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Concept
Polylactic acid
Summary
Polylactic acid, also known as poly(lactic acid) or polylactide (PLA), is a thermoplastic polyester with backbone formula (C3H4O2)n or [–C(CH3)HC(=O)O–]n, formally obtained by condensation of lactic acid C(CH3)(OH)HCOOH with loss of water (hence its name). It can also be prepared by ring-opening polymerization of lactide [–C(CH3)HC(=O)O–]2, the cyclic dimer of the basic repeating unit.
PLA has become a popular material due to it being economically produced from renewable resources. In 2021, PLA had the highest consumption volume of any bioplastic of the world, although it is still not a commodity polymer. Its widespread application has been hindered by numerous physical and processing shortcomings. PLA is the most widely used plastic filament material in FDM 3D printing. Its low melting point, high strength, low thermal expansion, and good layer adhesion, although it possesses poor heat resistance unless annealed.
Although the name "polylactic acid" is widely used, it does not comply with IUPAC standard nomenclature, which is "poly(lactic acid)". The name "polylactic acid" is potentially ambiguous or confusing, because PLA is not a polyacid (polyelectrolyte), but rather a polyester.
The monomer is typically made from fermented plant starch such as from corn, cassava, sugarcane or sugar beet pulp.
Several industrial routes afford usable (i.e. high molecular weight) PLA. Two main monomers are used: lactic acid, and the cyclic di-ester, lactide. The most common route to PLA is the ring-opening polymerization of lactide with various metal catalysts (typically tin octoate) in solution or as a suspension. The metal-catalyzed reaction tends to cause racemization of the PLA, reducing its stereoregularity compared to the starting material (usually corn starch).
The direct condensation of lactic acid monomers can also be used to produce PLA. This process needs to be carried out at less than 200 °C; above that temperature, the entropically favored lactide monomer is generated. This reaction generates one equivalent of water for every condensation (esterification) step.
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