Screening of solid acid catalysts for etherification of glycerol with isobutene under identical conditions

Bozkurt, Özge Deniz; Bağlar, Nur; Çelebi, Süleyman; Uzun, Alper

doi:10.1016/j.cattod.2019.07.025

Cited by 13 publications

(5 citation statements)

References 37 publications

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“…63 Figure 6c shows that the pH of the aqueous solution changed based on the contents of the HPPEP colloids in the solution; this pH change was easily indicated by the color change of the methyl red indicator. Based on acid−base titration, the acid proton density of the HPPEP colloids was estimated to be ∼0.26 mmol H + /g (Figure S23), higher and lower than those obtained using a zeolite-based solid acid catalyst (Zeolite Y (SiO 2 /Al 2 O 3 = 80): 0.13 mmol H + /g) 64 and a PS sulfonate-based solid acid catalyst (Amberlyst 15: 4.50 mmol H + /g; one of the strongest solid acid catalysts), 64 respectively. In terms of selectivity, which is one of the main issues in solid acid catalyst chemistry, the obtained moderateacid proton density is advantageous because it imparts a degree of selectivity that enables the reaction of specific molecules with a strong reactivity in the presence of other molecules with a weak reactivity.…”

Section: Resultsmentioning

confidence: 99%

Ecofriendly Multifunctional Monodisperse Spherical Polymer Colloids from Hyperbranched Poly(p-phenyl ester) Phenol

Lee

Jung

Jang

et al. 2022

ACS Appl. Polym. Mater.

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Multifunctional, monodisperse, and hyperbranched poly(p-phenyl ester) phenol (HPPEP) colloids are prepared using commercially available inexpensive monomers (i.e., terephthaloyl chloride (A 2 ) and phloroglucinol (B 3 )) via a simple condensation polymerization reaction (A 2 + B 3 ) at room temperature. Because of their symmetrical, rigid, highly branched, and cross-linked structure and the presence of the terminal phenolic units, the formation of highly monodisperse HPPEP colloids (coefficient of variation < 1.6%) can be realized under trimethylamine base conditions without any emulsifier (or surfactants) and expensive catalyst. Owing to their rigid aromatic and cross-linked structure, the HPPEP colloids exhibit excellent thermal, chemical, and mechanical resistances. Furthermore, the phenolic surface groups of HPPEP colloids enable the generation of highly negative surface charges (−60 mV) and catalytic protons (0.26 mmol H + /g) while enhancing surface functionality by chemically binding to red, green, and blue fluorescent dye molecules. Through carbonization, HPPEP colloids can be directly transformed into monodisperse porous carbon spheres with a large surface area (a s,BET = 644.99 m 2 g −1 ). Moreover, the HPPEP colloids can fully decompose into environmentally benign monomers after being exposed to an alkali environment.

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Section: Resultsmentioning

confidence: 99%

Ecofriendly Multifunctional Monodisperse Spherical Polymer Colloids from Hyperbranched Poly(p-phenyl ester) Phenol

Lee

Jung

Jang

et al. 2022

ACS Appl. Polym. Mater.

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“…In a recent detailed study, Bozkurt et al [108] compared the performance of more than 70 solid acid catalysts. Unmodified and modified ion exchange resins, zeolites, silica, and heteropolyacids were tested under similar conditions.…”

Section: Glycerol-isobutene Etherificationmentioning

confidence: 99%

Zeolite-based catalysis for isobutene conversion into chemicals and fuel additives. A review

Hulea¹

2022

Comptes Rendus. Chimie

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Isobutene (IB), the most reactive molecule in the C4 raffinate, is a raw material of great industrial significance. It is extensively used in the manufacturing process of rubber, fuel additives, fine chemicals, agricultural chemicals, plastics and antioxidants. Heterogeneous catalysts and particularly zeolites are playing a major role in these applications. The aim of this review is to examine the relevant processes involving IB as reagent and zeolites as acid catalysts. The following reactions are successively covered: Prins condensation, IB dimerization, IB-methanol/ethanol etherification, IB-glycerol etherification, IB amination, and phenol tert-butylation. While reasonably comprehensive and broad, the present survey is not necessarily exhaustive. The mechanistic aspects of the titled reactions, the role of zeolite catalysts and their topology/active sites on the product selectivity are mainly explored.

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“…As for the catalysts required, homogeneous acids, i.e., those that are soluble in glycerol, such as p-toluensulfonic acid or the heteropoly acid H 3 PW 12 O 40 , are much more active than the heterogeneous ones and allow obtaining significantly higher yields of di-and tri-tBGEs [16]. The interest in avoiding the use of the homogeneous acids due to corrosion, safety, and environmental issues has fostered the search for solid acid catalysts among which cation exchange resins with highly crosslinked structure, large pore zeolites, sulfonated mesostructured silicas and carbons, and supported tungstophosphoric acid have provided the best results with both IB [19][20][21][22][23][24][25] and TBA [19,[26][27][28][29][30][31][32]. These materials require a fine-tuning of their acid and textural properties in order to develop suitable catalytic activity and selectivity toward higher tBGEs; at the same time, they are also very sensitive to water, which solvates the hydrophilic active sites, rendering them poorly active.…”

Section: Introductionmentioning

confidence: 99%

Acid-Catalyzed Etherification of Glycerol with Tert-Butanol: Reaction Monitoring through a Complete Identification of the Produced Alkyl Ethers

Cornejo,

Reyero,

Campo

et al. 2023

Catalysts

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Higher tert-Butyl glycerol ethers (tBGEs) are interesting glycerol derivatives that can be produced from tert-butyl alcohol (TBA) and glycerol using an acid catalyst. Glycerol tert-butylation is a complex reaction that leads to the formation of five tBGEs (two monoethers, two diethers, and one triether). In order to gain insight into the reaction progress, the present work reports on the monitoring of glycerol etherification with TBA and p-toluensulfonic acid (PTSA) as homogeneous catalysts. Two analytical techniques were used: gas chromatography (GC), which constitutes the benchmark method, and 1H nuclear magnetic resonance (1H NMR), whose use for this purpose has not been reported to date. A method for the quantitative analysis of tBGEs and glycerol based on 1H NMR is presented that greatly reduced the analysis time and relative error compared with GC-based methods. The combined use of both techniques allowed for a complete quantitative and qualitative description of the glycerol tert-butylation progress. The set of experimental results collected showed the influence of the catalyst concentration and TBA/glycerol ratio on the etherification reaction and evidenced the intrinsic difficulties of this process to achieve high selectivities and yields to the triether.

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Screening of solid acid catalysts for etherification of glycerol with isobutene under identical conditions

Cited by 13 publications

References 37 publications

Ecofriendly Multifunctional Monodisperse Spherical Polymer Colloids from Hyperbranched Poly(p-phenyl ester) Phenol

Ecofriendly Multifunctional Monodisperse Spherical Polymer Colloids from Hyperbranched Poly(p-phenyl ester) Phenol

Zeolite-based catalysis for isobutene conversion into chemicals and fuel additives. A review

Acid-Catalyzed Etherification of Glycerol with Tert-Butanol: Reaction Monitoring through a Complete Identification of the Produced Alkyl Ethers

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