Processes for making azelaic acid and derivatives thereof
View Patent ↗Methods of making azelaic acid, or derivatives thereof, from unsaturated monobasic acids or esters are disclosed herein. In some embodiments, the unsaturated monobasic acids or esters are C 10-17 unsaturated monobasic acids or esters.
1. A method for forming azelaic acid or a derivative thereof, the method comprising:
providing a reactant composition comprising a compound of formula (I):
and
reacting the compound of formula (I) with an oxidizing agent to form a product composition comprising a compound of formula (II):
wherein:
R 1 is a hydrogen atom, C 1-12 alkyl, C 1-12 heteroalkyl, or a cationic counterion;
R 2 is a hydrogen atom, methyl, or ethyl; and
R 3 is a hydrogen atom, C 1-12 alkyl, C 1-12 heteroalkyl, or a cationic counterion.
2. The method of claim 1 , wherein R 1 is a hydrogen atom.
3. The method of claim 1 , wherein R 1 is C 1-12 alkyl.
4. The method of claim 3 , wherein R 1 is methyl, ethyl, or isopropyl.
5. The method of claim 1 , wherein R 1 is C 1-12 heteroalkyl.
6. The method of claim 1 , wherein R 1 is a cationic counterion.
7. The method of claim 1 , wherein R 2 is a hydrogen atom.
8. The method of claim 1 , wherein R 2 is methyl or ethyl.
9. The method of claim 1 , wherein R 3 is a hydrogen atom.
10. The method of claim 1 , wherein R 3 is C 1-12 alkyl.
11. The method of claim 10 , wherein R 3 is methyl, ethyl, or isopropyl.
12. The method of claim 1 , wherein R 3 is C 1-12 heteroalkyl.
13. The method claim 1 , wherein R 3 is a cationic counterion.
14. The method of claim 1 , wherein the oxidizing agent comprises hydrogen peroxide.
15. The method of claim 1 , wherein the oxidizing agent comprises ozone.
16. The method of claim 1 , further comprising converting the compound of formula (II) to azelaic acid.
17. The method of claim 16 , wherein the converting comprises hydrolyzing the compound of formula (II).
18. The method of claim 16 , wherein the converting comprises saponifying the compound of formula (II), followed by acidification of the product of the saponification.