Abstract
Aqueous solutions of sodium salt of p-nitrobenzoic acid (p-NBA) were hydrogenated in mild conditions in the presence of palladium (PdNPs) and gold nanoparticles (AuNPs) immobilized within macroporous amphoteric cryogel based on N,N-dimethylaminoethylmethacrylate (DMAEM) and methacrylic acid (MAA). The morphology of the macroporous catalyst DMAEM-co-MAA/AuNPs was characterized using SEM. The pore sizes of sponge-like porous structure of cryogels are in the range of 5–40 µm, while the average sizes of AuNPs immobilized within the macroporous amphoteric cryogel are 80 ± 20 nm. The reduction of p-NBA to p-aminobenzoic acid (p-ABA) and further to by-products p,p′-azodibenzoate and sodium 4-(4-aminobenzamido)benzoate was confirmed by Raman and 1H NMR spectroscopy. The conversion degree, kinetic parameters, and activation energies of hydrogenation of p-NBA were found.
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Reproduced with permission from Ref. [39]



Reproduced with permission from Ref. [35]








References
E.A. Bekturov, S.E. Kudaibergenov, Catalysis by Polymers (Wiley, New York, 2008)
A.D. Pomogailo, G.I. Dzhardimalieva, Metallopolymeric Hybrid Nanocomposites (Nauka, Moscow, 2015)
Zh.E. Ibrayeva, S.E. Kudaibergenov, E.A. Bekturov, Stabilization of Metal Nanoparticles by Hydrophilic Polymers (in Russian) (LAP Lambert Academic Publishing, Germany, 2013)
G.I. Dzhardimalieva, V.G. Dorokhov, N.D. Golubeva, S.I. Pomogailo, A.M. Lyakhovich, V.I. Savchenko, A.D. Pomogailo, Russ. Chem. Bull. Int. Ed. 58, 2070 (2009)
S.E. Kudaibergenov, G.S. Tatykhanova, B.S. Selenova, J. Inorg. Organomet. Polym. 26, 1198 (2016)
S.E. Kudaibergenov, N. Nuraje, V.V. Khutoryanskiy, Soft Matter 8, 9302 (2012)
V.I. Lozinsky, Russ. Chem. Rev. 71, 489 (2002)
V.I. Lozinskiy, I.Y. Galaev, F.M. Plieva, I.N. Savina, H. Jungvid, B. Mattiasson, Trends Biotechnol. 10, 445 (2003)
V.I. Lozinsky, Adv. Polym. Sci. 263, 1 (2014)
F. Hapiot, S. Menuel, E. Monflier, ACS Catal. 3, 1006 (2013)
C. Yang, G.-F. Liu, X.-L. Zhou et al., Catal. Lett. 145, 1778 (2015)
N. Sahiner, S. Yildiz, M. Sahiner, Z.A. Issa, H. Al-Lohedan, Appl. Surf. Sci. 354, 388 (2015)
N. Sahiner, F. Seven, Energy 71, 170 (2014)
N. Sahiner, S. Yildiz, Fuel Process. Technol. 126, 324 (2014)
N. Sahiner, F. Seven, RSC Adv. 4, 23886 (2014)
M. Ajmal, M. Siddiq, N. Aktas, N. Sahiner, RSC Adv. 5, 43873 (2015)
B. Andersson, AlChE J. 28, 333 (1982)
E.F. Litvin, L.K. Freidlin, R.N. Gurskii, R.V. Istratova, I.L. Vaisman, Bull. Acad. Sci. USSR Chem. Sci. 24, 1620 (1975)
P.A. Simonov, A.V. Romanenko, V.A. Likholobov, Solid Fuel Chem. 48, 364 (2014)
S. Jana, S. Pande, A.K. Sinha, S. Sarkar, M. Pradhan, M. Basu, Y. Negishi, A. Pal, T. Pal, Langmuir 10, 847 (2010)
G.N. Al’tshuler, G.Yu. Shkurenko, A.A. Gorlov, Russ. J. Phys. Chem. A 89, 372 (2015)
S. Jana, S. Pande, S. Panigrahi, S. Praharaj, S. Basu, A. Pal, T. Pal, Langmuir 22, 7091 (2006)
W. Wang, Y. Song, Q. Lin, K. Yang, Bull. Mater. Sci. 37, 797 (2014)
C. Fernandez, E. Lujano, U. Macias, et al., Catal. Lett. 95, 143 (2004)
F. Lapicque, A. Storck, J. Appl. Electrochem. 16, 825 (1986)
M.G. Abdullaev, Z.Sh. Abdullaeva, M.V. Klyuev, Z.G. Gebekova, Pharm. Chem. J. 48, 343 (2014)
