Listing description
ACS
reagent,>99.5%
CAS number
67-64-1
Linear
formular CH3COCH3
Molecular
weight 58.08
Beilstein
registry number 635680
EC NUMBER 200-662-2
MDL number
MFCD00008765
pubChem
substance ID 329751579
eCl@ss
39021201
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Related Categories
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More...
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grade
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ACS reagent
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vapor density
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2 (vs air)
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vapor pressure
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184 mmHg ( 20 °C)
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InChI Key
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CSCPPACGZOOCGX-UHFFFAOYSA-N
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assay
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≥99.5%
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form
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liquid (clear)
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shelf life
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Recommended retest period - 2
years
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Acetone (systematically
named propanone) is the organic compound with the formula (CH3)2CO.[12] It is a
colorless, volatile, flammable liquid, and is the simplest ketone.
Acetone is miscible with water and serves as
an important solvent in its own
right, typically for cleaning purposes in the laboratory. About 6.7
million tonnes were produced worldwide in 2010,
mainly for use as a solvent and production of methyl methacrylate and bisphenol A.[13][14] 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.
Detailed description
Acetone
is produced and disposed of in the human body through normal metabolic
processes. It is normally present in blood and urine. People with diabetes produce
it in larger amounts. Reproductive toxicity tests show that it has low
potential to cause reproductive problems. Pregnant women, nursing mothers and
children have higher levels of acetone.[15] Ketogenic diets that increase acetone in the body
are used to counter epileptic attacks
in infants and children who suffer from recalcitrant refractory epilepsy.
Uses[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.[13]
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. It is
also useful for high reliability soldering applications
to remove rosin flux after
soldering is complete; this helps to prevent the rusty bolt effect.
Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol. Acetone is
also present as an excipient in
some pharmaceutical drugs.
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 liter of acetone
can dissolve around 250 liters of acetylene at a pressure of 10 bar.
Chemical intermediate
Acetone is used to synthesize methyl methacrylate. It begins with the initial conversion of acetone to acetone cyanohydrin:
(CH3)2CO
+ HCN → (CH3)2C(OH)CN
In a subsequent step, the nitrile is hydrolyzed to the
unsaturated amide, which is esterified:
(CH3)2C(OH)CN
+ CH3OH → CH2=(CH3)CCO2CH3 +
NH3
The third major use of acetone (about 20%)[13] 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:
(CH3)2CO
+ 2 C6H5OH → (CH3)2C(C6H4OH)2 +
H2O
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.[14]
2
(CH3)2CO → (CH3)2C(OH)CH2C(O)CH3
Laboratory
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 (data)).[38] 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.[39]
Medical and cosmetic uses
Acetone is used in a variety of general medical and
cosmetic applications and is also listed as a component in food additives and food
packaging and also in nail polish remover. Dermatologists use acetone with
alcohol for acne treatments to peel dry skin.
Acetone is commonly used in chemical peeling. Common agents used
today for chemical peels are salicylic acid, glycolic 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.
Domestic and other niche uses
Acetone is often the primary component in cleaning
agents such as nail polish remover.
Acetone is a component of superglue remover and
easily removes residues from glass and porcelain. Make-up artists use acetone to
remove skin adhesive from the netting of wigs and moustaches by immersing the
item in an acetone bath, then removing the softened glue residue with a stiff
brush.
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.
Low-grade acetone is also commonly used in academic
laboratory settings as a glassware rinsing agent for removing residue and
solids before a final wash.
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