Long-chain polyesters and polyamides from biochemically derived fatty acids

European Polymer Journal

Volumn 51, Issue 1, 2014, Pages 159-166

  Kolb, Nicolai ^a   Winkler, Matthias ^a   Syldatk, Christoph ^a   Meier, Michael A R ^a  

^a KARLSRUHE INSTITUTE OF TECHNOLOGY   (Germany)

Author keywords

Fatty acids; Long chain monomers; Renewable polyester and polyamides; Renewable resources; Sophorose lipids

Indexed keywords

CATALYSTS; CHAINS; ESTERS; MELTING POINT; MOLECULAR WEIGHT; MONOMERS; POLYAMIDES; POLYESTERS; TIN;

AVERAGE MOLECULAR WEIGHT; CHEMICAL DERIVATIZATION; FATTY ACID DERIVATIVES; FATTY ACID METHYL ESTER; HYDROXY FATTY ACIDS; LONG CHAINS; RENEWABLE RESOURCE; SOPHOROSE;

FATTY ACIDS;

EID: 84893681061     PISSN: 00143057     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.eurpolymj.2013.11.007     Document Type: Article

References (44)

1. Biermann U, Bornscheuer U, Meier MAR, Metzger JO, Schäfer HJ. Oils and fats as renewable raw materials in chemistry. Angew Chem Int Ed 2011; 50 (17):3854-71.
2. Meier MAR, Metzger JO, Schubert US Plant oil renewable resources as green alternatives in polymer science. Chem Soc Rev 2007; 36 (11):1788-802.
3. Türünc O, Meier MAR. The thiol-ene (click) reaction for the synthesis of plant oil derived polymers. Eur J Lipid Sci Technol 2013; 115 (1):41-54.
4. Turunc O, Firdaus M, Klein G, Meier MAR Fatty acid derived renewable polyamides via thiol-ene additions. Green Chem 2012; 14 (9):2577-83.
5. Desroches M, Caillol S, Auvergne R Boutevin B, David G. Biobased cross-linked polyurethanes obtained from ester/amide pseudo-diols of fatty acid derivatives synthesized by thiol-ene coupling. Polym Chem 2012; 3 (2):450-7.
6. Desroches M, Caillol S, Auvergne R., Boutevin B. Synthesis of pseudo-telechelic diols by transesterification and thiol-ene coupling. Eur J Lipid Sci Technol 2012; 114 (1):84-91.
7. Turunc O, Meier MAR. Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable polymers. Green Chem 2011; 13 (2):314-20.
8. Stemmelen M, Pessel F, Lapinte V., Caillol S, Habas JP, Robin JJ A fully biobased epoxy resin from vegetable oils: from the synthesis of the precursors by thiol-ene reaction to the study of the final material. J Polym Sci Part A: Polym Chem 2011; 49 (11):2434-44.
9. Türünc O, Meier MAR. Fatty acid derived monomers and related polymers via thiol-ene (click) additions. Macromol Rapid Commun 2010; 31 (20):1822-6.
10. Samuelsson J, Jonsson M, Brinck T., Johansson M. Thiol-ene coupling reaction of fatty acid monomers. J Polym Sci Part A: Polym Chem 2004; 42 (24):6346-52. (Pubitemid 40002608)
11. Lligadas G. Renewable polyols for polyurethane synthesis via thiol-ene/yne couplings of plant oils. Macromol Chem Phys 2013; 214 (4):415-22.
12. Desroches M, Caillol S, Lapinte V., Auvergne Rm, Boutevin B. Synthesis of biobased polyols by thiol-ene coupling from vegetable oils. Macromolecules 2011; 44 (8):2489-500.
13. Lligadas G, Ronda JC, Galià M, Cádiz V. Monomers and polymers from plant oils via click chemistry reactions. J Polym Sci Part A: Polym Chem 2013; 51 (10):2111-24.
14. Ohlmann DM, Tschauder N, Stockis J-P, Gooßen K, Dierker M., Gooßen LJ. Isomerizing olefin metathesis as a strategy to access defined distributions of unsaturated compounds from fatty acids. J Am Chem Soc 2012; 134 (33):13716-29.
15. Miao X, Fischmeister C, Dixneuf P.H., Bruneau C., Dubois JL, Couturier JL Polyamide precursors from renewable 10-undecenenitrile and methyl acrylate via olefin cross-metathesis. Green Chem 2012.
16. Miao X, Malacea R, Fischmeister C., Bruneau C, Dixneuf PH Ruthenium-alkylidene catalysed cross-metathesis of fatty acid derivatives with acrylonitrile and methyl acrylate: a key step toward long-chain afunctional and amino acid compounds. Green Chem 2011; 13 (10):2911-9.
17. Meier MAR. Metathesis with oleochemicals: new approaches for the utilization of plant oils as renewable resources in polymer science. Macromol Chem Phys 2009; 210 (13-14):1073-9.
18. Malacea R, Fischmeister C, Bruneau C., Dubois J-L, Couturier J-L, Dixneuf PH Renewable materials as precursors of linear nitrile-acid derivatives via cross-metathesis of fatty esters and acids with acrylonitrile and fumaronitrile. Green Chem 2009; 11 (2):152-5.
