Allyl acetate is an organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with formula C₃H₅OC(O)CH₃. This colourless liquid is a precursor to especially allyl alcohol

Allyl alcohol

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols,it is a water soluble, colourless liquid, but it is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is used as a precursor to many...

, which is a useful industrial intermediate. It is the acetate ester of allyl alcohol.

Preparation

Allyl acetate is produced industrially by the gas phase reaction of propene in the presence of acetic acid

Acetic acid

Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

 using a palladium

Palladium

Palladium is a chemical element with the chemical symbol Pd and an atomic number of 46. It is a rare and lustrous silvery-white metal discovered in 1803 by William Hyde Wollaston. He named it after the asteroid Pallas, which was itself named after the epithet of the Greek goddess Athena, acquired...

 catalyst:

C₃H₆ + CH₃COOH + ½ O₂ → CH₂=CHCH₂OCOCH₃ + H₂O

This method is advantageous because propene is inexpensive and "green

Green Chemistry

Green Chemistry is a peer-reviewed scientific journal covering any aspect of green chemistry. It is published monthly by the Royal Society of Chemistry and was established in 1999 by James Clark . Articles have to be conceptually accessible to a wide audience...

." Allyl alcohol is also produced primarily from allyl chloride, but production via the hydrolysis of allyl acetate route avoids the use of chlorine, and so is increasing in use.

Vinyl acetate

Vinyl acetate

Vinyl acetate is an organic compound with the formula CH3COOCH=CH2. A colorless liquid with a pungent odor, it is the precursor to polyvinyl acetate, an important polymer in industry.-Production:...

 is produced similarly, using ethylene

Ethylene

Ethylene is a gaseous organic compound with the formula . It is the simplest alkene . Because it contains a carbon-carbon double bond, ethylene is classified as an unsaturated hydrocarbon. Ethylene is widely used in industry and is also a plant hormone...

 in place of propene. These reactions are examples of acetoxylation. The palladium center is then re-oxidized by the O₂ present. The mechanism for the acetoxylation follows a similar pathway, with propene forming a π-allyl bond on the palladium.

Reactions and applications

Allyl acetate can be hydrolyzed to allyl alcohol

Allyl alcohol

Allyl alcohol is an organic compound with the structural formula CH2=CHCH2OH. Like many alcohols,it is a water soluble, colourless liquid, but it is more toxic than typical small alcohols. Allyl alcohol is used as a raw material for the production of glycerol, but is used as a precursor to many...

:

CH₂=CHCH₂OCOCH₃ + H₂O → CH₂=CHCH₂OH + CH₃COOH

Allyl alcohol is a precursor for some specialty polymers, mainly for drying oils. Allyl alcohol is also a precursor to synthetic glycerol

Glycerol

Glycerol is a simple polyol compound. It is a colorless, odorless, viscous liquid that is widely used in pharmaceutical formulations. Glycerol has three hydroxyl groups that are responsible for its solubility in water and its hygroscopic nature. The glycerol backbone is central to all lipids...

. Epoxidation by hydrogen peroxide

Hydrogen peroxide

Hydrogen peroxide is the simplest peroxide and an oxidizer. Hydrogen peroxide is a clear liquid, slightly more viscous than water. In dilute solution, it appears colorless. With its oxidizing properties, hydrogen peroxide is often used as a bleach or cleaning agent...

 produces glycidol

Glycidol

Glycidol is an organic compound that contains both epoxide and alcohol functional groups. Being bifunctional, it has a variety of industrial uses...

, which undergoes hydrolysis to glycerol.

CH₂=CHCH₂OH + HOOH → CH₂OCHCH₂OH + H₂O

CH₂OCHCH₂OH + H₂O → C₃H₅(OH)₃

Synthetic glycerol tends to be used in cosmetics and toiletries whereas glycerol from the hydrolysis of fats is used in food.

Substitution reactions

Substitution of the acetate group in allyl acetate using hydrogen chloride yields allyl chloride

Allyl chloride

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene.-Production:Allyl...

. Reaction with hydrogen cyanide over copper catalyst yields allyl cyanide.

CH₂=CHCH₂OCOCH₃ + HCl → CH₂=CHCH₂Cl + CH₃COOH

CH₂=CHCH₂OCOCH₃ + HCN → CH₂=CHCH₂CN + CH₃COOH

Allyl chloride

Allyl chloride

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene.-Production:Allyl...

is generally produced directly by the chlorination of propene.