Alkylation of isobutane with C4 olefins. 3. Two-step process using sulfuric acid as catalyst

Albright, Lyle F.; Spalding, Mark A.; Faunce, Janelle; Eckert, Roger E.

doi:10.1021/ie00075a005

Cited by 56 publications

(59 citation statements)

References 6 publications

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“…This route was similar to the mechanism of the H 2 SO 4 -catalyzed system . In the alkylate, TMP-123 (with molecular weight 123; C 8 H 9 D 9 ) was detected, which could be due to the direct alkylation between deuterated isobutane and 2-butene.…”

Section: Mechanism Of Alkylation Reactionssupporting

confidence: 67%

“…The tert -butyl carbocation reacts with 2-butene quickly to form the TMP carbocation, which then is converted to TMP (major product in alkylate) via hydride transfer from isobutane, and the tert -butyl carbocation is restored. In the intermediate step, TMP carbocation can isomerize and form different forms of TMPs through hydride and methyl shifts. − Wang et al studied the C 4 alkylation mechanism using density functional theory and found the stability of TMP cations (2,2,4- sec -TMP + > 2,3,4- tert -TMP + > 2,2,3- tert -TMP + ) trend in accordance with the TMPs selectivity in the obtained alkylate …”

Section: Mechanism Of Alkylation Reactionsmentioning

confidence: 96%

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Review of Isobutane Alkylation Technology Using Ionic Liquid-Based Catalysts—Where Do We Stand?

Kore

Scurto

Shiflett

2020

Ind. Eng. Chem. Res.

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Conventional strong liquid acids such as H 2 SO 4 and HF are used for the majority of current commercial isobutane alkylation processes to produce motor fuel alkylates, but these acids can have significant safety and sustainability concerns. Ionic liquid (IL) catalyst technologies offer potential advantages over current processes due to the negligible vapor pressure and molecularly tunable properties that can optimize both the chemistry and engineering for alkylate production. In this review, IL-based catalysts used in isobutane alkylation are reviewed. ILs are categorized and discussed by type: (1) metal-based Lewis acidic ILs, (2) metal-based Bronsted−Lewis acidic ILs, (3) nonmetal-based Bronsted acidic ILs, and (4) immobilized/supported ILs. A critical perspective on the use of these ILs in alkylation is presented, focusing on the effect of speciation and physicochemical properties on chemical reaction. Further, a summary of IL speciation is provided and examples of how the tunability of ILs can be used to overcome current limitations in alkylation chemistry. The reaction conditions and performance (e.g., conversion, C 8 selectivity, and trimethylpentane:dimethylhexane ratio) of literature reports are summarized. A comparison of IL-based catalysts with the incumbent H 2 SO 4 process and the new ISOALKY Chevron process are also discussed. Gaps in the literature (e.g., mass transfer rates, material compatibilities, and phase equilibrium) associated with IL-based alkylation technology and our perspectives on solving the relevant issues in this field are summarized.

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Section: Mechanism Of Alkylation Reactionssupporting

confidence: 67%

Section: Mechanism Of Alkylation Reactionsmentioning

confidence: 96%

Review of Isobutane Alkylation Technology Using Ionic Liquid-Based Catalysts—Where Do We Stand?

Kore

Scurto

Shiflett

2020

Ind. Eng. Chem. Res.

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“…Therefore, it is conclusive that low temperatures are favorable for the alkylation of isobutane/2-butene catalyzed by the BMIC-2AlCl 3 /thioalcohol ionic liquid. This characteristic is similar to the alkylation catalyzed by sulfuric acid [31,32] or aluminium chloride [24].…”

Section: Effect Of Temperaturementioning

confidence: 58%

Alkylation of isobutane and butene using chloroaluminate imidazolium ionic liquid as catalyst: Effect of organosulfur compound additive

Zhang

Huang

Chen

et al. 2008

Korean J. Chem. Eng.

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Alkylation of isobutane and butene was carried out in a batch unit using 1-butyl-3-methylimidazolium chloride (BMIC)-aluminium (III) chloride (AlCl 3 ) ionic liquid as catalyst. The effects of additives of butyl thioalcohol and ethyl thioether on the properties of ionic liquids for alkylation were investigated. Improvement of production distribution with high yields of isooctane and selectivity of TMP under a mild reaction condition was observed after addition of butyl thioalcohol. Moreover, the effects of operating variables were investigated and the mechanism was discussed.

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“…Alkylate, produced by the C4 alkylation reaction, has the advantages of a high octane number, low vapor pressure, very low sulfur content, and cleaning combustion, which is recognized as an ideal blending component for gas upgrading . Currently, commercial alkylation processes are primarily catalyzed by concentrated sulfuric acid (H 2 SO 4 ) and hydrofluoric acid (HF). , However, the HF catalyst has high toxicity, high volatility, and potential safety hazards, and the H 2 SO 4 -catalyzed process suffers from high catalyst consumption, equipment corrosion, and environmental pollution. , To cope with these issues of liquid catalysts, various solid acids were investigated as the catalyst for alkylation, including sulfated zirconia, , heteropolyacids, , acid resins, chlorinated alumina, and the most commonly used acidic zeolites. − …”

Section: Introductionmentioning

confidence: 99%

Understanding the Promotion of Solid Acid-Catalyzed Isobutane Alkylation with Butene by Hydrophilic/Hydrophobic Surface Modification

et al. 2021

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The adsorption and diffusion behaviors of isobutane, 2-butene, and trimethylpentane (TMP) on the silica surface with various surface groups were investigated using molecular dynamics (MD) simulations in this work. A significant concentration gradient and density enhancement of isobutane and butene were observed on the silica surface due to their strong interaction with surface groups. The hydrophobic modification of the silica surface can improve the adsorption ratio of isoparaffin to olefins (I/O), further inhibiting the catalyst deactivation. However, the hydrophilic modification will increase the surface polarity and the interaction between propanesulfonic acid groups and butene, which is not beneficial for the alkylation reaction. The diffusion rate of molecules is affected by their size and follows the order of 2-butene > isobutane > TMP, while the difference between isobutane and 2-butene is the smallest in the hydrophobically modified system. Both surface modification and the presence of the C8 product will inhibit the diffusion and update rate of C4 hydrocarbons, while the increase in temperature will promote their diffusion. Hopefully, this work would bring deep insights into the countermeasures of solid acid deactivation.

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Alkylation of isobutane with C4 olefins. 3. Two-step process using sulfuric acid as catalyst

Cited by 56 publications

References 6 publications

Review of Isobutane Alkylation Technology Using Ionic Liquid-Based Catalysts—Where Do We Stand?

Review of Isobutane Alkylation Technology Using Ionic Liquid-Based Catalysts—Where Do We Stand?

Alkylation of isobutane and butene using chloroaluminate imidazolium ionic liquid as catalyst: Effect of organosulfur compound additive

Understanding the Promotion of Solid Acid-Catalyzed Isobutane Alkylation with Butene by Hydrophilic/Hydrophobic Surface Modification

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