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. 2020 Jun 17;59(24):11149-11156.
doi: 10.1021/acs.iecr.0c01122. Epub 2020 May 1.

Chemical Degradation of End-of-Life Poly(lactic acid) into Methyl Lactate by a Zn(II) Complex

Luis A Román-Ramírez  1 , Paul McKeown  2 , Chanak Shah  1 , Joshua Abraham  1 , Matthew D Jones  2 , Joseph Wood  1
Affiliations

Chemical Degradation of End-of-Life Poly(lactic acid) into Methyl Lactate by a Zn(II) Complex

Luis A Román-Ramírez et al. Ind Eng Chem Res. .

Abstract

The catalyzed methanolysis of end-of-life poly(lactic acid) (PLA) products by an ethylenediamine Zn(II) complex to form biodegradable methyl lactate was studied experimentally at 70, 90, and 110 °C. The PLA samples consisted of typical consumer waste materials, including a cup, a toy, and a three-dimensional (3D) printing material. High selectivities and yields (>94%) were possible depending on temperature and reaction time. Additionally, and to develop a predictive kinetic model, kinetic parameters (pre-exponential factor and activation energies) of the PLA transesterification reaction were first obtained from virgin PLA. These parameters were subsequently used to estimate the conversion of PLA, selectivity, and yield of methyl lactate after 1 and 4 h of the reaction, and the results were compared with the experimental values of the end-of-life PLA. Despite the presence of unknown additives in the PLA waste material and uncontrolled particle size, the model was able to predict the overall conversion, selectivity, and yield to an average deviation of 5, 7, and 12%, respectively. A greater agreement between the model and experimental values is observed for the higher temperatures and the longer reaction time. Larger deviations were observed for the PLA toy, which we attribute to the presence of additives, since despite its lower molecular weight, it possessed a higher structural strength.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Circular economy in the chemical recycling of poly(lactic acid) into methyl lactate.
Figure 2
Figure 2
PLA waste samples studied: (a) a cup, (b) toy, and (c) 3D printing material.
Figure 3
Figure 3
1H NMR spectrum (400 MHz, CDCl3) of the Zn(II) catalyst.
Figure 4
Figure 4
1H NMR spectrum (400 MHz, C6D6) of PLA toy degradation at 70 °C.
Figure 5
Figure 5
Reaction profiles at (a) 70 °C, (b) 90 °C, and (c) 110 °C. Symbols: experimental results; lines: modeling results using Arrhenius parameters from Table 2.
Figure 6
Figure 6
Parity plot of predicted vs experimental values for all data.
Figure 7
Figure 7
Poly(lactic acid) conversion experimental values at 1 and 4 h for the end-of-life samples tested at three different temperatures. Predicted (Pred.) values from the modeling. Error bars correspond to 1 standard deviation.
Figure 8
Figure 8
Methyl lactate selectivity experimental values at 1 and 4 h for the end-of-life samples tested at three different temperatures. Predicted (Pred.) values from the modeling. Error bars correspond to 1 standard deviation.
Figure 9
Figure 9
Methyl lactate yields experimental values at 1 and 4 h for the end-of-life samples tested at three different temperatures. Predicted (Pred.) values from the modeling. Error bars correspond to 1 standard deviation.
Figure 10
Figure 10
Dispersed (left) and sedimented (right) insoluble particles in a final sample of PLA toy depolymerized at 110 °C.
See this image and copyright information in PMC

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