Binary phase diagrams between phenanthrene and two of its impurities: 9,10-dihydroanthracene and carbazole

Burel, Antoine; Couvrat, Nicolas; Tisse, Séverine; Cartigny, Yohann; Cardinaël, Pascal; Coquerel, Gérard

doi:10.1140/epjst/e2016-60270-0

Cited by 7 publications

(8 citation statements)

References 13 publications

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“… 33 Ineffective purification of phenanthrene in the presence of impurity 9,10-dihydroanthracene by crystallization due to partial solid-solution formation between the components was demonstrated by analysis of the binary phase diagrams. 34 Partial miscibility between a pair of α- and β-epimers (2.6% for α in β and 4.4% for the reverse) was revealed by construction of binary phase diagrams and subsequent Tammann triangle plots. 35 When considering the purity required for crystalline API compounds, such low levels of miscibility could pose an issue to the purification process.…”

Section: Impurities In Crystallizationmentioning

confidence: 99%

“…Such solid-state miscibility, whereby the impurity is thermodynamically substituted irregularly into the crystal lattice due to structurally similarity, is characterized by a distribution of the impurity throughout bulk crystal material. , The even distribution of the impurity paracetamol in phenacetin crystals was shown by stepwise dissolution of large single crystals, which is hypothesized to be due to formation of a solid solution . Ineffective purification of phenanthrene in the presence of impurity 9,10-dihydroanthracene by crystallization due to partial solid-solution formation between the components was demonstrated by analysis of the binary phase diagrams . Partial miscibility between a pair of α- and β-epimers (2.6% for α in β and 4.4% for the reverse) was revealed by construction of binary phase diagrams and subsequent Tammann triangle plots .…”

Section: Impurities In Crystallizationmentioning

confidence: 99%

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A Structured Approach To Cope with Impurities during Industrial Crystallization Development

Urwin

Levilain

Marziano

et al. 2020

Org. Process Res. Dev.

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The perfect separation with optimal productivity, yield, and purity is very difficult to achieve. Despite its high selectivity, in crystallization unwanted impurities routinely contaminate a crystallization product. Awareness of the mechanism by which the impurity incorporates is key to understanding how to achieve crystals of higher purity. Here, we present a general workflow which can rapidly identify the mechanism of impurity incorporation responsible for poor impurity rejection during a crystallization. A series of four general experiments using standard laboratory instrumentation is required for successful discrimination between incorporation mechanisms. The workflow is demonstrated using four examples of active pharmaceutical ingredients contaminated with structurally related organic impurities. Application of this workflow allows a targeted problem-solving approach to the management of impurities during industrial crystallization development, while also decreasing resources expended on process development.

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Section: Impurities In Crystallizationmentioning

confidence: 99%

Section: Impurities In Crystallizationmentioning

confidence: 99%

A Structured Approach To Cope with Impurities during Industrial Crystallization Development

Urwin

Levilain

Marziano

et al. 2020

Org. Process Res. Dev.

View full text Add to dashboard Cite

show abstract

“…However, some solid solutions have been observed in systems with structurally similar impurities. 53,[55][56][57][58][59][60] Similarly, it is important to note that impurities may form co-crystals with the solute system under the appropriate crystallization conditions. These are homogenous crystalline structures comprising a neutral co-former and a neutral target held together by a non-covalent interactive bond.…”

Section: Impurity Incorporation In Solution Crystallizationmentioning

confidence: 99%

“…However, some solid solutions have been observed in systems with structurally similar impurities. 53,55–60…”

Section: Impurity Incorporation In Solution Crystallizationmentioning

confidence: 99%

Impurity incorporation in solution crystallization: diagnosis, prevention, and control

2022

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“…An example is the binary phase diagrams of 9,10-dihydroanthracene and carbazole with phenanthrene [33].…”

mentioning

confidence: 99%

Phase equilibria and their applications

Rietveld

2017

Eur. Phys. J. Spec. Top.

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This special issue on phase behavior was instigated by the successful JEEP (Journées d'Étude desÉquilibres entre Phases) meeting in March 2016 in Paris. The meeting is held yearly for over forty years and was established by a group of French researchers back in the seventies working on phase equilibria. It explains why its name is French even if the working language during the conference is nowadays English, as a large community from different countries participates (which has led to the proposition to call the conference 'Joint European days on Equilibria between Phases'). This special issue is not the proceedings of the conference, but it does demonstrate the vast research area in which phase equilibria are of importance.Phase behavior can appear as something magical. To take a simple example, the freezing or melting of water occurs at constant temperature, which means that mixtures of water and ice can be used to control temperature very accurately. In first instance, and possibly even after one understands thermodynamics, this can appear a miracle.An interesting question related to phase behavior is for example the preferential formation of one form of calcium carbonate by shellfish, whereas a more stable form of calcium carbonate exists. How could this happen? How does the animal control the formation of a less stable form? How can the animal prevent the interconversion into the more stable form? Similar questions exist in the pharmaceutical realm, where formulators need to ascertain the stability of a drug formulation, consisting for example of a powder, a tablet, or a suspension. A patient expects that his or her drug will work even after it has been stored on a shelf in the bathroom for over a year. This requires understanding of the solid-state behavior of drugs and mixtures of drugs and their sensitivity to water. Therefore, the FDA (Food and Drug Administration) and EMA (European Medicine Agency) require the pharmaceutical industry to prove that they can maintain their formulation for a given period of time.Similar questions exist for metal tools in industry used under high pressure, strain, and high temperatures. Machinery cannot fail when working under demanding circumstances, as it can cause dangerous situations and it will result in loss of material and profit. Another interesting issue is the taste and mouth feel of chocolate, which highly depends on the proper crystal form of the cocoa butter. It possesses several different crystal structures, and the most sought after form melts just above 30• C in a

show abstract

Binary phase diagrams between phenanthrene and two of its impurities: 9,10-dihydroanthracene and carbazole

Cited by 7 publications

References 13 publications

A Structured Approach To Cope with Impurities during Industrial Crystallization Development

A Structured Approach To Cope with Impurities during Industrial Crystallization Development

Impurity incorporation in solution crystallization: diagnosis, prevention, and control

Phase equilibria and their applications

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