Isopropanol as a solvent for extraction of cottonseed oil

Phase equilibrium data for the system; cottonseed oil-isopropanol-water were determined at 30°C. and compared with data for the system; cottonseed oilethanol-water. The relative phase distribution of fatty acids and cottonseed oil in mixtures with isopropanol and water was studied under varying conditions of water and fatty acid concentrations. These tests showed the fatty acids to be highly concentrated in the alcohol-water phase. Flaked cottonseed meats were extracted in continuous extraction apparatus with 91% isopropanol, 99% isopropanol, and mixtures of commercial hexane and isopropanol. Analytical data on the extractions show that 91% isopropanol is an efficient solvent for extracting active gossypol along with the oil. Rat and swine feeding tests of the isopropanol extracted meal showed it to be highly superior to hydraulic meal as a source of protein. A method was developed for treatment of the cottonseed-isopropanol miscella by liquid-liquid extraction to separate purified oil and fatty acid fractions from other materials in the extract.     

Molecular distillation of a hydrogenated cottonseed oil and certain characteristics of the distilled fractions

Summary 1. A hydrogenated cottonseed oil has been molecularly distilled, and the distilled fractions examined. 2. Fractionation of a molecularly distilled oil occurs, as is to be expected, on the basis of variations in molecular weight of the glycerides. The composition of cottonseed oil is such that there is a considerable separation of the glycerides according to their degree of unsaturation. The composition of peanut oil is such that similar separation can only be slight. Soybean oil is in this respect intermediate between cottonseed oil and peanut oil. 3. Molecular distillation of hydrogenated cottonseed oil causes a segregation of tocopherols and related compounds similar to that observed in peanut oil. However, the fractions first distilled from the oil are relatively weak in antioxygenic properties. It appears probable that their lack of effectiveness is due to the presence of unknown substances capable of inhibiting or counteracting the action of tocopherols. However, the presence of substances other than tocopherols, which respond to or interfere with the Emmerie-Engel test is not to be excluded. The tocopherols in the potent fractions are more effective thana-tocopherol, but less effective than γ-tocopherol. This is one of four regional research laboratories operated by the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Solubility of tristearin and hydrogenated cottonseed oil in certain aceto- and butyroglycerides

Summary Tristearin, triolein, 1,2-diaceto-3-olein, an acetoolein product, and 1,2-dibutyro-3-olein were prepared. Also a commercial, refined, and bleached cottonseed oil was hydrogenated to obtain products having iodine values of 29.3 and 1.1. Solubility measurements were made for the mixtures tristearin-triolein, tristearin-1,2-diaceto-3-olein, tristearin-1,2-dibutyro-3-olein, and for hydrogenated cottonseed oils in the aceto-olein product and cottonseed oil. In mixtures containing from 0.18% to approximately 30% of tristearin the solubility on a weight basis was unaffected by the nature of the oil. On a mole fraction basis the tristearin was most soluble in the triolein and least soluble in the 1,2-diaceto-3-olein. Hydrogenated cottonseed oil appeared to be about equally soluble, on a weight basis, in the aceto-olein product and cottonseed oil. Presented at the 45th annual meeting of the American Oil Chemists’ Society, San Antonio, Tex., April 12–14, 1954. One of the laboratories of the Southern Utilization Research Branch, Agricultural Research Service, United States Department of Agriculture.     

Epoxidized jojoba oil as a stabilizer for vinyl chloride containing plastics

Summary Epoxidized jojoba oil has been evaluated as a light and heat stabilizer for vinyl chloride containing plastics and its properties, intercompared with those of other epoxides representative of three major classes of oxirane stabilizers. The results obtained show that epoxidized jojoba oil is a satisfactory thermal and ultraviolet stabilizer for both TCP and DOP plasticized stocks and has no adverse effects on the plasticizer properties of these materials. In general, epoxidized jojoba oil was found to be equivalent to or, in some instances, superior to the other epoxides tested.     

Investigation of dendrimer-based supramolecular networks as a new clay stabilizer for oil field

A novel cationic copolymer was synthesized with acrylamide (AM), [2-(acryloyloxy)ethyl]trimethylammonium chloride (DAC) and 1-allyl-3-phenyl thiourea (APTU). In association with hyperbranched poly (amido amine) (h-PAMAM) guanidine, a dendrimer-based supramolecular composite polymer solution as a new clay stabilizer was prepared. The inhibiting properties have been tested through various approaches including antiswelling, hot-rolling recovery, and erosion resistant analysis. The optimal concentrations of h-PAMAM guanidine and P(AM-DAC-APTU) were 100 and 5,000 mg/L, separately. In this case, the supramolecular complex showed an excellent retention ratio of 87.6% and made a great progress in inorganic salts and temperature resistances. Moreover, after sourcing with the deionized water for five times, the antiswelling degree of composite solution was stabilized at 73.3%, showing high potential to use this new clay stabilizer for oil field.     

