Abstract
Liquid phase hydrodearomatization (HDA) of monoaromatic model molecules (toluene, indane, tetralin, cyclohexylbenzene, nonylbenzene) from naphtha and middle distillate was conducted at a temperature of 170 °C and a pressure of 100 bar over Ni/Al2O3 in order to compare their reactivity separately and in mixture. A reactivity scale was established where toluene is more reactive than tetralin, indane, cyclohexylbenzene and nonylbenzene. The difference of reactivity is due to steric hindrance of the substituent and its electronic effect. In all cases, the fully hydrogenated product is the main product. Toluene hydrodearomatization is inhibited by the presence of another monoaromatics. This inhibition effect is more significant with indane than with cyclohexylbenzene and nonylbenzene and tetralin corresponding to competitive adsorptions and highlighted by kinetic modeling.
Graphical Abstract
Similar content being viewed by others
References
Cooper BH, Donnis BBL (1996) Appl Catal A 137:203–223
Girgis MJ, Gates BC (1991) Ind Eng Chem Res 30:2012–2058
Dath J-P, Minoux D, Chassard O (2016) WO/2016/001302, Total
Altgelt KH, Boduszynski MM (1993) Composition and analysis of heavy petroleum fractions. CRC Press, New York
Jennerwein M, Eschner M, Gröger T, Wilharm T, Zimmermann R (2014) Energy Fuels 28:5670–5681
Adam F, Bertoncini F, Coupard V, Charon N, Thiébaut D, Espinat D, Hennion M-C (2008) J Chromatogr A 1186:236–244
Chowhudry R, Pedernera E, Reimert R (2002) AIChE J 48:126–135
Stanislaus A, Cooper BH (1994) Catal Rev Sci Eng 36:75–123
Korre SC, Klein MT, Quann RJ (1995) Ind Eng Chem Res 34:101–117
Beltramone AR, Resasco DE, Alvarez WE, Choudhary TV (2008) Ind Eng Chem Res 47:7161–7166
Sapre AV, Gates BC (1981) Ind Eng Chem Proc Des Dev 20:68–73
Kishore Kumar SA, John M, Pai SM, Niwate Y, Newalkar BL (2014) Fuel Process Technol 128:303–309
Castaño P, van Herk D, Kreutzer MT, Moulijn JA, Makkee M (2009) Appl Catal B 88:213–223
Aubert C, Durand R, Geneste P, Moreau C (1988) J Catal 112:12–20
Xin L, Liu X, Chen X, Feng X, Liu Y, Yang C (2017) Energy Fuels 31:6968–6976
Tailleur RG (2006) Fuel Process Technol 87:759–767
Weitkamp AW (1968) Adv Catal 18:1–110
Korre SC, Neurock M, Klein MT, Quann RJ (1994) Chem Eng Sci 49:4191–4210
Jongpatiwut S, Li Z, Resasco DE, Alvarez WE, Sughrue EL, Dodwell GW (2004) Appl Catal A 262:241–253
Chou P, Vannice MA (1987) J Catal 107:129–139
Vasiur Bahaman M, Vannice MA (1991) J Catal 127:251–266
Keane MA (1997) J Catal 166:347–355
Bera T, Thybaut JW, Marin GB (2012) ACS Catal 2:1305–1318
Huang T-C, Kang B-C (1995) Ind Eng Chem Res 34:1140–1148
Rautanen PA, Lylykangas MS, Aittamaa JR, Krause AOI (2001) Stud Surf Sci Catal 133:309–316
Rautanen PA, Lylykangas MS, Aittamaa JR, Krause AOI (2002) Ind Eng Chem Res 41:5966–5975
Frye CG, Weitkamp W (1969) J Chem Eng Data 14:372–376
Rautanen PA, Aittamaa JR, Krause AOI (2001) Chem Eng Sci 56:1247–1254
Singh UK, Vannice MA (1999) AIChE J 45:1059–1071
Rautanen PA, Aittamaa JR, Krause AOI (2000) Ind Eng Chem Res 39:4032–4039
Jaffe SB (1974) Ind Eng Chem Proc Des Dev 13:34–39
Ferraz SGA, Santos BM, Zotin FM, Araujo LRR, Zotin J (2015) Ind Eng Chem Res 54:2646–2656
Liu H, Liu C, Yin C, Liu B, Li X, Li Y, Chai Y, Liu Y (2016) Catal Today 276:46–54
Romero CMC, Thybaut JW, Marin GB (2008) Catal Today 130:231–242
Suppino RS, Landers R, Cobo AJG (2016) Appl Catal A 525:41–49
Ledesma BC, Vallés VA, Rivoira LP, Martinez ML, Anunziata OA, Beltramone AR (2014) Catal Lett 144:783–795
Toppinen S, Rantakylä TK, Salmi T, Aittamaa JR (1996) Ind Eng Chem Res 35:1824–1833
Lylykangas MS, Rautanen PA, Krause AOI (2002) Ind Eng Chem Res 41:5632–5639
Rahaman MV, Vannice MA (1991) J Catal 127:251–266
Völter J, Hermann M, Heise K (1968) J Catal 12:307–313
Dufresne P, Bigeard PH, Billon A (1987) Catal Today 1:367–384
Toppinen S, Rantakylä TK, Salmi T, Aittamaa JR (1996) Ind Eng Chem Res 35:4424–4433
Poondi D, Vannice MA (1996) J Catal 161:742–751
Rader CP, Smith HA (1962) J Am Chem Soc 84:1443–1449
Toppinen S, Salmi T, Rantakylä TK, Aittamaa JR (1997) Ind Eng Chem Res 36:2101–2109
Abon M, Bertolini JC, Billy J, Massardier J, Tardy B (1985) Surf Sci 162:395–401
Kieboom APG (1976) Bull Chem Soc Jpn 49:331–332
Keane MA, Patterson PM (1999) Ind Eng Chem Res 38:1295–1305
Fonseca GS, Silveira ET, Gelesky MA (2005) J Dupont Adv Synth Catal 347:847–853
Dokjampa S, Rirksomboon T, Osuwan S, Jongpatiwut S, Resasco DE (2007) Catal Today 123:218–223
Monteiro-Gezork ACA, Natividad R, Winterbottom JM (2008) Catal Today 130:471–485
Oh SH, Fisher GB, Carpenter JE, Goodman DW (1986) J Catal 100:360–376
Karakaya C, Otterstätter R, Maier L, Deutschmann O (2014) Appl Catal A 470:31–44
Acknowledgements
J. Deligny acknowledges Total and ANRT for a PhD grant and Johnson Mathey for the catalyst.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Deligny, J., Germanaud, L., Dath, JP. et al. Hydrodearomatization of Model Monoaromatics Over Ni/Al2O3: Theoretical and Experimental Approaches. Catal Lett 148, 2548–2560 (2018). https://doi.org/10.1007/s10562-018-2440-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10562-018-2440-2