Acetone: Structure, Preparations, Physical Properties, Uses, practice problems and Frequently Asked Questions

Have you ever wondered why nail polish is removed with nail polish remover instead of water?

Yes, nail polish remover contains acetone as a solvent.

In the modern world, nail polish is commonly used to decorate fingernails and toenails. Most nail polishes are a mixture of polymers that usually fade over time when exposed to other chemicals. Nail polish remover comes in handy when someone decides to try a new nail polish or when the old nail polish begins to fade. The main component of nail polish remover is acetone. It is less toxic than methanol, benzene and tetrachloroethane and is one of the main reasons why acetone is used in nail polish remover. This flammable compound dissolves the paint by reacting with the molecules on the surface and providing electrons from the oxygen present in the carbonyl group. It mixes well with acrylics and paints, resulting in a soft, malleable mixture. Most compounds destroy the surface of the paint, but acetone mixes perfectly with the paint and cleans it. Therefore, it minimizes damage and can be easily removed with a scraper or cotton wool.

Table of content

Acetone
Structure of acetone
Preparations of acetone
Physical properties of acetone
Uses of acetone in daily life
Practice problems
Frequently asked questions

Acetone

Acetone, also known as propanone, is an organic compound with a chemical formula (CH3)2CO. A colorless, pungent odor may appear when nail polish remover is used. Acetone is very important in chemistry because of its composition and its molecular structure. The lone pairs present on the oxygen atom of acetone can partially attract hydrogen atoms and form hydrogen bonds. This property makes acetone the preferred solvent in the industry. For example, acetone is preferred over water in chromatography because it can dissolve both polar and non-polar dyes during analysis.

It is important to note that when acetone is dissolved in water, the acetone molecules do not dissociate into ions. However, they are completely mixed to form a non-uniform mixture. The two methyl groups present in the acetone molecule are non-polar and dissolve non-polar compounds, while the carbonyl group present in the center is polar and dissolves polar compounds.

Acetone is a preferred solvent in the industry due to this characteristic. For example, acetone is favoured over water when doing chromatography because it may dissolve both polar and nonpolar pigments in the analysis. It is crucial to understand that when acetone is dissolved in water, its molecules do not separate into ions but rather totally combine to form a heterogeneous mixture. While the carbonyl group in the heart of the acetone molecule is polar and dissolves polar compounds, the two methyl groups in the acetone molecule are non-polar and dissolve non-polar compounds.

Another factor that makes acetone a good solvent is its miscibility with other polar compounds, especially water, and some other organic compounds. This allows you to produce different types of industrial, household and experimental solvents, depending on the application you need. Acetone is non-toxic, organic, strong and easily miscible with other substances. Acetone is a very important chemical in the chemical industry, but some household items also contain acetone.

Acetone's miscibility with other polar molecules, particularly water, and a number of other organic compounds, makes it an excellent solvent. This enables us to create various industrial, domestic, and laboratory solvents depending on the use. Since acetone is organic, strong, and easily miscible with other chemicals, it has a relatively low hazardous profile. Acetone is a chemical that is very important to the chemical industry, but it is also present in many everyday things. Let's look at a few instances when we might use acetone in our daily lives.

Structure of acetone

Preparation of acetone

Nearly 90% of acetone production is done through Cumene. During this process, acetone is produced together with phenol. The most production process includes the reaction of both propylene and benzene in the presence of dil. sulphuric acid. Cumene gets oxidized within the liquid phase into Cumene hydroperoxide. It then gets cleaved in the presence of sulphuric acid to phenol and acetone. Approximately 0.62% plenty of acetone gets produced with each ton of phenol.

Physical properties of acetone

Appearance: Colorless liquid

Acetone boiling point: 56.05^oC

Melting point: -94.7^oC

Solubility: Miscible with water, benzene, methanol, ethanol, chloroform

Density: 784 Kg m^-3

Taste: Sweetish in taste

Odor: Fruity, pungent, irritating.

Molecular weight: 58.08 g mol^-1

Acidity: 19.2 PKa

Basicity: -5.2 for the conjugate base

Refractive Index: 1.35 nD.

Uses of acetone in daily life

Cosmetics

Acetone is not only an essential ingredient in nail polish remover, but it is also used in the manufacture of several other cosmetics. Widely used as a solvent and denaturant in the cosmetics industry. From wet wipes to hair dyes, acetone is a common chemical used in the manufacturing process. In some countries, a mixture of acetone and dry ice is used as a dermatological treatment called "slush facial" and promises to heal common skin problems such as acne, chloasma, eczema, rosacea and sunburn. A small amount of acetone is absorbed through the skin and enters the bloodstream, but it is usually harmless. However, at high concentrations, acetone can cause extreme redness, irritation, and dryness of the skin. Leaving acetone on the skin for a long period of time can cause dermatitis.

