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A short class with Sarah and her students. The other ways are under More.
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What is the main liquid in nail-polish remover?
Acetone, which is propanone.
Why is acetone such a good solvent for so many things?
Its C=O group is polar, so it attracts polar substances and mixes with water, but its two methyl groups attract oily, non-polar substances too.
Right, and it evaporates quickly, so the surface dries fast. Where else would you find acetone in a workshop?
In acetylene cylinders. The acetylene is dissolved in acetone so it can be stored safely under pressure.
Exactly. On its own, compressed acetylene can explode.
Which ketone ends up in your nylon jacket?
Cyclohexanone. It is turned into caprolactam for nylon-6, and into adipic acid for nylon-6,6.
And what does acetone become in industry?
Chloroform and iodoform by the haloform reaction, the monomer for Perspex, and bisphenol A for polycarbonate plastics.
Good. So a ketone is often a stepping stone rather than the final product.
Like a raw ingredient that gets cooked into many different dishes.
Exactly.
Name a ketone you might find in a medicine cabinet.
Camphor, in balms and ointments.
Which sugar has a ketone group?
Fructose. Glucose has an aldehyde group instead.
Why might a doctor notice a fruity smell on the breath of a patient with uncontrolled diabetes?
The body is breaking down fat and making ketone bodies, including acetone, and some acetone is breathed out.
Exactly. And why must acetone bottles be kept away from flames?
It is highly flammable, and its vapour can travel along the bench to a flame.
it dissolves both polar and non-polar substances and evaporates quickly.
acetylene is dissolved in acetone inside cylinders so that it can be stored safely.
acetone gives chloroform, iodoform, Perspex and bisphenol A; cyclohexanone gives nylon.
acetophenone, benzophenone, carvone, muscone and camphor.
fructose and steroid hormones such as testosterone contain ketone groups.
Nail-polish remover is mostly acetone, which dissolves the dried polymer film of the polish.
Welders' acetylene cylinders contain a porous filling soaked in acetone, in which acetylene dissolves under pressure.
Iodoform, once used as an antiseptic, can be made from acetone: CH3COCH3 + 3I2 + 4NaOH → CHI3 + CH3COONa + 3NaI + 3H2O.
Acetone wipes the polish away and keeps the acetylene safe all day.
Cyclohexanone dreamed of becoming clothing. It changed into caprolactam, linked hands with thousands of copies of itself and finally became a strong nylon rope.
Paint, Plastic, Perfume: the three P's of ketone uses (solvents, raw materials for plastics, fragrances).
C.A.P. - Chloroform, Acetylene storage, Perspex: three big jobs for acetone.
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Most widely used ketone solvent
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Why is acetylene dissolved in acetone in gas cylinders?
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Ketone used to make nylon
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Ketone used in medicinal balms and burnt in worship
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A sugar that is a ketose
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A liquid that dissolves other substances to form a solution.
The reaction of a methyl ketone with a halogen and alkali, giving a haloform such as chloroform (CHCl3) or iodoform (CHI3).
A clear acrylic plastic, poly(methyl methacrylate), made from a monomer prepared from acetone.
A cyclic amide made from cyclohexanone and polymerised to nylon-6.
Acetone and related compounds made when the body breaks down fat for energy.
A sugar with a ketone group, such as fructose.
Easily set on fire.
Ketones are valued mainly as solvents and as raw materials for plastics, fibres and other chemicals. Some, such as camphor and muscone, are used in medicine and perfumery, and ketone groups also appear in sugars and hormones.
Propanone (acetone) is the most important ketone. It dissolves paints, varnishes, lacquers and nail polish, it is used to store acetylene safely in cylinders, and it is a raw material for chloroform, iodoform, Perspex (through methyl methacrylate) and bisphenol A. Butanone is another common industrial solvent, cyclohexanone is a key raw material for nylon, acetophenone and benzophenone are used in perfumery, and natural ketones such as camphor, carvone and muscone are used in medicines, flavours and perfumes. The lesson links these uses to the properties of ketones and explains the fire and health hazards of ketone solvents.
Ketones are useful because the polar carbonyl group sits between two carbon groups: this makes small ketones excellent, quick-drying solvents, makes the carbonyl group a reactive starting point for building larger molecules, and gives many ketones the pleasant smells used in perfumes.