Abstract
The synthesis process of 3,5-diamino-1,2,4-triazole (DAT) was investigated by on-line attenuated total reflection infrared (ATR-IR) spectroscopy combined with advanced chemometrics method. The principal component analysis (PCA) was used to analyze the IR spectra matrix, which was in order to obtain orthonormal column and the number of principal components. Then the pure IR spectrum of every substance was obtained by mutual information least dependent component analysis (MILCA). The possible synthesis mechanism of DAT was deducted based on the changes of functional groups in the IR spectra. The geometric configurations of intermediates were optimized with the density functional theory (DFT) at B3LYP/6-311G*(d, p) level, and the vibrational frequencies were calculated simultaneously. The results by MILCA method agree well with quantum chemical calculation method, thus which demonstrated the reliability of MILCA. The present study proves that on-line ATR-IR spectroscopy combined with advanced chemometrics method can be applied to study the chemical synthesis mechanism and provide a strong technical support for the research and development of process analytical technology (PAT).
Similar content being viewed by others
References
X. Deng, J. Wang, J. Zhang, T. Sim, N.D. Kim, T. Sasaki, W. LutherII, R.E. George, P.A. Jänne, N.S. Gray, ACS Med. Chem. Lett. 2, 379 (2011)
O. Bekircan, M. Küxük, B. Kahveci, S. Kolaylı, Arch. Pharm. 338, 365 (2005)
Y. Ren, W. Li, F. Zhao, J. Yi, B. Yan, H. Ma, K. Xu, J. Song, R. Hu, J. Anal. Appl. Pyrolysis 102, 89 (2013)
V. Thottempudi, H. Gao, J.M. Shreeve, J. Am. Chem. Soc. 133, 6464 (2011)
F.R. Brushett, M.S. Thorum, N.S. Lioutas, M.S. Naughton, C. Tornow, H. Jhong, A.A. Gewirth, P.J.A. Kenis, J. Am. Chem. Soc. 132, 12185 (2010)
K.G. Schmitt, A.A. Gewirth, J. Phys. Chem. C 118, 17567 (2014)
M.S. Thorum, J. Yadav, A.A. Gewirth, Angew. Chem. Int. Ed. 48, 165 (2009)
J. Hernández-Gil, N. Ovèjak, S. Ferrer, F. Lloret, A. Castiñeiras, Inorg. Chem. 52, 2289 (2013)
I. Matulková, J. Cihelka, M. Pojarová, K. Fejfarová, M. Dušek, P. Vaněk, J. Kroupa, R. Krupková, J. Fábry, I. Němec, CrystEngComm 14, 4625 (2012)
X. Liu, Z. Su, W. Ji, S. Chen, Q. Wei, G. Xie, X. Yang, S. Gao, J. Phys. Chem. C 118, 23487 (2014)
Z. Su, X. Liu, Q. Yang, S. Zhang, Q. Wei, G. Xie, S. Chen, S. Gao, CrystEngComm 16, 4245 (2014)
M.B. Frankel, E.A. Burns, J.C. Butler, E.R. Wilson, J. Org. Chem. 28, 2428 (1963)
D.W. Kaiser, J.J. Roemer, Preparation of guanazole: U.S. Patent 2, 648 (1953)
B. Wang, S. Jia, X. Wang, H. Zhang, Q. Liu, Chem. Reag. 29, 563 (2007)
A.E. Rubin, S. Tummala, D.A. Both, C. Wang, E.J. Delaney, Chem. Rev. 106, 2794 (2006)
A. Horváth, K.D. Smet, D. Ormerod, D. Depré, C. Pérez-Balado, T. Govaerts, D.V. Heuvel, I. Schorpion, Org. Process Res. Dev. 9, 356 (2005)
M. Palucki, Z. Lin, Y. Sun, Org. Process Res. Dev. 9, 141 (2005)
K. Pöllänen, A. Häkkinen, S. Reinikainen, J. Rantanen, M. Karjalainen, M. Louhi-Kultanen, L. Nyström, J. Pharm. Biomed. Anal. 38, 275 (2005)
R.J. Pell, X. Chen, J. Chemom. 28, 411 (2014)
D. Lumpi, C. Wagner, M. Schöpf, E. Horkel, G. Ramer, B. Lendl, J. Fröhlich, Chem. Commun. 48, 2451 (2012)
Z. Lin, L. Zhou, A. Mahajan, S. Song, T. Wang, Z. Ge, D. Ellison, J. Pharm. Biomed. Anal. 41, 99 (2006)
