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Formaldehyde is readily oxidized by atmospheric oxygen into formic acid. For this reason, commercial formaldehyde is typically contaminated with formic acid. Formaldehyde can be hydrogenated into methanol. In the Cannizzaro reaction, formaldehyde and base react to produce formic acid and methanol, a disproportionation reaction.
Neopentyl glycol is synthesized industrially by the aldol reaction of formaldehyde and isobutyraldehyde. This creates the intermediate hydroxypivaldehyde, which can be converted to neopentyl glycol by either a Cannizzaro reaction with excess formaldehyde, or by hydrogenation using palladium on carbon. [2]
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl (C=O) functional group by formaldehyde (H−CHO) and a primary or secondary amine (−NH 2) or ammonia (NH 3). [1] The final product is a β-amino-carbonyl compound also known as a Mannich base.
The oxidation state of oxygen is − 1 ⁄ 2 in the superoxide free radical anion, −1 in hydrogen peroxide and 0 in dioxygen. In the Cannizzaro reaction, an aldehyde is converted into an alcohol and a carboxylic acid. In the related Tishchenko reaction, the organic redox reaction product is the corresponding ester.
Stanislao Cannizzaro FRS (/ ˌ k æ n ɪ ˈ z ɑːr oʊ / KAN-iz-AR-oh, [1] US also /-ɪ t ˈ s ɑːr-/-it-SAR-, [2] Italian: [staniˈzlaːo kannitˈtsaːro]; 13 July 1826 – 10 May 1910) was an Italian chemist. He is famous for the Cannizzaro reaction and for his influential role in the atomic-weight deliberations of the Karlsruhe Congress ...
In organic synthesis, the Casiraghi formylation is the formation of a salicylaldehyde from a phenol and paraformaldehyde.The reaction requires a strong Brønsted base and a weak Lewis acid, and gives a methanol coproduct: [1]
Sodium formate is also unavoidably formed as a by-product in the final step of the pentaerythritol synthesis and in the crossed Cannizzaro reaction of formaldehyde with the aldol reaction product trimethylol acetaldehyde [3-hydroxy-2,2-bis(hydroxymethyl)propanal].
Cannizzaro's chemical interests had originally centered on natural products and on reactions of aromatic compounds; in 1853 he discovered that when benzaldehyde is treated with concentrated base, both benzoic acid and benzyl alcohol are produced—a phenomenon known today as the Cannizzaro reaction. In his 1858 pamphlet, Cannizzaro showed that ...