2277-23-8Relevant articles and documents
Enzymatic synthesis of 1,3-dicaproyglycerol by esterification of glycerol with capric acid in an organic solvent system
Sanchez, Daniel Alberto,Tonetto, Gabriela Marta,Ferreira, Maria Lujan
, p. 7 - 18 (2014/01/06)
In this work, the esterification of glycerol with capric acid catalyzed by an immobilized form of a 1,3-positionally selective lipase (Rhizomucor miehei) showed to be effective for the synthesis of 1,3-dicaprin in n-heptane as the reaction medium. The effects of the reaction parameters were studied using an experimental factorial design of three factors and three levels with two central points. The selected experimental variables were amount of glycerol adsorbed on silica gel (G), biocatalyst load (E) and reaction temperature (T), and the response variables were total conversion of capric acid, acylglycerol fractions, selectivity and yield of dicaprin, and acyl migration reaction. The range of each parameter was selected as follows: G = 50-250 mg, E = 20-40 mg and T = 40-60 C. At optimum conditions 73% capric acid conversion was achieved, with 76% dicaprin selectivity, and selectivity to the specific 1,3-dicaprin of 70% of total products. An adequate selection of the reaction conditions is necessary not only to maximize the conversion of capric acid, but also to minimize the acyl migration reaction and the generation of undesired products. Evidence of kinetically controlled enzymatic acyl migration from sn-3/sn-1 to sn-2 is presented.
1-O-Alkyl (di)glycerol ethers synthesis from methyl esters and triglycerides by two pathways: Catalytic reductive alkylation and transesterification/reduction
Sutter, Marc,Dayoub, Wissam,Metay, Estelle,Raoul, Yann,Lemaire, Marc
supporting information, p. 786 - 797 (2013/04/24)
From available and bio-sourced methyl esters, monoglycerides or oleic sunflower refined oil, the corresponding 1-O-alkyl (di)glycerol ethers were obtained in both high yields and selectivity by two different pathways. With methyl esters, a reductive alkylation with (di)glycerol was realized under 50 bar hydrogen pressure in the presence of 1 mol% of Pd/C and an acid co-catalyst. A second two step procedure was evaluated from methyl esters or triolein and consisted of a first transesterification to the corresponding monoglyceride with a BaO/Al2O3 catalyst, then its reduction to the desired glycerol monoether with a recyclable heterogeneous catalytic system Pd/C and Amberlyst 35 under H2 pressure. In addition, a mechanism for the reaction was also proposed.
Glyceride synthesis in a solvent-free system
Fureby,Adlercreutz,Mattiasson
, p. 1489 - 1495 (2007/10/03)
Synthesis of partial glycerides in a solvent-free system has been investigated with various acyl donors and glycerol as substrates and a 1,3-specific immobilized lipase to catalyze the reaction. Capric acid was the most efficient acyl donor, compared with ethyl caprate and tricaprin. However, to obtain a high yield of dicaprin and a low amount of tricaprin, ethyl caprate was the acyl donor of choice. The composition of the product mixture was determined by the ratio of ethyl caprate to glycerol; a molar ratio of 3:1 was optimum for dicaprin synthesis. The water content in glycerol did not influence the final yield of dicaprin, but initial production of capric acid increased with increasing water content. The reaction was found to be controlled entirely by external mass transfer. The yield of diglyceride could be increased from 70 to 90% by lowering the reaction temperature, so that the diglyceride precipitated during the reaction.
