Allyl acetate is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

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

allyl alcohol Allyl alcohol (IUPAC name: prop-2-en-1-ol) is an organic compound with the structural formula . Like many alcohols, it is a water-soluble, colourless liquid. It is more toxic than typical small alcohols. Allyl alcohol is used as a precursor to ...

, which is a useful industrial intermediate. It is the

acetate An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic, or radical base). "Acetate" also describes the conjugate base or ion (specifically, the negatively charged ion called ...

ester of allyl alcohol.

Preparation

Allyl acetate is produced industrially by the gas phase reaction of

propene Propylene, also known as propene, is an unsaturated organic compound with the chemical formula . It has one double bond, and is the second simplest member of the alkene class of hydrocarbons. It is a colorless gas with a faint petroleum-like od ...

in the presence of

acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

using a

palladium Palladium is a chemical element; it has symbol Pd and atomic number 46. It is a rare and lustrous silvery-white metal discovered in 1802 by the English chemist William Hyde Wollaston. He named it after the asteroid Pallas (formally 2 Pallas), ...

catalyst Catalysis () is the increase in rate of a chemical reaction due to an added substance known as a catalyst (). Catalysts are not consumed by the reaction and remain unchanged after it. If the reaction is rapid and the catalyst recycles quick ...

: :C₃H₆ + CH₃COOH + ½ O₂ → CH₂=CHCH₂OCOCH₃ + H₂O This method is advantageous because propene is inexpensive and a green chemical. 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 is an organic compound with the Chemical formula, formula CH3CO2CH=CH2. This colorless liquid is the precursor to polyvinyl acetate, ethylene-vinyl acetate copolymers, polyvinyl alcohol, and other important industrial polymers. Prod ...

is produced similarly, using

ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...

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

: :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 () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...

. Epoxidation by

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

produces

glycidol Glycidol is an organic compound with the formula . The molecule contains both epoxide and alcohol functional groups. Being simple to make and bifunctional, it has a variety of industrial uses. The compound is a colorless, slightly viscous liqui ...

, 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 is the organic compound with the formula C H2=CHCH2 Cl. 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 c ...

. Reaction with

hydrogen cyanide Hydrogen cyanide (formerly known as prussic acid) is a chemical compound with the chemical formula, formula HCN and structural formula . It is a highly toxic and flammable liquid that boiling, boils slightly above room temperature, at . HCN is ...

over copper catalyst yields

allyl cyanide Allyl cyanide is an organic compound with the formula CH2CHCH2CN. Like other small alkyl nitriles, allyl cyanide is colorless and soluble in organic solvents. Allyl cyanide occurs naturally as an antifeedant and is used as a cross-linking agent ...

. :CH₂=CHCH₂OCOCH₃ + HCl → CH₂=CHCH₂Cl + CH₃COOH :CH₂=CHCH₂OCOCH₃ + HCN → CH₂=CHCH₂CN + CH₃COOH

Allyl chloride Allyl chloride is the organic compound with the formula C H2=CHCH2 Cl. 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 c ...

is generally produced directly by the chlorination of propene.

References

{{reflist Acetate esters Allyl compounds