Nguyen Thi Thuy, Nguyen Thanh Liem, Vu Minh Duc

Main Article Content

Abstract

Abstract: The study investigated the selectivity of tungstate-based catalyst in the epoxidation of rubber seed oil and modified rubber seed oil by two methods: The titration method was performed according to the ASTM standard and the H-NMR method was based on the peaks of the three different standard groups. The catalyst selectivity of the epoxidation reaction of modified rubber seed oil was much higher than that of non-modified rubber seed oil for both methods. The average catalyst selectivity obtained by using H-NMR method in the modified rubber seed oil epoxidation reaction was equal to that of the titrimetric method, while the selectivity of the rubber seed oil epoxidation reaction was 11% lower than that of the titrimetric method. For both types of oil, the difference between the catalytic selectivity obtained by using the titration method and by using protons in group α-CH2-(C=O)-O- as the standard peak, was the smallest and when the proton in group -CH3 was used as the standard peak, the difference in selectivity was the biggest.


Keywords: Selectivity, tungstate-based catalyst, H-NMR.


References
[1] Vaibhav V. Goud, Narayan C. Pradhan and Anand V. Patwardhan, Epoxidation of Karanja (Pongamia glabra) Oil by H2O2, Journal of the American Oil Chemists’ Society 83(7) 2006, 635-640
[2] Harshal Patil, Jyotsna Waghmare, Catalyst for epoxidation of oils: a review, Discovery 3(7) (2013) 10-14
[3] Tayde Saurabh, Patnaik M., Bhagt SL., Renge V.C, Epoxidation of vegetable oils: a review, International Journal of Advanced Engineering Technology, II(IV) (2011) 491-501
[4] Lathi P and Mattiasson, B., Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil, Applied Catalyst B: Environmental 69 (2007) 207-219
[5] Petrovic, ZS Zlatanic, A Lava, CC and Sinadinovic-Fiser, S., Epoxidation of soybean oil in toluene with peroxy acetic and peroxy formic acids-kinetics and side reactions, European Jouranl of Lipid Science and Technology, 104(5) (2002) 293-299
[6] Tornvall, U., C. Orellana-Coca. R. Hatti-kaul and D Adlercreutz, Stability of immobilized Candida antarctica lipase B during chemo-enzymatic epoxidation of fatty acids, Enzyme Microbial Technology 40 (2007) 447-451
[7] Bashar Mudhaffar Abdullah and Jumat Salimon, Epoxidation of Vegetable Oil and Fatty Acids: Catalysts, Method and Advantages, Jouranl of Applied Science 10(5) (2010) 1545-1553
[8] A. Campanella, M.A. Baltanas, M.C. Capel-Sanchew, J.M. Campos-Martin and J.L.G. Fierro, Soybean oil epoxidation with hydrogen peroxide using an amorphous Ti/SiO2 catalyst, Green Chemistry 6 (2004) 330-334
[9] Mohamed Tahar Benaniba, Naima Belhaneche-Bensemra, Georges Gelbard, Kinetic of Tungsten-catalyzed Sunflower Oil Epoxidation Studied by 1H NMR, European Journal of Lipid Science and Technology, 109 (2007) 1186 -1193
[10] Do Huy Thanh, Tran Cong Khanh, Phan Van Ninh, Epoxidation of rubber seed oil by hydroperoxide with ammonium molybdenum catalyst, Vietnam Journal of Chemistry, 1 (2001) 99-106
[11] Nguyen Thi Thuy, Vu Minh Duc, Phan Ngoc Quy, Nguyen Thanh Liem, Metal-based catalyst for epoxidation of soybean oil, Vietnam Journal of Chemistry, 53(4) (2015) 515-519
[12] Nguyen Thi Thuy, Vu Minh Duc, Phan Ngoc Quy, Effect of components in tungsten-based catalyst system on the epoxidation reaction of soybean oil, VUN journal of Science: Natural Sciences and Technology, 33(1), (2017) 81-87
[13] Nguyen Thi Thuy, Vu Minh Duc, Nguyen Thanh Liem, Thermodynamics study of epoxidation of soy bean oil by using tungstate-based catalyst, VUN journal of Science: Natural Sciences and Technology, 32(1), (2016) 86-93
[14] Nguyen Thi Thuy, Vu Minh Duc, Epoxidation of sunflower oil, Vietnam Journal of Chemistry, 54(1), (2016) 38-42
[15] Nguyen Thi Thuy, Vu Minh Duc, Michiel Vrijsen, Nguyen Thanh Liem, Investigation of the impact of the reaction conditions on the epoxidation of refined sunflower oil using a sodium tungstate dihydrate catalyst, Vietnam Journal of Chemistry, 7th National Conference on Chemistry 53(6e), (2015) 29-33
[16] Nguyen Thi Thuy, Vu Minh Duc, Nguyen Thanh Liem, Investigation on acid value reduction of Vietnam crude rubber seed oil for a green material in organic synthesis, Journal of Science & Technology Technical Universities, 114 (2016) 108-112
[17] P. Saithai, J. Lecomete, E. Dubreucp, V. Tanrattanakul, Effect of Different Epoxidation Methods of Soybean Oil on the Characteristics of Acrylated Epoxidized Soybean Oil-co-poly(methyl methacrylate) Copolymer, eXPRESS Polymer Letters, 7(11), (2013) 910-924
[18] Alejandrina Campanella, John J. La Scala, R. P. Wool, Fatty Acid-Based Comonomers as Styrene Replacements in Soybean and Castor Oil-Based Thermosetting Polymers, Journal of Applied Polymer Science, 119, (2011) 1000-1010
[19] Nguyen Thi Thuy, Vu Minh Duc, Nguyen Thanh Liem, Investigation of the changes in properties and chemical compositions of Vietnam crude rubber seed oil during deacidification treatment, Journal of Science & Technology Technical Universities, 115 (2016) 128-132.

