Oleyl alcohol

HD-Eutanol V PH Ocenoh, ds-9-octadecen-l-ol oleic alcohol oleo alcohol oleol. 

Solubihty soluble in ethanol (95%), and ether practically insoluble in water. 

Antifoaming agent dissolution enhancer emollient emulsifying agent skin penetrant sustained-release agent. 

The bulk material should be stored in a well-closed container in a cool, dry, place. 

Oleyl alcohol is mainly used in topical pharmaceutical formulations and has been used in transdermal delivery formulations. It has been utilized in the development of biodegradable injectable thermoplastic oligomers, and in aerosol formulations of insulin and albuterol.  

About 200 g. of solid sodium chloride (Note 7) is added to the flask and the butyl alcohol is removed by steam distillation (Note 8). The alcohol layer is separated while still hot (Note 9), transferred to a t-1. beaker, and heated on a hot plate with stirring until the temperature reaches about 160°. By this time all the water is removed and foaming has stopped (Note 10). The hot liquid is transferred to a i-l. Claisen flask having a 25-cm. fractionating side arm and distilled at 3 mm. After a small fore-run of 5-10 g., the main fraction boils at 177-183°/3 mm. and amounts to 330-340 g. (82-84 per cent of the theoretical amount) (Note 11). 

Commercial butyl alcohol is dried by distillation through a i-m. column and the portion boiling at 117.5 118.5° is used. The ordinary commercial alcohol is usually sufficiently pure so that the bulk of the alcohol remaining in the flask after the temperature at the top of the column reaches 117° need not be distilled but may be used directly for the reduction. 

If one wishes to reduce this time, external heat may be applied until the boiling point is reached. In a run in which the butyl alcohol was heated to boiling before the addition of the 

The reaction mixture should not be cooled below the boiling point of the butyl alcohol as a continuously vigorous reaction is essential for good yields. 

The procedure up to this point requires about three and one-half hours and should be continuous. 

Checked by Cliff S. Hamilton, C. W. Winter, and Alfred Stepan. 

In a 5-1. round-bottomed flask fitted with a large-bore reflux condenser are placed 200 g. (230 ml., 0.65 mole) of ethyl oleate (Note 1) and 1.5 1. of absolute ethanol (Note 2). Through the reflux condenser is added 80 g. (3.5 gram atoms) of sodium rapidly enough to keep up a vigorous reaction. The flask is shaken occasionally. After the initial reaction has subsided, about 200 ml. more of absolute alcohol is added, and the mixture is heated on a steam bath until all the sodium has reacted. Then 500 ml. of water is added, and the mixture is refluxed for 1 hour to saponify the unreacted ester. The mixture is cooled, and 1.2 1. of water is added. The unsaponifiable fraction is extracted with ether, and the extracts are washed with 1% potassium hydroxide solution and then with water till free of alkali when tested externally with phenolphthalein. The ether extract is dried over sodium sulfate, the ether removed by distillation, and the residue distilled through an efficient column (Note 3). A yield of 84-89 g. (49-51%), b.p. 150-152°/ mm., is obtained. 

Fifty grams of the crude olcyl alcohol is crystallized from 400 ml. of acetone at —20° to —25 (Note 4) in a jacketed sintered- 

was used. The checkers distilled ethyl oleate (technical, Eastman Kodak Company) and used the fraction boiling at 164-166°/ mm., 1.4522. 

The purity of the absolute alcohol is of prime importance. Alcohol dried only by a lime process gives a low yield (20-25%). The alcohol used in this procedure was dried over lime and then over aluminum /erf.-butoxide, after which it was distilled directly into the flask used for the reaction. 

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Fig. XIV-3. Steric effects in the penetration of sodium cetyl sulfate monolayers by cetyl alcohol and oleyl alcohol.

The importance of steric factors in the formation of penetration complexes is made evident by the observation that although sodium cetyl sulfate plus cetyl alcohol gives an excellent emulsion, the use of oleyl alcohol instead of cetyl alcohol leads to very poor emulsions. As illustrated in Fig. XIV-3, the explanation may lie in the difficulty in accommodating the kinked oleyl alcohol chain in the film. 

The free acids are obtained upon acidification. Fata usually consist of mixtures of glycerides. The term wax is usually applied to esters of fatty acids with other alcohols such as cetyl alcohol CH3(CH2),4CHjOH and oleyl alcohol CH3(CHj),CH=CH(CHj),CH30H. 

Cosmetics and Pharmaceuticals. The main use of hexadecanol (cetyl alcohol) is in cosmetics (qv) and pharmaceuticals (qv), where it and octadecanol (stearyl alcohol) are used extensively as emoUient additives and as bases for creams, Hpsticks, ointments, and suppositories. Octadecenol (oleyl alcohol) is also widely used (47), as are the nonlinear alcohols. The compatibiHty of heavy cut alcohols and other cosmetic materials or active dmg agents, their mildness, skin feel, and low toxicity have made them the preferred materials for these appHcations. Higher alcohols and their derivatives are used in conditioning shampoos, in other personal care products, and in ingested materials such as vitamins (qv) and sustained release tablets (see Controlled RELEASE technology). 

Sherex, Mapleton, Ik., U.S. 7 oleyl alcohol, -C g tallow, soybean ok... 

