ABS 수지의 내열성 강화를 위한 화합물인 N-phenylmaleimide의 상업화를 위한 촉매 개발

정헌주; 양윤승; 김석찬; Hyun Ju Chung; Yun Seung Yang; Seok Chan Kim

Applied Chemistry for Engineering, Vol.28, No.6, 645-648, December, 2017

DOI10.14478/ace.2017.1080 Export Citation

ABS 수지의 내열성 강화를 위한 화합물인 N-phenylmaleimide의 상업화를 위한 촉매 개발

Development of a Catalyst for the Commercialization of N-phenylmaleimide for Strengthening the Heat Resistance of ABS Resins

정헌주, 양윤승, 김석찬^†

국민대학교 응용화학과

Hyun Ju Chung, Yun Seung Yang, and Seok Chan Kim^†

Department of Applied Chemistry, Kookmin University, 77 Jeongneung-ro, Seongbuk-gu, Seoul 02707, Republic of Korea

E-mail:

초록

전량 수입에 의존하고 있는 ABS 수지의 내열성 강화를 위한 화합물인 N-phenylamleimide (PMI)의 상업화를 위한 촉매 개발을 완료하였다. Maleic anhydride와 aniline과 반응을 통하여 중간체인 N-phenylmaleamic acid (PMA)를 정량적으로 얻은 후, PMI를 얻기 위한 촉매를 탐색하였다. Zinc acetate/Et3N의 복합 촉매가 단일 산 촉매보다 우수한 성능을 보임을 확인하였다. 개발된 복합 촉매를 사용하여 추가 정제 공정 없이 90% 수율과 99.3%의 순도로 PMI를 합성할 수 있었다.

A catalyst for promoting the commercialization of N-phenylamleimide (PMI), a compound used to strengthen the heat resistance of ABS resins and also completely imported, was developed. N-phenylmaleamic acid (PMA) was first quantitatively obtained through the reaction of maleic anhydride and aniline. A catalyst was then investigated for obtaining PMI. Zinc acetate /Et3N, composite catalyst, showed better performance than a single acid catalyst. By using the developed composite catalyst, PMI could be synthesized with the yield and purity of 90% and 99.3%, respectively without any further purification processes.

Keywords:ABS resin;Heat resistance;Composite catalyst;PMA;PMI

[References]

Dong D, Tasaka S, Aikawa S, Kamiya S, Inagaki N, Inoue Y, Polym. Degrad. Stabil., 73, 319 (2001)
Ma H, Tong L, Xu Z, Fang Z, Jin Y, Lu F, Polym. Degrad. Stabil., 92, 720 (2007)
Yuksel M, Canak TC, Serhatli IE, Polym. Adv. Technol., 20, 312 (2009)
Song KD, Li HM, J. Macromol. Sci. A, 42, 741 (2005)
Kuehne G, Neumaier A, Copolymers of vinyl chloride with N-substituted maleimides, US Patent 3756991 (1973).
Kim SI, Kwark HJ, Kim JU, Method for Preparation of the N-substitution maleimide, Korean Patent 0923536 (2013).
Ning T, Huang A, Global N-Phenylmaleimide Market Research Report 2014, p. 63-66, QYR Chemical & Material Center, Beijing, China (2014).
Kim JE, Kim SI, Kwag HJ, Method for preparing N-substituted maleimides, US Patent 20110124882 (2011).
Yuan Z, Liao B, Jie Y, Synthetic method of N-phenylmaleimide, Chinese Patent 103664732 (2014).
Kita Y, Nakagawa M, Kanei H, Fukui A, Method for production of maleimides, EU Patent 0334497 (1989).
Shi D, Zhang Q, Xu X, Li J, Zheng L, Cheng X, Method for synthesizing N-benzyl maleimide from immobilized supported acid catalyst, Chinese Patent 101875626 (2009).
Little RD, Masjedizadeh MR, Wallquist O, Mcloughlin JI, The intramolecular Michael reaction, in: L. Paquette (ed.), Organic Reactions, 47, pp. 315-552, John Wiley & Sons, NY, USA (1995).
Halland N, Aburel PS, Jørgensen KA, Angew. Chem.-Int. Edit., 116, 1292 (2004)

[1] Dong D, Tasaka S, Aikawa S, Kamiya S, Inagaki N, Inoue Y, Polym. Degrad. Stabil., 73, 319 (2001)

[2] Ma H, Tong L, Xu Z, Fang Z, Jin Y, Lu F, Polym. Degrad. Stabil., 92, 720 (2007)

[3] Yuksel M, Canak TC, Serhatli IE, Polym. Adv. Technol., 20, 312 (2009)

[4] Song KD, Li HM, J. Macromol. Sci. A, 42, 741 (2005)

[5] Kuehne G, Neumaier A, Copolymers of vinyl chloride with N-substituted maleimides, US Patent 3756991 (1973).

[6] Kim SI, Kwark HJ, Kim JU, Method for Preparation of the N-substitution maleimide, Korean Patent 0923536 (2013).

[7] Ning T, Huang A, Global N-Phenylmaleimide Market Research Report 2014, p. 63-66, QYR Chemical & Material Center, Beijing, China (2014).

[8] Kim JE, Kim SI, Kwag HJ, Method for preparing N-substituted maleimides, US Patent 20110124882 (2011).

[9] Yuan Z, Liao B, Jie Y, Synthetic method of N-phenylmaleimide, Chinese Patent 103664732 (2014).

[10] Kita Y, Nakagawa M, Kanei H, Fukui A, Method for production of maleimides, EU Patent 0334497 (1989).

[11] Shi D, Zhang Q, Xu X, Li J, Zheng L, Cheng X, Method for synthesizing N-benzyl maleimide from immobilized supported acid catalyst, Chinese Patent 101875626 (2009).

[12] Little RD, Masjedizadeh MR, Wallquist O, Mcloughlin JI, The intramolecular Michael reaction, in: L. Paquette (ed.), Organic Reactions, 47, pp. 315-552, John Wiley & Sons, NY, USA (1995).

[13] Halland N, Aburel PS, Jørgensen KA, Angew. Chem.-Int. Edit., 116, 1292 (2004)