Search for new industrial oils. VI. Seed oils of the genusLesquerella

Fatty acid composition of seed oil from 14 species of the genusLesquerella has been determined by gas-liquid chromatography. All but two species contain hydroxyeicosenoie acid in amounts ranging from 45 to 74%. The remaining two species contain about 50% C₁₈ hydroxy acids, but none of the C₂₀ hydroxy acid. Presented at the spring meeting of the American Oil Chemists' Society, St. Louis, Missouri, May 1–3, 1961. A laboratory of the Northern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.     

Search for new industrial oils. X. Seed oils of the calenduleae

Seed oils from 29 species in five genera of the tribe Calenduleae, family Compositae, have been examined to determine the distribution of dimorphecolic acid (9-hydroxyl-trans-10,trans-12-octadecadienoic acid) among the close relatives ofDimorphotheca. Dimorphecolic acid occurs in all five of theDimorphotheca species ofOsteospermum in amounts ranging from 34–75% of the oil. In all other species of the tribe analyzed to date, including 14 species ofOsteospermum, two ofCalendula, and two ofChrysanthemoides, the oil contained conjugated trienoic acids ranging from 14–60%. No. Util. Res. and Dev. Div., ARS, USDA. ARS, USDA     

Search for new industrial oils. VII

Seed oils from 37 plant species in 18 families have been analyzed for fatty acid composition by the isomerization method. The variability encountered is evidenced by the range in content of component acids: from 0–23% for apparent linolenic acid, from 8–74% for apparent linoleic acid, and from 2–88% for apparent oleic acid. Dimorphecolic acid has been found to the extent of approximately 60% in a second species ofDimorphotheca, D. pluvialis (L.) Moench, and in the closely related species,Osteospermum ecklonis (DC.) T. Norl.O. spinescens Thunb. contained instead 30% of a conjugated triene, presumably the same as the 8,10,12-octadecatrienoic reported from the relatedCalendula officinalis L. Oils rich in monoenoic acids are mostly in the Umbelliferae and Araliaceae and presumably contain petroselinic acid as well as oleic. Presented at the AOCS meeting in St. Louis, Mo., May 1–3, 1961. A laboratory of the Northern Utilization Research and Development Division, Agricultural Research Service, U.S.D.A. Agricultural Research Service, U.S.D.A.     

Search for new industrial oils. IV

Summary Chemical screening of seed oils continues to reveal nature's diversity. This work provides leads to numerous species which warrant further research to investigate their oil and meal in greater detail, to appraise their crop potential, and to assess their practical value for providing new oilseeds. This is a laboratory of the Northern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture. Agricultural Research Service, U. S. Department of Agriculture.     

Search for new industrial oils. viii. the genuslimnanthes

Seed oils from most of the known species and varieties ofLimnanthes were analyzed for their fatty acid content. Each contained at least 95% acids with more than 18 carbon atoms. The major component acid,cis-5-eicosenoic, ranged 52–77% of the acids present. Seeds of all species examined contained thioglucosidic precursors of volatile isothiocyanates, liberated by the action of mustard seed enzymes on the meal. One species also yielded a small amount of an oxazolidinethione-like compound of the type associated with enzyme-treated rapeseed meal.     

Search for new industrial oils. V. Oils of cruciferae

Seeds from 37 species of plants in the family Cruciferae were analyzed for oil and protein, and the fatty acid composition of the oils was determined by gas-liquid chromatography. Erucic acid, generally considered characteristic of crucifer oils, occurs in about three-fourths of these species in amounts ranging from 3 to 59%. Some oils free of erucic acid contain up to 63% linolenic acid or up to 58% eicosenoic. Presented at the spring meeting of the American Oil Chemists' Society, St. Louis, Missouri, May 1–3, 1961. A laboratory of the Northern Utilization Research and Development Division. Agricultural Research Service, U. S. Department of Agriculture.     

