Acetone

Last updated
Acetone [1]
Full structural formula of acetone with dimensions Acetone-CRC-MW-ED-dimensions-2D-Vector.svg
Full structural formula of acetone with dimensions
Skeletal formula of acetone Acetone-2D-skeletal.svg
Skeletal formula of acetone
Ball-and-stick model of acetone Acetone-3D-balls.png
Ball-and-stick model of acetone
Space-filling model of acetone Acetone-3D-vdW.png
Space-filling model of acetone
Sample of Acetone.jpg
Names
IUPAC name
Acetone [2]
Preferred IUPAC name
Propan-2-one [3]
Systematic IUPAC name
2-Propanone
Other names
  • Acetonum (Latin pronunciation:  [aˈkeːtonum] )
  • Dimethyl ketone [4]
  • Dimethyl carbonyl
  • Ketone propane [5]
  • β-Ketopropane [4]
  • Propanone [6]
  • 2-Propanone [4]
  • Pyroacetic spirit (archaic) [7]
  • Spirit of Saturn (archaic) [8]
Identifiers
3D model (JSmol)
3DMet
635680
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.602 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-662-2
1466
KEGG
MeSH Acetone
PubChem CID
RTECS number
  • AL3150000
UNII
UN number 1090
  • InChI=1S/C3H6O/c1-3(2)4/h1-2H3 Yes check.svgY
    Key: CSCPPACGZOOCGX-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C3H6O/c1-3(2)4/h1-2H3
    Key: CSCPPACGZOOCGX-UHFFFAOYAF
  • CC(=O)C
Properties
C3H6O
Molar mass 58.080 g·mol−1
AppearanceColourless 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) [4]
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)
Std molar
entropy (S⦵298)
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:
GHS-pictogram-flamme.svg GHS-pictogram-exclam.svg
Danger
H225, H302, H319, H336, H373
P210, P235, P260, P305+P351+P338
NFPA 704 (fire diamond)
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) [5]
REL (Recommended)
TWA 250 ppm (590 mg/m3) [5]
IDLH (Immediate danger)
2500 ppm [5]
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Acetone is miscible with water and serves as an important organic solvent in its own right, in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate (and from that PMMA) as well as bisphenol A. [23] [24] It is a common building block in organic chemistry. Familiar household uses of acetone are as the active ingredient in nail polish remover and as 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 infants and children who suffer from refractory epilepsy. [26]

Name

Before the developments in organic chemistry nomenclature, acetone was given many different names since the 17th century. The 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. [8]

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] [8] 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

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 like how a similarly prepared product of what was then confused with the 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 propylene. 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:

Cumene-process-overview-2D-skeletal.png

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

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

Keto/enol tautomerism

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. [44]

Acetone KetoEnol.svg

Aldol condensation

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. [45]

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 by from the 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. [46]

PKA type

The conversion of acetone to a polyketal (PKA) would be analogous to the formation of paraformaldehyde from formol, 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. [47]

In 1962, Wasaburo Kawai reported the synthesis of a similar product, from liquid acetone cooled to −70 to −78 °C, using n-butyl lithium or triethylaluminium as catalysts. He claimed that the infrared absorption spectrum showed the presence of −O− linkages but no C=O groups. [48] However, conflicting results were obtained later by other investigators. [46]

Structure of possible acetone polymer Acetone-polymerisation.svg
Structure of possible acetone polymer

PMA type

The PMA type polymers of acetone would be equivalent to the product of polymerisation of propyne, except for a keto end group. [46]

Biochemistry

Biosynthesis

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. [49]

Acetone can be produced from the oxidation of ingested isopropanol, or from the spontaneous/enzymatic breakdown of acetoacetate (a ketone body) in ketotic individuals. [49]

Metabolism

Although some biochemistry textbooks and current research publications [50] indicate that acetone cannot be metabolized, there is evidence to the contrary. It 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. [51] [52] [53]

Uses

Industrial

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

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. [54]

Acetylene carrier

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). [55] [56]

Chemical intermediate

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. [57]

Laboratory

Chromatography

HPLC readout of an Excedrin tablet. Peaks from left to right are acetaminophen, aspirin, and caffeine. HPLC readout for APAP, ASA, and caffeine mixture.png
HPLC readout of an Excedrin tablet. Peaks from left to right are acetaminophen, aspirin, and caffeine.

