Extraction of omega‐6 fatty acids from speciality seeds

‘Omega‐6 vegetable oils’ are a small but important group of vegetable oils used widely in the food, neutraceutical, cosmetic and pharmaceutical industries for their linoleic acid (18:2 n‐6) and more importantly gamma linolenic acid (18:3 n‐6) content. These omega‐6 fatty acids have numerous health benefits recognized worldwide. With linoleic acid being readily available from many dietary sources, one wonders why there is a need to extract the oil from speciality oilseeds, however those that suffer with many of the conditions that omega‐6 fatty acids are said to be beneficial for are frequently advised to take extra supplements of these fatty acids. Due to their wide use as a nutraceutical, omega‐6 fatty acids are in high demand, causing a niche market for extraction of these oils from speciality seeds.     

Uses of fats,fatty oils,and derivatives in the petroleum industry

Conclusion The use of fats, fatty oils, and derivatives is extensive in the petroleum industry to improve its lubricants in their wetting ability or oiliness. Fats and their derivatives serve to carry active elements such as chlorine, sulfur, and phosphorus for the improvement of load-carrying capacity, resistance to oxidation, inhibiting corrosiveness, and preventing wear during use. Greases are compounded from whole fats and fatty acids which serve under suitable conditions to gel lubricating oil and thus fulfill lubricating requirements which the liquid oils cannot themselves satisfy. Greases and their components may be tested for skin hardening in storage by means of an oxygen absorption test which distinguishes between satisfactory and unsatisfactory ingredients and products. Presented in a symposium on the Industrial Applications of Fats & Fatty Acids at the Fall Convention of the American Oil Chemists Society, Chicago, Oct. 1939.     

Trends in industrial uses of palm and lauric oils

An attempt is being made to determine the importance of palm and lauric oil today and in the coming years of this decade whereby their industrial use in western Europe is considered outside the field of human and animal nutrition. The basic oleochemicals like fatty acids, fatty acid methyl esters, fatty alcohols and their most important derivatives are discussed as the essential products. Detergents are one of the most significant areas of application for basic oleochemicals and their derivatives. Changes in the application profiles of the final products are expected for the detergent industry in the coming years. These tendencies have been scrutinized with respect to their influence on future demand for palm and lauric oil. The competitiveness of natural oil-based oleochemicals versus ethylene-and paraffin-based synthetics is of great significance for the development of natural oils. It is attempted to elucidate the chances of natural oleochemicals in connection with petrochemical raw material developments.     

Production of polyvinyl esters by ester interchange

Summary Mixed polyvinyl esters of acetic acid and higher fatty acids can be made by ester interchange between polyvinyl acetate and fatty esters. Their properties indicate that some of these products merit attention as materials for use in the drying oil industries. Because of their enhanced drying qualities and greater tolerance of the presence of saturated acid components, in comparison with the corresponding glycerides, they potentially broaden the range of fatty materials utilizable as drying oils. Presented at the fall meeting, American Oil Chemists' Society, Minneapolis, Minn., Oct., 11–13, 1954.     

Industrial Waste Materials as a Source of Sterols

The content of sterols and their derivatives have been examined in the following industrial waste materials: oily bleaching earth, volatiles from deodorization of oils, residue after distillation of tall oil, residue after distillation of crude animal and plant fatty acids. Amount of sterols directly occurring in such raw materials as low erucic and high erucic rapeseed oil and tall oil has also been stated. The quality constitution of sterols contained in those raw materials has been estimated. The profitability of getting sterols from those sources for the purposes of the cosmetic and pharmaceutical industries have been considered.     

Methyl esters in the fatty acid industry

Methyl esters, derived from natural fats or oils, can be used as alternatives to fatty acids in the production of a number of derivatives. The derivatives that can be made from methyl esters include fatty alkanolamides, fatty alcohols, isopropyl esters, and sucrose polyesters. By using methyl esters as the raw materials, several benefits may be realized, such as, the ability to make higher purity finished products, the use of milder conditions during syntheses, and the need for less expensive materials of construction. In addition to the applications mentioned, methyl esters are being used increasingly in fractional distillations because they have lower boiling points and are less corrosive than fatty acids.     

