The Chemical Recycling of PLA: A Review
Abstract
:1. Introduction
2. PLA Hydrolysis—To Lactic Acid
3. Alcoholysis—To Alkyl Lactates
4. To Other Products
5. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
- Geyer, R.; Jambeck, J.R.; Law, K.L. Production, use, and fate of all plastics ever made. Sci. Adv. 2017, 3, e1700782. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Shafiee, S.; Topal, E. When will fossil fuel reserves be diminished? Energy Policy 2009, 37, 181–189. [Google Scholar] [CrossRef]
- Lebreton, L.; Andrady, A. Future scenarios of global plastic waste generation and disposal. Palgrave Commun. 2019, 5, 1–11. [Google Scholar] [CrossRef] [Green Version]
- Bonanno, G.; Orlando-Bonaca, M. Ten inconvenient questions about plastics in the sea. Environ. Sci. Policy 2018, 85, 146–154. [Google Scholar] [CrossRef]
- Jambeck, J.R.; Geyer, R.; Wilcox, C.; Siegler, T.R.; Perryman, M.; Andrady, A.; Narayan, R.; Law, K.L. Plastic waste inputs from land into the ocean. Science (80-.) 2015, 347, 768–771. [Google Scholar] [CrossRef]
- Lebreton, L.; Slat, B.; Ferrari, F.; Sainte-Rose, B.; Aitken, J.; Marthouse, R.; Hajbane, S.; Cunsolo, S.; Schwarz, A.; Levivier, A.; et al. Evidence that the Great Pacific Garbage Patch is rapidly accumulating plastic. Sci. Rep. 2018, 8, 1–15. [Google Scholar] [CrossRef] [Green Version]
- Andrady, A.L.; Neal, M.A. Applications and societal benefits of plastics. Philos. Trans. R. Soc. B Biol. Sci. 2009, 364, 1977–1984. [Google Scholar] [CrossRef]
- Thompson, R.C.; Swan, S.H.; Moore, C.J.; Vom Saal, F.S. Our plastic age. Philos. Trans. R. Soc. B Biol. Sci. 2009, 364, 1973–1976. [Google Scholar] [CrossRef] [Green Version]
- Millet, H.; Vangheluwe, P.; Block, C.; Sevenster, A.; Garcia, L.; Antonopoulos, R. The Nature of Plastics and Their Societal Usage. In Plastics and the Environment; The Royal Society of Chemistry: London, UK, 2019; pp. 1–20. [Google Scholar] [CrossRef]
- Payne, J.; McKeown, P.; Jones, M.D. A circular economy approach to plastic waste. Polym. Degrad. Stab. 2019, 165, 170–181. [Google Scholar] [CrossRef]
- Hopewell, J.; Dvorak, R.; Kosior, E. Plastics recycling: Challenges and opportunities. Philos. Trans. R. Soc. B Biol. Sci. 2009, 364, 2115–2126. [Google Scholar] [CrossRef] [Green Version]
- Kaur, G.; Uisan, K.; Ong, K.L.; Ki Lin, C.S. Recent Trends in Green and Sustainable Chemistry & Waste Valorisation: Rethinking Plastics in a circular economy. Curr. Opin. Green Sustain. Chem. 2018, 9, 30–39. [Google Scholar] [CrossRef]
- Huysman, S.; De Schaepmeester, J.; Ragaert, K.; Dewulf, J.; De Meester, S. Performance indicators for a circular economy: A case study on post-industrial plastic waste. Resour. Conserv. Recycl. 2017, 120, 46–54. [Google Scholar] [CrossRef]
- Abdel-Rahman, M.A.; Tashiro, Y.; Sonomoto, K. Recent advances in lactic acid production by microbial fermentation processes. Biotechnol. Adv. 2013, 31, 877–902. [Google Scholar] [CrossRef] [PubMed]
- Abdel-Rahman, M.A.; Tashiro, Y.; Sonomoto, K. Lactic acid production from lignocellulose-derived sugars using lactic acid bacteria: Overview and limits. J. Biotechnol. 2011, 156, 286–301. [Google Scholar] [CrossRef] [PubMed]
- VanWouwe, P.; Dusselier, M.; Vanleeuw, E.; Sels, B. Lactide Synthesis and Chirality Control for Polylactic acid Production. ChemSusChem 2016, 9, 907–921. [Google Scholar] [CrossRef] [PubMed]
- Shen, L.; Haufe, J.; Patel, M.K. Product Overview and Market Projection of Emerging Bio-Based Plastics; Utrecht University: Utrecht, The Netherlands, 2009; p. 74. [Google Scholar]
- De Clercq, R.; Dusselier, M.; Poleunis, C.; Debecker, D.P.; Giebeler, L.; Oswald, S.; Makshina, E.; Sels, B.F. Titania-Silica Catalysts for Lactide Production from Renewable Alkyl Lactates: Structure–Activity Relations. ACS Catal. 2018, 8, 8130–8139. [Google Scholar] [CrossRef]
- Ghadamyari, M.; Chaemchuen, S.; Zhou, K.; Dusselier, M.; Sels, B.F.; Mousavi, B.; Verpoort, F. One-step synthesis of stereo-pure l, l lactide from l -lactic acid. Catal. Commun. 2018, 114, 33–36. [Google Scholar] [CrossRef]
