What Is Acetylacetone?
Acetylacetone, an organic compound with the chemical formula CH3COCH2COCH3, is a 1,3-diketone. It appears as a colorless or pale yellow liquid at room temperature, with a ketone-like odor reminiscent of rotting fruit. It is soluble in water and various organic solvents such as ethanol and diethyl ether.
Uses of Acetylacetone
Acetylacetone serves as an extractant for metal ions, forming complexes with many transition metals due to its bidentate ligand capability. These metal complexes have diverse applications, including precursors for catalysts, reaction reagents, NMR shift reagents, and precursors for hydroformylation catalysts. Additionally, acetylacetone is used as an additive in gasoline and lubricating oil, and in the development of dye-sensitized solar cells to enhance titanium dioxide (IV) performance.
Principle of Acetylacetone
1. Properties of Acetylacetone
- Molecular Formula: CH3COCH2COCH3
- Molecular Weight: 100.12
- Melting Point: -23°C
- Boiling Point: 141°C
- Flash Point: 39°C
- Solubility: Soluble in water (16 g/100 mL)
As a 1,3-diketone, acetylacetone exists in keto-enol equilibrium, with the enol form being a C2v symmetric molecule.
2. Synthesis of Acetylacetone
Acetylacetone is produced industrially via thermal rearrangement of isopropenyl acetate. Laboratory methods include the reaction of acetone with acetic anhydride using boron trifluoride as a catalyst and the condensation of acetone and ethyl acetate with an alkali catalyst.
3. Chemical Reactions of Acetylacetone
Acetylacetone forms various metal complexes such as Mn(acac)3 and VO(acac)2. It also reacts with amines and hydrazine to synthesize amine and heterocyclic compounds. Enzymatically, acetylacetone is degraded into acetic acid and 2-oxopropanal.
Types of Acetylacetone
Commercially available as a chemistry reagent, acetylacetone is offered in volumes like 25mL, 100mL, and 500mL. Metal complexes of acetylacetone are also available in various products for both laboratory and industrial uses.