{"id":{"repo_id":"liverpool-jm","oai_identifier":"oai:researchonline.ljmu.ac.uk:10628"},"canonical_url":"https://search.dev.ndltd.org/etd/liverpool-jm/oai:researchonline.ljmu.ac.uk:10628","repository":{"repo_id":"liverpool-jm","name":"Liverpool Jon Moores University","base_url":"https://researchonline.ljmu.ac.uk/cgi/oai2"},"display":{"title":"Synthetic and analytical investigations related to vegetable oils and fats.","abstract":"The work presented here has developed along two lines: analysis and synthesis of triacylglycerols. A new application is reported in the use of the infrared detector in HPLC for the detection and preparative and quantitative separation of triacylglycerols of seed fats and oils, acylglycerols from lipolysis mixtures and synthetic acylglycerols. The composition of the total triacylglycerol of some of these fats and oils, and the distribution of fatty acids in the sn-2 position m them are determined for the first time The n-hydrocarbon composition of most of these fats and oils is also determined for the first time. Three new routes, namely, the tosylate, the silyl ether and the phosphate route, have been explored, in the tosylate route best conditions are found for the preparation of glycerol-1,3-ditosylate and its subsequent conversion into 1,3-diacylgiycerols by nucleophilic substitution. From the 1,3-diacylglycerols, five symmetrical diacid tnacylglycerois have been prepared by reaction with an appropriate acid chloride. By the silyl ether route symmetrical diacylglycerols have been prepared from the 1,3-disilyl derivative of 1,3-dihydroxv acetone. In this regard, it is noted that selective silylation of glycerol does not take place, and the 1,3-disilyl derivative of glycerol (prepared indirectly) does not undergo nucleophilic substitution. However, this route does hot offer any advantage over existing routes. In connection with the phosphate route, preliminary experiments have shown that the diphenyl phosphate group can be substituted easily and under mild conditions by a carboxylate anion in a primary alkyl phosphate derivative in both non-polar and polar protic and aprotic solvents. The product from the reaction of diphenyl phosphoryl chloride and glycerol contained only a small amount of the desired 1,3-diphosphate derivative which has been converted into the 1,3-diacylglycerols by nucleophilic substitution","abstract_html":"The work presented here has developed along two lines: analysis and synthesis of triacylglycerols. A new application is reported in the use of the infrared detector in HPLC for the detection and preparative and quantitative separation of triacylglycerols of seed fats and oils, acylglycerols from lipolysis mixtures and synthetic acylglycerols. The composition of the total triacylglycerol of some of these fats and oils, and the distribution of fatty acids in the sn-2 position m them are determined for the first time The n-hydrocarbon composition of most of these fats and oils is also determined for the first time. Three new routes, namely, the tosylate, the silyl ether and the phosphate route, have been explored, in the tosylate route best conditions are found for the preparation of glycerol-1,3-ditosylate and its subsequent conversion into 1,3-diacylgiycerols by nucleophilic substitution. From the 1,3-diacylglycerols, five symmetrical diacid tnacylglycerois have been prepared by reaction with an appropriate acid chloride. By the silyl ether route symmetrical diacylglycerols have been prepared from the 1,3-disilyl derivative of 1,3-dihydroxv acetone. In this regard, it is noted that selective silylation of glycerol does not take place, and the 1,3-disilyl derivative of glycerol (prepared indirectly) does not undergo nucleophilic substitution. However, this route does hot offer any advantage over existing routes. In connection with the phosphate route, preliminary experiments have shown that the diphenyl phosphate group can be substituted easily and under mild conditions by a carboxylate anion in a primary alkyl phosphate derivative in both non-polar and polar protic and aprotic solvents. The product from the reaction of diphenyl phosphoryl chloride and glycerol contained only a small amount of the desired 1,3-diphosphate derivative which has been converted into the 1,3-diacylglycerols by nucleophilic substitution","abstract_has_math":false,"creators":["Benbouzid, M"],"institution":"Liverpool Polytechnic","degree_name":"phd","degree_level":"doctoral","degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1984,"date_issued":"1984-01","date_published":"1984-01","updated_at":"2026-07-24T06:30:28Z","subjects":["QD Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://doi.org/10.24377/LJMU.t.00010628","outbound_label":"DOI","outbound_source":"dc:identifier.doi"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Benbouzid, M"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["1984-01-01"]},{"key":"dc:date.issued","label":"Date","values":["1984-01"]},{"key":"dc:publisher.department","label":"Dc Publisher Department","values":["Pharmacy and Biomolecular Sciences"]},{"key":"dc:publisher.institution","label":"Dc Publisher Institution","values":["Liverpool Polytechnic"]},{"key":"dc:relation.isreferencedby","label":"Dc Relation