재사용이 가능한 MFB로부터 AMCA의 합성 공정 개발

김종천; 류영; 김석찬; Jong Cheon Kim; Young Ryu; Seok Chan Kim

Applied Chemistry for Engineering, Vol.27, No.5, 508-511, October, 2016

DOI10.14478/ace.2016.1073 Export Citation

재사용이 가능한 MFB로부터 AMCA의 합성 공정 개발

Practical Process Development of AMCA from Recyclable Source MFB

김종천, 류영, 김석찬^†

국민대학교 생명나노화학과

Jong Cheon Kim, Young Ryu, and Seok Chan Kim^†

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

E-mail:

초록

재활용이 가능한 자원인 MFB를 출발 물질로 하여 AMCA의 합성을 진행하였으며, AMBA로부터 AMCA로의 최적의 상업화 합성 조건을 찾고자 촉매, 수소 압력, 반응 온도, 반응 시간 같은 공정 변수를 조사하였다. 최적의 조건은 촉매는 [5% Pd/C : 5% Pt/C : 5% Rh/C (1 : 1 : 1)]의 복합 촉매를 반응 시간은 8 h, 반응 온도는 130 ℃, 압력은 30 bar일때(수율 90%, 순도 99.9%)임을 확인하였다.

A facile synthesis of 4-(aminomethyl)cyclohexanecarboxylic acid (AMCA) from recyclable methyl 4-formylbenzoate (MFB) was described. In particular, we investigated the best process variables such as catalyst, hydrogen pressure, reaction temperature, and reaction time for AMCA conversion from AMBA through hydrogenation reaction. The best conditions were found to be as follows: the catalyst as [5% Pd/C, 5% Pt/C, 5% Rh/C (1 : 1 : 1)] which is a composite catalyst, the pressure as 30 bar, the reaction time as 8 hours and the reaction temperature at 130 ℃. Under the condition, a 90% yield (purity 99.9%) for the mass production of AMCA was achieved.

Keywords:MFB;AMBA;AMCA;Composite catalyst;Hydrogenation reaction

[References]

Kim KD, Yu Y, Jeong HJ, Ham MJ, Kim KL, Kim AN, Davgajantsan O, Park GS, Kim SC, Bull. Korean Chem. Soc., 33, 4275 (2012)
Kim KD, Ryu Y, Kim SC, Appl. Chem. Eng., 25(3), 337 (2014)
Slaughter TF, Greenberg CS, Am. J. Hematol., 36, 32 (1997)
Vessman J, Stromberg S, Anal. Chem., 49, 369 (1977)
Carl M, Svahn F, Karlson L, J. Med. Chem., 29, 448 (1986)
Levine M, Sedlecky R, J. Org. Chem., 24, 115 (1959)
(a) Jiang ZL, Preparation method of 4-chloromethyl benzoic acid t-butyl ester, CN Patent 1907948 (2006). (b) Cook CM, Hausladen MC, Savidakis MC, Fifolt MJ, Ring halogenation of aromatic compounds, U.S. Patent 6124512 A (2000). (c) Jiang ZX, Song ZF, Diao WR, Application of urotropine as catalyst in aminomethylbenzoic acid synthesis, CN Patent 102816077 A (2012). (d) Chang J, Novel technology for synthesis of aminomethylbenzoic acid, CN. Patent 102718673 A (2012).
Li Z, Fang L, Wang J, Dong L, Guo Y, Xie Y, Org. Process Res. Dev., 19, 444 (2015)
Davies RR, Hodson HH, J. Chem. Soc., 279 (1943)
Robert S, Ireland E, Bey P, Org. Synth. Coll., 6, 459 (1988)
Kim SH, Ryu Y, Kim JC, Kim SC, Appl. Chem. Eng., 26(5), 621 (2015)

[Referenced By]

[1] Kim KD, Yu Y, Jeong HJ, Ham MJ, Kim KL, Kim AN, Davgajantsan O, Park GS, Kim SC, Bull. Korean Chem. Soc., 33, 4275 (2012)

[2] Kim KD, Ryu Y, Kim SC, Appl. Chem. Eng., 25(3), 337 (2014)

[3] Slaughter TF, Greenberg CS, Am. J. Hematol., 36, 32 (1997)

[4] Vessman J, Stromberg S, Anal. Chem., 49, 369 (1977)

[5] Carl M, Svahn F, Karlson L, J. Med. Chem., 29, 448 (1986)

[6] Levine M, Sedlecky R, J. Org. Chem., 24, 115 (1959)

[7] (a) Jiang ZL, Preparation method of 4-chloromethyl benzoic acid t-butyl ester, CN Patent 1907948 (2006). (b) Cook CM, Hausladen MC, Savidakis MC, Fifolt MJ, Ring halogenation of aromatic compounds, U.S. Patent 6124512 A (2000). (c) Jiang ZX, Song ZF, Diao WR, Application of urotropine as catalyst in aminomethylbenzoic acid synthesis, CN Patent 102816077 A (2012). (d) Chang J, Novel technology for synthesis of aminomethylbenzoic acid, CN. Patent 102718673 A (2012).

[8] Li Z, Fang L, Wang J, Dong L, Guo Y, Xie Y, Org. Process Res. Dev., 19, 444 (2015)

[9] Davies RR, Hodson HH, J. Chem. Soc., 279 (1943)

[10] Robert S, Ireland E, Bey P, Org. Synth. Coll., 6, 459 (1988)

[11] Kim SH, Ryu Y, Kim JC, Kim SC, Appl. Chem. Eng., 26(5), 621 (2015)