19. Rybak A, Meier MAR Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact. Green Chem 2008; 10 (10):1099-104.
20. Rybak A, Meier MAR Cross-metathesis of fatty acid derivatives with methyl acrylate: renewable raw materials for the chemical industry. Green Chem 2007; 9 (12):1356-61.
21. Mutlu H, Meier MAR. Unsaturated PA X, 20 from renewable resources via metathesis and catalytic amidation. Macromol Chem Phys 2009; 210 (12):1019-25.
22. Forman GS, Bellabarba RM, Tooze R.P., Slawin AMZ, Karch R Winde R Metathesis of renewable unsaturated fatty acid esters catalysed by a phoban-indenylidene ruthenium catalyst. J Organomet Chem 2006; 691 (24-25):5513-6. (Pubitemid 44810872)
23. Trzaskowski J, Quinzler D, Bährle C, Mecking S. Aliphatic long-chain C20 polyesters from olefin metathesis. Macromol Rapid Commun 2011; 32 (17):1352-6.
24. Vilela C, Silvestre AJD, Meier MAR. Plant oil-based long-chain C26 monomers and their polymers. Macromol Chem Phys 2012; 213 (21):2220-7.
25. Fürst M.R.L., Goff RL, Quinzler D, Mecking S., Botting CH, Cole-Hamilton DJ. Polymer precursors from catalytic reactions of natural oils. Green Chem 2012; 14 (2):472-7.
26. Cole-Hamilton DJ. Nature's polyethylene. Angew Chem Int Ed 2010; 49 (46):8564-6.
27. Stempfle F, Ortmann P, Mecking S. Which polyesters can mimic polyethylene? Macromol Rapid Commun 2013; 34 (1):47-50.
28. Griehl W, Ruestem D. Nylon-12-preparation, properties, and applications. Ind Eng Chem 1970; 62 (3):16-22.
29. Genas M. Rilsan (Polyamid 11), Synthese und Eigenschaften. Angew Chem 1962; 74 (15):535-40.
30. Stempfle F, Quinzler D, Heckler I., Mecking S. Long-chain linear C19 and C23 monomers and polycondensates from unsaturated fatty acid esters. Macromolecules 2011; 44 (11):4159-66.
31. Hablot E, Donnio B, Bouquey M., Avérous L. Dimer acid-based thermoplastic bio-polyamides: reaction kinetics, properties and structure. Polymer 2010; 51 (25):5895-902.
32. Pardal F, Salhi S, Rousseau B., Tessier M, Claude S, Fradet A Unsaturated polyamides from bio-based Z-octadec-9-enedioic acid. Macromol Chem Phys 2008; 209 (1):64-74.
33. Marchildon K. Polyamides - still strong after seventy years. Macromol React Eng 2011; 5 (1):22-54.
34. Winkler M, Steinbiß M, Meier MAR. A more sustainable Wohl-Ziegler bromination: versatile derivatisation of unsaturated FAMEs and synthesis of renewable polyamides. Eur J Lipid Sci Technol 2013:n/a-a.
35. Kolb N, Meier MAR. Monomers and their polymers derived from saturated fatty acid methyl esters and dimethyl carbonate. Green Chem 2012; 14 (9):2429-35.
36. Lu W, Ness JE, Xie W, Zhang X., Minshull J, Gross RA Biosynthesis of monomers for plastics from renewable oils. J Am Chem Soc 2010; 132 (43):15451-5.
37. Van Bogaert I.A., Saerens K, De Muynck C, Develter D, Soetaert W., Vandamme E. Microbial production and application of sophorolipids. Appl Microbiol Biotechnol 2007; 76 (1):23-34. (Pubitemid 47194681)
38. Peng Y, Decatur J, Meier MAR, Gross RA Ring-opening metathesis polymerization of a naturally derived macrocyclic glycolipid. Macromolecules 2013; 46 (9):3293-300.
39. Gao W, Hagver R, Shah V., Xie W, Gross RA Ilker MF, et al. Glycolipid polymer synthesized from natural lactonic sophorolipids by ring-opening metathesis polymerization. Macromolecules 2006; 40 (2):145-7.
40. Ortmann P, Mecking S. Long-spaced aliphatic polyesters. Macromolecules 2013; 46 (18):7213-8.
41. Phukan P, Bauer M, Maier ME Facile generation of alkenes and dienes from tosylates. Synthesis 2003; 2003 (09):1324-8. (Pubitemid 36836417)
42. Daniel H-J, Reuss M., Syldatk C. Production of sophorolipids in high concentration from deproteinized whey and rapeseed oil in a two stage fed batch process using Candida bombicola ATCC 22214 and Cryptococcus curvatus ATCC 20509. Biotechnol Lett 1998; 20 (12):1153-6. (Pubitemid 29034189)
43. Mutlu H, Hofsa, Montenegro RE, Meier MAR Self-metathesis of fatty acid methyl esters: full conversion by choosing the appropriate plant oil. RSC Adv 2013; 3 (15):4927-34.
44. Fokou PA Meier MAR Use of a renewable and degradable monomer to study the temperature-dependent olefin isomerization during ADMET polymerizations. J Am Chem Soc 2009; 131 (5):1664-5.