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".
Production
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.
Uses
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.
Toxicity and carcinogenicity
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. IARC, NTP, and the EPA have classified it as a probable carcinogen, although epidemiological studies (as of 2019) suggest that dietary acrylamide consumption does not significantly increase people's risk of developing cancer.
Europe
According to the EFSA, the main toxicity risks of acrylamide are "Neurotoxicity, adverse effects on male reproduction, developmental toxicity and carcinogenicity". However, according to their research, there is no concern on non-neoplastic effects. Furthermore, while the relation between consumption of acrylamide and cancer in rats and mice has been shown, it is still unclear whether acrylamide consumption has an effect on the risk of developing cancer in humans, and existing epidemiological studies in humans are very limited and do not show any relation between acrylamide and cancer in humans. Food industry workers exposed to twice the average level of acrylamide do not exhibit higher cancer rates.
HEATOX (heat-generated food toxicants) study in Europe
The Heat-generated Food Toxicants (HEATOX) Project was a European Commission-funded multidisciplinary research project running from late 2003 to early 2007. Its objectives were to "estimate health risks that may be associated with hazardous compounds in heat-treated food, [and to] find cooking/processing methods that minimize the amounts of these compounds, thereby providing safe, nutritious, and high-quality food-stuffs." It found that "the evidence of acrylamide posing a cancer risk for humans has been strengthened," and that "compared with many regulated food carcinogens, the exposure to acrylamide poses a higher estimated risk to European consumers." HEATOX sought also to provide consumers with advice on how to lower their intake of acrylamide, specifically pointing out that home-cooked food tends to contribute far less to overall acrylamide levels than food that was industrially prepared, and that avoiding overcooking is one of the best ways to minimize exposure at home.
United States
Acrylamide is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.
Acrylamide is considered a potential occupational carcinogen by U.S. government agencies and classified as a Group 2A carcinogen by the IARC. The Occupational Safety and Health Administration and the National Institute for Occupational Safety and Health have set dermal occupational exposure limits at 0.03 mg/m3 over an eight-hour workday.