Sebacic acid sebacate

Sebacic acid Sebacic acid [110-20-6] Sebacic acid [111-20-6]... 

Now it is possible to produce cis-decalin or trans-decalin, with over 80% selectivity at 100% conversion by using some zeolite-supported catalysts at 200°C. cis-Decalin may have potential industrial application as the starting material for making sebacic acid. Sebacic acid can be used for manufacturing Nylon 6,10 and softeners [Weissermel and Arpe, 1993],... 

Nylon 6,10 is the polyamide from hexamethylene diamine and sebacic acid. Sebacic acid occurs by alkali splitting of ricinoleic acid ... 

HOOC-[CHa]8-COOH, CioH.aO. Colourless leaflets m.p. 134°C. Manufactured by heating castor oil with alkalis or by distillation of oleic acid. Forms an anhydride, m.p. 78 C. The esters of sebacic acid are used as plasticizers, especially for vinyl resins. 

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. 

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... 

Decane-1 10-dicarboxylic acid from sebacic acid. Convert sebacic acid into the acid chloride by treatment with phosphorus penta-chloride (2 mols) and purify by distillation b.p. 146-143°/2 mm. the yield is almost quantitative. Dissolve the resulting sebacoyl chloride in anhydrous ether and add the solution slowly to an ethereal solution of excess of diazomethane (prepared from 50 g. of nitrosomethylurea) allow the mixture to stand overnight. Remove the ether and excess of diazomethane under reduced pressure the residual crystalline 1 8-bis-diazoacetyloctane weighs 19 -3 g. and melts at 91° after crystaUisation from benzene. 

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) ... 

An excellent synthesis of myristic acid is thus achieved from readily accessible starting materials. An alternative synthesis of myristic acid utilises hexanoic acid (M-caproic acid n-hexoic acid) (X) (2 mols) and methyl hydrogen sebacate (XI) (1 mol) the products, after hydrolysis, are Ji-decane (XII), myristic acid (XIII) and hexadecane-1 16-dlcarboxylic acid (XIV) ... 

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.)... 

Polyamides from diamines and dibasic acids. The polyamides formed from abphatic diamines (ethylene- to decamethylene-diamine) and abphatic dibasic acids (oxabc to sebacic acid) possess the unusual property of forming strong fibres. By suitable treatment, the fibres may be obtained quite elastic and tough, and retain a high wet strength. These prpperties render them important from the commercial point of view polyamides of this type are cabed nylons The Nylon of commerce (a 66 Nylon, named after number of carbon atoms in the two components) is prepared by heating adipic acid and hexamethylenediamine in an autoclave ... 

Aqueous caprolactam is polymerized alone and in the presence of sebacic acid (S) or hexamethylenediamine (H).t After a 24-hr reaction time, the polymer is isolated and the end groups are analyzed by titrating the carboxyl groups with KOH in benzyl alcohol and the amino groups with p-toluenesulfonic acid in trifluoroethanol. The number of milliequivalents of carboxyl group per mole caprolactam converted to polymer, [A ], and the number of milliequivalents of amino groups per mole caprolactam converted to polymer, [B ], are given below for three different runs ... 

Batzer has reported the following data for a fractionated polyester made from sebacic acid and 1,6-hexanediol ... 

Reimschuessel and Deget polymerized caprolactam in sealed tubes containing about 0.0205 mol HjO per mole caprolactam. In addition, acetic acid (V), sebacic acid (S), hexamethylene diamine (H), and trimesic acid (T) were introduced as additives into separate runs. The following table lists (all data per mole caprolactam) the amounts of additive present and the analysis for end groups in various runs ... 

Dibasic Acid Esters. Dibasic acid esters (diesters) are prepared by the reaction of a dibasic acid with an alcohol that contains one reactive hydroxyl group (see Esters, organic). The backbone of the stmcture is formed by the acid. The alcohol radicals are joined to the ends of the acid. The physical properties of the final product can be varied by using different alcohols or acids. Compounds that are typically used are adipic, azelaic, and sebacic acids and 2-ethyIhexyl, 3,5,5-trimethyIhexyl, isodecyl, and tridecyl alcohols. 

Low Temperature Performance. The abihty of plasticized PVC to remain flexible at low temperatures is of great importance in certain apphcations, eg, external tarpaulins or underground cables. Eor this property the choice of the acid constituent of the plasticizer ester is also important. The linear aUphatic adipic, sebacic, and azeleic acids give excellent low temperature flexibiUty compared to the corresponding phthalates and trimeUitates (Pig. 3). 

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. 

Nylon-6,9, Nylon-6,10, and Nylon-6,12. These nylons are all produced from hexamethylenediamine and either azelaic, sebacic, or dodecanoic acid. They are produced by a process similar to that for nylon-6,6, usually using batch autoclaves. 

Mliphatic dibasic acids such as succinic acid, adipic acid, azelaic acid, and sebacic acids have also been used to make alkyd resins. Their linear chain stmcture lends higher flexibiUty and lower viscosity to the resin as compared to the rigid aromatic rings of phthaUc acids. 

Polyols. Analogous to the use of linear a,C0-dibasic acids, such as adipic and sebacic, polyols with long, flexible chains between hydroxyl groups, such as 1,4-butanediol [110-63-4] 1,6-hexanediol [629-11-8J, and diethylene glycol [111-46-6] may also be used to impart greater flexibiUty ia the resia. 

An example is poly(bis(p-carboxyphenoxy)propane) (PCPP) which has been prepared as a copolymer with various levels of sebacic anhydride (SA). Injection molded samples of poly (anhydride) / dmg mixtures display 2ero-order kinetics in both polymer erosion and dmg release. Degradation of these polymers simply releases the dicarboxyhc acid monomers (54). Preliminary toxicological evaluations showed that the polymers and degradation products had acceptable biocompatibiUty and did not exhibit cytotoxicity or mutagenicity (55). 

In plasticizer manufacture, eg, of phthalates or sebacates, uskig sulfuric or/ -toluenesulfonic acid catalysts, the temperature (140—150°C) requked for rapid reaction and high conversion may dehydrate or oxidize the alcohol and may yield a dark or foul-smelling product. Neutral titanates do not cause such side reactions. Although a temperature of 200°C is requked, esterifications can easily be forced to over 99% conversion without the formation of odors or... 

Alkali fusion of oleic acid at about 350°C ia the Varrentrapp reaction causes double-bond isomerization to a conjugated system with the carboxylate group followed by oxidative cleavage to form palmitic acid (75). In contrast, alkaU fusion of riciaoleic acid is the commercial route to sebacic acid [111 -20-6] ... 

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