- Recyclable supported Br?nsted acidic ionic liquid catalysts with non-aromatic cations for the oligomerization of isobutene under mild conditions
-
Br?nsted acidic ionic liquids with different type of cations (pyridinium, morpholinium, pyrrolidinium, imidazolium), N-sulfoalkyl chain length and different anions (triflate, hydrogensulfate and tetrafluoroborate) were prepared and immobilised on silica by adsorption. The ionic liquids were characterised by NMR and IR. Surface properties and Br?nsted/Lewis acidity of the supported catalysts were also determined. Their catalytic activity and recyclability were compared in the oligomerisation of isobutene to obtain products that can be used as jet fuel blending components after hydrogenation. The results proved that imidazolium ionic liquids can be replaced by less toxic non-aromatic versions without any loss in their activity and stability. By the introduction of shorter sulfoalkyl chain into the cation, excellent results could be obtained even under milder conditions (lower temperature and shorter reaction time). Catalytic activity was shown to correlate to the Br?nsted acidity of the catalyst.
- Füty?, Júlia,Fehér, Csaba,Hancsók, Jen?,Ispán, Dávid,Juzsakova, Tatjána,Skoda-F?ldes, Rita,Szegedi, ágnes
-
-
- Selective monoalkylation of hydroquinone in the presence of SO3H-functionalized ionic liquids as catalysts
-
A process aiming at O-alkylation of hydroquinone (HQ), where ionic liquids (ILs) act as catalyst is objectively described. Five SO3H-functionalized ILs having different cations were prepared and characterized by NMR and FTIR techniques. The acidity and thermal stability of ILs were determined by Hammett function and thermogravimetric analysis (TGA), respectively. The catalytic activity of these ILs were tested for O-alkylation of HQ with methanol in 4-methoxyphenol (4MP) in the presence of small amount of benzoquinone (BQ). The effect of reaction parameters such as temperature, time, catalyst loading and substrate concentration on the conversion of HQ and product distribution was examined and optimized to maximize the yield of 4MP using 1,3-disulfonic acid imidazolium hydrogen sulfate (IL2) catalyst. Maximum yield of desired product 4MP 93.79percent was obtained at 338?K temperature, 5.45 × 10–2?mol HQ, 8.33 × 10–3?mol BQ, and 10.37?molpercent catalyst loading in 120?min reaction time. Single-product formation was observed up to 338?K temperature but higher temperature (above 338?K) and longer reaction time resulted in the formation of 2,4-dimethoxyphenol (24DMP) as a by-product. Catalyst recyclability was also established up to the fifth run which showed no declination in its activity.
- Bhongale, Priyanka V.,Joshi, Sunil S.,Mali, Nilesh A.
-
p. 4461 - 4471
(2020/07/13)
-
- Method for preparing maleate by catalyzing maleic anhydride with ionic liquid
-
The invention discloses a method for preparing maleate by catalyzing maleic anhydride with ionic liquid. The preparation method is characterized by comprising the following steps: mixing ionic liquidwith maleic anhydride and fatty alcohol, carrying out heating to 80-140 DEG C, and performing a reaction for 0.5-4 h to obtain maleate, wherein the usage amount of the ionic liquid accounts for 0.1-10% by mol of the maleic anhydride, and a molar ratio of fatty alcohol to maleic anhydride is 2-12. A high-added-value chemical with the completely-esterified maleate as a main product is prepared in the invention. The method is simple in process, mild in conditions, friendly to environment and high in double esterification degree; and the ionic liquid is high in activity, not prone to inactivationand capable of being cyclically used.
- -
-
Paragraph 0031-0035; 0041-0043; 0049-0051
(2020/02/29)
-
- A non-metal route to realize the bio-based polyester of poly(hexylene succinate): preparation conditions, side-reactions and mechanism in sulfonic acid-functionalized Br?nsted acidic ionic liquids
-
A biodegradable linear bio-based polyester of poly(hexylene succinate) was effectively prepared in non-metal sulfonic acid-functionalized Br?nsted acidic ionic liquids (SFBAILs) as both the catalyst and the polymerization medium, and the processes of polycondensation and post-polycondensation in SFBAILs were also investigated. In addition, the side reactions which were detrimental to the growth ofMwof poly(hexylene succinate) were evaluated and the synthesis mechanism of poly(hexylene succinate) catalyzed by SFBAILs was discussed with the help of DFT calculations. The result shows that both the imidazole ring and the sulfonic group on cations of SFBAILs play an important role in the catalytic process.
