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Expert in Chemical Research, Synthetic Methods, Free Radical Chemistry, Industrial Research
Available for your Consulting and Expert Witness Needs
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Summary of Expertise:
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During his industrial and academic careers Expert has had much success in applying experimental and theoretical principles to problem-solving. A few examples of his expertise in chemical innovation follow. At Tennessee Eastman in 1948, Expert discovered a method of grafting acrylinitrile (AN) to cellulose derivatives to give a soluble, fiber-forming AN polymer with improved dyeability and processability. At the time, it was a new concept to modify polymer properties.
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At Du Pont, during the years 1949-63, Expert made major contributions in the pioneering research section of organic chemicals, among them were: 1) A synthetic strategy for tetrahydrofuran manufacture from cheap materials; 48 different routes were proposed, based on feasible chemical reactions. One was chosen for research, and has had commercial application. 2) Serendipitous discovery of free radical addition of perfluoroalkyl iodides (RfI) to unsaturated compounds. This new method triggered large scale use of RfI for manufacture of many products on a world wide scale, with applications in diverse fields such as textile, paper, pharmaceutical, polymeric, and surface active materials. 3) The initial discovery lead to a study of chemical reactions and properties of Rf(F-alkyl)-containing substances. An important breakthrough was synthesis of long-chain 2-(F-alkyl)-1-iodoethanes (RfCH2CH2I) and derivatives, i.e., alcohols RfCH2CH2OH, thiols RfCH2CH2SH, esters, alkenes, and related substances. Innovation here derived from applying both experimental and theoretical principles. SYNTHESES WITH PERFLUOROALKYL IODIDES. Expert first prepared the compound CF3(CF2)6(CH2)15CH3, from CF3(CF2)6I and 1-hexadec-1-ene in 1976. The method is general for RfI and RhCH=CH2 and requires two steps; the yields are 90% or better. Important new applications for these "diblock" compounds, FmHn, have appeared. They behave as amphiphiles at the fluococarbon/hydrocarbon interface, are excellent stabilizers of fluorocarbon-in-water emulsions, and depending on the length of the FmHn segments, they form micelles in either hydrogenated or fluorinated solvents. Based on the unique properties of fluorcarbons, such as biological inertness, gas-dissolving capacity, very low surface tension, and high fluidity and spreading characteristics, fluorinated colloidal systems are of interest for a range of medical applications (oxygen transport, liquid ventilation, diagnosis). Fluorinated lipids form stable vesicles, and they can also be formed by combining standard phospholipids with FmHn blocks. The resulting fluorinated vesicles are more stable and less permeable than those made of the phospholipid alone, indicating that the "diblock" segments segregate and organize tightly within the bilayer. Numerous studies exist on the structure of crystals of diblocks, and fibrous gels formed by these compounds in a variety of solvents, including hydrocarbons, fluorocarbons, and carbon dioxide.
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A new stage in Expert's professional career occurred in 1969 when he began consulting with a New Venture Group of a major multinational corporation. His skills in searching out viable industrial routes to useful products were sharpened, as they were applied to new areas of technical interest. Expert published very seldom in this period, as his proposals and suggestions were primarily designed to stimulate other researchers to find economically competitive and practical chemical solutions to problems. He maintained an active research program on certain problems believed to have little possibility of success or of a more technically complex or long-range nature.
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Major discoveries in fluorocarbon chemistry, stemming from free radical reactions of RfI, were outlined above. From novel derivatives of RfI a rich chemistry is coming into existence. As part of this development, Expert has done mechanistic studies to reveal the chemical effects of fluorine substitution on reaction behavior. These studies include elimination and substitution reactions of derived iodoalkanes, radical and nucleophilic cyclization reactions, and alkylation of amides by way of (imidate) intermediates. Findings have given important guidance to practical applications. For example, a high yield synthesis of alcohols, RfCH2CH2OH(3) was achieved from reaction of RfCH2CH2I(1) with amides such as 2-pyrrolidinone(2). The imidate from 2 and 3 was synthesized and shown to be the key intermediate in the alcohol synthesis. Expert determined the effect of reaction conditions, and structures of reactants on yield product. Synthesis and reactions of thiols RfCH2CH2SH is another area of great promise. Thiols are versatile compounds and provide a convenient source of the perfluoroalkyl group, to be introduced into derivatives for practical use. A variety of compounds have been prepared that have already found useful applications. Among them are surfactants, paper-treating compounds, poly-urethanes, and telomers from vinyl monomers terminated by RfCH2CH2SH.