Varnish Remover

Looking at the furniture in the house, the wood in the furniture may appear to be covered with some protective film. This protective film is called a varnish. Wood varnish is an almost essential part of any woodwork. This is a common process defined by the application of a resinous substance with a protective function that gives the furniture a glossy appearance. However, the paint also deteriorates over time and appears to be rusted and dirty. This problem does not occur in common furniture for a long time, but it can spoil the appearance of oil paint masterpieces.

You might have noticed that the wood in the furniture appears to be protected by a film of some kind. Varnish is the name for this shielding layer. Any woodwork would be incomplete without wood varnish. It is a generic technique that involves coating the furniture with a resin substance that serves as protection and gives it a shiny appearance. However, varnish also ages over time and begins to look discoloured and rusted. While this issue might not surface in regular furniture for a while, it might ruin the appearance of an oil painting masterpiece.

Acetone is one of the most preferred chemicals for removing rotten paint. For furniture, rub a soft, fine steel wool pad moistened with acetone against the wood. For oil paintings, apply acetone with a paintbrush. Naturally occurring oils in many exotic woods can weaken the adhesive strength of water-based adhesives and varnishes and significantly slow the curing of oils and varnishes. Acetone is one of the most effective solvents for paint removal due to its ability to mix effectively with mineral oil. Acetone is a volatile compound, so it removes the mineral spirit and dries quickly.

One of the most popular chemicals for removing corroded paint is acetone. Rub a gentle, fine steel wool pad against the wood of furniture using acetone to wet the pad. Use a paintbrush to apply acetone to oil paintings. Oils that are naturally present in many exotic woods can greatly reduce the curing of oils and varnishes and decrease the adhesion of water-based adhesives and varnishes. Due to its propensity to combine well with mineral oil, acetone is one of the best solvents for removing paint. Since acetone is a volatile substance, it quickly dries and eliminates the mineral spirit.

Practice problems

Q1. Which of the following methods is used for the manufacture of acetone?

(A) Catalytic dehydrogenation of isopropanol

(B) Oxidation of butane

(D) Hydration of propylene

Answer: (D)

Solution: Acetone is widely manufactured by catalytic dehydrogenation of isopropanol in the presence of .

Q2. How much percentage purity of acetone can be obtained by dehydrogenation of isopropanol?

(A) 50%

(B) 60%

(D) 99%

Answer: (D)

Solution: Acetone produced is 99% pure with 90% yield. Fractionalization increases the purity of acetone.

Q3. What is the IUPAC name of acetone?

(A) 2-propanone

(B) 2-butanone

(D) 3-hexanone

Answer: (A)

Solution: The formula of acetone is CH₃(CO) CH₃ and IUPAC name is 2-propanone.

Q4. Which is true about acetone?

(A) It has carbon double bonded to oxygen

(B) It does not mix with water

(D) None of these

Answer: (A)

Solution: If we look at the structure of acetone it has carbon double bonded to oxygen and it has only three carbon atoms and it will mix with water as both are polar solvents..

Frequently asked questions:

Question 1. What is pure acetone?
Answer: In chemistry, a pure chemical compound is a chemical substance which contains only one substance and a particular set of molecules or ions. Pure acetone contains only the molecules or ions of acetone.

A pure chemical compound, as used in chemistry, is a substance that comprises only one ingredient and a certain collection of molecules or ions. Only the acetone molecules or ions are present in pure acetone.

Question 2. What are the health hazards of acetone?
Answer: Acetone is highly flammable, but generally has low acute and chronic toxicity. Inhaling acetone can cause sore throat and cough.

Short-term inhalation of moderate to large amounts of acetone can irritate the nose, throat, lungs and eyes.

It can also cause headaches, dizziness, confusion, pulse rate, nausea, vomiting, blood effects, fainting, coma, and shortened menstrual cycles in women.

Question 3. Why does acetone not form an intermolecular hydrogen bond?
Answer: The polar carbonyl group of acetone molecules permits them to accept hydrogen bonds from other molecules. But acetone molecules do not have any polar N-H or O-H bonds, hence it cannot form hydrogen bonds with other acetone molecules.

Question 4. What is the keto-enol tautomerism of acetone?
Answer: As in the case with most ketones, acetone exhibits keto-enol tautomerism in which the “keto” structure is in equilibrium with the enol structure. Just 0.00000024 per cent of the molecules are in the form of enol in acetone vapor at room temperature.