Grapefruit seed oil sterols

Grapefruit seed oil sterols separated from other lipids by Florisil column chromatography were characterized by gas liquid chromatography. The presence of stigmasterol, campesterol and β-sitosterol is indicated. Expressed in terms of peak area, the three sterols are present in proportions of 2.5%, 7.4% and 90.1% of the total, respectively.     

Composition of tall oil pitch

Compositions of six grades of tall oil pitch (TOP), four of finnish and two of U.S. origin were investigated. The pitch samples contained 34.6–51.6% free acids, 23.2–37.8% esterified acids, and 25.3–34.4% unsaponifiable neutral compounds. Each of the above fractions was analyzed by high resolution gas chromatography-mass spectrometry. Approximately 60% of the weight fraction in TOP consisted of high molecular components of which about half were acidic compounds. The low molecular free acids were mainly dehydroabietic, abietic, and other resin acids. The esterified acids consisted chiefly of oleic and linoleic acids. Unsaponifiable fractions were composed of diterpene alcohols, fatty alcohols, sterols, and dehydrated sterols. The alcohol components were almost completely esterified.     

Refining of tall oil pitch

Six grades of tall oil pitch (TOP) were subjected to extraction by n-hexane and subsequent adsorption by SiO₂-activated carbon blend. Treated pitch samples contained 32.9–48.4% free acids, 24.2–35.0% esterified acids, and 25.0–36% unsaponifiable neutral compounds. Each of the above fractions was analyzed by high resolution gas chromatography. The portion insoluble in n-hexane contained 83.9% free acids, 10.6% esterified acids, and 5.5% unsaponifiable neutral compounds, indicating enrichment of the acidic compounds in this fraction. The decolorizing effect was observed in all treated TOP grades.     

Amide plasticizers from safflower and tall oil derived fatty acids

Fatty acids derived from a high oleic strain of safflower seeds are eminently suited for the preparation of compatible and efficient N,N-disubstituted fatty acid amide polyvinyl chloride plasticizers with low temperature properties in the adipate-azelate range. N,N-disubstituted amides of tall oil-derived acids, Westvaco Type 1480, give comparable plasticizing performance. Polyvinyl chloride compositions plasticized with the hexachlorocyclopentadiene adduct of N,N-dibutyloleamide show no soapy water extraction loss. So. Market. Nutr. Res. Div., ARS, USDA.     

Neutrals in southern pine tall oil

Journal of the American Oil Chemists' Society - Black-liquor soap skimmings from commercial pulping of southern pine wood contained 4.8% neutrals by wt. The neutrals were quantitatively...     

Unusual resin acids in tall oil

Combinations of silver nitrate column, gel permeation and gas liquid chromatography were used to isolate 8,15-pimaradien-18-oic, 8,15-isopimaradien-18-oic and the secodehydroabietic, 2α-[2′(m-isopropylphenyl)ethyl]1β,3α-dimethylcyclohexanecarboxylic acids as their methyl esters from a fraction of distilled tall oil. Presented before the Division of Cellulose, Word and Fiber Chemistry at the 155th National Meeting of the American Chemical Society, San Francisco, April 1968.     

妥尔油精馏及其开发利用

介绍了纸浆废液中回收的妥尔油的性质、生产和分离，以及分离产品妥尔油脂肪酸、妥尔油松香和妥尔油沥青的开发利用。     

Distillability of extracted mixed-birch tall oil

Chemical and physical properties of tall oil made in the CSR process and distillation results of three different types of distillation plants are presented. Chemically extracted, mixed-birch, tall oil differs remarkably from the normal Scandinavian crude tall oil. The extracted oil deviates from the normal, unextracted, mixed-birch tall oil with respect to the smaller unsaponifiable amount and the fatty acid esters. The amount of resin acid is small in extracted mixed-birch tall oil. The quantity of fatty acids, especially that of saturated fatty acids, is large. Distillation of extracted mixed-birch tall oil is most successful in a distillation plant where thin film evaporators are used.     

