Synthetic process development of laurolactam and C10 -ω-diamine as monomers for thermoplastic polyamide elastomers (TPAE)

α;ω-diamine;EP;TPAE;Hofmann rearrangement;Nitrile reduction;Curtius rearrangement;Laurolactam;Beckmann rearrangement;Schmidt reaction;660

공과대학 화학생물공학부 ;

University:서울대학교 대학원

关键词: α;    ω-diamine;    EP;    TPAE;    Hofmann rearrangement;    Nitrile reduction;    Curtius rearrangement;    Laurolactam;    Beckmann rearrangement;    Schmidt reaction;    660;   

Others  :  http://s-space.snu.ac.kr/bitstream/10371/129431/1/000000140665.pdf

美国|英语

来源: Seoul National University Open Repository

【 摘 要 】

Engineering plastics (EP) are one of the most important materials in the world, because they have many advantages in properties. They remedied general plastic;;s critical shortcomings of thermal and physical properties. Among those EP, thermoplastic elastomer (TPE) has been the focus of the public attention since they have good elastomeric property and reusability through a good thermal stability. In the TPE, amide type of TPE, called thermoplastic amide elastomer (TPAE), has the best performance, which has excellent tear, weathering resistance, good elastic recovery, thermal stability, excellent chemical and hydrolytic resistance and so on. In the domestic market, annual usage of TPAE is growing up gradually. However productions of TPAE’s monomers are not fully developed. As reported our previous paper, we developed synthesis of C9 to C11 monomers from biomass. Herein, we try to introduce a synthetic methodologies C10 diamine and laurolactam based on biomass or petroleum as starting materials in the various reaction methods. We tried to synthesize C10 diamine from C10 or C12 diacid from biomass. C10 diacid was conducted in nitrile reduction process, and C12 diacid was used in Hofmann rearrangement and Curtius rearrangement methods. In the case of laurolactam, we tried to use cyclododecanone as starting materials. We obtained laurolactam via Beckmann rearrangement and Schmidt reaction. In Beckmann rearrangement, we tried to conduct one-pot process. Finally, we fully developed the synthetic methods of C10 diamine and laurolactam. Especially, we conducted one-step processes, which were Curtius rearrangement and one-pot Beckmann rearrangement. One-step reaction reduced cost and reaction time and the yield was higher or similar compared to the other processes. In conclusion, the developed processes have quite meaningful and are applicable in the industry area.