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In Expert's scouting research he has frequently used biphasic reaction systems to improve reaction rate, yield, and purity of the product and facility of processing. This technique is now widely used in organic synthesis and manufacturing. An example is found in a U.S. Patent assigned to Ciba-Geigy Corporation. Subsequently, Expert devised a high yield synthesis of phenyl vinyl sulfone (C6H5SO2CH=CH2), by making use of phase transfer technology disclosed in a U.S. patent. Phenyl vinyl sulfone is widely used as a synthon in organic chemistry. This work will soon be submitted for publication.
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Expert first prepared the compound CF3(CF2)6(CH2)15CH3, from CF3(CF2)6I and 1-hexadec-1-ene in 1976. The method is general for RfI and RhCH=CH2 and requires two steps; the yields are 90% or better. Important new applications for these "diblock" compounds, FmHn, have appeared. They behave as amphiphiles at the fluococarbon/hydrocarbon interface, are excellent stabilizers of fluorocarbon-in-water emulsions, and depending on the length of the FmHn segments, they form micelles in either hydrogenated or fluorinated solvents. Based on the unique properties of fluorcarbons, such as biological inertness, gas-dissolving capacity, very low surface tension, and high fluidity and spreading characteristics, fluorinated colloidal systems are of interest for a range of medical applications (oxygen transport, liquid ventilation, diagnosis). Fluorinated lipids form stable vesicles, and they can also be formed by combining standard phospholipids with FmHn blocks. The resulting fluorinated vesicles are more stable and less permeable than those made of the phospholipid alone, indicating that the "diblock" segments segregate and organize tightly within the bilayer. Numerous studies exist on the structure of crystals of diblocks, and fibrous gels formed by these compounds in a variety of solvents, including hydrocarbons, fluorocarbons, and carbon dioxide.
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Show Secondary and Basic Areas of Expertise | Localities:
Expert may consult nationally and internationally, and is also local to the following cities: Saint Louis, Missouri;
Evansville, Indiana;
and Owensboro, Kentucky.
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Degree |
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Subject |
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Institution |
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Honors |
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1948
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PhD
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Organic Chemistry
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University of Illinois
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1946
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BA
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Chemistry
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University of Minnesota
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Cum Laude
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| Years |
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Employer |
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Title |
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1996 to
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(Undisclosed University)
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Professor of Chemistry Emeritus
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1988 to
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(Undisclosed)
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Professor of Chemistry Emeritus
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1972 to 1988
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(Undisclosed)
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Professor of Chemistry
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1966 to 1972
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(Undisclosed)
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Associate Professor of Chemistry
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1963 to 1966
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North Park College
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Associate Professor of Chemistry
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1949 to 1963
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E. I. du Pont de Nemours & Co.
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Research Chemist
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1948 to 1949
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Tennessee Eastman Corporation
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Research Chemist
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Associations/Societies
Expert is a member of the American Chemical Society and a Fellow of the American Scientific Affiliation.
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Professional Appointments
He was an Honorary Fulbright Professor and a Richard Merton Professor at Wuppertal University in Germany.
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Awards/Recognition
Expert was honored with the Senior U.S. Scientist and Humboldt Award by Alexander von Humboldt-Stiftung at the Technical University in Braunschweig, Germany. He was one of the first Americans to receive the prize.
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| Publications: |
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Selected Publications and Publishers
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- Journal of Fluorine Chemistry
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- Journal of Organic Chemistry
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- Journal of Fluorine Chemistry
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| International Experience: |
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Summary |
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Asia
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Expert has been an invited guest lecturer at seven universities in China and at another seven universities and institutes in Japan.
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| Language Skills: |
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Education