Spectroscopy techniques are useful when the sample being tested is pure, or a very common mixture. When an unknown mixture is being analyzed it must be broken down into its individual parts. Chromatography techniques can be used to break apart mixtures into their components allowing for each part to be analyzed separately.

Thin layer chromatography (TLC) is a quick alternative to more complex chromatography methods. TLC can be used to analyze inks and dyes by extracting the individual components. [58] This can be used to investigate notes or fibers left at the scene since each company's product is slightly different and those differences can be seen with TLC. The only limiting factor with TLC analysis is the necessity for the components to be soluble in whatever solution is used to carry the components up the analysis plate. [58] This solution is called the mobile phase. [58] The forensic chemist can compare unknowns with known standards by looking at the distance each component travelled. [58] This distance, when compared to the starting point, is known as the retention factor (Rf) for each extracted component. [58] If each Rf value matches a known sample, that is an indication of the unknown's identity. [58]

High-performance liquid chromatography can be used to extract individual components from a mixture dissolved in a solution. HPLC is used for nonvolatile mixtures that would not be suitable for gas chromatography. [59] This is useful in drug analysis where the pharmaceutical is a combination drug since the components would separate, or elute, at different times allowing for the verification of each component. [60] The eluates from the HPLC column are then fed into various detectors that produce a peak on a graph relative to its concentration as it elutes off the column. The most common type of detector is an ultraviolet-visible spectrometer as the most common item of interest tested with HPLC, pharmaceuticals, have UV absorbance. [61]

Gas chromatography (GC) performs the same function as liquid chromatography, but it is used for volatile mixtures. In forensic chemistry, the most common GC instruments use mass spectrometry as their detector. [62] GC-MS can be used in investigations of arson, poisoning, and explosions to determine exactly what was used. In theory, GC-MS instruments can detect substances whose concentrations are in the femtogram (10−15) range. [63] However, the practical detection limit for GC-MS is in the picogram (10−12) range. [64] GC-MS is also capable of quantifying the substances it detects; chemists can use this information to determine the effect the substance would have on an individual. GC-MS instruments need around 1,000 times more of the substance to quantify the amount than they need simply to detect it; the limit of quantification is typically in the nanogram (10−9) range. [64]

Chemical research

In the laboratory, acetone is used as a polar, aprotic solvent in a variety of organic reactions, such as SN2 reactions. The use of acetone solvent is critical for the Jones oxidation. It does not form an azeotrope with water (see azeotrope tables). [65] It is a common solvent for rinsing laboratory glassware because of its low cost and volatility. Despite its common use as a supposed drying agent, it is not effective except by bulk displacement and dilution. Acetone can be cooled with dry ice to −78 °C without freezing; acetone/dry ice baths are commonly used to conduct reactions at low temperatures. Acetone is fluorescent under ultraviolet light, and its vapor can be used as a fluorescent tracer in fluid flow experiments. [66]

Acetone is used to precipitate proteins. [67]

Cleaning

Low-grade acetone is commonly used in academic laboratory settings as a glassware rinsing agent for removing residue and solids before a final wash. [68]

Low-temperature bath

A mixture of acetone and dry ice is a popular cooling bath that maintains a temperature of −78 °C as long as there is some dry ice left. [69]

Histology

Acetone is used in the field of pathology to find lymph nodes in fatty tissues for tumor staging (such as looking for lymph nodes in the fat surrounding the intestines). [70] This helps dissolve the fat, and hardens the nodes, making finding them easier. [71]

Acetone also used for destaining microscope slides of certain stains. [72]

Lewis base properties

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. [73] [74]

Medical

Drug solvent and excipient

Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol. [75] Acetone is also present as an excipient in some pharmaceutical drugs. [76]

Skin defatting

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, Septisol, or a combination of these agents is commonly used in this process. [77]

