Catalytic cleavage of methyl oleate or oleic acid

Köckritz, Angela; Blumenstein, Michael; Martin, Andreas

doi:10.1002/ejlt.200900103

Cited by 57 publications

(44 citation statements)

References 17 publications

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“…A more selective alternative is the aerobic cleavage of OA to AA in the presence of an aldehyde as sacrifying agent [82][83][84]. OsO 4 or osmate, RuO 2 , or Ru/(NH 4 ) 6 H 3 PV 6 Mo 6 O 40 were suitable catalysts, AA yield was isolated up to 95%, but the formation of stoichiometric by-products seems to be a disadvantage for a technical-scale process.…”

Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

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114

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Section: Direct Cleavage Of Monoenic Fatty Acids and Estersmentioning

confidence: 99%

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Köckritz

Martin

2010

Euro J Lipid Sci & Tech

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114

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“…Auto-oxidation of fatty acid proceeds through two stages that are promoted by the reactive hydrogen atom on the allylic position of the molecules. [23][24][25][26] As the water evaporates after film application, the amount of oxygen dissolved in the polymer matrix increases. The oxygen abstracts an allylic hydrogen from the long hydrocarbon fatty acid moieties to form a fatty alkyl radical which reacts with oxygen to form a hydroperoxide and conjugated double bonds (Scheme 1).…”

Section: Vomm Copolymer Characterizationmentioning

confidence: 99%

Emulsion Copolymerization of Vegetable Oil Macromonomers Possessing both Acrylic and Allylic Functionalities

Kaya

Mendon

Delatte

et al. 2013

Macromolecular Symposia

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Summary: A soybean oil-based vegetable oil macromonomer (VOMM) was incorporated as a comonomer into an all-acrylic copolymer via semi-continuous emulsion polymerization. Structurally, VOMMs are comprised of long hydrocarbon fatty acid moieties with allylic double bonds which enable auto-oxidative crosslinking at ambient temperature. VOMMs facilitate low temperature film formation and the fatty acid chains tethered to the polymer backbone auto-oxidize upon film formation to yield crosslinked films. Latexes with varying VOMM levels were synthesized to elucidate the effect of VOMMs on the pre-cure and post-cure glass transition temperature (T g ) and minimum film formation temperature (MFT). Thermoplastic control latexes (without VOMM) were also synthesized via copolymerization of butyl acrylate and methyl methacrylate. This paper details the characterization performed to validate and quantify the VOMM allylic unsaturation retention before, during, and after polymerization, and to quantify and confirm the increase in T g resulting from auto-oxidative crosslinking via solid state 13 C nuclear magnetic resonance spectroscopy and differential scanning calorimetry.

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“…It can be used for processes involving C=C transformations, such as epoxidation, hydroxylation and oxidative cleavage. Oxidative scission is a particularly attractive process, as it generates C9 products, such as aldehydes (Pouilloux et al, 2014) and acids (Godard et al, 2011;Köckritz et al, 2010). These short-chain aldehydes and acids are particularly useful platform molecules for the preparation of numerous bio-based products.…”

Section: Oxidative Cleavage Of Monounsaturated Acidsmentioning

confidence: 99%

From crops to products for crops: preserving the ecosystem through the use of bio-based molecules

Godard¹,

Satgé-De²,

Vedrenne³

et al. 2016

OCL

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-In a context of dwindling oil reserves and environmental pressures, the chemical industry needs to innovate by developing new processes for producing bioproducts from raw plant materials. Unsaturated fatty acids from vegetable oils constitute a highly promising renewable resource that can be used to diversify productions, decreasing reliance on petroleum. A starting material rich in oleic acid has been obtained through the selection of high-oleic sunflower varieties and enzymatic hydrolysis of the oil they produce. The double bonds of this unsaturated raw material have been cleaved in green oxidizing conditions involving a biphasic lipophilic-aqueous system including hydrogen peroxide as an oxidant and a peroxo-tungsten complex Q 3 {PO 2 [WO(O 2 ) 2 ] 4 } as a phase-transfer catalyst (PTC) and co-oxidant. This PTC efficiently transferred oxygen to the substrate in the lipophilic phase. A mono-acid (pelargonic acid) and a di-acid (azelaic acid), with shorter, unusual hydrocarbon chains not present in the natural state, were synthesized and purified through an intensive process. Pelargonic acid was then formulated as an environmentally friendly biocontrol agent for weeds. We extended this green process of oxidative scission to other fatty acids and derivatives, to obtain other short-chain acids with diverse potential applications. This production chain (crops, reaction and purification processes, products, applications) is based on a sustainable development strategy. Keywords:Oxidative scission / oleic acid / green process / ecodesign / biocontrol Résumé -De la plante aux bioproduits destinés au biocontrôle : préserver l'écosystème par l'utilisation de molécules biosourcées. Dans un contexte de diminution des réserves fossiles et de pressions réglementaires et environnementales, l'industrie chimique tend à innover en développant de nouveaux procédés pour la production de bioproduits d'origine végétale. Les acides gras insaturés d'une huile végétale constitue une ressource renouvelable prometteuse qui peut être utilisée pour diversifier les productions et réduire la dépendance vis-à-vis du pétrole. Dans cet article, une matière première riche en acide oléique a été obtenue par l'hydrolyse enzymatique de l'huile de tournesol hautement oléique, obtenue par sélection variétale. Les doubles liaisons de cette matière première insaturée ont été clivées dans des conditions oxydantes impliquant un système biphasique aqueux-lipophile, avec le peroxyde d'hydrogène comme oxydant et le complexe peroxo-tungtène Q 3 {PO 2 [WO(O 2 ) 2 ] 4 } comme catalyseur de transfert de phase (CTP) et cooxydant. Ce CTP a permis d'assurer un transfert efficace vers le substrat en phase lipophile. Un mono-acide (acide pélargonique) et un di-acide (acide azélaïque) à chaînes impaires plus courtes, peu présentes à l'état naturel, ont été ainsi synthétisés et purifiés grâce à un procédé intensifié. L'acide pélargonique a été formulé en tant qu'agent de biocontrôle écocompatible. Ce procédé vert de scission oxydante a été appliqué à d'autr...

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Catalytic cleavage of methyl oleate or oleic acid

Cited by 57 publications

References 17 publications

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Synthesis of azelaic acid from vegetable oil‐based feedstocks

Emulsion Copolymerization of Vegetable Oil Macromonomers Possessing both Acrylic and Allylic Functionalities

From crops to products for crops: preserving the ecosystem through the use of bio-based molecules

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