- Dusselier, M.; Van Wouwe, P.; Dewaele, A.; Jacobs, P.A.; Sels, B.F. Shape-selective zeolite catalysis for bioplastics production. Science (80-.) 2015, 349, 78–80. [Google Scholar] [CrossRef] [Green Version]
- De Clercq, R.; Dusselier, M.; Makshina, E.; Sels, B.F. Catalytic Gas-Phase Production of Lactide from Renewable Alkyl Lactates. Angew. Chem. Int. Ed. 2018, 57, 3074–3078. [Google Scholar] [CrossRef]
- Upare, P.P.; Hwang, Y.K.; Chang, J.-S.; Hwang, D.W. Synthesis of Lactide from Alkyl Lactate via a Prepolymer Route. Ind. Eng. Chem. Res. 2012, 51, 4837–4842. [Google Scholar] [CrossRef]
- Upare, P.P.; Yoon, J.W.; Hwang, D.W.; Lee, U.H.; Hwang, Y.K.; Hong, D.Y.; Kim, J.C.; Lee, J.H.; Kwak, S.K.; Shin, H.; et al. Design of a heterogeneous catalytic process for the continuous and direct synthesis of lactide from lactic acid. Green Chem. 2016, 18, 5978–5983. [Google Scholar] [CrossRef]
- Heo, S.; Park, H.W.; Lee, J.H.; Chang, Y.K. Design and Evaluation of Sustainable Lactide Production Process with an One-Step Gas Phase Synthesis Route. ACS Sustain. Chem. Eng. 2019, 7, 6178–6184. [Google Scholar] [CrossRef]
- Thomas, C.M. Stereocontrolled ring-opening polymerization of cyclic esters: synthesis of new polyester microstructures. Chem. Soc. Rev. 2010, 39, 165–173. [Google Scholar] [CrossRef] [PubMed]
- Platel, R.H.; Hodgson, L.M.; Williams, C.K. Biocompatible Initiators for Lactide Polymerization. Polym. Rev. 2008, 48, 11–63. [Google Scholar] [CrossRef]
- Dechy-Cabaret, O.; Martin-Vaca, B.; Bourissou, D. FeA Controlled Ring-Opening Polymerization of Lactide and Glycolide. Chem. Rev. 2004, 104, 6147–6176. [Google Scholar] [CrossRef] [PubMed]
- Stanford, M.J.; Dove, A.P. Stereocontrolled ring-opening polymerisation of lactide. Chem. Soc. Rev. 2010, 39, 486–494. [Google Scholar] [CrossRef]
- Rabnawaz, M.; Wyman, I.; Auras, R.; Cheng, S. A roadmap towards green packaging: the current status and future outlook for polyesters in the packaging industry. Green Chem. 2017, 19, 4737–4753. [Google Scholar] [CrossRef]
- Auras, R.; Harte, B.; Selke, S. An overview of polylactides as packaging materials. Macromol. Biosci. 2004, 4, 835–864. [Google Scholar] [CrossRef]
- Ahmed, J.; Varshney, S.K. Polylactides-chemistry, properties and green packaging technology: A review. Int. J. Food Prop. 2011, 14, 37–58. [Google Scholar] [CrossRef]
- Viera, J.S.C.; Marques, M.R.C.; Nazareth, M.C.; Jimenez, P.C.; Castro, Í.B. On replacing single-use plastic with so-called biodegradable ones: The case with straws. Environ. Sci. Policy 2020, 106, 177–181. [Google Scholar] [CrossRef]
- Rocca-Smith, J.R.; Whyte, O.; Brachais, C.H.; Champion, D.; Piasente, F.; Marcuzzo, E.; Sensidoni, A.; Debeaufort, F.; Karbowiak, T. Beyond Biodegradability of Poly(lactic acid): Physical and Chemical Stability in Humid Environments. ACS Sustain. Chem. Eng. 2017, 5, 2751–2762. [Google Scholar] [CrossRef]
- Pawar, R.P.; Tekale, S.U.; Shisodia, S.U.; Totre, J.T.; Domb, A.J. Biomedical Applications of Poly(Lactic Acid). Rec. Pat. Regen. Med. 2014, 4, 40–51. [Google Scholar] [CrossRef]
- Lasprilla, A.J.R.; Martinez, G.A.R.; Lunelli, B.H.; Jardini, A.L.; Filho, R.M. Poly-lactic acid synthesis for application in biomedical devices - a review. Biotechnol. Adv. 2012, 30, 321–328. [Google Scholar] [CrossRef] [PubMed]
- Singhvi, M.S.; Zinjarde, S.S.; Gokhale, D.V. Polylactic acid: synthesis and biomedical applications. J. Appl. Microbiol. 2019, 127, 1612–1626. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Ghalia, M.A.; Dahman, Y. Biodegradable poly(lactic acid)-based scaffolds: synthesis and biomedical applications. J. Polym. Res. 2017, 24. [Google Scholar] [CrossRef]
- Nampoothiri, K.M.; Nair, N.J.; John, R.P. An overview of the recent developments in polylactide (PLA) research. Bioresour. Technol. 2010, 101, 8493–8501. [Google Scholar] [CrossRef] [PubMed]
- Castro-Aguirre, E.; Iñiguez-Franco, F.; Samsudin, H.; Fang, X.; Auras, R. Poly(lactic acid)-Mass production, processing, industrial applications, and end of life. Adv. Drug Deliv. Rev. 2016, 107, 333–366. [Google Scholar] [CrossRef] [Green Version]
