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http://dx.doi.org/10.14478/ace.2017.1016

Development of New Fluorescent Whitening Agent with 4,4'-Di((E)-styryl)-1,1'-biphenyl Skeleton from Recyclable Source MFB  

Chung, Hyun Ju (Department of Applied Chemistry, Kookmin University)
Yang, Yun Seung (Department of Applied Chemistry, Kookmin University)
Kim, Seok Chan (Department of Applied Chemistry, Kookmin University)
Publication Information
Applied Chemistry for Engineering / v.28, no.3, 2017 , pp. 294-298 More about this Journal
Abstract
Six new fluorescent whitening agent's candidates with 4,4'-di((E)-styryl)-1,1'-biphenyl skeleton which is the same as that of Uvitex FP family were synthesized using methyl 4-formylbenzoate (MFB) as a starting material. MFB has been disposed as a by-product of dimethyl terephthalate (DMT) production process. Six candidates were synthesized by the reaction of MFB, and its derivatives with tetraethyl biphenyl-4,4'-diylbis(methylene)diphosphonate (3) using Wittig-Horner reaction. A series of UV spectra were recorded and the results were used for estimating molar absorptivities of each candidates in order to find their potential application as fluorescent whitening agents. Considering the molar absorptivity (log ${\varepsilon}$ 3.95~2.60) for all candidates was lower than that of the commercial Uvitex FP 127 (log ${\varepsilon}$ 4.85), it was concluded that they are not suitable for fluorescent whitening agent applications.
Keywords
methyl 4-formylbenzoate; recyclable source; DMT; fluorescent whitening agent; 4,4'-di((E)-styryl)-1,1'-biphenyl skeleton;
Citations & Related Records
Times Cited By KSCI : 4  (Citation Analysis)
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1 A. H. Ford-Moore and B. J. Perry, Diisopropyl methylphosphonate, Org. Synth. Coll. Collect., 4, 325-327 (1963).
2 R. J. Sundberg, P. A. Buckowork, and F. O. Holcombe, Preparation of esters of 4-alkyl-2,4-pentadienoic acids by the phosphonate modification of the Wittig reaction, J. Org. Chem., 32, 2938-2941 (1967).
3 H. Pommer, H. P. Siebel, R. Schwen, and W. Stilz, Macromolecular substances optically brightened with 1,4-bis-styryl-benzenes, US Patent 3,177,153 (1965).
4 W. Stilz and H. Pommer, Production of compounds of the 1,4-divinylbenzene series, US Patent 3,177,208 (1965).
5 A. R. Mitchell, P. F. Pagoria, and R. D. Schmidt, A new synthesis of TATB using inexpensive starting materials and mild reaction conditions, 27th International Annual Conference ICT on Energetic Materials. June 25-28, Karlsruhe, Germany (1996).
6 A. R. Mitchell, P. F. Pagoria, and R. D. Schmidt, New synthesis of TATB process development studies, 29th International Annual Conference ICT on Energetic Materials. June 30-July 3, Karlsruhe, Germany (1998).
7 K. D. Kim, Y. Yu, H. J. Jeong, M. J. Ham, K. L. Kim, A. N. Kim, O. Davgajantsan, G. S. Park, and S. C. Kim, Development on recovery of MFB from industrial waste without second pollution, Bull. Korean Chem. Soc., 33, 4275-4276 (2012).   DOI
8 Y. Ryu, J. C. Kim, M. J. Ham, and S. C. Kim, Process development of 4,4'-bis(2-benzoxazolyl)stilbene from recyclable source MFB, Appl. Chem. Eng., 27, 195-198 (2016).   DOI
9 S. H. Kim, Y. Ryu, J. C. Kim, and S. C. Kim, Recovery of MFB generated from dimethyl terephthalate production process, Appl. Chem. Eng., 26, 621-623 (2015).   DOI
10 K. D. Kim, Y. Ryu, and S. C. Kim, Facile one-pot synthesis of PABA from MFB, Appl. Chem. Eng., 25, 337-339 (2014).   DOI
11 J. C. Kim, Y. Ryu, and S. C. Kim, Practical process development of AMCA from recyclable source MFB, Appl. Chem. Eng., 27, 508-511 (2016).   DOI
12 K. Weber and C. Luethi, Styryl compounds, process for their manufacture and their use, US Patent 3,825,534 (1974).
13 A. E. Siegrist, P. Liechti, H. R. Meyer, and K. Weber, Aromatic compounds containing ethylene double bonds, processes for their manufacture and use, US Patent 3,991,049 (1976).
14 L. Guglielmetti, H. R. Meyer, D. Reinehr, and K. Weber, Mixtures of fluorescent whitening agents, US Patent 4,867,906 (1989).