Accumulation of cardiac fatty acids in rats fed synthesized oils containing C22 fatty acids

Synthesized oils containing a high proportion of oleic, eicosenoic or docosenoic acid were fed to weanling rats as 20% w/w of the diet. After 1 week, a high intake of eicosenoate produced cardiac fat droplets detected histologically, whereas erucate (22∶1 Δ 13) or cetoleate (22∶1 Δ 11) caused an appreciably greater accumulation of cardiac lipid characterized by the dietary fatty acids.     

Cytocompatible polyurethanes from fatty acids through covalent immobilization of collagen

Two different polyurethanes synthesized from two triols derived from undecenoic acid (PU1) and oleic acid (PU2) fatty acids were functionalised with Collagen type I via plasma treatment aimed at obtaining novel biomaterials with improved biological properties. Scanning Electron Microscopy, X-ray photoelectron spectroscopy, optical microscopy, colorimetric titration methods and contact angle measurements confirmed the surface changes at each stage of treatment, both in terms of morphology and chemical composition. The results for osteoblastic cells (MG63) cultured in vitro proved that PUs modified with collagen had better cytocompatibility that the control PUs. In particular, PU2 displays higher cytocompatibility.     

Production of fatty alcohols from fatty acids

Detergent-range alcohols from natural feedstock can be produced by high pressure hydrogenation of either methyl esters or fatty acids. The increasing quantities of fats and oils on the world market secure a reliable and economically priced material. Although fatty acid is an abundant worldwide commodity, most alcohol producers hydrogenate methyl esters, because direct hydrogenation of fatty acids is difficult as the catalyst is sensitive to acid attack. The process described here makes it possible to hydrogenate fatty acids directly to alcohols of high quality without prior esterification. The reaction takes place in the liquid phase over a fine-grained copper chromite slurry in a single reactor vessel. A special reactor design with an optimum arragement of the feeding nozzles causing an appropriate circulation of the reacting components inside the reactor facilitates the rapid “in situ” esterification reaction. This minimizes the free fatty acid concentration in the reactor to nearly zero. This results in a low consumption of catalyst. The most important advantages of the process are: direct feed of fatty acids of various origins, use of reasonably priced raw materials such as soapstock fatty acids and lower grade tallow acids, no process steps with methanol, and excellent economics. The process is industrially proven.     

Extracting long-chain fatty acids from a fermentation medium

Several solvents were evaluated for extracting free long-chain FA (LCFA) from a fermentation medium. Chloroform, chloroform/methanol (1∶1), hexane, and hexane/methyl tert-butyl ether (MTBE) (1∶1) were evaluated as alternative extraction solvents. Parameters considered for optimizing LCFA recoveries included pH and ionic strength. Maximal LCFA recoveries were obtained by adding 2 mL of the hexane/MTBE (1∶1) solvent mixture, 80 μL of 50% H₂SO₄, and 0.05 g NaCl to 1 mL of the aqueous sample and mixing for 15 min at 200 rpm. This method quantified saturated LCFA [capric acid (C_10∶0) to stearic acid (C_18∶0)] and unsaturated LCFA with 18 carbons [linoleic acid (C_18∶2) and oleic acid (C_18∶1)] with a 98 to 100% recovery. Caproic (C_6∶0) and caprylic (C_8∶0) acids were characterized by 27 and 76% recoveries, respectively.     

Estolides from meadowfoam oil fatty acids and other monounsaturated fatty acids

The formation of estolides was detected during the studies on dimerization of meadowfoam oil fatty acids. By adjusting the reaction conditions, it was possible to produce monoestolides with little dimer or trimer formations. Estolides have potential use in lubricant, cosmetic and ink formulations and in plasticizers. This paper reports the conditions for production of estolides from mixed meadow-foam fatty acids, commercial oleic acid, high-oleic sun-flower oil fatty acids,cis-5,cis-13-docosadienoic acid, petroselinic acid and linoleic acid.     