Concentration of sterols and tocopherols from olive oil with supercritical carbon dioxide

A process based on the use of a semicontinuous countercurrent supercritical fluid extraction has been developed to isolate and concentrate minor compounds, such as sterols and tocopherols, from olive oil. In the present work, an evaluation of the efficiency of different random packing materials (Raschig rings, Dixon rings, Fenske rings, and glass beads) to selectively separate sterols and tocopherols from olive oil has been performed. Parameters such as recovery, enrichment, and selectivity vs. TG are discussed. Considering the importance of supercritical fluid extraction as a clean processing technology and the interest in minor compounds with nutraceutical properties from olive oil, the process studied represents an alternative to the reuse of low-quality olive oil to extract high added-value products.     

Methods of analysis for tall oil products

Summary The principal standard methods used by the American industry for the analysis and quality control of tall oil products have been discussed, and some of the work of the A.S.T.M. in developing these methods has been reviewed. Further growth of the tall oil industry will undoubtedly result in new products of greater refinement and wider utilization. New and improved methods of analysis will be required. These can be worked out by the industry in continued collaborative work under the auspices of the A.S.T.M. and A.O.C.S. Undoubtedly instrumental test methods such as infrared and ultraviolet spectroscopy and gas chromatography will play a role of increasing importance in the analysis of tall oil products.     

Continuous acidulation process for tall oil production

Summary The conventional batch process for tall oil production was changed to a semicontinuous one by properly sizing tanks to reaction times and adding a screen and a continuous centrifugation step. As a further improvement an entirely new, continuous acidulation process has been developed which includes proportioning of reagents, controlled mixng, and degasification, followed by tall oil separation in a special form of nozzle type of centrifuge. Both these processes produce higher quality tall oil at lower cost than the original batch process. The economy of the process has been improved by modifying the centrifuge to remove fibers, which eliminates a costly and troublesome screening step. Lowest costs are produced by a plast specifically designed to use waste acid from a chlorine dioxide bleaching process. Presented at the Spring Meeting, American Oil Chemists' Society, Memphis, Tenn., April 21–23, 1958.     

Separation of fatty acid methyl esters from tall oil by selective adsorption

Fatty acid methyl esters (FAME) and resin acids (RA) were separated from tall oil by selective adsorption. Commercial nonmodified molecular sieve 13X was used as adsorbent. The adsorption isotherms of fatty acids (FA), FAME, and RA on molecular sieve 13X at 25°C were determined using various solvents. The solvents were methanol, ethanol, isopropanol, acetone, benzene, hexane, isooctane, petroleum ether (40–60°C), and petroleum naphtha (80–180°C). With each solvent, FA and RA were adsorbed to a greater extent than FAME. Adsorption isotherms for RA and FAME in binary adsorption systems were also determined using petroleum ether, petroleum naphtha, benzene, and isopropanol. For each component in the binary adsorption, the equilibrium amounts are lower than the values for pure component adsorption. The adsorption of FAME decreased in the presence of RA markedly in petroleum ether and petroleum naphtha. This fact may be the indication of the phenomenon of selective adsorption. Separation was accomplished by adding a solution of esterified tall oil in solvents used in the binary adsorption systems, through a column packed with molecular sieve 13X. With petroleum naphtha, FAME and RA were recovered in yields of 93 and 94%, respectively, from esterified tall oil. Petroleum naphtha gave the best results. The effects of particle size of adsorbent and flow rate of solvent on the efficiency of the separation were also investigated in fixed-bed column studies. The particle size of adsorbent did not apparently alter the results. Changes in the particle size should not significantly change the number of available adsorption sites in a microporous molecular sieve.     

