Abstract
On Amberlyst® 15 catalyst (dry) at 85 °C, 1-dodecene underwent concurrent double bond isomerization and alkylation with p-xylene. The alkylation reaction appeared to occur by an Eley–Rideal mechanism in which adsorbed olefin reacted with bulk phase p-xylene. Kinetic data showed that alkylation was irreversible and that the intermediate complex between olefin and p-xylene underwent isomerization in which the aromatic ring moved between adjacent carbons on the dodecyl chain. Given enough reaction time, the dodecyl p-xylene isomers always reached the same equilibrium distribution, regardless of catalyst loading. Kinetic modeling of concurrent olefin isomerization and alkylation showed that these two reactions must occur on two different catalytic sites. Alkylation was inhibited by the formation of dodecyl p-xylenes, while double bond isomerization was not.
Similar content being viewed by others
References
Fernandes RM, Lachter ER (2005) Catal Commun 6:550
Buttersack C, Widdecke H, Klein J (1986) J Mol Catal 38:365
Nel RJJ, de Klerk A (2007) Ind Eng Chem Res 46:2902
Petre AL, Hoelderich WF, Gorbaty ML (2009) Appl Catal A 363:100
Yadav GD, Siddiqui MINI (2009) Ind Eng Chem Res 48:10803
Freire MA, Mendes DTSL, Freitas LS, Beerthuis R, Amarante SF, Ramos ALD (2017) Catal Today 289:192
Yadav GD, Doshi NS (2002) Org Proc Res Dev 6:263
Howe-Grant M (1992) Kirk-Othmer encyclopedia of chemical technology, vol 2, 4th edn. Wiley, New York, pp 100–106
Gee JC, Kattchee LM, Gee SJ (2014) J Phys Org Chem 27:583
Olah GA (1971) Acc Chem Res 4:240
Olah GA, Kobayashi S, Tashiro M (1972) J Am Chem Soc 94:7448
Chiavarino B, Crestoni ME, Fornarini S, Lemaire J, Maitre P, MacAleese L (2006) J Am Chem Soc 128:12553
Lenoir D (2003) Angew Chem Int Ed 42:854
Dange PN, Sharma A, Rathod VK (2014) Catal Lett 144:1537
Lilja J, Aumo J, Salmi T, Murzin DY, Mäki-Arvela P, Sundell M, Ekman K, Peltonen R, Vainio H (2002) Appl Catal A 228:253
Sert E, Atalay FS (2010) Prog Reac Kinetics Mech 35:219
Gee JC, Fisher S (2015) J Catal 331:13
Słomkiewicz PM (2004) Appl Catal A 269:33
Bringué R, Ramírez E, Montserrat I, Javier T, Cunill F (2013) J Catal 304:7
Gee JC, Williams ST (2013) J Catal 303:1
Lente G (2018) Curr Opin Chem Eng 21:76
Gee JC, Jeansonne MS, Yang H, Fisher S (2017) Reac Kinet Mech Cat 122:21
Levenberg K (1944) Q Appl Math 2:164
Marquardt DW (1963) SIAM J App Math 11:431
Press WH, Flannery BP, Teukolsky SA, Vetterling WT (1986) Numerical recipes in pascal. Cambridge University Press, Cambridge
Gee JC, Prampin DS (2009) Appl Catal A 360:71
Acknowledgements
We thank Rachel Franklin for providing proton NMR spectra, and we thank Chevron Phillips Chemical Company LP for permission to publish this work.
Author information
Authors and Affiliations
Corresponding author
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Gee, J.C., Stansifer, R.D. Kinetic evidence for two different active sites on dry Amberlyst® 15 catalyst in the alkylation between 1-dodecene and p-xylene. Reac Kinet Mech Cat 126, 879–901 (2019). https://doi.org/10.1007/s11144-019-01557-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11144-019-01557-1