Recyclable process for sustainable adipic acid production in microemulsions

Blach, Philippe; Boström, Zebastian; Franceschi‐Messant, Sophie; Lattes, Armand; Pérez, Emile; Rico‐Lattes, Isabelle

doi:10.1016/j.tet.2010.06.093

Cited by 31 publications

(34 citation statements)

References 56 publications

(5 reference statements)

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“…This is important, since tungsten-based catalysts are well known to promote epoxidation reactions or carbon-carbon double bond cleavage hydrogen peroxide based processes. [29][30][31][32][33] Hydroxyl groups also remained intact under these conditions (entry 16) and the corresponding sulfoxide was obtained in 93.9% of yield. The reaction times required for sulfoxide formation ranged from 1.5 to 4 h for all substrates except for diphenyl sulfide, which took 7 h and led to the lowest yield (entry 14).…”

Section: Resultsmentioning

confidence: 98%

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

Ma¹,

Ou²,

Han³

et al. 2012

J. Braz. Chem. Soc.

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Uma sistema catalítico heterogêneo de peroxotungstato realizado em líquido iônico (IL) tipo escova foi sintetizado e aplicado na oxidação seletiva de sulfetos a temperatura ambiente e usando peróxido de hidrogênio 30 wt.% como oxidante terminal e água como solvente. Nenhum cosolvente orgânico ou outro aditivo foi necessário e a reação ocorre com uma quantidade de 1,5-2,0 mol% (baseado no W) de catalisador. Sulfetos alifáticos e aromáticos foram transformados de maneira eficiente e seletiva em seus respectivos sulfóxidos ou sulfonas pelo controle dos equivalentes de peróxido de hidrogênio. Grupos funcionais sensíveis à oxidação, tais como ligações duplas e hidroxila, não foram afetados mesmo com excesso de peróxido de hidrogênio. O catalisador foi recuperado após a reação via filtração e reutilizado pelo menos oito vezes sem perda significativa de atividade.An efficient and reusable heterogeneous catalytic assembly of peroxotungstate held in a ionic liquid (IL) brush was synthesized and an environmentally-friendly procedure was developed for selective oxidation of sulfides at room temperature using 30 wt.% hydrogen peroxide as the terminal oxidant and water as a sole solvent. No organic co-solvent or other additive was needed. A 1.5-2.0 mol% (based on W atom) loading catalyst was found to be sufficient for a smooth and clean reaction. Both aliphatic and aromatic sulfides were efficiently and selectively transformed into their respective sulfoxides or sulfones by simply controlling of equivalents of hydrogen peroxide. In addition to the high catalytic activity, the catalyst exhibits excellent chemoselectivity. Sensitive functional groups, such as double bond and hydroxyl, remained under the oxidation conditions the reaction even with an excess hydrogen peroxide. The catalyst was easily recovered (via simple filtration) and reused at least eight times without a noticeable loss of activity.

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Section: Resultsmentioning

confidence: 98%

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

Ma¹,

Ou²,

Han³

et al. 2012

J. Braz. Chem. Soc.

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“…38 Alternatively, microemulsions made of benzalkonium chloride surfactants have been used to avoid the need for phase-transfer agents by providing a homogeneous reaction medium for cyclohexene as the oil phase and H 2 O 2 as the aqueous phase. 39,40 Several other tungstate-based catalysts have been reported as well, including oxotungsten-containing SBA-15, 41 surfactant-type peroxotungstates, 42 [BMIm] 2 WO 4 supported on silica sulphamic acid, 43 As part of the ongoing effort to understand the mechanistic pathway of the oxidative cleavage reaction, Lee et al explored titanium framework-substituted aluminophosphate (TAPO-5) as another catalyst for the oxidation of cyclohexene to AA. 48 Nuclear magnetic resonance (NMR) and gas chromatography coupled with mass spectrometry (GC-MS) analyses provided insight into the formation of intermediates and shed light on the mechanism of the overall reaction (Scheme 3).…”

Section: Hydrogen Peroxide As An Oxidantmentioning

confidence: 99%

Emerging catalytic processes for the production of adipic acid

Vyver

Román‐Leshkov

2013

Catal. Sci. Technol.

276

216

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Research efforts to find more sustainable pathways for the synthesis of adipic acid have led to the introduction of new catalytic processes for producing this commodity chemical from alternative resources. With a focus on the performance of oxygen and hydrogen peroxide as preferred oxidants, this minireview summarizes recent advances made in the selective oxidation of cyclohexene, cyclohexane, cyclohexanone and n-hexane to adipic acid. Special attention is paid to the exploration of catalytic pathways involving lignocellulosic biomass-derived chemicals such as 5-hydroxymethylfurfural, D-glucose, g-valerolactone and compounds representative of lignin and lignin-derived bio-oils.Scheme 1 Simplified reaction scheme of the current industrial process for AA production by catalytic oxidation of KA oil with nitric acid. Scheme 6 Proposed mechanism for the transformation of cyclohexanone to e-caprolactone over HMSnP-1 in the presence of O 2 . 96 Scheme 7 Baeyer-Villiger oxidation of cyclohexanone with H 2 O 2 . Scheme 8 Hydrogenation of 5-hydroxymethylfurfural to 2,5-di-hydroxymethyltetrahydrofuran with RANEY s -Ni catalysts. 150 Scheme 10 Schematic illustration of the active sites on rhodium-rhenium catalysts for the hydrogenolysis of 2-THPM. Adapted from ref. 152.Scheme 9 Consecutive reaction pathway for the conversion of 2,5-di-hydroxymethyltetrahydrofuran to tetrahydro-2H-pyran-2-ylmethanol via 1,2,6-hexanetriol. 150

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“…H 2 O 2 is well known as an oxidant and is used in several chemical and industrial processes that make use of this property. [18][19][20][21][22][23] It has even been used as the oxidant in other types of fuel cells where it has been shown to perform even better than O 2 in some cases. [24][25][26][27] However, H 2 O 2 is quite unique when applied to fuel cells because it can be both oxidised and reduced, with each process occurring at a different electrochemical potential (NHE ¼ normal hydrogen electrode):…”

Section: Introductionmentioning

confidence: 99%

Progress Towards Direct Hydrogen Peroxide Fuel Cells (DHPFCs) as an Energy Storage Concept

McDonnell-Worth¹,

MacFarlane²

2018

Aust. J. Chem.

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This review introduces the concept of direct H2O2 fuel cells and discusses the merits of these systems in comparison with other ‘clean-energy’ fuels. Through electrochemical methods, H2O2 fuel can be generated from environmentally benign energy sources such as wind and solar. It also produces only water and oxygen when it is utilised in a direct H2O2 fuel cell, making it a fully reversible system. The electrochemical methods for H2O2 production are discussed here as well as the recent research aimed at increasing the efficiency and power of direct H2O2 fuel cells.

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Recyclable process for sustainable adipic acid production in microemulsions

Cited by 31 publications

References 56 publications

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

A peroxotungstate-ionic liquid brush assembly: an efficient and reusable catalyst for selectively oxidizing sulfides with aqueous H2O2 solution in neat water

Emerging catalytic processes for the production of adipic acid

Progress Towards Direct Hydrogen Peroxide Fuel Cells (DHPFCs) as an Energy Storage Concept

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