Grantee Research Project Results
Nitrogen Heterocycle Synthesis and Chemical Engineering Applications in Multi-phasic Systems of C O2 and C O2-Expanded Liquid
EPA Grant Number: F6A10011Title: 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: Packard, Benjamin H
Project Period: September 1, 2006 through September 1, 2009
Project Amount: $111,172
RFA: STAR Graduate Fellowships (2006) RFA Text | Recipients Lists
Research Category: Academic Fellowships , Fellowship - Environmental , Safer Chemicals
Objective:
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.
Approach:
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.
Expected Results:
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.
Supplemental Keywords:
Supercritical carbon dioxide, carbon dioxide-expanded liquids, green chemistry, chemical engineering, chemistry, organic synthesis, nitrogen heterocycles, carbon-nitrogen bond formation, reaction engineering, kinetics, mass transport, thermodynamics, phase behavior, multiphasic, pharmaceutical, specialty chemicals, tetrahydroisoquinolines, tetrahydro-β-carbolines,, Sustainable Industry/Business, RFA, Scientific Discipline, INTERNATIONAL COOPERATION, Technology for Sustainable Environment, Chemical Engineering, Sustainable Environment, Environmental Chemistry, Chemicals Management, alternative chemical synthesis, environmental sustainability, supercritical carbon dioxide, reaction engineering, reaction kinetics, chemcial synthesis, chemical manufacturing, chemical processing, environmentally benign solvents, kinetic data, alternative solventsProgress and Final Reports:
The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Conclusions drawn by the principal investigators have not been reviewed by the Agency.