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Although the classic substrate for the Criegee oxidation are 1,2-diols, the oxidation can be employed with β-amino alcohols, [10] α-hydroxy carbonyls, [11] and α-keto acids, [12] In the case of β-amino alcohols, a free radical mechanism is proposed. The Criegee oxidation can also be employed with 2,3-epoxy alcohols forms α-acetoxy carbonyls.
Ethylene glycol (IUPAC name: ethane-1,2-diol) is an organic compound (a vicinal diol [7]) with the formula (CH 2 OH) 2. It is mainly used for two purposes: as a raw material in the manufacture of polyester fibers and for antifreeze formulations. It is an odorless, colorless, flammable, viscous liquid.
Propylene glycol (IUPAC name: propane-1,2-diol) is a viscous, colorless liquid. It is almost odorless and has a faintly sweet taste. Its chemical formula is CH 3 CH(OH)CH 2 OH. As it contains two alcohol groups, it is classified as a diol. An aliphatic diol may also be called a glycol.
Propane-2,2-diol, an example of a geminal diol. A geminal diol has two hydroxyl groups bonded to the same atom. These species arise by hydration of the carbonyl compounds. The hydration is usually unfavorable, but a notable exception is formaldehyde which, in water, exists in equilibrium with methanediol H 2 C(OH) 2
[1,3] diols have a tendency to eliminate water following the monooxidation by Fétizon's reagent to form an enone. [8] Upon oxidation with Fetizon's reagent, a 1,3 diol may eliminate water to produce an enone. Under differing structural conditions, [1,2] diols can form diketones in the presence of Fétizon's reagent.
The oxidation of primary alcohols to carboxylic acids normally proceeds via the corresponding aldehyde, which is transformed via an aldehyde hydrate (gem-diol, R-CH(OH) 2) by reaction with water. Thus, the oxidation of a primary alcohol at the aldehyde level without further oxidation to the carboxylic acid is possible by performing the reaction ...
Glycol cleavage is a specific type of organic chemistry oxidation. The carbon–carbon bond in a vicinal diol (glycol) is cleaved and instead the two oxygen atoms become double-bonded to their respective carbon atoms. Depending on the substitution pattern in the diol, these carbonyls will be ketones and/or aldehydes. [1]
Glyoxal was first prepared and named by the German-British chemist Heinrich Debus (1824–1915) by reacting ethanol with nitric acid. [4] [5]Commercial glyoxal is prepared either by the gas-phase oxidation of ethylene glycol in the presence of a silver or copper catalyst (the Laporte process) or by the liquid-phase oxidation of acetaldehyde with nitric acid.