A Scalable Solution to Constant-Potential Flow Electrochemistry

被引:7
作者
Griffin, Jeremy D. [1 ]
Harper, Kaid C. [1 ]
Morales, Simon Velasquez [1 ]
Morrill, Westin H. [1 ]
Thornton, William I. [1 ]
Sutherland, David [1 ]
Greiner, Bradley A. [1 ]
机构
[1] AbbVie Inc, Proc Res & Dev, N Chicago, IL 60064 USA
关键词
flow chemistry; electrochemistry; CSTR; Shono oxidation; ELECTROORGANIC CHEMISTRY; ANODIC-OXIDATION; GRIGNARD-REAGENTS; SAFE; METAL; BATCH;
D O I
10.1021/acs.oprd.3c00432
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
The burgeoning interest in new electrochemical methods holds promise to provide a plethora of strategic disconnections for pharmaceutical compounds that are safer, less wasteful, and more streamlined than traditional chemical strategies. The use of organic electrochemistry in the commercial production of pharmaceuticals is exceedingly rare due to the lack of a modular infrastructure. Herein we describe the use of cascading continuous stirred tank reactors with individual cell potential control applied over reaction "stages" which demonstrate a balance between high selectivity and throughput necessary for electrochemistry to be a viable strategy in the pharmaceutical space. Using the high degree of control of cell potential afforded by this reactor design, a 1 kg demonstration was achieved in 9 h with high selectivity and yield (2.6 kg/day throughput).
引用
收藏
页码:1877 / 1885
页数:9
相关论文
共 71 条
  • [1] Reactor Design for the Direct Electrosynthesis of Periodate
    Arndt, Sebastian
    Ruecker, Richard
    Stenglein, Andreas
    Waldvogel, Siegfried R.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (08) : 2447 - 2455
  • [2] ENANTIOSELECTIVE SYNTHESIS OF THE CARBAPENEM RING-SYSTEM FROM (S)-PROLINE
    ASADA, S
    KATO, M
    ASAI, K
    INEYAMA, T
    NISHI, S
    IZAWA, K
    SHONO, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (08) : 486 - 488
  • [3] Applications of Flow Microreactors in Electrosynthetic Processes
    Atobe, Mahito
    Tateno, Hiroyuki
    Matsumura, Yoshimasa
    [J]. CHEMICAL REVIEWS, 2018, 118 (09) : 4541 - 4572
  • [4] ELECTROCHEMICAL OXIDATION OF PROLINE DERIVATIVES - TOTAL SYNTHESES OF BULGECININE AND BULGECIN-C
    BARRETT, AGM
    PILIPAUSKAS, D
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (08) : 2787 - 2800
  • [5] Kilo-Scale Electrochemical Oxidation of a Thioether to a Sulfone: A Workflow for Scaling up Electrosynthesis
    Bottecchia, Cecilia
    Lehnherr, Dan
    Levesque, Francois
    Reibarkh, Mikhail
    Ji, Yining
    Rodrigues, Vailankanni L.
    Wang, Heather
    Lam, Yu-hong
    Vickery, Thomas P.
    Armstrong, Brittany M.
    Mattern, Keith A.
    Stone, Kevin
    Wismer, Michael K.
    Singh, Andrew N.
    Regalado, Erik L.
    Maloney, Kevin M.
    Strotman, Neil A.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2022, 26 (08) : 2423 - 2437
  • [6] Development of a Safe and Scalable Process for the Preparation of Allyl Glyoxalate
    Buetti-Weekly, Michele T.
    Clifford, Pamela
    Jones, Brian P.
    Nelson, Jade D.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (01) : 82 - 90
  • [7] On the performance of liquid-liquid Taylor flow electrochemistry in a microreactor-A CFD study
    Cao, Yiran
    Padoin, Natan
    Soares, Cintia
    Noe, Timothy
    [J]. CHEMICAL ENGINEERING JOURNAL, 2022, 427
  • [8] Cardinale L, 2023, ADV CATAL, V72, P57, DOI 10.1016/bs.acat.2023.07.009
  • [9] Organic Electrosynthesis: From Laboratorial Practice to Industrial Applications
    Cardoso, David S. P.
    Sljukic, Biljana
    Santos, Diogo M. F.
    Sequeira, Cesar A. C.
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2017, 21 (09) : 1213 - 1226
  • [10] Large-scale oxidations in the pharmaceutical industry
    Caron, Stephane
    Dugger, Robert W.
    Ruggeri, Sally Gut
    Ragan, John A.
    Ripin, David H. Brown
    [J]. CHEMICAL REVIEWS, 2006, 106 (07) : 2943 - 2989