The use of fatty acid derivatives in cosmetics and toiletries

A large variety of fatty acid derivatives are utilized by the cosmetics and toiletries industry to fulfill many functions in their products. These ingredients, based on renewable resources are reviewed with respect to source and method of manufacture, physical and functional properties, and the place they find in all types of cosmetic products.     

The role of fats and oils in cosmetics

The earliest emollients in the history of cosmetics were the naturally occurring animal fats and vegetable oils. These provided soothing and smoothing action on the skin and grooming effects on head and beard hair. For the most part, odor problems limited the interest in oils derived from fish. With the increasing sophistication of users and increasing understanding of the technology of these materials, the short-comings of natural fats and oils were overcome in several ways: (a) increased stability through use of antioxidants; (b) reduced odor through improved processing; (c) improved stability and diversification through chemical modification; (d) increased diversity through preparation of derivatives, and (e) substitution of mineral oil. Today the most important single cosmetic use of an unmodified natural fat or oil is that of castor oil as the base for lipsticks. Other unmodified oils have largely minor specialty uses, particularly in higher-priced cosmetics. These include almond oil, apricot kernel oil, sesame oil, safflower oil, wheat germ oil, avocado oil, turtle oil and mink oil. Cocoa butter is used to some extent in suntan products. Reconstituted fractionated coconut oil is widely used. Polyglycerol esters of fatty acids are increasing in importance. Hydrogenation has produced stable oils useful in cosmetics. Alkyl esters and monoglycerol esters of fatty acids offer a wider range of properties than the original oils. Improvements in the naturally occurring fats and oils have made it possible for them to compete in some characteristics, and current interest in “natural” cosmetics may turn the attention of the cosmetic chemist back to improved versions of the classical raw materials. One of five papers in the symposium “Fats and Oils in Cosmetics and Pharmaceuticals,” presented at the AOCS Meeting, Atlantic City, October 1971.     

Fats and oils in agriculture

Fats, oils, and their derivatives are reviewed, in their roles as emulsifiers and surfactants and as pesticide derivatives, and in their activity per se. As emulsifiers and surfactants they offer a wide range of hydrophile-lipophile balance (HLB) values to assist formulators in developing saleable products. Their lipoid solubilities aid in evaporation retardation, plant penetration, and absorption. Often they greatly improve the performance of the active ingredients. Nitrogen derivatives such as amines and quaternaries, fatty alcohols, acid esters, and other agricultural chemicals are reviewed. Examples are cited on the effect of the length of the carbon chain and their number in such herbicides as 2,4-D and dalapon, as well as the biological properties of various aliphatic groups in insect larvicides, plant growth regulators, and fungicides. The role vegetable oils can play in the looming energy shortages as petroleum oil substitutes is discussed. They offer a challenging future in agricultural applications.     

Fractional distillation

While practically all the fatty acids produced in the fatty acid industry are distilled products, these materials are all, at least to some degree, fractionated fatty acids. Rarely indeed are today’s fatty acids suited for any of the many applications to which they are put without the quality and homolog distribution improvements which only fractional distillation can guarantee. Thus, this separation is of vital importance within the fatty acid and derivative industries. Fractional distillation is industrially a practical separative method for: (a) 16:0 and 18:0 fatty acids, such as those derived from hydrogenated fats and oils like tallow, soybean, cottonseed soapstocks, palm oil and others; (b) 18:0, 20:0, 22:0, and 24:0 fatty acids from hydrogenated fish oils or high erucic rapeseed oil; and (c) 8:0, 10:0, 12:0, and 14:0 fatty acids from the hydrogenated fatty acids from the lauric oils group (coconut, palm kernel, babassu, etc.). While theoretically possible under idealized conditions in the laboratory, it is not practical to separate palmitic, oleic, heptadecanoic, and stearic acids by means of fractional distillation     

