034001 Bibcode 2014JBR 8c4001A doi 10 1088 1752 7155 8 3 034001 PMID 24946087 S2CID 40583110 Glew Robert H 2010 You Can Get There From Here Acetone Anionic Ketones and Even Carbon Fatty Acids can Provide Substrates for Gluconeogenesis Nig J Physiol Sci 25 2 4 Archived from the original on 2013 09 26 Retrieved 2013 09 01 Miller DN Bazzano G 1965 Propanediol metabolism and its relation to lactic acid metabolism Ann NY Acad Sci 119 3 957 973 Bibcode 1965NYASA 119 957M doi 10 1111 j 1749 6632 1965 tb47455 x PMID 4285478 S2CID 37769342 Ruddick JA 1972 Toxicology metabolism and biochemistry of 1 2 propanediol Toxicol Appl Pharmacol 21 1 102 111 doi 10 1016 0041 008X 72 90032 4 PMID 4553872 Ivanov Vitalii Trojanowska Justyna Machado Jose Liaposhchenko Oleksandr Zajac Jozef Pavlenko Ivan Edl Milan Perakovic Dragan 2019 Advances in design simulation and manufacturing II proceedings of the 2nd International Conference on Design Simulation Manufacturing The Innovation Exchange DSMIE 2019 June 11 14 2019 Lutsk Ukraine Cham pp 430 435 ISBN 978 3 030 22365 6 OCLC 1104227601 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link Mine Safety and Health Administration MSHA Safety Hazard Information Special Hazards of Acetylene Archived 2016 01 22 at the Wayback Machine Msha gov Retrieved on 2012 11 26 History Acetylene dissolved in acetone Archived 2015 09 15 at the Wayback Machine Aga com Retrieved on 2012 11 26 Weiner Myra L Lois A Kotkoskie 1999 Excipient Toxicity and Safety Taylor amp Francis p 32 ISBN 978 0 8247 8210 8 Inactive Ingredient Search for Approved Drug Products FDA Center for Drug Evaluation and Research Wittcoff Harold Reuben B G Plotkin Jeffrey S 2004 Industrial organic chemicals Hoboken N J Wiley Interscience p 259 ISBN 0 471 44385 9 OCLC 53307689 Cleaning Glassware PDF Wesleyan University September 2009 Retrieved July 7 2016 What is an Azeotrope Solvent recycling com Retrieved on 2012 11 26 Addison Ault 1998 Studyguide for Techniques and Experiments for Organic Chemistry Sausalito CA p 310 ISBN 9780935702767 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link Lozano A Yip B Hanson R K 1992 Acetone a tracer for concentration measurements in gaseous flows by planar laser induced fluorescence Exp Fluids 13 6 369 376 Bibcode 1992ExFl 13 369L doi 10 1007 BF00223244 S2CID 121060565 a b Simpson 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 ISSN 1535 3893 PMID 20000691 Basten O Bandorski D Bismarck C Neumann K Fisseler Eckhoff A 2009 Acetonkompression Der Pathologe in German 31 3 218 224 doi 10 1007 s00292 009 1256 7 PMID 20012620 S2CID 195684316 Leung C A W Fazzi G E Melenhorst J Rennspiess D Grabsch H I November 2018 Acetone clearance of mesocolic or mesorectal fat increases lymph node yield and may improve detection of high risk Stage II colorectal cancer patients PDF Colorectal Disease 20 11 1014 1019 doi 10 1111 codi 14335 PMID 29989291 S2CID 205030844 Engbaek K Johansen KS Jensen ME February 1979 A new technique for Gram staining paraffin embedded tissue Journal of Clinical Pathology 32 2 187 90 doi 10 1136 jcp 32 2 187 PMC 1145607 PMID 86548 MacFarlane Deborah F 2010 Skin cancer management a practical approach New York Springer p 35 ISBN 978 0 387 88495 0 OCLC 663098001 a b Likhodii SS Serbanescu I Cortez MA Murphy P Snead OC 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 PMID 12891674 S2CID 3213318 American Chemistry Council Acetone Panel September 10 2003 Acetone CAS No 67 64 1 VCCEP Submission PDF pp 6 9 Retrieved 2018 04 14 Davis Gretchen Hall Mindy 2012 The makeup artist handbook techniques for film television photography and theatre Waltham MA Focal Press p 3 ISBN 978 0 240 81894 8 OCLC 776632427 Quality Finish 3D Prints with Acetone instructables com a b c Acetone MSDS hazard com 1998 04 21 Archived from the original on 2012 07 09 Retrieved 2012 11 26 a href Template Cite web html title Template Cite web cite web a CS1 maint unfit URL link Hauptmanns Ulrich 2014 Process and plant safety Berlin p 20 ISBN 978 3 642 40954 7 OCLC 888160502 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link Haynes p 16 3 Haynes p 16 5 Bingham Eula Cohrssen Barbara Patty F A 2012 Patty s toxicology Hoboken New Jersey p 736 ISBN 978 1 62198 026 1 OCLC 810064538 a href Template Cite book html title Template Cite book cite book a CS1 maint location missing publisher link Basic Information on Acetone Ccohs ca 1999 02 19 Retrieved on 2012 11 26 a b SIDS Initial Assessment Report Acetone PDF Environmental Protection Agency Archived from the original PDF on 2014 03 09 Retrieved 2014 09 11 What are the potential health effects of acetone Canadian Centre for Occupational Health and Safety Archived from the original on 2008 10 17 Retrieved 2008 10 21 Safety MSDS data for propanone Archived 2018 03 16 at the Wayback Machine sciencelab com msds Retrieved on 2018 03 19 a b Acetone 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 U S Environmental Protection Agency June 16 1995 Air Quality Revision to Definition of Volatile Organic Compounds Exclusion of Acetone PDF Federal Register 60 116 31634 31637 Jordans Frank 30 July 2015 Philae probe finds evidence that comets can be cosmic labs The Washington Post Associated Press Archived from the original on 23 December 2018 Retrieved 30 July 2015 Science on the Surface of a Comet European Space Agency 30 July 2015 Retrieved 30 July 2015 Bibring J P Taylor M G G T Alexander C Auster U Biele J Finzi A Ercoli Goesmann F Klingehoefer G Kofman W Mottola S Seidenstiker K J Spohn T Wright I 31 July 2015 Philae s First Days on the Comet Introduction to Special Issue Science 349 6247 493 Bibcode 2015Sci 349 493B doi 10 1126 science aac5116 PMID 26228139 Common sources edit Haynes William M ed 2016 CRC Handbook of Chemistry and Physics 97th ed CRC Press ISBN 9781498754293 Further reading edit nbsp Wikimedia Commons has media related to Acetone International Chemical Safety Card 0087 NIOSH Pocket Guide to Chemical Hazards Acetone Safety Data Sheet SDS Hazardous substances databank entry at the national library of medicine Archived 2018 12 04 at the Wayback Machine SIDS Initial Assessment Report for Acetone from the Organisation for Economic Co operation and Development OECD Calculation of vapor pressure liquid density dynamic liquid viscosity surface tension of acetone Retrieved from https en wikipedia org w index php title Acetone amp oldid 1220944604, wikipedia, wiki, book, books, library,

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