- Vink, E.T.H.; Davies, S. Life Cycle Inventory and Impact Assessment Data for 2014 IngeoTM Polylactide Production. Ind. Biotechnol. 2015, 11, 167–180. [Google Scholar] [CrossRef] [Green Version]
- Gu, W.; Xu, P.; Wang, Y.; Yao, Y.; Yuan, D.; Shen, Q. Synthesis and Characterization of Yttrium and Ytterbium Complexes Supported by Salen Ligands and Their Catalytic Properties for rac-Lactide Polymerization. Organometallics 2015, 34, 2907–2916. [Google Scholar] [CrossRef]
- Shen, L.; Worrell, E.; Patel, M. Present and future development in plastics from biomass. Biofuels Bioprod. Biorefining 2010, 4, 25–40. [Google Scholar] [CrossRef]
- Haider, T.P.; Völker, C.; Kramm, J.; Landfester, K.; Wurm, F.R. Plastics of the Future? The Impact of Biodegradable Polymers on the Environment and on Society. Angew. Chem. Int. Ed. 2019, 58, 50–62. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Ho, K.L.G.; Pometto, A.L.; Hinz, P.N.; Gadea-Rivas, A.; Briceño, J.A.; Rojas, A. Field exposure study of polylactic acid (PLA) plastic films in the banana fields of Costa Rica. J. Environ. Polym. Degrad. 1999, 7, 167–172. [Google Scholar] [CrossRef]
- Rudnik, E.; Briassoulis, D. Degradation behaviour of poly(lactic acid) films and fibres in soil under Mediterranean field conditions and laboratory simulations testing. Ind. Crops Prod. 2011, 33, 648–658. [Google Scholar] [CrossRef]
- Bagheri, A.R.; Laforsch, C.; Greiner, A.; Agarwal, S. Fate of So-Called Biodegradable Polymers in Seawater and Freshwater. Glob. Chall. 2017, 1, 1700048. [Google Scholar] [CrossRef]
- Tsuji, H.; Suzuyoshi, K. Environmental degradation of biodegradable polyesters 1. Poly(ε-caprolactone), poly[(R)-3-hydroxybutyrate], and poly(L-lactide) films in controlled static seawater. Polym. Degrad. Stab. 2002, 75, 347–355. [Google Scholar] [CrossRef]
- Nazareth, M.; Marques, M.R.C.; Leite, M.C.A.; Castro, Í.B. Commercial plastics claiming biodegradable status: Is this also accurate for marine environments? J. Hazard. Mater. 2019, 366, 714–722. [Google Scholar] [CrossRef]
- Tsuji, H.; Suzuyoshi, K. Environmental degradation of biodegradable polyesters 2. Poly(ε-caprolactone), poly[(R)-3-hydroxybutyrate], and poly(L-lactide) films in natural dynamic seawater. Polym. Degrad. Stab. 2002, 75, 357–365. [Google Scholar] [CrossRef]
- Kolstad, J.J.; Vink, E.T.H.; De Wilde, B.; Debeer, L. Assessment of anaerobic degradation of IngeoTM polylactides under accelerated landfill conditions. Polym. Degrad. Stab. 2012, 97, 1131–1141. [Google Scholar] [CrossRef]
- Alaerts, L.; Augustinus, M.; Van Acker, K. Impact of bio-based plastics on current recycling of plastics. Sustainability 2018, 10, 1487. [Google Scholar] [CrossRef] [Green Version]
- La Mantia, F.P.; Botta, L.; Morreale, M.; Scaffaro, R. Effect of small amounts of poly(lactic acid) on the recycling of poly(ethylene terephthalate) bottles. Polym. Degrad. Stab. 2012, 97, 21–24. [Google Scholar] [CrossRef]
- Cornell, D.D. Biopolymers in the existing postconsumer plastics recycling stream. J. Polym. Environ. 2007, 15, 295–299. [Google Scholar] [CrossRef]
- Ulrici, A.; Serranti, S.; Ferrari, C.; Cesare, D.; Foca, G.; Bonifazi, G. Efficient chemometric strategies for PET-PLA discrimination in recycling plants using hyperspectral imaging. Chemom. Intell. Lab. Syst. 2013, 122, 31–39. [Google Scholar] [CrossRef]
- Danyluk, C.; Erickson, R.; Burrows, S.; Auras, R. Industrial Composting of Poly(Lactic Acid) Bottles. J. Test. Eval. 2010, 38, 717–723. [Google Scholar] [CrossRef]
- Kale, G.; Auras, R.; Singh, S.P.; Narayan, R. Biodegradability of polylactide bottles in real and simulated composting conditions. Polym. Test. 2007, 26, 1049–1061. [Google Scholar] [CrossRef]
- Ahn, H.K.; Huda, M.S.; Smith, M.C.; Mulbry, W.; Schmidt, W.F.; Reeves, J.B. Biodegradability of injection molded bioplastic pots containing polylactic acid and poultry feather fiber. Bioresour. Technol. 2011, 102, 4930–4933. [Google Scholar] [CrossRef]
- Emadian, S.M.; Onay, T.T.; Demirel, B. Biodegradation of bioplastics in natural environments. Waste Manag. 2017, 59, 526–536. [Google Scholar] [CrossRef]
