5129-35-1Relevant academic research and scientific papers
A method for esterification reaction rate prediction of aliphatic monocarboxylic acids with primary alcohols in 1,4-dioxane based on two parametrical taft equation
Vojtko, Jan,Tomcik, Peter
, p. 189 - 196 (2014/02/14)
Esterification reaction rates of aliphatic monocarboxylic acids with primary alcohols in 1,4-dioxane as inert solvent were investigated. Acids were esterified with 1-propanol and alcohols with acetic acid as model reactants at a constant temperature of 60°C, at a fixed ionic strength and pH in a batch reactor with a constant volume. For evaluation of reaction rates, an exact kinetic equation for the equilibrium reaction was applied. Under these conditions and for low reactants, concentrations reaction rate depends only on the structure of reactants and, therefore, can be predicted by a correlation equation with two Taft coefficients (inductive and steric effects). From these equations, it is possible to estimate the esterification reaction rate constant for other acid-alcohol pairs. This methodology may also be suitable for other kinetic systems measured under comparable experimental conditions.
Increased activity of enzymatic transacylation of acrylates through rational design of lipases
Syren, Per-Olof,Lindgren, Ebba,Hoeffken, Hans Wolfgang,Branneby, Cecilia,Maurer, Steffen,Hauer, Bernhard,Hult, Karl
experimental part, p. 3 - 10 (2011/02/22)
A rational design approach was used to create the mutant Candida antarctica lipase B (CALB, also known as Pseudozyma antarctica lipase B) V190A having a kcat three times higher compared to that of the wild type (wt) enzyme for the transacylation of the industrially important compound methyl methacrylate. The enzymatic contribution to the transacylation of various acrylates and corresponding saturated esters was evaluated by comparing the reaction catalysed by CALB wt with the acid (H2SO4) catalysed reaction. The performances of CALB wt and mutants were compared to two other hydrolases, Humicola insolens cutinase and Rhizomucor mihei lipase. The low reaction rates of enzyme catalysed transacylation of acrylates were found to be caused mainly by electronic effects due to the double bond present in this class of molecules. The reduction in rate of enzyme catalysed transacylation of acrylates compared to that of the saturated ester methyl propionate was however less than what could be predicted from the energetic cost of breaking the π-system of acrylates solely. The nature and concentration of the acyl acceptor was found to have a profound effect on the reaction rate.
A mild and efficient chemoselective protection of primary alcohols as pivaloyl esters using La(NO3)3·6H2O as a catalyst under solvent-free conditions
Prabhakar,Suryakiran,Venkateswarlu
, p. 732 - 733 (2008/02/09)
Primary alcohols are selectively and efficiently protected as their pivaloyl esters with pivaloyl chloride in the presence of catalytic amounts of La(NO3)3·6H2O at room temperature under solvent-free conditions in excellent yields. Copyright
Determination of Organic Acid Structure Effect on the Equilibrium Constant of Esterification
Vojtko, J.
, p. 1227 - 1235 (2007/10/02)
Equilibrium constants of esterification were measured using both static and dynamic methods.Simultaneously, the measured rate constants of the organic acids esterifications with propanol and the rate constants of propylesters hydrolysis were correlated by the Taft's-equation.It was found, that the equilibrium constant of this reaction does not depend on the structure of the organic acid, and has for T = 60 deg C the value 3.96 +/- 0.08.
