Chromatographic analysis of polyglycerols and their fatty acid esters

Sahasrabudhe, M. R.

doi:10.1007/bf02666773

Cited by 43 publications

(20 citation statements)

References 18 publications

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“…Polymerisation of glycerol to various diglycerol isomers polyglycerol fatty acid esters, pure standards of polyglycerols could be obtained using fractionated distillation [ 15,17] or by selective chemical synthesis [ 15,23]. Although some of these analyses were able to produce quantitative data [24], full resolution of the isomers of lower polyglycerols was not achieved.…”

Section: Figurementioning

confidence: 99%

“…To develop the column chromatographic purification of tri-and tetraglycerol, various solvent mixtures were investigated in preliminary TLC experiments: ethylacetate-isopropanol-acetone-methanol-water (50:15:15:16:4) (v:v) [23], benzene-methanol (8:3) (v:v) [17], acetone-butanol-water (5:4:1) (v:v) [26] and ethylacetate-isopropanol-water (7:2:1), (6:2:1), (6:3:1) and (5:2:1) (v:v) [22,26]. Only the latter solvent mixture seemed to be successful for an adequate separation of the polyglycerols present in the polyglycerol mixtures analysed.…”

Section: E V E L O P M E N T Of C O L U M N C H R O M a T O G R A Pmentioning

confidence: 99%

“…Many researchers have tried to analyse polyglycerol fatty acid esters using several chromatographic techniques including paper [14], thin-layer [15], column [16], gas [16,17], high-performance liquid [18,19] and supercritical fluid chromatography [20]. All these techniques were qualitative and in some cases even separation between the different classes ofpolyglycerol fatty acid esters was incomplete.…”

Section: Introductionmentioning

confidence: 99%

“…For analysis of the polyglycerols themselves, similar techniques have been used [ 17,[21][22][23][24][25]. In contrast to the …”

Section: Introductionmentioning

confidence: 99%

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Development of chromatographic method for the determination of degree of polymerisation of polyglycerols and polyglycerol fatty acid esters

2000

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SummaryFrom polyglycerol samples, pure standards of tri and tetraglycerol were obtained using a column chromatographic technique. Polyglycerols were derivatised to trimethyl silyl derivatives to obtain gas chromatographic identification of all linear, branched and cyclic diglycerol isomers and all linear and branched triglycerols. Moreover, quantitative gas chromatographic analysis of the di-, tri-and tetraglycerol content of a polyglycerol sample was developed. Finally a method to characterise, on a quantitative basis, the polyglycerol content ofpolyglycerol fatty acid esters was developed. It consisted of saponifying the esters, without affecting the degree of polymerisation of the polyglycerols, followed by gas chromatographic analysis of the isolated polyglycerol fraction.

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Section: Figurementioning

confidence: 99%

Section: E V E L O P M E N T Of C O L U M N C H R O M a T O G R A Pmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

“…For analysis of the polyglycerols themselves, similar techniques have been used [ 17,[21][22][23][24][25]. In contrast to the …”

Section: Introductionmentioning

confidence: 99%

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Development of chromatographic method for the determination of degree of polymerisation of polyglycerols and polyglycerol fatty acid esters

2000

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“…On the other hand, the use of orthogonal protective groups and of selective reactions yielded a large range of amphiphilic molecules bearing different kind of fatty chain (length, unsaturations, position on the polar head, ester or ether bond). Jusqu'à présent, la multiplicité des structures produites ainsi que l'absence d'étalon de référence a véritablement freiné les méthodes d'analyses chromatographiques [4][5][6][7]. Les études des propriétés physicochimiques ont également été uniquement réalisées sur ces mélanges de dérivés d'oligoglycérols [8,9].…”

Section: Discussionunclassified

Synthèse de polyglycérols linéaires et cycliques. Tensioactifs polyglycérylés : synthèse et caractérisations

Debaig¹,

Benvegnu²,

Plusquellec³

2002

OCL

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Résumé : Le glycérol est l'un des principaux sous-produits de l'oléochimie. Un des axes de recherche pour valoriser ce co-produit demeure la production de polyglycérols et d'esters de polyglycérols, tensioactifs non ioniques. Cependant, ceux-ci sont généralement préparés industriellement dans des conditions drastiques (milieu caustique et températures élevées), générant des mélanges complexes d'oligomères de composition moléculaire mal définie. C'est dans ce contexte qu'un programme européen a été initié dans le but de préparer des échantillons standard et d'établir des corrélations structure/activité (analyse, performances, environnement) par une étude plus fondamentale sur les oligomères du glycérol et leurs esters. Notre travail a consisté à mettre au point des voies d'accès à des oligoglycérols linéaires et cycliques, de degré 2 à 5, ainsi que des monoesters et monoéthers d'acides gras, de structure parfaitement définie, en privilégiant des synthèses courtes et efficaces pour obtenir des échantillons de plusieurs grammes. Les stratégies pour les structures linéaires reposent dans un premier temps sur des synthèses convergentes impliquant l'ouverture régiospécifique d'époxydes. La préparation de dimères cycliques du glycérol repose sur des réactions d'iodocyclisation, alors que les oligomères cycliques de degré 3 à 5 ont été préparés via la condensation de deux fragments linéaires. Dans un deuxième temps, le choix de groupes protecteurs orthogonaux et de réactions sélectives a permis de synthétiser une gamme de molécules amphiphiles de structure définie, en faisant varier aussi bien la tête polaire (nombre d'unités glycérol impliquées) que la chaîne hydrophobe (longueur, insaturation, position sur la tête polaire, liaison chimique ester ou éther). Summary :Glycerol is one of the main by-products of oleochemistry. In order to develop the possible uses of this by-product, research can focus on the production of polyglycerols and their non-ionic surfactants. However, they are usually prepared under drastic conditions (caustic media and high temperatures) leading to complex mixtures of undefined oligomers. In this context, a European Program started to prepare authentic standards of oligomers of glycerol as well as corresponding surfactants and to establish relations between structures and activity. This work describes a new means of access to authentic standards of linear and cyclic oligoglycerols and their mono-esters or mono-ethers with well-defined structures and determined degrees of polymerisation from 2 to 5, through short and efficient syntheses allowing further scaling up. On the one hand, linear oligomers were obtained by means of a convergent approach based on regioselective opening of epoxides. Iodocyclisation reactions involving unsaturated alcohols permitted to build cyclic diglycerols, whereas larger cycles were prepared thanks to the condensation of two linear fragments. On the other hand, the use of orthogonal protective groups and of selective reactions yielded a large range of amphiphilic molec...

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