B.M. Wise, N.B. Gallagher, J. Process Control 6, 329 (1996)
N. Wu, K. Sun, Y. Liu, X. Yang, H. Li, Chem. Res. Chin. Univ. 29, 759 (2013)
M. Garrido, F.X. Rius, M.S. Larrechi, Anal. Bioanal. Chem. 390, 2059 (2008)
H. Li, J. Gao, H. Tang, J. Li, T. Zhang, X. Yang, Anal. Methods 7, 4152 (2015)
J. Li, J. Gao, H. Li, X. Yang, Y. Liu, Anal. Methods 6, 4305 (2014)
A. Hyvärinen, E. Oja, Neural Netw. 13, 411 (2000)
J. Onton, M. Westerfield, J. Townsend, S. Makeig, Neurosci. Biobehav. Rev. 30, 808 (2006)
D.J.R. Bouveresse, A. Moya-González, F. Ammari, D.N. Rutledge, Chemom. Intell. Lab. Syst. 112, 24 (2005)
S.A. Astakhov, H. Stögbauer, A. Kraskov, P. Grassberger, ArXiv Preprint Physics 0412029 (2004)
A. Kraskov, H. Stögbauer, P. Grassberger, Phys. Rev. E 69, 066138 (2004)
H. Stögbauer, A. Kraskov, S.A. Astakhov, P. Grassberger, Phys. Rev. E 70, 066123 (2004)
H. Parastar, M. Jalali-Heravi, R. Tauler, TrAC Trends Anal. Chem. 31, 134 (2012)
P. Hadi, Analyst 139, 2574 (2014)
Y.B. Monakhova, A.M. Tsikin, S.P. Mushtakova, M. Mecozzi, Microchem. J. 118, 211 (2015)
Y.B. Monakhova, T. Kuballa, J. Leitz, D.W. Lachenmeier, Int. J. Anal. Chem. 2011, 704795 (2011)
S. Chakraborty, J. Bartussek, S.N. Fry, M. Zapotocky, PLoS ONE 10, e0116813 (2015)
H. Shen, X. Li, Y. Liang, Chin. Sci. Bull. 45, 1368 (2000)
A.P. Scott, L. Radom, J. Phys. Chem. 100, 16502 (1996)
P.R. Griffiths, J.A. De Haseth, Fourier Transform Infrared Spectrometry (Wiley, New York, 2007)
H.A. Willis, J.H. Van der Maas, R.G.J. Miller, Laboratory Methods in Vibrational Spectroscopy (Wiley, New York, 1987)
http://www.ucl.ac.uk/ion/departments/sobell/Research/RLemon/MILCA/MILCA
M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Jr, T. Montgomery, K.N. Vreven, J.C. Kudin, J.M. Burant, S.S. Millam, J. Iyengar, V. Tomasi, B. Barone, M. Mennucci, G. Cossi, N. Scalmani, G.A. Rega, H. Petersson, M. Nakatsuji, M. Hada, K. Ehara, R. Toyota, J. Fukuda, M. Hasegawa, T. Ishida, Y. Nakajima, O. Honda, H. Kitao, M. Nakai, X. Klene, J.E. Li, H.P. Knox, J.B. Hratchian, C. Cross, J. Adamo, R. Jaramillo, R.E. Gomperts, O. Stratmann, A.J. Yazyev, R. Austin, C. Cammi, J.W. Pomelli, P.Y. Ochter-ski, K. Ayala, G.A. Morokuma, P. Voth, J.J. Sal-vador, G. Dannenberg, S. Zakrzewski, A.D. Dapprich, M.C. Daniels, O. Strain, D.K. Farkas, A.D. Malick, K. Rabuck, J.B. Raghavachari, J.V. Foresman, Q. Ortiz, A.G. Cui, S. Baboul, J. Clifford, B.B. Cioslowski, G. Stefanov, A. Liu, P. Liashenko, I. Piskorz, R.L. Komaromi, D.J. Martin, T. Fox, M.A. Keith, C.Y. Al-Laham, A. Peng, M. Nanayakkara, P.M.W. Challacombe, B. Gill, W. Johnson, M.W. Chen, C. Wong, J.A.Pople Gonzalez, Gaussian 03, Revision D.01 (Gaussian Inc, Wallingford CT, 2004)
Acknowledgements
The work was financially supported by National Natural Science Foundation of China (No. 21175106, 21375105) and the Specialized Research Fund for the Doctoral Program of Higher Education (No. 20126101110019).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Ma, J., Gao, X., Qi, J. et al. On-line attenuated total reflection infrared (ATR-IR) spectroscopy combined with advanced chemometrics for investigating the synthesis process of 3,5-diamino-1,2,4-triazole. J IRAN CHEM SOC 14, 915–923 (2017). https://doi.org/10.1007/s13738-016-1040-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-016-1040-6