Acetophenone is the 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 the formula
Chemical formula
A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 C6H5C(O)CH3. It is the simplest aromatic ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

. This colourless, viscous liquid is a precursor to useful resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

s and fragrances.


Acetophenone can be obtained by a variety of methods. In industry, acetophenone is recovered as a by-product of the oxidation of ethylbenzene
Ethylbenzene is an organic compound with the formula C6H5CH2CH3. This aromatic hydrocarbon is important in the petrochemical industry as an intermediate in the production of styrene, which in turn is used for making polystyrene, a common plastic material....

, which mainly gives ethylbenzene hydroperoxide for use in the production of propylene oxide
Propylene oxide
Propylene oxide is an organic compound with the molecular formula CH3CHCH2O. This colourless volatile liquid is produced on a large scale industrially, its major application being its use for the production of polyether polyols for use in making polyurethane plastics...


Precursor to resins

Commercially significant resin
Resin in the most specific use of the term is a hydrocarbon secretion of many plants, particularly coniferous trees. Resins are valued for their chemical properties and associated uses, such as the production of varnishes, adhesives, and food glazing agents; as an important source of raw materials...

s are produced from treatment of acetophenone with formaldehyde
Formaldehyde is an organic compound with the formula CH2O. It is the simplest aldehyde, hence its systematic name methanal.Formaldehyde is a colorless gas with a characteristic pungent odor. It is an important precursor to many other chemical compounds, especially for polymers...

 and base. The resulting polymers are conventionally described with the formula [(C6H5C(O)CH]x(CH2)x}n, resulting from aldol condensation
Aldol condensation
An aldol condensation is an organic reaction in which an enol or an enolate ion reacts with a carbonyl compound to form a β-hydroxyaldehyde or β-hydroxyketone, followed by a dehydration to give a conjugated enone....

. These substances are components of coating
Coating is a covering that is applied to the surface of an object, usually referred to as the substrate. In many cases coatings are applied to improve surface properties of the substrate, such as appearance, adhesion, wetability, corrosion resistance, wear resistance, and scratch resistance...

s and ink
Ink is a liquid or paste that contains pigments and/or dyes and is used to color a surface to produce an image, text, or design. Ink is used for drawing and/or writing with a pen, brush, or quill...

s. Modified acetophenone-formaldehyde resins are produced by the hydrogenation of the aforementioned ketone-containing resins. The resulting polyol
A polyol is an alcohol containing multiple hydroxyl groups. In two technological disciplines the term "polyol" has a special meaning: food science and polymer chemistry.- Polyols in food science :...

 can be further crosslinked with diisocyanates. These modified resins are again found in coatings, inks, as well as adhesive
An adhesive, or glue, is a mixture in a liquid or semi-liquid state that adheres or bonds items together. Adhesives may come from either natural or synthetic sources. The types of materials that can be bonded are vast but they are especially useful for bonding thin materials...


Precursor to styrene

In instructional laboratories, acetophenone is converted to styrene in a two step process that illustrates the reduction of carbonyls and the dehydration of alcohols:
4 C6H5C(O)CH3 + NaBH4
Sodium borohydride
Sodium borohydride, also known as sodium tetrahydridoborate, is an inorganic compound with the formula NaBH4. This white solid, usually encountered as a powder, is a versatile reducing agent that finds wide application in chemistry, both in the laboratory and on a technical scale. Large amounts are...

  + 4 H2O → 4 C6H5CH(OH)CH3 + NaOH + B(OH)3

A similar process is used industrially but the hydrogenation step to 1-phenylethanol is done over a copper catalyst.
C6H5CH(OH)CH3 → C6H5CH=CH2 + H2O

Use in pharmaceutical and related areas

Acetophenone is a raw material for the synthesis of some pharmaceuticals
and is also listed as an approved excipient
An excipient is generally a pharmacologically inactive substance used as a carrier for the active ingredients of a medication. In many cases, an "active" substance may not be easily administered and absorbed by the human body; in such cases the substance in question may be dissolved into or...

 by the U.S. FDA. In a 1994 report released by five top cigarette
A cigarette is a small roll of finely cut tobacco leaves wrapped in a cylinder of thin paper for smoking. The cigarette is ignited at one end and allowed to smoulder; its smoke is inhaled from the other end, which is held in or to the mouth and in some cases a cigarette holder may be used as well...

 companies in the U.S., acetophenone was listed as one of the 599 additives to cigarettes.

Niche uses

Acetophenone is used to create fragrances that resemble almond
The almond , is a species of tree native to the Middle East and South Asia. Almond is also the name of the edible and widely cultivated seed of this tree...