Cyclic fatty acids: Separation from straight-chain fatty acids by urea adducting

A mixture containing 37% cyclic and 63% straight-chain fatty acids, made by high-temperature treatment of linseed oil fatty acids with alkali, was separated by the urea adduct method to give unsaturated cyclic fatty acids (nonadduct) in 95% purity and 90–95% yeild. Previous reports from this Laboratory describe a process for separating cyclic fatty acids from stearic acid by hydrogenation followed by crystallization at −40C. The urea adduct method avoids hydrogenation and low-temperature crystallization, and furthermore, unsaturated cyclic and unsaturated straight-chain products can be recovered as individual fractions. Then, by readducting the unsaturated straight-chain fatty acid fraction, the small amounts of palmitic and stearic acids are removed leaving an unsaturated fraction containing oleic, nonconjugated and conjugated linoleic and some unsaturated cyclic fatty acids. Presented at AOCS Meeting, Los Angeles, April 1966. No. Utiliz. Res. Dev. Div., ARS, USDA.     

Historical and marketing trends of natural/synthetic fatty acids

As long as a substantial portion of raw materials for natural fatty acids are relatively inexpensive by-products of other major industries, natural fatty acids should fulfill the world's projected needs at least through 1985. Production of synthetic fatty acids may also increase; however, at the present time the cost of their raw material and processing has made them largely noncompetitive, except in a few cases. Synthetic organic acid manufacturers currently supplying short chain products will continue their efforts to enter the detergent range fatty acid market area. We expect some breakthrough in synthetics during the life of our forecast. However, potential producers have yet to develop an economically competitive synthetic fatty acid as a replacement for natural fatty acids in the U.S. Petroleum-based products include odd, even, and branched chain acids whose performance must be proven. Finally, the petroleum base for synthetic fatty acids no longer has the price stability we have been accustomed to in the past. Recent changes in price of ethylene and forecasts are evidence of this trends for the future.     

Separation of natural polyunsaturated fatty acids by means of lodolactonization

Conditions of the iodolactonization reaction (ILreaction) were optimized as a method for separation of natural polyunsaturated fatty acids. The effects of the solvent, temperature and the ratio of components of the iodizing complex KI/I₂ upon the rate of the synthesis of several iodolactones (ILs) in the IL-reaction are described. It was shown that the rate of formation of γ-ILs was significantly higher than that for δ-ILs. This offers opportunity for obtaining pure docosahexaenoic acid (DHA) from fatty acid (FA) concentrates. The possibility for selective reduction of δ-ILs in the presence of γ-ILs to yield pure arachidonic acid (AA) or eicosapentaenoic acid (EPA) or fatty acid concentrates has been demonstrated. Preparation of pure AA from a mixture of AA, DHA and other FAs by the IL-reaction without Chromatographie procedures is described.     

Epoxidation of modified natural plasticizer obtained from rice fatty acids and application on polyvinylchloride films

In recent years, much research effort has been driven to develop alternative plasticizers for medical and commodity plastic materials. In this study, a modified natural plasticizer, synthesized by esterification of rice fatty acids, was modified by epoxidation with peroxy acid generated in situ. Two natural epoxidized plasticizers were obtained, using peracetic acid (NP‐Ac) and peroctanoic acid (NP‐Oc) as reagent. PVC films after addition of these natural epoxidized plasticizers presented fairly good incorporation and plasticizing performance, as demonstrated by results of mechanical properties, T_g values (as shown by DSC), optical microscopy, exudation, and migration tests, FTIR and X‐ray diffraction obtained for plasticized PVC films. NP‐Ac plasticizer presented enhanced plasticizing performance compared with NP‐Oc, probably due to a higher epoxidation degree obtained in the reaction with peracetic acid. © 2012 Wiley Periodicals, Inc. J. Appl. Polym. Sci., 2013     

New fatty acids from outer space

A recent space exploration has revealed that in the far reaches of outer space matter attains a state of complete weightlessness. Herman Brown, reporting on his latest spaced-out venture, indicates that weightless fatty acids obtained from the Superba Galaxy are ideally suited for the manufacture of improved food additives. What a magnificent way to provide the diet-control foodstuffs of the 21st Century!     