Anticonvulsant

Acetone has been shown to have anticonvulsant effects in animal models of epilepsy, in the absence of toxicity, when administered in millimolar concentrations. [78] 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. [78] 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. [79]

Domestic and other niche uses

Acetone is often the primary component in cleaning agents such as nail polish and superglue removers. It may attack some plastics, however. [54]

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. [80]

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 10 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. [81]

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

Safety

Chemical

Acetone is incompatible with concentrated nitric and sulfuric acid mixtures. [82] It may also explode when mixed with chloroform in the presence of a base. [83] When oxidized, for example by reacting with hydrogen peroxide, it forms acetone peroxide, which is a highly unstable, primary explosive compound. It may be formed accidentally, e.g. when waste hydrogen peroxide is poured into waste solvent containing acetone. Due to its instability, acetone peroxide's industrial use is forbidden in Europe; in the United States it is limited to minor applications, such as bleaching of flour. [84] [85]

Flammability

The most hazardous property of acetone is its extreme flammability. In small amounts acetone burns with a dull blue flame, in larger amounts the evaporation of fuel causes incomplete combustion and a bright yellow flame. At temperatures greater than acetone's flash point of −20 °C (−4 °F), air mixtures of between 2.5% and 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 point and therefore accidental ignition is rare. Even pouring or spraying acetone over red-glowing coal will not ignite it, due to the high concentration of vapour and the cooling effect of evaporation of the liquid. [86] It auto-ignites at 465 °C (869 °F). [19] Auto-ignition temperature is depends upon experimental conditions, such as exposure time, and thus can be quoted as high as 535 °C. [87] The flame temperature of pure acetone is 1980 °C. [88]

Toxicity

Acetone 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. [89] It is generally recognized to have low acute and chronic toxicity if ingested and/or inhaled. [90] Acetone is not currently regarded as a carcinogen, a mutagenic chemical nor a concern for chronic neurotoxicity effects. [86]

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 beverages, baked foods, desserts, and preserves at concentrations ranging from 5 to 8 mg/L. [90]

Acetone is however an irritant, causing mild skin irritation and moderate to severe eye irritation. At high vapor concentrations, it may depress the central nervous system like many other solvents. [91] Acute toxicity for mice by ingestion (LD50) is 3 g/kg, and by inhalation (LC50) is 44 g/m3 over 4 hours. [92]

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. [93] 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]

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, [94] the majority of the acetone released into the environment is of industrial origin. 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. [95] ) Consumption by microorganisms contributes to the dissipation of acetone in soil, animals, or waterways. [94]

The LD50 of acetone for mammals, such as rats, rabbits and sheep, varies from tens to hundreds of mg per kg of body weight, depending on the administration route (oral or intravenous) and other experimental conditions. [96] Its half-life in water is 2 to 20 days, [97] and in human blood is 18 hours. [98] Acetone may pose a significant risk of oxygen depletion in aquatic systems due to microbial consumption. [99]

Extraterrestrial occurrence

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. [100] [101] [102]

Related Research Articles

<span class="mw-page-title-main">Carboxylic acid</span> Organic compound containing a –C(=O)OH group

In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is R−COOH or R−CO2H, with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.

<span class="mw-page-title-main">Ester</span> Compound derived from an acid

In chemistry, an ester is a compound derived from an acid in which the hydrogen atom (H) of at least one acidic hydroxyl group of that acid is replaced by an organyl group. Analogues derived from oxygen replaced by other chalcogens belong to the ester category as well. According to some authors, organyl derivatives of acidic hydrogen of other acids are esters as well, but not according to the IUPAC.

<span class="mw-page-title-main">Ketone</span> Organic compounds of the form >C=O

In organic chemistry, a ketone is a functional group with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and in industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Acetophenone</span> Chemical compound

Acetophenone is the organic compound with the formula C6H5C(O)CH3. It is the simplest aromatic ketone. This colorless, viscous liquid is a precursor to useful resins and fragrances.

<span class="mw-page-title-main">Acetoacetic acid</span> Chemical compound

Acetoacetic acid is the organic compound with the formula CH3COCH2COOH. It is the simplest beta-keto acid, and like other members of this class, it is unstable. The methyl and ethyl esters, which are quite stable, are produced on a large scale industrially as precursors to dyes. Acetoacetic acid is a weak acid.

