Epoxidation of 1,5,9-cyclododecatriene with hydrogen peroxide under phase-transfer catalysis conditions: influence of selected parameters on the course of epoxidation

AbstractThis work presents the studies on the epoxidation of 1,5,9-cyclododecatriene (CDT) with hydrogen peroxide as the oxidizing agent, under conditions of the phase transfer catalysis (PTC), and with the following catalytic system: H2WO4/H3PO4/[CH3(CH2)7]3CH3N+HSO4− (compounds were mixed at the ratio of 2:1:1). The influence of the following parameters on the course of this process was investigated: catalyst content, molar ratio of H2O2:CDT, temperature and type of solvent. The highest yield of 1,2-epoxy-5,9-cyclododecadiene (ECDD) (54.9 mol%), at the conversion of CDT reached 72.3 mol%, was obtained at the temperature of 50 °C, for the catalyst content of 0.45 mol% (in relation to the introduced CDT), for the molar ratio of H2O2:CDT 1.5:1, with toluene as the solvent and after the reaction time of 30 min. Considering the he obtained results and numerous applications of ECDD, further research should be developed to provide a more efficient and environmentally friendly way of obtaining this compound. Graphic abstract

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Epoxidation of allyl-glycidyl ether with hydrogen peroxide over Ti-SBA-15 catalyst and in methanol medium

Polish Journal of Chemical Technology ◽

10.1515/pjct-2016-0064 ◽

2016 ◽

Vol 18 (4) ◽

pp. 9-14 ◽

Cited By ~ 2

Author(s):

Marika Walasek ◽

Agnieszka Wróblewska

Keyword(s):

Hydrogen Peroxide ◽

Reaction Time ◽

Glycidyl Ether ◽

Diglycidyl Ether ◽

Methanol Concentration ◽

Molar Ratio ◽

Oxidizing Agent ◽

Aqueous Hydrogen Peroxide ◽

Allyl Glycidyl Ether ◽

Catalyst Content

Abstract This work presents the studies on the epoxidation of allyl-glycidyl ether (AGE) over the Ti-SBA-15 catalyst. In these studies an aqueous hydrogen peroxide was used as an oxidizing agent and as a solvent methanol was applied. The studies on the influence the following parameters: temperature (20–80°C), molar ratio of AGE/H2O2 (1:1.5–5:1), methanol concentration (10–90 wt%), catalyst content (1–9 wt%) and reaction time (15–240 min.) were carried out and the most favourable values of these parameters were chosen (temperature 80°C, molar ratio of AGE/H2O2 = 5:1, methanol concentration 30 wt%, catalyst content 3 wt% and the reaction time 240 min.). At these conditions the functions describing the process reached the following values: the selectivity of diglycidyl ether (DGE) 9.2 mol%, the conversion of AGE 13.9 mol% and the efficiency of H2O2 conversion 89.9 mol%.

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The utilization of the mesoporous Ti-SBA-15 catalyst in the epoxidation of allyl alcohol to glycidol and diglycidyl ether in the water medium

Polish Journal of Chemical Technology ◽

10.1515/pjct-2015-0064 ◽

2015 ◽

Vol 17 (4) ◽

pp. 23-31 ◽

Cited By ~ 1

Author(s):

Agnieszka Wróblewska ◽

Edyta Makuch ◽

Małgorzata Dzięcioł ◽

Roman Jędrzejewski ◽

Paweł Kochmański ◽

...

Keyword(s):

Hydrogen Peroxide ◽

Reaction Time ◽

Allyl Alcohol ◽

Water Solution ◽

Reaction Medium ◽

Diglycidyl Ether ◽

Molar Ratio ◽

Water Medium ◽

Catalyst Content ◽

Allyl Alcohol Epoxidation

Abstract This work presents the studies on the optimization the process of allyl alcohol epoxidation over the Ti-SBA-15 catalyst. The optimization was carried out in an aqueous medium, wherein water was introduced into the reaction medium with an oxidizing agent (30 wt% aqueous solution of hydrogen peroxide) and it was formed in the reaction medium during the processes. The main investigated technological parameters were: the temperature, the molar ratio of allyl alcohol/hydrogen peroxide, the catalyst content and the reaction time. The main functions the process were: the selectivity of transformation to glycidol in relation to allyl alcohol consumed, the selectivity of transformation to diglycidyl ether in relation to allyl alcohol consumed, the conversion of allyl alcohol and the selectivity of transformation to organic compounds in relation to hydrogen peroxide consumed. The analysis of the layer drawings showed that in water solution it is best to conduct allyl alcohol epoxidation in direction of glycidol (selectivity of glycidol 54 mol%) at: the temperature of 10–17°C, the molar ratio of reactants 0.5–1.9, the catalyst content 2.9–4.0 wt%, the reaction time 2.7–3.0 h and in direction of diglycidyl ether (selectivity of diglycidyl ether 16 mol%) at: the temperature of 18–33°C, the molar ratio of reactants 0.9–1.65, the catalyst content 2.0–3.4 wt%, the reaction time 1.7–2.6 h. The presented method allows to obtain two very valuable intermediates for the organic industry.

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Environmentally friendly epoxidation of olefins under phase-transfer catalysis conditions with hydrogen peroxide

Journal of Catalysis ◽

10.1016/j.jcat.2007.05.001 ◽

2007 ◽

Vol 249 (2) ◽

pp. 338-348 ◽

Cited By ~ 36

Author(s):

Y MAHHA ◽

L SALLES ◽

J PIQUEMAL ◽

E BRIOT ◽

A ATLAMSANI ◽

...

