Development of process analytical technologies and application for complicated reaction conditions
department or school: Science, Faculty of
department or school: Chemistry, Department of
data provider: DSpace
degree campus: UBCV
creator: Sato, Yusuke
issued: 2023-01-13T22:57:43Z
issued: 2023
related degree: Doctor of Philosophy - PhD
degree grantor: University of British Columbia
description: Real-time sample analysis, including in situ analysis and automated sampling/injection, provides timely measurements of analytes and facilitates efficient reaction elucidations. In contrast to manual sampling, real-time sample analysis eliminates laborious sample preparations and increases efficiency and robustness in obtaining data-rich information. Unfortunately, many instrumental analytical tools used for real-time reaction monitoring are only applicable to homogeneous conditions, leaving heterogeneous conditions a major challenge. This thesis explores developments and applications of new heterogenous sampling platforms to investigate reaction details. Combing commercially available laboratory equipment with an in-line dynamic mixer, an online HPLC reaction monitoring system has been developed to investigate solid/liquid heterogeneous reactions. Using this platform, a slurry tetrabenazine (TBZ) synthesis has been investigated. The isolation and characterization of unseen enone and iminium intermediates proved that the reaction underwent the aza-Michael-Mannich annulation pathway. Our increased mechanistic understanding has allowed for the reaction rate to be boosted five-fold. For liquid/liquid heterogeneous reaction monitoring, a phase-selective sampling system was developed. This was achieved by developing a novel hydrophilic/oleophobic stainless steel filter. Partition coefficients of boronic acids with varying functional groups have been tested using this platform. Biphasic Suzuki-Miyaura coupling reaction was also explored. In addition to the heterogeneous conditions, nanocluster synthesis was also known to create challenging conditions to be monitored due to its complicated polydisperse cluster formations. This thesis lastly demonstrated that real-time LCMS monitoring revealed size growth of gold nanoclusters synthesis and potential intermediates.
aggregated CHO: https://circle.library.ubc.ca/rest/handle/2429/83641
note: DEVELOPMENT OF PROCESS ANALYTICAL TECHNOLOGIES AND APPLICATION FOR COMPLICATED REACTION CONDITIONS by Yusuke Sato B.Sc., The University of Shizuoka, 2017 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY in THE FACULTY OF GRADUATE AND POSTDOCTORAL STUDIES (Chemistry) THE UNIVERSITY OF BRITISH COLUMBIA (Vancouver) January 2023 © Yusuke Sato, 2023 ii The following individuals certify that they have read, and recommend to the Faculty of Graduate and Postdoctoral Studies for acceptance, the dissertation entitled: Development of Process Analytical Technologies and Application for Complicated Reaction Conditions submitted by Yusuke Sato in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry Examining Committee: Jason E. Hein, Professor, Chemistry, UBC Supervisor Glenn Sammis, Professor, Chemistry, UBC Supervisory Committee Member Marco A. Ciufolini, Professor, Chemistry, UBC University Examiner Russ Algar, Professor, Chemistry, UBC University Examiner Additional Supervisory Committee Members: David Perrin, Professor, Chemistry, UBC Supervisory Committee Member Zachary M. Hudson, Professor, Chemistry, UBC Supervisory Committee Member iii Abstract Real-time sample analysis, including in situ analysis and automated sampling/injection, provides timely measurements of analytes and facilitates efficient reaction elucidations. In contrast to manual sampling, real-time sample analysis eliminates laborious sample preparations and increases efficiency and robustness in obtaining data-rich information. Unfortunately, many instrumental analytical tools used for real-time reaction monitoring are only applicable to homogeneous conditions, leaving heterogeneous conditions a major challenge. This thesis explores developments and applications of new heterogenous sampling platforms to investigate reaction details. Combing commercially available laboratory equipment with an in-line dynamic mixer, an o…
has type: Thesis/Dissertation
date issued: 2023-05
is shown at: 10.14288/1.0423046
language: eng
degree discipline: Chemistry
provider: Vancouver : University of British Columbia Library
publisher: University of British Columbia
rights: Attribution-NonCommercial-NoDerivatives 4.0 International
rights URI: http://creativecommons.org/licenses/by-nc-nd/4.0/
scholar level: Graduate
contributor: Hein, Jason
type: Text
identifier URI: http://hdl.handle.net/2429/83641