<span class="mw-page-title-main">Butanone</span> Chemical compound

Butanone, also known as methyl ethyl ketone (MEK), is an organic compound with the formula CH3C(O)CH2CH3. This colourless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

In organic chemistry, an oxime is a organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

<span class="mw-page-title-main">Dicarbonyl</span> Molecule containing two adjacent C=O groups

In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.

<span class="mw-page-title-main">Cyanohydrin</span> Functional group in organic chemistry

In organic chemistry, a cyanohydrin or hydroxynitrile is a functional group found in organic compounds in which a cyano and a hydroxy group are attached to the same carbon atom. The general formula is R2C(OH)CN, where R is H, alkyl, or aryl. Cyanohydrins are industrially important precursors to carboxylic acids and some amino acids. Cyanohydrins can be formed by the cyanohydrin reaction, which involves treating a ketone or an aldehyde with hydrogen cyanide (HCN) in the presence of excess amounts of sodium cyanide (NaCN) as a catalyst:

<span class="mw-page-title-main">Acetylacetone</span> Chemical compound

Acetylacetone is an organic compound with the chemical formula CH3COCH2COCH3. It is a colorless liquid, classified as a 1,3-diketone. It exists in equilibrium with a tautomer CH3C(O)CH=(OH)CH3. These tautomers interconvert so rapidly under most conditions that they are treated as a single compound in most applications. It is a colorless liquid that is a precursor to acetylacetonate anion, a bidentate ligand. It is also a building block for the synthesis of heterocyclic compounds.

In organic chemistry, α-keto halogenation is a special type of halogenation. The reaction may be carried out under either acidic or basic conditions in an aqueous medium with the corresponding elemental halogen. In this way, chloride, bromide, and iodide functionality can be inserted selectively in the alpha position of a ketone.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

2-Butanol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol. isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-2-butanol and (S)-(+)-2-butanol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<span class="mw-page-title-main">Cyclohexanone</span> Chemical compound

Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohexanone assume a pale yellow color. Cyclohexanone is slightly soluble in water and miscible with common organic solvents. Billions of kilograms are produced annually, mainly as a precursor to nylon.

In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl functional group by formaldehyde and a primary or secondary amine or ammonia. The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after Carl Mannich.

<span class="mw-page-title-main">Methyl isobutyl ketone</span> Chemical compound

Methyl isobutyl ketone (MIBK) is the common name for the organic compound 4-methylpentan-2-one, condensed chemical formula (CH3)2CHCH2C(O)CH3. This colourless liquid, a ketone, is used as a solvent for gums, resins, paints, varnishes, lacquers, and nitrocellulose.

<span class="mw-page-title-main">Methyl vinyl ketone</span> Chemical compound

Methyl vinyl ketone (MVK, IUPAC name: butenone) is the organic compound with the formula CH3C(O)CH=CH2. It is a reactive compound classified as an enone, in fact the simplest example thereof. It is a colorless, flammable, highly toxic liquid with a pungent odor. It is soluble in water and polar organic solvents. It is a useful intermediate in the synthesis of other compounds.

<span class="mw-page-title-main">Dimethyl carbonate</span> Chemical compound

Dimethyl carbonate (DMC) is an organic compound with the formula OC(OCH3)2. It is a colourless, flammable liquid. It is classified as a carbonate ester. This compound has found use as a methylating agent and more recently as a solvent that is exempt from the restrictions placed on most volatile organic compounds (VOCs) in the US. Dimethyl carbonate is often considered to be a green reagent.

<span class="mw-page-title-main">Haloform reaction</span> Chemical reaction involving repeated halogenation of an acetyl group (–COCH3)

In chemistry, the haloform reaction is a chemical reaction in which a haloform is produced by the exhaustive halogenation of an acetyl group, in the presence of a base. The reaction can be used to transform acetyl groups into carboxyl groups or to produce chloroform, bromoform, or iodoform. Note that fluoroform can't be prepared in this way.

