Event Title

Homogenous Catalysts for the Conversion of Epoxides to Alcohols

Research Mentor(s)

Margaret Scheuermann

Description

There is a large demand for terminal alcohols in both bulk and fine chemical synthesis. Current methods have limitations including generating stoichiometric waste or having poor selectivity for the primary alcohol over the secondary alcohol. My project focuses on the transformation of primary alcohols from terminal epoxides utilizing hydrogenation catalysts. Conditions were optimized for the conversion of 1,2-epoxyoctane to 1-octanol. It was found that (POCOP)Ir(CO) (1.3 mol %) and HOTf in a mixture of 5:1 dioxane: water with 600 psi H2 at 170 °C for 27 h yielded 74% 1-octanol. Results were characterized by GC-FID using toluene as the internal standard. Current research is being done to expand the substrate scope and determine how tolerant the reaction conditions are of varying functionality.

Document Type

Event

Start Date

May 2018

End Date

May 2018

Location

Chemistry

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

Language

English

Format

application/pdf

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May 17th, 9:00 AM May 17th, 12:00 PM

Homogenous Catalysts for the Conversion of Epoxides to Alcohols

Chemistry

There is a large demand for terminal alcohols in both bulk and fine chemical synthesis. Current methods have limitations including generating stoichiometric waste or having poor selectivity for the primary alcohol over the secondary alcohol. My project focuses on the transformation of primary alcohols from terminal epoxides utilizing hydrogenation catalysts. Conditions were optimized for the conversion of 1,2-epoxyoctane to 1-octanol. It was found that (POCOP)Ir(CO) (1.3 mol %) and HOTf in a mixture of 5:1 dioxane: water with 600 psi H2 at 170 °C for 27 h yielded 74% 1-octanol. Results were characterized by GC-FID using toluene as the internal standard. Current research is being done to expand the substrate scope and determine how tolerant the reaction conditions are of varying functionality.