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Under ideal conditions the reaction produces 50% of both the alcohol and the carboxylic acid (it takes two aldehydes to produce one acid and one alcohol). [5] This can be economically viable if the products can be separated and both have a value; the commercial conversion of furfural into furfuryl alcohol and 2-furoic acid is an example of this ...
Gaseous formaldehyde polymerizes at active sites on vessel walls, but the mechanism of the reaction is unknown. [45] Small amounts of hydrogen chloride , boron trifluoride , or stannic chloride present in gaseous formaldehyde provide the catalytic effect and make the polymerization rapid.
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
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.
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]
Another route entails hydrogenation of benzaldehyde, a by-product of the oxidation of toluene to benzoic acid. [ 5 ] 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 reaction is named after Russian organic chemist Vyacheslav Tishchenko, who discovered that aluminium alkoxides are effective catalysts for the reaction. [1] [2] [3] In the related Cannizzaro reaction, the base is sodium hydroxide and then the oxidation product is a carboxylic acid and the reduction product is an alcohol.
The direct reaction between phenol and paraformaldehyde is possible via the Casiraghi formylation, [4] but other methods apply masked forms of formaldehyde, in part to limit the formation of phenol formaldehyde resins. Aldehydes are strongly deactivating and as such phenols typically only react once.