What is Acrylamide? - Definition, Uses & Structure

Instructor: Laura Foist

Laura has a Masters of Science in Food Science and Human Nutrition and has taught college Science.

In this lesson we will learn about acrylamide and polyacrylamide and the application of these chemicals. We will cover in what instances acrylamide is toxic, and how it is used without toxicity.

Acrylamide and Polyacrylamide

How does water go from waste water to being clean enough to put back into the river? There are several steps involved in purifying water. One of these steps is called flocculation, which often uses polyacrylamide. Polyacrylamide is also used for paper processing, oil processing, and in gel electrophoresis. But what is acrylamide and what is polyacrylamide?

Acrylamide can be extremely dangerous if not handled properly: it can act as a nerve toxin, lead to birth defects, and lead to cancer. But when it is polymerized into polyacrylamide, which is a chain of acrylamide molecules, it is no longer toxic. Acrylamide as a pure chemical doesn't have any uses, other than being turned into its non-toxic form, polyacrylamide. Although, it is still possible for polyacrylamide to break down into acrylamide.

Acrylamide can polymerize, making it non-toxic
Polymer structure

Structure

Acrylamide has the chemical formula of C3H5NO, and its IUPAC (formal) name is prop-2-enamide. From the name prop-2-enamide, we can see that it is a 3-carbon structure (prop), with a double bond starting at carbon 2 (en), and the starting functional group on carbon 1 is an amide. An amide is a carbon attached with a double bond to oxygen and attached to a NH2. Acrylamide is a white crystalline solid. It has no scent and is soluble in water.

Acrylamide has 3 carbon atoms, with an alkene between carbons 2 and 3, an amide, and a carbon-oxygen double bond
Acrylamide structure

The double bond and carbon-oxygen bond are able to share electrons through resonance. So another resonance structure would have a positive charge on carbon 3, a double bond at carbon 1, and a negative charge on the oxygen. So it could potentially react at carbon 3 (with the positive charge there), the oxygen (with the negative charge there), or carbon 1.

Acrylamide can resonate to give carbon 3 a positive charge and the oxygen a negative charge
Resonance structure

When acrylamide becomes polyacrylamide, this means that acrylamide molecules form together in a chain through polymerization.

Polyacrylamide Uses

The most common use of polyacrylamide is in flocculation for water treatment. Flocculation is the process of clumping organic matter together so that it can be filtered out of the water. Once the organic matter has been clumped together, the polyacrylamide filters them out.

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