Heterogeneous catalysis for the ketalisation of ethyl levulinate with 1,2-dodecanediol: Opening the way to a new class of bio-degradable surfactants

Freitas, Flávio A. de; Licursi, Domenico; Lachter, Elizabeth R.; Galletti, Anna Maria Raspolli; Antonetti, Claudia; Brito, Thamires C.; Nascimento, Regina Sandra Veiga

doi:10.1016/j.catcom.2015.10.011

Cited by 37 publications

(23 citation statements)

References 28 publications

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“…Moreover, the addition of an acid co-catalyst to Ru and [Ru/C + Re/C] systems has been considered because it is known that this acid component is able to activate not only the lactone ring opening, but also the internal dehydration of 1,4-PDO to 2-MeTHF [57][58][59]. For this purpose, in the first part of this work, niobium phosphate (NBP) has been selected as co-catalyst, thanks to its well-known acidic properties, which are preserved also in an aqueous medium, even at high temperatures [7,60]. This is an amorphous solid with strong Brønsted and medium-strong Lewis acid sites located at the surface, due to the presence of coordinatively unsaturated Nb 5+ species.…”

Section: Resultsmentioning

confidence: 99%

Cascade Strategy for the Tunable Catalytic Valorization of Levulinic Acid and γ-Valerolactone to 2-Methyltetrahydrofuran and Alcohols

et al. 2018

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A cascade strategy for the catalytic valorization of aqueous solutions of levulinic acid as well as of γ-valerolactone to 2-methyltetrahydrofuran or to monoalcohols, 2-butanol and 2-pentanol, has been studied and optimized. Only commercial catalytic systems have been employed, adopting sustainable reaction conditions. For the first time, the combined use of ruthenium and rhenium catalysts supported on carbon, with niobium phosphate as acid co-catalyst, has been claimed for the hydrogenation of γ-valerolactone and levulinic acid, addressing the selectivity to 2-methyltetrahydrofuran. On the other hand, the use of zeolite HY with commercial Ru/C catalyst favors the selective production of 2-butanol, starting again from γ-valerolactone and levulinic acid, with selectivities up to 80 and 70 mol %, respectively. Both levulinic acid and γ-valerolactone hydrogenation reactions have been optimized, investigating the effect of the main reaction parameters, to properly tune the catalytic performances towards the desired products. The proper choice of both the catalytic system and the reaction conditions can smartly switch the process towards the selective production of 2-methyltetrahydrofuran or monoalcohols. The catalytic system [Ru/C + zeolite HY] at 200 • C and 3 MPa H 2 is able to completely convert both γ-valerolactone and levulinic acid, with overall yields to monoalcohols of 100 mol % and 88.8 mol %, respectively.

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Section: Resultsmentioning

confidence: 99%

Cascade Strategy for the Tunable Catalytic Valorization of Levulinic Acid and γ-Valerolactone to 2-Methyltetrahydrofuran and Alcohols

et al. 2018

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“…LG found application as a reducing agent in the preparation of Fe(II), Co(II) and Ni(II) nanoparticles [8]. Freitas et al have demonstrated the importance of LG in the Ketalisation of ethyl levulinate resulting in a new class of biodegradable surfactants [9]. The use of LG as a constituent in skin cosmetics is the main driving force for the work presented here.…”

Section: Introductionmentioning

confidence: 88%

Substrate Influence on the Recrystallization of 1,2-dodecanediol: An Atomic Force Microscopy Study

