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Optimization of epoxidation of ricinoleic acid methyl ester by hydrogen peroxide and phase‐transfer catalyst using response surface methodology
Author(s) -
Zhao Ke,
Chen Bang,
Li Cong,
Xia Chaoshuang,
Li Xingfu,
Li Kebin,
Shen Yehua
Publication year - 2017
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201700185
Subject(s) - hydrogen peroxide , catalysis , chemistry , epoxide , response surface methodology , substrate (aquarium) , nuclear chemistry , organic chemistry , chromatography , oceanography , geology
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‐C 5 H 5 N(CH 2 ) 15 CH 3 ] 3 [PW 4 O 16 ]) 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 ( R 2 = 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 H 2 O 2 to CC 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 H 2 O 2 /CC 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 H 2 O 2 : CC 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‐C 5 H 5 N[CH 2 ] 15 CH 3 ) 3 (PW 4 O 16 ) phase‐transfer catalyst followed pseudo‐first order kinetics with an activation energy ( E a ) 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‐C 5 H 5 N[CH 2 ] 15 CH 3 ) 3 (PW 4 O 16 ) 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‐C 5 H 5 N(CH 2 ) 15 CH 3 ] 3 [PW 4 O 16 ]) in dichloroethane. The high conversion (94.52%) is achieved by using response surface methodology to optimize the epoxidation reaction variables.