Processing for industrial fatty acids - I

Palm kernel and coconut oils are particularly important to the fatty acid industry because they are the major sources of lauric acid. This paper describes the processes used to convert these oils to their fatty acids. These in turn may be fractionated into saturated/unsaturated acids and to specific chain lengths by winterization, panning and pressing, fractional distillation, solvent crystallization and hydrophilization methods. The products are important raw materials for the soap, detergent and oleochemical industries. Emery Industries     

Challenges to a mature industry: Marketing and economics of oleochemicals in Western Europe

Basic oleochemicals are produced by splitting and further reactions of oils and fats: fatty acids, glycerine, fatty acid methyl esters, fatty alcohols and amines. The last two are included in the list of oleochemical raw materials, primarily because of their importance in the preparations of further derivatives. The wide range of derivatives of oleochemical raw materials such as fatty alcohol ethoxylates, fatty alcohol sulfates, fatty alcohol ether sulfates, quaternary ammonium compounds and soaps are summarized. Oleochemicals such as fatty alcohols and glycerine from oils and fats have equivalents on the basis of petrochemicals. Using the customary terminology, petrochemical products are referred to as “synthetics.” The are included in the present discussion because in the application of oleochemical raw materials the origin of the material is often less important than the structure. Oleochemistry can be regarded as a mature branch of chemistry, with many applications for its products, but with few completely new fields. The challenge and the opportunities for oleochemistry today lie in the changing economic and ecological conditions. Availability and price development of oils and fats are discussed with particular reference to European conditions, for these are the prerequisites if oleochemicals are to be competitive and are to improve their chances in the marketplace. The importance and development of the oleochemical raw material fatty acids, fatty acid methyl esters, glycerine, fatty alcohols and amines are considered on the basis of historical data. In considering future developments of oleochemicals, the capacity, demand and the possible influence of petrochemistry or crude oil is discussed. The highly developed oleochemical raw materials industry is a flexible supplier of medium-to long-chain fatty alkyl groups. These facts, together with the well organized supply lines for raw materials and the considerable potential of these renewable raw materials, could provide the necessary conditions for the oleochemical raw materials industry to fulfil its future tasks on a larger scale. This could arise, for example, due to the partial substitution of petrochemical surfactants, if this should become necessary as a result of developments in the price and availability of crude oil, or on grounds of ecological factors.     

Contents of Fatty Acids, Selected Lipids and Physicochemical Properties of Western Australian Sandalwood Seed Oil

The study was designed to characterise two extracts of Western Australian sandalwood (Santalum spicatum) seed oils for their physicochemical and lipid characteristics. Sandalwood plantation’s surplus seeds could be used for their oil content, to improve the commercial viability of this industry. The seed oils were obtained by solvent extraction and supercritical carbon dioxide extraction respectively. Important physicochemical parameters were compared with other oils commonly used in pharmaceutical and cosmetic products. Acid values were found to be higher (6.0–7.5 mg KOH/1 g oil) while peroxide values (6.7–9.0 mequiv/Kg) were lower than reported for other oils. Tocopherols were found to be lower than those usually reported for nut oils (α-tocopherol 1–3 mg/100 g; δ-tocopherol 2.2–5.7 mg/100 g), squalenes and phytosterols were found in considerable quantities. The fatty acid content consisted largely of ximenynic acid (35 %) and oleic acid (52 %). No oxidative derivatives of fatty acids were observed. Although there were statistically significant differences in some properties, the magnitude of these were insufficient to conclude there were any notable differences in the two oil extracts.     