- Huang, Liyan,Li, Jun,Liu, Zhengping,Tan, Hongwei,Wei, Chenyang
-
p. 35381 - 35388
(2020/10/19)
-
- A two-phase system for the clean and high yield synthesis of furylmethane derivatives over -SO3H functionalized ionic liquids
-
A new and effective unique two-phase reaction system is investigated for the high yield production of tri(furyl)methane from furfural and furan. This strategy includes the use of an acidic aqueous phase (water + -SO3H functionalized IL) and furan phase, which significantly suppresses polymer formation, thereby increasing the yield of tri(furyl)methane. Furan serves as a reactant as well as an extraction solvent for the recovery of the condensation products. For comparison, different -SO3H functionalized ionic liquids are prepared and their performances evaluated for the condensation of furan and furfural. The ionic liquids with alkyl chain linkers are found to be more effective and acidic than those with imidazolium linked N-sulfonic acids. In addition, an increase in carbon chain length between imidazole/tri-ethylamine/pyridine and -SO3H, increases the catalytic activity of the respective ionic liquids. Among the several prepared ionic liquids, the strongly acidic imidazolium based butylsulfonic acid 6 shows the best activity with a maximum condensation product yield of 84%. This strategy offers a significantly high yield of the condensation products of furan and furfural compared to the traditional mineral acid route. The activity and stability of the -SO3H functionalized 6 is confirmed from seven successful recycles, in which there is no reduction in its activity. Finally, this new strategy is successfully extended for the condensation of furan derivatives (e.g. furan and 2-methylfuran) with several different aldehydes, ketones and alcohols.
- Shinde,Rode
-
p. 4804 - 4810
(2017/10/19)
-
- Ir/C and Brφnsted acid functionalized ionic liquids an efficient catalytic system for hydrogenation of nitrobenzene to: P -aminophenol
-
In this study, we found that the phenylhydroxylamine intermediate could desorb more easily from an Ir surface than from a Pt surface, which is beneficial for inhibiting the over-hydrogenation of phenylhydroxylamine to aniline. On the other hand, the Brφnsted acid functionalized ionic liquids with sulfonic acid and bisulfate anions were acidic enough to catalyze the Bamberger rearrangement to form p-aminophenol from phenylhydroxylamine. On this basis, a new catalytic system constructed by Ir/C and Brφnsted acid functionalized ionic liquid was applied, for the first time, to the one-pot hydrogenation of nitrobenzene to p-aminophenol. Our results indicate that the PAP selectivity of Ir/C and [SO3H-bmim][HSO4] Brφnsted functionalized ionic liquid was far more than that of the traditional Pt/C and sulfuric acid catalyst system. Furthermore, the dually functionalized ionic liquid ([HSO3-b-N-Bu3][HSO4]) can be used simultaneously as an acid catalyst and also as a surfactant, due to its higher lipophilicity. Therefore, our new catalytic system has unique advantages in the hydrogenation of nitrobenzene to p-aminophenol.
- Wang, Hong,Jiang, Taotao,Ma, Lei,Wang, Hanbing,Xu, Xiaoliang,Lu, Chunshan,Li, Xiaonian
-
p. 31663 - 31670
(2017/07/07)
-
- Green synthesis of dipyrromethanes in aqueous media catalyzed by SO3H-functionalized ionic liquid
-
A mild, efficient and metal-free method was described for the green synthesis of dipyrromethanes from aldehydes and unsubstituted pyrrole catalyzed by SO3H-functionalized ionic liquids (SO3H-ILs) in aqueous media at room temperature. Notably, SO3H-ILs, 1-butylsulfonic-3-methylimidazolium hydrogen sulfate ([bsmim][HSO4]) was the most efficient catalyst for moderate to good yields of the corresponding desired products.
