Ionic liquid-mediated deoxydehydration reactions: Green synthetic process for bio-based adipic acid

Shin, Nara; Kwon, Sohyun; Moon, Sojeong; Hong, Chae Hwan; Kim, Young Gyu

doi:10.1016/j.tet.2017.06.053

Cited by 29 publications

(20 citation statements)

References 73 publications

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“…Simultaneously, one of the protons at C4 and C5 carbons in the imidazole ring is shielded and shifted from 7.58 to 7.24 ppm (Figure 5A, Table 1). Shin et al [51] also noted that only one of the H4, H5 protons shifts as a result of the change from ethyl to butyl substituent [51]. The aforementioned changes prove the successful transesterification reaction between the RIL and CAP.…”

Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Cellulose Acetate Propionate Films Functionalized with Reactive Ionic Liquids

et al. 2019

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1-(1,3-diethoxy-1,3-dioxopropan-2-ylo)-3-methylimidazolium bromide (RIL1_Br), 1-(2-etoxy-2-oxoethyl)-3-methylimidazolium bromide (RIL2_Br), 1-(2-etoxy-2-oxoethyl)-3-methylimidazolium tetrafluoroborate (RIL3_BF4) ionic liquids were synthesized. Subsequently, the dense cellulose acetate propionate (CAP)-based materials containing from 9 to 28.6 wt % of these reactive ionic liquids were elaborated. Reactive ionic liquids (RILs) were immobilized in CAP as a result of the transesterification reaction. The yield of this reaction was over 90% with respect to the used RIL. The physicochemical properties of resultant films were studied using nuclear magnetic resonance (NMR), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), atomic force microscopy (AFM), and thermogravimetric analysis (TGA). The RIL incorporation influenced the morphology of films by increasing their surface roughness with the rise of RIL content. The thermal stability of CAP-based membranes was dependent on the nature of the ionic liquid. Nevertheless, it was proven that CAP films containing RILs were stable up to 120–150 °C. Transport properties were characterized by water permeation tests. It was found that the type and the amount of the ionic liquid in the CAP matrix substantially influenced the transport properties of the prepared hybrid materials.

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Section: Resultsmentioning

confidence: 99%

Preparation and Characterization of Cellulose Acetate Propionate Films Functionalized with Reactive Ionic Liquids

et al. 2019

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“…Because hexaric acids have four stereochemically diverse secondary hydroxy groups and two carboxyl groups, they have been studied since the 1950s as platform chemicals for producing chelating agents and corrosion inhibitors [10,11,12,13,14,15,16,17,18,19,20,21], precursors for polyamides [22,23,24,25,26,27,28,29,30,31,32,33,34,35,36], polyesters [37,38,39,40,41], polyanhydrides [42], polycations [43], coordination polymers including metal–organic frameworks [44,45,46,47,48], pendant polymers [49], macromolecules [50,51], cross-linkers in hydrogels [52], medicines [8,9,10,11,49,51,53], and other compounds including platform chemicals, like adipic acid and furan dicarboxylic acid [54,55,56,57,58,59,60,61,62].…”

Section: Applications Of Hexaric Acidsmentioning

confidence: 99%

“…Hexaric acids have also been studied for use as the starting materials for other platform chemicals [54,55,56,57,58,59,60,61,62], including adipic acid [59,60,61,62], furan dicarboxylic acid (an alternative to terephthalic acid) [57], and pyrrole [55].…”

Section: Applications Of Hexaric Acidsmentioning

confidence: 99%

Production of Hexaric Acids from Biomass

Sakuta

Nakamura

2019

IJMS

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Sugar acids obtained by aldohexose oxidation of both the terminal aldehyde group and the hydroxy group at the other end to carboxyl groups are called hexaric acids (i.e., six-carbon aldaric acids). Because hexaric acids have four secondary hydroxy groups that are stereochemically diverse and two carboxyl groups, various applications of these acids have been studied. Conventionally, hexaric acids have been produced mainly by nitric acid oxidation of aldohexose, but full-scale commercialization has not been realized; there are many problems regarding yield, safety, environmental burden, etc. In recent years, therefore, improvements in hexaric acid production by nitric acid oxidation have been made, while new production methods, including biocatalytic methods, are actively being studied. In this paper, we summarize these production methods in addition to research on the application of hexaric acids.

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“…In another application ILs have been used as a reaction medium for the dehydration of biomass derived galactaric acid to adipic acid. In this instance, use of an IL enabled the separation of rhenium catalyst used in the hydrogenation step from the products by simple decantation . The bio‐oil extraction from Jatropha curcas is another area where ILs have been tested, and these oils can be upgraded to fuels and numerous chemicals .…”

Section: Miscellaneous Applications Of Ionic Liquids In Biomass Procementioning

confidence: 99%

Ionic Liquids in Biomass Processing

Amarasekara

2018

Israel Journal of Chemistry

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The ionic liquids have emerged as new solvents and catalysts for processing biomass to value added chemicals and fuels. This review will present the recent developments in applications of ionic liquids in lignocellulosic biomass pretreatments, depolymerization, biodiesel synthesis, dehydration of carbohydrates to renewable feedstock chemicals as well as further transformations of biomass derived feedstocks such as furfural, 5‐hydroxymethylfurfural and levulinic acid to value added chemicals. In addition, the recycling of ionic liquids used in biomass processing is also discussed in the review.

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Ionic liquid-mediated deoxydehydration reactions: Green synthetic process for bio-based adipic acid

Cited by 29 publications

References 73 publications

Preparation and Characterization of Cellulose Acetate Propionate Films Functionalized with Reactive Ionic Liquids

Preparation and Characterization of Cellulose Acetate Propionate Films Functionalized with Reactive Ionic Liquids

Production of Hexaric Acids from Biomass

Ionic Liquids in Biomass Processing

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