Extraction of Phospholipids from Egg Yolk Flakes Using Aqueous Alcohols

Two alcohols, ethanol and butanol, with different water contents were evaluated for phospholipids (PL) sequential extraction from drum dried egg yolk flakes. It showed that butanol was more effective in extracting total yolk lipids compared to ethanol, but the PL in the extract had the same concentration as in the original yolk total lipid. The use of aqueous ethanol of 95 and 75% resulted in lipid extracts with higher PL concentration during the initial stages of the sequential extraction. When ethanol was further diluted to a concentration of 55%, the solvent lost its PL extraction ability, and the total lipid recovery also decreased dramatically. When both the PL purity and recovery were considered, 75% ethanol was the most effective aqueous alcohol for PL extraction and enrichment from the yolk flakes. In the first stage of extraction using such a solvent, 67% of the total PL in the original yolk was recovered in a lipid fraction with a PL purity of 75%. This study identified the optimal ethanol concentration for PL extraction from dried egg yolk. With this information, the best solid:solvent ratio can be designed to extract and enrich the polar lipids from lipid-bearing materials with known moisture content using a renewable or “green” solvent, ethanol.     

Bland undenatured soybean flakes by alcohol washing and flash desolventizing

The conditions for removing the beany and bitter flavor from defatted soybean meal with ethanol and isopropyl alcohol were investigated. In the presence of alcohols, soybean protein is extremely sensitive to denaturation when temperature, moisture, and residence time are increased. If protein is to be isolated in good yield and quality, retention of the original, high watersolubility is important, and denaturation must be kept to a minimum. Defatted soybean flakes were successfully debittered by countereurrent washing with aqueous alcohols on a pilot-plant scale, and the entrained solvent was recovered by flash desolventizing without excessive denaturation of protein. Effective debittering was obtained with 95 volume percentage ethanol and 91 volume percentage isopropyl alcohol whereas satisfactory flavor was not obtained with absolute ethanol. The solubility of the nitrogenous compounds in the meal product (Nitrogen Solubility Index—NSI=water-soluble nitrogen×100÷ total nitrogen) was maintained at 68 NSI, or higher, regardless of the solvent system or conditions used when starting with 80 NSI defatted flakes. Residual alcohol in the desolventized products was reduced to 1–2% with the aqueous alcohol system and to less than 1% for the absolute alcohol system. Lower residual values can be obtained by recycling the material through the desolventizing unit. The desolventizing system described is simple, low in cost, and should be useful in any process requiring the rapid removal of solvent from residual solids where heat-sensitive constituents are present.     

Development of a pilot-plant process for the extraction of soy flakes with aqueous isopropyl alcohol

Soy flakes were extracted with aqueous isopropyl alcohol (IPA) at 77 C in a Kennedy countercurrent continuous extractor at a retention time of 71 min. IPA concentration was varied from 85.0 to 90.5% w/w and included the 87.7% IPA-water azeotrope. Solvent to meal ratios were varied from 1.5 to 3.0. The oil-IPA miscella leaving the extractor was chilled and coalesced to yield an oil phase and an IPA phase. The IPA phase was recycled to the extractor without being distilled. Excess IPA was expressed from the defatted flakes, and this also was recycled to the extractor. IPA recovered by distillation in the evaporator-stripper and desolventizer-toaster accounted for less than 10% of the total. Refined deodorized oils from the IPA extraction process compared favorably with their hexane counterpart in color, peroxide value and phosphorous and free fatty acid contents. Desolventized meals from the IPA process compared favorably with their hexane-extracted counterpart in protein, ash and fiber content.     

Solvent extraction of cottonseed and peanut oils. VIII. Effects of moisture on the preparation and flaking of cottonseed

Conclusions The results indicate that 9 to 10% moisture in the meats is the best level for the preparation of cottonseed into flakes for solvent extraction. At lower moisture the flakes contain more fines before and after agitation in solvent, and the percolation rate of solvent through a flake bed is lower because of reduced particle size. At higher moisture the amount of oil in the hulls from the beater is greater. Also the flakes produce more fines, and the percolation rate becomes slower because of the softness and pliability of the flaked meat. It is likely that in commercial continuous operations this packing or balling up tendency of the flaked meats may lead to periodic channeling or plugging in the extractor, dryer, conveyors, and filters. These conclusions have been applied in the continuous pilot plant solvent extraction of three lots of prime cottonseed. The results substantiate the findings herein and will be reported in a separate publication. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Flash desolventizing defatted soybean meals washed with aqueous alcohols to yield a high-protein product

