{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70106"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70106","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Analysis, Experimental Optimization and Chemical Synthesis of Cyclic Monomers Occurring in Edible Fats and Oils","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.","abstract_html":"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 <span class=\"etd-inline-math\">&omega;</span>-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.","abstract_has_math":true,"creators":["Rojo Moreno, Jose Andres"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Food Science","degree_department":null,"school":null,"contributors":["Perkins, Edward G."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-15T21:10:20Z","date_published":"2014-12-15T21:10:20Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Agriculture, Food Science and Technology","Chemistry, Analytical","Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8908814"],"render_values":[{"text":"(UMI)AAI8908814","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70106","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Perkins, Edward G."]},{"key":"dc:creator","label":"Author","values":["Rojo Moreno, Jose Andres"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T21:10:20Z","10000-01-01","1988"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Food Science"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Agriculture, Food Science and Technology","Chemistry, Analytical","Chemistry, Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/70106","(UMI)AAI8908814"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["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.","Made available in DSpace on 2014-12-15T21:10:20Z (GMT). No. of bitstreams: 1 8908814.pdf: 7503391 bytes, checksum: 8d4cd14baac4b79cd222f1209cdc9a93 (MD5) Previous issue date: 1988","Embargo set by: Seth Robbins for item 70272 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","188 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1988."]},{"key":"dc:title","label":"Title","values":["Analysis, Experimental Optimization and Chemical Synthesis of Cyclic Monomers Occurring in Edible Fats and Oils"]}]}],"canonical_facts":{"dc:contributor":["Perkins, Edward G."],"dc:creator":["Rojo Moreno, Jose Andres"],"dc:date":["2014-12-15T21:10:20Z","10000-01-01","1988"],"dc:description":["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.","Made available in DSpace on 2014-12-15T21:10:20Z (GMT). No. of bitstreams: 1 8908814.pdf: 7503391 bytes, checksum: 8d4cd14baac4b79cd222f1209cdc9a93 (MD5) Previous issue date: 1988","Embargo set by: Seth Robbins for item 70272 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","188 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1988."],"dc:identifier":["http://hdl.handle.net/2142/70106","(UMI)AAI8908814"],"dc:subject":["Agriculture, Food Science and Technology","Chemistry, Analytical","Chemistry, Organic"],"dc:title":["Analysis, Experimental Optimization and Chemical Synthesis of Cyclic Monomers Occurring in Edible Fats and Oils"],"dc:type":["text"],"thesis:degree_discipline":["Food Science"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:02Z"}