Of oleic acid

HOOO(CH2)7COOH. Colourless plates, m.p. lOfi C. Made by the oxidation of oleic acid with ozones. 

HOOC-[CHa]8-COOH, CioH.aO. Colourless leaflets m.p. 134°C. Manufactured by heating castor oil with alkalis or by distillation of oleic acid. Forms an anhydride, m.p. 78 C. The esters of sebacic acid are used as plasticizers, especially for vinyl resins. 

Spreading velocities v are on the order of 15-30 cm/sec on water [39], and v for a homologous series tends to vary linearly with the equilibrium film pressure, it", although in the case of alcohols a minimum seemed to be required for v to be appreciable. Also, as illustrated in Fig. IV-3, substrate water is entrained to some depth (0.5 mm in the case of oleic acid), a compensating counterflow being present at greater depths [40]. Related to this is the observation that v tends to vary inversely with substrate viscosity [41-43]. An analysis of the stress-strain situation led to the equation... 

Fig. IV-3. Velocity profiles for particles suspended in water with elapsed time, due to spreading of oleic acid. Time after onset of spreading O, 5 sec, , 5 sec. (From Ref. 31.)...

Typically, soHd stabilizers utilize natural saturated fatty acid ligands with chain lengths of Cg—C g. Ziac stearate [557-05-1/, ziac neodecanoate [27253-29-8] calcium stearate [1592-23-0] barium stearate [6865-35-6] and cadmium laurate [2605-44-9] are some examples. To complete the package, the soHd products also contain other soHd additives such as polyols, antioxidants, and lubricants. Liquid stabilizers can make use of metal soaps of oleic acid, tall oil acids, 2-ethyl-hexanoic acid, octylphenol, and nonylphenol. Barium bis(nonylphenate) [41157-58-8] ziac 2-ethyIhexanoate [136-53-8], cadmium 2-ethyIhexanoate [2420-98-6], and overbased barium tallate [68855-79-8] are normally used ia the Hquid formulations along with solubilizers such as plasticizers, phosphites, and/or epoxidized oils. The majority of the Hquid barium—cadmium formulations rely on barium nonylphenate as the source of that metal. There are even some mixed metal stabilizers suppHed as pastes. The U.S. FDA approved calcium—zinc stabilizers are good examples because they contain a mixture of calcium stearate and ziac stearate suspended ia epoxidized soya oil. Table 4 shows examples of typical mixed metal stabilizers. 

The most commonly used emulsifiers are sodium, potassium, or ammonium salts of oleic acid, stearic acid, or rosin acids, or disproportionate rosin acids, either singly or in mixture. An aLkylsulfate or aLkylarenesulfonate can also be used or be present as a stabilizer. A useful stabilizer of this class is the condensation product of formaldehyde with the sodium salt of P-naphthalenesulfonic acid. AH these primary emulsifiers and stabilizers are anionic and on adsorption they confer a negative charge to the polymer particles. Latices stabilized with cationic or nonionic surfactants have been developed for special apphcations. Despite the high concentration of emulsifiers in most synthetic latices, only a small proportion is present in the aqueous phase nearly all of it is adsorbed on the polymer particles. 

Sodium Dispersions. Sodium is easily dispersed in inert hydrocarbons (qv), eg, white oil or kerosene, by agitation, or using a homogenizing device. Addition of oleic acid and other long-chain fatty acids, higher alcohols and esters, and some finely divided soHds, eg, carbon or bentonite, accelerate dispersion and produce finer (1—20 -lm) particles. Above 98°C the sodium is present as Hquid spheres. On cooling to lower temperatures, soHd spheres of sodium remain dispersed in the hydrocarbon and present an extended surface for reaction. Dispersions may contain as much as 50 wt % sodium. Sodium in this form is easily handled and reacts rapidly. For some purposes the presence of the inert hydrocarbon is a disadvantage. 

Positionalisomeri tion occurs most often duting partial hydrogenation of unsaturated fatty acids it also occurs ia strongly basic or acidic solution and by catalysis with metal hydrides or organometaUic carbonyl complexes. Concentrated sulfuric or 70% perchloric acid treatment of oleic acid at 85°C produces y-stearolactone from a series of double-bond isomerizations, hydration, and dehydration steps (57). 

Alkali fusion of oleic acid at about 350°C ia the Varrentrapp reaction causes double-bond isomerization to a conjugated system with the carboxylate group followed by oxidative cleavage to form palmitic acid (75). In contrast, alkaU fusion of riciaoleic acid is the commercial route to sebacic acid [111 -20-6] ... 

Metathesis of oleic acid to produce a C g straight-chain dibasic acid can be carried out at 70°C with a WCl Sn(CH2)4 catalyst or with rhenium heptoxide promoted by Sn(CH2)4 (55,77). 

Rhodium catalyst is used to convert linear alpha-olefins to heptanoic and pelargonic acids (see Carboxylic acids, manufacture). These acids can also be made from the ozonolysis of oleic acid, as done by the Henkel Corp. Emery Group, or by steam cracking methyl ricinoleate, a by-product of the manufacture of nylon-11, an Atochem process in France (4). Neoacids are derived from isobutylene and nonene (4) (see Carboxylic acids, trialkylacetic acids). 

