Oxidation of cyclopentene catalyzed by phosphotungstic quaternary ammonium salt catalysts

Xue, Jinjuan; Wang, Aili; Yin, Hengbo; Wang, Jingbo; Zhang, Dongzhi; Chen, Weiguang; Long, Yu; Jiang, Tingshun

doi:10.1016/j.jiec.2009.09.068

Cited by 22 publications

(8 citation statements)

References 24 publications

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“…Figure 1 shows the FTIR spectra of hexadecylpyridinium chloride (a) and the as-prepared phase-transfer catalyst (p-C 5 H 5 N[CH 2 ] 15 CH 3 ) 3 (PW 4 O 16 ) (b). Absorption peaks at 1079, 954, 885, and 802 cm À1 were observed in the FTIR spectra of sample (b), and these peaks correspond to the four characteristic skeletal vibrations of the Keggin oxoanions [22,42]. The peaks at 1079 and 954 cm À1 were due to the stretching vibrations of the P-O and W --O bonds, respectively, and the peaks at 885 and 802 cm À1 were due to n (W-O b -W) (corner-sharing) and n (W-Oc-W) (edge-sharing), respectively.…”

Section: Methodsmentioning

confidence: 98%

“…In contrast, phosphotungstic quaternary ammonium, which is a heterogeneous phase‐transfer catalyst (PTC), exhibits excellent catalytic activity and can be easily separated for practical applications. Therefore, this catalyst is one of the most suitable catalysts for use in the epoxidation reaction . The phase‐transfer catalyst is initially insoluble in the reaction medium.…”

Section: Introductionmentioning

confidence: 99%

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Optimization of epoxidation of ricinoleic acid methyl ester by hydrogen peroxide and phase‐transfer catalyst using response surface methodology

Zhao

Chen

Liu

et al. 2017

Euro J Lipid Sci & Tech

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The epoxidation of ricinoleic acid methyl ester (RAME) has been investigated using an environmentally friendly oxidant (i.e., hydrogen peroxide) and a phase‐transfer catalyst ([π‐C5H5N(CH2)15CH3]3[PW4O16]) in dichloroethane. The response surface methodology (RSM), based on the Box–Behnken design was used to assess individual and interactive effects of the process variables and to optimize the epoxidation reaction condition. The coefficient of determination (R2 = 0.9544) obtained from analysis of the variance confirmed the suitability of the fitted model. The RSM analysis results indicated that the molar ratio of H2O2 to CC bonds and the reaction temperature are the most significant (P < 0.01) factors affecting the conversion of RAME epoxide. In addition, the interaction between the H2O2/CC molar ratio and the catalyst dosage also has significant effect (P < 0.05) on the conversion of RAME epoxide. The optimum reaction conditions for the epoxidation of RAME were H2O2: CC molar ratio of 1.93:1, catalyst dosage of 3.11 wt% (substrate:catalyst molar ratio = 207), reaction temperature of 52°C, and reaction time of 75 min, under which a conversion of 94.52% could be achieved. The epoxidation of RAME by hydrogen peroxide and the (π‐C5H5N[CH2]15CH3)3(PW4O16) phase‐transfer catalyst followed pseudo‐first order kinetics with an activation energy (Ea) of approximately 21.6 kJ/mol. The reaction process is a mass‐transfer control process. Practical applications: RSM was found to be a useful technique for optimizing epoxidation of RAME. The high conversion of the epoxidation of RAME indicates that (π‐C5H5N[CH2]15CH3)3(PW4O16) is a very efficient phase‐transfer catalyst for the epoxidation of RAME under the mild conditions mentioned above. The epoxidized RAME have the potential to be used as biolubricants, surfactants, biobased polymers, and surface‐active compounds for high‐value cosmetic. The epoxidized ricinoleic acid methyl ester (RAME) have great potential to be used as biolubricants, biobased polymers, and surface‐active compounds in a variety of industries. RAME is epoxidized using an environmentally friendly oxidant (hydrogen peroxide) and a phase‐transfer catalyst ([p‐C5H5N(CH2)15CH3]3[PW4O16]) in dichloroethane. The high conversion (94.52%) is achieved by using response surface methodology to optimize the epoxidation reaction variables.

