Everything about Acetone totally explained
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Acetone (also known as
propanone,
dimethyl ketone,
2-propanone,
propan-2-one and
β-ketopropane) is a colorless, mobile, flammable liquid. It is the simplest example of the
ketones. Acetone is
miscible with
water,
ethanol,
ether, etc., and itself serves as an important
solvent. The most familiar household use of acetone is as the active ingredient in
nail polish remover and
paint thinner. Acetone is also used to make
plastic, fibers, drugs, and other chemicals. In addition to being manufactured as a chemical, acetone is also found naturally in the environment, including in small amounts in the human body.
Production
Acetone is produced primarily in the
cumene process. Previously, acetone was produced by the
dry distillation of
acetates, for example
calcium acetate. During
World War I a new process of producing acetone through
bacterial fermentation was developed by
Chaim Weizmann, later the first president of
Israel, in order to help the British war effort. This
Acetone Butanol Ethanol process was abandoned due to the small yield of Acetone
Butanol compared to the organic waste.
Biosynthesis
Small amounts of acetone are produced in the body by the
decarboxylation of
ketone bodies.
Uses
Cleaning fluid
Acetone is often the primary (or only) component in
nail polish remover.
Ethyl acetate, another organic solvent, is sometimes used as well. Acetone is also used as a
superglue remover. It can be used for thinning and cleaning fiberglass resins and epoxies. It is a strong solvent for most plastics and synthetic fibres.
It is ideal for thinning fiberglass resin, cleaning fiberglass tools and dissolving two-part
epoxies and
superglue before hardening. A heavy-duty degreaser, it's useful in the preparation of metal prior to painting; it also thins polyester resins, vinyl and adhesives. It easily removes residues from glass and porcelain. In biological research contexts, buffers that contain acetone (such as citrate-buffered formalin) use the acetone to
lyse cells for further experimentation.
Additionally, acetone is extremely effective when used as a cleaning agent when dealing with permanent markers.
Solvent
Acetone can also dissolve many plastics, including those used in
Nalgene bottles made of polystyrene, polycarbonate and some types of polypropylene.
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 also critical for the successful
Jones oxidation. Technical grade acetone is inexpensive. Because of acetone's medium polarity, it dissolves a wide range of compounds. Thus, it's commonly loaded into squeeze bottles and used as a general solvent in rinsing
laboratory glassware.
Acetone is also used extensively for the safe transporting and storing of
acetylene. Vessels containing a porous material are first filled with acetone followed by acetylene, which dissolves into the acetone. One liter of acetone can dissolve around 250 liters of acetylene.
Feedstock
An important industrial use for acetone involves its reaction with
phenol for the manufacture of
bisphenol A. Bisphenol A is an important component of many polymers such as
polycarbonates,
polyurethanes and
epoxy resins. Acetone has also been used in the manufacture of
cordite.
Automotive fuel additive
Some automotive enthusiasts add acetone at around 1 part in 500 to their fuel, following claims of dramatic improvement in fuel economy and engine life. This practice is controversial as the body of systematic testing shows that acetone has no measurable effect or may in fact reduce engine life by adversely affecting fuel system parts. Debates on this subject and the perrenial claims of a "Big Oil" cover-up intensified when the practice was addressed on the popular American TV show
MythBusters in 2006, and shown to have negative effect in the televised fuel economy test.. The jury is still out though, the only negatives to using acetone would be the result of exceeding the recommended blending calculation (one ounce of acetone to five gallons of gasoline). Even common paint thinner (which contains acetone, and other chemicals, some of which have been used to boost octane and fuel Formula One race cars, such as toluene and xylene) has been used as a gasoline and diesel fuel additive, point being that the chemical surface tension of the gasoline will be reduced to allow a more efficient combustion process to occur, thus resulting in better economy and performance. Conversely, alcohol based octane boosters, such as ethanol and methanol, actually increase the chemical surface tension of common gasoline, and this is precisely why less economy, less miles per gallon, occurs when using alcohol as an additive in gasoline.
Other uses
Acetone is also used as a
drying agent, due to the readiness with which it mixes with water, and its volatility.
It can be used as an artistic agent; when rubbed on the back of a laser print or photocopy placed face-down on another surface and burnished firmly, the toner of the image is allowed to transfer to the destination surface.
Safety
Acetone peroxide
When oxidized, acetone forms acetone peroxide as a by-product, which is a highly unstable compound. It may be formed accidentally, for example when waste
hydrogen peroxide is poured into a carboy containing waste acetone solvent. Acetone peroxide is more than ten times as friction and shock sensitive as
nitroglycerin. Due to its instability, it's rarely used, despite its easy chemical synthesis.
Toxicology
Acetone is an irritant and inhalation may lead to
hepatotoxic effects (causing liver damage). The vapors should be avoided. In no circumstance should it be consumed directly or indirectly. Always use goggles when handling acetone; it can cause permanent eye damage (
corneal clouding).
Small amounts of acetone are metabolically produced in the body, mainly from fat. In humans, fasting significantly increases its endogenous production (see
ketosis). Acetone can be elevated in
diabetes. Contamination of water, food (for example milk), or the air (acetone is volatile) can lead to chronic exposure to acetone. A number of acute poisoning cases have been described. Relatively speaking, acetone isn't a very toxic compound; it can, however, damage the
mucosa of the
mouth and can irritate and damage skin. Accidental intake of large amounts of acetone may lead to unconsciousness and death.
The effects of long-term exposure to acetone are known mostly from animal studies.
Kidney,
liver, and
nerve damage, increased
birth defects, and lowered reproduction ability of males (only) occurred in animals exposed long-term. It isn't known if these same effects would be exhibited in humans. Pregnant women should avoid contact with acetone and acetone fumes in order to avoid the possibility of birth defects, including brain damage.
Interestingly, acetone has been shown to have
anticonvulsant effects in animal models of
epilepsy, in the absence of toxicity, when administered in millimolar concentrations. 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.
[Further Information]
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