Sulfur trioxide reactivity can also be moderated through the use of SO adducts. The reactivity of such complexes is inversely proportional to their stabihty, and consequentiy they can be selected for a wide variety of conditions. Whereas moderating SO reactivity by adducting agents is generally beneficial, the agents add cost and may contribute to odor and possible toxicity problems in derived products. CeUulosic material has been sulfated with SO.—trimethyl amine adduct in aqueous media at 0 to 5°C (16). Sulfur trioxide—triethyl phosphate has been used to sulfonate alkenes to the corresponding alkene sulfonate (17). Sulfur trioxide—pyridine adduct sulfates oleyl alcohol with no attack of the double bond (18). 

Conditioners are compounds added to keep the hair cuticle smooth and slippery. Silicone oils such as dimethicone and cyclomethicone are used to make the hair shiny and slippery. Humectants (moisturizers) like panthenol help keep the cuticle moist so that the scales do not stand up. Long-chain fatty alcohols such as cetyl alcohol, oleyl alcohol, and stearyl alcohol... 

Fatty alcohols were sulfated with concentrated sulfuric acid before World War II, most frequently involving oleyl alcohols or alcohols derived from sperm and whale oil. Low temperatures were often suggested. Oleyl alcohol was sulfated by adding the alcohol to concentrated sulfuric acid, precooled to a temperature only slightly above the melting point of the alcohol [19], or by addition of cooled sulfuric acid (<95.12%) mixed with diethyl ether and phosphorus pentoxide to the alcohol, under constant stirring, for 3 h at 6-7°C, giving a yield of 98% [20]. Oleyl alcohol was also sulfated either by sulfuric acid or by oleum at 15°C [21]. 

The lipophilicity of a solute affects its permeability in lipid bilayers. Lipophilicity is usually expressed in terms of its partitioning between water and an organic solvent, such as olive oil [95], oleyl alcohol [96], ether [97], or octanol [98]. Partition coefficient (PC) of a compound is expressed as its concentration ratio between organic medium and water at equilibrium ... 

Membrane-interactive compounds are lipophilic molecules which have high affinity for lipid membranes and consequently possess long membrane residence times. Examples include the lipophilic neutral molecules (cholesterol, lecithin, pesticides, oleyl alcohol, tocopherols, etc.) and large organic cations (chlorproma-... 

Oleoxyl chloride, ol3 Oleyl alcohol, ol2 Oleylamine, o9 o-Orthanilic acid, al 15 7-Oxabicyclo[2.2.1]heptane, c331b, e7 7-Oxabicyclo[4.1.0]heptane, e6 6-Oxabicyclo[3.1.0]hexane, elO Oxacyclopentane, t69... 

Porogenic solvent Tetradecanol Tetradecanol Tetradecanol Decanol+oleyl alcohol 1 1... 

The prototype reaction was the hydroformylation of oleyl alcohol (water insoluble) with a water-soluble rhodium complex, HRh(C0)[P(m-C6H4S03Na)3]3 (Figure 6.5). Oleyl alcohol was converted to the aldehyde (yield = 97%) using 2 mol % Rh with respect to the substrate and cyclohexane as the solvent, at 50 atmospheres CO/H2, and 100°C. The SAPCs were shown to be stable upon recycling, and extensive work proved that Rh is not leached into the organic phase. Since neither oleyl alcohol nor its products are water soluble, the reaction must take place at the aqueous-organic interface where Rh must be immobilized. Also, if the metal catalyst was supported on various controlled pore glasses with... 

M. J. Rang and C.A. Miller Spontaneous Emulsification of Oils Containing Hydrocarbon, Nonionic Surfactant, and Oleyl Alcohol. J. Colloid Interface Sci. 209, 179 (1999). 

Unsaturated alcohols can be obtained from unsaturated esters under special precautions. Catalytic hydrogenation over zinc chromite converted butyl oleate to oleyl alcohol (9-octadecenol) in 63-65% yield even under very energetic conditions (283-300°, 200atm) [52]. 

Retention in RPC with 34-60% (v/v) methanol-water as the mobile phase has been shown to correlate well to log P by Riley et-aL (192) at each mobile phase composition. A mild dissent has been made by investigators (289) who found a correlation between RPC retention and log P but who claimed a closer relationship between the corresponding data obtained in thin-layer chromatography in the system oleyl alcohol-water and log P (289). 

Escolar and oilfish contain a mixture of wax esters with different carbon-chain length, mainly C32, C34, C36, and C38, formed by combining different fatty acids and fatty alcohols. The dominant fatty acids in escolar and oilfish wax esters are the monounsaturated fatty acids (Table 1.3), namely oleic acid (18 1 oo9) and eicosenoic acid (20 loo9), while the dominant fatty alcohols are saturated and monoenoic fatty alcohols (Table 1.4), known as cetyl alcohol (16 0) and oleyl alcohol (18 1 9). PUFA, which are trace components in muscle wax esters, are commonly found in wax esters from roe, they include 20 4o)6, 20 5(b3, 22 5cd3 and 22 6 3. These differences could be due to the functional role in muscle for providing buoyancy, while that of roe is to store energy and key essential PUFA for fry development (Lee and Patton, 1989). 

Esterification between oleic acid and oleyl alcohol, catalyzed by the Mucor miehei immobihzed hpase in a batch-stirred tank reactor with supercritical carbon dioxide as solvent produced higher reaction rates at supercritical conditions than in the solvent-free system (Knez et al., 1995). 

Oleth-2 Oleyl alcohol Oleyl oleate PEG-10 lanolate PEG-10 methyl ether PEG-16... 

Cetyl alcohol, mono- and di-glycerides, oleyl alcohol, sodium cetostearyl sulphate, stearyl alcohol... 

Lissapol C (mainly sodium salt of cetyl oleyl alcohol sulphate) [2425-51-6],... 

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