Oxidative stability of hydrogenated menhaden oil shortening blends in cookies,crackers, and snacks

The oxidative stability of partially hydrogenated menhaden fish oil (PHMO) shortening/canola oil blends with added antioxidant tertiary butylhydroquinone (TBHQ) and various blended partially hydrogenated vegetable oil (PHVO) shortenings without antioxidant in aged cookies and crackers was analyzed by anisidine value (AV), peroxide value (PV), and Totox value. The results showed no significant differences (P<0.05) for PV, AV, or Totox value between the PHMO shortening containing TBHQ and the PHVO shortening in cookies, crackers, and deep-fried extruded snacks, except for the AV and Totox value of crackers.     

Refining method for crude cottonseed oil

Conclusion Acknowledgment is again given to Mr. Nelson W. Humbaugh who carried out the analytical work here recorded. A proposed revision of the refining method as at present written which is intended to embody all the points found desirable, is now in the hands of the members of the Refining Committee for consideration and test.     

Hydrogenated cottonseed oil as a substitute for palm oil in the production of tin plate and cold reduced sheet steel

Summary Work has been reported on the development of a substitute for palm oil, which is used to the extent of about 40 million pounds annually in the production of tin and terne plate, and in the cold reduction process for the manufacture of strip steel. This investigation included an examination of the chemical and physical properties of virgin and spent palm oils, especially with respect to the effect of these properties on the action of these oils in the tin bath. Based on the results of this investigation, and on information and cooperation of various producers and consumers of tin plate, efforts were made to produce from cottonseed oil a product which would be equal to or superior to palm oil with respect to its performance in the tin bath. It was found that, of the various types of selectivity hydrogenated cottonseed oils which were investigated, one having an iodine number of approximately 50 was best adopted as a palm oil substitute for use in the tin bath. The effect of heating hydrogenated cottonseed oils on the viscosity, rates of free fatty acid formation, rate of volatilization, effect of flux, and other factors were determined. Based on these results and further evaluation of the hydrogenated cottonseed oils by various producers of tin plate, specifications were formulated covering a product which it is believed will provide optimum performance and maximum life in the tin bath. Presented before American Oil Chemists’ Society, Chicago, Illinois, October 8–9, 1942.     

Metabolism of erucic acid in perfused rat liver: Increased chain shortening after feeding partially hydrogenated marine oil and rapeseed oil

The metabolism of [14-¹⁴C] erucic acid was studied in perfused livers from rats fed on diets containing partially hydrogenated marine oil or rapeseed oil for three days or three weeks. Control rats were given groundnut oil. Chain-shortening of erucic acid, mainly to 18∶1, was found in all dietary groups. In the marine oil and rapeseed oil groups, the percentage of chain-shortened fatty acids in very low density lipoproteins-triacylglycerols (VLDL-TG) exported from the liver increased after prolonged feeding. A similar increase was found in liver TG only with partially hydrogenated marine oil. This oil, rich intrans fatty acids, thus seemed to be more effective in promoting chain-shortening. The fatty acid composition of the secreted and stored TG differed both with respect to total fatty acids and radioactively labeled fatty acids, indicating that at least 2 different pools of TG exist in the liver. The lack of lipidosis in livers from rats fed dietary oils rich in 22∶1 fatty acids is discussed in relation to these findings. In conclusion, a discussion is presented expressing the view that the reversal of the acute lipidosis in the hearts of rats fed rapeseed oil or partially hydrogenated marine oils is, to a large extent, derived from the increased chain-shortening capacity of erucic acid in liver.     

Gamma-tocopherol as a precursor of a red quinoid substance developed in cottonseed oil during oxidation

Summary On the basis of spectrophotometric data on the characteristic spectral absorptions observed in oxidizing substrates with and without added γ-tocopherol, it has been shown that the red color which develops on accelerated oxidation of fat substrates containing this tocopherol results from its conversion to chroman-5,6-quinone. The chroman-5,6-quinone thus produced possesses relatively little antioxidant activity. Presented before the American Oil Chemists’ Meeting, New Orleans, Louisiana, May 10 to 12, 1944. National Cottonseed Products Association Fellow. This is one of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Crystallization characteristics of hydrogenated canola oil as affected by addition of palm oil

Addition of palm oil at levels of 5, 10 and 15% to selectively and nonselectively hydrogenated canola oil increased the time of isothermal crystallization at 20°C and delayed the appearance of the isothermal crystallization peak as determined by DSC. The degree of supercooling was also increased. Addition of palm oil to canola oil before selective or nonselective hydrogenation decreased the time of the appearance of the isothermal crystallization peak. Rates of crystallization were determined in selectively hydrogenated canola palm oil mixtures which followed first order kinetics.     

