Conversion of levulinic acid to levulinate ester biofuels by heterogeneous catalysts in the presence of acetals and ketals

Chaffey, Dawn R.; Bere, Takudzwa; Davies, Thomas E.; Apperley, David C.; Taylor, Stuart H.; Graham, Andrew E.

doi:10.1016/j.apcatb.2021.120219

Cited by 39 publications

(20 citation statements)

References 58 publications

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“…The reaction products, n -butyl levulinate (BL) and p seudo-n-butyl levulinate ( pseudo -BL) were detected by GC-MS techniques. Similar results were also observed by several authors ( Ciptonugroho et al, 2016 ; Chaffey et al, 2021 ). As shown in Figure 7A remarkable catalytic performance of TNTs-NHSO 3 H was observed since LA conversion (70.5%) with high selectivity (89.4%) to BL was achieved.…”

Section: Resultssupporting

confidence: 92%

Titania Nanotubes-Bonded Sulfamic Acid as an Efficient Heterogeneous Catalyst for the Synthesis of n-Butyl Levulinate

et al. 2022

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The titania nanotubes-bonded sulfamic acid (TNTs-NHSO3H) catalyst was designed and successfully fabricated by the post-synthesis modification method. The as-prepared catalyst was characterized by a variety of characterization techniques, including Fourier transform infrared (FT-IR) spectroscopy, X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM), scanning electron microscopy (SEM), X-ray diffraction (XRD) analysis, and thermogravimetry-differential thermal gravimetry (TG-DTG). The crystal structure of the TNTs still maintained during the modification process. Although the BET surface area was decreased, the amount of Brønsted acid sites can be efficiently fabricated on the TNTs. The catalytic activity of TNTs-NHSO3H was examined for the synthesis of n-butyl levulinate (BL) from levulinic acid (LA) and furfuryl alcohol (FA). A relatively high selectivity (99.6%) at 99.3% LA conversion was achieved for esterification of levulinic acid owing to the strong Brønsted acidity sites. And also, the TNTs-NHSO3H catalyst exhibited a higher reactivity for alcoholysis of FA and the yield of BL reached 90.4% with 100% FA conversion was obtained under the mild conditions.

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Section: Resultssupporting

confidence: 92%

Titania Nanotubes-Bonded Sulfamic Acid as an Efficient Heterogeneous Catalyst for the Synthesis of n-Butyl Levulinate

et al. 2022

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“…Here, the reaction mechanisms could be explained as follows: (I) FF was converted to FA via transfer hydrogenation with the assistance of Lewis acid Ni−Al catalyst, (II) FA etherification was catalyzed by Lewis/ Brønsted acid sites from SO 3 H@Ni−Al to form EFE chemical, and (III) EFE was further converted to desired EL via a hydrolytic ring-opening process with the assistance of Brønsted acid sites on the catalyst. 36,37 This indicates that the synergistic effect of Brønsted and Lewis acid sites on SO 3 H@Ni−Al catalysts was very important for catalytic production of EL.…”

Section: ■ Results and Discussionmentioning

confidence: 96%

“…These behaviors should be described to further generation of GVL and humins’ products via second transfer hydrogenation and polymerization/condensation reactions, respectively, when excessive acidity with a L/B ratio of 0.17 existed in the SO 3 H@Ni–Al-(4) catalyst. Here, the reaction mechanisms could be explained as follows: (I) FF was converted to FA via transfer hydrogenation with the assistance of Lewis acid Ni–Al catalyst, (II) FA etherification was catalyzed by Lewis/Brønsted acid sites from SO 3 H@Ni–Al to form EFE chemical, and (III) EFE was further converted to desired EL via a hydrolytic ring-opening process with the assistance of Brønsted acid sites on the catalyst. , This indicates that the synergistic effect of Brønsted and Lewis acid sites on SO 3 H@Ni–Al catalysts was very important for catalytic production of EL. Based on these results, the SO 3 H@Ni–Al-(3) catalyst was chosen to be utilized in the next sections.…”

Section: Resultsmentioning

confidence: 99%

Rapid Transformation of Furfural to Biofuel Additive Ethyl Levulinate with In Situ Suppression of Humins Promoted by an Acidic-Oxygen Environment

Karnjanakom

Bayu

Samart

et al. 2021

ACS Sustainable Chem. Eng.

