- Bifunctional ionic liquid, preparation method thereof and application of bifunctional ionic liquid in catalytic synthesis of bisphenol compounds
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The invention discloses a bifunctional ionic liquid, a preparation method thereof and application of the bifunctional ionic liquid in catalytic synthesis of bisphenol compounds, and belongs to the field of application of ionic liquid catalysts. The bifunctional ionic liquid is composed of heterocyclic quaternary ammonium cations containing sulfonic groups and sulfydryl and organic strong acid anions containing or not containing sulfydryl. The bifunctional ionic liquid has the functions of strong protonic acid and a -SH-containing compound, is used for catalytic synthesis of diphenolic acid, bisphenol A, bisphenol fluorene and the like, and has the characteristics of high reaction rate, high target product yield and good selectivity. The bifunctional ionic liquid is a green catalyst which is stable in performance and can be recycled, and compared with a protonic acid and sulfhydryl compound composite catalyst used in a traditional production process, the production process is simplified, equipment corrosion is reduced, and the production cost is reduced.
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Paragraph 0060-0061
(2021/08/14)
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- Kinetics of phosphotungstic acid-catalyzed condensation of levulinic acid with phenol to diphenolic acid: Temperature-controlled regioselectivity
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Diphenolic acid (DPA) is a renewable compound to produce polycarbonates and epoxy resins. Diphenolic acid is produced by acid-catalyzed condensation of levulinic acid with phenol to form monophenolic acid. Subsequently, monophenolic acid undergoes condensation with phenol to form two DPA isomers, ortho-diphenolic acid (o,p′-DPA) and para-diphenolic acid (p,p′-DPA). Here we describe a kinetic analysis of solvent-free levulinic acid-phenol condensation catalyzed by phosphotungstic acid at temperatures between 70 and 140°C. The reaction appeared to be pseudo-first-order with respect to levulinic acid when the levulinic acid:phenol molar ratio was four or higher. We determined the kinetic parameters (reaction rate constants, pre-exponential factors, and activation energies) by fitting experimental results to simulated data. Although the activation energies of o,p′-DPA, and p,p′-DPA formation were higher than their corresponding reverse reactions, the kinetic analyses revealed that a steric effect controls the reaction products. Our findings demonstrated a simple temperature-controlled strategy to achieve a p,p′:o,p′ DPA molar ratio of 28.3 with 87% conversion and 98% selectivity to total DPA. This work provides a potential production route for p,p′-DPA from biomass.
- Evrard, Clint N.,Hossain, Md Anwar,Rahaman, Mohammad Shahinur,Sathitsuksanoh, Noppadon,Thompson, Lee M.,Tulaphol, Sarttrawut
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- Bronsted acidic ionic liquids catalyze the high-yield production of diphenolic acid/esters from renewable levulinic acid
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The high-yielding synthesis of diphenolic acid (DPA) using Bronsted acidic ionic liquids (BAILs) has been demonstrated in this study. Importantly, p,p′-DPA was obtained as the preferential product over o,p′-DPA with an isomer ratio over 100. Moreover, diphenolic esters were also prepared in high yield through a one-pot method.
- Liu, Hai-Feng,Zeng, Fan-Xin,Deng, Li,Liao, Bing,Pang, Hao,Guo, Qing-Xiang
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supporting information
p. 81 - 84
(2013/02/26)
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- Thiol-promoted catalytic synthesis of diphenolic acid with sulfonated hyperbranched poly(arylene oxindole)s
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Acid-catalyzed condensation of levulinic acid and phenol into high yields of diphenolic acid (>50%) is possible with a combination of sulfonated hyperbranched polymers and thiol promotors, either added as a physical mixture or bound to the polymer by ion-pairing.
- Van De Vyver, Stijn,Geboers, Jan,Helsen, Sasja,Yu, Feng,Thomas, Joice,Smet, Mario,Dehaen, Wim,Sels, Bert F.
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scheme or table
p. 3497 - 3499
(2012/06/18)
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- Symmetrical bis(heteroarylmethoxyphenyl)alkylcarboxylic acids as inhibitors of leukotriene biosynthesis
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Symmetrical bis(quinolylmethoxyphenyl)alkylcarboxylic acids were investigated as inhibitors of leukotriene biosynthesis and 4,4-bis(4-(2-quinolylmethoxy)phenyl)pentanoic acid sodium salt (47·Na) met our design parameters for a drug candidate (ABT-080). This compound was readily synthesized in three steps from commercially available diphenolic acid. Against intact human neutrophils, 47·Na inhibited ionophore-stimulated LTB4 formation with an IC50 = 20 nM. In zymosan-stimulated mouse peritoneal macrophages producing both LTC4 and PGE2, 47·Na showed 9000-fold selectivity for inhibition of LTC4 (IC50 = 0.16 nM) over PGE2 (IC50 = 1500 nM). Preliminary pharmacokinetic evaluation in rat and cynomolgus monkey demonstrated good oral bioavailability and elimination half-lives of 9 and 5 h, respectively. Pharmacological evaluation of leukotriene inhibition with oral dosing was demonstrated in a rat pleural inflammation model (ED50 = 3 mg/kg) and a rat peritoneal passive anaphylaxis model (LTB4, ED50 = 2.5 mg/kg; LTE4, ED50 = 1.0 mg/kg). In a model of airway constriction induced by antigen challenge in actively sensitized guinea pigs, 47·Na dosed orally blocked bronchoconstriction with an ED50 = 0.4 mg/kg, the most potent activity we have observed for any leukotriene inhibitor in this model. The mode of inhibitory action of 47·Na occurs at the stage of 5-lipoxygenase biosynthesis as it blocks both leukotriene pathways leading to LTB4 and LTC4 but not PGH2 biosynthesis. However, 47·Na does not inhibit 5-lipoxygenase catalysis in a broken cell enzyme assay; therefore it is likely that 47·Na acts as a FLAP inhibitor.
- Kolasa,Gunn,Bhatia,Basha,Craig,Stewart,Bouska,Harris,Hulkower,Malo,Bell,Carter,Brooks
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p. 3322 - 3334
(2007/10/03)
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- A Versatile New Method for Structure Determination in Hyperbranched Macromolecules
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A novel degradative procedure for the determination of the degree of branching in hyperbranched macromolecules is presented, and its versatility and scope are demonstrated with the synthesis and characterization of hyperbranched polyesters based on 4,4-bis(4'-hydroxyphenyl)pentanoic acid.
- Kambouris, Peter,Hawker, Craig J.
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p. 2717 - 2722
(2007/10/02)
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- Lowering lipid and sugar levels in the blood with a bis(4-hydroxyphenyl)alkanoic acid or ester thereof
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Pharmaceutical compositions acting on the metabolism which contain as active substance bis(4-hydroxy-phenyl)alkanoic acids corresponding to the formulae I and II STR1 wherein R1 and R2 wich may be identical or different, each stands for a hydrogen or halogen atom or an alkyl group having 1 to 4 carbon atoms, R3 stands for a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R4 stands for hydroxy, alkoxy having 1 to 18 carbon atoms, phenyl-alkoxy having 1 to 4 alkyl carbon atoms, cycloalkoxy having 5 to 8 carbon atoms or a group of the formula STR2 in which Z and Z', which may be identical or different, each stands for hydrogen, alkyl of 1 to 18 carbon atoms, phenyl or cycloalkyl of 5 to 8 carbon atoms, or both together with the nitrogen atom may form a heterocyclic ring, R6 stands for an alkylene radical having 2 to 12 atoms and n stands for zero or an integer of 1 to 6, and process for preparing them.
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