Capric

By increasing the molar proportion of the monocarboxylic acid, the yield of (II) is improved. Thus electrolysis of a mixture of decanoic acid (n-decoic acid capric acid) (V) (2 mols) and methyl hydrogen adipate (VI) (1 mol) in anhydrous methanol in the presence of a little sodium methoxide gives, after hydrolysis of the esters formed, n-octadecane (VII), tetradecanoic or myristic acid (VIH) and sebacic acid (IX) ... 

Fats and oils may be synthesized in enantiomerically pure forms in the laboratory (30) or derived from vegetable sources (mainly from nuts, beans, and seeds), animal depot fats, fish, or marine mammals. Oils obtained from other sources differ markedly in their fatty acid distribution. Table 2 shows compositions for a wide variety of oils. One variation in composition is the chain length of the fatty acid. Butterfat, for example, has a fairly high concentration of short- and medium-chain saturated fatty acids. Oils derived from cuphea are also a rich source of capric acid which is considered to be medium in chain length (32). Palm kernel and coconut oils are known as lauric oils because of their high content of C-12 saturated fatty acid (lauric acid). Rapeseed oil, on the other hand, has a fairly high concentration of long-chain (C-20 and C-22) fatty acids. 

Substitutes. As of this writing, only one fat substitute, caprenin, a triglyceride composed of capric acid [334-48-5] capryUc acid... 

Many primary fatty amides which are available from various manufacturers are Hsted in Table 3. In 1986 approximately 55,000 metric tons of amides and bisamides were produced world wide (58), the majority of which are bisamides, followed in volume by primary amides. Most of these products are shipped in sohd form in bag or dmm quantities. Major producers of primary fatty amides are Akzo, Glyco, Humko, and Sherex. Bisamides are produced by Akzo, Milacron, and Syntex. There are over 100 producers of alkanolamides in the world, most of which are small specialized manufacturers to a specific industry. GAP, Henkel, Sherex, and Witco are among the principal producers. The most widely used alkanolamides are the Ai,Ai-bis(2-hydroxyethyl) fatty amides, mostly produced from middle-cut coco fatty acids (6% capryflc, 7% capric, 51% lauric, 19% myristic, 9% palmitic, and 2% stearic acids). An estimated 77,000 metric tons of alkanolamide was produced worldwide in 1986 (59). 

Four columns are needed to produce the desired products. Considering the Sharp Distillation Sequencing heuristics, heuristic (/) does not apply, as there is more than one product in this mixture. Fatty acids are moderately corrosive, but none is particularly more so than the others, so heuristic (2) does not apply. The most volatile product, the caproic and capryflc mixture, is a small (10 mol %) fraction of the feed, so heuristic (3) does not apply. The least volatile product, the oleic—stearic acids, is 27% of the feed, but is not nearly as large as the capric—lauric acid product, so heuristic (4) does not apply. The spht between lauric and myristic acids is closest to equimolar (55 45) and is easy. Therefore, by heuristic (5) it should be performed first. The boiling point list implies that the distillate of the first column contains caproic, capryflc, capric, and lauric acids. This stream requires only one further separation, which by heuristic (/) is between the caproic—capryflc acids and capric—lauric acids. 

Capric acid (decanoic acid) [334-48-5] M 172.3, m 31.5 , b 148 /llmm, d 0.886, n s 1.424, pKesi -4.9. Purified by conversion to its methyl ester, b 114.0 /15mm (using excess MeOH, in the presence of H2SO4). After removal of the H2SO4 and excess MeOH, the ester was distd under vacuum through a 3ft... 

Alternatively, purified via its methyl ester (b 140.0°/15mm), as described for capric acid. Also purified by zone melting. 

Myristic acid (tetradecanoic acid) [544-63-8] M 228.4, m 58 , pK 6.3 (50% EtOH), pK si -4.9 (H2O). Purified via the methyl ester (h 153-154 /10mm, n 1.4350), as for capric acid. [Trachtman and Miller y/4m Chem Soc 84 4828 7962.] Also purified by zone melting. Crystd from pet ether and dried in a vacuum desiccator containing shredded wax. 

Chemical Designations - Synonyms Aldehyde C-10 Capraldehyde Capric Aldehyde Decanal n-Decyl Aldehyde Chemical Formula CH3(CH2)gCHO. 

Chemical Designations - Synonyms Alcohol C-10 Capric Alcohol 1-Decanol Dytol S-91 Lorol-22 Nonylcarbinol Chemical Formula CH3(CHj)gCH20H. 

Pimelic Acid (Heptanedioic Acid or 1,5-Pentane-dicarboxytlc Acid). HOOC.(CH2)s.COOH mw 160.17 white prisms mp 106° bp 272° at 100mm (subl), and 212° at 10mm d 1.329 g/cc at 15°. Sol in w, ethanol, eth and hot benz. Prepn is by oxidn of cycloheptanone, capric acid or oleic acid treatment of salicylic acid with Na in amyl ale, or by decarboxylating 1,1,5,5-pentanetetracarboxylic acid with heat Pimelic acid has been combined with cis and trans-, 4-cyclohexanediol to give polyesters, and with m-xylene-ce,ol -diamine or poly-methylenediamines to form polyamides. With diperoxides, the acid forms resins. It is also used as the parent compd to form the expls presented below... 

C Q q — capric acid, Cj2 q = lauric acid, C14 0 = myristic acid, C 16.0 palmitic acid, CIg0 = stearic acid, CIg, = oleic acid, CIg 2 = linolic... 

Soaps are composed of sodium salts of various fatty acids. These acids include those with the general structure CH3-(CH2) -COOH where n = 6 (caprylic acid), 8 (capric acid), 10 (lauric acid), 12 (myristic acid), 14 (palmitic acid), and 16 (stearic acid). Oleic acid (CH3-(CH2)7-CH=CH-(CH2)7-COOH) and linoleic acid (CH3-(CH2)4-CH=CH- H2-CH=CH-(CH2)7-COOH) are also common soap ingredients. These sodium salts readily dissolve in water, but other metal ions such as Ca2+ and Mg2+ form precipitates with the fatty acid anions. For example, the dissolution of the sodium salt of lauric acid and the subsequent formation of a precipitate of the lauric acid anion with calcium ion is given by... 

Completely negative results on the formation of liver glycogen were obtained when the sodium salts of caproic or caprylic acid61 60 were fed, as well as after the administration of the ethyl esters of caproic, caprylic, capric, myristic or oleic acids or methyl laurate.81 Caproic acid was found to be ineffective as a D-glucose-former in the phlorizinized dog.89... 

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