Mathematical Modeling for Continuous Reactive Extrusion of Poly Lactic Acid formation by Ring Opening Polymerization Considering Metal/Organic Catalyst and Alternative Energies
PLA emerged as a promising polymer because of its
property as a compostable, biodegradable thermoplastic made from
renewable sources. PLA can be polymerized from monomers
(Lactide or Lactic acid) obtained by fermentation processes from
renewable sources such as corn starch or sugarcane. For PLA
synthesis, ring opening polymerization (ROP) of Lactide monomer is
one of the preferred methods. In the literature, the technique mainly
developed for ROP of PLA is based on metal/bimetallic catalyst (Sn,
Zn and Al) or other organic catalysts in suitable solvent. However,
the PLA synthesized using such catalysts may contain trace elements
of the catalyst which may cause toxicity. This work estimated the
usefulness and drawbacks of using different catalysts as well as effect
of alternative energies and future aspects for PLA production.
[1] S. Jacobsen, H.-G. Fritz, P.Degée, P.Dubois, and R.Jérôme, “Continuous
reactive extrusion polymerisation of L-lactide ― an engineering view,”
Macromol. Symp., vol. 153, no. 1, pp. 261–273, 2000.
[2] K. Madhavan Nampoothiri, N. R. Nair, and R. P. John, “An overview of
the recent developments in polylactide (PLA) research,” Bioresour.
Technol., vol. 101, no. 22, pp. 8493–8501, Nov. 2010.
[3] P. Dubois, C. Jacobs, R. Jerome, and P. Teyssie, “Macromolecular
engineering of polylactones and polylactides. 4. Mechanism and kinetics
of lactide homopolymerization by aluminum isopropoxide,”
Macromolecules, vol. 24, no. 9, pp. 2266–2270, Apr. 1991.
[4] D. R. Witzke, R. Narayan, and J. J. Kolstad, “Reversible Kinetics and
Thermodynamics of the Homopolymerization of l-Lactide with 2-
Ethylhexanoic Acid Tin(II) Salt,” Macromolecules, vol. 30, no. 23, pp.
7075–7085, Nov. 1997.
[5] N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G.
Lohmeijer, and J. L. Hedrick, “Organocatalytic ring-opening
polymerization,” Chem. Rev., vol. 107, no. 12, pp. 5813–5840, 2007.
[6] W. Jeong, J. L. Hedrick, and R. M. Waymouth, “Organic Spirocyclic
Initiators for the Ring-Expansion Polymerization of β-Lactones,” J. Am.
Chem. Soc., vol. 129, no. 27, pp. 8414–8415, Jul. 2007.
[7] M. Myers, E. F. Connor, T. Glauser, A. Möck, G. Nyce, and J. L.
Hedrick, “Phosphines: Nucleophilic organic catalysts for the controlled
ring-opening polymerization of lactides,” J. Polym. Sci. Part Polym.
Chem., vol. 40, no. 7, pp. 844–851, Apr. 2002.
[8] I. Başaran and A. Oral, “Synthesis and Characterization of Poly(L-Lactic
acid)/Clay Nanocomposite via Metal-Free Process,” Polym.-Plast.
Technol. Eng., vol. 52, no. 12, pp. 1271–1276, 2013.
[9] “InnoREX.” (Online). Available: http://www.innorex.eu/about.php.
[10] S. Jing, W. Peng, Z. Tong, and Z. Baoxiu, “Microwave-irradiated ringopening
polymerization of D,L-lactide under atmosphere,” J. Appl.
Polym. Sci., vol. 100, no. 3, pp. 2244–2247, May 2006.
[11] P. Albert, H. Warth, R. Mülhaupt, and R. Janda, “Comparison of thermal
and microwave-activated polymerization of ε-caprolactone with titanium
tetrabutylate as catalyst,” Macromol. Chem. Phys., vol. 197, no. 5, pp.
1633–1641, May 1996.
[12] A. Södergård and M. Stolt, “Industrial Production of High Molecular
Weight Poly(Lactic Acid),” in Poly(Lactic Acid), R. Auras, L.-T. Lim,
S. E. M. Selke, and H. Tsuji, Eds. John Wiley & Sons, Inc., 2010, pp.
27–41.
[13] R. Mehta, V. Kumar, and S. N. Upadhyay, “Mathematical Modeling of
the Poly(lactic acid) Ring–Opening Polymerization Kinetics,” Polym.-
Plast. Technol. Eng., vol. 46, no. 3, pp. 257–264, 2007.
[14] I. Banu, J.-P. Puaux, G. Bozga, and I. Nagy, “Modeling of L-lactide
Polymerization by Reactive Extrusion,” Macromol. Symp., vol. 289, no.