- Kale, G.; Kijchavengkul, T.; Auras, R.; Rubino, M.; Selke, S.E.; Singh, S.P. Compostability of bioplastic packaging materials: An overview. Macromol. Biosci. 2007, 7, 255–277. [Google Scholar] [CrossRef]
- Pillin, I.; Montrelay, N.; Bourmaud, A.; Grohens, Y. Effect of thermo-mechanical cycles on the physico-chemical properties of poly(lactic acid). Polym. Degrad. Stab. 2008, 93, 321–328. [Google Scholar] [CrossRef]
- Badia, J.D.; Ribes-Greus, A. Mechanical recycling of polylactide, upgrading trends and combination of valorization techniques. Eur. Polym. J. 2016, 84, 22–39. [Google Scholar] [CrossRef] [Green Version]
- Beltrán, F.R.; Lorenzo, V.; Acosta, J.; de la Orden, M.U.; Martínez Urreaga, J. Effect of simulated mechanical recycling processes on the structure and properties of poly(lactic acid). J. Environ. Manag. 2018, 216, 25–31. [Google Scholar] [CrossRef] [Green Version]
- Zhao, P.; Rao, C.; Gu, F.; Sharmin, N.; Fu, J. Close-looped recycling of polylactic acid used in 3D printing: An experimental investigation and life cycle assessment. J. Clean. Prod. 2018, 197, 1046–1055. [Google Scholar] [CrossRef]
- Hong, M.; Chen, E.Y.X. Chemically recyclable polymers: A circular economy approach to sustainability. Green Chem. 2017, 19, 3692–3706. [Google Scholar] [CrossRef]
- Piemonte, V.; Sabatini, S.; Gironi, F. Chemical Recycling of PLA: A Great Opportunity Towards the Sustainable Development? J. Polym. Environ. 2013, 21, 640–647. [Google Scholar] [CrossRef]
- Von Burkersroda, F.; Schedl, L.; Göpferich, A. Why degradable polymers undergo surface erosion or bulk erosion. Biomaterials 2002, 23, 4221–4231. [Google Scholar] [CrossRef]
- Dusselier, M.; Van Wouwe, P.; Dewaele, A.; Makshina, E.; Sels, B.F. Lactic acid as a platform chemical in the biobased economy: The role of chemocatalysis. Energy Environ. Sci. 2013, 6, 1415–1442. [Google Scholar] [CrossRef]
- Gironi, F.; Frattari, S.; Piemonte, V. PLA Chemical Recycling Process Optimization: PLA Solubilization in Organic Solvents. J. Polym. Environ. 2016, 24, 328–333. [Google Scholar] [CrossRef]
- Tsuji, H.; Daimon, H.; Fujie, K. A new strategy for recycling and preparation of poly(L-lactic acid): hydrolysis in the melt. Biomacromolecules 2003, 4, 835–840. [Google Scholar] [CrossRef]
- Tsuji, H.; Saeki, T.; Tsukegi, T.; Daimon, H.; Fujie, K. Comparative study on hydrolytic degradation and monomer recovery of poly(l-lactic acid) in the solid and in the melt. Polym. Degrad. Stab. 2008, 93, 1956–1963. [Google Scholar] [CrossRef]
- Tsuji, H.; Ogiwara, M.; Saha, S.K.; Sakaki, T. Enzymatic, alkaline, and autocatalytic degradation of poly(L-lactic acid): Effects of biaxial orientation. Biomacromolecules 2006, 7, 380–387. [Google Scholar] [CrossRef]
- Rahaman, M.H.; Tsuji, H. Hydrolytic degradation behavior of stereo multiblock and diblock poly(lactic acid)s: Effects of block lengths. Polym. Degrad. Stab. 2013, 98, 709–719. [Google Scholar] [CrossRef]
- Tsuji, H. Poly(lactide) Stereocomplexes: Formation, Structure, Properties, Degradation, and Applications. Macromol. Biosci. 2005, 5, 569–597. [Google Scholar] [CrossRef] [PubMed]
- Tsuji, H.; Ikada, Y. Blends of crystalline and amorphous poly(lactide). III. Hydrolysis of solution-cast blend films. J. Appl. Polym. Sci. 1997, 63, 855–863. [Google Scholar] [CrossRef]
- Tsuji, H. Hydrolytic Degradation. In Poly(Lactic Acid); John Wiley & Sons, Inc.: Hoboken, NJ, USA, 2010; pp. 343–381. [Google Scholar] [CrossRef]
- Hirao, K.; Shimamoto, Y.; Nakatsuchi, Y.; Ohara, H. Hydrolysis of poly(l-lactic acid) using microwave irradiation. Polym. Degrad. Stab. 2010, 95, 86–88. [Google Scholar] [CrossRef]
- Mohd-Adnan, A.-F.; Nishida, H.; Shirai, Y. Evaluation of kinetics parameters for poly(l-lactic acid) hydrolysis under high-pressure steam. Polym. Degrad. Stab. 2008, 93, 1053–1058. [Google Scholar] [CrossRef]
- Piemonte, V.; Gironi, F. Kinetics of Hydrolytic Degradation of PLA. J. Polym. Environ. 2013, 21, 313–318. [Google Scholar] [CrossRef]