Antimicrobial agents derived from fatty acids

The author reviews his research, since 1966, for the ideal germicide. The relationship between structure of fatty acids, their corresponding esters, and antimicrobial activity is presented. Saturated fatty acids have their highest activity when the chain length is twelve carbons (C₁₂) long; monounsaturated fatty acids reach their peak with palmitoleic acid (C_16∶1); the most active polyunsaturated fatty acid is linoleic.Trans isomers are not active against microorganisms. The esterification of fatty acids to monohydric alcohols leads to inactive derivatives, whereas esterification to polyhydric alcohols increases biological activity. Examples of glycerol and sucrose esters are reviewed. In general, the lauroyl derivatives are the most active. A few examples of esters as active pharmacological agents against organisms causing bovine mastitis are presented as well as the use of monolaurin (Lauricidin^®) as cosmetic and food preservatives. The safety and efficacy of fatty acid esters as potential germicides offer new and expanded roles for oleochemicals.     

Cyclic fatty acids from linolenic acid

Linolenic acid of 95% purity was heated with excess alkali in ethylene glycol to produce cyclic fatty acids. Reaction variables, which are associated with the cyclization reaction and which were investigated, included solvent-to-fatty-acid ratio, catalyst concentration, and reaction temperature, headspace gas (N₂ or C₂H₄), and head-space gas pressure. Yields of cyclic acids were improved by increasing solvent ratio (1.5–6 wt basis), reaction temperature (225–295C), and catalyst concentration (10–100% excess). With nitrogen the optimum catalyst concentration was about 100% excess, but when ethylene was used, no increase was obtained beyond 50% excess catalyst. Yields of polymeric acids produced in the reaction generally decreased as cyclic acid yields increased, except in one instance. Higher yields of cyclic fatty acids were obtained with ethylene than with nitrogen under all comparable conditions, and increasing the ethylene pressure to as high as 500 psi improved the yield. Ethylene adds to the conjugated double bonds and is believed to give C₂₀ fatty acids having a 1,4-disubstituted monoene ring in the chain. The maximum yield of monomeric cyclic acids from 95% linolenic acid was 84.6%, the balance being polymeric and unreacted monomeric acids. Monomeric acids from this test contained 95% cyclic acids. Presented at AOCS meeting, New Orleans, 1962. No. Utiliz. Res. & Dev. Div., ARS, U.S.D.A.     

Manufacture of soap from fatty acids

Soap manufacture from fatty acids is a well established precess with some advantages over continuous saponification of neutral fats. These include:

1. Ability to use cheaper fats.
2. Easier glycerol recovery.
3. Better control over by-products.
4. Versatility-fatty acids can be used to make other derivatives than soaps.

     

Furanoid fatty acids from fish lipids

Fatty acids, recently reported as constitutents of certain fish lipids, were identified to be derivatives of furan (furanoid fish fatty acids). 12,15-Epoxy-13,14-dimethyleicosa-12,14-dienoic acid is predominant among the furan acids and is associated withbis-homologs in regard to chain length. Monomethyl acids, such as 12,15-epoxy-13-methyleicosa-12,14-dienoic, are present in appreciable amounts. The structures were concluded from oxidative degradations, from mass spectrometry of methyl esters of the novel acids and fatty acids derived from them by opening the ring, and from nuclear magnetic resonance, infrared, and Raman spectra. The results from chemical procedures and from spectrometric methods were in aggreement with those obtained with authentic methyl 9,12-epoxyoctadeca-9,11-dienoate. The number of substituents at the furan ring greatly influences hydrogenation, hydrogenolysis, and hydrolysis reactions of the ring. Scientific Journal Series 9154, Agricultural Experiment Station, University of Minnesota, St. Paul, MN 55101; Hormel Institute Publication No. 749.     

Gelcasting of alumina with a new monomer synthesized from glucose

Synthesis of a new low-toxic monomer obtained from glucose is reported and its application in gelcasting process is presented. The new monomer named 3-O-acrylic-d-glucose is an interesting alternative for the commercially available acrylic monomers. The presence of many hydroxyl groups in the monomer molecule allows to create hydrogen bonds in the polymer network. The resulting network does not need any external cross-linking agent to obtain a rigid ceramic part. The present paper describes the properties of ceramic slurries, green and sintered elements obtained from two alumina powders of different grain size (0.21 μm and 0.70 μm) with the use of the new monomer 3-O-acrylic-d-glucose and commercially available 2-hydroxyethyl acrylate.     

