Acetone
Acetone is the simplest and smallest ketone, a colorless liquid you can smell long before you see it. Pour some out and it vanishes from your fingers in seconds, leaving a sharp, pungent trace in the air. Each of us makes it without trying. Small quantities sit naturally in human blood and urine, and we breathe out several milligrams of it every day. Yet the same molecule that drifts off your breath was once distilled from lead, carried a war effort, and turned up sixteen times over on the frozen surface of a comet. It is miscible with water, flammable enough to flash from a distant spark, and produced at a scale of millions of tonnes a year. So how did a substance this ordinary come to be called the spirit of Saturn? Why does it confuse chemists with its own name? And how does a liquid in your nail polish remover end up shaping the chemistry of the upper atmosphere?
From the 17th century, before modern naming rules existed, acetone collected a strange wardrobe of titles. It was called the spirit of Saturn when chemists believed it was a compound of lead. Later it answered to pyro-acetic spirit and pyro-acetic ester. Carl Reichenbach gave it the name mesit, from the Greek word meaning mediator, and even claimed that methyl alcohol was made of mesit and ethyl alcohol. Those mesit roots still echo today in mesitylene and mesityl oxide, both first made from acetone. The name acetone arrived in 1839, chosen because the substance was obtained from acetic acid. There is a quiet trap built into that name. Most compounds carrying the acet- prefix have a 2-carbon chain, but acetone has three carbons. The mismatch has caused confusion ever since, for the simple reason that no ketone can exist with only two carbons. The prefix points to vinegar, called acetum in Latin, the same root that gives us the words acid and acetic. So the name records a relationship to vinegar, not the molecule's actual shape.
Andreas Libavius first produced acetone in 1606 by distilling lead(II) acetate. More than two centuries passed before its true makeup came into focus. In 1832, the French chemist Jean-Baptiste Dumas and the German chemist Justus von Liebig worked out its empirical formula. In 1833, the French chemists Antoine Bussy and Michel Chevreul settled on the name by attaching the suffix -one to the stem of acetic acid, mirroring how a related product, then mistaken for margaric acid, had been named margarone. By 1852, the English chemist Alexander William Williamson recognized that acetone was methyl acetyl, and the following year the French chemist Charles Frederic Gerhardt agreed. The modern structural formula was published in 1865 by the German chemist August Kekule. There is an overlooked figure in this story. Johann Josef Loschmidt had already presented acetone's structure in 1861, but his privately published booklet drew almost no notice. The next great leap would not come from a laboratory bench but from a wartime emergency.
During World War I, Chaim Weizmann developed a biochemical route to make acetone on an industrial scale, a method now known as the Weizmann Process. Instead of distilling acetates, his approach used acetone-butanol-ethanol fermentation driven by the bacterium Clostridium acetobutylicum. The purpose was urgent and military. Britain needed acetone to prepare Cordite, and Weizmann's fermentation helped supply it. The man behind the process would later become the first president of Israel. The fermentation method did not last forever. It was eventually abandoned once newer techniques delivered better yields, handing the work over to a chemistry that still dominates today.
Roughly 83% of all acetone is made through the cumene process, which ties its fate directly to the production of phenol. Benzene is first alkylated with propylene to form cumene, and that cumene is then oxidized by air, splitting into acetone and phenol together. Other routes exist. There is direct oxidation of propylene in the Wacker-Hoechst process, and the hydration of propylene into 2-propanol, which is then dehydrogenated into acetone. The scale is enormous. In 2010 the worldwide production capacity reached an estimated 6.7 million tonnes per year. The United States led with 1.56 million tonnes per year, followed by Taiwan and China. INEOS Phenol stood as the largest producer, holding 17% of global capacity, with Mitsui, Sunoco and Shell each contributing a notable 7 to 8% in 2010. INEOS Phenol also ran the single largest site, turning out 420,000 tonnes per annum in Beveren, Belgium. By the summer of 2011, acetone in the United States was selling for 1100 to 1250 US dollars per tonne.
