Catalytic transfer hydrogenation of soybean oil

Šmidovnik, Andrej; Štimac, Anton; Kobe, J.

doi:10.1007/bf02540939

Cited by 35 publications

(31 citation statements)

References 16 publications

(18 reference statements)

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“…Moreover, no special reactors are required and the solvent is used as a hydrogen donor along with a selected catalyst. The CTH process using Pd/C catalyst and different hydrogen donor solvents have also been reported for soy [31], sunflower [32], and castor [16,33] oils.…”

Section: Hydrogenationmentioning

confidence: 99%

Castor oil as a potential renewable resource for the production of functional materials

Mubofu

2016

Sustain Chem Process

170

124

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Castor oil is increasingly becoming an important bio-based raw material for industrial applications. The oil is nonedible and can be extracted from castor seeds from the castor plant belonging to the family Euphorbiaceae. The oil is a mixture of saturated and unsaturated fatty acid esters linked to a glycerol. The presence of hydroxyl group, a double bond, carboxylic group and a long chain hydrocarbon in ricinoleic acid (a major component of the oil), offer several possibilities of transforming it into variety of materials. The oil is thus a potential alternative to petroleum-based starting chemicals for the production of materials with variety of properties. Despite this huge potential, very little has recently been reviewed on the use of castor oil as a bio-resource in the production of functional materials. This review therefore highlights the potential of castor oil in the production of these diverse materials with their projected global market potential. The review gives the background information of castor oil and its geographical availability, the properties and its uses as bio-based resource for synthesis of various materials. The review further highlights on the use of castor oil or ricinoleic acid as a green capping agent in the synthesis of nanomaterials.

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Section: Hydrogenationmentioning

confidence: 99%

Castor oil as a potential renewable resource for the production of functional materials

Mubofu

2016

Sustain Chem Process

170

124

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“…The dominant mechanism of hydrogenation in the present investigation involves the use of formic acid to transfer hydrogen to the canola oil (Scheme 1). Research (8) has shown that the formate ion can be used for hydrogenation of vegetable oils under the temperature conditions used in this study. One of the products of chemical reaction between the formate ion and vegetable oil in the presence of water is the bicarbonate anion.…”

Section: Resultsmentioning

confidence: 98%

“…DDAB was obtained from Fluka (St. Louis, MO), and sodium formate (99.8%) and formic acids (97%) were obtained from Alfa Essar (Ward Hill, MA). Both sodium formate and formic acid are approved food-grade materials that have been used in past research to hydrogenate edible oils (8,9). Formic acid is used as a preservative and flavor adjunct (13).…”

Section: Methodsmentioning

confidence: 99%

“…In other studies, Š midovnik and colleagues (8,9) used sodium formate and other hydrogen donors to transfer hydrogen chemically to vegetable oils (soybean, corn, peanut, and olive) at temperatures as low as 50°C. In their approach, formate ion is converted to bicarbonate ion upon oxidation; thus, the reaction rate decreases with time, although large amounts of sodium formate (typically 15 g of oil in 40 mL of 6.5 M sodium formate) are used.…”

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confidence: 97%

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Electrochemical hydrogenation of canola oil using a hydrogen transfer agent

Mondal

Lalvani

2003

J Americ Oil Chem Soc

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A novel low-temperature process for the electrochemical hydrogenation of canola oil is described. An emulsion of oil and water containing formic acid and a nickel hydrogenation catalyst, placed in the cathode compartment of an electrolysis cell and subjected to an electrical current, underwent hydrogenation at temperatures as low as 45°C. At these low temperatures of hydrogenation, the trans FA content of the hydrogenated canola oil was very low as compared with that of the edible oils hydrogenated by commercial processes using high temperature and high partial pressure of hydrogen gas. Because of its adverse health effects, a high trans FA content in edible oils is viewed as undesirable. In addition to the commercially available nickel supported on silica, amorphous nickelphosphorus alloys supported on a variety of substrates were also used. Amorphous alloys are generally very corrosion resistant because of the absence of grain boundaries. A mechanism for hydrogenation using the hydrogen transfer agent of formic acid and its continuous regeneration at the cathode was evoked to explain the experimental data. FIG. 2.Iodine value and trans FA content vs. hydrogen transfer agent for different catalyst loadings (g/L labels for the various plots refer to the catalyst loadings). Reaction conditions: −0.5 V vs. saturated calomel electrode (SCE), 45°C, 0.26 g didodecyl diethyl ammonium (DDAB), pH 3.8.

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“…Catalytic transfer hydrogenation (CTH) is a common procedure in organic chemistry, although there are only a few examples of CTH being used for the hydrogenation of vegetable oils (11)(12)(13). The advantage of CTH, compared with classical heterogeneous systems, is its simplicity: It requires only moderate temperatures and pressures, with the hydrogen donor (usually formic acid or alcohols) being used as the solvent and nickel (Ni) or palladium (Pd) as the catalyst.…”

mentioning

confidence: 99%

Castor oil hydrogenation by a catalytic hydrogen transfer system using limonene as hydrogen donor

Martinelli

Schneider

Baldissarelli

et al. 2005

J Americ Oil Chem Soc

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The hydrogenation of castor oil was investigated using a catalytic transfer hydrogenation system in which palladium on carbon was the catalyst and limonene was the solvent and hydrogen donor. The highest percentage of castor oil modification occurred at 178°C using 1% Pd/C and an oil/limonene ratio of 1:3. The optimized system presented very good reproducibility and 100% conversion of the ricinoleate. GC using a mass spectrometer as detector and 1 H NMR spectra of the products indicated that hydrogenation was accompanied by dehydrogenation leading to a mixture of 12-hydroxy and 12-keto stearic derivatives.Paper no. J10895 in JAOCS 82, 279-283 (April 2005).KEY WORDS: CTH, hydrogenation of castor oil, hydrogen donor, hydroxy stearic ester, keto stearic ester, palladium catalyst.

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Catalytic transfer hydrogenation of soybean oil

Cited by 35 publications

References 16 publications

Castor oil as a potential renewable resource for the production of functional materials

Castor oil as a potential renewable resource for the production of functional materials

Electrochemical hydrogenation of canola oil using a hydrogen transfer agent

Castor oil hydrogenation by a catalytic hydrogen transfer system using limonene as hydrogen donor

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