A vapor-type desolventizer was developed previously at this laboratory to recover hexane and concentrated alcohols from soybean mares. The work reported in this paper extends the application of this unit to the recovery of dilute alcohols. Soybean protein meals washed with aqueous alcohols are debittered to yield a better flavored product with a significant increase in protein content. The protein of defatted meal was increased from about 50 to 70 or 75% by washing with methanol, ethanol, or isopropyl alcohol in a concentration range of 50–70%. System modifications and critical variables were investigated so as to minimize residual alcohol and to yield a free-flowing homogeneous product. Residual alcohol in the desolventized flakes was 0.25–1.0%. Facility of removal followed the order—methanol, isopropyl alcohol, and ethanol. Two-stage flash desolventization as well as the use of the more dilute alcohols resulted in lower residual alcohol content of the desolventized product. After a minimum value for residual alcohol in the flakes is reached, further removal is difficult. However, water continues to be removed so that the alcohol water ratio becomes higher with an increased vaporization force as with increased temperature. It is postulated that the alcohol is held by adsorption or hydrogen bonding. The desolventized products analyzed: protein 72–77%; Nitrogen Solubility Index 4–16; water absorption values 328–410%. The products were light-colored, granular, and free flowing. The soybean flakes extracted with methanol exhibited the best flavor. A laboratory of the Northern Utilization Research and Development Division, U.S.D.A.     

Effect of moisture and temperature on the phosphorus content of crude soybean oil extracted from fine flour

Analysis of total oil content in soybeans is usually done by extracting flours, whereas commercial extraction for recovery of oil is done by extracting flakes. It has recently become apparent that phosphorus content of crude soybean oil extracted from flours can vary depending on extraction temperature and flour moisture. In this study, flour moistures below 6% yielded crude oil with low phosphorus (15 ppm), but phosphorus in the oil increased rapidly to 260 ppm at 9% moisture. When temperature of the extraction was increased from 25 to 60°C, the phosphorus in extracted oil also increased for moisture contents of 6.6% and 8.3%, but not for moisture contents of 5% and 3%. In addition to the effects of extraction temperature, it was found that preheating whole soybeans at various temperatures affected phosphorus in oil from extracted flour. Preheating at 130°C caused high phosphorus content regardless of how dry the flour was, whereas preheating at 100°C or below caused phosphorus content that increased with increased moisture. The response of phosphorus content in crude oil to temperature and moisture may be useful in improving the quality of commercially extracted soy oil.     

Surface Modification of Wood Using Nitric Acid

Surface modification of wood flakes by oxidation with nitric acid has been investigated at three different moisture contents of wood, and two different concentrations of the oxidant. It is shown that a significant number of the acid groups generated are chemically linked to wood. Increasing moisture content in wood has the effect of local dilution of the nitric acid oxidant while reduction in moisture content of wood during drying makes potential oxidation sites less accessible. Thus, two different regimes of oxidation, one of more accessible, and another, of less accessible, sites are observed. The nature of the generated acid is established as carboxylic, which is capable of undergoing a coupling reaction with 2-(l-aziridinyl)ethyl methacrylate. The catalysis of in situ polymerization of furfuryl alcohol by bound acid has also been shown to occur.     

Origin of the nonhydratable soybean phosphatides: Whole beans or extraction?

Whole soybeans and flakes, tempered to normal (10%) and elevated (14%) moisture levels, were stored and then extracted under a variety of conditions in both the presence or absence of phospholipase activity. Crude oils were degummed, and the resulting nonhydratable phosphatide (NHP) content was determined. Extractions performed on flakes at ambient temperature or at the boiling point of hexane showed that at normal (10%) moisture levels the temperature of extraction had little effect on the magnitude of NHP formation; whereas at 14% moisture, considerably higher levels of NHP were observed at the higher extraction temperature. Studies performed with 10- and 14%-moisture whole beans stored at 40°C for extended periods, with or without inactivation of enzymes, showed that at normal 10% moisture levels little deterioration occurs after one week of storage; however, after four weeks considerable NHP is formed. At 14% moisture, NHP formation was rapid during the first week of storage, and complete destruction of the phospholipid occurred after four weeks’ storage at 40°C. The results of these experiments indicate that the adverse effects of storage conditions, excessive moisture levels and elevated temperatures cannot be overcome by inactivation of phospholipase D prior to solvent extraction of the flakes.     