Search for new industrial oils. XI. Oils of boraginaceae

Analysis of seed oils from 29 species of the family Boraginaceae revealed widespread occur-rence of 6,9,12-octadecatrienoic and C₁₈ noncon-jugated tetraenoic acids in addition to linolenic and other common C₁₆ and C₁₈ acids. The 6,9,12-octadecatrienoic acid ranged in amount from 0-27%, tetraene from 0-17%, and linolenic acid from 0.3-50%. Iodine values of the oils ranged from 88-225. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA. A division of ARS, USDA.     

Search for new industrial oils. III. Oils from compositae

Summary Screening analyses of oils from seeds of 16 species of theCompositae family reveal numerous indications of unusual component fatty acids or interferences with the application of standard methods. Epoxyoleic acid is indicated in amounts from 1% to 67%. Conjugated dienes equivalent to 5% to 48% of C₁₈ acid appear in four oils. Hydroxyl groups are found in two oils in amounts corresponding to 20% and 70% of a C₁₈ acid. Of special interest is the oil fromDimorphotheca aurantiaca, which appears to contain some 50% of an acid with both an hydroxyl group and conjugated diene. Oil fromRudbeckia bicolor var.superba contains 76% of apparent linoleic acid and may rank among the richest sources of this acid. This is a laboratory of the Northern Utilization Research and Development Division. Agricultural Research Service, U. S. Department of Agriculture.     

Search for new industrial oils. I. Selected oils from 24 plant families

Summary The group of analyses used in this preliminary screening of oils has proved capable of indicating many seed species that contain oils of unusual or unknown composition. Some of the oils are characterized sufficiently to suggest probable commercial uses; others give no evidence of properties that would lead to their use while present commercial oils are in adequate supply. Still other oils are shown to have unknown composition, which must be determined before their potential value can be judged. The study as yet contains too few species to generalize about the relationship between botanical classification and oil composition. It does however provide numerous leads in the search for oils of industrial value. This is a laboratory of the Northern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture. Agricultural Research Service, U. S. Department of Agriculture.     

Search for new industrial oils. XIII. Oils from 102 species of cruciferae

Seed from additional species of Cruciferae have been analyzed for crude protein, oil and fatty acids in the oil. Oils were like those reported earlier from other crucifers, except forCardamine impatiens which is unique among known seed oils because it contains some 25% dihydroxy acids. Erucic acid is present (0.3–55%) in about three-fourths of the 102 samples. Eicosenoic acid is a major constituent (32–53%) in four species and monohydroxy acids (45–72%) in another four. Linolenic acid occurs (2–66%) in oil of all species. Presented at the AOCS meeting in Chicago, Ill., October 11–14, 1964. A laboratory of the No. Utiliz. Res. and Dev. Div., ARS, USDA. ARS, USDA.     

Search for new industrial oils: XVI. Umbelliflorae—seed oils rich in petroselinic acid

Seed oils of the order Umbelliflorae, including those from the families Umbelliferae, Garryaceae, Araliaceae, Cornaceae, Davidiaceae, Nyssaceae and Alangiaceae, were analyzed for fatty acid composition by gas liquid chromatography (GLC) of their methyl esters. The characteristic fatty acid of the order, petroselinic acid, occurred in the Umbelliferae in amounts up to 85%. In the Araliaceae, the content was as high as 83% and in the Garryaceae as high as 81%. The other major acids were palmitic, oleic and linoleic acids, with small amounts of hexadecenoic, stearic, linolenic, and, in some cases, C₂₀ acids. petroselinic acid was determined by microscale ozonolysis of the C₁₈ monoenoic esters and subsequent GLC of the ozonolysis products. The occurrence of high oil contents (up to 46%) combined with exceptionally high (up to 83%) single component purity is notable and emphasizes the potential of the Umbelliflorae as a raw material source for the chemical industry.     

