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Synthetic Methodology "Without Reagents" Tandem Enzymatic and Electrochemical Methods for the Manufacturing of Fine Chemicals

EPA Grant Number: R826113
Title: Synthetic Methodology "Without Reagents" Tandem Enzymatic and Electrochemical Methods for the Manufacturing of Fine Chemicals
Investigators: Hudlicky, Tomas , Butora, Gabor , Gonzalez, David
Current Investigators: Hudlicky, Tomas
Institution: University of Florida
EPA Project Officer: Karn, Barbara
Project Period: September 1, 1997 through August 31, 2000
Project Amount: $411,593
RFA: Technology for a Sustainable Environment (1997)
Research Category: Pollution Prevention/Sustainable Development

Description:

This proposal is aimed at the development of alternative synthetic methodology that will reduce and eventually replace some of the traditional and harmful reagents and solvents used in chemical and pharmaceutical manufacturing. It combines in tandem the use of biocatalysis with electrochemistry for oxidations, reductions and other functionalizations to reduce and replace the current dependence on either toxic solvents or metal-based reagents. Biocatalysis proceeds in aqueous medium and in most cases, the fermentation residues are judged disposable to municipal sewers after sterilization. It frequently provides optically pure metabolites from achiral compounds. Electrochemistry is the most efficient and the cleanest way in which electrons can be added to (reduction) or subtracted from (oxidation) organic compounds. It proceeds with essentially no hazards in simple solvents and under mild conditions.

The use of these two technologies in tandem will be applied to both known and new reaction sequences with the idea of replacing some of the currently known methods of oxidation and reduction. As a special benefit the research described in this proposal targets aromatic compounds as starting materials, as these are frequently viewed as harmful. Their use in "green" manufacturing constitutes their effective removal from the potential waste pool and therefore bypasses their costly disposal or storage with the added feature of providing useful end products.

Approach:

Two technologies will be utilized in this project: Enzymatic oxidation. Recombinant organisms and blocked mutants of common soil bacteria are used to oxidize numerous aromatic substrates to optically pure arene cis-diols. This technique is well established in our laboratory and the current focus of this project will be in part provision of known starting materials for synthetic ventures and in part investigation of new substrate/enzyme matches to furnish new metabolites.

Electrochemical functionalization. Procedures will be developed for the synthesis of epoxides, diols, and aziridines from olefins, reduction of halides, sulfonate esters, and xanthates, deoxygenation protocols for sugars and nucleosides, and carbon-carbon bond forming procedures for oxidative coupling. These features will obviate the use of such reagents as m-chioroperbenzoic acid, tributyltin hydride, and lithium aluminum hydride, and prevent the use of solvents such as benzene, tetrahydrofuran or methylene chloride.

Expected Results:

It is expected that the proposed technology will be demonstrated by adjusting currently known syntheses (some from our laboratory) of cyclitols, carbohydrates, and alkaloids and replacing as many steps as possible with the above electrochemical techniques. A comparison will be made in evaluating the improvement and the saving in overall waste mass for each new process. In addition, it is hoped that a simple electrochemical procedure will be designed for the deoxygenation of secondary alcohols via electrochemical reduction of their sulfur derivatives. Currently, the only method of accomplishing this reduction is the use of tributyltin hydride. The procedure is frequently used to produce important deoxysugars. A major focus of our project will involve the development of alternative "green" methods of synthesis for this group of compounds.

Publications and Presentations:

Publications have been submitted on this project: View all 87 publications for this project

Journal Articles:

Journal Articles have been submitted on this project: View all 34 journal articles for this project

Supplemental Keywords:

enzymes, green chemistry, pollution prevention, toxic chemicals disposal, toxic chemicals, conversion, electrochemistry, green manufacturing, pharmaceutical intermediates, clean technologies, innovative technology, renewable, waste reduction, waste minimization, environmentally conscious manufacturing, treatment, remediation, bioremediation, tandem enzyme electrochemical oxidation reduction. , Industry Sectors, Toxics, Sustainable Industry/Business, Scientific Discipline, RFA, Technology for Sustainable Environment, Sustainable Environment, HAPS, Manufacturing - NAIC 31-33, Environmental Engineering, cleaner production/pollution prevention, Environmental Chemistry, 33/50, aqueous solvents, biocatalysis, cleaner production, carbon-carbon binding, reagents, benzene, green chemistry, Methylene chloride (Dichloromethane), solvents, environmentally conscious manufacturing, green process systems, environmentally benign solvents, industrial innovations, enzyme transformations, electrochemical techniques, innovative technology, chemical manufacturing, pollution prevention

Progress and Final Reports:
Final Report

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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.

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