A new method of detoxification of cottonseed by means of mixed solvent extraction

For several decades, scientists in the field of vegetable oils tried unsuccessfully to detoxify cottonseed by a practical method. By using 20-30% (by wt) of ethyl alcohol (90% in vol) with commercial hexane as a mixed solvent, we were able to extract effectively both gossypol and oil from cottonseed prepressed cake or flakes. Free gossypol in meal was reduced to ca. 0.013-0.04%; total gossypol was reduced to 0.32-0.55%; residual oil was reduced to ca. 0.5% or less. Any aflatoxin present also can be eliminated by this process. The detoxified cottonseed meal can be used as animal feed. Cottonseed protein can be used to substitute for soy protein. The extracted oil is of better quality than that obtained by the usual hexane extraction method, and gossypol is a valuable byproduct.     

Phase equilibrium data pertaining to the extraction of cottonseed oil with ethanol and 2-propanol

Summary Basic phase relation data have been obtained relative to the extraction of cottonseed oil with ethanol and 2-propanol, especially as affected by water in the solvent. Mutual solubility diagrams have been constructed for cottonseed oil with ethanol and 2-propanol of various aqueous concentrations. Tie-line data at 30° C. have been obtained for the ternary ethanol-cotton-seed oil-water and 2-propanol-cottonseed oil-water systems. These combined data will be of assistance in the selection of the most desirable temperatures and moisture concentrations in the solvent extraction of cottonseed with these alcohols. Comparison with results previously published for soybean oil suggests that the mutual solubility data for cottonseed oil and aqueous ethanols are applicable to other vegetable oils over a wide range of iodine values. In general, the results indicate that 2-propanol is the more desirable solvent since complete miscibility with the oil can be attained at temperatures below its normal boiling point even at moisture contents as high as 10% by weight whereas ethanol can tolerate only about 1.5% of water. High moisture contents result in more effective separation of the oil from the solvent when the miscella is cooled after extraction. Constant boiling aqueous ethanol and 2-propanol present the disadvantage of requiring greater than atmospheric pressure during extraction in order to attain complete miscibility with the oil. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Factors affecting the content of tocopherol in soybean oil

The state of soybeans prior to extraction affected the tocopherol content of crude soybean oils. Soybean flakes with a thickness of 0.16–0.33 mm had higher extracted oil yield but a slightly lower tocopherol content of the oils than did cracked beans and thicker bean flakes. Highmoisture content and long storage of soybeans resulted in lower tocopherol content in the crude oils, with moisture content being more important than storage time at decreasing the tocopherol content of oils. Soybean oil from stored beans with 15±1% moisture content led to a more significant decrease in the tocopherol content than did oil from stored beans with low (12%) or high (18%) moisture contents. Soybean flakes contaminated with oxidized oil had a significant effect on the decrease of the tocopherol content in crude oils. The high amount of phospholipids in crude soybean oil might result in a smaller decrease in the tocopherol content of oil during heating.     

The Reduction of Glucosinolate and Sinapine Contents under Industrial Processing of Rapeseed

The glucosinolate and sinapine contents in industrially processed samples including seed, conditioned flakes, expeller press cake, solvent extracted meal and toasted meal of high glucosionlate (HG) and double low (DL) rapeseed were determined. Technological unit processes including flaking, conditioning, expeller pressing and solvent extraction had a little effect on the content of glucosinolate (with exception of DL when one-fifth of glucosionolate was lost) and sinapine contents while toasting stage reduced contents of both compounds by 62 to 74% of original level in the seeds. Overall industrial process reduced glucosinolate content by 64 to 79% of seed value in HG and DL rapeseed, respectively, whereas sinapine was decreased by 26% in both types of rapeseed.     

Polymers with upper critical solution temperature behavior in alcohol/water solvent mixtures

Thermoresponsive polymers are of great importance in numerous nanotechnological and biomedical applications. Compared to polymers that undergo a lower critical solution temperature (LCST) phase transition in aqueous solution, i.e., demixing occurs upon heating, polymers exhibiting the reversed upper critical solution temperature (UCST) behavior in aqueous solution have been much less documented as it is more challenging to achieve this behavior in aqueous solutions. Furthermore, the high sensitivity of UCST behavior to minor variation in polymer structure and solution composition hampered the development of applications based on these polymers [18]. However, polymers with UCST transition in alcohol/water solvent mixtures are more commonly reported and exhibit promising properties for the preparation of ‘smart’ materials. This review will focus on the theory and development of such polymers with UCST behavior in alcohol/water solvent mixtures. By highlighting reported examples of UCST polymers in alcohol/water solvent mixtures, we aim to demonstrate the versatility and potential that such UCST polymers possess as biomedical and ‘smart’ materials.     

