Oleic acid derivatives

Poly(3HAMCL)s have also been produced from free fatty acid mixtures derived from industrial by-products which are potentially interesting low-cost renewable resources. Isolation and analysis of the polymer allowed the identification of 16 different saturated, mono-unsaturated and di-unsaturated monomers [46]. Except for the presence of diene-containing monomers and a large number of minor components, the composition of the fatty acid mixture derived PHA did not differ significantly from oleic acid derived PHAs. 

The results of this test demonstrated that the diamides of the Ci4 and higher saturated fatty acids were water repellents. On the other hand, the unsaturated oleic acid derivatives enhanced hydrophilicity. 

The reaction product was (as an oleic acid derivative) very light-coloured and consisted of ... 

Triethanolamine, an oleic acid derivative with cerumen-olytic properties, is used in impacted cerumen. 

C18H28O5, Mr 324.42. Oleic acid derivative from injured fruit bodies of the chanterelle (Cantharellus ci-barius, Basidiomycetes). The corresponding ( )-10-hydroxy-8-decenoic acid was isolated from C. tubae-formis. 

Miyata and co-workers have compared stearic and oleic acid derived coatings on magnesium hydroxide fillers in polypropylene and found better impact strength for the oleic acid treatment [25]. The reason for this is unclear and the results do not appear to have been confirmed by others. Nevertheless, some commercial magnesium hydroxides are coated with unsaturated acids similar to oleic, suggesting that there may be a real benefit from its use in some circumstances. 

The molecular weight of the fatty acid may be determined by titration or gas chromatography. Its iodine value may also be determined, since acyl taurates and methyltaurates are often oleic acid derivatives. 

The technique involves partition of a solute between a stationary and a mobile phase as in GC, except that in the former both phases are liquids the term "reversed-phase" implies that the mobile phase is more polar than the stationary one. By far the most widely used stationary phase consists of octadecylsilyl C Cie" or "ODS") groups, linked to a silanol surface by covalent bonds, although Cs phases are increasingly being found to have some utility. Invariably, unsaturated fatty acids are eluted appreciably ahead of the saturated fatty acids of the same chain-length, each double bond reducing the retention time (or volume) by the equivalent of about two carbon atoms. Thus oleic acid derivatives tend to elute in the same region as palmitate as these are always major components of plant and animal... 

Table 1. High-oleic oils (>74% oleic acid) derived from rapeseed/canola, sunflower, soybean, and safflower oils ...

High yields are obtained if 80-90% oleic acid (derived from high-oleic -> sunflower) is used. 

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). 

Unhardeaed whole cut tallow and palm acids contain 40—45% oleic acid, which is derived by separation technology. This used to be done by a pressing technique thereby the terminology pressed stearics. In the 1990s the separation is done usiag solvents and/or refrigeration techniques. Oleic and pressed stearics account for about one-third of all U.S. acid production. 

C-19 dicarboxyhc acid can be made from oleic acid or derivatives and carbon monoxide by hydroformylation, hydrocarboxylation, or carbonylation. In hydroformylation, ie, the Oxo reaction or Roelen reaction, the catalyst is usually cobalt carbonyl or a rhodium complex (see Oxo process). When using a cobalt catalyst a mixture of isomeric C-19 compounds results due to isomerization of the double bond prior to carbon monoxide addition (80). 

About 50% of isopropanol use is to produce acetone. Other important synthetic uses are to produce esters of many acids, such as acetic (isopropyl acetate, solvent for cellulose nitrate), myristic, and oleic acids (used in lipsticks and lubricants). Isopropylpalmitate is used as an emulsifier for cosmetic materials. Isopropyl alcohol is a solvent for alkaloids, essential oils, and cellulose derivatives. 