, cherry
The cherry is the fruit of many plants of the genus Prunus, and is a fleshy stone fruit. The cherry fruits of commerce are usually obtained from a limited number of species, including especially cultivars of the wild cherry, Prunus avium....

, honeysuckle
Honeysuckles are arching shrubs or twining vines in the family Caprifoliaceae, native to the Northern Hemisphere. There are about 180 species of honeysuckle, 100 of which occur in China; Europe, India and North America have only about 20 native species each...

, jasmine
Jasminum , commonly known as jasmines, is a genus of shrubs and vines in the olive family . It contains around 200 species native to tropical and warm temperate regions of the Old World...

, and strawberry
Fragaria is a genus of flowering plants in the rose family, Rosaceae, commonly known as strawberries for their edible fruits. Although it is commonly thought that strawberries get their name from straw being used as a mulch in cultivating the plants, the etymology of the word is uncertain. There...

. It is used in chewing gum.
Being prochiral
In stereochemistry, prochiral molecules are those that can be converted from achiral to chiral in a single step.If two identical substituents are attached to a sp3-hybridized atom, the descriptors pro-R and pro-S are used to distinguish between the two...

, acetophenone is also a popular test substrate for asymmetric transfer hydrogenation
Transfer hydrogenation
Transfer hydrogenation is the addition of hydrogen to a molecule from a source other than gaseous H2. It is applied in industry and in organic synthesis, in part because of the inconvenience and expense of using gaseous H2...

 experiments. Acetophenone is also commonly used as a flavouring in many cherry flavoured sweets and drinks, as it costs far less and proves as satisfying to consumers this way.

Natural occurrence

Acetophenone occurs naturally in many foods including apple
The apple is the pomaceous fruit of the apple tree, species Malus domestica in the rose family . It is one of the most widely cultivated tree fruits, and the most widely known of the many members of genus Malus that are used by humans. Apple grow on small, deciduous trees that blossom in the spring...

, cheese
Cheese is a generic term for a diverse group of milk-based food products. Cheese is produced throughout the world in wide-ranging flavors, textures, and forms....

, apricot
The apricot, Prunus armeniaca, is a species of Prunus, classified with the plum in the subgenus Prunus. The native range is somewhat uncertain due to its extensive prehistoric cultivation.- Description :...

, banana
Banana is the common name for herbaceous plants of the genus Musa and for the fruit they produce. Bananas come in a variety of sizes and colors when ripe, including yellow, purple, and red....

, beef
Beef is the culinary name for meat from bovines, especially domestic cattle. Beef can be harvested from cows, bulls, heifers or steers. It is one of the principal meats used in the cuisine of the Middle East , Australia, Argentina, Brazil, Europe and the United States, and is also important in...

, and cauliflower
Cauliflower is one of several vegetables in the species Brassica oleracea, in the family Brassicaceae. It is an annual plant that reproduces by seed...



In the late 19th and early 20th centuries, acetophenone was used in medicine. It was marketed as a hypnotic
Hypnotic drugs are a class of psychoactives whose primary function is to induce sleep and to be used in the treatment of insomnia and in surgical anesthesia...

 and anticonvulsant
The anticonvulsants are a diverse group of pharmaceuticals used in the treatment of epileptic seizures. Anticonvulsants are also increasingly being used in the treatment of bipolar disorder, since many seem to act as mood stabilizers, and in the treatment of neuropathic pain. The goal of an...

 under brand name Hypnone. The typical dosage was 0.12 to 0.3 milliliters. It was considered to have superior sedative effects to both paraldehyde
Paraldehyde is the cyclic trimer of acetaldehyde molecules. Formally, it is a derivative of 1,3,5-trioxane. The corresponding tetramer is metaldehyde. A colourless liquid, it is sparingly soluble in water and highly soluble in alcohol. Paraldehyde slowly oxidizes in air, turning brown and producing...

 and chloral hydrate
Chloral hydrate
Chloral hydrate is a sedative and hypnotic drug as well as a chemical reagent and precursor. The name chloral hydrate indicates that it is formed from chloral by the addition of one molecule of water. Its chemical formula is C2H3Cl3O2....

. In humans, acetophenone is metabolized to benzoic acid
Benzoic acid
Benzoic acid , C7H6O2 , is a colorless crystalline solid and the simplest aromatic carboxylic acid. The name derived from gum benzoin, which was for a long time the only source for benzoic acid. Its salts are used as a food preservative and benzoic acid is an important precursor for the synthesis...

, carbonic acid
Carbonic acid
Carbonic acid is the inorganic compound with the formula H2CO3 . It is also a name sometimes given to solutions of carbon dioxide in water, because such solutions contain small amounts of H2CO3. Carbonic acid forms two kinds of salts, the carbonates and the bicarbonates...

, and acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...

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