Search for new industrial oils. XII. Fifty-eight euphorbiaceae oils,including one rich in vernolic acid

Seed oil ofEuphorbia lagascae Spreng. contains 57% ofcis-12,13-epoxy-cis-9-octadecenoic (vernolic) acid. The amt of trivernolin in the glycerides of this species indicates random or restricted random distribution of the vernolic acid. Seed from 57 additional species in the Euphorbiaceae were analyzed for oil and protein contents and also for fatty acid composition of the oils. Iodine values (I.V.) of the oils ranged from 87–221. Among these oils, samples were encountered with as much as 76% linolenic, 77% linoleic or 84% oleic acid. Presented at the AOCS in New Orleans, 1964. A laboratory of the No. Utiliz. Res. & Dev. Div., ARS, USDA. ARS, USDA.     

Search for new industrial oils,IX.Cuphea,a versatile source of fatty acids

Seed oils from five species ofCuphea show three distinct patterns of fatty acid composition.C. hookeriana andC. painteri oils contain ca. 70% caprylic acid,C. ignea and C.llavea oils have over 80% capric acid, andC. carthagenensis oil contains 57% lauric and 18% capric acids. No. Utiliz. Res. and Dev. Div., ARS, USDA ARS, USDA     

Search for new seed oils. XV. Oils of boraginaceae

In a search for a preferred source of γ-linolenic (all-cis-6,9,12-octadecatrienoic) acid, seed oils of 33 species of Boraginaceae were examined. The desired triene was found primarily in the subfamily Boraginoideae in amounts ranging from 0.2 to 18%. Oils of this subfamily also contain 0.2 to 15% of the tetraene, all-cis-6,9,12,15-octadecatetraenoic acid. Total unsaturation and the relative proportions of the common acids varied widely in oils of the family. Monoene predominated in the subfamily Cordioideae, diene in Heliotropioideae, and a diverse composition among the Boraginoideae; seven had iodine values of 200 or above.Cordia verbenacea seed oil was unique among those examined in having 43% of C₂₀ acids and 23% of components more volatile in gas chromatography than the usual triglycerides. Presented at AOCS meeting, New Orleans, May 1967. Earlier papers of this series carried the running title “Search for New Industrial Oils.” The revised title is more appropriate for the basic chemical compositional data reported, that can be useful in a broader context than originally implied. No. Utiliz. Res. Dev. Div., ARS, USDA. ARS, USDA.     

Modification of vegetable oils. XIV. Properties of aceto-oleins

Summary Pure 1,2-diaceto-3-olein was prepared by acetylating mono-olein. A mixture of aceto-oleins was prepared by acetylating a mixture of mono-, di-, and trioleins derived from commercial oleic acid. Several natural oils were acetylated either by ester-ester interchange with triacetin or by glycerolysis followed by acetylation. The various products were examined for cloud and solid points, point of complete melting, and consistency. The 1,2-diaceto-3-olein, which contains 19.5% of acetyl group on a weight basis, has a melting point of −18.3°C. while the mixture of aceto-oleins, which contained 14.3% of acetyl on a weight basis, melted at −24°C. Acetylation of the natural oils raises in most instances their cloud and solid points and point of complete melting, but it also greatly increases their plasticity at lower temperatures. Aceto-compounds were used to plasticize highly hydrogenated cottonseed oil. These mixtures were prepared so that they possessed the consistency of margarine oil at room temperature. These mixtures, when compared with partially hydrogenated oil, butterfat, or a mixture of cottonseed oil and hydrogenated cottonseed oil, were softer below room temperature and firmer above room temperature. A margarine-like product containing 79% of aceto-olein and 18.5% of highly hydrogenated cottonseed oil had a practically constant consistency over the temperature range of −15° to 49°C. (5° to 120°F.). Presented at the 26th Fall Meeting of the American Oil Chemists' Society, Cincinnati, O., Oct. 20–22, 1952. One of the laboratories of the Bureau of Agricultural and Industrial Chemistry, Agricultural Research Administration, U. S. Department of Agriculture.     

