Journal of Industrial and Engineering Chemistry, Vol.91, 191-200, November, 2020
Acid-free epoxidation of soybean oil with hydrogen peroxide to epoxidized soybean oil over titanium silicalite-1 zeolite supported cadmium catalysts
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Titanium silicalite-1 (TS-1) zeolite was successfully synthesized by hydrothermal method in the presence of the tetrapropylammonium hydroxide (TPAOH) template, and a series of TS-1 supported cadmium with different Cd loading (xCd/TS-1) catalysts were carefully prepared to produce epoxidized soybean oil (ESO) through the acid-free catalytic epoxidation of soybean oil (SO) with H2O2. These catalysts were fully characterized using various modern techniques and further evaluated systematically in this epoxidation reaction to understand the relationship between catalytic activity and structure of active components. The results show that the highly dispersed Cd species are introduced on the TS-1 support without affecting the coordination environment of tetrahedral Ti (framework Ti). Furthermore, the Cd species are coordinated with tetrahedral Ti species via O atom resulting in the weakness of the Ti-O bonds and facile attack of the Ti-O bonds by alcohol and H2O2, which can easily form the five-membered intermediate and promote the SO epoxidation process. Furthermore, the deactivation and regeneration behaviors of 2%Cd/TS-1 catalyst in SO epoxidation were also investigated, which reveal that the catalyst deactivation of coke deposition is due to the strong adsorption of the catalysts and SO molecules. But the spent 2%Cd/TS-1 can be completely regenerated by calcination method.
- Park MS, Choi IW, Lee SJ, Hong SJ, Kim AY, Shin JH, Kang HC, Kim YW, J. Ind. Eng. Chem., 88, 148 (2020)
- Zheng T, Wu Z, Xie Q, Fang J, Hu Y, Lu M, Xia F, Nie Y, Ji J, J. Clean Prod., 186, 1021 (2018)
- Adhami K, Asadollahzadeh H, Ghazizadeh M, J. Ind. Eng. Chem., 76, 245 (2019)
- Chua SY, Periasamy LAP, Goh CMH, Tan YH, Mubarak NM, Kansedo J, Khalid M, Walvekar R, Abdullah EC, J. Ind. Eng. Chem., 81, 41 (2020)
- Kousaalya AB, Beyene SD, Gopal V, Ayalew B, Pilla S, Ind. Crop. Prod., 123, 25 (2018)
- Carbonellverdu A, Bernardi L, Garciagarcia D, Sancheznacher L, Balart R, Eur. Polym. J., 63, 1 (2015)
- Fombuena V, Sanchez-Nacher L, Samper MD, Juarez D, Balart R, J. Am. Oil. Chem. Soc., 90, 449 (2013)
- Huang X, Yang X, Liu H, Shang S, Cai Z, Wu K, Ind. Crop. Prod., 139, 111540 (2019)
- Liu K, Madbouly SA, Kessler MA, Eur. Polym. J., 69, 16 (2015)
- Wu Q, Hu Y, Tang J, Zhang J, Wang C, Shang Q, Feng G, Liu C, Zhou Y, Lei W, ACS Sustain. Chem. Eng., 6, 8340 (2018)
