Cyclopentanone is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the formula (CH₂)₄CO. This cyclic

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

is a colorless volatile liquid.

Preparation

Upon treatment with

barium hydroxide Barium hydroxide is a chemical compound with the chemical formula Ba(OH)2. The monohydrate (''x'' = 1), known as baryta or baryta-water, is one of the principal compounds of barium. This white granular monohydrate is the usual commercial form. P ...

at elevated temperatures,

adipic acid Adipic acid or hexanedioic acid is the organic compound with the formula (CH2)4(COOH)2. From an industrial perspective, it is the most important dicarboxylic acid: about 2.5 billion kilograms of this white crystalline powder are produced annuall ...

undergoes

ketonization In organic chemistry, ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction and a decarboxylation converting two equivalents of a carboxylic acid () to a symmetric ketone () by the application of heat w ...

to give cyclopentanone: :(CH₂)₄(CO₂H)₂ → (CH₂)₄CO + H₂O + CO₂

Uses

Cyclopentanone is common precursor to fragrances, especially those related to

jasmine Jasmine ( taxonomic name: ''Jasminum''; , ) is a genus of shrubs and vines in the olive family (Oleaceae). It contains around 200 species native to tropical and warm temperate regions of Eurasia, Africa, and Oceania. Jasmines are widely cultiva ...

and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone.Johannes Panten and Horst Surburg "Flavors and Fragrances, 2. Aliphatic Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2015, Wiley-VCH, Weinheim. It is a versatile synthetic intermediate, being a precursor to

cyclopentobarbital Cyclopentobarbital sodium (Cyclopal, Dormisan) is a barbiturate derivative invented in the 1940s. It has sedative and anticonvulsant properties, and was used primarily as an anaesthetic in veterinary medicine. Cyclopal is considered similar in e ...

Cyclopentanone is also used to make

cyclopentamine Cyclopentamine (trade names Clopane, Cyclonarol, Cyclosal, Cyklosan, Nazett, Sinos, among others) is a sympathomimetic alkylamine, classified as a vasoconstrictor. Cyclopentamine was indicated in the past as an over-the-counter (OTC) medication ...

, the pesticide

pencycuron Pencycuron is a phenylurea fungicide developed by Bayer Crop Science Bayer AG (, commonly pronounced ; ) is a German multinational pharmaceutical and biotechnology company and one of the largest pharmaceutical companies in the world. Hea ...

, and

pentethylcyclanone Pentethylcyclanone is an antitussive medication A medication (also called medicament, medicine, pharmaceutical drug, medicinal drug or simply drug) is a drug used to diagnose, cure, treat, or prevent disease. Drug therapy ( pharmacother ...

References

{{Authority control 5 Ketone solvents Perfume ingredients Cyclopentanes