C3H5NO

C3H5NO is the chemical formula for acrylamide, also known as 2-propenamide. It is a simple vinyl amide consisting of a vinyl group (CH2=CH–) attached to an amide (–CONH2). The molecule has a molecular weight of about 71.08 g/mol and is a colorless, crystalline solid at room temperature that is soluble in water and many organic solvents. Its reactivity is dominated by the terminal vinyl bond, which makes acrylamide a versatile monomer for polymerization. The common SMILES representation is C=CC(=O)N.

Industrial production and occurrence

Acrylamide is produced on a large scale primarily by hydrolysis of acrylonitrile, which itself is derived from propylene via ammoxidation. The hydrolysis step converts the nitrile group to the amide, yielding acrylamide. In addition to industrial applications, acrylamide can form in carbohydrate-rich foods during high-temperature cooking processes such as frying, baking, or roasting, through the Maillard and related reactions. This incidental formation has prompted regulatory and health risk assessments.

Applications and uses

The principal use of acrylamide is as a monomer for producing polyacrylamide polymers. These polymers have widespread applications in water and wastewater treatment as flocculants, in papermaking, in petroleum industry, and as thickening or gelling agents. Polyacrylamide gels are also fundamental in laboratory electrophoresis and some chromatography techniques. The acrylamide monomer itself is handled with care to prevent unwanted polymerization and exposure.

Safety and regulations

Acrylamide is classified as potentially carcinogenic to humans (IARC Group 2A) and is a neurotoxin in animals, with safety measures emphasizing proper handling, containment, and control of residual monomer in polymer products. Food-related concerns focus on its formation during high-temperature cooking, prompting regulatory guidance on allowable levels and mitigation strategies.