Use of Ion-Exchange Resins in Alkylation Reactions

Lachter, Elizabeth R.; Rodrigues, Jorge A.; Mendonça, Roberta Helena; Ribeiro, Paula Salino; Villabona-Estupiñán, Santiago

doi:10.1007/978-3-030-06085-5_3

Cited by 6 publications

(4 citation statements)

References 115 publications

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“…Amberlite® CG‐50 has relatively moderate adsorption capability, followed by Amberlyst® 15. The reason behind the poor performance of the Amberlyst® 15 lies in the acidic nature of the resin which promotes mainly molecular adsorption as opposed to ion‐exchange adsorption in less acidic or even basic resins 28,29 . The adsorption behavior of Amberlite® IRA‐400 (Cl) demonstrates its potential to be used for in situ biophenol adsorption and is highlighted in the following section.…”

Section: Resultsmentioning

confidence: 99%

“…On the other hand, the highly acidic nature of Amberlyst® 15 led to complete TBA conversion with monoalkylated phenolic compounds accounting for the majority of product. It is worth mentioning here that, although Amberlyst® 15 has been studied previously for phenol alkylation reactions, research on using TBA as the alkylating agent for phenol alkylation in the presence of Amberlyst® 15, to the best of our knowledge, is not present in the open literature 29,32 . Since Amberlyst® 15 was found to significantly promote the formation of monoalkylated phenolic products, it thereafter became necessary to develop a deeper understanding of its kinetic behavior.…”

Section: Resultsmentioning

confidence: 99%

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Toward the coupling of microbial biosynthesis and catalysis for the production of alkylated phenolic compounds

Zuber

Wang

et al. 2020

AIChE Journal

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In the present study, petroleum-free production of alkylated phenols from glycerol was achieved by judicious use of microbial biosynthesis and heterogeneous catalysis with the aim to advance biomass conversion to industrially relevant chemical products. First, metabolically engineered bacterium Escherichia coli was adopted to convert glycerol to phenol. Biophenol was then extracted from the cell culture using select polymeric resins. Desorption of phenol was achieved with tertiary butyl alcohol, which serves also as a reactant in subsequent heterogeneous catalytic reaction. The adopted resins were also compared as catalysts for alkylation of phenol to tert-butyl phenolic products. Interestingly, the resins exhibited different phenol adsorption and catalytic reactivities. The holistic approach developed by this study offers a unique opportunity to synthesize end products directly from glycerol that cannot be achieved in such an efficient manner (i.e., low temperature, low pressure, and high selectivity) by using microbial biosynthesis or heterogeneous catalysis approaches alone.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Toward the coupling of microbial biosynthesis and catalysis for the production of alkylated phenolic compounds

Zuber

Wang

et al. 2020

AIChE Journal

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“…Heterogeneous catalysts besides being recyclable operate with little deactivation during transesterification [ 3 , 34 , 35 ]. Heterogeneous catalysts include sulphated zirconia and tungstated zirconia [ 98 ], zeolites and zeotype materials, mixed oxides (silica alumina), sulfonated polystyrene, ion exchange resins and hetero‐polyacids [ 65 , 66 ]. Zeolites and zeotype are naturally occurring in the form of crystalline aluminosilicates, interlinked with oxygen atoms; thus, forming a three dimensional molecular pore structure of equal sizes [ 67 ].…”

Section: Catalyst Classificationmentioning

confidence: 99%

A review of sustainable biodiesel production using biomass derived heterogeneous catalysts