Isopropyl alcohol is a colorless, flammable organic compound with a pungent alcoholic odor. As an isopropyl group linked to a hydroxyl group it is the simplest example of a secondary alcohol, where the alcohol carbon atom is attached to two other carbon atoms. It is a structural isomer of propan-1-ol and ethyl methyl ether.

References

  1. ↑ The Merck Index , 15th Ed. (2013), p. 13, Acetone Monograph 65, O'Neil: The Royal Society of Chemistry.(subscription required)
  2. ↑ ChemSpider lists 'acetone' as a valid, expert-verified name for what would systematically be called 'propan-2-one'.
  3. ↑ 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.
  4. 1 2 3 4 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)
  5. 1 2 3 4 NIOSH Pocket Guide to Chemical Hazards. "#0004". National Institute for Occupational Safety and Health (NIOSH).
  6. ↑ 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.
  7. ↑ Myers, Richard L. (2007). The 100 Most Important Chemical Compounds: A Reference Guide. Greenwood. pp.  4–6. ISBN   978-0-313-08057-9.
  8. 1 2 3 Mel Gorman, History of acetone (1600-1850), 1962
  9. 1 2 Toxicological Profile for Acetone. U.S. Environmental Protection Agency. June 2022. p. 7.
  10. 1 2 3 4 5 6 Haynes, p. 3.4
  11. ↑ Haynes, p. 5.173
  12. ↑ 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.
  13. ↑ Bordwell, Frederick G. (1988). "Equilibrium acidities in dimethyl sulfoxide solution". Accounts of Chemical Research. 21 (12): 456–463. doi:10.1021/ar00156a004.
  14. ↑ Haynes, p. 3.576
  15. ↑ Haynes, p. 6.254
  16. ↑ Haynes, p. 6.243
  17. ↑ Haynes, p. 9.60
  18. ↑ Haynes, pp. 5.3, 5.67
  19. 1 2 3 4 Haynes, p. 15.13
  20. 1 2 Haynes, p. 16.34
  21. 1 2 3 "Acetone". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  22. ↑ 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.
  23. 1 2 3 Acetone, World Petrochemicals report, January 2010
  24. 1 2 3 4 5 6 Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.
  25. ↑ "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.
  26. ↑ 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.
  27. ↑ 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.
  28. 1 2 "Acetone". 28 September 2018.
  29. ↑ Libavius, Andreas (1606). Alchymia (in Latin). Frankfurt, Germany: printed by Joannes Saurius, at the expense of Peter Kopff. p. 123.
  30. ↑ "Aceton". Chemgapedia.
  31. ↑ Dumas, J. (1832) "Sur l'esprit pyro-acétique" (On pyro-acetic spirit), Annales de Chimie et de Physique, 2nd series, 49 : 208–210.
  32. ↑ Liebig, Justus (1832) "Sur les combinaisons produites par l'action du gas oléfiant et l'esprit acétique" (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).
  33. ↑ Bussy, Antoine (1833) "De quelques Produits nouveaux obtenus par l’action des Alcalis sur les Corps gras à une haute température" (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.
  34. ↑ Williamson, A. W. (1852) "On Etherification," Journal of the Chemical Society, 4 : 229–239; (especially pp. 237–239).
  35. ↑ 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.
  36. ↑ Kekulé, Auguste (1865) "Sur la constitution des substances aromatiques," Bulletin de la Société chimique de Paris, 1 : 98–110; (especially p. 110).
  37. ↑ Kekulé, Auguste (1866) "Untersuchungen über aromatischen Verbindungen" (Investigations into aromatic compounds), Annalen der Chemie und Pharmacie, 137 : 129–196; (especially pp. 143–144).
  38. ↑ Loschmidt, J. (1861) Chemische Studien Vienna, Austria-Hungary: Carl Gerold's Sohn.
  39. ↑ Chaim Weizmann. chemistryexplained.com
  40. 1 2 Greiner, Camara; Funada, C (June 2010). "CEH Marketing Research Report: ACETONE". Chemical Economics Handbook. SRI consulting. Retrieved 2 September 2016.(subscription required)