Dora¹

2017

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1,2-dodecanediol otherwise known as lauryl glycol (LG), a skin conditioning agent in many skin cosmetics was recrystallized from chloroform on to a number of different technical substrates to understand how material properties affect their recrystallization behavior at the molecular level. For this purpose, four different technical substrates were chosen based on their polarity and crystallinity. On highly oriented pyrolytic graphite or HOPG (nonpolar, crystalline), LG recrystallization formed parallelogram-like-structures in the initial stage. On nonpolar, amorphous substrate like glassy carbon (GC) stalactite-like-structures were observed. Contrary to this, on polar substrates like mica (polar, crystalline) and glass (polar, amorphous), LG molecules were recrystallized as thin film. The morphological changes of LG at different time intervals were investigated and their mechanism of recrystallization on all the substrates is discussed in detail for the first time. Direct view of the recrystallization process at the molecular level on different technical substrates can be used as a model in understanding how these molecules as a constituent in skin cosmetic products behave, when applied to skins of varying physical and chemical barrier ultimately helping in better cosmetic development.

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“…reported LA oligomerization with glycerol using solid acidic catalysts such as Sb 2 O 3 , p‐toluenesulfonic acid, and 1‐(1‐propylsulfonic)‐3‐methylimidazolium chloride for the production of keto (K), glycerol‐ketal (KE), and glycerol‐ester (E). Freitas et al . also performed the ketalization between ethyl levulinate (Elevu) and ethylene glycol (EG) and 1,2‐dodecanediol using acid catalysts such as p ‐toluensolfonic acid, Amberlyst 70, zeolite H‐ZSM‐5, and niobium phosphate.…”

Section: Introductionmentioning

confidence: 99%

Esterification and ketalization of levulinic acid with desilicated zeolite β and pseudo‐homogeneous model for reaction kinetics

Umrigar

Chakraborty

Parikh

2019

Int J of Chemical Kinetics

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To maximize the production of esters (E), keto (K) and keto-ester (KE) by esterification and ketalization of levulinic acid (LA) has been reacted using diols such as 1,2-propane diol (PDOL),1,2-ethane diol (EDOL), and 1,2,3-propane triol or glycerol (TRIOL) with desilicated H . This work aims to assess the conversion and selectivity for the production of esters using conventional and microwave-irradiated (MWI) reactors. Catalysts characterizations were performed using NH 3 -temperature programme desorption, Brunauer, Emmett and Teller surface area (BET), Barrett, Joyner, and Halenda (BJH), scanning electron microscope, transmission electron microscope, and dynamic light scattering. Operating parameters such as reaction temperature (170-180 • C), reaction time (20-80 min), feed composition (LA:PDOL/EDOL/TRIOL, 1:8/10/12), and microwave energy (300-500 watt) have been systematically investigated. Note that 99-100% conversion was achieved with the product selectivity of E (40%), K (30%), and KE (30%) with1,2-EDOL; E (56%), K (2%), and KE (17%) with 1,2-PDOL; E (69%), K(0%), and KE (22%) with TRIOL using D-H as a solid catalyst in an MWI reactor. Reaction paths and kinetics were studied using pseudohomogeneous (PH) model. K E Y W O R D S esterification, ketalization, levulinic acid, microwave irradiation, pseudo-homogeneous (PH) model Int J Chem Kinet. 2019;51:299-308.How to cite this article: Umrigar V, Chakraborty M, Parikh P. Esterification and ketalization of levulinic acid with desilicated zeolite and pseudo-homogeneous model for reaction kinetics. Int J Chem Kinet. 2019;51:299-308.

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Heterogeneous catalysis for the ketalisation of ethyl levulinate with 1,2-dodecanediol: Opening the way to a new class of bio-degradable surfactants

Cited by 37 publications

References 28 publications

Cascade Strategy for the Tunable Catalytic Valorization of Levulinic Acid and γ-Valerolactone to 2-Methyltetrahydrofuran and Alcohols

Cascade Strategy for the Tunable Catalytic Valorization of Levulinic Acid and γ-Valerolactone to 2-Methyltetrahydrofuran and Alcohols

Substrate Influence on the Recrystallization of 1,2-dodecanediol: An Atomic Force Microscopy Study

Esterification and ketalization of levulinic acid with desilicated zeolite β and pseudo‐homogeneous model for reaction kinetics

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