- Senapak,Saeeng,Jaratjaroonphong,Kasemsuk,Sirion
-
p. 1302 - 1310
(2016/02/03)
-
- Comprising zwitterionic and/or acid-functionalized ion liquid palladium catalyst system
-
The present invention concerns a catalyst system in particular a catalyst system comprising Palladium (Pd), a zwitterion and/or an acid-functionalized ionic liquid, and one or more phosphine ligands, wherein the Pd catalyst can be provided by a complex precursor, such as Pd(CH3COO)2, PdCI2, Pd(CH3COCHCOCH3), Pd (CF3COO)2, Pd(PPh3)4 or Pd2(dibenzylideneacetone)3. Such catalyst systems can be used for e.g. alkoxycarbonylation reactions, carboxylation reactions, and/or in a co-polymerization reaction, e.g. in the production of methyl propionate and/or propanoic acid, optionally in processes forming methyl methacrylate and/or methacrylic acid. Catalyst systems according to the invention are suitable for reactions forming separable product and catalyst phases and supported ionic liquid phase SILP applications.
- -
-
-
- Bronsted acid ionic liquid catalyzed formation of pyruvaldehyde dimethylacetal from triose sugars
-
A series of sulfonic acid functionalized ionic liquids (SO 3H-ILs) have been synthesized, characterized and investigated as catalysts for the conversion of the triose sugars, 1,3-dihydroxyacetone (DHA) and glyceraldehyde (GLA), to pyruvaldehyde dimethylacetal (PADA) in methanol. Depending on the reaction conditions and the applied SO3H-ILs a good yield of up to 52% of PADA was obtained. Under identical reaction conditions the derivative of PADA, 1,1,2,2-tetramethoxy propane (TMP), could be obtained in yields up to 49% using another SO3H-IL.
- Saravanamurugan, Shunmugavel,Riisager, Anders
-
-
- Kinetics and quantum chemical study for cyclotrimerization of propanal catalyzed by Br?nsted acidic ionic liquids
-
Several Br?nsted acidic ionic liquids (BAILs) were synthesized and used as catalysts for the cyclotrimerization of propanal. The acidity of different BAILs was explored and a preliminarily study of the relationship between catalytic activity and acidity was performed. The kinetics for the BAILs-catalyzed cyclotrimerization of propanal was studied systemically to determine the kinetic model and the kinetic parameters by taking [BSTMG][HSO4] as the representative catalyst. The effects of various parameters such as catalyst loading, reaction temperature on the kinetics were examined in detail. Besides, the structures of three representative BAILs and the interactions between propanal molecule and ionic pairs of BAILs were studied by means of quantum chemistry calculations.
- Wu, Li,Li, Zhen,Wang, Fang,Lei, Min,Chen, Jing
-
-
- Highly efficient synthesis of N-confused meso-tetraspirocyclohexyl calix[4]pyrrole using Bronsted acidic ionic liquids as catalysts
-
An efficient, green and novel protocol is described for high yield synthesis of N-confused meso-tetraspirocyclohexyl calix[4]pyrrole. In aqueous solution, the condensation of pyrrole and cyclohexanone in the presence of Bronsted acidic ionic liquid catalysts afforded N-confused calix[4]pyrrole in up to 62.5% yield which represents a ~threefold yield improvement over existing protocol and makes significant quantity of N-confused calix[4]pyrrole readily available.
- Garg, Bhaskar,Ling, Yong-Chien
-
supporting information
p. 5674 - 5677
(2012/11/07)
-
- PALLADIUM CATALYST SYSTEM COMPRISING ZWITTERION AND/OR ACID-FUNCTIONALYZED IONIC LIQUID
-
The present invention concerns a catalyst system in particular a catalyst system comprising Palladium (Pd), a zwitterion and/or an acid-functionalized ionic liquid, and one or more phosphine ligands, wherein the Pd catalyst can be provided by a complex precursor, such as Pd(CH3COO)2, PdCl2, Pd(CH3COCHCOCH3), Pd(CF3COO)2, Pd(PPh3)4 or Pd2(dibenzylideneacetone)3. Such catalyst systems can be used for e.g. alkoxycarbonylation reactions, carboxylation reactions, and/or in a co-polymerization reaction, e.g. in the production of methyl propionate and/or propanoic acid, optionally in processes forming methyl methacrylate and/or methacrylic acid. Catalyst systems according to the invention are suitable for reactions forming separable product and catalyst phases and supported ionic liquid phase SILP applications.