Isreferencedby","values":["https://researchonline.ljmu.ac.uk/id/eprint/10628/"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["doctoral"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["phd"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["QD Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.doi","label":"DOI","values":["10.24377/LJMU.t.00010628"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://researchonline.ljmu.ac.uk/id/eprint/10628/1/305340.pdf"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The work presented here has developed along two lines: analysis and synthesis of triacylglycerols. A new application is reported in the use of the infrared detector in HPLC for the detection and preparative and quantitative separation of triacylglycerols of seed fats and oils, acylglycerols from lipolysis mixtures and synthetic acylglycerols. The composition of the total triacylglycerol of some of these fats and oils, and the distribution of fatty acids in the sn-2 position m them are determined for the first time The n-hydrocarbon composition of most of these fats and oils is also determined for the first time. Three new routes, namely, the tosylate, the silyl ether and the phosphate route, have been explored, in the tosylate route best conditions are found for the preparation of glycerol-1,3-ditosylate and its subsequent conversion into 1,3-diacylgiycerols by nucleophilic substitution. From the 1,3-diacylglycerols, five symmetrical diacid tnacylglycerois have been prepared by reaction with an appropriate acid chloride. By the silyl ether route symmetrical diacylglycerols have been prepared from the 1,3-disilyl derivative of 1,3-dihydroxv acetone. In this regard, it is noted that selective silylation of glycerol does not take place, and the 1,3-disilyl derivative of glycerol (prepared indirectly) does not undergo nucleophilic substitution. However, this route does hot offer any advantage over existing routes. In connection with the phosphate route, preliminary experiments have shown that the diphenyl phosphate group can be substituted easily and under mild conditions by a carboxylate anion in a primary alkyl phosphate derivative in both non-polar and polar protic and aprotic solvents. The product from the reaction of diphenyl phosphoryl chloride and glycerol contained only a small amount of the desired 1,3-diphosphate derivative which has been converted into the 1,3-diacylglycerols by nucleophilic substitution"]},{"key":"dc:format","label":"Dc Format","values":["text"]},{"key":"dc:title","label":"Title","values":["Synthetic and analytical investigations related to vegetable oils and fats."]}]}],"canonical_facts":{"dc:creator":["Benbouzid, M"],"dc:date":["1984-01-01"],"dc:date.issued":["1984-01"],"dc:description.abstract":["The work presented here has developed along two lines: analysis and synthesis of triacylglycerols. A new application is reported in the use of the infrared detector in HPLC for the detection and preparative and quantitative separation of triacylglycerols of seed fats and oils, acylglycerols from lipolysis mixtures and synthetic acylglycerols. The composition of the total triacylglycerol of some of these fats and oils, and the distribution of fatty acids in the sn-2 position m them are determined for the first time The n-hydrocarbon composition of most of these fats and oils is also determined for the first time. Three new routes, namely, the tosylate, the silyl ether and the phosphate route, have been explored, in the tosylate route best conditions are found for the preparation of glycerol-1,3-ditosylate and its subsequent conversion into 1,3-diacylgiycerols by nucleophilic substitution. From the 1,3-diacylglycerols, five symmetrical diacid tnacylglycerois have been prepared by reaction with an appropriate acid chloride. By the silyl ether route symmetrical diacylglycerols have been prepared from the 1,3-disilyl derivative of 1,3-dihydroxv acetone. In this regard, it is noted that selective silylation of glycerol does not take place, and the 1,3-disilyl derivative of glycerol (prepared indirectly) does not undergo nucleophilic substitution. However, this route does hot offer any advantage over existing routes. In connection with the phosphate route, preliminary experiments have shown that the diphenyl phosphate group can be substituted easily and under mild conditions by a carboxylate anion in a primary alkyl phosphate derivative in both non-polar and polar protic and aprotic solvents. The product from the reaction of diphenyl phosphoryl chloride and glycerol contained only a small amount of the desired 1,3-diphosphate derivative which has been converted into the 1,3-diacylglycerols by nucleophilic substitution"],"dc:format":["text"],"dc:identifier.doi":["10.24377/LJMU.t.00010628"],"dc:identifier.uri":["https://researchonline.ljmu.ac.uk/id/eprint/10628/1/305340.pdf"],"dc:publisher.department":["Pharmacy and Biomolecular Sciences"],"dc:publisher.institution":["Liverpool Polytechnic"],"dc:relation.isreferencedby":["https://researchonline.ljmu.ac.uk/id/eprint/10628/"],"dc:subject":["QD Chemistry"],"dc:title":["Synthetic and analytical investigations related to vegetable oils and fats."],"dc:type":["Thesis"],"dc:type.qualificationlevel":["doctoral"],"dc:type.qualificationname":["phd"]},"updated_at":"2026-07-24T06:30:28Z"}