Keywords: selectivity, tungstate-based catalyst, H-NMR

References

References

[1] Vaibhav V. Goud, Narayan C. Pradhan and Anand V. Patwardhan, Epoxidation of Karanja (Pongamia glabra) Oil by H2O2, Journal of the American Oil Chemists’ Society 83(7) 2006, 635-640
[2] Harshal Patil, Jyotsna Waghmare, Catalyst for epoxidation of oils: a review, Discovery 3(7) (2013) 10-14
[3] Tayde Saurabh, Patnaik M., Bhagt SL., Renge V.C, Epoxidation of vegetable oils: a review, International Journal of Advanced Engineering Technology, II(IV) (2011) 491-501
[4] Lathi P and Mattiasson, B., Green approach for the preparation of biodegradable lubricant base stock from epoxidized vegetable oil, Applied Catalyst B: Environmental 69 (2007) 207-219
[5] Petrovic, ZS Zlatanic, A Lava, CC and Sinadinovic-Fiser, S., Epoxidation of soybean oil in toluene with peroxy acetic and peroxy formic acids-kinetics and side reactions, European Jouranl of Lipid Science and Technology, 104(5) (2002) 293-299
[6] Tornvall, U., C. Orellana-Coca. R. Hatti-kaul and D Adlercreutz, Stability of immobilized Candida antarctica lipase B during chemo-enzymatic epoxidation of fatty acids, Enzyme Microbial Technology 40 (2007) 447-451
[7] Bashar Mudhaffar Abdullah and Jumat Salimon, Epoxidation of Vegetable Oil and Fatty Acids: Catalysts, Method and Advantages, Jouranl of Applied Science 10(5) (2010) 1545-1553
[8] A. Campanella, M.A. Baltanas, M.C. Capel-Sanchew, J.M. Campos-Martin and J.L.G. Fierro, Soybean oil epoxidation with hydrogen peroxide using an amorphous Ti/SiO2 catalyst, Green Chemistry 6 (2004) 330-334
[9] Mohamed Tahar Benaniba, Naima Belhaneche-Bensemra, Georges Gelbard, Kinetic of Tungsten-catalyzed Sunflower Oil Epoxidation Studied by 1H NMR, European Journal of Lipid Science and Technology, 109 (2007) 1186 -1193
[10] Do Huy Thanh, Tran Cong Khanh, Phan Van Ninh, Epoxidation of rubber seed oil by hydroperoxide with ammonium molybdenum catalyst, Vietnam Journal of Chemistry, 1 (2001) 99-106
[11] Nguyen Thi Thuy, Vu Minh Duc, Phan Ngoc Quy, Nguyen Thanh Liem, Metal-based catalyst for epoxidation of soybean oil, Vietnam Journal of Chemistry, 53(4) (2015) 515-519
[12] Nguyen Thi Thuy, Vu Minh Duc, Phan Ngoc Quy, Effect of components in tungsten-based catalyst system on the epoxidation reaction of soybean oil, VUN journal of Science: Natural Sciences and Technology, 33(1), (2017) 81-87
[13] Nguyen Thi Thuy, Vu Minh Duc, Nguyen Thanh Liem, Thermodynamics study of epoxidation of soy bean oil by using tungstate-based catalyst, VUN journal of Science: Natural Sciences and Technology, 32(1), (2016) 86-93
[14] Nguyen Thi Thuy, Vu Minh Duc, Epoxidation of sunflower oil, Vietnam Journal of Chemistry, 54(1), (2016) 38-42
[15] Nguyen Thi Thuy, Vu Minh Duc, Michiel Vrijsen, Nguyen Thanh Liem, Investigation of the impact of the reaction conditions on the epoxidation of refined sunflower oil using a sodium tungstate dihydrate catalyst, Vietnam Journal of Chemistry, 7th National Conference on Chemistry 53(6e), (2015) 29-33
[16] Nguyen Thi Thuy, Vu Minh Duc, Nguyen Thanh Liem, Investigation on acid value reduction of Vietnam crude rubber seed oil for a green material in organic synthesis, Journal of Science & Technology Technical Universities, 114 (2016) 108-112
[17] P. Saithai, J. Lecomete, E. Dubreucp, V. Tanrattanakul, Effect of Different Epoxidation Methods of Soybean Oil on the Characteristics of Acrylated Epoxidized Soybean Oil-co-poly(methyl methacrylate) Copolymer, eXPRESS Polymer Letters, 7(11), (2013) 910-924
[18] Alejandrina Campanella, John J. La Scala, R. P. Wool, Fatty Acid-Based Comonomers as Styrene Replacements in Soybean and Castor Oil-Based Thermosetting Polymers, Journal of Applied Polymer Science, 119, (2011) 1000-1010
[19] Nguyen Thi Thuy, Vu Minh Duc, Nguyen Thanh Liem, Investigation of the changes in properties and chemical compositions of Vietnam crude rubber seed oil during deacidification treatment, Journal of Science & Technology Technical Universities, 115 (2016) 128-132