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Synthesis and Quality Control of 3,3'-Diamino Diphenyl Sulfone by High Performance Liquid Chromatography
Corresponding Author(s) : Hong-Zhen Lian
Asian Journal of Chemistry,
Vol. 26 No. 16 (2014): Vol 26 Issue 16
Abstract
An effective reversed-phase high performance liquid chromatographic method has been developed to separate industrial 3,3'-diamino diphenyl sulfone and its related substances. Separation was achieved on a reversed-phase C18 column with methanol-water (40/60, v/v) as the mobile phase and detection was operated by UV absorption at a wavelength of 250 nm. One unknown impurity, 3,4'-diamino diphenyl sulfone, was identified by the combination of liquid chromatography-mass spectrometry and relationship between RP-HPLC retention and hydrophobicity of the compounds studied. Partial related impurities, 4,4'-diamino diphenyl sulfone, 3,4'-diamino diphenyl sulfone and 3-amino-3'-nitro diphenyl sulfone were determined under the proposed chromatographic condition with relative standard deviations lower than 4.4 %. On the basis of good separation and reliable determination of related substances in 3,3'-diamino diphenyl sulfone, the chromatographic fingerprint of industrial 3,3'-diamino diphenyl sulfone was established, by which quality assessment of 3,3'-diamino diphenyl sulfone could be facilitated for industrial use.
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- G. Cao, Fine Chem. Ind. Inf., 4, 40 (1988).
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- B.R. Baker, A.F. Kadish and M.V. Querry, J. Org. Chem., 15, 400 (1950); doi:10.1021/jo01148a027.
- S.D. Qi, S.C. Zhu and X.Q. Zhu, CN200810054709.4 (2008).
- F.S. Li, H.B. Zhang and W. Yao, CN200910183449.5 (2010).
- R.W. Lv, Z.X. Zhang, Q.S. Shi, H. Zhou and D. Liang, Dyestuffs Color., 42, 43 (2005).
- H.Z. Lian, Fine Chem. Intermed., 34, 1 (2004).
- H.Z. Lian and Y.N. Wei, Talanta, 71, 264 (2007); doi:10.1016/j.talanta.2006.03.054.
- Y.N. Wei, C. Li and H.Z. Lian, Rock Min. Anal., 26, 81 (2007).
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- Q. Xie, W, Yao and F.S. Li, J. Nanjing Univ. Technol. (Nat. Sci. Ed.), 31, 86 (2009).
- http://www.polysciences.com/catalog/department/product/98/categoryid--266/productid--1256/.
References
G. Cao, Fine Chem. Ind. Inf., 4, 40 (1988).
T.H. Sun, Chem. Ind. Times, 5, 32 (1999).
S.H. Lu, G.L. Yuan and S.D. Qi, Chem. Ind., 39, 115 (2012).
Y. Qian, C.B. Huang, Q.P. Ding, C.L. Lai, S.L. Chen and F. Chen, Polym. Mater. Sci. Eng., 22, 42 (2006).
A. Rajagopalan, R. Rajagopal and S. Seshadri, Dyes Pigments, 9, 209 (1988); doi:10.1016/0143-7208(88)85010-1.
A. Mahroug, M. Belhouchet and T. Mhiri, Phosphorus Sulfur Silicon Rel. Elem., 187, 1482 (2012); doi:10.1080/10426507.2012.690119.
B.R. Baker, A.F. Kadish and M.V. Querry, J. Org. Chem., 15, 400 (1950); doi:10.1021/jo01148a027.
S.D. Qi, S.C. Zhu and X.Q. Zhu, CN200810054709.4 (2008).
F.S. Li, H.B. Zhang and W. Yao, CN200910183449.5 (2010).
R.W. Lv, Z.X. Zhang, Q.S. Shi, H. Zhou and D. Liang, Dyestuffs Color., 42, 43 (2005).
H.Z. Lian, Fine Chem. Intermed., 34, 1 (2004).
H.Z. Lian and Y.N. Wei, Talanta, 71, 264 (2007); doi:10.1016/j.talanta.2006.03.054.
Y.N. Wei, C. Li and H.Z. Lian, Rock Min. Anal., 26, 81 (2007).
J.Q. Qiao, D. Sheng and H.Z. Lian, Talanta, 77, 1573 (2009); doi:10.1016/j.talanta.2008.09.048.
Q. Xie, W, Yao and F.S. Li, J. Nanjing Univ. Technol. (Nat. Sci. Ed.), 31, 86 (2009).
http://www.polysciences.com/catalog/department/product/98/categoryid--266/productid--1256/.