Oleic acid carbonyl compound

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). 

More than 300 compounds had been identified in cocoa volatiles, 10% of which were carbonyl compounds (59,60). Acetaldehyde, 2-methylpropanal, 3-methylbutanal, 2-methylbutanal, phenylacetaldhyde and propanal were products of Strecker degradation of alanine, valine, leucine, isoleucine, phenyl-acetaldehyde, and a-aminobutyric acid, respectively. Eckey (61) reported that raw cocoa beans contain about 50-55% fats, which consisted of palmitic (26.2%), stearic (34.4%), oleic (37.3%), and linoleic (2.1%) acids. During roasting cocoa beans these acids were oxidized and the following carbonyl compounds might be produced - oleic 2-propenal, butanal, valeraldehyde, hexanal, heptanal, octanal, nonanal, decanal, and 2-alkenals of Cg to C-q. Linoleic ethanal, propanal, pentanal, hexanal, 2-alkenals of to C q, 2,4-alkadienals of Cg to C-q, methyl ethyl ketone and hexen-1,6-dial. Carbonyl compounds play a major role in the formation of cocoa flavor components. 

The thermal decomposition of organometallic compounds in high-boiling solvents in the presence of stabilizers has been widely investigated, and is currently used for the synthesis of Fe304 and y-Fe203 nanocrystals. Iron carbonyls [68, 98], acetylacetonate [99] and iron fatty acid salts [100, 101] are the typical precursors, while oleic acid and other fatty acids, as well as oleylamine and other aliphatic amines, are the most frequently used surfactants. The important parameters for controlling... 

Magnetic alloys CoPt and Co particles coated with a shell of Pt have been prepared in [323]. The alloy has been synthesized by adding of carbonyl Co2(CO)g to hot solution of organic solvent containing platinumorganic compound with oleic acid. The decomposition of carbonyl phase forms Co nanoparticles, which react with platinumorganic compound. To obtain the structure of the ferromagnetic... 

The introduction of a reactive functionality into the polymer, such as unsaturation, offers the potential to use organic acids as coupling agents, but mixed results have been reported. A number of potentially suitable unsaturated products exist, notably, maleic acid and anhydride, acrylic and methacrylic adds, and unsaturated versions of fatty acids such as oleic acid. The acidities and double-bond reactivities of these compounds widely vary depending on their structures, and this probably accounts for the marked differences in their performance. Compounds such as acrylic acid have both high addity and high double-bond reactivity due to the proximity of the carbonyl group to the double bond. The only commercial products specifically developed for use with filled polymer systems are from Lubrizol Advanced Materials (SOLPLUS). 

Favorable reaction conditions in the carbonylation of molecules with olefinic double bonds are obtained if the starting compound contains a hydrophilic group, as e. g. in oleic acid, where the solubility of water in the organic layer is increased by the presence of the carboxyl group. Thus, a troublefree reaction course is achieved even in continuous processing. In this case even dicarboxylic acids, instead of the diesters, are obtained in high yield. 

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. ... 

Olefins s. Ethylene derivatives Oleic acid as reagent 16, 867 Onic acids s. Aldonic acids Oppenauer oxidation, preferential 16, 316 Organometallic compounds (s. a. under individual metals. Metal carbonyls, Metal complex compounds, organo-) 16, 635... 

The unsaturated fatty acids in all fats and oils are subject to oxidation, a chemical reaction which occurs with exposure to air. The eventual result is the development of an objectionable flavor and odor. The double bonds and the adjacent allylic functions are the sites of this chemical activity. Oil oxidation rate is roughly proportional to the degree of unsaturation for example, linolenic fatty acid (18 3) with three double bonds is more susceptible to oxidation than linoleic (18 2) with only two double bonds, which is ten or more times as susceptible as oleic (18 1) with only one double bond. Oxidative deterioration results in the formation of hydroperoxides, which decompose into carbonyls, and dimerized and polymerized gums. It is accelerated by a rise in temperature, oxygen pressure, prior oxidation, metal ions, lipoxygenases, hematin compounds, loss of natural antioxidant, absence of metal deactivators, time and ultraviolet or visible light. Extensive oxidation will eventually destroy the beneficial components contained in many fats and oils, such as the carotenoids (vitamin A), the essential fatty acids (linoleic and linolenic), and the tocopherols (vitamin E). 

---