Polymorphic stability of hydrogenated canola oil as affected by addition of palm oil

Palm oil was added to canola oil before and after hydrogenation and the effect of this addition on the polymorphic stability of the hydrogenated oils was investigated. Palm oil was added to canola oil at two levels to produce hydrogenated canola and palm oil blends containing 5 and 10% palm oil. The levels of palm oil added to hydrogenated canola oil were 5, 10 and 15%. Samples were subjected to temperature cycling between 5 and 20°C as well as storage at 5°C up to 56 days. X-ray diffraction and polarized light microscopy were used to follow the changes of polymorphic form and crystal growth, respectively, during cycling and storage. Theβ-crystal contents of the oils were quantified based on the relative density of the characteristic short spacings using a Soft Laser Scanning Densitometer. The delaying effect of palm oil on phase transition was observed using Differential Scanning Calorimetry. Palm oil showed no effect on the polymorphic stability of the temperature cycled selectively hydrogenated oil, however, it delayed the transition rate at a constant temperature of 5°C. Addition of palm oil at the 10% level before hydrogenation and the level after hydrogenation proved to be effective in delaying polymorphic instability of nonselectively hydrogenated canola oil. Theβ′ stabilization effect of palm oil on the polymorphic stability of hydrogenated canola oil is most likely due to a decrease of fatty acid chain length uniformity.     

An aqueous ethanol extraction process for cottonseed oil

A bench-top process for the extraction of cottonseed flakes with aqueous ethanol has been developed. The process consists of cottonseed meat flaking, drying and extraction with boiling, aqueous ethanol (95% by volume) at atmospheric pressure. The resulting miscella is chilled, producing free oil, emulsified oil and mucilaginous gum. The heterogeneous solution is processed through a phase separator where free and emulsified oil and gum are separated from oil-lean miscella. The oil and gum phases are treated with caustic soda and centrifuged to produce semirefined oil containing about 4% volatiles. The miscella phase, containing about 3.3% lipid-like material and 1% petroleum ether insolubles, is reheated and recycled to the extractor. After the marc is pressed foots are added, and it is desolventized to produce a meal having a residual oil content less than 1%. Although not yet otpimized, the process shows potential for scaleup to pilot plant processing and adaptability to current oil mill solvent operations. Presented at the AOCS annual meeting, Chicago, May 1983.     

Gaseous ammonia as a refining agent for cottonseed oils

In this investigation the application of gaseous ammonia to cottonseed oil refining was explored. The ammonia reacted quantitatively with the free fatty acids in the oil; its solubility in coftonseed oil was determined as a function of pressure. In “degumming” it was more efficient in removing phosphatides than other agents. A reduction in refining loss resulted for oils refined with gaseous ammonia as outlined and compared with the standard AOCS cup loss analysis. However, the oil colors were substantially higher even though the ammonia treated oils were re-refined with caustic solution. Results using cottonseed oil-hexane “miscellas” containing less than 70% oil showed low refining losses, but the colors were estremely high. Above 70% oil content the losses were higher, but the colors were lower. The colors never equalled “standard cup” results. This study was sponsored by the Texas Engineering Experiment Station and the Cotton Research Committee of Texas.     

Evaluation of partially hydrogenated methyl esters of soybean oil as biodiesel

Biodiesel, an alternative fuel derived from vegetable oils or animal fats, continues to undergo rapid worldwide growth. Specifications mandating biodiesel quality, most notably in Europe (EN 14214) and the USA (ASTM D6751), have emerged that limit feedstock choice in the production of biodiesel fuel. For instance, EN 14214 contains a specification for iodine value (IV; 120 g I₂/100 g maximum) that eliminates soybean oil as a potential feedstock, as it generally has an IV >120. Therefore, partially hydrogenated soybean oil methyl esters (PHSME; IV = 116) were evaluated as biodiesel by measuring a number of fuel properties, such as oxidative stability, low‐temperature performance, lubricity, kinematic viscosity, and specific gravity. Compared to soybean oil methyl esters (SME), PHSME were found to have superior oxidative stability, similar specific gravity, but inferior low‐temperature performance, kinematic viscosity, and lubricity. The kinematic viscosity and lubricity of PHSME, however, were within the prescribed US and European limits. There is no universal value for low‐temperature performance in biodiesel specifications, but PHSME have superior cold flow behavior when compared to other alternative feedstock fuels, such as palm oil, tallow and grease methyl esters. The production of PHSME from refined soybean oil would increase biodiesel production costs by US$ 0.04/L (US$ 0.15/gal) in comparison to SME. In summary, PHSME are within both the European and American standards for all properties measured in this study and deserve consideration as a potential biodiesel fuel.     

Monoethylenic fatty acids of a partially hydrogenated herring oil

A Canadian Atlantic herring oil hydrogenated for margarine use to an iodine value of 76 and melting point of 32.5 C was found to have 30% saturated acids and 66% monounsaturated fatty acids. The monounsaturated fatty acids could be analytically determined ascis andtrans isomers by open tubular gas liquid chromatography.Trans acids were 33% of the C₁₆ and C₁₈ monounsaturated acids, and 32 and 28%, respectively, of the C₂₀ and C₂₂ monounsaturated acids. After separation of geometric isomers by Florisil-silver nitrate chromatography the positional isomers in each class were determined by oxidative fission. The double bond positions of the originalcis fatty acids were largely retained in bothcis andtrans isomers, but additional isomers were observed, especially in thetrans fatty acids.