Ueber den der Benzoësäure entsprechenden Alkohol

Cannizzaro, S.

doi:10.1002/jlac.18530880114

Cited by 188 publications

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“…This is also named after its discoverer S. Cannizzaro (123) in 1853. Classically, this reaction includes the use of caustic alkali, and one molecule of aldehyde is oxidized to acid and the other is reduced to corresponding alcohol (124Á127) (Scheme 14).…”

Section: Cannizzaro Reactionmentioning

confidence: 95%

Recent advances in ionic liquids: green unconventional solvents of this century: part II

Sandhu

2011

Green Chemistry Letters and Reviews

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Section: Cannizzaro Reactionmentioning

confidence: 95%

Recent advances in ionic liquids: green unconventional solvents of this century: part II

Sandhu

2011

Green Chemistry Letters and Reviews

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“…In order to improve the efficiency of the synthesis, we planned an alternative synthetic route as shown in Chart 2, involving the Ullmann coupling reaction 10,11) and the Cannizzaro reaction. 12) This sequential method for forming non-symmetrical biaryl compounds via the Ullmann coupling and the Cannizzaro reaction has been reported by Kobayashi et al,13) Moore et al, 14) Bringmann et al, 15) and Seitz and colleagues. 16) According to the retrosynthesis scheme, we selected isovanillin (2) as the starting material for the synthesis of nigricanin (1), which was transformed into 3 by the ortho-selective bromination with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) (Chart 3).…”

mentioning

confidence: 87%

Improved Synthesis of Nigricanin

Abe

Nagai

Imai

et al. 2017

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…NMR-spectra were acquired using a 600 MHz Bruker Avance III HD equipped with a cryogenically cooled 5 mm dual probe optimized for 13 C and 1 H. Samples were dissolved in 600 µL acetone-d6 (Sigma-Aldrich, 99.9 atom % D) and analyzed at 300 K. Data processing was done in Bruker TopSpin. The calibration standard was acetone ( 13 C = 29.84 ppm, 1 H = 2.05).…”

Section: Elemental Analysis (Chns-o)mentioning

confidence: 99%

“…Longer alcohols and esters are most likely formed via aldehyde intermediates, which can undergo Guerbet reactions 8, 9, 22 (higher alcohol synthesis) or Cannizzaro/Tishchenko type reactions 13,14 (aldehyde disproportion to form esters). These solvent-solvent reactions are shown in Fig.…”

Section: Solvent Consumptionmentioning

confidence: 99%

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Solvent consumption in non-catalytic alcohol solvolysis of biorefinery lignin

Nielsen

Jensen

Schandel

et al. 2017

Sustainable Energy Fuels

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a Lignin solvolysis in supercritical alcohols provides a method for producing a deoxygenated liquid bio-oil. Solvent consumption is however inevitable and due to the high cost of alcohols, relative to a bio-oil product, it can hinder commercial viability. In order to investigate the reactions of solvent consumption we studied solvolysis of biorefinery lignin in several primary alcohols. Lignin solvolysis in methanol, ethanol, 1-propanol and 1-butanol performed similarly with respect to bio-oil composition; however, methanol gave much lower bio-oil yield. Solvent consumption increases with reaction temperature for all alcohols and from 10 wt% at 300°C to 35 wt% at 400°C when using ethanol. The mechanism for solvent consumption was found mainly to take place through three different reactions: Direct decomposition to gas through decarbonylation, formation of light condensation products and incorporation of the alcohol into the bio-oil through covalent bonding. Incorporation of the alchohol into the depolymerised oil product by covalent bonding may be a desirable effect which contributes to increased oil yield, inhibition of repolymerisation, reduced oxygen content and elimination of acidity. IntroductionSolvolysis of lignin rich biomass is of growing interest as a process for producing liquid fuels and chemicals. 1, 2 An important issue in such a process is consumption of the solvent, since the cost of solvent may exceed the value of the depolymerised lignin product. Undesired solvent consumption can therefore hinder commercial viability.The mechanisms of solvent consumption in biomass solvolysis reactions are not understood in detail. Alcohols thermally decompose to gasses at elevated temperatures starting already at the supercritical temperature. 3 Even in reactions where the solvent is recognised as being a reactant, and acting as a hydrogen donor, solvent consumption is often an overlooked parameter. 1,2 Reactions in which alcohol solvent is consumed due to reaction with lignin is seen in some studies where the yield of solids and liquid depolymerised lignin species exceed the amount of initially added lignin 4, 5 hence transformation of solvent to biooil must occur. Direct alkylation of depolymerised lignin by ethanol can be described by a mechanism by Zhao et al. 6 , where alcohol radicals facilitate cleavage and resulting in its incorporation in the depolymerised lignin molecule. The alcohol most likely both facilitates lignin polymer cleavage and inhibition of repolymerisation by reaction with reactive radical species formed at elevated temperatures. Barnard investigated the thermal decomposition of ethanol at 576 °C -624 °C and observed significant gas yields and in particular also a brown polymer. 7 Higher alcohol synthesis as described by Guerbet 8, 9 may be responsible for formation of heavier alcohol polymerisation products that will be found in the bio-oil fraction after lignin solvolysis.We previously conducted a parametric study of bio-refinery lignin solvolysis by ethanol assessing the effect of re...

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Ueber den der Benzoësäure entsprechenden Alkohol

Cited by 188 publications

References 0 publications

Recent advances in ionic liquids: green unconventional solvents of this century: part II

Recent advances in ionic liquids: green unconventional solvents of this century: part II

Improved Synthesis of Nigricanin

Solvent consumption in non-catalytic alcohol solvolysis of biorefinery lignin

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