1, pp. 108–118, 2010.
[15] Y. Yu, G. Storti, and M. Morbidelli, “Ring-Opening Polymerization of
l,l-Lactide: Kinetic and Modeling Study,” Macromolecules, vol. 42, no.
21, pp. 8187–8197, Nov. 2009.
[16] “Compounding and extrusion - Fraunhofer ICT.” (Online). Available:
http://www.ict.fraunhofer.de/en/comp/pe/ce.html.
[17] Y. Yu, G. Storti, and M. Morbidelli, “Kinetics of Ring-Opening
Polymerization of l,l-Lactide,” Ind. Eng. Chem. Res., vol. 50, no. 13, pp.
7927–7940, Jul. 2011.
[18] L. J. Liu, C. Zhang, L. Q. Liao, X. L. Wang, and R. X. Zhuo,
“Microwave-assisted Polymerization of D, L-Lactide with Stannous
Octanoate as Catalyst,” Chin. Chem. Lett., vol. 12, no. 8, pp. 663–664,
2001.
[19] M. Vukomanović, M. Mitrić, S. D. Škapin, E. Žagar, J. Plavec, N.
Ignjatović, and D. Uskoković, “Influence of ultrasonic processing on the
macromolecular properties of poly (d,l-lactide-co-glycolide) alone and in
its biocomposite with hydroxyapatite,” Ultrason. Sonochem., vol. 17, no.
5, pp. 902–908, Jun. 2010.
[20] C. Zhang, L. Liao, and L. Liu, “Rapid Ring-Opening Polymerization of
D,L-Lactide by Microwaves,” Macromol. Rapid Commun., vol. 25, no.
15, pp. 1402–1405, Aug. 2004.
[21] “Ludovic - Twin screw extrusion - SCConsultants.” (Online). Available:
http://www.scconsultants.com/en/ludovic-twin-screw-simulationsoftware.
html..
[22] “Purac home.” (Online). Available: http://www.purac.com/.
[23] “NatureWorks LLC Home Page.” (Online). Available:
http://www.natureworksllc.com/.
[1] S. Jacobsen, H.-G. Fritz, P.Degée, P.Dubois, and R.Jérôme, “Continuous
reactive extrusion polymerisation of L-lactide ― an engineering view,”
Macromol. Symp., vol. 153, no. 1, pp. 261–273, 2000.
[2] K. Madhavan Nampoothiri, N. R. Nair, and R. P. John, “An overview of
the recent developments in polylactide (PLA) research,” Bioresour.
Technol., vol. 101, no. 22, pp. 8493–8501, Nov. 2010.
[3] P. Dubois, C. Jacobs, R. Jerome, and P. Teyssie, “Macromolecular
engineering of polylactones and polylactides. 4. Mechanism and kinetics
of lactide homopolymerization by aluminum isopropoxide,”
Macromolecules, vol. 24, no. 9, pp. 2266–2270, Apr. 1991.
[4] D. R. Witzke, R. Narayan, and J. J. Kolstad, “Reversible Kinetics and
Thermodynamics of the Homopolymerization of l-Lactide with 2-
Ethylhexanoic Acid Tin(II) Salt,” Macromolecules, vol. 30, no. 23, pp.
7075–7085, Nov. 1997.
[5] N. E. Kamber, W. Jeong, R. M. Waymouth, R. C. Pratt, B. G. G.
Lohmeijer, and J. L. Hedrick, “Organocatalytic ring-opening
polymerization,” Chem. Rev., vol. 107, no. 12, pp. 5813–5840, 2007.
[6] W. Jeong, J. L. Hedrick, and R. M. Waymouth, “Organic Spirocyclic
Initiators for the Ring-Expansion Polymerization of β-Lactones,” J. Am.
Chem. Soc., vol. 129, no. 27, pp. 8414–8415, Jul. 2007.
[7] M. Myers, E. F. Connor, T. Glauser, A. Möck, G. Nyce, and J. L.
Hedrick, “Phosphines: Nucleophilic organic catalysts for the controlled
ring-opening polymerization of lactides,” J. Polym. Sci. Part Polym.
Chem., vol. 40, no. 7, pp. 844–851, Apr. 2002.
[8] I. Başaran and A. Oral, “Synthesis and Characterization of Poly(L-Lactic
acid)/Clay Nanocomposite via Metal-Free Process,” Polym.-Plast.
Technol. Eng., vol. 52, no. 12, pp. 1271–1276, 2013.
[9] “InnoREX.” (Online). Available: http://www.innorex.eu/about.php.
[10] S. Jing, W. Peng, Z. Tong, and Z. Baoxiu, “Microwave-irradiated ringopening
polymerization of D,L-lactide under atmosphere,” J. Appl.
