A recent trend at many eating establishments in Berkeley has been the introduction of compostable cutlery. How are these biodegradable plastics made? It turns out the key component is PLA: polylactic acid. How is polylactic acid produced? Wikipedia has the answer:
Bacterial fermentation is used to produce lactic acid from corn starch or cane sugar. However, lactic acid cannot be directly polymerized to a useful product, because each polymerization reaction generates one molecule of water, the presence of which degrades the forming polymer chain to the point that only very low molecular weights are observed. Instead, lactic acid is oligomerized and then catalytically dimerized to make the cyclic lactide monomer. Although dimerization also generates water, it can be separated prior to polymerization. PLA of high molecular weight is produced from the lactide monomer by ring-opening polymerization using most commonly a stannous octoate catalyst, but for laboratory demonstrations tin(II) chloride is often employed. This mechanism does not generate additional water, and hence, a wide range of molecular weights are accessible.
Polymerization of a racemic mixture of L- and D-lactides usually leads to the synthesis of poly-DL-lactide (PDLLA) which is not crystalline but amorphous. Use of stereospecific catalysts can lead to heterotactic PLA which has been found to show crystallinity. The degree of crystallinity, and hence many important properties, is controlled by the ratio of D to L enantiomers used.
Oh… the stannous octoate catalyst! That’s what I was missing. 🙂