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The Cannizzaro reaction, named after its discoverer Stanislao Cannizzaro, is a chemical reaction which involves the base-induced disproportionation of two molecules of a non-enolizable aldehyde to give a primary alcohol and a carboxylic acid. [1] [2]
In the Cannizzaro reaction, formaldehyde and base react to produce formic acid and methanol, ... (1.0 US fl oz) of 37% formaldehyde solution can cause death.
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]
Stanislao Cannizzaro FRS (/ ˌ k æ n ɪ ˈ z ɑːr oʊ / KAN-iz-AR-oh, [1] also US: /-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 ...
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.
Pentaerythritol was first reported in 1891 by German chemist Bernhard Tollens and his student P. Wigand. [5] It may be prepared via a base-catalyzed multiple-addition reaction between acetaldehyde and 3 equivalents of formaldehyde to give pentaerythrose (CAS: 3818-32-4), followed by a Cannizzaro reaction with a fourth equivalent of formaldehyde to give the final product plus formate ion.
For laboratory use, Grignard reaction of phenylmagnesium bromide (C 6 H 5 MgBr) with formaldehyde and the Cannizzaro reaction of benzaldehyde also give benzyl alcohol. The latter also gives benzoic acid, an example of an organic disproportionation reaction.
In the context of butanol fuel, isobutyraldehyde is of interest as a precursor to isobutanol. E. coli as well as several other organisms has been genetically modified to produce isobutanol. α-Ketoisovalerate, derived from oxidative deamination of valine, is prone to decarboxylation to give isobutyraldehyde, which is susceptible to reduction to the alcohol: [3]