Benbouzid, M (1984) Synthetic and analytical investigations related to vegetable oils and fats. Doctoral thesis, Liverpool Polytechnic.

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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

Item Type:	Thesis (Doctoral)
Subjects:	Q Science > QD Chemistry
Divisions:	Pharmacy & Biomolecular Sciences
Date Deposited:	01 May 2019 10:44
Last Modified:	03 Sep 2021 21:09
DOI or ID number:	10.24377/LJMU.t.00010628
URI:	https://researchonline.ljmu.ac.uk/id/eprint/10628

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