Most of the inhibitors in use are organic nitrogen compounds and these have been classified by Bregman as (a) aliphatic fatty acid derivatives, b) imidazolines, (c) quaternaries, (d) rosin derivatives (complex amine mixtures based on abietic acid) all of these will tend to have long-chain hydrocarbons, e.g. CigH, as part of the structure, (e) petroleum sulphonic acid salts of long-chain diamines (preferred to the diamines), (/) other salts of diamines and (g) fatty amides of aliphatic diamines. Actual compounds in use in classes (a) to d) include oleic and naphthenic acid salts of n-tallowpropylenediamine diamines RNH(CH2) NH2 in which R is a carbon chain of 8-22 atoms and x = 2-10 and reaction products of diamines with acids from the partial oxidation of liquid hydrocarbons. Attention has also been drawn to polyethoxylated compounds in which the water solubility can be controlled by the amount of ethylene oxide added to the molecule. 

A1 soap in which about 50% of the org adds are derived from coconut oil, 25% from naphthenic acids and 25% from oleic acid. When stirred into gasoline at a temp range from 16—29°, M1 swells until the entire vol of gasoline becomes a more or less homogeneous gel M2 Thickener. A standard (for US Air Force) incendiary oil thickener. It is an intimate mixt of 95%Ml Thickener and 5% devolatilized silica... 

Certain long-chain unsaturated fatty acids of metabolic significance in mammals are shown in Figure 23-1. Other C20, C22, and C24 polyenoic fatty acids may be derived from oleic, linoleic, and a-flnolenic acids by chain elongation. Palmitoleic and oleic acids are not essential in the diet because the tissues can introduce a double bond at the position of a saturated fatty acid. 

The major fatty acids present in plant-derived fatty substances are oleic acid (9-octadecenoic, C18 l), linoleic acid (9,12-octadecadienoic, C18 2) and the conjugated isomers thereof and linolenic acid (9,12,15-octadecatrienoic, C18 3) (Scheme 31.1). Their rates of oxygen absorption are 100 40 1, respectively, hence partial hydrogenation with consequent lowering of the iodine number would lead to a significant increase in oxidative stabihty, particularly when C18 3 is reduced. 

Table I shows the composition of lipo-PGEj. Oleic acid was used to improve the stability of PGEj. Glycerol was added to make the water phase isotonic. Isocarbacyclin, a prostacyclin derivative (TEI9090), was incorporated into the lipid microspheres (lipo-PGI2) in a similar composition except for the use of oleic acid.

Biosynthesis of Unsaturated Fatty Acids. In the mammalian tissues, the forma-tion of monoene fatty acids is only possible. Oleic acid is derived from stearic acid, and palmitooleic acid, from palmitic acid. This synthesis is carried out in the endoplasmic reticulum of the liver cells via the monooxigenase oxidation chain. Any other unsaturated fatty acids are not produced in the human organism and must be supplied in vegetable food (plants are capable of generating polyene fatty acids). Polyene fatty acids are essential food factors for mammals. 

Other octadecenoic acids carrying hydroxyl groups in the chain are present in the considered time range their formation derives from the oxidation of the unsaturated Cl8 FAs linoleic acid, linolenic acid and oleic acid. 

Figure 11.9 Pyrogram of a paint sample collected from sixteenth century wall paintings in the Messer Filippo cell of the tower in Spilamberto, Italy. Pyrolysis was performed with a micro furnace pyrolyser, at 600°C, in the presence of HMDS. 1, Carbohydrate pyrolysis products 2, lauric acid 3, suberic acid 4, levoglucosane 5, azelaic acid 6, miristic acid 7, hexadecanenitrile 8, palmitic acid 9, octadecanenitrile 10, oleic acid 11, stearic acid. TMS derivative [74]...

As mentioned earlier, oxidation of LDL is initiated by free radical attack at the diallylic positions of unsaturated fatty acids. For example, copper- or endothelial cell-initiated LDL oxidation resulted in a large formation of monohydroxy derivatives of linoleic and arachi-donic acids at the early stage of the reaction [175], During the reaction, the amount of these products is diminished, and monohydroxy derivatives of oleic acid appeared. Thus, monohydroxy derivatives of unsaturated acids are the major products of the oxidation of human LDL. Breuer et al. [176] measured cholesterol oxidation products (oxysterols) formed during copper- or soybean lipoxygenase-initiated LDL oxidation. They identified chlolcst-5-cnc-3(3, 4a-diol, cholest-5-ene-3(3, 4(3-diol, and cholestane-3 3, 5a, 6a-triol, which are present in human atherosclerotic plaques. 

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