Nitrogen Heterocycle Synthesis and Chemical Engineering Applications in Multi-phasic Systems of C O2 and C O2-Expanded LiquidEPA Grant Number: F6A10011
Title: Nitrogen Heterocycle Synthesis and Chemical Engineering Applications in Multi-phasic Systems of C O2 and C O2-Expanded Liquid
Investigators: Ciccolini, Rocco P.
Institution: Massachusetts Institute of Technology
EPA Project Officer: Jones, Brandon
Project Period: September 1, 2006 through September 1, 2009
Project Amount: $111,172
RFA: STAR Graduate Fellowships (2006) RFA Text | Recipients Lists
Research Category: Engineering and Environmental Chemistry , Fellowship - Environmental Engineering , Academic Fellowships
The goal of this work is to create new knowledge and better understanding of C-N bond-forming reactions in multiphasic systems of C O2 and C O2-expanded liquids.
To achieve this goal, the detailed examination of a model synthetic system affording pharmaceutically-attractive tetrahydroisoquinolines and tetrahydro-β-carbolines via the Pictet-Spengler cyclization reaction will be conducted. In further developing strategies for effecting C-N bond-forming reactions in multiphasic C O2-based media, fundamental chemical engineering principles will be applied. Specifically, experiments will be designed to reveal information pertaining to: (1) reaction engineering; analysis of reaction rates, conversion, selectivity, ab initio kinetic modeling, (2) mass-transport; effects of agitation, recirculation, and emulsification, and (3) thermodynamics; dynamic phase equilibrium and phase-specific species partitioning as a function of process operating conditions.
The end result of this work is to (1) develop an optimized C-N bond-forming process that is not only attractive from a chemistry and environmental standpoint, but also in the chemical process engineering sense, and (2) apply these strategies towards the synthesis of pharmaceutical and specialty chemicals with minimal use of environmentally-damaging solvents and reagents.