Whole-plant oils,potential new industrial raw materials

In an extensive screening program, 14 plant species have been identified which have good potential as hydrocarbon- and rubber-producing crops. These plants contain from 5 to 10% oil plus polymeric hydrocarbon on a dry weight basis. Since their dry matter yield should be 11,200 to 22,400 kg/ha/year, they would produce several times as much oil as conventional oilseed crops. In these plants, the oil is not concentrated in storage organs, i.e., seed or fruit tissue, but is distributed throughout the whole plant. Several species are lactiferous, with oil as a major component of the latex. A few which are of primary interest as potential new sources of natural rubber produce an equal yield of by-product oil. A prominent feature of most whole-plant oils is their large component of nonglyceride esters. Such oils could become valuable new feedstocks for production of plasticizers for rubber and plastics and new sources of waxes, long chain alcohols, sterols, terpenes, fatty acids, and other products. A petroleum refinery could be operated on whole-plant oils, and some species are being referred to as potential “gasoline trees.” Presented at the AOCS Meeting, St. Louis, May 1978.     

New crop developments for industrial oils

Traditional industrial fats and oils are derived from inedible tallow or lard, fish and whale oil, and a small group of plant oils, including linseed, soybean, castor, tung, tall, and rapeseed oil. A group of new crops and prospective new crops is available to be utilized advantageously for the production of renewable industrial resources. Some of these plants have been studied extensively from germplasm variation through crop production and processing to evaluation of the final oil and meal products. Others are not developed that far yet. Case histories onCramble, Limnanthes, Lunaria (long chain acids),Lesquerella (hydroxy acids),Stokesia andVernonia (epoxy acids),Calendula (conjugated unsaturation),Cuphea (short chain acids), jojoba (liquid wax esters), andFoeniculum (petroselenic acid) indicate that many obstacles must be overcome to arrive at success.     

Trends in industrial markets for fats and oils and derivatives

During the past decade, research by industry and government has developed numerous new chemical markets for fats and oils derivatives. Lower prices for competitive raw materials have forced some of these new products into specialty markets. Economic factors, such as the continual growth of the chemical industry, population increases, and high consumer demand, have allowed for steady growth in the fat-derivative market. New fat-type plasticizers are currently consuming about 60 million pounds of fats annually. Synthetic lubricants will probably be consuming 20 million pounds of fatty diesters annually by 1965. Animal feeds consume approximately 600 million pounds of fats and fat derivatives annually and may eventually become the leading domestic nonfood market for fats. The protective coating market as an outlet for fats continues to decline, and the continuing shift to nonfat materials and changes in pain formulas indicate that, while the demand for protective coatings may increase, the use of fats in their manufacture may not share in the increase. Nonfat chemical raw materials provide intense price competition for fatty raw materials. Fat prices are influenced by the demand for use in food, soap, paints, and possibly animal feeds rather than by the demand for use as chemical raw materials. Presented before the American Oil Chemists' Society, New York, October, 17, 1960.     

Trends in industrial usage for vegetable oils — symposium overview

Vegetable oils are firmly established components of many industrial products and contribute a small but important share to the oleochemical and chemical industries-about 2% of total organic chemicals produced. The oleochemical industry is a mature one with low profit margins and in need of novel products and product applications, the development of which will require both basic and applied research. Several symposium participants identify areas that could add significantly to existing markets for unmodified vegetable oils, such as a diluent or enhancing agent in the application of pesticides and as an energy or heat source. Others show that considerable potential exists for new chemicals and modified vegetable oils and unique chemicals derived therefrom in value-added products such as coatings, polymers, lubricant additives or food additives, sometimes involving unique oils other than the traditional commodity mix. Without doubt, this is a time for the oleochemicals industry to invest in the future with nontraditional approaches to research and development. The oleochemical industry can and should expand its horizons, but with the realization that vegetable oils will have a lesser role compared to that of other renewable resources, such as wood and agricultural residues.