Polym. Sci., vol. 100, no. 3, pp. 2244–2247, May 2006.
[11] P. Albert, H. Warth, R. Mülhaupt, and R. Janda, “Comparison of thermal
and microwave-activated polymerization of ε-caprolactone with titanium
tetrabutylate as catalyst,” Macromol. Chem. Phys., vol. 197, no. 5, pp.
1633–1641, May 1996.
[12] A. Södergård and M. Stolt, “Industrial Production of High Molecular
Weight Poly(Lactic Acid),” in Poly(Lactic Acid), R. Auras, L.-T. Lim,
S. E. M. Selke, and H. Tsuji, Eds. John Wiley & Sons, Inc., 2010, pp.
27–41.
[13] R. Mehta, V. Kumar, and S. N. Upadhyay, “Mathematical Modeling of
the Poly(lactic acid) Ring–Opening Polymerization Kinetics,” Polym.-
Plast. Technol. Eng., vol. 46, no. 3, pp. 257–264, 2007.
[14] I. Banu, J.-P. Puaux, G. Bozga, and I. Nagy, “Modeling of L-lactide
Polymerization by Reactive Extrusion,” Macromol. Symp., vol. 289, no.
1, pp. 108–118, 2010.
[15] Y. Yu, G. Storti, and M. Morbidelli, “Ring-Opening Polymerization of
l,l-Lactide: Kinetic and Modeling Study,” Macromolecules, vol. 42, no.
21, pp. 8187–8197, Nov. 2009.
[16] “Compounding and extrusion - Fraunhofer ICT.” (Online). Available:
http://www.ict.fraunhofer.de/en/comp/pe/ce.html.
[17] Y. Yu, G. Storti, and M. Morbidelli, “Kinetics of Ring-Opening
Polymerization of l,l-Lactide,” Ind. Eng. Chem. Res., vol. 50, no. 13, pp.
7927–7940, Jul. 2011.
[18] L. J. Liu, C. Zhang, L. Q. Liao, X. L. Wang, and R. X. Zhuo,
“Microwave-assisted Polymerization of D, L-Lactide with Stannous
Octanoate as Catalyst,” Chin. Chem. Lett., vol. 12, no. 8, pp. 663–664,
2001.
[19] M. Vukomanović, M. Mitrić, S. D. Škapin, E. Žagar, J. Plavec, N.
Ignjatović, and D. Uskoković, “Influence of ultrasonic processing on the
macromolecular properties of poly (d,l-lactide-co-glycolide) alone and in
its biocomposite with hydroxyapatite,” Ultrason. Sonochem., vol. 17, no.
5, pp. 902–908, Jun. 2010.
[20] C. Zhang, L. Liao, and L. Liu, “Rapid Ring-Opening Polymerization of
D,L-Lactide by Microwaves,” Macromol. Rapid Commun., vol. 25, no.
15, pp. 1402–1405, Aug. 2004.
[21] “Ludovic - Twin screw extrusion - SCConsultants.” (Online). Available:
http://www.scconsultants.com/en/ludovic-twin-screw-simulationsoftware.
html..
[22] “Purac home.” (Online). Available: http://www.purac.com/.
[23] “NatureWorks LLC Home Page.” (Online). Available:
http://www.natureworksllc.com/.
@article{"International Journal of Chemical, Materials and Biomolecular Sciences:69162", author = "Satya P. Dubey and Hrushikesh A. Abhyankar and Veronica Marchante and James L. Brighton and Björn Bergmann", title = "Mathematical Modeling for Continuous Reactive Extrusion of Poly Lactic Acid formation by Ring Opening Polymerization Considering Metal/Organic Catalyst and Alternative Energies", abstract = "PLA emerged as a promising polymer because of its
property as a compostable, biodegradable thermoplastic made from
renewable sources. PLA can be polymerized from monomers
(Lactide or Lactic acid) obtained by fermentation processes from
renewable sources such as corn starch or sugarcane. For PLA
synthesis, ring opening polymerization (ROP) of Lactide monomer is
one of the preferred methods. In the literature, the technique mainly
developed for ROP of PLA is based on metal/bimetallic catalyst (Sn,
Zn and Al) or other organic catalysts in suitable solvent. However,
the PLA synthesized using such catalysts may contain trace elements
of the catalyst which may cause toxicity. This work estimated the
usefulness and drawbacks of using different catalysts as well as effect
of alternative energies and future aspects for PLA production.
", keywords = "Alternative energy, bio-degradable, metal catalyst,
poly lactic acid (PLA), ring opening polymerization (ROP).", volume = "9", number = "2", pages = "333-5", }