Humans exhale several milligrams of acetone daily, formed when the body decarboxylates acetoacetate. The same molecule appears whenever ketone bodies break down inside us. Certain habits push that production higher. Prolonged fasting and high-fat, low-carbohydrate dieting can trigger ketosis, in which acetone forms in body tissue. The process can also turn dangerous. Alcoholism and diabetes can lead to ketoacidosis, an uncontrolled ketosis that drives a sharp and potentially fatal rise in blood acidity. Medicine has learned to use this chemistry on purpose. Ketogenic diets that raise ketone bodies, including acetone alongside beta-hydroxybutyric acid and acetoacetic acid, are used to suppress epileptic attacks in children with treatment-resistant epilepsy. Acetone has shown anticonvulsant effects in animal models of epilepsy, without toxicity, when given in millimolar concentrations. One hypothesis holds that the ketogenic diet works by raising acetone in the brain. Children produce more acetone than most adults because of their higher energy needs, and the younger the child, the higher the expected output. That fact carries a reassuring conclusion: children are not uniquely vulnerable to acetone exposure, since external exposures are small next to what the ketogenic diet produces.
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. Acetone dissolves many plastics and some synthetic fibers. It thins polyester resin, cleans the tools used with it, and breaks down two-part epoxies and superglue before they harden. As a heavy-duty degreaser it prepares metal for painting or soldering, and it strips rosin flux after soldering, though it can attack components like polystyrene capacitors. One of its most surprising jobs involves another flammable substance. Although acetone burns easily, it is used to transport and store acetylene safely, a gas that cannot be pressurized on its own. Vessels packed with a porous material are filled with acetone, then acetylene, which dissolves in. One litre of acetone can hold around 250 litres of acetylene at a pressure of 10 bar. In the lab, acetone serves as a polar, aprotic solvent in reactions such as the Jones oxidation. Because it is cheap, volatile, and dissolves or decomposes most laboratory chemicals, an acetone rinse is the standard way to clear residue from glassware before a final wash. It forms no azeotropes with water. Frozen well below minus 78 degrees Celsius, an acetone and dry ice mixture chills many low-temperature reactions. Make-up artists immerse wig and mustache netting in acetone baths to loosen skin adhesive, and it is the main ingredient breaking down nail polish, including gel, dip powder and acrylic.
On the 30th of July 2015, scientists reported a discovery from the first touchdown of the Philae lander on comet 67P. Its COSAC and Ptolemy instruments detected sixteen organic compounds, four of them seen for the first time on a comet, including acetamide, acetone, methyl isocyanate, and propionaldehyde. Acetone is no stranger to nature on Earth either, arising from terrestrial vegetation, undefined ocean processes, the incomplete combustion of biomass, and the oxidation of hydrocarbons in the air. Its most hazardous trait is extreme flammability. In small amounts it burns with a dull blue flame, while larger amounts produce incomplete combustion and a bright yellow flame. Above its flash point of minus 20 degrees Celsius, air mixtures of 2.5 to 12.8% acetone by volume may explode or flash, and vapors can creep along surfaces to distant ignition sources. Yet accidental ignition is rare, and its auto-ignition temperature runs high, around 465 degrees Celsius and quoted as high as 535. Pouring acetone over red-glowing coal will not light it, defeated by the cooling effect of evaporation. In the atmosphere the molecule lingers about two weeks. That long life lets winds carry it into the upper troposphere and lower stratosphere, where it can influence the production of hydrogen radicals and the levels of ozone far above the ground.
Common questions
What is acetone and what is it used for?
Acetone is an organic compound and the simplest, smallest ketone, a colorless, highly volatile, flammable liquid with a pungent odor. About a third of the world's acetone is used as a solvent, with major roles in producing methyl methacrylate and bisphenol A, precursors to widely used plastics.
Who invented the industrial process for making acetone?
Chaim Weizmann developed the biochemical process for industrial acetone production during World War I, known as the Weizmann Process. It used acetone-butanol-ethanol fermentation with Clostridium acetobutylicum bacteria to help the British war effort prepare Cordite, and Weizmann later became the first president of Israel.
Why is acetone in nail polish remover?
Acetone is a main ingredient in many nail polish removers because it breaks down nail polish. It is used for all types of removal, including gel nail polish, dip powder, and acrylic nails.
Is acetone produced naturally in the human body?
Yes, acetone is produced and disposed of in the human body through normal metabolic processes, and small quantities are present naturally in blood and urine. Humans exhale several milligrams of acetone per day, and people with diabetic ketoacidosis produce it in larger amounts.
How is most acetone produced industrially today?
Approximately 83% of acetone is produced via the cumene process, in which benzene is alkylated with propylene to make cumene, which is then oxidized by air to produce acetone and phenol. This ties acetone production directly to phenol production.
Is acetone toxic or dangerous?
Acetone is believed to exhibit only slight toxicity in normal use and is generally recognized to have low acute and chronic toxicity if ingested or inhaled. Its most hazardous property is extreme flammability, and it is an irritant causing mild skin and moderate-to-severe eye irritation.
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