Effect of structure and acidity of acid modified clay materials on synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol

Timofeeva, Maria N.; Panchenko, Valentina N.; Gil, Antonio; Закусин, С. В.; Krupskaya, V. V.; Волчо, К. П.; Vicente, M.A.

doi:10.1016/j.catcom.2015.07.005

Cited by 26 publications

(19 citation statements)

References 11 publications

(15 reference statements)

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“…A significant increase in the specific surface of the acid-modified clays promotes wide use of such material for removal of heavy metals, radionuclides and for oil refining [15][16][17][18][19]. The transformation of the structure and properties of bentonite under the influence of acids, mostly under sulfuric and hydrochloric acids, have been studied by different authors [20][21][22][23][24][25][26]. Using ultrasound and microwaves in addition to an acid treatment intensifies smectite mineral transformation [27].…”

Section: Introductionmentioning

confidence: 99%

Experimental Study of Montmorillonite Structure and Transformation of Its Properties under Treatment with Inorganic Acid Solutions

et al. 2017

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This paper discusses the mechanism of montmorillonite structural alteration and modification of bentonites' properties (based on samples from clay deposits Taganskoye, Kazakhstan and Mukhortala, Buriatia) under thermochemical treatment (treatment with inorganic acid solutions at different temperatures, concentrations and reaction times). Treatment conditions were chosen according to those accepted in chemical industry for obtaining acid modified clays as catalysts or sorbents. Also, more intense treatment was carried out to simulate possible influence at the liquid radioactive site repositories. A series of methods was used: XRD, FTIR, ICP-AES, TEM, nitrogen adsorption, and particle size analysis. It allowed revealing certain processes: transformation of montmorillonite structure which appears in the leaching of interlayer and octahedral cations and protonation of the interlayer and -OH groups at octahedral sheets. In turn, changes in the structure of the 2:1 layer of montmorillonite and its interlayer result in significant alterations in the properties: reduction of cation exchange capacity and an increase of specific surface area. Acid treatment also leads to a redistribution of particle sizes and changes the pore system. The results of the work showed that bentonite clays retain a significant portion of their adsorption properties even after a prolonged and intense thermochemical treatment (1 M HNO 3 , 60 • C, 108 h).

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Section: Introductionmentioning

confidence: 99%

Experimental Study of Montmorillonite Structure and Transformation of Its Properties under Treatment with Inorganic Acid Solutions

et al. 2017

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“…15 The acid-catalyzed Prins reaction of pulegols with various aldehydes containing electron-donating and electron-withdrawing substituents is often used for the synthesis of biologically active octahydro-2 H -chromen-4-ols. 16…”

Section: Resultsmentioning

confidence: 99%

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Slater

Lasonkar

Haider

et al. 2018

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Novel, functionalized octahydrochromene derivatives were synthesized in a single step the Prins reaction. Enantiomerically pure (+)-isopulegol was reacted with benzaldehyde to stereoselectively yield the corresponding octahydro-2-chromen-4-ol derivative containing five stereocenters. A total of 10 compounds were synthesized by altering the enantiomer of isopulegol and the substituted benzaldehyde, and the resulting enantiopure octahydrochromenes were screened against the cannabinoid receptor isoforms CB1 and CB2. Compounds containing an olefin at the C4 position [(+)-, (-)-, (-)-, (-)- and (-)-] of the octahydrochromene scaffold were found to exhibit reasonable displacement of [H] CP55,940 from the CB receptors, whereas the corresponding hydroxy analogs [(+)-, (+)-, (-)-, (-)- and (+)-] had very little or no effect.

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“…The occurrence of amorphous silica in kaolin clay samples can be explained by the presence of humps, peaks or large bands within the range of 15-25 • . Meanwhile, the peak observed in the X-ray diffractograms at the 2 θ range above than 66 • represents the quartz phase and 2 θ range less than 15 • reflects the presence of illite phase [27]. As seen in Figure 5, alternation occurs in the peaks of the catalysts after acid activation.…”

Section: Mineral Compositionmentioning

confidence: 94%

“…After acid activation, the morphological differences are apparent at high magnification. In the activated metakaolin micrograph showed the small particles and well-bonded aggregates rather than scattered particles [27]. There was minor particle dispersion in the activated K1 sample into the plate-like shaped particle.…”

Section: Morphology Of Raw Kaolin and Acid Activated Metakaolinmentioning

confidence: 95%

“…The clay samples were degassed by nitrogen flow for 24 h at 300 • C prior to the study to eliminate impurities and moisture on the surface of catalyst. The surface area was calculated from the adsorption isotherm while pore size and pore volume were determined from the desorption isotherm of BJH (Barret-Joyner-Halenda) [27]. All characterizations of prepared catalysts and product took place in the Central Analytical Laboratory, UTP.…”

Section: Brunauer-emmett-teller Isotherm (Bet)mentioning

confidence: 99%

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Activation of Nano Kaolin Clay for Bio-Glycerol Conversion to a Valuable Fuel Additive

et al. 2021

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High production of biodiesel results in a surplus of glycerol as a byproduct that leads to a drastic decline in the glycerol price as well as overall biodiesel production. Alternative methods must be introduced for the economical process for biodiesel production via utilization of crude glycerol into valuable chemicals or fuel additives. This study introduces an ecofriendly process of solketal synthesis from glycerol and acetone in the presence of a novel metakaolin clay catalyst, which is a useful additive in biodiesel or gasoline, in order to enhance the octane number and to control the emissions. Moreover, kaolin clay catalysts are low cost, abundantly available, eco-friendly and one of the more promising applications for solketal synthesis. In this study, raw kaolin clay was activated with an easy acid activation technique, modification in physicochemical and textural properties were determined by using X-ray diffraction (XRD), Fourier Transform Infra-Red (FTIR) spectroscopy, Brunauer–Emmett–Teller (BET) and Field Emission Scanning Electron Microscope. Among all acid-treated catalysts, metakaolin K3 have shown best catalytic properties, high surface area and pore size after acid activation with 3.0 mol/dm3 at 98 °C for 3 h. Acetalization of glycerol with acetone carried out in the presence of an environmentally friendly and inexpensive novel metakaolin K3 catalyst. The maximum yield of solketal obtained was 84% at a temperature of 50 °C, acetone/glycerol molar ratio 6/1 and for 90 min with novel metakaolin clay catalyst. Effect of various parameters (time, temperature, acetone/glycerol molar ratio, catalyst loading) on the solketal yield and glycerol conversion was discussed in detail. This approach offers an effective way to transform glycerol into solketal—a desirable green chemical with future industrial applications.

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Effect of structure and acidity of acid modified clay materials on synthesis of octahydro-2H-chromen-4-ol from vanillin and isopulegol

Cited by 26 publications

References 11 publications

Experimental Study of Montmorillonite Structure and Transformation of Its Properties under Treatment with Inorganic Acid Solutions

Experimental Study of Montmorillonite Structure and Transformation of Its Properties under Treatment with Inorganic Acid Solutions

One-step, stereoselective synthesis of octahydrochromanes via the Prins reaction and their cannabinoid activities

Activation of Nano Kaolin Clay for Bio-Glycerol Conversion to a Valuable Fuel Additive

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