Undecynoic acid

Undecylenic acid (or 10-undecenoic acid) (I), a comparatively inexpensive commercial product obtained from castor oil, reacts with bromine in dry carbon tetrachloride to give 10 11-dibromoundecoic acid (II), which upon heating with a concentrated solution of potassium hydroxide yields 10-niidecynoic acid (III)  

The position of the triple bond is established by oxidation of the latter by means of alkaline potassium permanganate solution to sebacic acid, H02C(CH2)gC0jH, m.p. 133°. 

Oxidation of 10-undecynoic acid to sebacic acid. Dissolve 2 00 g. of the acid, m.p. 41-42°, in 50 ml. of water containing 0 -585 g. of pure anhydrous sodium carbonate. Saturate the solution with carbon dioxide and add O IN potassium permanganate solution (about 1500 ml.) slowly and with constant stirring until the pink colour remains for half an hour the addition occupies about 3 hours. Decolourise the solution with a httle sulphur dioxide and filter off the precipitated acid through a 

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Dimethyl-1 3-butadiene Dimethylethynyl carbinol 10-Undecynoic acid. ... 

PHAs containing carbon-carbon triple bonds synthesized by P. oleovorans and P. putida grown with 10-undecynoic acid (10-UND=) have been reported [64]. The amount of carbon-carbon triple bond could be controlled between 0% and 100%, but the yield of the PHA containing 100% carbon-carbon triple bond was very low. The repeating units formed from 10-UND= were 3-hydroxy-8-nonynoate (3HN=) and 3-hydroxy-6-heptynoate (3HHp=) units in the amounts of 26 mol% and 74 mol%, respectively. The glass transition temperatures of PHAs synthesized from mixtures of NA and UND= increased from -30°C to -20°C as the content of carbon-carbon triple bond increased from 0% to 100%. These polymers were crosslinked when cations such as Co2+ and Pt2+ were added. 

The monomer used in our studies was synthesized by Cadiot-Chodkiewicz Coupling (14) of 1-iodooctadecyne and 10-Undecynoic acid. 10 Undecynoic acid was used as received from Farchan Labs... 

Undecenoic acid, 32, 104 M-Undecyl fluoride, 36, 42 10-Undecynoic acid, 32,104 a,/3-Unsaturated acids, purification of,... 

A Long-chain carboxylic acids Laurie acid 10-Undecynoic acid Clofibrate Inducers are usually peroxisome proliferators... 

The water solution containing the sodium salt of the product is acidified with 6 N hydrochloric acid and then extracted with three 200-ml. portions of ether. The ethereal extracts are combined, washed with water (until the aqueous phase shows a pH in the range 5-6), and then dried over anhydrous sodium sulfate. After removal of the solvent, the red-colored residual oil is fractionally distilled through a packed column (Note 6). The middle portion (26-28 g.) distilling at 124-130°/3 mm. is crystallized twice from petroleum ether (b.p. 30-60°) to obtain white crystals of 10-undecynoic acid. The end fractions also yield some white product after 4-5 crystallizations. A total yield of 19-24 g. (38-49%) is obtained m.p. 42.5-43°. 

Undecenoic acid (undecylenic acid, commercial grade) may be obtained from the Eastman Kodak Company. The pure grade acid is also used with good results. However, for general purposes, no difficulty is encountered in preparing 10-undecynoic acid from the commercial grade acid if the final fractionation by vacuum distillation is carried out carefully. 

Undecanoic acid, 32, 104 10-Undecynoic acid, 32, 104 Unsaturation, quantitative estimation by bromate-bromide titration method, 34, 86, 89 Urea, 30, 24 31, 11 Urea, I-(T -bromophenyl)-, 31, 8 1-(o-chlorophenyl)-2-thio-, 31, 21 1,1-dimethyl-, 32, 61 I-(P-phenetyl)-, 31,11... 

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