Oxygen Pelargonic acid

It results from oxidative cleavage of - oleic acid and is produced in commercial quantities mainly by ->ozonolysis (2% ozone in a stream of oxygen - pelargonic acid as a diluent 25-40°C ozonides... 

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. 

The trend is toward oxidants that are relatively harmless and that generate no noxious by-products. Oxygen, and materials derived from it, are examples. Ozone is quite toxic itself, but produces no harmful by-products. It is used commercially for the cleavage of oleic acid to azelaic and pelargonic acids.158 Hydrogen peroxide is made from oxygen (4.23).159... 

More drastic oxidation of the ethylenic bonds of oleic, linoleic, and similar unsaturated fatty acids causes the action to go beyond the formation of oxygenated groups and to result in rupture of the bond as well as in oxidation. Such agents as the dichromates, permanganates, and nitric acid may be used to obtain the effect. Thus, oleic, dihydroxystearic, and sterolic acids yield azelaic and pelargonic acids, products that may be further oxidized if the reaction is forced. 

Azelaic acid (nonanedioic) is produced along with pelargonic acid (nonanoic) by ozonolysis of oleic acid. Oleic acid mixed with nonanoic acid is fed into an ozone absorber against a flow of oxygen gas containing about 2% of ozone. Ozonation occurs at 25-45 °C and external cooling is required. The product is decomposed and oxidized in another vessel at 100 °C (Section 10.4.3). The product is distilled to remove nonanoic and other low-boiling acids and azelaic acid is recovered from the residue by extraction with hot water in which it is soluble. 

Formation of lead soaps appears to be the mechanism by which lead-based paints inhibit corrosion of clean steel. When formulated with linseed oil, lead reacts with components of the oil to form soaps in the cured film in the presence of water and oxygen, these soaps degrade to, among other things, salts of a variety of mono- and di-basic aliphatic acids. The lead salts of azelaic, suberic, and pelargonic acid act as corrosion inhibitors lead azelate is of particular importance in LBP. These acids may inhibit corrosion by bringing about the formation of insoluble ferric salts, which reinforce the metal s oxide film until it becomes impermeable to ferrous ions, thus suppressing the corrosion mechanism. 

The intermediate from this initial attack on a double bond is an ozonide as shown generally in Figure 1. Due to the high oxygen content of this intermediate, it is not stable and spontaneously decomposes to a mixture of carbonyl compounds. Various carboxylic acid and aldehyde derivatives of vegetable oils have been prepared in the past by such ozonolysis reactions and this process was commercialized by Emery Industries to manufacture azelaic and pelargonic acids from oleic acid. ... 

Vicinal diols are also oxidized to carboxylic acids. 1,2-Dihydroxydec-ane in benzonitrile shaken with oxygen at atmospheric pressure at 100 °C in the presence of cobalt laurate as a catalyst furnishes, after 2 h, a 66% yield of pelargonic (nonanoic) acid [69]. Electrolysis at 20-30 °C in aqueous potassium carbonate with nickel electrodes in an undivided cell and a current of 0.3 A yields 74-84% of dicarboxylic acids from both cis and trans cyclic diols having six to eight carbons in the rings (equation 307) [122]. 

Typical basic pigments include basic lead carbonate, basic lead sulfate, red lead, and zinc oxide. The soaps formed when these materials Interact, for example, with linseed oil, are oxidized in the presence of water and oxygen to form mono- and dibasic straight chain Cy to Cg acids. Materials of this type (e.g., sodium and calcium azelate and pelargonate) are known to inhibit corrosion. Inhibition is associated with formation of complex ferric salts that reinforce the oxide film. Lead salts act at lower concentration than the sodium or calcium salts (3, 41). 

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