Analysis, Experimental Optimization and Chemical Synthesis of Cyclic Monomers Occurring in Edible Fats and Oils

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 ω-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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

Dissertation

Discipline thesis:degree_discipline

Food Science

Grantor

University of Illinois at Urbana-Champaign

Year dc:date

2014

Author dc:creator

• Rojo Moreno, Jose Andres

Contributors dc:contributor

• Perkins, Edward G.

• Agriculture, Food Science and Technology
• Chemistry, Analytical
• Chemistry, Organic

Identifier

(UMI)AAI8908814

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/70106