Acetone oxime (acetoxime) is the

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 (CH₃)₂CNOH. It is the simplest example of a

ketoxime In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula , where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted ...

. It is a white crystalline solid that is soluble in water, ethanol, ether, chloroform, and ligroin. It is used as a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

organic synthesis Organic synthesis is a branch of chemical synthesis concerned with the construction of organic compounds. Organic compounds are molecules consisting of combinations of covalently-linked hydrogen, carbon, oxygen, and nitrogen atoms. Within the gen ...

.Steven M. Weinreb, Kristina Borstnik "Acetone Oxime" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2007. Acetone oxime (acetoxime) was first prepared and named in 1882 by the German chemist

Victor Meyer Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic chemistry, organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meye ...

and his Swiss student Alois Janny. From p. 1324: ''"Die Substanz, welche wir, wegen ihrer nahen Beziehungen zur Acetoximsäure, und da sie keine sauren Eigenschaften besitzt, vorläufig Acetoxim nennen wollen, …"'' (The substance, which we – on account of its close relations to acetoximic acid, and since it possesses no acid properties – will, for the present, name "acetoxime," … )

Preparation

Acetone oxime is synthesized by the condensation 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 ...

and

hydroxylamine Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula . The compound exists as hygroscopic colorless crystals.Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Prof ...

in the presence of HCl:Handbook of Chemistry and Physics :(CH₃)₂CO + H₂NOH → (CH₃)₂CNOH + H₂O It can also be generated via

ammoxidation In organic chemistry, ammoxidation is a process for the production of nitriles () using ammonia () and oxygen (). It is sometimes called the SOHIO process, acknowledging that ammoxidation was developed at Standard Oil of Ohio. The usual substrate ...

of acetone in the presence of hydrogen peroxide.Xinhua Liang, Zhentao Mi, Yaquan Wang, Li Wang, Xiangwen Zhang "Synthesis of acetone oxime through acetone ammoximation over TS-1" Reaction Kinetics and Catalysis Letters Volume 82, pp 333-337

Uses

Acetone oxime is an excellent corrosion inhibitor (deoxidant) with lower toxicity and greater stability compared to the common agent

hydrazine Hydrazine is an inorganic compound with the chemical formula . It is a simple pnictogen hydride, and is a colourless flammable liquid with an ammonia-like odour. Hydrazine is highly hazardous unless handled in solution as, for example, hydraz ...

. It is also useful in the determination of ketones, cobalt and in organic synthesis.Acetone Oxime Properties
additional text.

References

{{reflist Ketoximes