Prediction of 1,3,5-triisopropylbenzene cracking pattern through thermodynamic evaluation of products and protonation intermediates

Sanchez, Astrid; Ramirez, Susana; Silva-López, Wilber; Espinal, Juan F.

doi:10.1016/j.mcat.2018.12.019

Cited by 7 publications

(5 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The molecular size of 1,3,5-triisopropylbenzene (TIPB; critical diameter of 0.95 nm) is too large to enter the 12-ring channels of MOR zeolite, and its reaction only occurs on the external surface. − However, the cracking of cumene (critical diameter of 0.68 nm) can take place both on the external surface and inside pores . Thus, here cumene/1,3,5-triisopropylbenzene cracking was used to appraise the change of the internal/external acidity of the 3.0%Ni–HMOR treated with silicon deposition. , As shown in Figure , with the increase of the cycle times of silicon deposition, the SiO 2 -modified sample showed a significantly decreased conversion of 1,3,5-triisopropylbenzene, while cumene conversion was always kept at a high level (>31.8%).…”

Section: Resultsmentioning

confidence: 99%

Transalkylation of C₁₀ Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO₂–Ni–H-Mordenite with Nanosheet Crystal

Xie

Liang

Zhou

et al. 2021

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

A reasonable control of the reaction pathways in the reaction system of the transalkylation of C 10 aromatics with 2methylnaphthalene was achieved over a shape-selective SiO 2 (II)− 3.0%Ni−H-mordenite (HMOR) with nanosheet crystals in a H 2 atmosphere. First, significantly improved reactivity was obtained depending on the synergistic catalysis from acid sites and metal Ni sites only on the internal surface, maybe due to a process where spillover hydrogen was converted into active hydrogen species and the latter greatly enhanced the proton-transfer efficiency in this surface catalysis. Second, based on the external surface passivation with little influence on the intrinsic excellent pore diffusibility of lamellar crystals, the side reactions of naphthalene nucleus ring opening and methylnaphthalene polyalkylation involved in largemolecule intermediates were significantly suppressed by the shape-selectivity restriction inside channels, meanwhile with remarkably enhanced dimethylnaphthalene selectivity. Both porous shape selectivity and a reasonably decreased acid strength also weakened the secondary conversion of β,β-dimethylnaphthalenes into other isomers. Therefore, an obviously improved selectivity of 2,6dimethylnaphthalene was gained. Also, a reasonable hydrogenation catalyzed by metal Ni sites strongly resisted coke deposition, and this created a good catalytic stability of this catalyst with an impressive capability of accommodating coke. As a result, a 2methylnaphthalene conversion of above 67.1% and a 2,6-dimethylnaphthalene yield of above 10.7% were obtained during a 100 h on stream reaction.

show abstract

Section: Resultsmentioning

confidence: 99%

Transalkylation of C₁₀ Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO₂–Ni–H-Mordenite with Nanosheet Crystal

Xie

Liang

Zhou

et al. 2021

Ind. Eng. Chem. Res.

View full text Add to dashboard Cite

show abstract

“…Deep cracking of 1,3,5-TIPB is a term coined by Hosseinpour et al to describe the formation of cumene (and benzene) arising from the successive dealkylation of DIPB (and cumene) to benzene and propylene. [58,59] Note that a high propylene yield is not indicative of deep cracking as it may simply reflect high 1,3,5-TIPB conversion to diisopropylbenzene, whereas cumene and benzene yields are direct measures of deep cracking. Relationships between deep cracking and mesoporosity are previously discussed for zeolites.…”

Section: Catalytic Cracking Of 135-tipbmentioning

confidence: 99%

Catalytic Cracking of 1,3,5‐Triisopropylbenzene and Low‐Density Polyethylene over Hierarchical Y Zeolites and Al‐SBA‐15

Mensah,

Yan,

Rawal

et al. 2023

ChemCatChem

View full text Add to dashboard Cite

Catalytic cracking of high molecular weight hydrocarbons underpins the production of fossil fuels from petroleum vapour and the recycling of polyolefin waste plastic. However, thermal cracking over conventional microporous solid acids is hindered by poor mass‐transport. Here we explore the performance of hierarchical H‐Y zeolites and Al‐SBA‐15 for the catalytic cracking of 1,3,5‐triisopropylbenzene (1,3,5‐TIPB) and low‐density polyethylene (LDPE) in a continuous fixed‐bed flow reactor. Single and multiple demetallation strategies (dealumination, desilication and/or acid washing) were used to create hierarchical mesoporosity in H‐Y zeolite and modify the solid acidity. Physicochemical properties were studied by X‐ray diffraction (XRD), transmission electron microscopy (TEM), scanning electron microscopy (SEM), gas adsorption, in‐situ Fourier transform infrared (FTIR), and 29Si and 27Al nuclear magnetic resonance (NMR). Dealumination and sequential dealumination‐desilication‐acid washing promote the selective deep cracking of both feedstocks; HNO3 dealuminated H‐Y produces six times more propene from 1,3‐5‐TIPB, and ~30% more benzene and xylenes from LDPE, than the parent H‐Y.

