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Chemical Structure| 5056-07-5 Chemical Structure| 5056-07-5

Structure of 5056-07-5

Chemical Structure| 5056-07-5

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Mruc, Patrycja ; Antos, Dorota ;

Abstract: Chiral chromatography (CCh) is often a cost driver in the large-scale separation of enantiomers. To improve the economics of the separation process, we developed the concept of coupling CCh with achiral chromatography (ACh). In this concept, the CCh step is used to enrich the enantiomeric mixture with the target enantiomer, while in the ACh step, the enriched mixture is separated to obtain the product with a desired purity. The ACh separation is driven by the phenomenon of self-disproportionation of enantiomers (SDE), which relies on formation of homochiral and heterochiral associates that can be separated in an achiral environment, whereas the CCh separation occurs in the presence of a chiral stationary phase (CSP). The coupled ACh-CCh process is operated in a cyclic mode for which cyclic steady state is attained. To demonstrate the concept of the process and develop a generic methodology for its design, a model mixture consisting of enantiomers of methyl p-tolyl sulfoxide was used, with S-p-tolyl sulfoxide as the target enantiomer. For both ACh and CCh, the influence of the operating variables, including mobile phase composition, loading density, and enantiomeric excess (ee) of the feed mixture, on the separation performance was examined. On the basis of the experimental data, a dynamic model was formulated, calibrated, and used to support the process design and assess the performance of both the standalone ACh and CCh as well as their coupling in various configurations. The amount of product obtained in a single cycle of ACh-CCh was markedly higher compared to that obtained in the standalone CCh, which provided the benefit of reducing consumption of the costly CSP. This benefit was enhanced with increasing ee of the feed mixture. For example, for racemic mixtures, the mass of the product per cycle of ACh-CCh was 1.5 times higher, for mixtures with ee = 70% it was 4 times higher, and for mixtures with ee = 85% it was 5.7 times higher compared to the standalone CCh. Furthermore, for mixtures with a high ee, a marked improvement in process productivity was obtained, e.g., for mixtures with ee = 70%, the productivity of ACh-CCh was twice higher, for ee = 85% it was 2.5 times higher compared to the standalone CCh.

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Patrycja Mruc ; Maksymilian Olbrycht ; Markiian Korbetskyy ; Dorota Antos ;

Abstract: The influence of mobile phase composition on the efficiency of enantiomer separation by achiral chromatography (ACh) was investigated. The separation was induced by the phenomenon of self-disproportionation of enantiomers (SDE) triggered by their homo and hetero-chiral interactions in an achiral environment. Typically, SDE occurs in apolar mobile phases of weak elution strength, which causes the separation time to extend and the process productivity to deteriorate. To mitigate that effect, we altered the content of a strong solvent (modifier) in the mobile phase by use of a solvent gradient in which the target enantiomer was separated in the presence of the weak solvent, whereas the unresolved mixture of enantiomers was eluted by increasing the modifier content in the mobile phase. This enabled accelerating the solute elution while preserving the separation selectivity. The approach was examined for the separation of nonracemic mixtures of two structurally different compounds that exhibited the SDE effect in ACh, i.e., metalaxyl (MX) and methyl p-tolyl sulfoxide (MTSO). The target compound of the separation was the more abundant enantiomer in the enantiomeric mixture. The process realization was preceded by the determination of the effect of the modifier content on the separation yield for enantiomeric mixtures of MX and MTSO of different enantiomeric excess (ee). In the case of MX, yield of the pure target enantiomer varied from 2 %, for the maximum concentration of the modifier, to 45 % for the minimum modifier concentration and the largest ee used in the experiments. In the case of MTSO, the yield varied from minimum 40 % to maximum 66 %. To predict the process, we employed a dynamic model, in which underlying thermodynamic dependencies were implemented.

Keywords: Enantiomer separation ; Achiral chromatography ; Gradient elution ; Self-disproportion ; Thermodynamics

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Product Details of [ 5056-07-5 ]

CAS No. :5056-07-5
Formula : C8H10OS
M.W : 154.23
SMILES Code : O=[S@@](C)C1=CC=C(C)C=C1
MDL No. :MFCD00151503
InChI Key :FEVALTJSQBFLEU-JTQLQIEISA-N
Pubchem ID :11170275

Safety of [ 5056-07-5 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H315-H318-H335
Precautionary Statements:P261-P264-P271-P280-P280-P302+P352-P304+P340+P312-P305+P351+P338+P310-P332+P313-P362+P364-P403+P233-P405-P501
Class:8
UN#:1759
Packing Group:

Application In Synthesis of [ 5056-07-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 5056-07-5 ]

[ 5056-07-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 25415-67-2 ]
  • [ 5056-07-5 ]
  • [ 113002-37-2 ]
  • 2
  • [ 383-62-0 ]
  • [ 5056-07-5 ]
  • [ 121898-05-3 ]
  • [ 133343-42-7 ]
  • 3
  • [ 383-62-0 ]
  • [ 5056-07-5 ]
  • [ 132164-16-0 ]
  • [ 133343-49-4 ]
 

Historical Records

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[ 5056-07-5 ]

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Reason: Optical isomers