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Another route to obtain pyrazolidine passing through the synthesis of 1 and 2-pyrazoline by intramolecular Raschig way

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Abstract

Another route to obtain pyrazolidine was developed. It consists of a three step mechanism, which involves, first, the sequential formation of N,N′-dichloro-1,3-diaminopropane starting from 1,3-diaminopropane and sodium hypochlorite, second, a dehydrohalogenation of the dichloro derivative leading to 1-pyrazoline and 2-pyrazoline and finally, the hydrogenation of these two derivatives in order to obtain the compound of interest. In this paper, our study was focused on the kinetics of the formation of 1-pyrazoline and 2-pyrazoline. A kinetic model was proposed and then validated by experimental results. A quantum calculation (Gaussian09/CBS-QB3) was performed in order to determine the stability of the 1 and 2-pyrazolines. It showed that the 2-pyrazoline is more stable than the 1-pyrazoline. This process has been validated on the ISOCHEM production site.

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Authors and Affiliations

  1. Université Claude Bernard Lyon 1, Laboratoire Hydrazines et Composés Energétiques Polyazotés – UMR 5278, UCBL/CNRS/CNES/Herakles (groupe Safran), Bâtiment Raulin, 2 rue Victor Grignard, 69622, Villeurbanne Cedex, France

    A. El Hajj, A. J. Bougrine, D. M. Le, V. Pasquet & H. Delalu

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  1. A. El Hajj
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  2. A. J. Bougrine
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  3. D. M. Le
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  4. V. Pasquet
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  5. H. Delalu
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Correspondence to V. Pasquet.

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El Hajj, A., Bougrine, A.J., Le, D.M. et al. Another route to obtain pyrazolidine passing through the synthesis of 1 and 2-pyrazoline by intramolecular Raschig way. Reac Kinet Mech Cat 120, 619–635 (2017). https://doi.org/10.1007/s11144-016-1117-3

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  • DOI: https://doi.org/10.1007/s11144-016-1117-3

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