Acetone

(CH 3 ) 2 COacetonylCH 3 COCH 3 methylketonePolish removerpropanone
Acetone, or propanone, is the organic compound with the formula (CH 3 ) 2 CO.wikipedia
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Ketone

ketonesketoketo group
Acetone, or propanone, is the organic compound with the formula (CH 3 ) 2 CO. It is a colorless, volatile, flammable liquid and is the simplest and smallest ketone.
Examples include many sugars (ketoses) and the industrial solvent acetone, which is the smallest ketone.

Solvent

solventsorganic solventorganic solvents
Acetone is miscible with water and serves as an important solvent in its own right, typically for cleaning purposes in laboratories.
Common uses for organic solvents are in dry cleaning (e.g. tetrachloroethylene), as paint thinners (e.g. toluene, turpentine), as nail polish removers and glue solvents (acetone, methyl acetate, ethyl acetate), in spot removers (e.g. hexane, petrol ether), in detergents (citrus terpenes) and in perfumes (ethanol).

Ketone bodies

ketone bodyketonesnegatively charged ketone
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 recalcitrant refractory epilepsy.
Ketone bodies are the water-soluble molecules (acetoacetate, beta-hydroxybutyrate, and the spontaneous breakdown product of acetoacetate, acetone) containing the ketone group that are produced by the liver from fatty acids during periods of low food intake (fasting), carbohydrate restrictive diets, starvation, prolonged intense exercise, alcoholism or in untreated (or inadequately treated) type 1 diabetes mellitus.

Methyl methacrylate

methacrylatemethyl (metha)acrylatemethyl methacrylate styrene
About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate and bisphenol A. 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.

Diabetes

diabetes mellitusdiabeticdiabetics
People with diabetes produce it in larger amounts.
People (usually with type 1 diabetes) may also experience episodes of diabetic ketoacidosis (DKA), a metabolic disturbance characterized by nausea, vomiting and abdominal pain, the smell of acetone on the breath, deep breathing known as Kussmaul breathing, and in severe cases a decreased level of consciousness.

Chaim Weizmann

WeizmannDr. Chaim WeizmannChaim Weizman
During World War I, Chaim Weizmann developed the process for industrial production of acetone (Weizmann Process). 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, in the preparation of Cordite.
He developed the acetone–butanol–ethanol fermentation process, which produces acetone, n-Butanol and ethanol through bacterial fermentation.

Acetoacetate decarboxylase

enzymatic
Acetone can be produced from the oxidation of ingested isopropanol, or from the spontaneous/enzymatic breakdown of acetoacetate (a ketone body) in ketotic individuals.
Acetoacetate decarboxylase plays a key role in solvent production by catalyzing the decarboxylation of acetoacetate, yielding acetone and carbon dioxide.

Ketosis

ketonemiahyperketonaemiahyperketosis
Certain dietary patterns, including prolonged fasting and high-fat low-carbohydrate dieting, can produce ketosis, in which acetone is formed in body tissue.
When the liver rapidly metabolizes fatty acids into acetyl-CoA, some acetyl-CoA molecules can then be converted into ketone bodies: acetoacetate, beta-hydroxybutyrate, and acetone.

Propylene glycol

1,2-propanediol1,2-propylene glycolMonopropylene Glycol
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.
It is miscible with a broad range of solvents, including water, acetone, and chloroform.

Volatile organic compound

volatile organic compoundsVOCsVOC
It has VOC exempt status in the USA.
Typical solvents are aliphatic hydrocarbons, ethyl acetate, glycol ethers, and acetone.

Paint thinner

thinnerthinnerspaint thinning
Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint thinner.

Ketogenic diet

ketoketogenicKetogenic Diets
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 recalcitrant refractory epilepsy.
He reported that three water-soluble compounds, β-hydroxybutyrate, acetoacetate, and acetone (known collectively as ketone bodies), were produced by the liver in otherwise healthy people when they were starved or if they consumed a very low-carbohydrate, high-fat diet.

CYP2E1

2E1cytochrome p-450 cyp2e1cytochrome P-4502E1
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.
In the conversion sequence of acetyl-CoA to glucose, CYP2E1 transforms acetone via hydroxyacetone (acetol) into propylene glycol and methylglyoxal, the precursors of pyruvate, acetate and lactate.

Nail polish

nail polish removernail varnishfingernail polish
Familiar household uses of acetone are as the active ingredient in nail polish remover and as paint thinner.
It is usually removed by soaking the nails in pure acetone (the solvent used in most nail polish removers) for five to fifteen minutes, depending on the formula.

Cumene process

Hock rearrangementHock processair-oxidation of cumene
Approximately 83% of acetone is produced via the cumene process; as a result, acetone production is tied to phenol production.
The cumene process (cumene-phenol process, Hock process) is an industrial process for synthesizing phenol and acetone from benzene and propylene.

Propionaldehyde

propanal
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.
It is a saturated 3-carbon aldehyde and is a structural isomer of acetone.

Acetone–butanol–ethanol fermentation

ABE fermentationA.B.E. processAcetone-butanol-ethanol fermentation
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, in the preparation of Cordite.
Acetone–butanol–ethanol (ABE) fermentation is a process that uses bacterial fermentation to produce acetone, n-Butanol, and ethanol from carbohydrates such as starch and glucose.

Acetoacetic acid

acetoacetate3-oxobutanoic acidacetoacetyl
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 recalcitrant refractory epilepsy. Acetone can be produced from the oxidation of ingested isopropanol, or from the spontaneous/enzymatic breakdown of acetoacetate (a ketone body) in ketotic individuals.
It decomposes at a moderate rate to acetone and carbon dioxide:

Phenol

carbolic acidphenoxidephenolate
In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:
In support of the second explanation, the pK a of the enol of acetone in water is 10.9, making it only slightly less acidic than phenol (pK a 10.0).

Clostridium acetobutylicum

C. acetobutylicumABE fermentationClostridium acetobutylicum'' N1-4081
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, in the preparation of Cordite.
A senior lecturer at the University of Manchester, England, he used them in 1916 as a bio-chemical tool to produce at the same time, jointly, acetone, ethanol, and butanol from starch.

Propene

propyleneC 3 H 6 propane dehydrogenation
Acetone is produced directly or indirectly from propylene.
Propene and benzene are converted to acetone and phenol via the cumene process.

Bisphenol A

BPAbisphenol-ABisphenol A (BPA)
About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate and bisphenol A.
This compound is synthesized by the condensation of acetone (hence the suffix A in the name) with two equivalents of phenol.

Cumene

IsopropylbenzeneCH(CH 3 ) 2
In the cumene process, benzene is alkylated with propylene to produce cumene, which is oxidized by air to produce phenol and acetone:
Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone.

Acetone cyanohydrin

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.
In the laboratory, this compound may be prepared by treating sodium cyanide with acetone, followed by acidification:

Denatured alcohol

methylated spiritmethylated spiritsdenatured
Acetone is used as a solvent by the pharmaceutical industry and as a denaturant in denatured alcohol.
Other typical additives include isopropyl alcohol, acetone, methyl ethyl ketone and methyl isobutyl ketone.