- Piemonte, V.; Gironi, F. Lactic Acid Production by Hydrolysis of Poly(Lactic Acid) in Aqueous Solutions: An Experimental and Kinetic Study. J. Polym. Environ. 2013, 21, 275–279. [Google Scholar] [CrossRef]
- Siparsky, G.L.; Voorhees, K.J.; Miao, F. Hydrolysis of polylactic acid (PLA) and polycaprolactone (PCL) in aqueous acetonitrile solutions: Autocatalysis. J. Environ. Polym. Degrad. 1998, 6, 31–41. [Google Scholar] [CrossRef]
- Annesini Maria, C.; Frattari, S.; Gironi, F.; Piemonte, V.; Sabia, R.; Villani, C. Degradation of Post-consumer PLA: Hydrolysis of Polymeric Matrix and Oligomers Stabilization in Aqueous Phase. J. Polym. Environ. 2018, 26, 4396–4404. [Google Scholar] [CrossRef]
- Iñiguez-Franco, F.; Auras, R.; Dolan, K.; Selke, S.; Holmes, D.; Rubino, M.; Soto-Valdez, H. Chemical recycling of poly(lactic acid) by water-ethanol solutions. Polym. Degrad. Stab. 2018, 149, 28–38. [Google Scholar] [CrossRef]
- Auras, R.; Burgess, G.; Holmes, D.; Fang, X.; Rubino, M.; Soto-valdez, H. Concurrent solvent induced crystallization and hydrolytic degradation of PLA by water-ethanol solutions. Polymer 2016, 99, 315–323. [Google Scholar] [CrossRef] [Green Version]
- Lazzari, S.; Codari, F.; Storti, G.; Morbidelli, M.; Moscatelli, D. Modeling the pH-dependent PLA oligomer degradation kinetics. Polym. Degrad. Stab. 2014, 110, 80–90. [Google Scholar] [CrossRef]
- Jung, J.H.; Ree, M.; Kim, H. Acid- and base-catalyzed hydrolyses of aliphatic polycarbonates and polyesters. Catal. Today 2006, 115, 283–287. [Google Scholar] [CrossRef]
- De Jong, S.J.; Arias, E.R.; Rijkers, D.T.S.; Nostrum, C.F. Van New insights into the hydrolytic degradation of poly (lactic acid): participation of the alcohol terminus. Polymer 2001, 42, 2795–2802. [Google Scholar] [CrossRef]
- Shih, C. Chain-end scission in acid catalyzed hydrolysis of poly (d,l-lactide) in solution. J. Control. Release 1995, 34, 9–15. [Google Scholar] [CrossRef]
- Codari, F.; Lazzari, S.; Soos, M.; Storti, G.; Morbidelli, M.; Moscatelli, D. Kinetics of the hydrolytic degradation of poly(lactic acid). Polym. Degrad. Stab. 2012, 97, 2460–2466. [Google Scholar] [CrossRef]
- Van Nostrum, C.F.; Veldhuis, T.F.J.; Bos, G.W.; Hennink, W.E. Hydrolytic degradation of oligo(lactic acid): A kinetic and mechanistic study. Polymer 2004, 45, 6779–6787. [Google Scholar] [CrossRef]
- Lyu, S.P.; Schley, J.; Loy, B.; Lind, D.; Hobot, C.; Sparer, R.; Untereker, D. Kinetics and time-temperature equivalence of polymer degradation. Biomacromolecules 2007, 8, 2301–2310. [Google Scholar] [CrossRef]
- Rodriguez, E.J.; Marcos, B.; Huneault, M.A. Hydrolysis of polylactide in aqueous media. J. Appl. Polym. Sci. 2016, 133, 1–11. [Google Scholar] [CrossRef]
- Song, X.; Wang, H.; Yang, X.; Liu, F.; Yu, S.; Liu, S. Hydrolysis of poly(lactic acid) into calcium lactate using ionic liquid [Bmim][OAc] for chemical recycling. Polym. Degrad. Stab. 2014, 110, 65–70. [Google Scholar] [CrossRef]
- Al-Sabagh, A.M.; Yehia, F.Z.; Eissa, A.M.M.F.; Moustafa, M.E.; Eshaq, G.; Rabie, A.R.M.; Elmetwally, A.E. Glycolysis of poly(ethylene terephthalate) catalyzed by the Lewis base ionic liquid [Bmim][OAc]. Ind. Eng. Chem. Res. 2014, 53, 18443–18451. [Google Scholar] [CrossRef]
- Niaounakis, M. Recycling of biopolymers—The patent perspective. Eur. Polym. J. 2019, 114, 464–475. [Google Scholar] [CrossRef]
- Medina-Gonzalez, Y.; Aimar, P.; Lahitte, J.F.; Remigy, J.C. Towards green membranes: Preparation of cellulose acetate ultrafiltration membranes using methyl lactate as a biosolvent. Int. J. Sustain. Eng. 2011, 4, 75–83. [Google Scholar] [CrossRef] [Green Version]
- Rasool, M.A.; Van Goethem, C.; Vankelecom, I.F.J. Green preparation process using methyl lactate for cellulose-acetate-based nanofiltration membranes. Sep. Purif. Technol. 2020, 232, 115903. [Google Scholar] [CrossRef]
- Aparicio, S. Computational study on the properties and structure of methyl lactate. J. Phys. Chem. A 2007, 111, 4671–4683. [Google Scholar] [CrossRef]
- Planer, S.; Jana, A.; Grela, K. Ethyl Lactate: A Green Solvent for Olefin Metathesis. ChemSusChem 2019, 12, 4655–4661. [Google Scholar] [CrossRef]
