Diethyl sebacate

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. 

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. ... 

Hishida was unable to obtain any identifiable products when he attempted to extend this work to include the, monoesters of several aliphatic dibasic acids. However, definite products (269 and 270) were obtained using diethyl adipate and diethyl sebacate, respectively. A second product containing only one indole residue (271) was also obtained in the latter case. ... 

Room-temperature ionic liquids have received much attention as green designer solvents. We first demonstrated that ionic liquids acted as good medium for lipase-catalyzed production of polyesters. The polycondensation of diethyl adipate and 1,4-butanediol using lipase CA as catalyst efficiently proceeded in l-butyl-3-methylimidazolinium tetrafluoroborate or hexafluorophosphate under reduced pressure. The polymerization of diethyl sebacate and 1,4-butanediol in l-butyl-3-methylimidazolinium hexafluorophosphate took place even at room temperature in the presence of lipase BC. ... 

Unactivated esters, typically alkyl esters, often show low reactivity toward lipase catalyst for transesterifications. In the case of the lipase-catalyzed polycondensation of dialkyl esters with glycols, the polymer of high molecular weight was not obtained. The molecular weight improved when vacuum conditions were used Mw reached more than 2 x 104 in the combination of diethyl sebacate and 1,4-butanediol catalyzed by lipase MM [30]. 

Ethyl 10-undecenoate ozonide was autoxidized at 95% in the absence of a catalyst. Diethyl sebacate, methyl ethyl sebacate, and dimethyl sebacate were detected after diazomethane treatment. When the ozonide was oxidized in acetone over platinum black and similarly treated with diazomethane, dimethyl sebacate could not be detected. 

DES = Diethyl sebacate DBS = Dibutyl sebacate DHS = Dihexyl sebacate DOS = Dioctyl sebacate DNS = Dinonyl sebacate... 

Diethyl sebacate. Reflux a mixture of 101 g (0.5 mol) of sebacic acid, 196 g (248 ml, 4.25 mol) of absolute ethanol and 20 ml of concentrated sulphuric acid for 12 hours. Distil off 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 hydrogen carbonate solution until effervescence ceases, and finally with water. Dry with magnesium sulphate or anhydrous sodium sulphate, remove the ether on a water bath and distil the residue under reduced pressure (b.p. 155-157 °C/6 mmHg). Yield llOg (85%). 

Benzyl Benzoate 659 Cedar Leaf Oil 675 Diethyl Sebacate... 

Soga F, Katoh N, Kishimoto S. Contact dermatitis due to lanoconazole, cetyl alcohol and diethyl sebacate in lano-conazole cream. Contact Dermatitis 2004 50(l) 49-50. 

Diethyl sebacate is an emulsifier used in cosmetics and topical medicaments. In contrast to the emulsifying agents stearyl alcohol, stearic acid, and glyceryl stearate, diethyl sebacate is considered to be a rare sensitizer. 

There were positive patch tests to diethyl sebacate (10 and 30% in ether and 1 and 10% in petrolatum) in a 48-year-old woman who had been using a topical antimycotic ointment (1). 

Kimura M, Kawada A. Contact dermatitis due to diethyl sebacate. Contact Dermatitis 1999 40(l) 48-9. 

Tanaka M, Kobayashi S, Murata T, Tanikawa A, Nishikawa T. Allergic contact dermatitis from diethyl sebacate in lanoconazole cream. Contact Dermatitis 2000 43(4) 233. ... 

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