Maroa

Inambao

2021

Engineering in Life Sciences

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The production of biodiesel through chemical production processes of transesterification reaction depends on suitable catalysts to hasten the chemical reactions. Therefore, the initial selection of catalysts is critical although it is also dependent on the quantity of free fatty acids in a given sample of oil. Earlier forms of biodiesel production processes relied on homogeneous catalysts, which have undesirable effects such as toxicity, high flammability, corrosion, by-products such as soap and glycerol, and high wastewater. Heterogeneous catalysts overcome most of these problems. Recent developments involve novel approaches using biomass and bio-waste resource derived heterogeneous catalysts. These catalysts are renewable, non-toxic, reusable, offer high catalytic activity and stability in both acidic and base conditions, and show high tolerance properties to water. This review work critically reviews biomass-based heterogeneous catalysts, especially those utilized in sustainable production of biofuel and biodiesel. This review examines the sustainability of these catalysts in literature in terms of small-scale laboratory and industrial applications in large-scale biodiesel and biofuel production. Furthermore, this work will critically review natural heterogeneous biomass waste and bio-waste catalysts in relation to upcoming nanotechnologies. Finally, this work will review the gaps identified in the literature for heterogeneous catalysts derived from biomass and other biocatalysts with a view to identifying future prospects for heterogeneous catalysts.Abbreviations: Al 2 O 3 , aluminum oxide; Ba, barium; BaO, barium oxide; C=O, carbonyl group; Ca, calcium; Ca 10 (PO 4 ) 6 (OH) 2 , HAP, hydroxyapatite; Ca 2 FeO 5 , calcium ferrite oxide; CaCO 3 , calcium carbonate; CaMg (CO 3 )2, dolomite; CaMnO 3 , orthorhombic perovskite; CaO, calcium oxide; CaO-CeO 2 , cerium (IV) oxide; CaTiO 3 , calcium titanate; CaZrO 3 , calcium zirconate; CH 3 OK, potassium methoxide; CH 3 ONa, sodium methoxide; CO 2 , carbon dioxide; COOH, carboxylic group; CsZrO 2 , chitoson zirconium oxide; DNA, deoxyribonucleic acid; FAAE, fatty acid alkyl esters; FAME, fatty acid methyl ester; Fe 3 O 4 , magnetic oxide (magnetite); FeCl 3 , ferric chloride; FFA, free fatty acid; FTIR, Fourier transform infrared; H 2 SO 4 , sulfuric acid; H 3 PO 4 , phosphoric acid; HCL, hydrochloric acid; HCs, hydrocarbons; HTHP, higher temperatures and pressure; K 2 CO 3 , potassium carbonate; K 2 O, potassium oxide; KF, potassium fluoride; KI, potassium iodide; KNO 3 , potassium nitrate; KOH, potassium hydroxide; La 2 O 3 , lanthanum oxide; Li/ZnO, lithium (Li) doped zinc oxide;

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“…The state of the art reveals that the range of reaction temperatures for the HAA of sylvan is fully compatible with the operating temperatures of standard ion-exchange resins (<150 °C), whose active sites can catalyze the reaction in Scheme . However, the number of studies for this reaction over acidic ion-exchange resins is scarce and limited to only a few resins, being Amberlyst 15 (A15) the most frequently used.…”

Section: Introductionmentioning

confidence: 99%

Catalytic Hydroxyalkylation/Alkylation of 2-Methylfuran with Butanal to Form a Biodiesel Precursor Using Acidic Ion-Exchange Resins

Ramírez

Bringué

Iborra

et al. 2020

Ind. Eng. Chem. Res.

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The catalytic hydroxyalkylation/alkylation of 2-methylfuran (2MF) with butanal has been investigated over several acidic ion-exchange resins within the temperature range 50−90°C and at a stoichiometric reactant molar ratio of 2MF/butanal (2:1). Butanal conversion increases with temperature and also the formation of undesired 2-methylfuran oligomers, leading to a decrease in yield of the target product. The highest butanal conversion (90%) is achieved at 50°C over Dowex 50Wx2 with a negligible formation of 2-methylfuran oligomers. The observed catalytic activity and final yield of the target product have been rationalized on the basis of morphological properties of resins and their dynamic behavior within the present reaction medium. The findings reveal that gel-type resins are more active and render higher product yields than their macroreticular congeners due to the enhanced accessibility to acid centers because of their improved ability to swell throughout the reaction. Macroreticular resins with a low cross-linking degree, e.g., Amberlyst39, also produce interesting catalytic results. The stability of the most promising catalyst has been evaluated after three reaction cycles, and the full reusability outcome speaks for its appropriateness as a potential catalyst for the studied process. 32 (2MF, also known as sylvan) 8 obtained from furfural has 33 recently attracted interests for biofuel production due to its 34 versatility to direct blending with gasoline 9 and diesel 10 and to 35 synthesize high-density biofuel. 11 For instance, the hydrox-36 yalkylation/alkylation (HAA) of sylvan with n-butanal 37 produces 1,1-bisylvylbutane (BSB), which can be transformed 38 into 6-propyl undecane by a subsequent hydrodeoxygenation 39 (HDO) step in series. Using platinum-supported carbon-or 40 alumina-based catalysts, a mixture of C9, C12, and C14 alkanes 41 can be obtained as an organic phase from the second reaction

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Use of Ion-Exchange Resins in Alkylation Reactions

Cited by 6 publications

References 115 publications

Toward the coupling of microbial biosynthesis and catalysis for the production of alkylated phenolic compounds

Toward the coupling of microbial biosynthesis and catalysis for the production of alkylated phenolic compounds

A review of sustainable biodiesel production using biomass derived heterogeneous catalysts

Catalytic Hydroxyalkylation/Alkylation of 2-Methylfuran with Butanal to Form a Biodiesel Precursor Using Acidic Ion-Exchange Resins

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