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Sustainable production of biofuel additive ethyl levulinate (EL) from biomass-derived furfural (FF) is an interesting way owing to its application in improving the diesel combustion process without the expense of octane number. In this study, a stable mesoporous SO 3 H@Ni−Al catalyst prepared via facile a hydrothermal-functionalization process was characterized and applied for ultrasound-assisted transformation of FF into EL using ethanol as a hydrogen donor. Interestingly, the formation of humins in the mixture solution and on the catalyst surface was effectively suppressed after introduction of an oxygen environment, resulting from an oxidative degradation reaction. The optimization process was carried out under catalyst acidity, ultrasonic power generation, and statistical design. As desired, a high yield of EL (∼97%, E a = 25.95 kJ/mol) without humins' formation was well achieved in a shorter reaction time (95 min) and at a low reaction temperature (112 °C), compared with a previous conventional reaction. Moreover, the introduction of oxygen strongly promoted the catalyst reusability with a slight reduction in its catalytic behavior, while selectivity/distribution in the liquid product had slight differentiation.

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“…171 The compound 5-formyl-2-furancarboxylic acid (FFCA) (7) can be further oxidized into FDCA (6), which is a chain termination agent in polyethylene material formation. 172 The decomposition product EL (9) can be used in the food and flavor industry, 173 and it has also been reported to be useful as a fuel additive. 46 It should be noted that FDCA can replace the oil based terephthalic acid in polymer production because it has a molecular structure (two carboxyl groups) similar to that of terephthalic acid.…”

Section: Applications Of 5-emfmentioning

confidence: 99%

Critical Assessment of Reaction Pathways for Next-Generation Biofuels from Renewable Resources: 5-Ethoxymethylfurfural

Guo

Dowaki

Shen

et al. 2022

ACS Sustainable Chem. Eng.

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Renewable resources must be upgraded to platform chemicals and biofuels, especially furanic compounds such as 5-hydroxymethylfurfural (5-HMF) and 5-ethoxymethylfurfural (5-EMF), to meet the needs of a sustainable society. This review examines chemocatalytic approaches to 5-EMF via alcoholysis of 5-(halomethyl)furfural or etherification of 5-HMF with attention being given to direct catalytic conversion of biomass-derived materials into 5-EMF. Emphasis is placed on the reaction mechanisms and pathways with either homogeneous or heterogeneous catalysts to provide recommendations for catalytic system development. A multicriteria assessment evaluation tool as a sustainability assessment method for the synthesis of 5-EMF routes from biomass is given. Potential research directions include the direct synthesis of 5-EMF from biomass-derived compounds in innovative reaction systems and technoeconomic studies on 5-EMF production.

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Conversion of levulinic acid to levulinate ester biofuels by heterogeneous catalysts in the presence of acetals and ketals

Cited by 39 publications

References 58 publications

Titania Nanotubes-Bonded Sulfamic Acid as an Efficient Heterogeneous Catalyst for the Synthesis of n-Butyl Levulinate

Titania Nanotubes-Bonded Sulfamic Acid as an Efficient Heterogeneous Catalyst for the Synthesis of n-Butyl Levulinate

Rapid Transformation of Furfural to Biofuel Additive Ethyl Levulinate with In Situ Suppression of Humins Promoted by an Acidic-Oxygen Environment

Critical Assessment of Reaction Pathways for Next-Generation Biofuels from Renewable Resources: 5-Ethoxymethylfurfural

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