ACETONE

DESCRIPTION:

Acetone (2-propanone or dimethyl ketone) is an organic compound with the formula (CH3)2CO.
Acetone is the simplest and smallest ketone (>C=O). 
Acetone is a colorless, highly volatile, and flammable liquid with a characteristic pungent odour, very reminiscent of the smell of pear drops.

CAS Number    :67-64-1 
EC Number    : 200-662-2
IUPAC name: Acetone[7]
Preferred IUPAC name: Propan-2-one[8]
Systematic IUPAC name: 2-Propanone

SYNONYMS OF ACETONE:
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]

Acetone is a toxic and flammable liquid that resembles water. 
Acetone was previously extracted from pyroligneous wood after carbonization, but is now derived from acetic acid.
This solvent is very frequently used for its dissolving properties. 

Acetone can be used to clean many objects and surfaces, including nails covered in varnish.
Acetone is therefore a kind of miracle product for painters, since it strips paint and glue, but also for grandmothers who tended to use it for household maintenance. 

Acetone is indeed effective in removing stains from rubber, glue, varnish, wax, oil, whiteout, chewing gum, grease, cement, ink, shoe polish, paint, dye, resin, silicone and modeling clay, among others.
While effective, acetone should be used with caution as it is toxic and irritating. 
Additionally, it has a strong odor that is often difficult to get rid of.

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] 

Acetone is a common building block in organic chemistry. 
Acetone serves as a solvent in household products such as nail polish remover and paint thinner. 
Acetone 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. 
Acetone 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:
From the 17th century, and before modern developments in organic chemistry nomenclature, acetone was given many different names.
They included "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 name "acetone" being coined by the French chemist 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 which have a 2-carbon chain, acetone has a 3-carbon chain. 
That has caused confusion because 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 OF ACETONE
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 OF ACETONE:
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 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
Previously, acetone was produced by the dry distillation of acetates, for example calcium acetate in ketonic decarboxylation.
Ca(CH3COO)2⟶CaO(s)+CO2(g)+(CH3)2CO↓
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 OF ACETONE:
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:
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:
Humans exhale several milligrams of acetone per day. 
Acetone 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 of Acetone
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 OF ACETONE

Acetone has several uses. 
How to remove a stain from fabric
Acetone is very effective on some products that stain and are difficult to remove, such as glue, grease, varnish, oils and rubber.

Be careful though, because this is a powerful product that may discolor delicate fabrics. 
Test it on an inconspicuous surface to check that it does not remove any color from the surface. 
If the way is clear, apply it to the stain by dabbing with a soaked cloth until it disappears. 

Rinse the fabric immediately to immediately stop the action of the acetone.
How to remove chewing gum from the sole of a shoe
After scraping the surface of the chewing gum to remove as much as possible, rub off the remainder with a sponge soaked in acetone. 
Then rinse with clean water.

How to bleach jeans
If you want to change the style of your jeans by bleaching them, lay them flat on a towel or sheet. 
Put on gloves and soak a clean cloth in acetone. 
Roll it into a sausage shape and rub it on the jeans to remove the color. 

Repeat the process several times, changing cloths to achieve the desired shade. 
Rinse and let dry before washing the jeans in the washing machine.

Cleaning a dirty window:
If your windows are dirty with limescale, paint or marked by a sticker or label, put on gloves and rub the glass surfaces with a cloth soaked in acetone. 

Finish by rinsing with a clean cloth dampened with water, then dry with a clean microfibre cloth.

Removing sap from vehicle bodies:
To remove sap drops from a windshield or car body, place a few drops of acetone on a microfiber cloth and rub the stain until it disappears. 
Do not leave it on for too long and be sure to rinse quickly.

Cleaning an iron soleplate:
When the soleplate of the iron is dirty and sticky, clean it with a clean cloth soaked in acetone. 
Then clean with a cloth with clear water and let it dry.

Cleaning a glass ceramic hob:
If your ceramic hob is dirty, wait until it has cooled down completely to wipe the surface with a sponge soaked in acetone. 
Then rinse with a sponge soaked in water, then dry with a clean, dry microfibre cloth.

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. 
Acetone is used for thinning polyester resin, cleaning tools used with it, and dissolving two-part epoxies and superglue before they harden. 
Acetone 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
Acetone is used to synthesize methyl methacrylate. 
It begins with the initial conversion of acetone to acetone cyanohydrin via reaction with hydrogen cyanide (HCN):
(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=C(CH3)CO2CH3+NH3

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:
(CH3)2CO+2C6H5OH⟶(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.[24]
2(CH3)2CO⟶(CH3)2C(OH)CH2C(O)CH3
Condensation with acetylene gives 2-methylbut-3-yn-2-ol, precursor to synthetic terpenes and terpenoids.[62]

Laboratory:
Chemistry
A variety of organic reactions employ acetone as a polar, aprotic solvent. 
Acetone 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. 
Acetone forms no azeotropes with water (see azeotrope tables).[64]
Acetone freezes well below −78 °C. 
An acetone/dry ice mixture cools many low-temperature reactions.[65]

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

Biology
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:
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
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 a main ingredient in many nail polish removers because it breaks down nail polish.[75] 

It is used for all types of nail polish removal, like gel nail polish, dip powder and acrylic nails.[76]
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.[77]
Acetone efficiently removes felt-tipped pen marks from glass and metals.

CHEMICAL AND PHYSICAL PROPERTIES OF ACETONE
Chemical formula    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]
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 (χ)    −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 molar
entropy (S⦵298)    199.8 J/(mol•K)
Std enthalpy of
formation (ΔfH⦵298)    −248.4 kJ/mol
Std enthalpy of
combustion (ΔcH⦵298)    −1.79 MJ/mol

SAFETY INFORMATION ABOUT ACETONE
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product.