- -
-
Page/Page column 9
(2011/04/18)
-
- Bronsted acidic ionic liquids as efficient catalysts for clean synthesis of carbamatoalkyl naphthols
-
Under mild conditions and without any additional organic solvent, synthesis of carbamatoalkyl naphthols could be carried out in the present of two halogen-free Bronsted acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate and N-(4-sulfonic acid)butylpyridinium hydrogen sulfate. A widerange of aromatic aldehydes easily undergo condensation with β-naphthol and methyl or benzyl carbamate to afford the desired products of good purity in excellent yields. The present methodology offers several advantages such as a simple procedure with an easy work-up, short reaction times, and excellent yields. The catalysts could be recycled and reused for several times without substantial reduction in their catalytic activities. Copyright
- Tavakoli-Hoseini, Niloofar,Heravi, Majid M.,Bamoharram, Fatemeh F.,Davoodnia, Abolghasem
-
experimental part
p. 787 - 792
(2011/12/22)
-
- Bronsted acidic ionic liquids: New, efficient, and green promoter system for the synthesis of 4(3H)-quinazolinones
-
A simple, inexpensive, and efficient new synthesis of 4(3H)-quinazolinones from the reaction of 2-aminobenzamide with aroyl chlorides in the presence of two new halogen-free Brnsted acidic ionic liquids, 3-methyl-1-(4-sulfonic acid)butylimidazolium hydrogen sulfate [(CH2)4SO 3HMIM][HSO4] and 1-(4-sulfonic acid) butylpyridinium hydrogen sulfate [(CH2)4SO3HPY][HSO4], green and reusable catalysts, with excellent product yields under solvent-free conditions is reported. The products could be separated simply from the catalyst, and the catalyst could be recycled without noticeably decreasing the catalytic activity.
- Heravi, Majid M.,Tavakoli-Hoseini, Niloofar,Bamoharram, Fatemeh F.
-
experimental part
p. 707 - 714
(2011/04/12)
-
- Application of pyridinium ionic liquid as a recyclable catalyst for acid-catalyzed transesterification of jatropha oil
-
A series of pyridinium ionic liquids were synthesized and characterized. Acid-catalyzed transesterifications of Jatropha oil were carried out with these ionic liquids under mild reaction conditions. [BSPy]CF3SO3 showed the best catal
- Li, Kai-Xin,Chen, Li,Yan, Zong-Cheng,Wang, Hong-Lin
-
experimental part
p. 151 - 156
(2010/12/25)
-
- Alkylation of p-cresol with tert-butyl alcohol using benign Bronsted acidic ionic liquid catalyst
-
Novel and environmentally benign Bronsted acidic ionic liquids with SO3-H functionality were prepared using N-methyl imidazole, pyridine, triethylamine and 1,4-butanesultone as the source chemicals. The prepared ionic liquid catalysts were characterized by NMR and their catalytic activity in tert-butylation of p-cresol with tert-butyl alcohol (TBA) was investigated. The effects of reaction time, reaction temperature, reactant mole ratio and the recyclability of the catalysts on the conversion of p-cresol and selectivity to 2-tert-butyl-p-cresol (TBC) and 2,6-di-tert-butyl-p-cresol (DTBC) called butylated hydroxytoluene (BHT) were investigated. Lower alcohol to p-cresol mole ratios, lower ionic liquid to p-cresol ratio and temperature as low as 70 °C gave 80% conversion of p-cresol. The catalyst activity was found to be almost completely retained even after 5 recycles. Extended Arrhenius equation was used to calculate the rate constants for this reaction.
- Kondamudi, Kishore,Elavarasan, Pandian,Dyson, Paul J.,Upadhyayula, Sreedevi
-
experimental part
p. 34 - 41
(2010/08/19)
-
- METHOD OF MAKING A LACTAM IN AN IONIC LIQUID
-
The invention relates to a method of contacting a cyclic oxime with a Br?nsted acidic ionic liquid having a sulfur atom in the anionic portion and/or the cationic portion further comprising mechanical stirring, microwave irradiation and/or ultrasonic treatment.
- -
-
Page/Page column 10
(2009/01/20)
-