Diglyceride-rich oils from glycerolysis of edible vegetable oils

Commercial edible vegetable oils in which part of their triglycerides are substituted with 1,3-diglycerides are healthier for human consumption than the original oils. This is because the human metabolism of 1,3-diglycerides is believed to occur through a distinct pathway with less probability of being deposited as fat in the body tissues. To obtain these enriched oils, conversion of triglycerides into diglycerides is carried out by glycerolysis using commercial crude glycerol containing dissolved alkali cations that homogeneously catalyze the reaction. The addition of a food production-compatible MgO as a supplementary solid basic catalyst, shortens the reaction time by half due to a combination of homogeneous and heterogeneous catalysis processes. In either homogeneously or homogeneousheterogeneously catalyzed glycerolysis, the increase of the reaction temperature in the range of 453-493 K increases the final 1,3-diglyceride content. Furthermore, in both glycerolysis processes the triglyceride content can be decreased in more than 60% with the consequent increase of total diglycerides to 50%, 70% of which are the 1,3-isomers. The glycerolysis reaction proceeds without altering the fatty acid distribution of the original oils.

Section: Resultsmentioning

confidence: 99%

“…Solvent flow rate and oven temperature were selected as 0.7 mL/min and 323 K, respectively. Further details are given in a previous work (Ferretti et al, ).…”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Synthesis of Edible Vegetable Oils Enriched with Healthy 1,3‐Diglycerides Using Crude Glycerol and Homogeneous/Heterogeneous Catalysis

Dosso

Luggren

Cosimo

2020

Na₂SiO₃‐Catalyzed Glycerolysis of Sacha Inchi (Plukenetia volubilis L.) Oil into Di‐ and Monoacylglycerols

Luo

Wang

Deng

et al. 2020

Direct glycerolysis of novel edible Sacha Inchi (Plukenetia volubilis L.) seed oil (PvLO) into diacylglycerols (DAG) and monoacylglycerols (MAG) was studied over solid Na2SiO3 with or without microwave assistance. The glycerolysis yield was calculated by qualitative and semiquantitative analyses of 1H NMR, 13C NMR, and FT‐IR spectra. The yields of ~33% 1, 3‐DAG, ~16% 1, 2‐DAG, ~40% 1‐MAG, and ~2.3% 2‐MAG were achieved after 16 hours at 120 °C in three consecutive cycles using acetone, with an interesterification rate of 92%. The modified oil showed enhanced gelation ability at low temperatures. The yield of 1, 2‐DAG can be increased by adding acetone as solvent. The fatty acid compositions and unsaturated structure of lipids were less destroyed after alkaline glycerolysis. However, more α‐linolenic and linoleic acids were transferred to the sn‐2 position of glyceryl skeleton. The oxidative stability of the modified oil was still controllable. In summary, this work provides a feasible method to convert polyunsaturated plant oils into oils rich in DAG and MAG with less destructive impact on the olefinic structure of oil. Also, it provides a useful example of how to quickly evaluate the influence of chemical modification on the chemical structure of plant oils by using various spectral technologies.

Glycerolysis of Buriti Oil (Mauritia flexuosa) by Magnesium Oxide and Immobilized Lipase Catalysts: Reaction Yield and Carotenoids Degradation

Silva

Bönmann

Kuamoto

et al. 2021

Buriti (Mauritia flexuosa) is a palm tree widely distributed in South America. The oil extracted from its fruit is an added value product for its high carotenoids content. The aim of this work was to evaluate the alkaline (magnesium oxide-MgO) and enzymatic (lipase B from Candida antarctica immobilized on macroporous acrylic resin) glycerolysis of buriti oil to obtain non-ionic emulsifiers and evaluate the carotenoids degradation during this process. Alkaline glycerolysis was carried out using a 3:1 glycerol/oil molar ratio, temperatures of 170 and 210 C, and MgO contents of 0.5 and 1%wt. Enzymatic glycerolysis reactions were performed using 3%wt. of a lipase catalyst and varying the following parameters: glycerol: oil molar ratio (3:1, 6:1, and 9:1), solvent (tert-butyl alcohol) concentration (50%, 150%, and 250%, vol./substrate mass), and temperature (40, 55 and 70 C). The products were analyzed by liquid chromatography and UV-visible spectroscopy (370-520 nm). Enzymatic glycerolysis was superior in terms of conversion and selectivity to monoacylglycerols (MAG). MAG yields were close to 80% or higher for most conditions tested for enzymatic glycerolysis, while the maximum yield for alkaline glycerolysis was of 58%. UV-Vis data showed that carotenoids were severally degraded in alkaline glycerolysis, while the enzymatic product exhibited high preservation of carotenoids and color and odor similar to those of the pure buriti oil. Based on the final composition of the non-ionic emulsifiers obtained from buriti oil by enzymatic glycerolysis, they can be considered potential raw materials for cosmetic and food industries.