Bio-Polyamides: Where Do They Come From?

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Bio-polyamides have been available commercially since the first half of the 20thCentury, when Rilsan®11 was first introduced. Since then, other partly or fully bio-sourced polyamides have been commercialized for a range of applications. This blog post explains how organic chemistry and catalysis can be critical to converting renewable raw materials into technologically valuable polymers.

Both 11-aminoundecanoic acid and sebacic acid are products from chemical conversion of ricinoleic acid, the major fatty acid component of castor oil.Castor oil is hydrolyzed to give ricinoleic acid and glycerol, which are separated. High temperature treatment of the methyl ester of ricinoleic acid produces 11-undecanelic acid and heptanal4. Bromination of the double bond of 11-undecalenic acid followed by reaction with ammonia gives 11-aminoundecanoic acid, the monomer used to make PA 11 (Rilsan® 11).

Sebacic acid is produced commercially by “fusing” ricinoleic acid with alkali (reacting at high temperature with sodium or potassium hydroxide). This chemistry has been known for decades and has been optimized significantly.

At present, there is no large-scale commercial source of bio-based 1,12-dodecanedioic acid, although potential routes have been reported. Polyamides produced from this monomer rely on 1,12-dodecanedioic acid prepared from petroleum-derived butadiene, so such polymers are only partially bio-sourced, assuming that the diamine component is derived from renewable sources.

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