Investigating the Diels-Alder Reaction between Trans,trans-2,4-hexadienyl acetate and N-propylmaleimide at the Oil-Water Interface using Microfluidics
Name:
The thesis of Abdulaziz Alruwaithi_Final Version 3.pdf
Size:
5.082Mb
Format:
PDF
Description:
Abdulaziz Alruwarthi - Final Paper
Embargo End Date:
2021-03-10
Type
ThesisAuthors
Alruwaithi, Abdulaziz A.
Advisors
Mishra, Himanshu
Committee members
Huang, Kuo-Wei
Farooq, Aamir

Program
Chemical ScienceKAUST Department
Physical Science and Engineering (PSE) DivisionDate
2020-03Embargo End Date
2021-03-10Permanent link to this record
http://hdl.handle.net/10754/662135
Metadata
Show full item recordAccess Restrictions
At the time of archiving, the student author of this thesis opted to temporarily restrict access to it. The full text of this thesis will become available to the public after the expiration of the embargo on 2021-03-10.Abstract
Abstract: Greener synthetic routes for producing organic molecules are desirable to reduce environmental pollution and lower manufacturing costs.2 In this context, Sharpless & co-workers reported that it is possible to achieve dramatic rate enhancements in a number of cycloaddition reactions, if they were conducted in vigorously mixed oil-water emulsions instead of bulk organic solvents.1 These interfacial reactions – which came to be known as “on-water” reactions – thus present a tantalizing prospect for green chemistry. However, despite many experimental and theoretical studies along this theme, a clear understanding of the governing factors and mechanisms remains unavailable. For instance, proposed mechanisms vary from dangling hydrogen bonds stabilizing transition states, to the specific adsorption of hydroxide ions at the water-organic interface, and the partial dissolution of reactants in water leading to products.3,4,5Additional effects include sharp variations in dielectric constants and hydration levels across the interface and hydrodynamic effects during vigorous stirring. In this thesis, we investigate a Diels-Alder reaction between two water-insoluble reactants – trans,trans-2,4-hexadienyl acetate and N-propylmaleimide– to disentangle the contributions of bulk reactions from interfacial reactions. We compare the conversion of reactants into products in the following scenarios: pure reactants (i) mixed into each other (neat condition), (ii) dissolved in hexane, (iii) dissolved in hexane and vigorously stirred with water (1:1 v/v), and (iv) dissolved in hexane and vigorously stirred in water-methanol mixtures. In addition to vigorously-stirred emulsions that produce polydisperse emulsions, we designed and developed microfluidic devices that allowed us to precisely controlled the water-organic interfacial area. With this6 device, we pin-point interfacial effects on the reaction rates.Citation
Alruwaithi, A. A. (2020). Investigating the Diels-Alder Reaction between Trans,trans-2,4-hexadienyl acetate and N-propylmaleimide at the Oil-Water Interface using Microfluidics. KAUST Research Repository. https://doi.org/10.25781/KAUST-3Q412ae974a485f413a2113503eed53cd6c53
10.25781/KAUST-3Q412