Surface Modification of Wood Using Nitric Acid

Surface modification of wood flakes by oxidation with nitric acid has been investigated at three different moisture contents of wood, and two different concentrations of the oxidant. It is shown that a significant number of the acid groups generated are chemically linked to wood. Increasing moisture content in wood has the effect of local dilution of the nitric acid oxidant while reduction in moisture content of wood during drying makes potential oxidation sites less accessible. Thus, two different regimes of oxidation, one of more accessible, and another, of less accessible, sites are observed. The nature of the generated acid is established as carboxylic, which is capable of undergoing a coupling reaction with 2-(l-aziridinyl)ethyl methacrylate. The catalysis of in situ polymerization of furfuryl alcohol by bound acid has also been shown to occur.     

Physicochemical characterization of poly(ethylene glycol) plasticized poly(methyl vinyl ether‐co‐maleic acid) films

The influence of the poly(ethylene glycol) (PEG) plasticizer content and molecular weight on the physicochemical properties of films cast from aqueous blends of poly(methyl vinyl ether‐co‐maleic acid) (PMVE/MA) was investigated with tensile mechanical testing, thermal analysis, and attenuated total reflectance/Fourier transform infrared spectroscopy. Unplasticized films and those containing high copolymer contents were very difficult to handle and proved difficult to test. PEG with a molecular weight of 200 Da was the most efficient plasticizer. However, films cast from aqueous blends containing 10% (w/w) PMVE/MA and either PEG 1000 or PEG 10,000 when the copolymer/plasticizer ratio was 4 : 3 and those cast from aqueous blends containing 15% (w/w) PMVE/MA and either PEG 1000 or PEG 10,000 when the copolymer/plasticizer ratio was 2 : 1 possessed mechanical properties most closely mimicking those of a formulation we have used clinically in photodynamic therapy. Importantly, we found previously that films cast from aqueous blends containing 10% (w/w) PMVE/MA performed rather poorly in the clinical setting, where uptake of moisture from patients' skin led to reversion of the formulation to a thick gel. Consequently, we are now investigating films cast from aqueous blends containing 15% (w/w) PMVE/MA and either PEG 1000 or PEG 10,000, where the copolymer/plasticizer ratio is 2 : 1, as possible Food and Drug Administration approved replacements for our current formulation, which must currently be used only on a named patient basis as its plasticizer, tripropylene glycol methyl ether, is not currently available in pharmaceutical grade. © 2009 Wiley Periodicals, Inc. J Appl Polym Sci, 2009     

An investivation of the extraction,refining and composition of oil from winged bean (Psophocarpus tetragonolobus [L.] D.C.)

Eleven winged bean accessions from Thailand were analyzed. Oil content ranged between 15 and 18%. Oleic and linoleic acids were the major fatty acids (62.5–64.5%) together with behenic (12.6–14.4%) and lignoceric acid (2.4–2.8%). Linolenic acid level was low and traces of 15-, 17- and 21-carbon acids (saturated and unsaturated) were found. No parinaric acid was detected. Campesterol, stigmasterol and β-sitosterol were the principal components of the unsaponifiable fraction. The extracted oil had a very low free fatty acid (FFA) content but was not completely liquid below 35 C. The refining of crude winged bean oil is reported. Oil produced by expeller had a strong, beany aroma but a negligible level of gums and a low level of FFA. Degumming and neutralizing were unnecessary; bleaching produced an attractive colored oil free from beany aroma. Crude solvent-extracted oils from whole and decorticated winged beans had appreciable contents of gums and higher FFA contents than expeller-produced oil. Laboratory refining demonstrated the strong interference on bleaching exerted by gums and FFA. Conventional refining by degumming, neutralizing, bleaching and deodorizing, and by physical refining produced high-quality oils having a good color, low FFA level and no taste or smell. The solid/liquid ratio of refined winged bean oil as a function of temperature was found to be unusual. Oil was extracted from whole and decorticated winged beans in a pilot solvent extraction plant designed to simulate a Rotocei. Winged bean flakes were not as mechanically strong as those from soybean but good oil extraction yields were obtained and a meal was produced having an oil content of less than 1% at 10% moisture. Whole winged beans were expelled in a small expeller (throughput 16.8 kg/hr). Cake was produced with a residual oil content of 3.3–5% in a single pass through the expeller.     

