Ricinoleic acid forms

DCO n. Non-drying castor oil which has been converted into a drying oil by the catalytic removal of water from its principal fatty acid (80% ricinoleic acid), forming approximately equal quantities with 9-11 and 9-12 unsaturation. The term DCO... 

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 ... 

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... 

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.]... 

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. 

It can be prepared by heating castor oil with NaOH at 250°C. During the reaction ricinoleic acid is produced which forms octane-2-ol and sebacic acid ... 

It can be obtained from castor oil. Methanolysis of castor oil yields methylester of ricinoleic acid. Pyrolysis at 500°C forms n-heotaldehyde and methyl-undecylenate. Hydrolysis of latter... 

Castor oil [CO Structure (4.3)] is a triglyceride of ricinoleic (12-hydroxyoleic) acid about 90% of the fatty acid portion of the molecule consists of ricinoleic acid and 10% in the form of non-hydroxy acids consisting largely of oleic and linoleic acids. Small amounts of stearic and dihydroxystearic acids are also found in some industrial grades. 

The origin of ricinoleic acid, an abundant constitu-tuent of castor beans, is also shown in Fig. 21-2. It is formed by an oleate hydroxylase that has an amino acid sequence similar to those of oleate desaturases.113 Both hydroxylation and desaturation are reactions catalyzed by diiron centers.114 Other fatty acid hydroxylases act on the alpha115 and the omega positions. The latter are members of the cytochrome P450 family.116 117... 

Ricinoleic acid (Figure 3.8) is the major fatty acid found in castor oil from seeds of the castor oil plant (Ricinus communis Euphorbiaceae), and is the 12-hydroxy derivative of oleic acid. It is formed by direct hydroxylation of oleic acid (usually esterified as part of a phospholipid) by the action of an 02- and NADPH-dependent mixed function oxidase, but this is not of the cytochrome P-450 type. Castor oil has a long history of use as a domestic purgative, but it is now mainly employed as a cream base. Undecenoic acid (A9-undecenoic acid) can be obtained from ricinoleic acid by thermal degradation, and as the zinc salt or in ester form is used in fungistatic preparations. 

Figure 25.3. Ion trap mass spectrum of ESI-MS3 of [ROR + Li - ROOH]+ at m/z 625.5. For abbreviations, see Figure 25.2. 0 CH=CHC00H is a,p-unsaturated oleic acid from the sn-2 position. R CH=CHCOOH is a,p-unsaturated ricinoleic acid from the sn-2 position. C7H14O is the loss from the cleavage between C-ll and C-12 of ricinole-ate chain. C3H40 is the loss of glycerol backbone to form acid anhydride of two fatty acids. R"CH=C=0 is a ketene from ricinoleate at the sn-1,3 position.

To evaluate the in-vivo gelation mechanism of the polymer, mice were injected with three different volumes of polymer. The polymer remained at the injection site and maintained its shape for 24h post injection as happens when oil is injected in the subcutaneous space. Based on data presented in this work we can classify poly(sebacic-co-ricinoleic acid) as in-situ organogel forming. 

Liquid polyesters are formed when the feed ratio of ricinoleic acid is higher than 30% for polycondensation and 50% for transesterification. Polyesters synthesized by ring opening polymerization are solid at room temperature. These polyesters were evaluated as drug carriers for two drugs 5FU and triamcinolone in vitro. Both drugs were released for over two weeks (34),... 

Fatty acids with trans or non-methylene-interrupted unsaturation occur naturally or are formed during processing for example, vaccenic acid (18 1 Hr) and the conjugated linoleic acid (CLA) rumenic acid (18 2 9tllc) are found in dairy fats. Hydroxy, epoxy, cyclopropane, cyclopropene acetylenic, and methyl branched fatty acids are known, but only ricinoleic acid (12(/f)-hydroxy-9Z-octadecenoic acid) (2) from castor oil is used for oleochemical production. OUs containing vernolic acid (12(5),13(/ )-epoxy-9Z-octadecenoic acid) (3) have potential for industrial use. 

