Acetylacetone

Acetylacetone is an organic compound with the chemical formula .mw-parser-output .template-chem2-su{display:inline-block;font-size:80%;line-height:1;vertical-al

Acetylacetone
Skeletal formula of acetylacetone in its ketone form.

Acetylacetone is an organic compound with the chemical formula (CH3CO)2CH2. It is the simplest β-diketone, meaning it has two C=O functional groups that are separated by one carbon atom (a methylene bridge).

Structure

Enol (left) and ketone (right) forms of acetylacetone.

Most ketones show tautomerism: the molecules change back and forth between two different chemical structures. Ketones have both the ketone form, where the double bond is between carbon and oxygen, and an enol form where the double bond is between two carbon atoms.

While usually the ketone form is more stable, pure acetylacetone is more stable as the enol. When in a solution, the form depends on the solvent, with more ketone found in more polar solvents.[1]

Properties

Skeletal formula of acetylacetonate, showing resonance.

Acetylacetone is a weak acid. Its conjugate base, acetylacetonate, has resonance between the carbon-oxygen bonds and the central carbon-carbon bonds, which helps stabilise the anion.

Acetylacetonate is a bidentate ligand, forming coordination complexes called metal acetylacetonates.

Preparation

Acetylacetone can be prepared by many routes. Industrially, it is made by rearrangement of isopropenyl acetate.[2] In the laboratory, it can be made from acetone by multiple routes: a reaction with acetic anhydride and a Lewis acid like boron trifluoride, or a reaction with ethyl acetate and an alkoxide base like sodium ethoxide via an enolate intermediate.[3]

Sources

  1. ↑ Cortney, Candice H.; Krishnan, V. V. (2020). "Keto–Enol Tautomerization of Acetylacetone in Mixed Solvents by NMR Spectroscopy. A Physical Chemistry Experiment on the Application of the Onsager-Kirkwood Model for Solvation Thermodynamics". Journal of Chemical Education. 97 (3): 825–830. Bibcode:2020JChEd..97..825C. doi:10.1021/acs.jchemed.9b00737.
  2. ↑ Zhou, Yifei; Ding, Yamei; Gao, Wenjie; Wang, Jichao; Liu, Xiutao; Xian, Mo; Feng, Xinjun; Zhao, Guang (2020). "Biosynthesis of acetylacetone inspired by its biodegradation". Biotechnology for Biofuels. 13 (1): 88. Bibcode:2020BB.....13...88Z. doi:10.1186/s13068-020-01725-9. PMC 7226712. PMID 32454892.
  3. ↑ C. E. Denoon, Jr. (1940). "Acetylacetone". Organic Syntheses. 20: 6.

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