Characterization of products from clay catalyzed polymerization of tall oil fatty acids

Products obtained by acid clay catalyzed dimerization of oleic, elaidic, and tall oil fatty acids were characterized. The monomeric products (35% of total) consisted of stearic, octadecenoic (66%trans-), and mid chain monomethyl branched acids, both saturated and unsaturated. The polymeric products (65% of total) consisted of linear, alicyclic, aromatic, and polycyclic dimers. The tall oil fatty acid based dimer closely resembled oleic dimer in polycyclic character and linoleic dimer in aromatic and linear structures. Oleic dimers contained the highest linear structural content, while linoleic dimer contained the largest polycyclic content. Alicyclic structures were the principal components of all three products. The monocyclic dimer structures present consisted of six membered ring systems with linoleic and tall oil fatty acid dimers containing the highest aromatic contents. Presented at the National American Chemical Society Meeting, New York, August 1972.     

The fat acids of American tall oil

Summary The composition of the fat acids of six samples of American tall oil has been determined. They are all quite similar in fat acid composition. The average values were: linoleic acid 48%; oleic acid 45%; saturated acids 7%. There is present approximately 11% of conjugated linoleic acid, probably formed by the action of alkali and heat during the cooking of the pulp from which the tall oil was formed. Detailed fractional distillation of a sample of the methyl esters of the fat acids showed that the saturated acids are mostly palmitic, that there may be about 1% of palmitoleic, and that the conjugated linoleic acid present can be separated and concentrated by fractional distillation. Paper No. 65, Journal Series, Research Department, General Mills, Inc.     

Spectrophotometric analysis of tall oil rosin acids

Summary About half of the rosin acids in whole and distilled tall oil consist of abietic and neoabietic acids, as distinguished from hydroabietic acids, dehydroabietic acid, and the pimaric acids. In this respect the tall oil rosin acids are similar to those from gum or wood rosin. This was established by spectrophotometric analysis of the rosin acids from whole tall oil, double distilled tall oil, rosin acids crystallized from tall oil, and rosin acids separated from tall oil by fractional distillation. The rosin acids crystallized from tall oil contained the highest percentage of abietic acid, but the sum of abietic and neoabietic acids was only slightly higher. The rosin acids from acid refined tall oil contained appreciably less abietic and neoabietic acid than the others. Before spectrophotometric analysis the rosin acids were isolated from the tall oils in about 95% yield by cyclohexylamine precipitation.     

Triterpene alcohols and sterols of Spanish olive oil

Nine Spanish olive oils, including three each of virgin (pressed oil), refined virgin, and B-residue (solvent-extracted pomace oil) oils from different commercial sources, have been analyzed for their unsaponifiable matter (USM). Four sterolic fractions separated from the oils have been analyzed by preparative thin-layer chromatography (TLC); these fractions are triterpene alcohols, 4-methylsterols, sterols and triterpene dialcohols. The compositions of the four sterolic fractions were determined as their acetates by gas-liquid chromatography (GLC) on an OV-17 glass capillary column. Identification of each component was carried out by argentation TLC, GLC and combined gas chromatography-mass spectrometry (GC-MS); 44 components were identified, of which four: 24-methylene-31-nor-9(11)-lanostenol, 24-methyl-31-nor-E-23-dehydrocycloartanol, 24-ethyl-E-23-dehydrolophenol and 5,E-23-stigmastadienol, were considered to be new sterols from natural sources. Several characteristics, including the content of triteterpene dialcohols in the USM and that of C-24(28) unsaturated sterols in each of the four sterolic fractions, which can be used to distinguish between virgin and B-residue olive oils, were observed.     

Origin of bicyclic fatty acids in tall oil

It was shown that two bicyclic fatty acids present in Finnish tall oil were formed from (5Z, 9Z, 12Z)-5, 9, 12-octadecatrienoic acid, pinolenic acid (I). Under the alkaline conditions of sulfate pulping, pinolenic acid forms conjugated isomers which undergo Diels-Alder cyclization during the heating in the tall oil distillation. The cyclization products, here called cyclopinolenic acids, are bicyclic fatty acids and stereoisomers of 4-(5-pentyl-3a, 4,5,7a-tetrahydro-4-indanyl) butanoic acid (IV and V).