Sebacamate

METHYL SEBACAMATE (Sebacamic acid, methyl ester) 

Methyl sebacamate. Two and one-half liters of concentrated aqueous ammonia (about 28%) in a 4-1. beaker or enameled pot (Note 2) is stirred vigorously with an off-center stirrer and chilled to 8° in a cooling bath. The crude chloride from part A is added slowly from a dropping funnel to the solution which is kept below 8° throughout the addition. A vigorous reaction takes place, and methyl sebacamate precipitates immediately. After the addition has been completed, the product is filtered by suction and washed with 200 ml. of cold water. After 3 days drying in a vacuum desiccator, the methyl sebacamate weighs 200-204 g. (93-95%) and melts at 72-74° (Note 3). 

Methyl hydrogen sebacate (b.p. 168-170°/3 mm.) was prepared by the checkers in yields of 52-61% from sebacic acid and methanol by the procedure described for the ethyl analog.1 The ethyl ester can be used to obtain ethyl sebacamate. The preparation of the acid chloride from ethyl hydrogen sebacate is mentioned in Note 12, page 21. 

A variety of enameled-steel pots known as bain-marie is available from the American Specialty Company, Rochester, New York. 

These compounds are described only in the recent literature.2 8 

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In a 1.5-1. Erlenmeyer flask to which is attached a reflux condenser, 190 g. (0.88 mole) of methyl sebacamate (p. 71) is dissolved in 200 ml. of boiling tetrachloroethane. The solution is allowed to cool to 40-50° (Note 1), 95 g. (0.67 mole) of phosphorus pentoxide is added (Note 2), and the mixture is stirred well by means of a glass rod. The mixture is heated in an oil bath to 120° (thermometer in oil), and a second 95-g. portion of phosphorus pentoxide is added. After the mixture has been heated at 145° for 30 minutes with occasional hand stirring, the liquid is decanted. The residue is heated at 145° with 200 ml. of tetrachloroethane for 30 minutes with occasional stirring, and the liquid is decanted. This process is repeated once. The combined extracts are placed in a 1-1. flask, and most of the solvent is distilled under the reduced pressure of a water pump. The residue is transferred to a 300-ml. flask, and the remainder of the solvent is removed (Note 3). When no more distillate comes over, the receiver is changed, the water pump is replaced by an oil pump, and the residue is fractionated (Note 4). The yield... 

Sebacamic acid, methyl ESTER, 25, 71 Sebacamide, 25, 95 Sebacic acid, 25, 95 Sebaconitrile, 25, 95 27, 18 Selenious acid, 24, 61, 62 Selenium, 24, 63 27, 33 powdered, black, 24, 90 Selenium compounds, ease of oxidation, 24,91... 

The reaction of ammonia with the acyl chloride grouping is much more rapid than with a methyl ester, as is shown in the preparation of methyl sebacamate, NHjC0(CH,) C02CH, in 95% yield from 00 -carbomethoxy-pelargonyl chloride. ... 

Methylresorcinol, 514 Methyl sebacamate, 871 Methyl stearate, 865 a-Methylstytene, 172, 255... 

The reactants are mixed by shaking, the mixture heated, and the product distilled at atmospheric pressure or at 20 mm. Dehydration of methyl sebacamate is done in tetrachloroethane, and dehydration of chloroacetamide is carried out at the boiling... 

Methylpyrrolidine, 25, 19 Methyl pyruvate, 24, 72 Methyl sebacamate, 25, 71 Methylsuccinic acid, 26, 54... 

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