show abstract

“…The main component of the gas obtained from the cracking of TIPB was propylene (C 3 = ), that is formed by the three sequential events starting with the TIPB adsorption on the Brønsted acid site that leads to the formation of the planar carbenium ion ([TIPB] + ) on the catalyst surface, then, followed a bimolecular reaction that leads to the abstraction of an hydride and breaks the C-C bond between the benzene ring and the isopropyl substituent through β scission (Sanchez et al 2019;Qi et al 2011). However, other secondary gas products such as propane (C 3 ), iso-butane (iC 4 ) and iso-pentane (iC 5 ) were obtained (Table 5).…”

Section: Catalytic Performance Of Samplesmentioning

confidence: 99%

“…Three main reaction products corresponding to the loss of the isopropyl substituent, such as 1,3-diisopropylbenzene (1,3-DIPB), isopropylbenzene (IPB) and benzene were identified, and other aromatic compounds with lower yields such as ethylbenzene (C 8 H 10 ) and 1,2-dimethyl-3-ethylbenzene (C 10 H 14 ) were also analyzed. Following the scheme of successive dealkylation reactions of TIPB for the production of propylene molecules, 1,3-DIPB is formed after the rupture of one σ bond (Sanchez et al 2019;Al-Khattaf and Lasa 2002;Falco et al 2006); however, the 1,4-DIPB isomer was also identified in the PIANO analysis as a secondary product of isomerization. According to data presented in Table 5 1,3-DIPB yields are approximately three times higher than 1,4-DIPB, indicating that approximately a 25% of the 1,3-DIPB was isomerized.…”

Section: Catalytic Performance Of Samplesmentioning

confidence: 99%

Synthesis and catalytic behavior of FCC catalysts obtained from kaolin by the in-situ method

Padilla

Guzmán

Poveda-Jaramillo

2022

Braz. J. Chem. Eng.

View full text Add to dashboard Cite

In-situ zeolites NaY and Na[B]Y were synthesized on microspherical matrices of kaolin to obtain FCC catalysts. An alkaline pretreatment of the matrix was investigated in order to evaluate its effect on matrix properties and crystallization of the in-situ synthetized zeolites. Catalysts were characterized by SEM, TEM, Ar adsorption, XRD and NH3-TPD. It was observed an increase in the surface area and mesoporosity of the alkaline treated catalysts either synthetized with the presence of boron or with no boron in the hydrothermal reaction mixture. Ammonia TPD analyses have shown an increase in the amount and strength of the acidity of the catalysis with the zeolites crystallized on the pretreated matrices and exchanged with lanthanum ions. Thus, a combination between higher concentration of stronger acid sites and higher proportion of mesoporous generated in the matrices treated with alkaline solution had resulted in more active catalyst as shown by the triisopropylbenzene cracking experiments conducted here. Graphical abstract

show abstract

Prediction of 1,3,5-triisopropylbenzene cracking pattern through thermodynamic evaluation of products and protonation intermediates

Cited by 7 publications

References 29 publications

Transalkylation of C₁₀ Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO₂–Ni–H-Mordenite with Nanosheet Crystal

Transalkylation of C₁₀ Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO₂–Ni–H-Mordenite with Nanosheet Crystal

Catalytic Cracking of 1,3,5‐Triisopropylbenzene and Low‐Density Polyethylene over Hierarchical Y Zeolites and Al‐SBA‐15

Synthesis and catalytic behavior of FCC catalysts obtained from kaolin by the in-situ method

Contact Info

Product

Resources

About

Prediction of 1,3,5-triisopropylbenzene cracking pattern through thermodynamic evaluation of products and protonation intermediates

Cited by 7 publications

References 29 publications

Transalkylation of C10 Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO2–Ni–H-Mordenite with Nanosheet Crystal

Transalkylation of C10 Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO2–Ni–H-Mordenite with Nanosheet Crystal

Catalytic Cracking of 1,3,5‐Triisopropylbenzene and Low‐Density Polyethylene over Hierarchical Y Zeolites and Al‐SBA‐15

Synthesis and catalytic behavior of FCC catalysts obtained from kaolin by the in-situ method

Contact Info

Product

Resources

About

Transalkylation of C₁₀ Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO₂–Ni–H-Mordenite with Nanosheet Crystal

Transalkylation of C₁₀ Aromatics with 2-Methylnaphthalene for 2,6-Dimethylnaphthalene Synthesis over a Shape-Selective SiO₂–Ni–H-Mordenite with Nanosheet Crystal