John Ulric Nef – discovered Nef reaction worked on Isocyanide, Nitroparaffin, Fulminate chemicals

John Ulric Nef – discoverer of Nef reaction

Category : Personalities
Published by : Data Research Analyst, Worldofchemicals.com

Biography & contributions

John Ulric Nef, and American chemist born on June 14, 1862 – died on August 13, 1915. Nef’s major chemistry research works on chemistry of carbon valence, isocyanide, nitroparaffins, fulminates.

Nef also discovered nef reaction in the field of organic chemistry.

His worked on carbon valence and proposed that carbon is having two and four valence numbers.

Facts about nitroparaffins

Nitroparaffins are commonly referred to as nitroalkanes and are versatile solvents which have an electronegative nitro (-NO2) group attached to a methane, ethane or propane molecule. The nitroparaffins are excellent solvents for various resins and polymer compositions in the coating industry, electrostatic spray coatings.

Nitroparaffins are used with triethylaluminium, vanadium, titanium alkyl-metal catalysts salts in the polymerization reactions of alkylene oxides, epichlorohydrin, propylene, butylenes. These are also used to separate lactic acid from fermentation beers, nitrocellulose from nitrating solution, used in diesel fuel to increase power output of engines.

Fulminate

Fulminates were discovered by Edward Charles Howard in 1800.Fulminate are chemical compounds which include the fulminate ion. The fulminate ion, CNO- is a pseudohalic ion, acting like a halogen with its charge and reactivity.

Fulminates can be formed from metals, such as silver and mercury, dissolved in nitric acid and reacted with ethanol. Fulminate is largely the presence of the weak single nitrogen-oxygen bond which leads to its instability. It is very sensitive to heat, shock, or friction and is used in primers, detonators, and blasting caps.

Nef reaction

The Nef reaction is an organic reaction describing the acid hydrolysis of a salt of a primary or secondary nitroalkane to an aldehyde or a ketone and nitrous oxide. John Ulric Nef treated the sodium salt of nitroethane with sulfuric acid resulting in an 85–89% yield of nitrous oxide and at least 70% yield of acetaldehyde.

Nef reaction mechanism includes

The nef reaction mechanism will start with the nitronate salt protonation, which will give nitronic acid. Nitronate salt is once again protonated and resulted in the formation of iminium ion. This intermediate is attacked by water in a nucleophilic addition forming which loses a proton and then water to the 1-nitroso-alkanol. This intermediate rearranges to hyponitrous acid and the oxonium ion which loses a proton to form the carbonyl compound.

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