Journal: Organic Process Research & Development

Abbreviation

Org. Process Res. Dev.

Publisher

American Chemical Society

Journal Volumes

ISSN

1083-6160
1520-586X

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Publications 1 - 10 of 19
  • Removal of Heavy Metals from Organic Reaction Mixtures
    Item type: Journal Article
    Barbaras, Damien; Brozio, Jörg; Johannsen, Ib; et al. (2009)
    Organic Process Research & Development
  • Development of an Operationally Simple, Scalable, and HCN-Free Transfer Hydrocyanation Protocol Using an Air-Stable Nickel Precatalyst
    Item type: Review Article
    Reisenbauer, Julia C.; Bhawal, Benjamin; Jelmini, Nicola; et al. (2022)
    Organic Process Research & Development
    Hydrocyanation reactions enable access to synthetically valuable nitriles from readily available alkene precursors. However, hydrocyanation reactions using hydrogen cyanide (HCN) or similarly toxic reagents on laboratory scale can be particularly challenging due to their hazardous nature. In addition, such processes typically require air- and temperature-sensitive Ni(0) precatalysts, further reducing the operational simplicity of this transformation. Herein, we report a HCN-free transfer hydrocyanation of alkenes and alkynes that employs commercially available aliphatic nitriles as sacrificial HCN donors in combination with a catalytic amount of air-stable and inexpensive NiCl2as a precatalyst and a cocatalytic Lewis acid. The scalability and robustness of the catalytic process were demonstrated by the hydrocyanation of α-methylstyrene on a 100 mmol scale (11.4 g of product obtained) using 1 mol % of the Ni catalyst. In addition, the feasibility of the dehydrocyanation protocol using the air-stable Ni(II) precatalyst and norbornadiene as a sacrificial acceptor was showcased by the selective conversion of an aliphatic nitrile into the corresponding alkene.
  • Pressure-resistant small-scale reaction calorimeter that combines the principles of power compensation and heat balance (CRC.v4)
    Item type: Journal Article
    Visentin, Fabio; Gianoli, Stefano I.; Zogg, Andreas; et al. (2004)
    Organic Process Research & Development
  • Analysis of two-liquid-phase multistep biooxidation based on a process model
    Item type: Journal Article
    Bühler, Bruno; Straathof, Adrie J.J.; Witholt, Bernard; et al. (2006)
    Organic Process Research & Development
  • Enantioselective reduction of nitroalkene mixtures by in situ equilibration
    Item type: Journal Article
    Czekelius, Constantin; Carreira, Erick M. (2007)
    Organic Process Research & Development
  • Deracemization via Periodic and Non-periodic Temperature Cycles: Rationalization and Experimental Validation of a Simplified Process Design Approach
    Item type: Review Article
    Breveglieri, Francesca; Bodák, Brigitta; Mazzotti, Marco (2021)
    Organic Process Research & Development
    Solid-state deracemization via temperature cycles is a promising technique that combines crystallization and racemization in the same batch process to attain enantiomer purification. This method is particularly attractive because the target enantiomer can be isolated with a 100% yield, and a large number of operating parameters can be adjusted to do this effectively. However, this implies that several choices need to be made to design the process for a new compound. In this work, we provide a solution to this dilemma by suggesting a simplified model-free design approach based on a single dimensionless parameter, that is, the dissolution factor, that represents the cycle capacity. This quantity is obtained from a novel rescaling of the model equations proposed in previous work and acts as a handy design parameter because it only depends on the operating conditions, such as the suspension density, the enantiomeric excess, and the difference in solubility between high and low temperatures in the cycle. With extensive modeling studies, supported by experimental results, we demonstrate the primary and general effect of the dissolution factor on the deracemization process and thus its relevance for the process design. Through both experiments and simulations, we rationalize and evaluate the process performance when periodic and non-periodic temperature cycles are applied to the deracemization of virtual and real compounds with different properties, that is, growth rate and solubility. Based on the approach proposed here, we clarify how the combined effect of more operating conditions can be exploited to obtain quasi-optimal process performance, which results superior when deracemization via periodic temperature cycles is performed.
  • Enantioselective, Chromatography Free Synthesis of beta(3) Amino Acids with Natural and Unnatural Side Chains
    Item type: Journal Article
    Gerfaud, Thibaud; Chiang, Ying-Ling; Kreituss, Imants; et al. (2012)
    Organic Process Research & Development
  • Efficient Synthesis of a 5-HT2C Receptor Agonist Precursor
    Item type: Journal Article
    Peters, René; Waldmeier, Pius; Joncour, Agnès (2005)
    Organic Process Research & Development
  • Endoscopy-Based in Situ Bulk Video Imaging of Batch Crystallization Processes
    Item type: Journal Article
    Simon, Levente L.; Nagy, Zoltan K.; Hungerbühler, Konrad (2009)
    Organic Process Research & Development
  • Assessment of recent process analytical technology (PAT) trends
    Item type: Journal Article
    Simon, Levente L.; Pataki, Hajnalka; Marosi, György; et al. (2015)
    Organic Process Research & Development
Publications 1 - 10 of 19