Keyword(s):

Hydrogen Peroxide ◽

Phase Transfer Catalysis ◽

Phase Transfer ◽

Environmentally Friendly ◽

Epoxidation Of Olefins

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Synthesis of Biodiesel by Phase Transfer Catalysis

Applied Mechanics and Materials ◽

10.4028/www.scientific.net/amm.291-294.355 ◽

2013 ◽

Vol 291-294 ◽

pp. 355-358 ◽

Cited By ~ 1

Author(s):

Yan Qin Huang

Keyword(s):

Reaction Time ◽

Soybean Oil ◽

Reaction Temperature ◽

Phase Transfer Catalysis ◽

Phase Transfer ◽

Molar Ratio ◽

Mass Ratio ◽

Reaction Conditions ◽

Optimum Reaction

Biodiesel was synthesized starting soybean oil and methanol using K2CO3 and phase-transfer catalysis TBAB. It was studied that the yield of biodiesel can be changed with reaction factors such as the kind and the amount of phase-transfer catalysis, the amount of K2CO3, reaction time, molar ratio between methanol and soybean oil, reaction temperature. The results show that the reaction conditions are as following: mass ratio of TBAB to soybean oil weight 0.6%, mass ratio of K2CO3 to soybean oil weight 1.5%, molar ratio between methanol and soybean oil 6∶1, reaction time 20 min, reaction temperature 40 °C. The yield of biodiesel reached 95% under the optimum reaction conditions.

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Epoxidation of 1,5,9-Cyclododecatriene with Hydrogen Peroxide over Ti-MCM-41 Catalyst

Catalysts ◽

10.3390/catal11111402 ◽

2021 ◽

Vol 11 (11) ◽

pp. 1402

Author(s):

Agnieszka Wróblewska ◽

Marcin Kujbida ◽

Grzegorz Lewandowski ◽

Adrianna Kamińska ◽

Zvi C. Koren ◽

...

Keyword(s):

Hydrogen Peroxide ◽

Reaction Time ◽

Process Parameters ◽

Heterogeneous Catalysts ◽

Isopropyl Alcohol ◽

Solvent Composition ◽

Molar Ratio ◽

Catalyst Content ◽

Parameter Values ◽

Mcm 41

This work presents the results of our research on the epoxidation of 1,5,9-cyclododecatriene (CDT) with hydrogen peroxide over the Ti-MCM-41 catalyst. The influence of the following parameters on the course of the process was investigated: temperature, CDT:H2O2 molar ratio, solvent composition and its type, and catalyst content. The highest selectivity of CDT transformation to 1,2-epoxy-5,9-cyclododecadiene (ECDD)—approximately 100 mol%, the highest yet reported—was obtained at the CDT conversion of 13 mol% and with the following parameter values: a catalyst content of 5 wt%; a molar ratio of CDT:H2O2 = 2; isopropyl alcohol (i-PrOH) as the solvent, with a composition of 80 wt% in the reaction mixture; a temperature of 80 °C; and a reaction time of 240 min. The highest conversion of CDT (37 mol%) was obtained at the ECDD selectivity of 56 mol% and using the following process parameters: a catalyst content of 5 wt%; a molar ratio of CDT:H2O2 = 0.5; i-PrOH used as the solvent, with solvent composition of 80 wt%; a temperature of 80 °C; and a reaction time of 60 min. It should be emphasized that the CDT conversion obtained in the current study is higher (by 9 mol%) than that described in the literature on heterogeneous catalysts.

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

Polish Journal of Chemical Technology ◽

10.1515/pjct-2015-0072 ◽

2015 ◽

Vol 17 (4) ◽

pp. 82-87 ◽

Cited By ~ 8

Author(s):

Agnieszka Wróblewska ◽

Edyta Makuch ◽

Piotr Miądlicki

Keyword(s):

Hydrogen Peroxide ◽

Reaction Time ◽

Atmospheric Pressure ◽

Perillyl Alcohol ◽

Molar Ratio ◽

Titanium Silicate ◽

Butyl Hydroperoxide ◽

Tert Butyl Hydroperoxide ◽

Catalyst Content ◽

Mcm 41

Abstract 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°C (studies in the autoclave) and 80°C (studies in glass reactor), the molar ratio of limonene/oxidant (H2O2 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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A facile and effective method for preparation of 2.5-furandicarboxylic acid via hydrogen peroxide direct oxidation of 5-hydroxymethylfurfural

Polish Journal of Chemical Technology ◽

10.1515/pjct-2017-0002 ◽

2017 ◽

Vol 19 (1) ◽

pp. 11-16 ◽

Cited By ~ 8

Author(s):

Shuang Zhang ◽

Long Zhang

Keyword(s):

Hydrogen Peroxide ◽

Reaction Time ◽

Oxidation Mechanism ◽

Molar Ratio ◽

Alkaline Condition ◽

Optimal Parameters ◽

Direct Oxidation ◽

Reaction Parameters ◽

Alkaline Conditions ◽

Furandicarboxylic Acid

Abstract In this paper, 2,5-furandicarboxylic acid (FDCA) was efficiently prepared by the direct oxidation of 5-hydroxymethylfurfural (5-HMF) using hydrogen peroxide (H2O2) in alkaline conditions without any catalysts. The effects of reaction parameters on the process were systematically investigated and the optimal parameters were obtained as follows: molar ratio of 5-HMF:KOH:H2O2 was 1:4:8, reaction temperature and reaction time were determined as 70°C and 15 minutes, respectively. Under these conditions, the yield of FDCA was 55.6% and the purity of FDCA could reach 99%. Moreover, we have speculated the detailed oxidation mechanism of 5-HMF assisted by hydrogen peroxide in alkaline condition to synthesize FDCA.

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