Sodium sebacate

Molecular mass determinations indicated that the diaryl tellurium phthalates are dimeric. With sodium sebacate only oligomeric products were obtained. 

CH3(CH2)5CH0HCH3 + NaOOC(CH2)gCOONa-2-Octanol Sodium Sebacate... 

Fig, 4. Diagram of two-compartment electrodialyzer for production of sebacic acid from sodium sebacate, C = cation-exchange membrane. 

TABLE 1. Electrodialysis of Sodium Sebacatewith Cation-Exchange and Asbestos Diaphragms [26] The Anolyte is a 4.5% Solution of Sodium Sebacate, the Catholyte is 0.1 N Caustic Soda Solution, and the Anode is Platinum... 

The diester is then saponified by boiling with an aqueous solution of caustic soda to form sodium sebacate ... 

The proposed method of electrodialysis provides for electrolysis of a comparatively dilute solution of sodium sebacate (3,7-4.5%), and this clearly prevents oxidation of the sebacate anions in spite of the fact that platinum is recommended as anode [26], The cathode compartment of the electrodialyzer is filled with 1.07 N caustic soda, solution. The diaphragm is a cation-exchange membrane made from sulfonated polystyrene and divinylbenzene, reinforced with polyethylene film. As the sodium ions migrate from the anode to the cathode compartment the free sebacic acid, being poorly soluble, precipitates in the form of a white deposit in the anode compartment and falls to the bottom of the electrolyzer, which prevents it from being oxidized at the anode. 

Diethyl sebacate. Method A. Reflux a mixture of 100 g. of sebacic acid, 81 g. (102-5 ml.) of absolute ethyl alcohol, 190 ml. of sodium-dried benzene and 20 g. (11 ml.) of concentrated sulphuric acid for 36 hours. Work up as for Diethyl Adipate. B.p. 155-156°/6 mm. Yield 114 g. 

Method B. Reflux a mixture of 101 g. of sebacic acid, 196 g. (248 ml.) of absolute ethjd alcohol and 20 ml. of concentrated sulphuric acid for 12 hours. Distil oft about half of the alcohol on a water bath dilute the residue with 500-750 ml. of water, remove the upper layer of crude ester, and extract the aqueous layer with ether. Wash the combined ethereal extract and crude ester with water, then with saturated sodium bicarbonate solution until effervescence ceases, and finally with water. Dry with anhydrous magnesium or sodium sulphate, remove the ether on a water bath, and distil the residue under reduced pressure. B.p. 155-157°/6 mm. Yield llOg. 

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... 

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) ... 

Sebacic acid. Dissolve 40 g. of methyl hydrogen adipate in 100 ml. of absolute methanol to which 01 g. of sodium has been added. Pass a current of about 2 0 amps, until the pH of the solution is about 8 (ca. 5 hours) test with B.D.H. narrow-range indicator paper. Transfer the contents of the electrolysis cell to a 500 ml. round-bottomed flask, render neutral with a little acetic acid, and distil off the methanol on a water... 

Reflux 14 6 g. of the ester with a solution of 10 g. of sodium hydroxide in 125 ml. of 80 per cent, methanol for 2 hours on a water bath. Add 200 ml. of water to dissolve the solid which separates, extract with two 30 ml. portions of ether, and warm the aqueous solution on a water bath to remove dissolved ether. Acidify the ice cold aqueous solution to litmus by the addition of concentrated hydrochloric acid. Collect the precipitated acid by suction filtration, wash it with a little cold water, and dry at 100°. The yield of sebacic acid, m.p. 133°, is 11 - 5 g... 

Myristic acid from hexanoic acid and methyl hydrogen sebacate). Dissolve 23 -2 g. of redistilled hexanoic acid (re caproic acid), b.p. 204-6-205-5°/760 mm., and 21-6 g. of methyl hydrogen sebacate in 200 ml. of absolute methanol to which 0 13 g. of sodium has been added. Electrolyse at 2 0 amps., whilst maintaining the temperature between 30° and 40°, until the pH is about 8 0 (ca. 6 hours). Neutralise the contents of the electrolysis cell with a little acetic acid and distil off the methyl alcohol on a water bath. Dissolve the residue in 200 ml. of ether, wash with three 50 ml. portions of saturated sodium bicarbonate solution, once with water, dry with anhydrous magnesium sulphate, and distil with the aid of a fractionating column (see under Methyl hydrogen adipate). Collect the re-decane at 60°/10 mm. (3 0 g.), the methyl myristate at 158-160°/ 10 mm. (12 5g.) and dimethyl hexadecane-1 16-dicarboxylate at 215-230°/ 7 mm. (1 -5 g.)... 

