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Catalysts
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Organocatalysis in Ionic Liquids
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Organocatalysis in Ionic Liquids

A special issue of Catalysts (ISSN 2073-4344). This special issue belongs to the section "Catalytic Materials".

Deadline for manuscript submissions: closed (31 January 2018) | Viewed by 34291

Special Issue Editor

Prof. Dr. Sandrine Bouquillon

E-Mail Website
Guest Editor
Institute of Molecular Chemistry of Reims, UMR CNRS 7312, Université Reims Champagne, Ardenne, 51687 Reims, France
Interests: green chemistry; sugar-based and acid-based surfactants; glyco-and glycerodendrimers; bio-based ionic liquids; synthesis; catalysis
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

This Special Issue is dedicated to organocatalytic processes, which could be realized in ionic liquids medium. This Special Issue will contribute to the field by showing the role of such solvents (or co-solvents) in organocatalysis, especially concerning the selectivity, the enantioselectivity, and the possibility of recycling catalytic species. Special attention will be given to green processes or processes involving bio-sourced ionic liquids and/or substrates.

Prof. Dr. Sandrine Bouquillon
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Catalysts is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • ionic liquids
  • organocatalysis
  • recycling
  • selectivity
  • enantioselectivity
  • green processes
  • green ionic liquids

Published Papers (7 papers)

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Research

3765 KiB  
Article
Stability, Deactivation, and Regeneration of Chloroaluminate Ionic Liquid as Catalyst for Industrial C4 Alkylation
by Xiang Li, Jie Zhang, Chongpin Huang, Biaohua Chen, Jianwei Li and Zhigang Lei
Catalysts 2018, 8(1), 7; https://doi.org/10.3390/catal8010007 - 29 Dec 2017
Cited by 14 | Viewed by 4588
Abstract
Alkylation of isobutane and 2-butene was carried out in a continuous unit using triethylamine hydrochloride (Et3NHCl)-aluminum chloride (AlCl3) ionic liquid (IL) as catalyst. The effects of impurities such as water, methanol, and diethyl ether on the stability of the [...] Read more.
Alkylation of isobutane and 2-butene was carried out in a continuous unit using triethylamine hydrochloride (Et3NHCl)-aluminum chloride (AlCl3) ionic liquid (IL) as catalyst. The effects of impurities such as water, methanol, and diethyl ether on the stability of the catalytic properties and deactivation of the ionic liquid were studied in the continuous alkylation. In the Et3NHCl-2AlCl3 ionic liquid, only one half of the aluminum chloride could act as the active site. With a molar ratio of 1:1, the active aluminum chloride in the ionic liquid was deactivated by water by reaction or by diethyl ether through complexation while the complexation of aluminum chloride with two molecular proportions of methanol inactivated the active aluminum chloride in the ionic liquid. The deactivation of chloroaluminate ionic liquid was observed when the active aluminum chloride, i.e., one half of the total aluminum chloride in the ionic liquid, was consumed completely. The regeneration of the deactivated ionic liquid was also investigated and the catalytic activity could be recovered by means of replenishment with fresh aluminum chloride. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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14872 KiB  
Article
Facile One-Pot Synthesis of Amidoalkyl Naphthols and Benzopyrans Using Magnetic Nanoparticle-Supported Acidic Ionic Liquid as a Highly Efficient and Reusable Catalyst
by Qiang Zhang, Yin-Hong Gao, Shan-Lin Qin and Huai-Xin Wei
Catalysts 2017, 7(11), 351; https://doi.org/10.3390/catal7110351 - 21 Nov 2017
Cited by 36 | Viewed by 6257
Abstract
An efficient and eco-friendly procedure for the synthesis of 1-amidoalkyl-2-naphthol and tetrahydrobenzo[b]pyran derivatives has been developed through a one-pot three-component condensation of aldehydes with 2-naphthol and amides, or with malononitrile and dimedone in the presence of magnetic nanoparticle supported acidic ionic [...] Read more.
An efficient and eco-friendly procedure for the synthesis of 1-amidoalkyl-2-naphthol and tetrahydrobenzo[b]pyran derivatives has been developed through a one-pot three-component condensation of aldehydes with 2-naphthol and amides, or with malononitrile and dimedone in the presence of magnetic nanoparticle supported acidic ionic liquid (AIL@MNP) as a novel heterogeneous catalyst under solvent-free conditions. This new procedure offers several advantages such as short reaction time, excellent yields, operational simplicity and without any tedious work-up for catalyst recovery or product purification. Moreover, the catalyst could be simply separated by an external magnet and reused six times without significant loss of catalytic activity. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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Graphical abstract

