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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]
Formaldehyde is one of the main disinfectants recommended for destroying anthrax. [55] Formaldehyde is also approved for use in the manufacture of animal feeds in the US. It is an antimicrobial agent used to maintain complete animal feeds or feed ingredients Salmonella negative for up to 21 days. [56]
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 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]
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.
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]
The formose reaction is of importance to the question of the origin of life, as it leads from simple formaldehyde to complex sugars like ribose, a building block of RNA.In one experiment simulating early Earth conditions, pentoses formed from mixtures of formaldehyde, glyceraldehyde, and borate minerals such as colemanite (Ca 2 B 6 O 11 5H 2 O) or kernite (Na 2 B 4 O 7). [6]
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.