Ricinolic acid

The name ricinoleic acid is used in commerce for the mixture of fatty acids obtained by hydrolysing castor oil, and its salts are called ricinoleates. 

Castor oil (qv) contains a predominance of ricinoleic acid which has an unusual stmcture inasmuch as a double bond is present in the 9 position while a hydroxyl group occurs in the 12 position. The biochemical origin of ricinoleic acid [141-22-0] in the castor seed arises from enzymatic hydroxylation of oleoyl-CoA in the presence of molecular oxygen. The unusual stmcture of ricinoleic acid affects the solubiUty and physical properties of castor oil. 

Castor Oil. Castor oil [8001-79-4] (qv) is the fixed oil from the seeds of Picinus communis Linne. Pale yellowish or almost colorless, it is a transparent viscid Hquid with a faint, mild odor and a bland taste followed by a slightly acrid and usually nauseating taste. Its specific gravity is between 0.945 and 0.965. Castor oil is soluble in alcohol, and miscible with anhydrous alcohol, glacial acetic acid, chloroform, and diethyl ether. It consists chiefly of the glycerides of ricinoleic acid [141 -22-0], and isoricinoleic acid [73891-08-4], found in the small intestine. The seed contains a highly... 

Castor oil is a cathartic only after Hpolysis in the small intestine Hberating ricinoleic acid. Ricinoleic acid inhibits the absorption of water and electrolytes. It is commonly used for preparation of the large bowel for diagnostic procedures. 

Amide yields of up to 90—95% are reported from lauric acid and urea (1 1 mole ratio) by ramping the reaction temperature from 140 to 190°C over 4 hours. Oleic, stearic, linoleic, and ricinoleic acids gave similar results (19,20). The reaction does not form significant quantities of bisamides, but rehes on the decomposition of a substituted urea amide, releasing CO2 and NH. ... 

Sulfated Natural Oils and Fats. Sulfated natural triglycerides were the first nonsoap commercial surfactants introduced in the middle of the nineteenth century. Since then sulfates of many vegetable, animal, and fish oils have been investigated (see also Fats AND FATTY oils). With its hydroxyl group and a double bond, ricinoleic acid (12-hydroxy-9,10-octadecenoic acid) is an oil constituent particularly suited for sulfation. Its sulfate is known as turkey-red oil. Oleic acid is also suited for sulfation. Esters of these acids can be sulfated with a minimum of hydrolysis of the glyceride group. Polyunsaturated acids, with several double bonds, lead to dark-colored sulfation products. The reaction with sulfuric acid proceeds through either the hydroxyl or the double bond. The sulfuric acid half ester thus formed is neutralized with caustic soda ... 

Many substituted, ie, branched, fatty acids, particularly methacryUc, 2-ethylhexanoic, and ricinoleic acids, are commercially significant. Several substituted fatty acids exist naturally (Table 5). Fatty acids with a methyl group in the penultimate position are called iso acids, and those with a methyl group in the antepenultimate position are called anteiso acids (1) (see Carboxylic acids, branched-CHAIN acids). However, the term iso is often used in a broader sense to mean branched or mixtures of branched-chain industrial acids. 

Pyrolysis is used to produce undecenoic acid from ricinoleic acid ... 

Castor oil sulfation results largely in a sulfuric acid ester in which the hydroxyl group of ricinoleic acid has been esterified. However, other reactions can also take place. For example, the double bond can be attacked to produce an ester or the hydroxysulfonic acid (33). Hydrolysis of the sulfuric acid esters occurs during the reaction and subsequent treatment forming hydroxy acids and sulfuric acid. These hydroxy acids can be further sulfated. 

Pyrolytic Decomposition. The pyrolytic decomposition at 350—460°C of castor oil or the methyl ester of ricinoleic acid spHts the ricinoleate molecule at the hydroxyl group forming heptaldehyde and undecylenic acids. Heptaldehyde, used in the manufacture of synthetic flavors and fragrances (see Elavors and spices Perfumes) may also be converted to heptanoic acid by various oxidation techniques and to heptyl alcohol by catalytic hydrogenation. When heptaldehyde reacts with benzaldehyde, amyl cinnamic aldehyde is produced (see Cinnamic acid, cinnamaldehyde, and cinnamyl... 