- Pereira, C.S.M.; Silva, V.M.T.M.; Rodrigues, A.E. Ethyl lactate as a solvent: Properties, applications and production processes—A review. Green Chem. 2011, 13, 2658–2671. [Google Scholar] [CrossRef]
- Aparicio, S.; Alcalde, R. The green solvent ethyl lactate: An experimental and theoretical characterization. Green Chem. 2009, 11, 65–78. [Google Scholar] [CrossRef]
- Bowmer, C.T.; Hooftman, R.N.; Hanstveit, A.O.; Venderbosch, P.W.M.; van der Hoeven, N. The ecotoxicity and the biodegradability of lactic acid, alkyl lactate esters and lactate salts. Chemosphere 1998, 37, 1317–1333. [Google Scholar] [CrossRef]
- Filachione, E.M.; Lengel, J.H.; Fisher, C.H. Preparation of Methyl Lactate. Ind. Eng. Chem. 1945, 37, 388–390. [Google Scholar] [CrossRef]
- Hirao, K.; Nakatsuchi, Y.; Ohara, H. Alcoholysis of Poly(l-lactic acid) under microwave irradiation. Polym. Degrad. Stab. 2010, 95, 925–928. [Google Scholar] [CrossRef]
- Carné Sánchez, A.; Collinson, S.R. The selective recycling of mixed plastic waste of polylactic acid and polyethylene terephthalate by control of process conditions. Eur. Polym. J. 2011, 47, 1970–1976. [Google Scholar] [CrossRef] [Green Version]
- Liu, H.; Song, X.; Liu, F.; Liu, S.; Yu, S. Ferric chloride as an efficient and reusable catalyst for methanolysis of poly(lactic acid) waste. J. Polym. Res. 2015, 22, 135. [Google Scholar] [CrossRef]
- Petrus, R.; Bykowski, D.; Sobota, P. Solvothermal Alcoholysis Routes for Recycling Polylactide Waste as Lactic Acid Esters. ACS Catal. 2016, 6, 5222–5235. [Google Scholar] [CrossRef]
- Hofmann, M.; Alberti, C.; Scheliga, F.; Meißner, R.R.R.; Enthaler, S. Tin(ii) 2-ethylhexanoate catalysed methanolysis of end-of-life poly(lactide). Polym. Chem. 2020, 1–5. [Google Scholar] [CrossRef]
- Plichta, A.; Lisowska, P.; Kundys, A.; Zychewicz, A.; Dębowski, M.; Florjańczyk, Z. Chemical recycling of poly(lactic acid) via controlled degradation with protic (macro)molecules. Polym. Degrad. Stab. 2014, 108, 288–296. [Google Scholar] [CrossRef]
- Alberti, C.; Damps, N.; Meißner, R.R.R.; Hofmann, M.; Rijono, D.; Enthaler, S. Selective Degradation of End-of-Life Poly(lactide) via Alkali-Metal-Halide Catalysis. Adv. Sustain. Syst. 2020, 4. [Google Scholar] [CrossRef]
- Song, X.; Zhang, X.; Wang, H.; Liu, F.; Yu, S.; Liu, S. Methanolysis of poly(lactic acid) (PLA) catalyzed by ionic liquids. Polym. Degrad. Stab. 2013, 98, 2760–2764. [Google Scholar] [CrossRef]
- Song, X.; Bian, Z.; Hui, Y.; Wang, H.; Liu, F.; Yu, S. Zn-Acetate-Containing ionic liquid as highly active catalyst for fast and mild methanolysis of Poly(lactic acid). Polym. Degrad. Stab. 2019, 168, 108937. [Google Scholar] [CrossRef]
- Liu, H.; Zhao, R.; Song, X.; Liu, F.; Yu, S.; Liu, S.; Ge, X. Lewis Acidic Ionic Liquid [Bmim]FeCl4 as a High Efficient Catalyst for Methanolysis of Poly (lactic acid). Catal. Lett. 2017, 147, 2298–2305. [Google Scholar] [CrossRef]
- Jehanno, C.; Pérez-Madrigal, M.M.; Demarteau, J.; Sardon, H.; Dove, A.P. Organocatalysis for depolymerisation. Polym. Chem. 2019, 10, 172–186. [Google Scholar] [CrossRef] [Green Version]
- Nederberg, F.; Connor, E.F.; Glausser, T.; Hedrick, J.L. Organocatalytic chain scission of poly(lactides): A general route to controlled molecular weight, functionality and macromolecular architecture. Chem. Commun. 2001, 2066–2067. [Google Scholar] [CrossRef] [PubMed]
- Alberti, C.; Damps, N.; Meißner, R.R.R.; Enthaler, S. Depolymerization of End-of-Life Poly(lactide) via 4-Dimethylaminopyridine-Catalyzed Methanolysis. ChemistrySelect 2019, 4, 6845–6848. [Google Scholar] [CrossRef]
- Liu, F.; Guo, J.; Zhao, P.; Gu, Y.; Gao, J.; Liu, M. Facile synthesis of DBU-based protic ionic liquid for efficient alcoholysis of waste poly(lactic acid) to lactate esters. Polym. Degrad. Stab. 2019, 167, 124–129. [Google Scholar] [CrossRef]
- Liu, M.; Guo, J.; Gu, Y.; Gao, J.; Liu, F. Versatile Imidazole-Anion-Derived Ionic Liquids with Unparalleled Activity for Alcoholysis of Polyester Wastes under Mild and Green Conditions. ACS Sustain. Chem. Eng. 2018, 6, 15127–15134. [Google Scholar] [CrossRef]
