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http://dx.doi.org/10.7473/EC.2013.48.1.24

Synthesis of Monomers for Polyamide-type TPEs from Oleic Acid  

Koh, Moo-Hyun (Department of Chemical and Biological Engineering, Seoul National University)
Kim, Hyun Su (Department of Chemical and Biological Engineering, Seoul National University)
Kim, Hyeonjeong (Department of Chemical and Biological Engineering, Seoul National University)
Shin, Nara (Department of Chemical and Biological Engineering, Seoul National University)
Yoo, Dongwon (Department of Chemical and Biological Engineering, Seoul National University)
Kim, Young Gyu (Department of Chemical and Biological Engineering, Seoul National University)
Publication Information
Elastomers and Composites / v.48, no.1, 2013 , pp. 24-29 More about this Journal
Abstract
We have developed the synthetic processes for the monomers of polyamide-type TPEs (thermoplastic elastomers, TPAEs) obtained from vegetable oil. TPAEs have several superior physical properties to those of thermoplastic elastomers (TPEs). From the common starting material, oleic acid, which is commonly found in various vegetable oils, we have synthesized three ${\omega}$-amino acid monomers ($C_9$, $C_{10}$ and $C_{11}$ ${\omega}$-amino acid) and three ${\alpha}$, ${\omega}$-dicarboxylic acids($C_9$, $C_{10}$ and $C_{11}$ ${\alpha}$, ${\omega}$-dicarboxylic acid) for TPAEs in good yields.
Keywords
oleic acid; ${\alpha}$, ${\omega}$-dicarboxylic acids; ${\omega}$-amino acids; monomers of thermoplastic elastomers (TPEs);
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1 A. Sasmal, D. Sahoo, R. Nanda, P. Nayak, P. L. Nayak, J. K. Mishra, Y. W. Chang, J. Y. Yoon, "Biodegradable Nanocomposites from Maleated Polycaprolactone/Soy Protein Isolate Blend with Organoclay: Preparation, Characterization, and Properties", Polym. Compos., 30, 708 (2009).   DOI   ScienceOn
2 P. L. Nayak, "Natural Oil-Based Polymers: Opportunities and Challenges", J. Macromol. Sci. Polymer Rev., 40, 1 (2000).   DOI   ScienceOn
3 M. Eissen, J. O. Metzger, E. Schmidt, "10 Years after Rio-Concepts on the Contribution of Chemistry to a Sustainable Development", Angew. Chem. Int. Ed., 41, 414 (2002).   DOI   ScienceOn
4 M. S. Lindblad, Y. Liu, A. Albertsson, E. Ranucci, S. Karlsson, "Polymers from Renewable Resources", Adv. Polym. Sci., 157, 139 (2002).   DOI