Carbonylation, or the Koch reaction, can be represented by the same equation as for hydrocarboxylation. The catalyst is H2SO4. A mixture of C-19 dicarboxyhc acids results due to extensive isomerization of the double bond. Methyl-branched isomers are formed by rearrangement of the intermediate carbonium ions. Reaction of oleic acid with carbon monoxide at 4.6 MPa (45 atm) using 97% sulfuric acid gives an 83% yield of the C-19 dicarboxyhc acid (82). Further optimization of the reaction has been reported along with physical data of the various C-19 dibasic acids produced. The mixture of C-19 acids was found to contain approximately 25% secondary carboxyl and 75% tertiary carboxyl groups. As expected, the tertiary carboxyl was found to be very difficult to esterify (80,83). 

Examples are given of common operations such as absorption of ammonia to make fertihzers and of carbon dioxide to make soda ash. Also of recoveiy of phosphine from offgases of phosphorous plants recoveiy of HE oxidation, halogenation, and hydrogenation of various organics hydration of olefins to alcohols oxo reaction for higher aldehydes and alcohols ozonolysis of oleic acid absorption of carbon monoxide to make sodium formate alkylation of acetic acid with isobutylene to make teti-h ty acetate, absorption of olefins to make various products HCl and HBr plus higher alcohols to make alkyl hahdes and so on. 

Figure 23-36 shows a computer calculation with these specific rates, but which does not agree quantitatively with the figure shown by Swern. The time scales appear to be different, but both predict a peak in the amount of oleic acid and rapid disappearance of the first two acids. 

There has been only one major use for ozone today in the field of chemical synthesis the ozonation of oleic acid to produce azelaic acid. Oleic acid is obtained from either tallow, a by-product of meat-packing plants, or from tall oil, a byproduct of making paper from wood. Oleic acid is dissolved in about half its weight of pelargonic acid and is ozonized continuously in a reactor with approximately 2 percent ozone in oxygen it is oxidized for several hours. The pelargonic and azelaic acids are recovered by vacuum distillation. The acids are then esterified to yield a plasticizer for vinyl compounds or for the production of lubricants. Azelaic acid is also a starting material in the production of a nylon type of polymer. 

A similar reaction occurs with fatty acids (such as stearic acid) or methyl stearate, which undergo isomerization, cracking, dimerization, and oligomerization reactions. This has been used to convert solid stearic acid into the more valuable liquid isostearic acid [102] (Scheme 5.1-70). The isomerization and dimerization of oleic acid and methyl oleate have also been found to occur in chloroaluminate(III) ionic liquids [103]. 

Steam probably contained a trace of Oleic acid. 

Fats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products. 

This soln was mixed just before use with 2p of oleic acid... 

The reaction of olefin sulfation and its possibilities has been extensively studied [3-10] and it was used to produce alcohol sulfates. Dry distillation of spermaceti gives palmitic acid and cetene-1, which can be sulfated with sulfuric acid to give cetyl-2 sulfate [11]. Other surfactants were obtained from olefins produced from natural substances, such as alcohol sulfates by sulfation of olefins from decarboxylation of oleic acid [12], by sulfation of olefins made by dehydrating hydroabietyl alcohol, by direct sulfation of abietyl alcohol [13,14], or by sulfation of natural terpenes [15]. 

Although, the enzymatic reaction of esters with amines or ammonia have been well documented, the corresponding aminolysis with carboxylic acids are rarer, because of the tendency of the reactants to form unreactive salts. For this reason some different strategies have been used to avoid this problem. Normally, this reaction has been used for the preparation of amides of industrial interest, for instance, one of the most important amides used in the polymer industry like oleamide has been produced by enzymatic amidation of oleic acid with ammonia and CALB in different organic solvents [10]. 

Addition of oleic acid to PCL caused a significant increase in the rate of chain scission, the effect being proportional to the amount of acid added (Fig. 26). The effect of added base, e.g., n-decylamine, was even more substantial, reducing the molecular weight of PCL from 60,000 to 20,000 in 20 days (Fig. 26). This reduction in mo-... 

FIGURE 26 Enhancement of the rate of hydrolytic chain scission of PCL in the presence of oleic acid and n-decylamine. (From Ref. 49.)... 

BAM showed bright regions due to the Ag particles and dark regions occupied primarily by oleic acid (Fig. 10b). TEM showed monolayer domains of surfactant-coated silver particles within regions of oleic acid. Vertical transfer onto quartz plates of up to eight layers with good linearity was reported. 

The carbon chains of samrated fatty acids form a zigzag pattern when extended, as at low temperamres. At higher temperatures, some bonds rotate, causing chain shortening, which explains why biomembranes become thinner with increases in temperamre. A type of geometric isomerism occurs in unsaturated fatty acids, depending on the orientation of atoms or groups around the axes of double bonds, which do not allow rotation. If the acyl chains are on the same side of the bond, it is cis-, as in oleic acid if on opposite sides, it is tram-, as in elaidic acid, the tram isomer of oleic acid (Fig-... 

Aldrich 90%) of oleic acid were dissolved in 200 g of 1-octadecene at room temperature. The reaction mixture was heated to 320 °C with a heating rate of 3.3 C/min, and then kept at that temperature for 30 min. When the reaction temperature reached 320 °C, a severe reaction occurred and the initial transparent solution became turbid and brownish black. The resulting solution... 

Fig. 12 Cobalt nanorods synthesized in the presence of a mixture of oleic acid and a octylamine b dedecylamine c hexadecylamine d octadecylamine...

Finally brief reference should be made to the stabilization of synthetic latices, particularly high solids latices of the GR-S type and the improvement of the cold GR-S polymerization by a synthetic emulsifying agent known as EMCOL K-8300, which is a sulfosuccinic acid ester (sodium salt) of the isopropanolamide of oleic acid ... 

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