ChemicalBook CAS DataBase List DIETHYL AZELATE

DIETHYL AZELATE synthesis

7synthesis methods

Product Name:DIETHYL AZELATE
CAS Number:624-17-9
Molecular formula:C13H24O4
Molecular Weight:244.33

123-99-9 Synthesis

123-99-9
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$14.00/5g

64-17-5 Synthesis

64-17-5
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$10.00/50g

624-17-9
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$40.00/5g

Yield:624-17-9 88%

Reaction Conditions:

with hydrogenchlorideHeating / reflux;

Steps:

1

A mixture of azelaic acid (20 g) and 200 proof USP anhydrous ethanol (200 ml) was placed into a 350 ml gas washing bottle. Into this solution anhydrous EPO hydrogen chloride gas was instilled through the gas inlet of the bottle. The addition of gas was carried out in a chemical fume hood with stirring at room temperature. The gas was bubbled into the solution at a rate such that few if any of the bubbles reached the surface of the solution, as hydrogen chloride is very soluble in alcohols and thus the gas dissolves before escaping the solution. The addition of gas was continued for 2 hours at which point the gas tank was turned off and disconnected. Stirring was continued overnight. The following day the solution was heated to reflux in an open 1 L Erlenmeyer flask and allowed to reflux for 2 hours. This heating had the effect of driving off a large portion of the dissolved hydrogen chloride. The solution was then cooled to room temperature and concentrated under vacuum to produce a clear, slightly yellow oil. This oil was the predominantly the diethyl ester of azelaic acid. The crude diester was dissolved in ethyl acetate and washed several times with a saturated water solution of sodium bicarbonate. The diester was then washed several more times with water until the pH of the wash water was neutral. The semi-purified diester was then vacuum distilled to produce 22 grams of the diester (88% of theoretical).

References:

WO2006/74379,2006,A2 Location in patent:Page/Page column 18-19