Processes for making azelaic acid and derivatives thereof
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.