Liquid phase oxidation of aromatic feedstocks with manganate recycling to produce carboxylic acids
US-2016289156-A1 · Oct 6, 2016 · US
US10017447B2 · US · B2
| Field | Value |
|---|---|
| Publication number | US-10017447-B2 |
| Application number | US-201514939661-A |
| Country | US |
| Kind code | B2 |
| Filing date | Nov 12, 2015 |
| Priority date | Nov 26, 2014 |
| Publication date | Jul 10, 2018 |
| Grant date | Jul 10, 2018 |
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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.
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What is claimed is: 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.
with peroxy-compounds · CPC title
Azelaic acid · CPC title
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