555 KiB  
Article
PEG1000-Based Dicationic Acidic Ionic Liquid/Solvent-Free Conditions: An Efficient Catalytic System for the Synthesis of Bis(Indolyl)methanes
by Yi-Ming Ren, Mao-Dong Xu and Xiong Wang
Catalysts 2017, 7(10), 300; https://doi.org/10.3390/catal7100300 - 11 Oct 2017
Cited by 14 | Viewed by 3641
Abstract
An efficient procedure has been researched for the solvent-free synthesis of bis(indolyl)methanes via a one-pot reaction of indoles and aldehydes or ketones promoted by PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL). The catalyst PEG1000-DAIL could be reused seven [...] Read more.
An efficient procedure has been researched for the solvent-free synthesis of bis(indolyl)methanes via a one-pot reaction of indoles and aldehydes or ketones promoted by PEG1000-based dicationic acidic ionic liquid (PEG1000-DAIL). The catalyst PEG1000-DAIL could be reused seven times with excellent results. Furthermore, through this method, a highly chemoselective reaction of benzaldehyde and acetophenone with indole could be achieved. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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Graphical abstract

1350 KiB  
Article
Conversion of Carbohydrates into Platform Chemicals Catalyzed by Alkaline Ionic Liquids
by Xiaojia Du, Jie Zhang, Yuehai Wang and Yongshui Qu
Catalysts 2017, 7(9), 245; https://doi.org/10.3390/catal7090245 - 23 Aug 2017
Cited by 9 | Viewed by 4087
Abstract
A series of alkaline ionic liquids (ILs) including 1-butyl-3-methylimidazolium benzoate ([BMIM]PHCOO), 1-butyl-3-methylimidazolium carbonate ([BMIM]2CO3), 1-butyl-3-methylimidazolium acetate ([BMIM]OAc), 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), ethanolamine tetrafluoroborate ([MEA]BF4), and 1,1,3,3-tetramethylguanidine (TMG)-based ILs, etc., were synthesized and utilized as catalysts for the conversion [...] Read more.
A series of alkaline ionic liquids (ILs) including 1-butyl-3-methylimidazolium benzoate ([BMIM]PHCOO), 1-butyl-3-methylimidazolium carbonate ([BMIM]2CO3), 1-butyl-3-methylimidazolium acetate ([BMIM]OAc), 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), ethanolamine tetrafluoroborate ([MEA]BF4), and 1,1,3,3-tetramethylguanidine (TMG)-based ILs, etc., were synthesized and utilized as catalysts for the conversion of carbohydrates into 5-HMF. 1,1,3,3-tetramethylguanidine tetrafluoroborate ([TMG]BF4) was confirmed to exhibit excellent catalytic activity, and was much cheaper than other ILs such as 1-butyl-3-methylimidazolium chloride ([BMIM]Cl) for use as a solvent in the conversion of C6 carbohydrates into 5-HMF. The 5-HMF yields from fructose, glucose, cellobiose, and microcrystalline cellulose (MCC) were 74.19%, 27.33%, 20.20%, and 17.73%, respectively. In addition, the possible pathway of carbohydrates (MCC, cellobiose, glucose, etc.) conversion into 5-HMF with [TMG]BF4 as a catalyst was speculated, and the conversion of glucose into 5-HMF was determined to likely be the committed step in the transformation of MCC catalyzed by [TMG]BF4. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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879 KiB  
Communication
Direct Conversion of Propylene Oxide to 3-Hydroxy Butyric Acid Using a Cobalt Carbonyl Ionic Liquid Catalyst
by Senkuttuvan Rajendiran, Gyoosoon Park and Sungho Yoon
Catalysts 2017, 7(8), 228; https://doi.org/10.3390/catal7080228 - 30 Jul 2017
Cited by 10 | Viewed by 4744
Abstract
The reported catalytic system demonstrates the possibility of efficient mass production of 3-hydroxybutyric acid (3-HBA) from inexpensive raw materials. The direct coupling of propylene oxide, water, and CO was catalyzed by 1-butyl-3-methylimidazolium cobalt tetracarbonyl ([Bmim][Co(CO)4]) ionic liquid to form 3-HBA with [...] Read more.
The reported catalytic system demonstrates the possibility of efficient mass production of 3-hydroxybutyric acid (3-HBA) from inexpensive raw materials. The direct coupling of propylene oxide, water, and CO was catalyzed by 1-butyl-3-methylimidazolium cobalt tetracarbonyl ([Bmim][Co(CO)4]) ionic liquid to form 3-HBA with >99% conversion (49% selectivity) under mild conditions. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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Graphical abstract