Polymerization of castor od, chemical or oxidative, results in higher viscosity or bodied ods that are more usehd in urethane coatings than the untreated castor od (87). Other castor derivatives used to prepare urethanes are amides prepared by reaction of castor od and alkanolamines, amides of ricinoleic acid with long-chain di- and triamines, and butanediol diricinoleate (88,89). 

Sebacic Acid. This acid is produced commercially by Union Camp in Dover, Ohio, by Hokoku OU Company in Japan, and by a state enterprise in the People s RepubHc of China (57). The process used in each case is based on the caustic oxidation of castor oU or ricinoleic acid [141-22-0] in... 

Ricinoleic acid (dl 12-hydroxyoleic acid) [14I-22-0J M 298.5, m 7-8° (a-form), 5.0° (7-form), n 1.4717, pKe, -4.5. Purified as methyl acetylricinoleate [Rider J Am Chem Soc 53 4130 1931], fractionally distilling at 180-185°/0.3mm, then 87g of this ester was refluxed with KOH (56g), water (25mL), and MeOH (250mL) for lOmin. The free acid was separated, crystd from acetone at -50°, and distd in small batches, b 180°/0.005mm. [Bailey et al. J Chem Soc 3027 1957.]... 

Sebacic acid is normally made from castor oil, which is essentially glyceryl ricinoleate. The castor oil is treated with caustic soda at high temperature, e.g. 250°C, so that saponification, leading to the formation of ricinoleic acid is followed by a reaction giving sebacic acid and octan-2-ol Figure 18.5. 

The starting point for this amino acid, from which nylon 11 is obtained, is the vegetable product castor oil, composed largely of the triglyceride of ricinoleic acid. This is first subjected to treatment with methanol or ethanol to form the appropriate ricinoleic acid ester. 

Ricinus, m. castor-oil plant, -ijl, n. castor oil. -(ilsaure, /. ricinoleic acid. -Slseife, /. caator-soap, -olsulfosaure, /. castor-oil sulfonic acid, -samen, m. castor bean, -saure, /. ricinic (ricinoleic) acid, -seife, /. castor-oil soap. 

Ricinoleic acid carstor oil. Argot oil Meconic acid Papaveraceaa... 

Oleic acid, linolic acid, ricinolic acid, and 2-bromostearic acid methyl ester as well are reacting with diethyl phosphite in the presence of benzoyl peroxide to the corresponding phosphono fatty acid esters [156-158]. 

The important but unusual fatty acid ricinoleic acid, or 12-hydroxyoleic acid, is a major component of castor oil (>87%) and is also found in useful quantities in ergot. The metal salts of the acid find use in dry-cleaning soaps but the majority is converted to aminoundecanoic acid (Scheme 6.6) which is used to make nylon 11. Nylon 11 has very good chemical and shock-resistance properties, which have led to it being used in the automotive industry. Ricinoleic triglyceride is initially transesterified to the methyl ester. This is heated to 300 °C at which temperature it is... 

Scheme 6.6 Conversion of ricinoleic acid into aminoundecanoic acid...

HDZ = hydrazine Igepal CO-520 = polyoxyethylene(5)nonylphenyl ether ISO = isooctane LAc = linoleic acid MA = methylamine MST = mesitylene Ni°(cod)2 = bis (r]4-l,5-cyclooctadiene) Ni(0) NMPyr = N-methylpyrrole OA = oleylamine OAc = oleic acid Oc = octane OcA = octylamine ODA = octadecylamine PAA = poly (acrylic add) PD = 2-pyrrolidone Igepal CA-520 = polyoxyethylene(5)isooctylphenyl ether PVP = polyvinylpyrrolidone Pyr = pyrrole RAc = ricinoleic acid ... 

Nevertheless, there are some vegetable oils that have a very specific composition. For example, castor oil consists of large amounts (83 89%) of 12-hydroxy-(Z)-9-octadecenoic acid (ricinoleic acid) which is not found in other natural lipids [21]. Ricinoleic acid produces a very characteristic oxidation product, 9,12-dihydroxyoctadecanoic acid [43], and both of these compounds can be considered as specific biomarkers for castor oil and have been used to assess its presence in ceramic lamps [43] and mummification balms [23]. 

Hydroxyoctadecanoic (ricinoleic) acid, 9,12 dihydroxyoctadecanoic acid Castor oil [1 7,44]... 

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