Performance of Liquid Eversa on Fatty Acid Ethyl Esters Production by Simultaneous Esterification/Transesterification of Low-to-High Acidity Feedstocks

Liquid Eversa was evaluated in hydrolysis of acylglycerols from soybean oil deodorizer distillate (SODD), as well as simultaneous esterification/transesterification of SODD with low-to-high free fatty acids (FFAs) content using ethanol as acyl acceptor. Hydrolysis of SODD at mild temperature (37 °C) and without pH control (water:SODD mass ratio of 4:1) increased its FFAs content from 17.2 wt.% to 72.5 wt.% after 48 h reaction. A cold saponification of SODD allowed a saponification phase (SODD-SP) to be recovered with 93 wt.% saponification index and 2.25 wt.% FFAs content, which was used to find the experimental conditions for simultaneous esterification/transesterification reactions by experimental design. Temperature of 35 °C, enzyme concentration of 8.36 wt.%, and molar ratio of 3.64:1 (ethanol:SODD-SP) were found as the best conditions for fatty acid ethyl esters (FAEEs) production from SODD-SP (86.56 wt.% ester yield after 23 h reaction). Under the same reaction conditions, crude SODD (17.2 wt.% FFAs) and hydrolyzed SODD (72.5 wt.% FFAs) yielded products containing around 80 wt.% FAEEs. Caustic treatment could increase the ester content to around 90 wt.% and reduce the FFAs content to less than 1 wt.%. Our results show the good performance of liquid Eversa in aqueous (hydrolysis reactions) and organic (esterification/transesterification reactions) media.

Synthesis of Alpha Olefins: Catalytic Decarbonylation of Carboxylic Acids and Vegetable Oil Deodorizer Distillate (VODD)

Decarbonylation of carboxylic acids provides an effective protocol for producing alpha olefins; however, previous literature has focused on the palladium-bisphosphine catalysts and has only sporadically studied the palladium-monophosphine catalyst. To investigate the catalytic activity of the palladium-monophosphine catalyst on decarbonylation of carboxylic acids, new monophosphine ligands were synthesized (NP-1, NP-2, CP-1 and CP-2). By employing (1–3 mol%) palladium-naphthylphosphine catalysts, various carboxylic acids were converted into corresponding alpha alkenes with good yields and selectivity within a short period of time. Vegetable oil deodorizer distillate (VODD), which is a by-product from the vegetable oil refinery process, was found to be rich in free fatty acids and there is great interest in turning vegetable oil deodorizer distillate into value-added compounds. It is noteworthy that our catalytic system could be applied to convert vegetable oil deodorizer distillate (VODD) into diesel-like hydrocarbons in a good yield.

Novel Fast Chromatography-Tandem Mass Spectrometric Quantitative Approach for the Determination of Plant-Extracted Phytosterols and Tocopherols

Phytosterols and tocopherols are commonly used in food and pharmaceutical industries for their health benefits. Current analysis methods rely on conventional liquid chromatography, using an analytical column, which can be tedious and time consuming. However, simple, and fast analytical methods can facilitate their qualitative and quantitative analysis. In this study, a fast chromatography-tandem mass spectrometric (FC-MS/MS) method was developed and validated for the quantitative analysis of phytosterols and tocopherols. Omitting chromatography by employing flow injection analysis—mass spectrometry (FIA-MS) failed in the quantification of target analytes due to analyte-to-analyte interferences from phytosterols. These interferences arise from their ambiguous MS fingerprints that would lead to false identification and inaccurate quantification. Therefore, a C18 guard column with a 1.9 µm particle size was employed for FC-MS/MS under isocratic elution using acetonitrile/methanol (99:1 v/v) at a flow rate of 600 µL/min. Analyte-to-analyte interferences were identified and eliminated. The false peaks could then be easily identified due to chromatographic separation. In addition, two internal standards were evaluated, namely cholestanol and deuterated cholesterol. Both internal standards contributed to the observed analyte-to-analyte interferences; however, adequate shift in the retention time for deuterated cholesterol eliminated its interferences and allowed for an accurate quantification. The method is fast (1.3 min) compared to published methods and can distinguish false peaks observed in FIA-MS. Seven analytes were quantified simultaneously, namely brassicasterol, campesterol, stigmasterol, β-sitosterol, α-tocopherol, δ-tocopherol, and γ-tocopherol. The method was successfully applied in the quantitative analysis of phytosterols and tocopherols present in the unsaponifiable matter of canola oil deodorizer distillate (CODD). β-sitosterol and γ-tocopherol were the most abundant phytosterols and tocopherols, respectively.

Influence of Industrial Processing on Physiochemical Characteristics of Soybean Oil and Deodorizer Distillates

The present study aimed to evaluate the impact of industrial processing (neutralization/degumming, bleaching, and deodorization) on physicochemical characteristics of soybean oil and soybean oil deodorizer distillate (SBO-DD) collected from two different industries. The substantial impact of processing was observed on all physicochemical parameters except the iodine value (IV) and saponification value (SV). Gas chromatography-flame ionization detector (GC-FID) and Gas chromatography-mass spectrometry (GC-MS) analytical techniques were used for the quantification of individual fatty acids, sterols, and 3-monochloropropane diol (3-MCPD) ester. Among the fatty acids, palmitic and linoleic acids were present at higher concentrations in all processing stages. Among sterols, β-sitosterol was found to be higher (25.65 and#181;g/g) in crude soybean oil and reduced to 16.44 and#181;g/g after processing till the final deodorization stage. 3-MCPD ester was developed during the neutralization/degumming process and further increased during bleaching and deodorization up to 315 and#181;g/kg, respectively. SBO-DD was found to be a rich source of total and individual sterols as compared to crude or processed soybean oil. High free fatty acid (FFA) level in deodorizer distillate indicated that SBO-DD is a potential source of biodiesel production.