Kinetic Study of the Asymmetric Hydrogenation of Methyl Acetoacetate in the Presence of a Ruthenium Binaphthophosphepine Complex

Öchsner, Eva; Etzold, Bastian J. M.; Junge, Kathrin; Beller, Matthias; Wasserscheid, Peter

doi:10.1002/adsc.200800531

Cited by 11 publications

(5 citation statements)

References 26 publications

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“…When the enantioselective hydrogenation of b-ketoesters was run in a homogeneous solution made up of ionic liquids (IL) and methanol, 38 the reaction rate was higher than in pure IL's but the enantioselectivity was lower than that observed in plain methanol. 39 These differences have been attributed to the concurrent formation of ketal and hemiketal that is suppressed to a significant extent in the mixed system IL/methanol. Nature and performance of the catalysts heavily depend on the structure of the cationic part of IL.…”

Section: Formation Of C-h Bondsmentioning

confidence: 99%

BINEPINES: chiral binaphthalene-core monophosphepine ligands for multipurpose asymmetric catalysis

et al. 2011

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The atropisomeric structure of 4,5-dihydro-3H-dinaphtho[2,1-c;1',2'-e]phosphepine is the common axially chiral scaffold of a library of monophosphine ligands nicknamed BINEPINES that have shown a quite remarkable stereoselection efficiency in a broad variety of enantioselective reactions involving the formation of new C-H or C-C or C-X bonds. In this critical review the properties and scope of this type of chiral ligands are illustrated (70 references).

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Section: Formation Of C-h Bondsmentioning

confidence: 99%

BINEPINES: chiral binaphthalene-core monophosphepine ligands for multipurpose asymmetric catalysis

et al. 2011

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“…4g. The S- 12[BMIM][COO -] showed the maximal response which implies to maximized the deligninifcation yield and cellulosic sugars exposure as compared to other studied biomasses. This maximized response helped to examine the amount of cellulosic sugar exposed but it is possible through water addition as antisolvent in ILs than the temperature and time-duration.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, ILs-salts has an extensive solvating, in ammability, and high melting point characteristics which describe its green solvents nature and better solvent property than a wide range of naturally and synthetically synthesized organic solvents (9). Highlighted ILs chemical properties revealed that ILs act as green solvents due to unique characteristics and they are suitable for use in safer and cleaner industries and it may be considered as a better replaceable option of commonly utilized volatile organic solvents (10) in a number of biochemical processes (11,12). At present, around 10,000 known combinations of organic/inorganic anions and organic cations (13,14) are available and all are included in the class of ionic solvents, but relatively few of them are strictly known to have an ability to dissolve the biomass complex and rigid nature.…”

Section: Ionic Liquids Technologymentioning

confidence: 99%

Ionic Liquids, Loosened the Coconut Shell Rigidity to Boost up the Biofuels Productivity

Katiyar¹,

Srivastava²,

Kushwaha³

2021

Preprint

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Recently, a continuous rising awareness among human community to an environmental issue had changed the frame of current scenario and shifted a whole attention of research community towards the sustainable energy options & selecting the greener-solvents technology like Ionic-Liquids (ILs). An ionic-liquid technology known to augment the biorefineries pre-processing step mainly targeted to dissolute the complex and rigid structure of lignocellulosic biomass and promote to produce an economically valuable biofuels. 1-Butyl-3methylimidazolium acetate [BMIM][COO−] and 1-Butyl-3-methylimidazolium chloride [BMIM][Cl−] (ILs) were extensively studied in a current research study. Studied Ionic-liquids have a great capacity to fractionate the plant cellular components by employing the process of delignification, as it can be depicted through an evaluation of degree of cellulose-crystallinity index. Current study exploits an aqueous-ionic-liquid technology, where a combined reaction mixture of deionized-water, ionic-liquids (ILs) and biomass load-size were used in (1:10:1) ratio under vacuum. An observed result of the study determined the Total reducing sugar (TRS) content and residual lignin yield after employing the ILs pretreatment. It estimate yield of Total reducing sugar (46.6%) and residual lignin (36.25498%) in S-12 shell biomass pretreated with [BMIM][COO−] at 120°C for 2.5h under vacuum. Although, Taguchi approach significantly notified the affect of process parameters during the ILs pretreatment processing. In this context, water-content (wt%) had found the most dominant physical factor instead of, temperature and time-duration. This research study also finds the S-12[BMIM][COO−], an effective biomass candidate compared to other studied biomasses to achieve the high biofuel yield in a cost-effective manner.

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“…The reaction course expressed in the form of a formal reaction scheme (Scheme 1) has been reported repeatedly [34,37,38]. It comprises a series of steps and formation of a series reaction intermediates.…”

Section: Resultsmentioning

confidence: 99%

“…The general selectivity parameter S to MHB reflected formation of acetals in the presence of methanol as described previously [34,37].…”

Section: Hydrogenation Reactionsmentioning

confidence: 99%

Notes on the Asymmetric Hydrogenation of Methyl Acetoacetate in Neoteric Solvents

Floris

Klusoň

Muldoon³

2009

Catal Lett

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Asymmetric hydrogenation of methyl acetoacetate to methyl (R)-3-hydroxybutyrate by [(R)-RuCl(binap)(p-cymen)]Cl has been studied in methanol-ionic liquid and methanol-dense CO 2 solvent systems. The ionic pairs triethylhexylammonium and 1-methylimidazolium with bis(trifluoromethane sulfonyl) imide and hexafluorophosphates were used. The role of ionic pairs on the kinetic parameters and (enantio)selectivity has been demonstrated. Although the CO 2 expanded methanol system suffered from a reduction in both reaction rate and product selectivity, this changed in the presence of water. The high selectivity of the optimized methanol-CO 2 -water-halide system was designed as a consequence of observed additive effects.

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Kinetic Study of the Asymmetric Hydrogenation of Methyl Acetoacetate in the Presence of a Ruthenium Binaphthophosphepine Complex

Cited by 11 publications

References 26 publications

BINEPINES: chiral binaphthalene-core monophosphepine ligands for multipurpose asymmetric catalysis

BINEPINES: chiral binaphthalene-core monophosphepine ligands for multipurpose asymmetric catalysis

Ionic Liquids, Loosened the Coconut Shell Rigidity to Boost up the Biofuels Productivity

Notes on the Asymmetric Hydrogenation of Methyl Acetoacetate in Neoteric Solvents

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