H.-G. Zendel, M. Bergfeld, USSR Patent No. 511851. Published 25.04.76 in Bulletin of Invention No. 15
K. Amei, H. Eshghi, M. Bakavol, S. Rostamnia, Catal. Lett. 147, 491 (2016)
N. Mei, B. Liu, Int. J. Hydrog. Energy (2016). https://doi.org/10.1016/j.ijhydenc.2016.07.229
R.M. Magdalene, E.G. Leelamani, N.M.N. Gowda, J. Mol. Catal. A 223, 17 (2004)
M. Tian, C. Dong, Z. Dong, Appl. Surf. Sci. 390, 100 (2016)
P. Zhou, D. Li, S. Jin, S. Chen, Z. Zhang, Int. J. Hydrog. Energy (2016). https://doi.org/10.1016/j.ijhydenc.2016.07.257
P.F. Vogt, J.J. Gerulis, Amines, Aromatic. Ullmann’s Encyclopedia of Industrial Chemistry (Wiley, New York, 2000)
S.E. Kudaibergenov, G.S. Tatykhanova, A.N. Klivenko, J. Appl. Polym. Sci. (2016). https://doi.org/10.1002/app.43784
A.N. Klivenko, G.S. Tatykhanova, N. Nuraje, S. Kudaibergenov, Bull. Karaganda Univ. Ser. Chem. 4(80), 10 (2015)
G.S. Tatykhanova, A.N. Klivenko, G.M. Kudaibergenova, S.E. Kudaibergenov, Macromol. Symp. 363, 49 (2016)
M. Aldabergenov, М Dauletbekova, A. Shakhvorostov, G. Toleutay, A. Klivenko, S. Kudaibergenov, J. Chem. Technol. Metall. 53, 11 (2018)
A. Gainar, J.S. Stevens, E. Suljoti, J. Xiao, R. Golnak, E.F. Aziz, S.L.M. Schroeder, J. Phys. Conf. Ser. 712, 012034 (2016)
M. Muniz-Miranda, J. Anal. Bioanal. Tech. 6, 1 (2015)
P.G. Roth, R.S. Venkatachalam, F.J. Boerio, J. Chem. Phys. 85, 1150 (1986)
R.S. Venkatachalam, F.J. Boerio, P.G. Roth, J. Raman Spectrosc. 19, 281 (1988)
E.J. Liang, C. Engert, W. Kiefer, Vib. Spectrosc. 6, 79 (1993)
X.M. Yang, D.A. Tryk, K. Hashimoto, A. Fujishima, J. Phys. Chem. B 102, 4933 (1998)
X. Lili, F. Yan, Spectrochim. Acta A 61, 1991 (2005)
H. Park, S.B. Lee, K. Kim, M.S. Kim, J. Phys. Chem. 94, 7516 (1990)
J.W. Wang, W.N. Wang, Y. Fang, Vib. Spectrosc. 40, 197 (2006)
L.-B. Zhao, Y.-F. Huang, X.-M. Liu, J.R. Anema, D.-Y. Wu, B. Ren, Z.-Q. Tian, Phys. Chem. Chem. Phys. 14, 12919 (2012)
V.R.P. Verneker, B. Shahat, Macromolecules 19, 1851–1856 (1986)
Y. Shibasaki, Y. Abe, N. Sato, A. Fujimori, Y. Oishi, Polym. J. 42, 72 (2010)
S.E. Kudaibergenov Zh.E. Ibraeva, N.A. Dolya, B.Kh. Musabayeva, A.K. Zharmagambetova, J. Koetz. Macromol. Symp. 274, 11 (2008)
P. Veerakumar, M. Velayudham, K.-L. Lu, S. Rajagopal, Appl. Catal. A 439, 197 (2012)
D. Wu, Y. Zhang, M. Wen, H. Fang, Q. Wu, Inorg. Chem. (2017). https://doi.org/10.1021/acs.inorgchem.7b00304
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Financial support from the Ministry of Education and Science of the Republic of Kazakhstan (IRN AP05131003, 2018–2020) is greatly acknowledged.
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Kudaibergenov, S., Dauletbekova, M., Toleutay, G. et al. Hydrogenation of p-Nitrobenzoic Acid by Gold and Palladium Nanoparticles Immobilized Within Macroporous Amphoteric Cryogels in Aqueous Solution. J Inorg Organomet Polym 28, 2427–2438 (2018). https://doi.org/10.1007/s10904-018-0930-8
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DOI: https://doi.org/10.1007/s10904-018-0930-8
Keywords
- Macroporous amphoteric cryogel
- Palladium and gold nanoparticles
- Hydrogenation
- p-Nitrobenzoic acid
- Macroporous flow-through catalytic reactor