- Leibfarth, F.A.; Moreno, N.; Hawker, A.P.; Shand, J.D. Transforming Polylactide into Value-Added Materials. J. Polym. Sci. Part A Polym. Chem. 2012, 50, 4814–4822. [Google Scholar] [CrossRef]
- Whitelaw, E.L.; Davidson, M.G.; Jones, M.D. Group 4 salalen complexes for the production and degradation of polylactide. Chem. Commun. 2011, 47, 10004–10006. [Google Scholar] [CrossRef] [Green Version]
- Fliedel, C.; Vila-Viçosa, D.; Calhorda, M.J.; Dagorne, S.; Avilés, T. Dinuclear Zinc–N-Heterocyclic Carbene Complexes for Either the Controlled Ring-Opening Polymerization of Lactide or the Controlled Degradation of Polylactide Under Mild Conditions. ChemCatChem 2014, 6, 1357–1367. [Google Scholar] [CrossRef]
- Jędrzkiewicz, D.; Czeluśniak, I.; Wierzejewska, M.; Szafert, S.; Ejfler, J. Well-controlled, zinc-catalyzed synthesis of low molecular weight oligolactides by ring opening reaction. J. Mol. Catal. A Chem. 2015, 396, 155–163. [Google Scholar] [CrossRef]
- Payne, J.; McKeown, P.; Mahon, M.F.; Emanuelsson, E.A.C.; Jones, M.D. Mono- and dimeric zinc(ii) complexes for PLA production and degradation into methyl lactate—A chemical recycling method. Polym. Chem. 2020. [Google Scholar] [CrossRef]
- McKeown, P.; Brown-Humes, J.; Davidson, M.G.; Mahon, M.F.; Woodman, T.J.; Jones, M.D. Ligands and complexes based on piperidine and their exploitation of the ring opening polymerisation of rac-lactide. Dalton Trans. 2017, 46, 5048–5057. [Google Scholar] [CrossRef] [Green Version]
- Román-Ramírez, L.A.; Mckeown, P.; Jones, M.D.; Wood, J. Poly(lactic acid) Degradation into Methyl Lactate Catalyzed by a Well-Defined Zn(II) Complex. ACS Catal. 2019, 9, 409–416. [Google Scholar] [CrossRef] [Green Version]
- McKeown, P.; McCormick, S.N.; Mahon, M.F.; Jones, M.D. Highly active Mg(ii) and Zn(ii) complexes for the ring opening polymerisation of lactide. Polym. Chem. 2018, 9, 5339–5347. [Google Scholar] [CrossRef] [Green Version]
- McKeown, P.; Román-Ramírez, L.A.; Bates, S.; Wood, J.; Jones, M.D. Zinc Complexes for PLA Formation and Chemical Recycling: Towards a Circular Economy. ChemSusChem 2019, 5233–5238. [Google Scholar] [CrossRef] [PubMed]
- Román-Ramírez, L.A.; McKeown, P.; Jones, M.D.; Wood, J. Kinetics of Methyl Lactate Formation from the Transesterification of Polylactic Acid Catalyzed by Zn(II) Complexes. ACS Omega 2020, 5, 5556–5564. [Google Scholar] [CrossRef] [PubMed]
- McNeill, I.C.; Leiper, H.A. Degradation studies of some polyesters and polycarbonates—1. Polylactide: General features of the degradation under programmed heating conditions. Polym. Degrad. Stab. 1985, 11, 267–285. [Google Scholar] [CrossRef]
- McNeill, I.C.; Leiper, H.A. Degradation studies of some polyesters and polycarbonates-2. Polylactide: Degradation under isothermal conditions, thermal degradation mechanism and photolysis of the polymer. Polym. Degrad. Stab. 1985, 11, 309–326. [Google Scholar] [CrossRef]
- Kopinke, F.; Remmler, M.; Mackenzie, K.; Moder, M.; Wachsen, O. Thermal decomposition of biodegradable polyesters -II. Poly (lactic acid). Polym. Degrad. Stab. 1996, 53, 329–342. [Google Scholar] [CrossRef]
- Nishida, H.; Mori, T.; Hoshihara, S.; Fan, Y.; Shirai, Y.; Endo, T. Effect of tin on poly(L-lactic acid) pyrolysis. Polym. Degrad. Stab. 2003, 81, 515–523. [Google Scholar] [CrossRef]
- Wachsen, O.; Platkowski, K.; Reichert, K.H. Thermal degradation of poly-l -lactide -studies on kinetics, modelling and melt stabilisation. Polym. Degrad. Stab. 1997, 57, 87–94. [Google Scholar] [CrossRef]
- Cam, D.; Marucci, M. Influence of residual monomers and metals on poly (l-lactide) thermal stability. Polymer 1997, 38, 1879–1884. [Google Scholar] [CrossRef]
- Fan, Y.; Nishida, H.; Shirai, Y.; Tokiwa, Y.; Endo, T. Thermal degradation behaviour of poly(lactic acid) stereocomplex. Polym. Degrad. Stab. 2004, 86, 197–208. [Google Scholar] [CrossRef]
- Fan, Y.; Nishida, H.; Mori, T.; Shirai, Y.; Endo, T. Thermal degradation of poly(L-lactide): Effect of alkali earth metal oxides for selective L,L-lactide formation. Polymer 2004, 45, 1197–1205. [Google Scholar] [CrossRef]
