Analysis, Experimental Optimization and Chemical Synthesis of Cyclic Monomers Occurring in Edible Fats and Oils
Rojo Moreno, Jose Andres
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https://hdl.handle.net/2142/70106
Description
Title
Analysis, Experimental Optimization and Chemical Synthesis of Cyclic Monomers Occurring in Edible Fats and Oils
Author(s)
Rojo Moreno, Jose Andres
Issue Date
1988
Doctoral Committee Chair(s)
Perkins, Edward G.
Department of Study
Food Science
Discipline
Food Science
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Agriculture, Food Science and Technology
Chemistry, Analytical
Chemistry, Organic
Abstract
The qualitative and quantitative aspects of the determination of C$\sb $ cyclic fatty acids in edible fats and oil were studied. First, the unequivocal identification of isomeric species of cyclic monomers was carried out using solid phase extraction for the fast isolation of purified fractions of cyclics and through the development of empirical mathematical models for the prediction of the chromatographic retention characteristics of these compounds. In addition, the experimental optimization of the analytical method was achieved using chemometric techniques and by investigating possible substitutes for the internal standard. Simplex optimization was used to determine optimum chromatographic isomer separation for a given time/resolution response function; a fractional factorial experiment at two levels was used to estimate the effects of five analytical conditions. Finally, the chemical synthesis of the 1,2-disubstituted cyclopentyl fatty acid methyl esters was undertaken to definitively confirm the occurrence of these compounds in fats and oils. Methyl 9-(2$\sp\prime$-n-butylcyclopentyl) nonanoate and methyl 10-(2$\sp\prime$-n-propylcyclopentyl) decanoate were prepared by a Wittig reaction between 2-alkylcyclopentanones and $\omega$-carbomethoxyalkyl triphenylphosphonium bromides. The GC-retention features, the mass fragmentation pattern and the spectroscopic characteristics of the final synthetic products and intermediates were discussed in detail.
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