  41. ↑ "Acetone Uses and Market Data". ICIS.com. October 2010. Archived from the original on 2009-05-15. Retrieved 2011-03-21.
  42. ↑ Acetone (US Gulf) Price Report – Chemical pricing information Archived 2013-05-16 at the Wayback Machine . ICIS Pricing. Retrieved on 2012-11-26.
  43. ↑ 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.
  44. ↑ 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 .
  45. ↑ Sowa, John R. (2005). Catalysis of organic reactions. Boca Raton: Taylor & Francis. p. 363. ISBN   978-0-8247-2729-1. OCLC   67767141.
  46. 1 2 3 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.
  47. ↑ Kargin, V. A.; Kabanov, V. A.; Zubov, V. P.; Papisov, I. M. (1960). "Polymerisation of acetone". Doklady Akademii Nauk SSSR. 134 (5): 1098–1099.
  48. ↑ Kawai, Wasaburo (1962). "Polymerization of Acetone". Bulletin of the Chemical Society of Japan. 35 (3): 516A. doi: 10.1246/bcsj.35.516a .
  49. 1 2 Karch, Steven B. (1998). Drug abuse handbook. Boca Raton, Fla.: CRC Press. p. 369. ISBN   978-1-4200-4829-2. OCLC   61503700.
  50. ↑ Vujasinovic, M; Kocar, M; Kramer, K; Bunc, M; Brvar, M (2007). "Poisoning with 1-propanol and 2-propanol". Human & Experimental Toxicology. 26 (12): 975–8. doi:10.1177/0960327107087794. PMID   18375643. S2CID   11723110.
  51. ↑ 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.
  52. ↑ 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.
  53. ↑ 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.
  54. 1 2 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.
  55. ↑ 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.
  56. ↑ History – Acetylene dissolved in acetone Archived 2015-09-15 at the Wayback Machine . Aga.com. Retrieved on 2012-11-26
  57. ↑ 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.
  58. 1 2 3 4 5 6 Carlysle, Felicity (2011-07-26). "TLC the Forensic Way". theGIST. Glasgow Insight Into Science & Technology. Archived from the original on July 30, 2016. Retrieved October 10, 2015.
  59. ↑ Picó, Yolanda, ed. (2012). Chemical Analysis of Food: Techniques and Applications. Elsevier. p. 501. ISBN   9780123848628 – via Google Books.
  60. ↑ Nikolin, B; Imamović, B; Medanhodzić-Vuk, S; Sober, M (May 2004). "High Performance Liquid Chromatography in Pharmaceutical Analyses". Bosnian Journal of Basic Medical Sciences. 4 (2): 5–9. doi: 10.17305/bjbms.2004.3405 . PMC   7250120 . PMID   15629016.
  61. ↑ Dong, Michael W. (2016). Modern HPLC for Practicing Scientists. John Wiley & Sons. ISBN   9780471727897 – via Google Books.
  62. ↑ "A Simplified Guide to Forensic Drug Chemistry" (PDF). National Forensic Science Technology Center. Archived from the original (PDF) on March 21, 2016. Retrieved September 24, 2015.
  63. ↑ Fialkov, Alexander; Steiner, Urs; Lehotay, Steven; Amirav, Aviv (January 15, 2007). "Sensitivity and Noise in GC-MS: Achieving Low Limits of Detection for Difficult Analytes". International Journal of Mass Spectrometry. 260 (1): 31–48. Bibcode:2007IJMSp.260...31F. doi:10.1016/j.ijms.2006.07.002.
  64. 1 2 Smith, Michael L.; Vorce, Shawn P.; Holler, Justin M.; Shimomura, Eric; Magluilo, Joe; Jacobs, Aaron J.; Huestis, Marilyn A. (June 2007). "Modern Instrumental Methods in Forensic Toxicology". Journal of Analytical Toxicology. 31 (5): 237–253. doi:10.1093/jat/31.5.237. PMC   2745311 . PMID   17579968.
  65. ↑ What is an Azeotrope?. Solvent—recycling.com. Retrieved on 2012-11-26.
  66. ↑ 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.
