Bio–based Pentenoic Acids as Intermediates to Higher Value‐Added Mono‐ and Dicarboxylic Acids

Nobbs, James D.; Zainal, Nur Zahirah Binte; Tan, Jozel; Drent, Eite; Stubbs, Ludger P.; Li, Chuanzhao; Lim, Sharon; Kumbang, Daniel G. A.; Meurs, Martin van

doi:10.1002/slct.201600136

Cited by 30 publications

(31 citation statements)

References 42 publications

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“…[27] Further improvements in reactivity were achieved by introducing halide-containing additives,for example,CuCl 2 ,HCl, or LiCl, or mixtures of them. [51,52] However,i nt his patent the stability of the recycled catalyst is not reported and it is only stated that the catalyst system was "almost exclusively detected in the organic phase". In this respect, the groups of Monflier and later on Ionescu investigated the recyclability of watersoluble Pd-catalysts.…”

Section: Introductionmentioning

confidence: 99%

“…[48,49] While the recycling of the catalyst was possible up to five times without significant loss of activity,t he general protocol is limited to water-soluble substrates.N otably,D rent et al at Shell claimed the possibility of catalyst recyclingusing 1,2-bis((di-tert-butylphosphanyl)methyl)benzene (d t bpx; L18,w hich was previously described by Shaw [50] )f or continuous adipic acid generation from water-soluble pentenoic acids. [51,52] However,i nt his patent the stability of the recycled catalyst is not reported and it is only stated that the catalyst system was "almost exclusively detected in the organic phase". At this point, it should be also noted that in contrast to well-established alkoxycarbonylations,the stability of the phosphine ligands in hydroxycarbonylations and thus the possibility for ligand recycling, is much more problematic.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation

et al. 2019

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The synthesis of carboxylica cids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers,c osmetics, pharmaceuticals,a grochemicals,a nd other manufactured chemicals.A lthough hydroxycarbonylations of olefins have been knownf or more than 60 years,c urrently knownc atalyst systems for this transformation do not fulfill industrial requirements,for example,stability.Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins,including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems,aswell as terminal alkenes,into the corresponding carboxylic acids in excellent yields.T he outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-tosuccess is the use of abuilt-in-base ligand under acidic aqueous conditions.This catalytic system is expected to provide abasis for new cost-competitive processes for the industrial production of carboxylic acids.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation

et al. 2019

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“…Because of the enormous use of petroleum, hydrogen and nitric acid in the current process, the production of adipic acid from biomass has been intensively investigated in these days. Other production methods of adipic acid from biomass include (i) conversion of hydrocarbons produced by BTL (biomass to liquid; combination of biomass gasification and Fischer-Tropsch synthesis) [77] in petrochemical processes, (ii) production of K-A oil by reduction of biomass pyrolysis oil (bio-oil) [78][79][80][81][82][83], (iii) direct production of adipic acid by fermentation [84], (iv) hydrodeoxygenation of sugar acids produced by oxidation of sugars [85][86][87][88][89][90][91][92], (v) extension of carbon chain of C5 biomass-derived platform chemicals such as γ-valerolactone by hydroformylation or carboxylation [93][94][95][96], and (vi) oxidative cleavage of 1,2-difunctionalized cyclohexanes produced by reduction of bio-oil [97][98][99][100]. Low yield from raw biomass (methods (i), (ii), (iii) and (vi)) and large number of steps (methods (i), (ii), (9) (v) and (vi)) are the main problems of these methods.…”

Section: Comparison With Systems Using Other Biomass-derived Substratesmentioning

confidence: 99%

Reductive Conversion of Biomass-Derived Furancarboxylic Acids with Retention of Carboxylic Acid Moiety

Nakagawa

Yabushita

Tomishige

2021

Trans. Tianjin Univ.

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Catalytic reduction systems of 2-furancarboxylic acid (FCA) and 2,5-furandicarboxylic acid (FDCA) with H2 without reduction of the carboxyl groups are reviewed. FCA and FDCA are produced from furfural and 5-hydroxymethylfurfural which are important platform chemicals in biomass conversions. Furan ring hydrogenation to tetrahydrofuran-2-carboxylic acid (THFCA) and tetrahydrofuran-2,5-dicarboxylic acid (THFDCA) easily proceeds over Pd catalysts. Hydrogenolysis of one C–O bond in the furan ring produces 5-hydroxyvaleric acid (5-HVA) and 2-hydroxyadipic acid. 2-Hydroxyvaleric acid is not produced in the reported systems. 5-HVA can be produced as the lactone form (δ-valerolactone; DVL) or as the esters depending on the solvent. These reactions proceed over Pt catalysts with good yields (~ 70%) at optimized conditions. Hydrogenolysis of two C–O bonds in the furan ring produces valeric acid and adipic acid, the latter of which is a very important chemical in industry and its production from biomass is of high importance. Adipic acid from FDCA can be produced directly over Pt-MoOx catalyst, indirectly via hydrogenation and hydrodeoxygenation as one-pot reaction using the combination of Pt and acid catalysts such as Pt/niobium oxide, or indirectly via two-step reaction composed of hydrogenation catalyzed by Pd and hydrodeoxygenation catalyzed by iodide ion in acidic conditions. Only the two-step method can give good yield of adipic acid at present.

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“…[4a] The first step ring-opening of GVL has been successfully realized at high temperature. [99] Subsequently, the PEAs distilled in the first step are reacted with the Pd catalyst under the reaction conditions of 105 °C, 5 h and 60 bar CO. Except for the unreacted GVL, AA was the only product that could be detected by 13 C NMR and GC analysis.…”

Section: Preparation Of Aa From Gvlmentioning

confidence: 99%

Sustainable Routes for the Synthesis of Renewable Adipic Acid from Biomass Derivatives

Lang

2021

ChemSusChem

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Adipic acid (AA) is a key industrial dicarboxylic acid intermediate used in nylon manufacturing. Unfortunately, the traditional process technology is accompanied by serious environmental pollution. Given the growing demand for adipic acid and the desire to reduce its negative impact on the environment, considerable efforts have been devoted to developing more green and friendly routes. This Review is focused on the latest advances in the sustainable preparation of AA from biomassbased platform molecules, including 5-hydroxymethylfufural, glucose, γ-valerolactone, and phenolic compounds, through biocatalysis, chemocatalysis, and the combination of both.Additionally, the development of state-of-the-art catalysts for different catalytic systems systematically is discussed and summarized, as well as their reaction mechanisms. Finally, the prospects for all preparation routes are critically evaluated and key technical challenges in the development of green and sustainable processes for the manufacture of AA are highlighted. It is hoped that the green adipic acid synthesis pathways presented can provide insights and guidance for further research into other industrial processes for the production of nylon precursors in the future.

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Bio–based Pentenoic Acids as Intermediates to Higher Value‐Added Mono‐ and Dicarboxylic Acids

Cited by 30 publications

References 42 publications

Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation

Synthesis of Carboxylic Acids by Palladium‐Catalyzed Hydroxycarbonylation

Reductive Conversion of Biomass-Derived Furancarboxylic Acids with Retention of Carboxylic Acid Moiety

Sustainable Routes for the Synthesis of Renewable Adipic Acid from Biomass Derivatives

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