Acetone
In 1839, the name acetone began to be used and the term was composed of daughter of and acetum. Acetum means acetic acid in Latin. The prefix refers to acetone's relation to vinegar rather than its chemical structure. 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. Prior to the name acetone being coined by French chemists, it was named mesit by Carl Reichenbach. Mesit comes from the Greek word meaning mediator. Names derived from mesit include mesitylene and mesityl oxide which were first synthesised from acetone. 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.
Acetone was first produced by Andreas Libavius in 1606 by distillation of lead(II) acetate. In 1832, French chemist Jean-Baptiste Dumas and German chemist Justus von Liebig determined the empirical formula for acetone. 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. By 1852, English chemist Alexander William Williamson realized that acetone was methyl acetyl. The following year, the French chemist Charles Frédéric Gerhardt concurred. In 1865, the German chemist August Kekulé published the modern structural formula for acetone. Johann Josef Loschmidt had presented the structure of acetone in 1861 but his privately published booklet received little attention. During World War I, Chaim Weizmann developed the process for industrial production of acetone. This process became known as the Weizmann Process.
Approximately 83% of acetone is produced via the cumene process. As a result, acetone production is tied to phenol production. In the cumene process, benzene is alkylated with propylene to produce cumene. Cumene is oxidized by air to produce acetone and phenol. Other processes involve the direct oxidation of propylene or the hydration of propylene to give 2-propanol. Previously, acetone was produced by the dry distillation of acetates. After that time, during World War I, acetone was produced using acetone-butanol-ethanol fermentation with Clostridium acetobutylicum bacteria. This method was developed by Chaim Weizmann to help the British war effort. The acetone-butanol-ethanol fermentation was eventually abandoned when newer methods with better yields were found. In 2010, the worldwide production capacity for acetone was estimated at 6.7 million tonnes per year. With 1.56 million tonnes per year, the United States had the highest production capacity.
About a third of the world's acetone is used as a solvent. A quarter is consumed as acetone cyanohydrin, a precursor to methyl methacrylate. Acetone is used to synthesize methyl methacrylate which begins with the initial conversion of acetone to acetone cyanohydrin via reaction with hydrogen cyanide. The third major use of acetone is about 20% synthesizing bisphenol A. Bisphenol A is a component of many polymers such as polycarbonates and polyurethanes. Many millions of kilograms of acetone are consumed in the production of solvents like methyl isobutyl alcohol. Acetone is a good solvent for many plastics and some synthetic fibers. It is used for thinning polyester resin and cleaning tools used with it. Make-up artists use acetone to remove skin adhesive from the netting of wigs and mustaches by immersing the item in an acetone bath. Acetone is a main ingredient in many nail polish removers because it breaks down nail polish.
Humans exhale several milligrams of acetone per day. It arises from decarboxylation of acetoacetate. 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 ketosis, acetone is formed in body tissue. Certain health conditions such as alcoholism and diabetes can produce ketoacidosis. Ketoacidosis leads to a sharp and potentially fatal increase in the acidity of the blood. Acetone has been shown to have anticonvulsant effects in animal models of epilepsy. It works when administered in millimolar concentrations without toxicity. The high-fat low-carbohydrate ketogenic diet used clinically to control drug-resistant epilepsy in children works by elevating acetone in the brain. Children have higher acetone production than most adults because they have higher energy requirements.
Acetone has a relatively long lifetime in the atmosphere of about 2 weeks. Because of its long lifetime, it can be transported by atmospheric winds to the upper troposphere and lower stratosphere. There it can influence hydrogen radical production and ozone levels. These two peroxy radicals can then undergo a series of reactions to produce hydrogen oxide radicals. They can therefore have a significant impact on atmospheric chemistry including concentration of ozone in the upper troposphere. Photolysis is just one possible process that removes acetone from the atmosphere. Acetone can also be removed by ocean processes and by deposition to dry land surfaces. The contributions of each sink to the removal of acetone from the atmosphere is still not fully understood. On the 30th of July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67P surface measurements revealed sixteen organic compounds. Four of which were seen for the first time on a comet including acetone.
Acetone's most hazardous property is its extreme flammability. In small amounts, acetone burns with a dull blue flame. In larger amounts, fuel evaporation causes incomplete combustion and a bright yellow flame. When above acetone's flash point, air mixtures of 2.5 to 2.8 percent acetone may explode or cause a flash fire. Vapors can flow along surfaces to distant ignition sources and flash back. Static discharge may ignite acetone vapors though accidental ignition is rare. Acetone's auto-ignition temperature is relatively high at 465 degrees Celsius. Even pouring or spraying acetone over red-glowing coal will not ignite it due to the cooling effect of evaporation. Acetone should be stored away from strong oxidizers such as concentrated nitric and sulfuric acid mixtures. It may explode when mixed with chloroform in the presence of a base. Acetone occurs naturally as part of certain metabolic processes in the human body and has been studied extensively. There is no strong evidence of chronic health effects if basic precautions are followed.
Common questions
When was the name acetone first used and what is its etymology?
The name acetone began to be used in 1839. The term combines the Latin word for vinegar, acetum, with the suffix -one to indicate it is a ketone.
Who discovered acetone and when did they produce it?
Andreas Libavius produced acetone in 1606 by distilling lead(II) acetate. Carl Reichenbach previously named the substance mesit before chemists standardized the modern name.
How much acetone was produced worldwide in 2010 and which country led production?
Worldwide production capacity reached an estimated 6.7 million tonnes per year in 2010. The United States held the highest national production capacity at 1.56 million tonnes per year.
What percentage of global acetone usage goes toward solvent applications?
About one third of the world's acetone functions as a solvent. It serves as a main ingredient in nail polish removers and cleans tools used with polyester resin.
When were organic compounds including acetone detected on comet 67P?
Scientists reported findings on the 30th of July 2015 during the first touchdown of the Philae lander. Measurements revealed sixteen organic compounds including acetone for the first time on a comet surface.