Hexane-2,5-dione
- Hexan- 2 ,5 -dione ( IUPAC )
- Acetonylacetone
- 2.5 Diketohexan
- 1,2- Diacetylethan
- α, β - Diacetylethan
- Diacetonyl
- 2.5 Dioxohexan
Clear, colorless, aromatic smelling liquid
Liquid
0.974 g · cm -3
-5.4 ° C
0.6 mbar (20 ° C)
Soluble in water: ≥ 100 g · l-1 (22 ° C)
1.423 (20 ° C, 589 nm)
Risk
1600 mg · kg -1 ( LD50, rat, oral)
Template: Infobox chemical / molecular formula search available
2,5-hexanedione is a diketone, which is a toxic for the human body metabolites of hexane with molecular formula C6H10O2.
Production and representation
The appearance of the 2.5 - Hexandions carried out by the alkaline hydrolysis of Diacetylbernsteinsäureester and subsequent heating ( ketone cleavage).
2,5-hexanedione can also be prepared by oxidation of Allylaceton.
The synthesis is possible by the oxidation of 2,5- dimethylfuran.
Another synthetic route starting from ethyl acetoacetate with propylene oxide has also been described. The condensation product, α - aceto- γ -valerolactone is reacted with dilute hydrochloric acid to give 2- hydroxy-5 -hexanone, which is finally oxidized with sodium dichromate and sulfuric acid to 2,5-hexanedione.
Properties
2,5-hexanedione reacted inter alia with the functional group of the amines, such as those found in proteins, for example. There it causes crosslinking of the molecules and loss of protein functionality. Networking with the α - amino acid lysine then leads to the formation of the aromatic 2,5 - dimethylpyrrol.
Use
The 2,5-hexanedione is used as a solvent for cellulose acetate, tanning agents, paints and coatings. As a protective group for primary amines and as an intermediate in organic synthesis as well as for the production of pharmaceuticals it is used.
Biological Significance
The metabolite 2,5-hexanedione is an intermediate in the course of diagenesis of the hexane to give 3- methylcyclopent -2 -en -1-one by intramolecular aldol condensation.
Safety
It may cause human irritation of eyes, skin and mucous membranes, degreasing and orange - brown skin inflammation and loss of consciousness. In the human body 2,5-hexanedione occurs as a metabolite of hexane and is excreted in the urine. 2,5 -hexanedione is significantly more toxic than the n-hexane, and even passes through the cross-linking reactions lead to irreparable nerve damage.
2,5-hexanedione also acts as a toxic effect on the spermatogenesis of a damage of the Sertoli cells that form the epithelium of the seminiferous tubules in the seminiferous tubules.