A Multivariate Identification of Natural Triglyceride Oils

Natural oils possess a characteristic and more or less unique pattern of fatty acids and triacylglycerols. These patterns can be used in several manners, as a means of identification, for batch-consistency testing (e. g. for the pharmaceutical and cosmetic industry), detection of adulteration and also possibly as a basis for a chemotaxonomy, revealing relationships between species. The fatty acid composition, determined by GC/MS of the methyl esters and the triacylglycerol pattern analysed by reversed phase high performance liquid chromatography, were utilized in multivariate-statistical analysis to ‘map’ and classify different oils. A class model was developed for each of the different sources of oil, constituting an objective and quantitative means of identification, through nearness in the multi-dimensional measurement space.     

Catalytic Synthesis of Higher Aliphatic Amines from the Corresponding Alcohols

Aliphatic amines are of considerable industrial importance and find application in almost every field of modern technology, agriculture, and medicine [1], Lower aliphatic amines (C₁ to C₆) are important intermediates for the chemical and pharmaceutical industries. A large number of drugs, herbicides, pesticides, dyes, and other chemicals contain amino pups which originate from reactions with such intermediates, Many important applications of higher aliphatic amines (fatty amines) and their derivatives (most important derivatives are quarternary ammonium compounds) are based on their cationic surface activity. Relatively small amounts of such compounds are usually required to achieve the desired changes in surface and colloidal properties. Thus, not surprising, one of the first applications of fatty amines was in the flotation separation of nonmetallic materials such as potash, feldspar, phosphate, and mica. Today, probably the biggest demand for fatty amines lies in the production of fabric softeners. There are other important applications for aliphatic amines in the plastics and protective coat industries as emulsion stabilizers, mold release agents, pigment dispersers, and flushing agents. They are used as catalysts for polyurethane production. For granular products, alkylamines are used as anticaking and antidusting agents. In the rubber industry they are used as oxidation inhibitors and catalysts for accelerating vulcanization. Aliphatic amines find also many applications in the petroleum industry, especially as corrosion inhibitors and as components of lubricating oils, greases, and fuel oil where they act as sludge dispersants and stabilizers. They are added to gasoline as corrosion inhibitors.     

Glycerin - Ein fettchemischer Grundstoff im Wandel der Zeit

Glycerine - The History of an Oleochemical Raw Material Being a constituent of all fats and oils, natural glycerine has always played a key role in oleochemical manufacturing processes. Owing to its special physical and chemical properties, glycerine, which is obtained as a byproduct in neutral oil saponification and in the splitting and transesterification of fats and oils, has succeeded in becoming established and gaining in importance even under changing economic conditions. The major part of glycerine and its derivatives produced worldwide is nowadays used in the cosmetic and pharmaceutical industries, the food and tabacco industries, and in plastics manufacturing. Often its lack in color and odor and the fact that it presents no health hazards are of decisive importance. The range of applications is accordingly very wide. The current world consumption is estimated at about 500000 tons per year. Therefore the useful and economically efficient production, processing and marketing of this valuable oleochemical raw material continues to be one of the focal activities of the chemical industry today.     

The synthesis,properties, and applications of ascorbyl esters

Ascorbic acid is a naturally occurring antioxidant. Nevertheless, its primary applications as an antioxidant in the life science, food and pharmaceutical industries are limited because of its hydrophilic nature. Alternatively, ascorbyl acid esters are potential surfactants and antioxidants. Chemical methods for the synthesis of ascorbyl esters lead to the formation of side products and simultaneous decomposition of ascorbic acid due to harsh reaction conditions. In contrast, lipases are used as regioselective and mild catalysts for the synthesis of ascorbyl esters. So far, various acyl donors namely, fatty acids, fatty acid alkyl esters, fatty acid vinyl esters and triacylglycerols have been explored for the synthesis of ascorbyl fatty esters. Other compounds such as L‐methyl lactate, bixin, phenyl butyric acid are also used as acyl donors. This article is focused on the recent developments of lipase‐catalyzed synthesis of ascorbyl esters, their antioxidant properties and applications.     

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.     

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.