1285 KiB  
Communication
Lipase-Catalyzed Synthesis of Indolyl 4H-Chromenes via a Multicomponent Reaction in Ionic Liquid
by Weian Zhang, Ziyuan Zhao, Zhi Wang, Chao Guo, Chunyu Wang, Rui Zhao and Lei Wang
Catalysts 2017, 7(6), 185; https://doi.org/10.3390/catal7060185 - 08 Jun 2017
Cited by 24 | Viewed by 4667
Abstract
Synthesis of indolyl 4H-chromenes via a three-component reaction catalyzed by lipase in ionic liquidsis reported here for the first time. High yields (77–98%) were obtained when Mucor miehei lipase was used as the catalyst in [EMIM][BF4]. Furthermore, [EMIM][BF4] exhibited [...] Read more.
Synthesis of indolyl 4H-chromenes via a three-component reaction catalyzed by lipase in ionic liquidsis reported here for the first time. High yields (77–98%) were obtained when Mucor miehei lipase was used as the catalyst in [EMIM][BF4]. Furthermore, [EMIM][BF4] exhibited good reusability in this enzymatic reaction. This study affords a new example of lipase catalytic promiscuity and broadens the application range of ionic liquid in biocatalysis. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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Graphical abstract

3290 KiB  
Article
Caprolactam-Based Brønsted Acidic Ionic Liquids for Biodiesel Production from Jatropha Oil
by Hui Luo, Heng Yin, Rui Wang, Weiyu Fan and Guozhi Nan
Catalysts 2017, 7(4), 102; https://doi.org/10.3390/catal7040102 - 27 Mar 2017
Cited by 10 | Viewed by 5579
Abstract
Caprolactam-based ionic liquids show many advantages, such as the lower toxicity, lower cost, and a simple preparation process. In this work, caprolactam-based ionic liquids were prepared and adopted as catalysts for the transesterification of Jatropha oil with methanol. The results demonstrated that the [...] Read more.
Caprolactam-based ionic liquids show many advantages, such as the lower toxicity, lower cost, and a simple preparation process. In this work, caprolactam-based ionic liquids were prepared and adopted as catalysts for the transesterification of Jatropha oil with methanol. The results demonstrated that the SO3H-functional caprolactam‐based ionic liquids have higher catalytic activity than those of the caprolactam-based ionic liquids without sulfonic group or the SO3H-functional pyridine-based ionic liquids, attributed to their stronger Brønsted acidity. By optimizing the reaction parameter, the biodiesel yield catalyzed by 1-(4-sulfonic group) butylcaprolactamium hydrogen sulfate ([HSO3-bCPL][HSO4]) could reach above 95% at 140 °C for 3 h. Furthermore, the ionic liquid had a good reusability. Full article
(This article belongs to the Special Issue Organocatalysis in Ionic Liquids)
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