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Concept
Acrylamide
Summary
Acrylamide (or acrylic amide) is an organic compound with the chemical formula CH2=CHC(O)NH2. It is a white odorless solid, soluble in water and several organic solvents. From the chemistry perspective, acrylamide is a vinyl-substituted primary amide (CONH2). It is produced industrially mainly as a precursor to polyacrylamides, which find many uses as water-soluble thickeners and flocculation agents.
Acrylamide forms in burnt areas of food, particularly starchy foods like potatoes, when cooked with high heat, above . Despite health scares following its discovery in 2002, dietary acrylamide is thought unlikely to be carcinogenic for humans; Cancer Research UK categorized the idea that burnt food causes cancer as a "myth".
Acrylamide can be prepared by the hydration of acrylonitrile, which is catalyzed enzymatically:
CH2=CHCN + H2O → CH2=CHC(O)NH2
This reaction also is catalyzed by sulfuric acid as well as various metal salts. Treatment of acrylonitrile with sulfuric acid gives acrylamide sulfate, . This salt can be converted to acrylamide]with base or to methyl acrylate with methanol.
The majority of acrylamide is used to manufacture various polymers, especially polyacrylamide. This water-soluble polymer, which has very low toxicity, is widely used as thickener and flocculating agent. These functions are valuable in the purification of drinking water, corrosion inhibition, mineral extraction, and paper making. Polyacrylamide gels are routinely used in medicine and biochemistry for purification and assays.
Acrylamide can arise in some cooked foods via a series of steps by the reaction of the amino acid asparagine and glucose. This condensation, one of the Maillard reactions, followed by dehydrogenation produces N-(D-glucos-1-yl)-L-asparagine, which upon pyrolysis generates some acrylamide.
The discovery in 2002 that some cooked foods contain acrylamide attracted significant attention to its possible biological effects.
Official source
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