Solvent extraction of fatty acids from natural oils with liquid water at elevated temperatures and pressures

The use of liquid water at elevated temperatures and pressures as an extractive solvent for separating mixtures of compounds which occur in natural oils has been studied. A southern pine tall oil and a distillate from the deodorization of soybean oil were extracted with liquid water at temperatures from 298 to 312°C and pressures between 103 and 121 bar. Results indicate that water can be used to extract fatty and resin acids from crude tall oil to obtain a product with a high acid content that produces less pitch during distillation. The process can also be used to extract fatty acids from vegetable oil deodorizer distillate.     

Some proposals toward a new system of oral nomenclature for long-chain fatty acids

Proposals toward a new system of oral nomenclature for long-chain fatty acids and their derivatives are presented. The nomenclature suggested is, in general, merely a simplification of classical Geneva nomenelature, and it is hoped that its acceptance and utilization will result in a reduction in the use of meaningless, trivial names in oral presentation. Presented at the 34th fall meeting, American Oil Chemists’ Society, New York, October 16–19, 1960. Supported in part by the Hormel Foundation.     

Identification of novel octadecadienoic fatty acids in the seaweedCladophora rupestris through oxidative ozonolysis of the alcohols prepared from the acids

The BF₃−MeOH reagent for ozonolysis of ethylenic unsaturation does not oxidize alcohols. It is therefore feasible to determine the position of ethylenic unsaturation in long chain fatty alcohols of synthetic or natural origin by recovering the methyl ester products intact and silylating the alcohol function of half-ester, half-alcohol, products prior to gas liquid chromatographic analysis. The C₃ fragment from methylene-interrupted alkyl chains is not recovered, but, by first reducing carboxyl ester groups to alcohols, the terminal difunctional products can be identified in nonmethylene-interrupted dienoic fatty acids. The seaweedCladophora rupestris is shown to contain Δ5,Δ11-,Δ8,Δ11-, and Δ11, Δ14- as well as Δ9,Δ12-octadecadienoic acid.     

Preparation of alcohols from cyclic fatty acids

Saturated C_18- and C₂₀-cyclic alcohols have been prepared by catalytic hydrogenation of methyl esters from cyclized linseed monomeric acids, purified saturated C₁₈-cyclic acids, ethylene adduct of conjugated soybean fatty acids, and ethylene adduct of conjugated octadecadienoic acids. The cyclic alcohols have also been prepared from free acids of crude cyclic linseed, cyclic linseed monomeric, and ethylene adduct of 9,11,t,t,-octadecadienoic. Conversion of esters and acids was 88–99% by hydroxyl determination; by gas-liquid chromatographic analysis, almost quantitative Hydrogenations were carried out with 10%, by weight, copper chromite catalyst, an initial hydrogen pressure of 2,100 psi, and a temperature of 280C for 3–5 hr. Preliminary evaluations indicate that saturated C_18- and C₂₀-cyclic alcohols have a potential use in cosmetic formulations. Presented AOCS meeting in Minneapolis, Minn., 1963. No. Utiliz. Res. & Dev. Div., ARS, USDA.     

Diels-Alder adducts from safflower oil fatty acids

Methyl esters of alkali-isomerized safflower oil fatty acids after elaidinization with sulfur were treated with styrene in the presence of hydroquinone, with or without solvents. A combination of column chromatography and gas liquid chromatography techniques was employed for the estimation of the methyl esters of unreacted fatty acids, Diels-Alder adduct and polymers in the reaction products. Maximum yield of the Diels-Alder adduct (26.6%) was obtained when the elaidinized methyl esters of the fatty acids were treated with 1.5 moles of styrene per mole of linoleic acid in safflower oil fatty acids at 200–210 C for 6 hr. The methyl ester of the adduct was isolated in about 90% purity from the reaction product by vacuum distillation followed by solvent fractionation. The butyl ester of the adduct and the epoxy derivative of the methyl ester adduct were prepared and characterized.