- Zhang Y, Li Y, Thakur VK, Wang L, Gu J, Gao Z, Fan B, Wu Q, Kessler MR, RSC Adv., 8, 13780 (2018)
- Zhang Y, Thakur VK, Li Y, Garrison TF, Gao Z, Gu J, Kessler MR, Macromol. Mater. Eng., 303, 170027 (2018)
- Sienkiewicz AM, Czub P, Ind. Crop. Prod., 83, 755 (2016)
- Wang J, Liu Y, Zhou ZN, Fu Y, Chang J, Ind. Eng. Chem. Res., 56(29), 8224 (2017)
- Hazer B, J. Polym. Environ., 22, 200 (2014)
- Gramlich WM, Robertson ML, Hillmyer MA, Macromolecules, 43(5), 2313 (2010)
- Kleiner J, Hinrichsen O, Chem. Eng. Process., 136, 152 (2019)
- Vianello C, Piccolo D, Lorenzetti A, Salzano E, Maschio G, Ind. Eng. Chem. Res., 57(34), 11517 (2018)
- Bhaumik P, Dhepe PL, Catal. Rev., 58, 36 (2016)
- Xincheng T, Shengli N, J. Ind. Eng. Chem., 69, 187 (2019)
- Aguilera AF, Tolvanen P, Heredia S, Munoz MG, Samson T, Oger A, Verove A, Eranen K, Leveneur S, Mikkola JP, Salmi T, Ind. Eng. Chem. Res., 57(11), 3876 (2018)
- Shibasaki-Kitakawa N, Hiromori K, Ihara T, Nakashima K, Yonemoto T, Fuel, 139, 11 (2015)
- Mai HD, Kim SC, Yoo HJ, J. Ind. Eng. Chem., 82, 359 (2020)
- Tran NM, Jung S, Yoo H, Nano Res., 13, 775 (2020)
- Gamero M, Valle B, Castano P, Aguayo AT, Bilbao J, J. Ind. Eng. Chem., 61, 427 (2018)
- Hita I, Cordero-Lanzac T, Bonura G, Cannilla C, Arandes JM, Frusteri F, Bilbao J, J. Ind. Eng. Chem., 80, 392 (2019)
- Kołodynska D, Hałas P, Franus M, Hubicki Z, J. Ind. Eng. Chem., 52, 187 (2017)
- Bhalerao MS, Kulkarni VM, Patwardhan AV, Ultrason. Sonochem., 40, 912 (2018)
- Mashhadi F, Habibi A, Varmira K, Ind. Crop. Prod., 113, 324 (2018)
- Wilde N, Prech J, Pelz M, Kubu M, Cejka J, Glaser R, Catal. Sci. Technol., 6, 7280 (2016)
- Wroblewska A, Malko M, Walasek M, Pol. J. Chem. Technol., 20, 6 (2018)
- Fadhli M, Khedher I, Fraile JM, J. Mol. Catal. A-Chem., 420, 282 (2016)
- Du MM, Huang J, Sun DH, Li QB, Appl. Surf. Sci., 366, 292 (2016)
- Chen C, Cai L, Li L, Bao L, Lin Z, Wu G, Microporous Mesoporous Mater., 276, 89 (2019)
- Harris JW, Arvay J, Mitchell G, Delgass WN, Ribeiro FH, J. Catal., 365, 105 (2018)
- Hu T, Liu J, Cao C, Song W, Chin. J. Catal., 38, 872 (2017)
- Li JC, Li JM, Zhao Z, Fan XQ, Liu J, Wei YC, Duan AJ, Xie Z, Liu QL, J. Catal., 352, 361 (2017)
- Tekla J, Tarach KA, Olejniczak Z, Girman V, Gora-Marek K, Microporous Mesoporous Mater., 233, 16 (2016)
- Ye X, Cui Y, Qiu X, Wang X, Appl. Catal. B: Environ., 152-153, 383 (2014)
- Wu M, Song HL, Wang F, Chou LJ, J. Mol. Catal. A-Chem., 379, 207 (2013)
- Wu M, Chou L, Song H, Chin. J. Catal., 34, 789 (2013)