- Nishida, H.; Fan, Y.; Mori, T.; Oyagi, N.; Shirai, Y.; Endo, T. Feedstock Recycling of Flame-Resisting Poly(lactic acid)/Aluminum Hydroxide Composite to l,l-lactide. Ind. Eng. Chem. Res. 2005, 44, 1433–1437. [Google Scholar] [CrossRef]
- Fan, Y.; Nishida, H.; Hoshihara, S.; Shirai, Y.; Tokiwa, Y.; Endo, T. Pyrolysis kinetics of poly(L-lactide) with carboxyl and calcium salt end structures. Polym. Degrad. Stab. 2003, 79, 547–562. [Google Scholar] [CrossRef]
- Feng, L.; Feng, S.; Bian, X.; Li, G.; Chen, X. Pyrolysis mechanism of Poly(lactic acid) for giving lactide under the catalysis of tin. Polym. Degrad. Stab. 2018, 157, 212–223. [Google Scholar] [CrossRef]
- Fan, Y.; Nishida, H.; Shirai, Y.; Endo, T. Control of racemization for feedstock recycling of PLLA. Green Chem. 2003, 5, 575–579. [Google Scholar] [CrossRef]
- Mori, T.; Nishida, H.; Shirai, Y.; Endo, T. Effects of chain end structures on pyrolysis of poly(L-lactic acid) containing tin atoms. Polym. Degrad. Stab. 2004, 84, 243–251. [Google Scholar] [CrossRef]
- Abe, H.; Takahashi, N.; Kim, K.J.; Mochizuki, M.; Doi, Y. Thermal degradation processes of end-capped poly(L-lactide)s in the presence and absence of residual zinc catalyst. Biomacromolecules 2004, 5, 1606–1614. [Google Scholar] [CrossRef]
- Coulembier, O.; Moins, S.; Raquez, J.M.; Meyer, F.; Mespouille, L.; Duquesne, E.; Dubois, P. Thermal degradation of poly(l-lactide): Accelerating effect of residual DBU-based organic catalysts. Polym. Degrad. Stab. 2011, 96, 739–744. [Google Scholar] [CrossRef]
- Krall, E.M.; Klein, T.W.; Andersen, R.J.; Nett, A.J.; Glasgow, R.W.; Reader, D.S.; Dauphinais, B.C.; Mc Ilrath, S.P.; Fischer, A.A.; Carney, M.J.; et al. Controlled hydrogenative depolymerization of polyesters and polycarbonates catalyzed by ruthenium(ii) PNN pincer complexes. Chem. Commun. 2014, 50, 4884. [Google Scholar] [CrossRef]
- Westhues, S.; Idel, J.; Klankermayer, J. Molecular catalyst systems as key enablers for tailored polyesters and polycarbonate recycling concepts. Sci. Adv. 2018, 4, eaat9669. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Kindler, T.; Alberti, C.; Fedorenko, E.; Santangelo, N.; Enthaler, S. Ruthenium-Catalyzed Hydrogenative Degradation of End-of-Life Poly(lactide) to Produce 1,2-Propanediol as Platform Chemical. ChemistryOpen 2020, 9, 401–404. [Google Scholar] [CrossRef] [PubMed]
- Shuklov, I.A.; Dubrovina, N.V.; Schulze, J.; Tietz, W.; Kühlein, K.; Börner, A. Propane-1,2-diols from Dilactides, Oligolactides, or Poly-L-lactic Acid (PLLA): From Plastic Waste to Chiral Bulk Chemicals. Chem. A Eur. J. 2014, 20, 957–960. [Google Scholar] [CrossRef] [PubMed]
- Feghali, E.; Cantat, T. Room Temperature Organocatalyzed Reductive Depolymerization of Waste Polyethers, Polyesters, and Polycarbonates. ChemSusChem 2015, 8, 980–984. [Google Scholar] [CrossRef] [PubMed]
- Monsigny, L.; Berthet, J.-C.; Cantat, T. Depolymerization of Waste Plastics to Monomers and Chemicals Using a Hydrosilylation Strategy Facilitated by Brookhart’s Iridium(III) Catalyst. ACS Sustain. Chem. Eng. 2018, 6, 10481–10488. [Google Scholar] [CrossRef]
- Nunes, B.F.S.; Oliveira, M.C.; Fernandes, A.C. Dioxomolybdenum complex as an efficient and cheap catalyst for the reductive depolymerization of waste plastics into value-added compounds and fuels. Green Chem. 2020, 13–16. [Google Scholar] [CrossRef]
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
McKeown, P.; Jones, M.D. The Chemical Recycling of PLA: A Review. Sustain. Chem. 2020, 1, 1-22. https://doi.org/10.3390/suschem1010001
McKeown P, Jones MD. The Chemical Recycling of PLA: A Review. Sustainable Chemistry. 2020; 1(1):1-22. https://doi.org/10.3390/suschem1010001
Chicago/Turabian StyleMcKeown, Paul, and Matthew D. Jones. 2020. "The Chemical Recycling of PLA: A Review" Sustainable Chemistry 1, no. 1: 1-22. https://doi.org/10.3390/suschem1010001
APA StyleMcKeown, P., & Jones, M. D. (2020). The Chemical Recycling of PLA: A Review. Sustainable Chemistry, 1(1), 1-22. https://doi.org/10.3390/suschem1010001