Korean Journal of Chemical Engineering, Vol.38, No.6, 1079-1086, 2021
Catalytic production of hexamethylenediamine from renewable feedstocks
Renewable biomass-derived chemicals have received considerable interest as a potential substitute for petroleum-derived chemicals. Hexamethylenediamine is a key intermediate in manufacturing nylon 66, a synthetic polymer that is broadly used in society. This article reviews the catalytic production of hexamethylenediamine from biomass-derived chemical feedstocks, and specifically the bio-based routes for obtaining hexamethylenediamine. While methods to directly convert biomass to hexamethylenediamine have yet to be commercialized, the use of heterogeneous catalytic systems via combined processes appears to be a promising and emerging chemical pathway to achieve this goal. Current proposed routes for the renewable production of hexamethylenediamine are not yet entirely competitive with petrochemical production techniques, predominantly because of low efficiency and high cost. However, many opportunities exist to advance technologies that exploit renewable and bio-based feedstocks to generate hexamethylenediamine. Thus, the commercialization of biomass-derived nylon monomers appears achievable in the near future.
[References]
Wittcoff HA, Reuben BG, Plotkin JS, Industrial organic chemicals, (2013).
Song W, Wang S, Xu D, Guo Y, Yang C, Zhang J, Li Y, Korean J. Chem. Eng. , 36 (10), 1604, 2019
Kim S, Kwon EE, Kim YT, Jung S, Kim HJ, Huber GW, Lee J, Green Chem. , 21 , 3715, 2019
Wang Z, Fu Z, Lin W, Li S, Song W, Korean J. Chem. Eng. , 36 (8), 1235, 2019
Lee HW, Jeong HS, Ju YM, Lee SM, Korean J. Chem. Eng. , 37 (7), 1174, 2020
AbdelSalam H, El-Maghrbi HH, Zahran F, Zaki T, Korean J. Chem. Eng. , 37 (4), 670, 2020
Park C, Lee J, Green Chem. , 22 , 2628, 2020
Pham HM, Kang MJ, Kim KA, Im CG, Hwang SY, Cha HG, Korean J. Chem. Eng. , 37 (3), 556, 2020
Dikshit PK, Jun HB, Kim BS, Korean J. Chem. Eng. , 37 (3), 387, 2020
Purnama A, Wijaya K, Tahir I, Suyono EA, Budiman A, Korean J. Chem. Eng. , 37 (3), 466, 2020
Si Z, Zhang X, Zuo M, Wang T, Sun Y, Tang X, Zeng X, Lin L, Korean J. Chem. Eng. , 37 (2), 224, 2020
Holbery J, Houston D, JOM , 58 , 80, 2006
Papadopoulou EL, Pignatelli F, Marras S, Marini L, Davis A, Athanassiou A, Bayer IS, RSC Adv. , 6 , 6823, 2016
Pan G, Zhao Y, Xu H, Hou X, Yang Y, J. Clean Prod. , 117 , 212, 2016
Weissermel K, Arpe HJ, Industrial organic chemistry, Wiley-VCH, Weinheim (2003).
Maximize Market Research, https://www.maximizemarketresearch.com/market (2019).
Botelho EC, Scherbakoff N, Rezende MC, Kawamoto AM, Sciamareli J, Macromolecules , 34 (10), 3367, 2001
Pelckmans M, Renders T, Van de Vyver S, Sels BF, Green Chem. , 19 , 5303, 2017
Balladur V, Fouilloux P, Debellefon C, Appl. Catal. A: Gen. , 133 (2), 367, 1995
Lee Y, Lee SW, Kim HJ, Kim YT, Lin KYA, Lee J, Appl. Sci. , 10 , 7506, 2020
Li H, Xu Y, Deng JF, New J. Chem. , 23 , 1059, 1999
Harper MJ, United States Patent, US6156694A (2000).
