Efficient production of 5-hydroxymethylfurfural through the dehydration of sugars with caprolactam hydrogen sulfate ([CPL]HSO4) ionic liquid catalyst in a water/proprylene glycol monomethyl ether mixed solvent

Huang, Pingzhen; Gu, Aijuan; Wang, Jinxing

doi:10.1007/s11164-014-1633-6

Cited by 5 publications

(5 citation statements)

References 29 publications

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“…Both bands at 582.46 and 505.31 cm -1 correspond to the amide group of lactam ring [22,23]. Moreover, according to a study reported by Huang et al [19], the characteristic peaks of caprolactam-based ionic liquids at 1441-1445 cm -1 and 2930-2941 cm -1 may relate to N-H and N-C-H, respectively.…”

Section: Ftir Analysis Of Caprolactammentioning

confidence: 76%

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Synthesis and Characterization of Caprolactam- based Ionic Liquids as Green Solvents

Naiyl

Kengara

Kiriamiti

et al. 2021

AJACR

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Aims: To synthesize and characterize six caprolactam-based ionic liquids (CPILs) by combination of caprolactam with different organic and inorganic Brønsted acids that can be utilized for lipid extraction from microalgae. Study design: Experimental design include quantitative and qualitative. Place and duration of study: The study was done at Department of Chemistry & Biochemistry, School of Sciences and Aerospace Studies, Moi University (Kenya) between November 2020 and May 2021. Methodology: Six CPILs were prepared through a simple neutralization reaction between Caprolactam and Brønsted acids such as Hydrochloric acid (HCl), Methane sulphonic acid (CH3SO3H), Trifluoromethanesulphonic acid (CF3SO3H), Acetic acid (CH3CO2H), Trifluoroacetic acid (CF3CO2H), and Sulfuric acid (H2SO4). The first three acids were used in the synthesis of CPILs for the first time. The chemical structures of the synthesized CPILs were characterized by Fourier transform infrared and Raman spectroscopy. The densities and viscosities were measured at 20 oC using the weight (pycnometer) and capillary viscometer (Oswald) methods, respectively. Results: All the CPILs were insoluble in hexane and had high miscibility with water and methanol. Fourier transform infrared and Raman spectra of the CPILs were compared with that of free Caprolactam. The characteristic absorption bands of the synthesized compounds showed a big shift in position and/or intensity (compared to caprolactam), indicating the formation of the CPILs. The results showed that both the density and viscosity increased with the molecular weight of the anion - except in Caprolactamium hydrogen sulphate (CPSA)- which could be due to the strong interactions between the cation and anion resulting from the dimerization between hydrogen sulphate anions. Conclusion: The hydrophilic nature of the CPILs indicated by high miscibility with polar solvents (water and methanol) indicates that they are suitable for the dissolution of cellulose of microalgae cell wall and thus could result in high lipid extraction efficiency. Further studies should therefore utilize the synthesized CPILs in lipid extraction from microalgae.

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Section: Ftir Analysis Of Caprolactammentioning

confidence: 76%

“…Six CPILs (Table 1 [19]. The synthesis of (CPHA) was used as an example in a typical experiment, and others were similar.…”

Section: Synthesis Of Ionic Liquidsmentioning

confidence: 99%

Synthesis and Characterization of Caprolactam- based Ionic Liquids as Green Solvents

Naiyl

Kengara

Kiriamiti

et al. 2021

AJACR

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“…Combination of ILs (neutral, with only Brønsted or Lewis acidity and dual Brønsted Lewis acidity) and organic solvents also showed promising conversion and selectivity in the dehydration reaction [129][130][131][132][133][134][135][136][137][138][139][140][141][142]. ILs can be recycled by distillation of organic solvents and extraction of products after reaction and be reused for several times without significant activity loss.…”

Section: Ilsmentioning

confidence: 99%

Acid-Catalyzed Dehydration of Fructose to 5-(Hydroxymethyl)furfural

Qiao¹,

Theyssen²,

Hou³

2015

Recyclable Catalysis

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Hydroxymethylfurfural (abbreviated as HMF), also 5-(hydroxymethyl)furfural, is an organic compound derived from dehydration of certain sugars. HMF is primarily considered as a starting material for liquid transportation fuels and polyester building block chemicals. The most convenient synthetic method of HMF is based on acidcatalyzed triple dehydration of fructose. Although there are many studies about fructose dehydration to 5-HMF since this field started to be investigated, it is necessary to provide a new review about fructose dehydration to 5-HMF. In the following, we will make a summary (in detail) of catalytic systems of fructose dehydration to HMF achieved by different acid catalysts, including mineral and organic acids, metal complexes, heteropoly acid-based materials, Ionic Liquids, ion-exchange resins, zeolites, functionalized carbonaceous materials and mesoporous silica materials. It has been demonstrated that nearly full conversion of fructose and 100% HMF selectivity could be obtained with some acidic catalytic systems up to now

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“…Recently, a one‐ pot hydrolysis/dehydration of polysaccharides into 2‐FA or 5‐HMF in the presence of ILs was reported . Caprolactam hydrogen sulfate [CPL][HSO 4 ], a relatively cheap and scarcely toxic IL, was proposed for the efficient production of 5‐HMF through sugar dehydration …”

Section: Introductionmentioning

confidence: 99%

Base‐Assisted Conversion of Protonated D‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models

et al. 2019

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A gas‐phase investigation of the D‐fructose dehydration reaction in the presence of base has been performed by the joint application of mass spectrometric techniques and theoretical calculations. Protonated addition products of D‐fructose and base were generated in the gas phase by electrospray ionization using several bases of different proton affinity. The intermediates, products and decomposition channels were investigated by ion trap mass spectrometry. Electronic structure calculations allowed the identification of the ionic intermediates and products of a selected system containing NH3, helping to rationalize the observed reaction pathways. The obtained results show that the final product, the protonated 5‐hydroxymethyl‐2‐furaldheyde [5‐HMF]H+, is better formed using selected bases and only if these remain clustered until the end of the dehydration process.

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Efficient production of 5-hydroxymethylfurfural through the dehydration of sugars with caprolactam hydrogen sulfate ([CPL]HSO4) ionic liquid catalyst in a water/proprylene glycol monomethyl ether mixed solvent

Cited by 5 publications

References 29 publications

Synthesis and Characterization of Caprolactam- based Ionic Liquids as Green Solvents

Synthesis and Characterization of Caprolactam- based Ionic Liquids as Green Solvents

Acid-Catalyzed Dehydration of Fructose to 5-(Hydroxymethyl)furfural

Base‐Assisted Conversion of Protonated D‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models

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