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ChemicalBook CAS DataBase List Sebacic acid

Sebacic acid synthesis

9synthesis methods
Sebacic acid is normally made from castor oil, which is essentially glycerol triricinoleate. The castor oil is heated with sodium hydroxide at about 250°e. This treatment results in saponification of the castor oil to ricinoleic acid which is then cleaved to give 2-octanol and sebacic acid:


This process results in low yields of sebacic acid (about 50% based on the castor oil) but, nevertheless, other routes have not proved competitive. Sebacic acid is a colourless crystalline solid, m.p. 134℃.
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Yield:111-20-6 98%

Reaction Conditions:

with palladium 10% on activated carbon;W(OTf)6;hydrogen;acetic acid at 20 - 180; under 22801.5 Torr; for 10.5 h;Reagent/catalyst;Pressure;Temperature;

Steps:

8 Example 8

4,7-dione-1,10-sebacic acid,The palladium content is 10% by weight of palladium on carbon,W(OTf)6,Mix with acetic acid,After replacing the gas with hydrogen four times,Charge hydrogen gas at room temperature to hydrogen pressure of 30atm.At 500r/min speed,Stirred and heated to 180°C within 30min,Keep stirring for 10hCooling,Relieve pressure,Filter the filtrate,Distillation under reduced pressure to obtain a solid;The solid was dissolved in a 10 wt% aqueous sodium hydroxide solution.Add activated carbon heating decolorization 30min,Filter the filtrate,Adjust pH to less than 2 with hydrochloric acidFilter cakesDrying gives 1,10-sebacic acid,among them,4,7-Dione-1,10-sebacic acid,The molar ratio of W(OTf)6 is 50:3.The molar ratio of palladium to 4,7-dione-1,10-sebacic acid in palladium carbon is 1:50.The molar volume (mol/l) ratio of 4,7-dione-1,10-decanedioic acid and acetic acid is 1:10.

References:

CN107382712,2017,A Location in patent:Paragraph 0077; 0082; 0087; 0092; 0097; 0102; 0107

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