Yu XB, Li HX, Deng JF, Appl. Catal. A: Gen. , 199 (2), 191, 2000
Li HX, Xu YP, Li H, Deng JF, Appl. Catal. A: Gen. , 216 (1-2), 51, 2001
Medina F, Salagre P, Sueiras JE, Fierro JLG, J. Mol. Catal. , 81 , 387, 1993
Jia Z, Zhen B, Han M, Wang C, Catal. Commun. , 73 , 80, 2016
Wang C, Jia Z, Zhen B, Han M, Molecules , 23 , 92, 2018
Liao H, Liu S, Hao F, Liu P, You K, Liu D, Luo HA, React. Kinet. Catal. Lett. , 109 , 475, 2013
Liu S, Hao F, Liu P, Luo HA, Liao H, Res. Chem. Intermed. , 41 , 5879, 2015
Lv Y, Hao F, Xiong S, Liu P, Luo HA, RSC Adv. , 6 , 60933, 2016
Lv Y, Hao F, Liu P, Xiong S, Luo H, React. Kinet. Mech. Catal. , 119 , 555, 2016
Lv Y, Hao F, Liu PL, Xiong SF, Luo HA, J. Mol. Catal. A-Chem. , 426 , 15, 2017
Lv Y, Li J, Feng S, Liu PL, Hao F, Xiong W, Luo HA, Chem. Eng. J. , 346 , 203, 2018
Alini S, Bottino A, Capannelli G, Carbone R, Comite A, Vitulli G, J. Mol. Catal. A-Chem. , 206 (1-2), 363, 2003
Wilson K, Adams DJ, Rothenberg G, Clark JH, J. Mol. Catal. A-Chem. , 159 (2), 309, 2000
Gallezot P, Chem. Soc. Rev. , 41 , 1538, 2012
Sheldon RA, Green Chem. , 16 , 950, 2014
Pacheco JJ, Davis ME, Proc. Natl. Acad. Sci. USA , 111 , 8363, 2014
Beerthuis R, Rothenberg G, Shiju NR, Green Chem. , 17 , 1341, 2015
Lee Y, Kwon EE, Lee J, Rev. Environ. Sci. Biotechnol. , 18 , 317, 2019
Lee Y, Lin KYA, Kwon EE, Lee J, J. Clean Prod. , 227 , 624, 2019
Cole-Hamilton DJ, Science , 299 , 1702, 2003
Dev A, Srivastava AK, Karmakar S, Handbook of nanomaterials for industrial applications, 217 (2018).
Matthieu C, Dietrich E, Delmas H, Jenck J, Chem. Eng. Sci. , 47 , 2289, 1992
Jolyvuillemin C, Gavroy D, Cordier G, Debellefon C, Delmas H, Chem. Eng. Sci. , 49 (24), 4839, 1994
Rostrup-Nielsen JR, Science , 308 , 1421, 2005
Goldemberg J, Science , 315 , 808, 2007
Zhang MH, Yu YZ, Ind. Eng. Chem. Res. , 52 (28), 9505, 2013
Angelici C, Weckhuysen BM, Bruijnincx PCA, ChemSusChem , 6 , 1595, 2013
Makshina EV, Dusselier M, Janssens W, Degreve J, Jacobs PA, Sels BF, Chem. Soc. Rev. , 43 , 7917, 2014
Ohnishi R, Akimoto T, Tanabe K, J. Chem. Soc., Chem. Commun., 1613 (1985).
Chieregato A, Ochoa JV, Bandinelli C, Fornasari G, Cavani F, Mella M, ChemSusChem , 8 , 377, 2015
Ochoa JV, Bandinelli C, Vozniuk O, Chieregato A, Malmusi A, Recchi C, Cavani F, Green Chem. , 18 , 1653, 2016
Pomalaza G, Capron M, Ordomsky V, Dumeignil F, Catalysts , 6 , 203, 2016
Kyriienko PI, Larina OV, Soloviev SO, Orlyk SM, Calers C, Dzwigaj S, ACS Sustainable Chem. Eng. , 5 , 2075, 2017
Wang Z, Comprehensive organic name reactions and reagents, USA, 1728 (2010).
Zeitsch KJ, The chemistry and technology of furfural and its many by-products, The Netherlands (2000).
Lange JP, van der Heide E, van Buijtenen J, Price R, ChemSusChem , 5 , 150, 2012
Choudhary H, Nishimura S, Ebitani K, Chem. Lett. , 41 (4), 409, 2012
Choudhary H, Nishimura S, Ebitani K, Appl. Catal. A: Gen. , 458 , 55, 2013
Deshpande RM, Buwa VV, Rode CV, Chaudhari RV, Mills PL, Catal. Commun. , 3 , 269, 2002
Ly BK, Minh DP, Pinel C, Besson M, Tapin B, Epron F, Especel C, Top. Catal. , 55 , 466, 2012
Chung SH, Park YM, Kim MS, Lee KY, Catal. Today , 185 (1), 205, 2012
Ly BK, Tapin B, Aouine M, Delichere P, Epron F, Pinel C, Especel C, Besson M, ChemCatChem , 7 , 2161, 2015
Kang KH, Hong UG, Bang Y, Choi JH, Kim JK, Lee JK, Han SJ, Song IK, Appl. Catal. A: Gen. , 490 , 153, 2015
Zhang W, Zhu YL, Niu S, Li YW, J. Mol. Catal. A-Chem. , 335 (1-2), 71, 2011
Pushkarev VV, Musselwhite N, An K, Alayoglu S, Somorjai GA, Nano Lett. , 12 , 5196, 2012
An K, Musselwhite N, Kennedy G, Pushkarev VV, Baker LR, Somorjai GA, J. Colloid Interface Sci. , 392 , 122, 2013
Ishida T, Kume K, Kinjo K, Honma T, Nakada K, Ohashi H, et al., ChemSusChem , 9 , 3441, 2016
Fischer R, Pinkos R, United States Patent, US5905159A (1999).
