Über die Abhängigkeit der Reaktionsfähigkeit funktioneller Gruppen in Paraffinkohlenwasserstoffen von ihrer Stellung in der Molekel, XV. Hydrolysengeschwindigkeiten der N‐Benzoyl‐, N‐Acetyl‐ und N‐Benzal‐aminooctane

Geiseler, G.; Asinger, Friedrich; Hennig, Günter

doi:10.1002/cber.19610940417

Cited by 7 publications

(2 citation statements)

References 7 publications

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“…The values, taken as a group, are comparable in magnitude with those previously obtained by Willi and Robertson for the acid-catalyzed hydrolysis of benzylideneanilines in 50% aqueous methanol29 and by Geisler, et al, for the hydrolysis of benzylideneaminooctanes in acidic aqueous dioxane. 30 The nature of the rate-determining step in the latter studies is uncertain. Activation parameters have also been measured for the hydrolysis of cyclohexanone oxime in acid31 and for two 2-hydroxybenzylideneanilines32 although uncertainties concerning reaction conditions make comparison with results obtained in this study difficult.…”

Section: Discussionmentioning

confidence: 99%

The Temperature Dependence of the Hydrolysis of a Series of Substituted Benzylidene-1,1-dimethylethylamines

Chaturvedi¹,

Cordes²

1967

J. Am. Chem. Soc.

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Section: Discussionmentioning

confidence: 99%

The Temperature Dependence of the Hydrolysis of a Series of Substituted Benzylidene-1,1-dimethylethylamines

Chaturvedi¹,

Cordes²

1967

J. Am. Chem. Soc.

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“…Reactions which exhibit this behavior also have negative voluines of activation, and the rates of reaction are accelerated by pressure (22). These phenomena are observed in the acid and base hydrolysis of esters and amides (23)(24)(25), and in the transesterification of esters with an alcohol using base catalysis (13,26).…”

Section: Discussionmentioning

confidence: 99%

The Preparation of Sucrose Monoesters

Lemieux¹,

McInnes²

1962

Can. J. Chem.

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The Snell procedure for the preparation of sucrose monoesters of the higher saturated fattp acids by transesterilication of sucrose and rnethyl esters in N,N-dirnethylfor~~ia~~iide was found to yield variable results due to the use of solid potassium carbonate as catalyst and to inlpurities in the solvent. A kinetic study of the reaction revealed that yields of sucrose ester and rates of reaction were reproducible when conditions for homogeneous catalysis were established. The reaction followecl first-ordcr kinetics in methyl ester and s~~c r a t e ion and the rate of reaction was essentially independent of the sucrose concentration, the molecular weight of the fattp acid, and the nature of the metal sucrate used to catalyze the reaction. The activation energy for the reaction \x7as 0.0 Ixal n~ole-I. Eq~~ilibrium constants for the principal reactions were determined, and it was established that only the thermodynamic product prevailed a t any t i~n e thro~~gllout the transesterilication reaction. A preparative method for the synthesis of sucrose monoesters was developed that gave yields of sucrose ester, based on the amount of methyl estcr which had reacted, which were essentially quantitative. The product contained a l~o u t 20'7; of di-and 80% of mono-ester.In 1'354 Snell and co-workers developecl a process for the preparation of fatty acid esters of sucrose ( I ) using the transesterificatioi~ reaction, which was subsequently published in 195G (2). The procedure was based on the reaction of sucrose with the methyl ester of a fatty acid, in N,N-dimethylfoi-~namide ( D M F ) solution, using solid potassium carbonate as a catalyst. The methanol formed in the reaction was removed i 7 z vaclro uitder co~lditions for fractioilal distillation. This process attracted considerable interest from industry as a means for the preparation of sucrose monoesters of the higher fatty acids for use as low-cost, 11011-ionic cletergents (3, 4).The elucidation of the structures of the sucrose monoesters formed and the determ i~l a t i o i~ of their relative amounts in the products obtained first attracted our attention to this process. I-Iowever, when an attempt was made to prepare samples of sucrose mo~loester, by the original Snell proceclure (2), for structural analysis, it soon became apparent that the product clid riot warrant such an investigation since it coulcl not be prepared uncler fully controlled ancl reproducible conditions. For un1;nown reasons, l~i g l~l y variable yields mere obtained and the products differed considerably in the degree of substitution, solubility, and color even when the reaction was performecl under apparently iclentical experimental conclitions ( 5 ) . Although other workers have claimed more success in this respect a critical assessment of their results clearly inclicates that they have been equally unsuccessful i l l preparing reproducibly a product in high yield (2, 6-8). Furthermore, the concl~~sions which the various workers have drawn (2, 6-11) from their experimental results are o...

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Cleavage of the carbon–nitrogen double bond

Bruylants¹,

Medicis²

1970

PATAI'S Chemistry of Functional Groups

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Über die Abhängigkeit der Reaktionsfähigkeit funktioneller Gruppen in Paraffinkohlenwasserstoffen von ihrer Stellung in der Molekel, XV. Hydrolysengeschwindigkeiten der N‐Benzoyl‐, N‐Acetyl‐ und N‐Benzal‐aminooctane

Cited by 7 publications

References 7 publications

The Temperature Dependence of the Hydrolysis of a Series of Substituted Benzylidene-1,1-dimethylethylamines

The Temperature Dependence of the Hydrolysis of a Series of Substituted Benzylidene-1,1-dimethylethylamines

The Preparation of Sucrose Monoesters

Cleavage of the carbon–nitrogen double bond

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