Influence of solvent choice on the optimisation of a reaction–separation operation: application to a Beckmann rearrangement reaction

Elgue, Sébastien; Prat, Laurent E.; Cognet, Patrick; Cabassud, Michel; Lann, J.M. Le; Cezerac, J.

doi:10.1016/s1383-5866(03)00200-4

Cited by 15 publications

(9 citation statements)

References 10 publications

(11 reference statements)

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“…Despite an extensive literature describing solvent issues, , solventless reactions, − nontraditional solvents, − and process considerations for good solvent selection, − it is fair to say that chemists responsible for the earliest synthesis of compounds used in drug discovery activities do not consider solvent selection. This situation is somewhat perplexing, given the attention that solvents and solvent use have been given at various symposia and conferences over the past 10 years or more.…”

Section: Introductionmentioning

confidence: 99%

Perspective on Solvent Use in the Pharmaceutical Industry

Constable

Jimenez-Gonzalez

Henderson

2006

Org. Process Res. Dev.

604

439

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Solvent use consistently accounts for between 80 and 90% of mass utilization in a typical pharmaceutical/fine chemicals (nonpolymer) batch chemical operation. Moreover, within these operations, solvents play a dominant role in the overall toxicity profile of any given process; i.e. on a mass basis, solvents account for the largest proportion of chemicals of concern used in the process. However, for the typical synthetic organic chemist, solvents are just a medium in which a reaction takes place; the interest is in the reactivity and building of a molecule, not in the means by which this is carried out. So, in a typical retrosynthetic analysis, solvent and solvent-reactant interactions, separability, and particle engineering are generally not included. The best means in which this reaction can take place is also not considered; i.e., the reaction space, configuration, order of addition, heat/mass transfer, etc., is generally not considered. This publication presents a case for greater awareness of solvent issues in batch chemical operations typically found in the pharmaceutical industry.

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Section: Introductionmentioning

confidence: 99%

Perspective on Solvent Use in the Pharmaceutical Industry

Constable

Jimenez-Gonzalez

Henderson

2006

Org. Process Res. Dev.

604

439

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“…The choice of the reaction solvent then results from a compromise between reaction performances and separation facilities. Recent works [12] allow to assess the benefits related to such design in the context of the pharmaceutical industry.…”

Section: Resultsmentioning

confidence: 99%

Optimisation of solvent replacement procedures according to economic and environmental criteria

Elgue

Prat

Cabassud

et al. 2006

Chemical Engineering Journal

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“…Some tools have been established and further developed to tolerate fewer argumentative processes [15][16][17][18][19][20][21][22][23], such as choosing of solvents considering environmental, health and safety feature as well as the life cycle assessment (LCA) and economic measure. Kralisch and co-workers [24,25] evaluated and optimized an approach considering ecological and economic aspects of the production of some reactants and solvents used in synthesis, workup, recycling and disposal.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin- 2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics

Gilbile¹,

Bhavani²,

Vyas³

2017

Asian J. Chem.

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A modified synthesis of methyl 3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate (halosulphuron) is described. The merits of the synthesis are (i) one pot chlorination of methyl 1-methyl-1H-pyrazole-4-carboxylate (1) in presence of sulphuryl chloride resulting in methyl 3,5-dichloro-1-methyl-1H-pyrazole-4-carboxylate (2) (ii) conversion of 3-chloro-5-mercapto-1-methyl-1H-pyrazole-4-carboxylate (3) to 3-chloro-1-methyl-5-sulfamoyl pyrazole-4-carboxylate (4) under mild reaction conditions utilizing tetrabutyl ammonium chloride, N-chlorosuccinimide and ammonium carbonate (iii) condensation of sulphonamide (4) with carbamate (6) by microwave irradiation. Efforts were made to calculate, atom economy, reaction mass efficiency and E-factor for all the reaction steps involved in the synthesis of halosulfuron. The E-factor values in step 2 and step 4 reaction is lower, indicating that these reactions are greener (generation of less waste) when compared to the remaining steps in the synthesis.

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Influence of solvent choice on the optimisation of a reaction–separation operation: application to a Beckmann rearrangement reaction

Cited by 15 publications

References 10 publications

Perspective on Solvent Use in the Pharmaceutical Industry

Perspective on Solvent Use in the Pharmaceutical Industry

Optimisation of solvent replacement procedures according to economic and environmental criteria

Evaluation of Synthesis of Methyl 3-Chloro-5-(4,6-dimethoxypyrimidin- 2-ylcarbamoylsulfamoyl)-1-methylpyrazole-4-carboxylate Using Green Metrics

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