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Understanding N-Isopropylacrylamide And Some Of The Unique Chemical Properties

By: Chad DeBolt

While there are many specialty monomers used in industrial applications, there are very few with the unique properties that can be imparted by n-isopropylacrylamide. Some pertinent information for isopropylacrylamide:

Alternate names 2-methylidene-N-propan-2-ylpentanamide; N-isopropyl-2-propyl-acrylamide; N-isopropyl-2-methylene-pentanoic acid amide
CAS 2210-25-5
Molecular weight 155.24 g/mol
Formula C9H17NO

As with many acrylamide molecules there are some standard synthetic methods available to make it. The most commonly utilized method is outlined in this academic article [Tetrahedron Letters, 30, p. 3837, 1989]. In this synthesis an acrylonitrile is oxidized using isopropanol, yielding the expected isopropylacrylamide. Yields for this reaction are not particularly good, typically around 65-70% when undertaken by a competent organic bench-chemist. However, the yields can be improved by using acrylonitriles and alcohols that have undergone purification immediately prior to reaction. If the purification is utilized in addition to clean, dry glassware a good chemist can realize yields in excess of 75%.

It is worth noting that several safety steps should be taken when synthesizing this molecule since the reagents used are particularly toxic and/or dangerous. Additionally, the final material is potentially fatal in high doses.

As an individual compound, isopropylacrylamide doesn't have a lot of direct application or use. The most notable application use of this acrylamide is in a polymeric form. By reacting isopropylacrylamide in the presence of a radical initiator (e.g., AIBN) and the correct thermal parameter a poly(isopropylacrylamide) can be formed. This polymer is sometimes referred to as Poly(NiPAM). An article that discusses some of this work is Meunier, F., Elaissari, A. Surf. Sci. Ser. 115, 117, (2003).

The most important and technically interesting property of poly(isopropylacrylamide) is its thermosensitivity. Poly(NiPAM) is a material that has a reversible phase change at around 35-40 Celsius, which means that below that temperature the material has very different physical properties when compared to a higher temperature environment. This means the material is effective in applications where a 'thermal switch' is required. As an example, consider the need for a material that can be used for a pharmaceutical gel capsule which only releases the contents above 35 Celsius (i.e., inside the body). The gel cap could theoretically be made from poly(isopropylacrylamide) so that when stored in ambient conditions the pharmaceutical is protected, but once taken internally, the material changes and its porosity changes enough to release the drug into the system.

A deeper discussion of the thermosensitivty and subsequent uses of poly(NiPAM) is beyond this article. However, the continuous, ardent research of the monomeric isopropylacrylamide and its copolymers is a testament to the potential for this molecule.

Article Source: http://www.newarticledaily.com

If you would like to learn more about n-isopropylacrylamide visit www.monomerpolymer.com.

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