Benzene alkylation with long chain olefins catalyzed by ionic liquids: a review

Qiao, Congzhen; Cai, Yanpeng

doi:10.1007/s11705-008-0045-9

Cited by 12 publications

(5 citation statements)

References 32 publications

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“…418 Earlier Qiao wrote a review on benzene alkylation with long chain olefins catalyzed by ionic liquids as well, and this review is particularly focused on the applications of chloroaluminate ionic liquids in benzene alkylation of special interest to petrochemical and detergent industry. 419 The Friedel−Crafts type alkylation at a carbon atom is the most common application in acidic ionic liquid catalyzed alkylations. 420−424 However, there are examples of alkylations at N, O and S atoms as well.…”

Section: Catalysis Applicationsmentioning

confidence: 99%

“…The methods used in the determination of acidity, application of acidic ionic liquids in alkylation, acidic adjustment methods, and novel acidic ionic liquids are discussed in this review article with 38 references . Earlier Qiao wrote a review on benzene alkylation with long chain olefins catalyzed by ionic liquids as well, and this review is particularly focused on the applications of chloroaluminate ionic liquids in benzene alkylation of special interest to petrochemical and detergent industry …”

Section: Applications Of Acidic Ionic Liquidsmentioning

confidence: 99%

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Acidic Ionic Liquids

2016

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Ionic liquid with acidic properties is an important branch in the wide ionic liquid field and the aim of this article is to cover all aspects of these acidic ionic liquids, especially focusing on the developments in the last four years. The structural diversity and synthesis of acidic ionic liquids are discussed in the introduction sections of this review. In addition, an unambiguous classification system for various types of acidic ionic liquids is presented in the introduction. The physical properties including acidity, thermo-physical properties, ionic conductivity, spectroscopy, and computational studies on acidic ionic liquids are covered in the next sections. The final section provides a comprehensive review on applications of acidic ionic liquids in a wide array of fields including catalysis, CO2 fixation, ionogel, electrolyte, fuel-cell, membrane, biomass processing, biodiesel synthesis, desulfurization of gasoline/diesel, metal processing, and metal electrodeposition.

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Section: Catalysis Applicationsmentioning

confidence: 99%

Section: Applications Of Acidic Ionic Liquidsmentioning

confidence: 99%

Acidic Ionic Liquids

2016

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“…In recent years, ionic liquids have attracted much interest for their unique properties such as non-volatility, non-flammability, high chemical and thermal stability. [11][12][13][14][15] [AlCl3] would result in high activity. These kinds of ionic liquid catalysts could not be reused for many times because of their moisture sensitivity.…”

Section: Introductionmentioning

confidence: 99%

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Wan

Zhang

et al. 2015

RSC Adv.

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Friedel-Craft alkylation of benzene with 1-dodecene, which is an important reaction of synthetic detergent, was studied using the catalyst of [bmim][TFSI]/AlCl3 (1-butyl-3-methylimidazolium bis((trifluoromethyl)sulfonyl)imide/AlCl3). These ionic liquid catalysts show biphasic behaviors at specific condition. Active site species and Lewis acidity were determined by NMR and acetonitrile probe FT-IR. NMR spectroscopy investigations indicated that "Coordinated" and "uncoordinated"[TFSI]existed in the ionic liquid catalyst system sumultaneity, while tetrahedral 4-coordinate Al2Cl7was the main active specie for Friedel-Craft alkylation. The complexation [AlClx(TFSI)y]tend to decompose and release 4-coordinated Al2Cl7and [TFSI] -. The phase behaviors study of the ionic liquid [bmim][TFSI]/AlCl3 demonstrated that the upper phase could be used as an efficient heterogeneous catalyst when AlCl3/IL≥1.5. Due to the presence of anion [TFSI]around active sites, especially [TFSI]at "uncoordinated" state, ionic liquid formed a stable and hydrophobic chemical environment, which enhanced catalysts durability. The influence of various reaction conditions including catalyst reusability on the alkylation reaction was studied, and the potential reasons to catalyst deactivation were discussed. The highest 2-LAB selectivity was more than 50% when 1-dodecene conversion was nearly 100%. Comparing with liquid or solid acid catalyst, ionic liquid catalysts have many advantages in perspectives concerning energy and environmental.

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“…Xin et al [29] synthesized alkylation catalysts [Rmim] + Al 2 Cl 6 X − ILs (R = butyl, octyl, and dodecyl; X = Cl, Br, and I), of which [BMIM]Al 2 Cl 6 Br had the best catalytic performance, with a conversion of 91.8% and a selectivity of 38.0% to 2-dodecylbenzene. In addition, a review wrote by Qiao et al [30] especially highlighted the applications of chloroaluminate ILs for alkylation of benzene with longchain olefins in petrochemical and detergent industry. Besides, Xiao and Malhotra [31] researched that the pyridinium-based ILs were suitable media for benzene alkylation with high reaction rate and high product conversion rate.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and performance of piperidinium‐based ionic liquids as catalyst for alkylation of p‐xylene with 1‐hexadecene

Zhou

Sheng

et al. 2021

Applied Organom Chemis

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Piperidinium-based ionic liquids (ILs) were synthesized under mild conditions by coordinating N-alkyl-N-methylpiperidinium bromide ([Pip 1,x ] Br) with anhydrous AlCl 3. The weak basicity of N-methylpiperidine had little impact on downstream problems from proton impurities and catalyst poisoning. The results of Fourier transform infrared (FT-IR), electrospray ionization mass spectrometry (ESI-MS), and nuclear magnetic resonance (27 Al NMR) confirmed that the active components in [Pip 1,x ]Br-2AlCl 3 (χ = 0.67) were [Al 3 Cl 9 Br] − and [Al 2 Cl 6 Br] −. Besides, the reaction performance of [Pip 1,8 ]Br-2AlCl 3 under different conditions was carried out by single-factor experiment and further confirmed by orthogonal experimental method. Among these reaction conditions, the optimal combination was the reaction temperature of 40 C, ILs/O molar ratio of 0.2:1, px/O molar ratio of 12:1, and the reaction time of 30 min. Furthermore, [Pip 1,8 ]Br-2AlCl 3 had excellent stability and can be recycled 14 times. It was the high-efficiency catalytic activity and prominent recyclability that made continuous industrial production possible.

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Benzene alkylation with long chain olefins catalyzed by ionic liquids: a review

Cited by 12 publications

References 32 publications

Acidic Ionic Liquids

Acidic Ionic Liquids

Durability enhanced ionic liquid catalyst for Friedel–Crafts reaction between benzene and 1-dodecene: insight into catalyst deactivation

Synthesis and performance of piperidinium‐based ionic liquids as catalyst for alkylation of p‐xylene with 1‐hexadecene

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