Vecchini N, Galeotti A, Pisano A, International Patent, WO2016092517A1 (2016).
Wang YC, Sun DL, Yamada Y, Sato S, Appl. Catal. A: Gen. , 562 , 11, 2018
Richard R, Jacquin M, Dorato M, Pacheco N, Rannoux C, United States Patent, US10322978B2 (2019).
Sato F, Sato S, Yamada Y, Nakamura M, Shiga A, Catal. Today , 226 , 124, 2014
Nakagawa Y, Kasumi T, Ogihara J, Tamura M, Arai T, Tomishige K, ACS Omega , 5 , 2520, 2020
Childers KG, Dreher SD, Lee J, Williams JM, Org. Process Res. Dev. , 10 , 934, 2006
Liu L, Asano T, Nakagawa Y, Tamura M, Tomishige K, Green Chem. , 22 , 2375, 2020
Jing F, Katryniok B, Araque M, Wojcieszak R, Capron M, et al., Catal. Sci. Technol. , 6 , 530, 2016
Decker M, Schmidt J, Hoffmann H, Pistor HJ, United States Patent, US3671566A (1972).
Shi J, Zhang X, Chen G, Fan L, Shu C, Dang G, Zhan X, et al., China Patent, CN106146345B (2018).
Musser MT, “Adipic acid”, Ullmann’s encyclopedia of industrial chemistry, Wiley-VCH, Weinheim (2000).
Blanco DE, Dookhith AZ, Modestino MA, React. Chem. Eng. , 4 , 8, 2019
Dai JJ, Huang YB, Fang C, Guo QX, Fu Y, ChemSusChem , 5 , 617, 2012
Werpy T, Petersen G, Top value added chemicals from biomass: Volume 1 - results of screening for potential candidates from sugars and synthetic gas, (20014).
Baldwin JE, North M, Flinn A, Moloney MG, Tetrahedron , 45 , 1453, 1989
de Bellefon C, Fouilloux P, Catal. Rev.-Sci. Eng. , 36 , 459, 1994
Howk BW, United States Patent, US2166151A (1939).
Augustine RL, Catal. Rev.-Sci. Eng., 13, 285 (1976).
Herzog BD, Smiley RA, “Hexamethylenediamine”, Ullmann’s encyclopedia of industrial chemistry (2012).
Sengupta SK, Koch TA, Krause KR, United States Patent, US5900511A (1999).
Lv Y, Cui HS, Liu PL, Hao F, Xiong W, Luo HA, J. Catal. , 372 , 330, 2019
Gilkey MJ, Xu B, ACS Catal. , 6 , 1420, 2016
Liu H, Guo Y, Yu Y, Yang W, Shen M, Liu X, Geng S, Li J, Yu C, Yin Z, Li H, J. Mater. Chem. A , 6 , 17323, 2018
Serra M, Salagre P, Cesteros Y, Medina F, Sueiras JE, J. Catal. , 209 (1), 202, 2002
van Putten RJ, van der Waal JC, de Jong E, Rasrendra CB, Heeres HJ, de Vries JG, Chem. Rev. , 113 (3), 1499, 2013
Nikolla E, Roman-Leshkov Y, Moliner M, Davis ME, ACS Catal. , 1 , 408, 2011
Pagan-Torres YJ, Wang T, Gallo JMR, Shanks BH, Dumesic JA, ACS Catal. , 2 , 930, 2012
Xu S, Yin C, Pang D, Hu F, Wu Y, Miao Y, Gao L, Xiao G, Sustain. Energy Fuels , 3 , 390, 2019
Buntara T, Noel S, Phua PH, Melian-Cabrera I, Vries JGD, Heeres HJ, Angew. Chem.-Int. Edit. , 50 , 7083, 2011
Dias EL, Shoemaker JAW, Boussie TR, Murphy VJ, United States Patent, US9518005B2 (2016).
Horlenko T, Tatum HW, United States Patent, 3,215,742 (1965).
Muller C, et al., United States Patent, US20160326092A1 (2016).
Dros AB, Larue O, Reimond A, De Campo F, Pera-Titus M, Green Chem. , 17 , 4760, 2015
Thaore V, Chadwick D, Shah N, Chem. Eng. Res. Des. , 135 , 140, 2018
Kim SS, Tsang YF, Kwon EE, Lin KYA, Lee JC, Korean J. Chem. Eng. , 36 (1), 1, 2019
Park YK, Ha JM, Oh S, Lee J, Chem. Eng. J. , 404 , 126527, 2021
Han J, Kim Y, Jackson DHK, Chang H, Kim HW, Lee J, et al., Appl. Catal. B: Environ. , 273 , 119037, 2020
이전 논문 다음 논문
Result Search