Limonene oxidation by molecular oxygen under solvent-free conditions: the influence of peroxides and catalysts on the reaction rate

Pena, Andrés; Veiga, Santiago; Sapelli, Mariángeles; Martínez, Natalia; Márquez, Victoria; Dellacassa, Eduardo; Bussi, Juan

doi:10.1007/s11144-012-0485-6

Cited by 18 publications

(21 citation statements)

References 29 publications

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“…The studies on the oxidation of limonene were carried out with hydrogen peroxide and TBHP as oxidants and with help of two methods: at the autogenic pressure and at the atmospheric pressure. At the autogenic pressure the oxidation was performed in the autoclave of Berghof company equipped with the TEFLON insert with the capacity of 150 cm 3 and at the pressure of 10 bars. At the atmospheric pressure the studies were performed in the glass reactor with the capacity of 100 cm 3 equipped with the refl ux condenser, the thermometer and magnetic stirrer.…”

Section: 27mentioning

confidence: 99%

The oxidation of limonene at raised pressure and over the various titanium-silicate catalysts

Wróblewska

Makuch

Miądlicki

2015

Polish Journal of Chemical Technology

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This work presents the studies on the oxidation of limonene with hydrogen peroxide and tert-butyl hydroperoxide (TBHP) in the presence of : TS-2, Ti-Beta, Ti-MCM-41 and Ti-MWW catalysts, at the autogenic pressure and atmospheric pressure. The examination were performed at the following conditions: the temperature of 140 o C (studies in the autoclave) and 80 o C (studies in glass reactor), the molar ratio of limonene/oxidant (H 2 O 2 or WNTB) = 1:1, the methanol concentration 80 wt%, the catalyst content 3 wt%, the reaction time 3 h and the intensity of stirring 500 rpm. The analysis of the results showed that in process not only 1,2-epoxylimonene was formed but also: 1,2-epoxylimonene diol, carveol, carvone and perillyl alcohol but for 1,2-epoxylimonene obtaining the better method was the method at the autogenic pressure and in the presence of TBHP.

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Section: 27mentioning

confidence: 99%

The oxidation of limonene at raised pressure and over the various titanium-silicate catalysts

Wróblewska

Makuch

Miądlicki

2015

Polish Journal of Chemical Technology

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“…[12][13][14][15][16][17] Epoxidation of alkenes with hydrogen peroxide (H2O2), has been extensively studied. [18][19][20][21][22][23][24][25][26][27][28][29] The main benefit of using H2O2 as an oxidant is its environment-friendly nature; it only produces water (H2O) as a by-product. However, the epoxidation of limonene with H2O2 remains a challenging area because in the presence of H2O, the epoxide is prone to hydrolytic ring-opening reaction.…”

Section: Introductionmentioning

confidence: 99%

Development of a selective, solvent-free epoxidation of limonene using hydrogen peroxide and a tungsten-based catalyst

et al. 2018

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The development of a limonene epoxidation process using environment-friendly H2O2, with high H2O2 conversion (~95%) and selectivity to the epoxide (100%), is reported in this paper. Parametric studies of temperature, oxidant, solvent, acid concentration and sodium sulphate amounts were performed with the focus on establishing a rapid and highly selective process. Approximately 95% conversion of H2O2 at 100% selectivity to limonene-1,2-epoxide was achieved in 15 minutes with a single-step addition of oxidant.The operating conditions included a 323 K temperature in a solvent-free environment, with a limonene/H2O2/catalyst molar ratio of 4:1:0.005, using a tungsten-based polyoxometalates. To prevent the hydrolysis of the epoxide, the reaction mixture was saturated with sodium sulphate. An acid concentration of lower than 0.04 M was used and found to have significant effect on the selectivity. Kinetic studies were performed to allow modelling of the reaction scheme. The activation energy was determined to be ~36 kJ mol -1 .

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“…Limonene is widely used in food and cosmetic industries, and also in production of refrigerant fluids, paints, agrochemicals and cleaning agents. [8][9][10][11][12][13] R-(+)-limonene is the major component (about 97%) of the orange oil obtained from orange and lemon peels (biomass) which are the waste product of the citrus fruit industry. The main methods of obtaining orange oil from the orange peels are: cold pressing and distillation.…”

Section: Introductionmentioning

confidence: 99%

Fragrant starch-based films with limonene

Antosik¹,

Wilpiszewska²,

Wróblewska³

et al. 2017

10.5267/j.ccl

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Novel fragrant starch-based films with limonene were successfully prepared. Biodegradable materials of natural origin were used and the process was relatively simple and inexpensive. The effect of limonene on physicochemical properties of starch-based films (moisture absorption, solubility in water, wettability, mechanical properties) were compared to glycerol plasticized system. Taking into consideration that the obtained materials could also exhibit bactericidal and fungicidal properties, the studies with Escherichia coli, Candida albicans and Aspergillus niger were performed. Such a material could potentially find application in food packaging (e.g. masking unpleasant odors, hydrophilic starch film would prevent food drying), or in agriculture (e.g. for seed encapsulated tapes).

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Limonene oxidation by molecular oxygen under solvent-free conditions: the influence of peroxides and catalysts on the reaction rate

Cited by 18 publications

References 29 publications

The oxidation of limonene at raised pressure and over the various titanium-silicate catalysts

The oxidation of limonene at raised pressure and over the various titanium-silicate catalysts

Development of a selective, solvent-free epoxidation of limonene using hydrogen peroxide and a tungsten-based catalyst

Fragrant starch-based films with limonene

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