Flaking as a Pretreatment for Enzyme-Assisted Aqueous Extraction Processing of Soybeans

Soybean moisture content (7.2–12.8%) and conditioning temperature (51–79 °C) during flaking were evaluated to determine their effects on oil and protein extraction and oil distribution among fractions produced in enzyme-assisted aqueous extraction processing (EAEP). Extractions were performed by using two-stage countercurrent EAEP at a 1:6 solids-to-liquid ratio with 0.5% protease (wt/g extruded flakes) at pH 9.0 and 50 °C for 1 h. Oil extraction improved when using soybeans with moisture contents ranging from 8.0 to 12.0% for flaking but was not affected by conditioning temperature. Oil extraction was reduced when moving away from 10% moisture with the lowest values at 7.2 and 12.8% moisture. Free oil extraction increased as soybean moisture content increased from 7.2 to 12.8% although total oil extraction was reduced at 12.8% moisture. Higher (79 °C) and lower conditioning temperatures (51 °C) improved free oil extraction and reduced cream emulsion formation. Skim oil content was not significantly affected by soybean moisture content and the conditioning temperature, although an undesirable high oil content in the skim was observed at 8% moisture and at 55 °C. The cream with a high oil yield was easily demulsified compared with cream containing a low oil yield (95 vs. 76.5% de-emulsification). Due to differences in cream stability, similar oil recoveries (78–80%) were obtained for treatments yielding creams with either low or high oil yields. Mean protein extraction of 95% was achieved for all treatments and was not significantly affected by soybean moisture content at flaking or conditioning temperature.     

Erratum

Abstract

Southern pine and aspen flakes were acetylated with acetic anhydride alone without cosolvent or catalyst by a simple dip procedure. The new procedure greatly shortens reaction time and simplifies chemical recovery. Acetylation weight gains of 15% to 20% can be achieved in 1 to 3 hours with southern pine flakes and in 2 to 4 hours with aspen flakes.

Flakeboards made from acetylated southern pine or aspen flakes absorbed much less water, both in water-soaking tests and when subjected to humid air, and swelled at a lower rate and to a lower extent than did control boards.

Hygroscopicity of the resulting flakeboards decreased with increased level of wood acetylation. The equilibrium moisture content (EMC) for flakeboards made from acetylated flakes was lower at each relative humidity tested than that of control boards.     

Factors promoting the formation of nonhydratable soybean phosphatides

Whole, cracked and flaked soybeans were stored under a variety of conditions. After extraction with hexane, the crude oils were degummed in the laboratory, and the nonhydratable phospholipid (NHP) content was estimated from the phosphorus content of the degummed oil. Results showed that four interrelated factors promote NHP formation. These include (i) moisture content of beans or flakes entering the extraction process; (ii) phospholipase D activity; (iii) heat applied to beans or flakes prior to, and during, extraction; (iv) disruption of the cellular structure by cracking and/or flaking. Results from this study suggest that NHP formation can be minimized by control of the moisture of beans and/or flakes entering the extraction process, inactivation of phospholipase D enzyme, and optimizing temperatures during the conditioning of cracked beans or flakes. Presented at the 82nd Annual Meeting of the American Oil Chemists’ Society, Chicago, IL, May 12–16, 1991.     

Extraction of oil from meadowfoam flakes

As part of a program to improve meadowfoam seed processing, the authors examined the effects of seed moisture, seed temperature, and flaking roll opening on oil extraction efficiency in meadowfoam flakes. Flakes were prepared using a Wolf Mill with dual horizontal, unheated 12-in. diameter rolls. Roll openings of 0.005, 0.013, and 0.020 in. (0.127, 0.330, and 0.508 mm, respectively) gave average flake thicknesses of 0.013, 0.021, and 0.031 in., respectively (0.330, 0.533, and 0.787 mm). Seed moistures of 9, 12, and 15% and seed temperatures of 65, 190, and 210°F (18, 88, and 99°C) chosen for flaking were known to provide a range of conditions suitable for enzyme inactivation during seed cooking prior to flaking. Experimental flakes were examined for extractable oil content (petroleum ether extraction); this was compared to total oil content (31.5%) determined on finely ground flakes. Roll opening was the dominant variable determining flake thickness, the primary parameter affecting oil extraction efficiency. Thus, the thinnest flakes at 0.013 in. were only slightly less extractable (29.8%) than finely ground flakes (31.5%), but intermediate (0.021 in.) and thick (0.031 in.) flakes were significantly less extractable (28.0 and 26.0%, respectively). There was a slight but significant (P<0.01) trend toward thicker flakes with increasing seed moisture (15>12>9%) during flaking. A similar trend to thicker flakes with increasing temperature was significant (P<0.01) only for the thickest flakes produced at the largest roll opening (0.020 in.). Lower seed moisture and higher seed temperature significantly impacted extractable oil content of the thickest flakes, but negligibly affected extractability of the thinnest flakes. The authors conclude that meadowfoam flakes must be as thin as possible (e.g., <0.015 in.) for efficient oil extraction. Further, seed cooking temperatures >190°F at moistures >10% and <15% that are adequate for efficient enzyme inactivation in the whole seed are also suitable for seed flaking.