5 A. K. Bhowmick, H. L. Stephens, "Handbook of elastomers", 2nd Ed. p. 417, Marcel Dekker, 2001.
6 J. G. Drobny, "Handbook of thermoplastic elastomers", p. 306, William Andrew, New York, 2007.
7 A. Gandini, "Polymers from Renewable Resources: A Challenge for the Future of Macromolecular Materials", Macromolecules, 41, 9491 (2008).   DOI   ScienceOn
8 U. Biermann, J. O. Metzger, "Catalytic C,C-bond forming additions to unsaturated fatty compounds", Topics Catal., 27, 119 (2004).   DOI   ScienceOn
9 R. Aelion, "Nylon 6 and Related Polymers", Ind. Eng. Chem., 53, 826 (1961).   DOI
10 F. O. Ayorinde, E. Y. Nana, P. D. Nicely, A. S. Woods, E. O. Price, C. P. Nwaonicha, "Syntheses of 12-Aminododecanoic and 11-Aminoundecanoic Acids from Vernolic Acid", J. Am. Oil Chem. Soc., 74, 531 (1997).   DOI   ScienceOn
11 M. -H. Koh, H. Kim, N. Shin, H. S. Kim, D. Yoo, Y. G. Kim, "Divergent Process for $C_{10}$, $C_{11}$ and $C_{12}$ $\omega$-Amino Acid and $\alpha$,$\omega$-Dicarboxylic Acid Monomers of Polyamides from Castor Oil as a Renewable Resource", Bull. Korean Chem. Soc., 33, 1873 (2012).   과학기술학회마을   DOI   ScienceOn
12 K. Sisido, Y. Kazama, H. Kodama, H. Nozaki, "Condensation of t-Butyl Esters with Organic Halides in the Presence of Alkali Amides", J. Am. Chem. Soc., 81, 5817 (1959).   DOI
13 A. S. Kalgutkar, B. C. Crews, L. J. Marnett, "Design, Synthesis, and Biochemical Evaluation of N-Substituted Maleimides as Inhibitors of Prostaglandin Endoperoxide Synthases", J. Med. Chem., 39, 1692 (1996).   DOI   ScienceOn
14 M. Periasamy, C. Narayana, M. Anitha, "A Simple One-Pot Method for Conversion of Terminal Alkenes into Carboxylic Acid via Hydroboration", Indian J. Chem. B, 25, 844 (1986).
15 B. P. Fabrichnyi, I. F. Shalavina, Y. L. Gol'dfarb, "Synthesis of Amino Acid of Aliphatic Series from Thiophene Derivatives. III. Synthesis of $\omega$-Amino Acid", Zh. Obshch. Khim., 28, 2520 (1958).
16 M. S. Kharasch, G. Sosnovsky, "Structure of Peroxides Derived from Cyclohexanone and Hydrogen Peroxide", J. Org. Chem., 23, 1322 (1958).   DOI
17 H. Zahn, H. D. Stolper, G. Heidemann, "Cyclo-bis-[$\omega$ -amino-dodecansäure]-amid", Chem. Ber., 98, 3251 (1965)   DOI
18 J. R. McNesby, Jr. C. A. Heller, "Oxidation of Liquid Aldehydes by Molecular Oxygen", Chem. Rev., 54, 325 (1954).   DOI
19 P. J. Garratt, C. W. Doecke, J. C. Weber, L. A. Paquette, "Intramolecular Anionic Cyclization Route to Capped [3]Perisylanes", J. Org. Chem., 51, 449 (1986).   DOI
20 M. B. Smith, J. March, "March's Advanced Organic Chemistry", 6th Ed. p. 1288, Wiley, New York, 2007.
21 T. Gross, A. M. Seayad, M. Ahmad, M. Beller, "Synthesis of Primary Amines: First Homogeneously Catalyzed Reductive Amination with Ammonia ", Org. Lett., 4, 2055 (2002).   DOI   ScienceOn
22 L. C. R. Henry, "Nitro-alcohols", Hebd. Seances. Acad. Sci., 120, 1265 (1895).
23 F. A. Luzzio, "The Henry Reaction: Recent Examples", Tetrahedron, 57, 915 (2001).   DOI   ScienceOn
24 J. U. Nef, "Constitution of Salts of the Nitro-paraffins", Liebigs Ann. Chem., 280, 263 (1894).   DOI
25 Y. Ito, Y. Ohashi, T. Miyagishima, "Synthesis of 2-Deoxy-2-methylamino- D-gulose, a Component of Streptothricin-like Antibiotics", Carbohyd. Res., 9, 125 (1969).   DOI   ScienceOn
26 R. Ballini, M. Petrini, "Recent Synthetic Developments in the Nitro to Carbonyl Conversion (Nef Reaction)", Tetrahedron, 60, 1017 (2004).   DOI   ScienceOn
27 E. Knoevenagel, "Condensation von Malondiure mitaromatiachen Aldehyden durch Ammoniak und Amine", Chem. Ber., 31, 2596 (1898).   DOI
28 S. T. Kemme, T. Smejkal, B. Breit, "Combined Transition-Metal- and Organocatalysis: An Atom Economic C3 Homologation of Alkenes to Carbonyl and Carboxylic Compounds", Chem. Eur. J., 16, 3423 (2010).   DOI   ScienceOn