ChemicalBook CAS DataBase List Sebacic acid

Sebacic acid synthesis

9synthesis methods

Product Name:Sebacic acid
CAS Number:111-20-6
Molecular formula:C10H18O4
Molecular Weight:202.25

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

112-38-9 Synthesis