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Section: Methodsmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Optimization of epoxidation of ricinoleic acid methyl ester by hydrogen peroxide and phase‐transfer catalyst using response surface methodology

Zhao

Chen

Liu

et al. 2017

Euro J Lipid Sci & Tech

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“…Cyclopentene (CPE) can be oxidized under different conditions to obtain products such as glutaraldehyde, cis and trans 1,2-cyclopentenediol, cyclopentene oxide (CPO) (Xue et al, 2010), cyclopentanone, 1-cyclopenten-1-ol, 2-cyclopenten-1-ol (Zhang and Du, 2013), penta-1,4-dien-3-ol, and carbon dioxide and water under total oxidation conditions (Kluson et al, 2005). The oxidation products of CPE may be applied not only in the fine chemicals industry but also as bactericides, tanning agents, and in protein crosslinking (Yuan and Chen, 2011).…”

Section: Introductionmentioning

confidence: 99%

Epoxidation of cyclopentene by a low cost and environmentally friendly bicarbonate/peroxide/manganese system

Hincapie

Llano

Garcés

et al. 2017

Adsorption Science & Technology

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The system hydrogen peroxide/sodium bicarbonate/manganese sulfate was used for the first time to epoxidize cyclopentene. Effects of parameters such as type and amount of solvent, ratio of hydrogen peroxide and manganese sulfate to cyclopentene, presence of additives, and reaction time and temperature on the selectivity to cyclopentene oxide were evaluated. Gas chromatography was used to quantify residual cyclopentene and produced cyclopentene oxide using the internal standard method. Type and amount of solvent, addition method, and temperature were important factors to increase the selectivity to cyclopentene oxide. Unlike previous reports on epoxidation of different substrates, additives like sodium acetate and salicylic acid did not improve the selectivity to cyclopentene oxide. One time, single-step addition of hydrogen peroxide/sodium bicarbonate to the solution of cyclopentene/solvent/manganese

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“…Epoxidation of olefins has attracted much attention in both industry and academy because epoxides are intermediates for useful organic syntheses [4][5][6][7][8][9]. The metalloporphyrins have been served as versatile catalysts for oxidation reactions [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…Understanding these systems leads to the development of more active and selective catalysts for hydrocarbon oxidation. Structure of metallophthalocyanines (MPc) are similar to that of metalloporphyrins; however, they are generally more stable, available, and inexpensive [2,3].Epoxidation of olefins has attracted much attention in both industry and academy because epoxides are intermediates for useful organic syntheses [4][5][6][7][8][9]. The metalloporphyrins have been served as versatile catalysts for oxidation reactions [10][11][12].…”

mentioning

confidence: 99%

cis-Cyclooctene epoxidation catalyzed by bulk metallophthalocyanines, metallohexadecafluorophthalocyanines and hollow silica-supported metallohexadecafluorophthalocyanine

Vu¹,

Phung²

2016

Journal of Industrial and Engineering Chemistry

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Oxidation of cyclopentene catalyzed by phosphotungstic quaternary ammonium salt catalysts

Cited by 22 publications

References 24 publications

Optimization of epoxidation of ricinoleic acid methyl ester by hydrogen peroxide and phase‐transfer catalyst using response surface methodology

Optimization of epoxidation of ricinoleic acid methyl ester by hydrogen peroxide and phase‐transfer catalyst using response surface methodology

Epoxidation of cyclopentene by a low cost and environmentally friendly bicarbonate/peroxide/manganese system

cis-Cyclooctene epoxidation catalyzed by bulk metallophthalocyanines, metallohexadecafluorophthalocyanines and hollow silica-supported metallohexadecafluorophthalocyanine

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