- Wu G, Xiao J, zhang L, Wang W, Hong Y, Huang H, Jiang Y, Li L, Wang C, RSC Adv., 6, 101071 (2016)
- Ding Y, Gao Q, Wang B, Li G, Yan L, Suo J, J. Porous Mat., 12, 131 (2005)
- Dai J, Zhong WZ, Yi WJ, Liu MQ, Mao LQ, Xu Q, Yin DL, Appl. Catal. B: Environ., 192, 325 (2016)
- Wu G, Wang Y, Wang L, Feng W, Shi H, Lin Y, zhang T, Jin X, Wang S, Wu X, Yao P, Chem. Eng. J., 215-216, 306 (2013)
- Campanella A, Baltanas MA, Capel-Sanchez MC, Campos-Martin JM, Fierro JLG, Green Chem., 6, 330 (2004)
- Zhang H, Yang H, Guo H, Yang J, Xiong L, Huang C, Chen X, Ma L, Chen Y, Appl. Clay Sci., 90, 175 (2014)
- Rothenbacher T, Schwack W, Rapid Commun. Mass Spectrom., 21, 1937 (2007)
- Talipova RR, Kharrasov RU, Veklov VA, Badikova AD, Kutepov BI, Pet. Chem., 57(5), 395 (2017)
- Du C, Cui N, Li L, Hua Z, Shi J, RSC Adv., 9, 9694 (2019)
- Lewis RJ, Ueura K, Fukuta Y, Freakley SJ, Kang L, Wang R, et al., ChemCatChem, 11, 1673 (2019)
- Scarano D, Zecchina A, Bordiga S, Geobaldo F, Spoto G, Petrini G, Leofanti G, Padovan M, Tozzola G, J. Chem. Soc.-Faraday Trans., 89, 4123 (1993)
- Wang B, Lu L, Ge B, Chen S, Zhu J, Wei D, J. Porous Mat., 26, 227 (2019)
- Bordiga S, Damin A, Bonino F, Zecchina A, Spano G, Rivetti F, Bolis V, Prestipino C, Lamberti C, J. Phys. Chem. B, 106(38), 9892 (2002)
- Ricchiardi G, Damin A, Bordiga S, Lamberti C, Spano G, Rivetti F, Zecchina A, J. Am. Chem. Soc., 123(46), 11409 (2001)
- Wu GQ, Lin ZG, Li L, Zhang L, Hong YP, Wang WJ, Chen C, Jiang Y, Yan XZ, Chem. Eng. J., 320, 1 (2017)
- Maksimchuk NV, Ivanchikova ID, Ayupov AB, Kholdeeva OA, Appl. Catal. B: Environ., 181, 363 (2016)
- Zhang HJ, Liu YM, Jiao Z, He MY, Wu P, Ind. Eng. Chem. Res., 48(9), 4334 (2009)
- Alba-Rubio AC, Fierro JLG, Leon-Reina L, Mariscal R, Dumesic JA, Granados ML, Appl. Catal. B: Environ., 202, 269 (2017)
- Zhang T, Chen X, Chen G, Chen M, Bai R, Jia M, Yu J, J. Mater. Chem. A, 6, 9473 (2018)
- Choi KM, Burri DR, Han SC, Park SE, Solid State Phenom., 119, 167 (2007)
- Peng L, Zeng QR, Tie BQ, Lei M, Yang J, Luo S, Song ZG, J. Colloid Interface Sci., 456, 108 (2015)
- Wu Y, Song X, Zhan gJ, Li S, Yang X, Wang H, Wei R, Gao L, Zhang J, Xiao G, J. Taiwan Inst. Chem. Eng., 87, 131 (2018)
- Saravanakumar K, Muthuraj V, Jeyaraj M, Spectroc. Acta Pt. A-Molec. Biomolec. Spectr., 188, 291 (2018)
- Lingampalli SR, Gautam UK, CrystEngComm, 16, 1050 (2014)
- Peng Y, Li J, Si W, Luo J, Wang Y, Fu J, Li X, Crittenden J, Hao J, Appl. Catal. B: Environ., 168-169, 195 (2015)
- Song H, Zhao LL, Wang N, Li F, Appl. Catal. A: Gen., 526, 37 (2016)
- Yoosuk B, Silajan A, Prasassarakich P, J. Clean Prod., 248, 119291 (2020)