New Environmentally Friendly Oxidative Scission of Oleic Acid into Azelaic Acid and Pelargonic Acid

Godard, Anaïs; de, Pascale; Thiébaud‐Roux, Sophie; Vedrenne, Emeline; Mouloungui, Zéphirin

doi:10.1007/s11746-012-2134-7

Cited by 57 publications

(71 citation statements)

References 15 publications

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“…The temperature of 70 o C is an effective temperature, not only to get a good reaction rate but also to make the oil turn out to be more dilute so it is easier to experience the reaction 8 . In addition to avoiding substrate losses and catalysts required a temperature that is not too high 3 . The interaction of catalyst concentration and reaction temperature will obtain the higher oleic acid conversion at 1.45% (w/wOA) catalyst concentration and 70 o C of reaction temperature.…”

Section: Interaction Effect and Optimization Processmentioning

confidence: 99%

“…The azelaic acid has anti-inflammatory and anti-bacterial properties so that azelaic acid has widely used in the pharmaceuticals industry as an anti-acne agent and stimulator of hair growth [1,2 . In commercial usage, the azelaic acid is also widely used in polymers industry as a polyester, polyamides, and polyurethane layers compounds 3,4 . Not only the azelaic acid, pelargonic acid can also be produced in this oxidation-breakdown reaction.…”

Section: Introductionmentioning

confidence: 99%

“…Oxidants such as sodium periodate, peroxomonosulfate, para-acetate acid and tertbutyl hydroperoxide are often used in this reaction because they are strong oxidizing reagents even without the addition of transition metals but produce unsustainable waste 3,9 . Hydrogen peroxide (H 2 O 2 ) is an attractive alternative oxidant because it does not produce waste at the end of the reaction but almost requires transition metal to be able to oxidize substrates with maximum 10,11 .…”

Section: Introductionmentioning

confidence: 99%

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Optimization of A Two-Step Method to Synthesize Azelaic Acid from Oleic Acid

Masyithah

Ginting

2018

Orient. J. Chem

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The present study deals with the oxidative cleavage of oleic acid (OA) using hydrogen peroxide and tungstic acid as a catalyst to produce azelaic acid. A two-step method has been expanded for the optimization of a new route of azelaic acid synthesis with the addition of sodium hypochlorite as the co-oxidation. The Central Composite Design (CCD) and Response Surface Methodology (RSM) were performed to optimize the production of azelaic acid. The interaction effect among catalyst concentration, substrate molar ratio and temperature were done for optimization the conversion of oleic acid. Maximum oleic acid conversion of 99.11% was reached at substrate molar ratio of 4/1 (H 2 O 2 /OA), a catalyst concentration of 1.5% (w/wOA) and temperature of 70 o C. The GC analysis shows that the yield of azelaic acid is 44.54% and pelargonic acid is 34.12%. These results indicate that the proposed process show a good strategy for the synthesis of azelaic acid from oxidative cleavage of oleic acid.

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Section: Interaction Effect and Optimization Processmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Optimization of A Two-Step Method to Synthesize Azelaic Acid from Oleic Acid

Masyithah

Ginting

2018

Orient. J. Chem

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“…3). The best yields of AA and PA (81.5% and 86.1%, respectively), were obtained for heating at 85 • C for 5 h, with the AO/H 2 O 2 /[C 5 H 5 N(n-C 16 H 33 )] 3 {PO 4 [WO(O 2 ) 2 ] 4 } system, corresponding to a molar ratio of 50/250/1, coupled with in situ catalyst preparation (Godard et al, 2013b). It means that hexadecylpyridinium chloride was used for the preparation of the peroxo-tungten complex.…”

Section: Study Of a Process For The Oxidative Scission Of Oleic Acid mentioning

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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“…One of the most common classification systems concerns the type of conversion processes used, in this case being thermochemical and/or biochemical biorefineries [1][2][3][4][5][6][7].…”

Section: Introductionmentioning

confidence: 99%

Energy Opportunities from Lignocellulosic Biomass for a Biorefinery Case Study

et al. 2016

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This work presents some energy considerations concerning a biorefinery case study that has been carried out by the CRB/CIRIAF of the University of Perugia. The biorefinery is the case study of the BIT3G project, a national funded research project, and it uses the lignocellulosic biomass that is available in the territory as input materials for biochemical purposes, such as cardoon and carthamus. The whole plant is composed of several sections: the cardoon and carthamus seed milling, the oil refinement facilities, and the production section of some high quality biochemicals, i.e., bio-oils and fatty acids. The main goal of the research is to demonstrate energy autonomy of the latter section of the biorefinery, while only recovering energy from the residues resulting from the collection of the biomass. To this aim, this work presents the quantification of the energy requirements to be supplied to the considered biorefinery section, the mass flow, and the energy and chemical characterization of the biomass. Afterwards, some sustainability strategies have been qualitatively investigated in order to identify the best one to be used in this case study; the combined heat and power (CHP) technology. Two scenarios have been defined and presented: the first with 6 MWt thermal input and 1.2 MWe electrical power as an output and the second with 9 MWt thermal input and 1.8 MWe electrical power as an output. The first scenario showed that 11,000 tons of residual biomass could ensure the annual production of about 34,000 MWht, equal to about the 72% of the requirements, and about 9600 MWhe, equal to approximately 60% of the electricity demand. The second scenario showed that 18,000 tons of the residual biomass could ensure the total annual production of about 56,000 MWht, corresponding to more than 100% of the requirements, and about 14,400 MWhe, equal to approximately 90% of the electricity demand. In addition, the CO 2 emissions from the energy valorization section have been quantified and the possibility of re-using the CO 2 flow in order to produce methane is described.

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New Environmentally Friendly Oxidative Scission of Oleic Acid into Azelaic Acid and Pelargonic Acid

Cited by 57 publications

References 15 publications

Optimization of A Two-Step Method to Synthesize Azelaic Acid from Oleic Acid

Optimization of A Two-Step Method to Synthesize Azelaic Acid from Oleic Acid

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

Energy Opportunities from Lignocellulosic Biomass for a Biorefinery Case Study

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