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Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH 2 =CHC(O)NH 2.It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH 2).
The carboxyl group of acrylic acid can react with ammonia to form acrylamide, or with an alcohol to form an acrylate ester. Acrylamide and methyl acrylate are commercially important examples of α,β-unsaturated amides and α,β-unsaturated esters, respectively. They also polymerize readily.
The reaction proceeds via N-hydroxymethylacrylamide, which can be detected in alkaline solution and decomposes in acid to give N,N′-methylenebisacrylamide. Using acrylamide and paraformaldehyde in 1,2-dichloroethane gives a clear solution upon heating, from which MBA crystallizes.
Acrylates are industrially prepared by treating acrylic acid with the corresponding alcohol in presence of a catalyst. The reaction with lower alcohols ( methanol , ethanol ) takes place at 100–120 °C with acidic heterogeneous catalysts ( cation exchanger ).
Hydrolysis with sulfuric acid gives acrylamide sulfate, CH=CHC(O)NH 2 ·H 2 SO 4. This salt can be converted to acrylamide with treatment with base or to methyl acrylate by treatment with methanol. [5] The reaction of acrylonitrile with protic nucleophiles is a common route to a variety of specialty chemicals. The process is called cyanoethylation:
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AMPS is made by the Ritter reaction of acrylonitrile and isobutylene in the presence of sulfuric acid and water. [2] The recent patent literature [3] describes batch and continuous processes that produce AMPS in high purity (to 99.7%) and improved yield (up to 89%, based on isobutene) with the addition of liquid isobutene to an acrylonitrile / sulfuric acid / phosphoric acid mixture at 40°C.