Figure 15. Schematic model of polymorphic structures of SRS and SLS. (a) A postulated structure of p forms of SRS, in which a ricinoleic acid leaflet is shown, (b) Polymorphic...

Iodine dissolves very readily in the non-polar solvent paraffin and its violet color is seen in the uppermost phase. The middle layer consists of castor oil, which is naturally colored light yellow as an ester of ricinoleic acid it can also dissolve small amounts of iodine with the formation of a yellow color. The blue copper sulfate solution forms the lower layer because of its higher density. 

Candida strains convert ricinoleic acid into If-decalactone, which displays the fatty, fruity aroma typical of peaches. Ricinoleic acid (12-hydroxy octadec-9-enoic acid) is the major fatty acid in castor oil (approx. 80 %). The yeast can lipolyze castor oil glycerides and the liberated ricinoleic acid is subsequently metabolized via d-oxidation and eventually converted to 4-hydroxy-decanoic acid (Figure 5). Recently a European patent has been filed (20) essentially covering the same procedure. Shake culture fermentations were carried out on 100 ml scale for one week. The 4-hydroxydecanoic acid formed was converted to )f-decalactone by boiling the crude, acidified (pH 1.5) fermentation broth for a period of 10 minutes. The lactone was isolated via solvent extraction and a yield of some 5 g/1 was obtained. The same lactone was detected as the major volatile component formed when the yeast, Sporobolomyces odorus was grown in standard culture medium (21). Although the culture medium displayed an intense fruity, typical peach-like odor, the concentration of y-decalactone amounted to no more than 0.5 mg/1. 

Enzymes can be used to selectively hydrolyze only one of two ester groups in a molecule. An esterase from Pseudomonas putida was used to hydrolyze dimethyl adipate to more that 99% half ester.198 Pig liver esterase was used to hydrolyze dialkyl phthalates to the monoesters in 84-93% yields in 1-13 h.199 A porcine pancreatic lipase was used to hydrolyze linear diol diacetates to the monoacetates in 79-95% yields.200 Esters have been prepared from 12-hydroxystearic acid and C8-C18 alcohols in 82-90% yields without esterification of the 12-hydroxy group, by using an immobilized lipase from Rhizomucor miehei.201 Ricinoleic acid, which differs only by having a cis 9 double bond, formed oligomers with an immobilized lipase from C. rugosa.202 These were much less colored than the ones made by the commercial process, which is done at 200 C. 

Castor oil and the hydrolysis product - ricinoleic acid are a source of new valuable products. Thus, by the caustic oxidation of ricinoleic acid, sebacic acid and 2-octanol are formed. By hydrogenation of sebacic acid (or better of dimethylsebacate), 12-decanediol is formed. By hydrogenation of ricinoleic acid an interesting diol is obtained 1,12 hydroxystearyl alcohol having one primary and one secondary hydroxyl group (reaction 17.11). 

The stabilizer systems for polyacetals are invariably composed of a hindered phenol with a costabilizer. The hindered phenols in use are 2,2 -methylenebis-(4-methyl-6-tert-butyl-phenol), 1,6-hexamethyle-nebis-3-(3,5-di-rert-butyl-4-hydroxyphenyl)-propionate, and pentaerythrityl-tetrakis-3-(3,5-di-fert-butyl-4-hydroxyphenyl)-propionate. A large number of nitrogen-containing organic compounds have been described as costabiKzers for polyacetals, e.g., dicyandiamide, melamine, terpolyamides, urea, and hydrazine derivatives. The effectiveness of these compounds is based on their ability to react with formaldehyde and to neutralize acids, especially formic acid, formed by oxidation. In addition to nitrogen compounds, salts of long-chain fatty acids (e.g., calcium stearate, calcium ricinoleate, or calcium citrate) are also used as acid acceptors. The practical concentrations are 0.1-0.5% for the phenolic antioxidant and 0.1-1.0% for the costabilizer. 

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