Polymorphism and crystal transformation of penicillin sulfoxide

doi:10.1007/s11705-011-1140-x

Front Chem Sci Eng

2011, Vol. 5

Issue (4) : 442-447 https://doi.org/10.1007/s11705-011-1140-x

RESEARCH ARTICLE

Polymorphism and crystal transformation of penicillin sulfoxide

Dingding JING, Yongli WANG, Zhijian CHEN(

), Lina ZHOU, Jingkang WANG(

)

State Key Laboratory for Chemical Engineering, School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, China

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Abstract

Penicillin sulfoxide is the intermediate for the synthesis of 7-amino-3-desacetoxycephalosporanic acid which is one of the most important nucleuses of cephalosporin antibiotic. In this contribution, two crystal structures of penicillin sulfoxide (forms I and II) were determined by X-ray diffraction, and their thermotropic properties were investigated by differential scanning calorimetry (DSC). Furthermore, the transformation of form II to form I was studied quantitatively by Raman spectroscopy, and its rates at different temperatures were determined. The results indicate that penicillin sulfoxide is more stable as form I, and the temperature plays an important role in the crystal transformation.

Keywords penicillin sulfoxide crystallization polymorphism crystal transformation Raman spectroscopy

Corresponding Author(s): CHEN Zhijian,Email:zjchen@tju.edu.cn; WANG Jingkang,Email:wangjkch@tju.edu.cn

Issue Date: 05 December 2011

Cite this article:

Dingding JING,Yongli WANG,Zhijian CHEN, et al. Polymorphism and crystal transformation of penicillin sulfoxide[J]. Front Chem Sci Eng, 2011, 5(4): 442-447.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-011-1140-x
https://academic.hep.com.cn/fcse/EN/Y2011/V5/I4/442

Fig.1 The chemical structure of penicillin sulfoxide

Fig.2 The diffraction patterns of penicillin sulfoxide samples prepared by crystallization methods I and II

Tab.1 The data of crystal forms I and II for penicillin sulfoxide

Fig.3 The molecular structures of penicillin sulfoxide in crystal form I (A) and two associated molecules of penicillin sulfoxide in crystal form II (B). The oxygen atoms of water molecules in crystal form II are labeled as OW1, OW2 and OW3

Fig.4 The crystal packing of penicillin sulfoxide crystal form I projected on plane (A) and crystal form II projected on plane (B). The water molecules are shown as black spots

Fig.5 The DSC curves of penicillin sulfoxide (heating rate: 10 K/min)

Fig.6 The Raman spectra of penicillin sulfoxide obtained from the dry mixture of forms I and II (A). Calibration line for the concentration of form I in the mixture of forms I and II of penicillin sulfoxide (B). The mass fraction of crystal form I is (a) 0%, (b) 10.1%, (c) 20.2%, (d) 29.6%, (e) 39.3%, (f) 50.0%, (g) 59.9%, (h) 69.1%, (i) 79.8%, (j) 88.6%, (k) 100%. The arrows indicate the changes of the relative intensity upon increasing the mass fraction of crystal form I

Fig.7 (A) The concentration profiles of form I of penicillin sulfoxide during the crystal transformation process at 40°C. (B) Temperature dependence of crystal transformation rate of penicillin sulfoxide.

Fig.8 The record curves of online Raman spectra peak at 1193.4 cm and 1204.4 cm at 40°C. The wave lines are acquired from online Raman analysis and the thick line are the fitted lines using moving-average method

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