Diacetone alcohol 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 the formula CH₃C(O)CH₂C(OH)(CH₃)₂, sometimes called DAA. This colorless liquid is a common synthetic intermediate used for the preparation of other compounds, and is also used as a solvent.

Synthesis and reactions

: First identified by Heintz, one standard laboratory preparation of DAA entails the Ba(OH)₂-catalyzed condensation of two molecules of

acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...

. It undergoes dehydration to give the α,β-unsaturated ketone called mesityl oxide.

Hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

of diacetone alcohol gives hexylene glycol. Condensation with

urea Urea, also called carbamide (because it is a diamide of carbonic acid), is an organic compound with chemical formula . This amide has two Amine, amino groups (–) joined by a carbonyl functional group (–C(=O)–). It is thus the simplest am ...

gives "diacetone-monourea", i.e. the heterocycle 3,4-dihydro- 4,4,6-trimethyl-2(1H)-pyrimidone.

Uses

Diacetone alcohol is used in

cellulose Cellulose is an organic compound with the chemical formula, formula , a polysaccharide consisting of a linear chain of several hundred to many thousands of glycosidic bond, β(1→4) linked glucose, D-glucose units. Cellulose is an important s ...

ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...

lacquers, particularly of the brushing type, where it produces brilliant gloss and hard film and where its lack of odor is desirable. It is used in lacquer thinners, dopes,

wood stain Wood stain is a type of paint used to colour wood comprising colourants dissolved and/or suspended in a vehicle or solvent. Pigments and/or dyes are largely used as colourants in most stains. The initial application of any paint or varnish is ...

s, wood preservatives and printing pastes; in coating compositions for

paper Paper is a thin sheet material produced by mechanically or chemically processing cellulose fibres derived from wood, Textile, rags, poaceae, grasses, Feces#Other uses, herbivore dung, or other vegetable sources in water. Once the water is dra ...

and textiles; permanent markers; in making artificial

silk Silk is a natural fiber, natural protein fiber, some forms of which can be weaving, woven into textiles. The protein fiber of silk is composed mainly of fibroin and is most commonly produced by certain insect larvae to form cocoon (silk), c ...

and

leather Leather is a strong, flexible and durable material obtained from the tanning (leather), tanning, or chemical treatment, of animal skins and hides to prevent decay. The most common leathers come from cattle, sheep, goats, equine animals, buffal ...

; in imitation gold leaf; in celluloid

cement A cement is a binder, a chemical substance used for construction that sets, hardens, and adheres to other materials to bind them together. Cement is seldom used on its own, but rather to bind sand and gravel ( aggregate) together. Cement mi ...

s; as a preservative for animal tissue; in metal cleaning compounds; in the manufacture of photographic film; and in hydraulic brake fluids, where it is usually mixed with an equal volume of

castor oil Castor oil is a vegetable oil pressed from castor beans, the seeds of the plant ''Ricinus communis''. The seeds are 40 to 60 percent oil. It is a colourless or pale yellow liquid with a distinct taste and odor. Its boiling point is and its den ...

Safety

The {{LD50 (oral, rats) is 4 g/kg.

References

6. Igor Eskendirov, etc. (1995) “Kinetics by Thermometry: An Aldol Condensation Reaction” 1995.Journal of the Chemical Society, Faraday Transactions 91(6), 991-994 Tertiary alcohols Aldols