Nitrogen Heterocycle Synthesis and Chemical Engineering Applications in Multi-phasic Systems of C O2 and C O2-Expanded Liquid

EPA 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: 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: 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.

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,, RFA, Scientific Discipline, INTERNATIONAL COOPERATION, Sustainable Industry/Business, Chemical Engineering, Sustainable Environment, Environmental Chemistry, Technology for Sustainable Environment, Chemicals Management, reaction engineering, environmental sustainability, environmentally benign solvents, alternative solvents, chemcial synthesis, supercritical carbon dioxide, chemical manufacturing, chemical processing, alternative chemical synthesis, green chemistry, kinetic data

Progress and Final Reports:

  • 2007
  • 2008
  • Final