Control over Polymorph Formation of o-Aminobenzoic Acid

被引:54
作者
Jiang, Shanfeng [1 ]
Jansens, Pieter J. [1 ]
ter Horst, Joop H. [1 ]
机构
[1] Delft Univ Technol, Proc & Energy Dept, NL-2628 CA Delft, Netherlands
关键词
L-GLUTAMIC ACID; MEDIATED PHASE-TRANSFORMATIONS; SITU RAMAN-SPECTROSCOPY; ANTISOLVENT CRYSTALLIZATION; THERMODYNAMIC RULES; MOLECULAR-CRYSTALS; PHARMACEUTICALS;
D O I
10.1021/cg901257s
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Control over the polymorph formation requires thermodynamic and kinetic knowledge and in situ analytical techniques. In this study, the crystallization behavior of o-aminobenzoic acid (o-ABA) in batch cooling crystallization as well as the transformation behavior in solution was monitored in situ. Raman spectroscopy was used to analyze the polymorphic content of o-ABA. Form II was always obtained as the initial polymorph in the cooling crystallization at a cooling rate of 3.3 degrees C/min between 25 and 65 degrees C. Solvent-mediated transformations were performed in ethanol/water mixtures (X-v,X-w= 0.5) and in pure water at temperatures between 25 and 80 degrees C. It was clearly observed from solvent-mediated transformations that form I was stable below 50 degrees C, form III was stable above 50 degrees C, while form II was metastable at all investigated temperatures. Ultimately, an experiment was designed and performed, in which successively all pure polymorphs were present. Thus, control over polymorphism of o-ABA has been established.
引用
收藏
页码:2541 / 2547
页数:7
相关论文
共 20 条
[1]  
Bernstein J, 1999, ANGEW CHEM INT EDIT, V38, P3440, DOI 10.1002/(SICI)1521-3773(19991203)38:23<3440::AID-ANIE3440>3.0.CO
[2]  
2-#
[3]  
Bernstein J., 2020, Polymorphism in molecular crystals 2e, Vvol. 30
[4]   ANTHRANILIC ACIDII (ORTHO-AMINOBENZOIC ACID) [J].
BOONE, CDG ;
DERISSEN, JL ;
SCHOONE, JC .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1977, 33 (OCT) :3205-3206
[5]   ANTHRANILIC ACID-I, C7H7NO2, BY NEUTRON-DIFFRACTION [J].
BROWN, CJ ;
EHRENBERG, M .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1985, 41 (MAR) :441-443
[6]  
BURGER A, 1979, MIKROCHIM ACTA, V2, P273
[7]   POLYMORPHISM OF PHARMACEUTICALS AND OTHER MOLECULAR-CRYSTALS .1. THEORY OF THERMODYNAMIC RULES [J].
BURGER, A ;
RAMBERGER, R .
MIKROCHIMICA ACTA, 1979, 2 (3-4) :259-271
[8]   THE KINETICS OF SOLVENT-MEDIATED PHASE-TRANSFORMATIONS [J].
CARDEW, PT ;
DAVEY, RJ .
PROCEEDINGS OF THE ROYAL SOCIETY OF LONDON SERIES A-MATHEMATICAL PHYSICAL AND ENGINEERING SCIENCES, 1985, 398 (1815) :415-428
[9]  
Contineanu I, 2006, REV ROUM CHIM, V51, P323
[10]   RATE CONTROLLING PROCESSES IN SOLVENT-MEDIATED PHASE-TRANSFORMATIONS [J].
DAVEY, RJ ;
CARDEW, PT ;
MCEWAN, D ;
SADLER, DE .
JOURNAL OF CRYSTAL GROWTH, 1986, 79 (1-3) :648-653