Oleic acid iodination

Jute seed oil n. Obtained from the seed of Corchorus capsularis, grown chiefly in Indian, Egypt, and China. It contains lino-leic and oleic acids. Iodine value, 103 Sp gr, 0.921/15°C saponification value, 185 acetyl value 27. Langenheim JH (2003) Plant resins chemistry, evolution ecology and ethnobotany. Timber Press, Portland, OR. Paint pigment, drying oils, polymers, resins, naval stores, cellulosics esters, and ink vehicles, vol 3. American Society for Testing and Material, Conshohocken, PA, 2001. 

C-21 dicarboxyhc acids are produced by Westvaco Corporation in Charleston, South Carolina in multimillion kg quantities. The process involves reaction of tall oil fatty acids (TOFA) (containing about 50% oleic acid and 50% hnoleic acid) with acryhc acid [79-10-7] and iodine at 220—250°C for about 2 hours (90). A yield of C-21 as high as 42% was reported. The function of the iodine is apparendy to conjugate the double bond in linoleic acid, after which the acryhc acid adds via a Diels-Alder type reaction to form the cycHc reaction product. Other catalysts have been described and include clay (91), palladium, and sulfur dioxide (92). After the reaction is complete, the unreacted oleic acid is removed by distillation, and the cmde C-21 diacid can be further purified by thin film distillation or molecular distillation. 

Fatty acid Separation of tallow fatty acid into saturated and unsaturated fractions 20,000 Stearic acid Iodine no. 2 Oleic acid Cloud pt 5 C Falling film Japan Undisclosed... 

The major fatty acids present in plant-derived fatty substances are oleic acid (9-octadecenoic, C18 l), linoleic acid (9,12-octadecadienoic, C18 2) and the conjugated isomers thereof and linolenic acid (9,12,15-octadecatrienoic, C18 3) (Scheme 31.1). Their rates of oxygen absorption are 100 40 1, respectively, hence partial hydrogenation with consequent lowering of the iodine number would lead to a significant increase in oxidative stabihty, particularly when C18 3 is reduced. 

Oleic acid Molar mass 03 (0 33002)3 = 885.45 g mol 1 Iodine number for oleic acid mass oft... 

K2. Kaplan, E., Edidin, B. D., Fruin, R. C., and Baker, L. A., Intestinal absorption of iodine 131 labelled triolein and oleic acid in normal subjects and in steatorrhea. Gastroenterology 34, 901-909 (1958). 

The checkers used commercial u.s.p. oleic acid, which has an iodine number of about 60-70 and contains 65-75% oleic acid. The submitters report that, if highly purified oleic acid is used, the yield of fairly pure 9,10-dihydroxystearic acid is almost quantitative, but the purification procedure for oleic acid [Biochem. Preparations, 2, 100 (1952)] is more lengthy and inconvenient than the purification of the hydroxylation product. The over-all yield is approximately the same in either case. 

The methyl oleate was prepared by esterification1 of commercial u.s.p. grade oleic acid and fractionated through a Widmer column. The fractions used boiled at 140-144° (0.5 mm.), 175-179° (2 mm.), and had d 1.4500-1.4527 and an iodine number of 93-97 (calcd. 85.6) by iodine bromide titration.2... 

Is the Iodine Value found in EN 14214 based on science It is certainly not so in an absolute way, but some relation cannot be denied. Frankel (2005) for example clearly states that oxidation stability is a function of two things the number of double bounds, and their position towards one another in the fatty acid. Oleic acid with one double bound oxidizes 40 times slower than linoleic acid with two double bounds, and one bis-allylic position in-between both. Linolenic acid with three double bounds separated with two bis-allylic positions oxidizes only 2.5 times faster than linoleic acid. Oxidation is a radical driven reaction, and the bis-allylic positions are a much more favorable point of attack than the allylic positions next to the double bound. 

Free Fatty Acids (as oleic acid) Not more than 2.5%. Iodine Value Not more than 16. 

Oleic Acid Isolate the fatty acids as directed under Laurie Acid in the monograph for Polysorbate 20, and determine the weight of the acid. With the product so obtained, determine the acid value (between 193 and 206) as directed in Method I under Acid Value, Appendix VII. Similarly determine the iodine value (between 80 and 92) as directed under Iodine Value, Appendix VII. 

Oils with higher iodine value (normally 53, raised to 63) contain less palmitic acid and more oleic acid. When fractionated, they produce more of the valuable olein fraction (Section 5). 

The higher value for canola oil is caused, in part, by the replacement of erucic acid with octadecenoic acids, mainly oleic acid, accompanied by a slight increase in linoleic and linolenic acids (Table 13). The iodine value can also be calculated from fatty acid composition using the specific factors for each unsaturated fatty acid (61). The calculation method provides more accurate data than the iodine absorption assessment. 

The seed of perilla contains 31-51% of oil, which is similar in composition to flaxseed oil, with a higher contribution of PUFA of over 70% (Table 4). The oil is highly unsaturated, with an iodine value of 192-208-g iodine /100-g oil (Table 4). Perilla oil contains over 60% linolenic acid with equal amounts of both linoleic and oleic acids (Table 4). Specific gravity of this oil is higher than flax oil because of a higher contribution of PUFA. Other physical parameters of this oil reflect the composition of its fatty acids. 

Watermelon seed oil was prepared and evaluated for its physicochemical properties (22, 23). The seed oil consisted of 59.6% linoleic acid (18 2n-6) and 78.4% total unsaturated fatty acids (Table 4). The predominant fatty acid in the oil was linoleic acid, which was followed by oleic, palmitic, and stearic acids. Linolenic, palmitoleic, and myristic acids were minor constituents. The refractive index, acid value, peroxide value, and free fatty acids of watermelon seed oil were determined to be 1.4696 (25°C), 2.82 (mg KOH/g oil), 3.40 (mequiv oxygen/kg oil), and 1.41 (% as oleic acid), respectively. The saponification value of watermelon seed oil was 201 (mg KOH/g oil), and its iodine value was 115 (g iodine/100-g oil), which was significantly higher than pumpkin at 109 (g iodine/lOO-g oil) (22, 23). 

Melon, Cucumis melo, is a member of the Cucurbitaceae family and grows best in tropical regions. The pulp of the fruit has pleasant flavor and taste, and the seeds are generally treated as waste however, medicinal effects have been reported for the seeds (24, 25). Hexane-extracted seed oil of Cucumis melo hybrid AF-522 was determined to contain 64 g of linoleic acid per 100 g of total fatty acids (Table 4) (24). Significant amounts of oleic, palmitic, and stearic acids were also detected in the melon seed oil. The specific gravity (28°C), refractive index (28°C), and iodine value of the seed oil were 0.9000, 1.4820, and 112, respectively, under the experimental conditions (24). Earlier in 1986, Lazos (25) extracted the oil from Cucumis melo seeds and examined its physicochemical properties (25). Linoleic acid was the primary fatty acid and accounted for 64.6% of the total fat (w/w), along with 20.1% oleic acid, and 14.7% total saturated fatty acids (Table 4). Iodine value and refractive index (40°) of the seed oil were 124.5 and 1.4662, respectively. 

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