The by-product of this process, pelargonic acid [112-05-0] is also an item of commerce. The usual source of sebacic acid [111-20-6] for nylon-6,10 [9008-66-6] is also from a natural product, ticinoleic acid [141-22-0] (12-hydroxyoleic acid), isolated from castor oil [8001-79-4]. The acid reacts with excess sodium or potassium hydroxide at high temperatures (250—275°C) to produce sebacic acid and 2-octanol [123-96-6] (166) by cleavage at the 9,10-unsaturated position. The manufacture of dodecanedioic acid [693-23-2] for nylon-6,12 begins with the catalytic trimerization of butadiene to make cyclododecatriene [4904-61-4] followed by reduction to cyclododecane [294-62-2] (see Butadiene). The cyclododecane is oxidatively cleaved to dodecanedioic acid in a process similar to that used in adipic acid production. 

Alkali Fusion. Tha alkaU fusion of castor oil using sodium or potassium hydroxide in the presence of catalysts to spHt the ricinoleate molecule, results in two different products depending on reaction conditions (37,38). At lower (180—200°C) reaction temperatures using one mole of alkah, methylhexyl ketone and 10-hydroxydecanoic acid are prepared. The 10-hydroxydecanoic acid is formed in good yield when either castor oil or methyl ricinoleate [141-24-2] is fused in the presence of a high boiling unhindered primary or secondary alcohol such as 1- or 2-octanol. An increase to two moles of alkali/mole ricinoleate and a temperature of 250—275°C produces capryl alcohol [123-96-6] CgH gO, and sebacic acid [111-20-6] C QH gO, (39—41). Sebacic acid is used in the manufacture of nylon-6,10. 

Decamethylene glycol has been prepared by the reduction of dimethyl sebacate and diethyl sebacate with sodium and ethyl alcohol by the reduction of sebacamide with sodium and amyl alcohol and by the reduction of dimethyl sebacate with sodium and liquid ammonia in absolute alcohol. The reduction of esters with sodium and alcohol has also been applied to the preparation of many other glycols. ... 

Should be distd under reduced pressure under nitrogen and stored in the dark. Purified via the nitrosochloride [Waterman et al. Reel Trav Chim Pays-Bas 48 1191 7929]. For purification of optically active forms see Lynn [J Am Chem Sac 91 361 1919]. Small quantities (0.5mL) have been purified by GLC using helium as carrier gas and a column at 90 packed with 20 wt% of polypropylene sebacate on a Chromosorb support. Larger quantities were fractionally distd under reduced pressure in a column packed with stainless steel gauze spirals. Material could be dried with CaH2 or sodium, and stored in a refrigerator CaS04 and silica gel were not satisfactory because they induced spontaneous isomerisation. [Bates, Best and Williams 7 C/iem Soc 1521 7962.]... 

Ethyl pentadecylate, 16, 37 Ethyl pentanehexacarboxylate, 10, 59 Ethyl phenylacetate, 16, 33 Ethyl -phenylacetoacetate, 18, 36 Ethyl -y-phenylbctyrate, 18, 25, 26 Ethyl phenylcyanopyruvate, 11, 40 Ethyl /J-phenylethyl ketone, 16, 49 Ethyl phenylmalonate, 16, 33 18, 84 Ethyl phenyloxaloacetate, 16, 33 Ethyl phthalimidomalonate, 14, 58 Ethyl pjmelate, 11, 42 17, 91 Ethyl propanetetracarboxylate, 10, 58 Ethyl propionate, 17, 34 Ethyl tso-propylmalonate, 11, 20, 21 Ethyl salicylate, 10, 51 11, 43 Ethyl sebacate, 14, 20 Ethyl sodium phthalimidomalonate, 14, 58... 

Sebacic add, 43, 39 Sebacoyl chloride, 43, 37 2,2 -Sebacoyldicyclohexanone, 43, 34 Sodium amide, as catalyst for carbona-tion of methylacetylene, 42, 98... 

Portland cement Sodium sulfate waste from sebacic acid production [1428]... 

V. G. Mosienko, Y. I. Petrakov, V. F. Nagomova, and V. N. Nikiforova. Complex additive for plugging solutions—contains modifying reagent in form of waste from production of sebacic acid, from stage of neutralising of sodium salts of fatty acids. Patent RU 2074310-C, 1997. 

A. A. Perejma, K. M. Tagirov, V. I. Ilyaev, and A. A. Kovalev. Plugging solution for conducting well repair works, etc.—contains Portland cement, polyacrylamide, specified stabilising additive, sodium sulphate waste from sebacic acid production and water. Patent RU 2035585-C, 1995. 

Dioctyl sebacate (DOS) with relative permittivity e of 3.9 and 2-nitrophenyl octyl ether (NPOE) with e = 23.9 are the traditionally used sensor membrane plasticizers. The choice of a plasticizer always depends on a sensor application. Thus, NPOE appears to be more beneficial for divalent ions due to its higher polarity, but for some cases its lipophilicity is insufficient. Furthermore, measurements with NPOE-plasticized sensors in undiluted blood are complicated by precipitation of charged species (mainly proteins) on the sensor surface, which leads to significant potential drifts. Although calcium selectivity against sodium and potassium for NPOE-based membranes is better by two orders of magnitude compared to DOS membranes, the latter are recommended for blood measurements as their lower polarity prevents protein deposition [92],... 

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