  67. ↑ Simpson, Deborah M.; Beynon, Robert J. (2009). "Acetone precipitation of proteins and the modification of peptides". Journal of Proteome Research. 9 (1): 444–450. doi:10.1021/pr900806x. PMID   20000691.
  68. ↑ "Cleaning Glassware" (PDF). Wesleyan University. September 2009. Retrieved July 7, 2016.
  69. ↑ Addison, Ault (1998). Studyguide for Techniques and Experiments for Organic Chemistry. Sausalito, CA. p. 310. ISBN   9780935702767.
  70. ↑ 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.
  71. ↑ 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.
  72. ↑ 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.
  73. ↑ 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.
  74. ↑ 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. doi: 10.1107/S0108270106028903 . PMID   16954630.
  75. ↑ Weiner, Myra L.; Lois A. Kotkoskie (1999). Excipient Toxicity and Safety . p. 32. ISBN   978-0-8247-8210-8.
  76. ↑ Inactive Ingredient Search for Approved Drug Products, FDA/Center for Drug Evaluation and Research
  77. ↑ MacFarlane, Deborah F. (2010). Skin cancer management : a practical approach. New York: Springer. p. 35. ISBN   978-0-387-88495-0. OCLC   663098001.
  78. 1 2 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.
  79. ↑ American Chemistry Council Acetone Panel (September 10, 2003). "Acetone (CAS No. 67-64-1) VCCEP Submission" (PDF). pp. 6, 9. Retrieved 2018-04-14.
  80. ↑ 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.
  81. ↑ "Quality Finish 3D Prints with Acetone". instructables.com
  82. ↑ Haynes, p. 16.3
  83. ↑ Haynes, p. 16.5
  84. ↑ Bingham, Eula; Cohrssen, Barbara; Patty, F. A. (2012). Patty's toxicology. Hoboken, New Jersey. p. 736. ISBN   978-1-62198-026-1. OCLC   810064538.
  85. ↑ Cauvain, Stanley P.; Young, Linda S. (2009). The ICC handbook of cereals, flour, dough & product testing : methods and applications. Lancaster, PA: DEStech Pub. p. 115. ISBN   978-1-932078-99-2. OCLC   318875533.
  86. 1 2 Acetone MSDS. Hazard.com (1998-04-21). Retrieved on 2012-11-26.
  87. ↑ Hauptmanns, Ulrich (2014). Process and plant safety. Berlin. p. 20. ISBN   978-3-642-40954-7. OCLC   888160502.
  88. ↑ Haynes, p. 15.49
  89. ↑ Basic Information on Acetone. Ccohs.ca (1999-02-19). Retrieved on 2012-11-26.
  90. 1 2 "SIDS Initial Assessment Report: Acetone" (PDF). Environmental Protection Agency. Archived from the original (PDF) on 2014-03-09. Retrieved 2014-09-11.
  91. ↑ "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.
  92. ↑ Safety (MSDS) data for propanone Archived 2018-03-16 at the Wayback Machine . sciencelab.com/msds. Retrieved on 2018-03-19
  93. ↑ 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.
  94. 1 2 Acetone, Agency for Toxic Substances and Disease Registry ToxFAQs, 1995
  95. ↑ 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.
  96. ↑ Negherbon, W.O. (1959) Handbook of Toxicology: Insecticides. Saunders. p. 162
  97. ↑ Vincoli, Jeffrey W. (1997). Risk management for hazardous chemicals. Boca Raton, Fla.: CRC Lewis Publishers. p. 5. ISBN   1-56670-200-3. OCLC   35521567.
  98. ↑ National Research Council. Subcommittee on Spacecraft Exposure Guidelines (2004). Spacecraft water exposure guidelines for selected contaminants. Volume 2. Washington, D.C.: National Academy of Sciences. p. 14. ISBN   0-309-18007-4. OCLC   1317408038.
  99. ↑ "Safety Data Sheet Acetone" (PDF). J.M. Loveridge. Archived from the original (PDF) on 2009-03-20. Retrieved 2012-11-26.
  100. ↑ 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.
  101. ↑ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
  102. ↑ 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.

Cited sources

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.