Polymers and surfactants on the basis of renewable resources

Warwel, Siegfried; Brüse, F.; Demes, C.; Kunz, Michael J.; Klaas, Mark Rüsch gen.

doi:10.1016/s0045-6535(00)00322-2

Cited by 174 publications

(134 citation statements)

References 14 publications

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“…Synthesis of phenolic epoxy prepolymers catalysed by lipase Epoxidized vegetable oils and derivatives, which are biodegradable, environmentally friendly and renewable resources, have recently found industrial applications as plasticizers, additives for PVC and rubber-like materials. [128][129][130][131][132] This kind of application is directly related to their chemical structure which consists of flexible and aliphatic chains. However, for advanced technological applications, epoxy resins with improved physico-chemical properties such as good thermal stability, low internal stress and high mechanical strength are required.…”

Section: Ii2 Factors Governing the Efficiency Of Lipase-catalyzed Epmentioning

confidence: 99%

The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

et al. 2014

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Lipases are versatile enzymes that can be used for various kinds of biocatalyzed reactions. Owing to their selectivity and their mild reaction conditions, they can be often considered as more interesting than classical chemical catalysts. Besides their application in oil and fat processes, these enzymes have proved to be very attractive for other lipase-catalyzed reactions. This review discusses the latest results where lipases are used for the epoxidation of lipid substrates (namely fatty acids and their derivatives) and phenolic compounds. This chemo-enzymatic process involves a two step synthesis where the biocatalyst acts as a perhydrolase to produce peracids, which then act as catalysts to epoxidize double bonds. Various factors govern the efficiency of the reaction in terms of kinetics, yields and enzyme stability.These parameters are evaluated and discussed herein. (Résumé d'auteur

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Section: Ii2 Factors Governing the Efficiency Of Lipase-catalyzed Epmentioning

confidence: 99%

The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

et al. 2014

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“…[15][16][17][18] For instance, the production of surfactants being efficient and presenting interesting properties such as biocompatibility and biodegradability 19,20 is a successful example of industrial conversion of vegetable oils into valuable chemicals. [21][22][23] The area of industrial conversion of oils into chemicals being wide, the reader's attention will now be focused only in the field of polymers. …”

Section: The Interest In Vegetable Oilsmentioning

confidence: 99%

Polymer precursors from catalytic reactions of natural oils

et al. 2012

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Dimethyl 1,19-nonadecanedioate is produced from the methoxycarbonylation of commercial olive, rapeseed or sunflower oils in the presence of a catalyst derived from [Pd 2 (dba) 3 ], bis(ditertiarybutylphosphinomethyl)benzene (BDTBPMB) and methanesulphonic acid (MSA). The diester is then hydrogenated to 1,19-nonadecanediol using Ru/1,1,1-tris-(diphenylphosphinemethyl)ethane (triphos). 1,19-Nonadecadienoic acid is hydrogenated to short chain oligoesters, which can themselves be hydrogenated to 1,19-nonadecanol by hydrogenation in the presence of water.

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“…The latter ones were obtained by metathesis of natural unsaturated fatty acid methyl esters with ethylene applying heterogeneous rhenium catalysts [9] or homogeneous ruthenium one-component-catalysts [10,11]. Methyl esters from high-oleic sunflower oil or 00-rapseed oil lead to 9-decenoic acid methyl ester; starting with methyl esters from high-erucic rapeseed oil or crambe oil 13-tetradecanoic acid methyl ester was available.…”

Section: Starting Materialsmentioning

confidence: 99%

Syntheses of surfactants from oleochemical epoxides

Warwel¹,

Brüse²,

Schier³

et al. 2001

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Résumé : Des surfactants d'hydrates de carbone peuvent être obtenus avec un bon rendement (jusqu'à 100 %) dans des conditions douces (à 70 °C, dans du méthanol ou dans un mélange de méthanol et d'eau) par des réactions des époxydes avec des polyhydroxyalcoylamines. Des réactions de N-méthylglucamine avec des oxydes d'alcoylènes supérieurs terminaux (C4-C18) ou des oxydes d'esters méthyliques d'acides gras à terminaisons insaturées amènent aux produits linéaires, tandis que des réactions avec de la N-dodécylglucamine ou de la glucamine amènent aux surfactants avec des structures en Y différentes. Les produits des réactions d'oxydes d'esters méthyliques d'acides gras à terminaisons insaturées subissent une saponification avec l'hydroxyde de sodium ou une hydrolyse enzymatique, ainsi on obtient respectivement des sels de sodium ou des acides, qui donnent des tensioactifs amphotères. L'étude des surfactants à différentes valeurs de pH montrent des propriétés tensioactives variées dans des solutions aqueuses. Pour quelques surfactants d'hydrates de carbone on trouve des petites c.m.c. (2-500 mg/l) et des tensions superficielles de 25-40 mN/m. Tandis que les produits de réactions des époxydes ont des pouvoirs moussants plutôt modérés, quelques bromohydrates correspondants ont de bonnes propriétés moussantes. Mots-clés : époxydes, glucamines, surfactants.Summary : Sugar-based surfactants were obtained in good yields (up to 100%) under mild conditions (70°C, methanol or mixtures of methanol and water) by ring-opening of terminal epoxides with aminopolyols, derived from glucose. Reaction of N-methyl glucamine with epoxides from evennumbered C4-C18 alpha-olefins or from terminal unsaturated fatty acid methyl esters leads to linear products, while corresponding reactions with N-dodecyl glucamine or glucamine yield surfactants with different Y-structures. Products obtained by conversion of omega-epoxy fatty acid methyl esters were saponificated with NaOH or hydrolyzed enzymatically to sodium salts or free acids respectively, which are amphoteric surfactants. Studies of the surfactants at different pH-values demonstrate different surface active properties in aqueous solutions. Critical micelle concentrations (c.m.c.) in a range between 2 and 500mg/l and surface tensions of 25-40mN/m were measured for several of the synthesized sugar-based surfactants. The ring-opening products are rather poor foamers, whereas some of the corresponding hydrobromides show good foaming properties.

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Polymers and surfactants on the basis of renewable resources

Cited by 174 publications

References 14 publications

The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

The use of lipases as biocatalysts for the epoxidation of fatty acids and phenolic compounds

Polymer precursors from catalytic reactions of natural oils

Syntheses of surfactants from oleochemical epoxides

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