Adipic acid compositions

• US 8,669,393 B2
• Filed: 12/13/2010
• Issued: 03/11/2014
• Est. Priority Date: 03/05/2010
• Status: Active Grant

• Current Assignee: Archer Daniels Midland Company
• Original Assignee: Rennovia Inc.
• Inventors: Boussie, Thomas R., Dias, Eric L., Fresco, Zachary M., Murphy, Vincent J., Shoemaker, James, Archer, Raymond, Jiang, Hong
• Primary Examiner(s): Shen, Wu-Cheng Winston
• Assistant Examiner(s): Doletski, Blaine G
• Application Number:
  US12/966,783
• Publication Number:
  US 20110218318A1
• Time in Patent Office: 1,184 Days
• Field of Search: 528/302, 540/485, 435/135, 558/311, 568/864, 549/292, 562/590
• US Class Current: 560/1
• CPC Class Codes: C07C 255/04 containing two cyano groups bound to the carbon skeleton
• CPC Class Codes: C07D 223/10 attached in position 2
• CPC Class Codes: C08G 63/00 Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule polyester-amides C08G69/44; polyester-imides C08G73/16
• CPC Class Codes: C08G 69/14 Lactams
• CPC Class Codes: C08G 69/26 derived from polyamines and polycarboxylic acids

Abstract

Disclosed are compositions of matter comprising an adipic acid product of formula (1)

wherein R is independently a salt-forming ion, hydrogen, hydrocarbyl, or substituted hydrocarbyl, and

• • at least one constituent selected from the group consisting of formula (2)

wherein R is as defined above and each of R1 is, independently, H, OH, acyloxy or substituted acyloxy provided, however, that at least one of R1 is OH, and formula (3)

wherein R is as above defined and R1 is OH, acyloxy or substituted acyloxy. Also disclosed are compositions of matter comprising at least about 99 wt % adipic acid and least two constituents selected from the group consisting of formula (2) and formula (3), above.

Claims

1. A composition comprising an adipic acid product of formula (1)

2. The composition of claim 1 comprising at least about 99 wt % adipic acid or a salt thereof and up to about 1 wt % of at least one compound of formula (2).

4. The composition of claim 1 comprising at least about 99 wt % adipic acid and tip to about 1 wt % of at least two compounds each selected from the group consisting of formula (2) and formula (3).

5. The composition of claim 1 wherein each R of formulas (1), (2), and (3) is independently a salt-forming ion, hydrogen, hydrocarbyl containing 1 to 18 carbon atoms, or substituted hydrocarbyl containing 1 to 18 carbon atoms.

6. The composition of claim 5 wherein the hydrocarbyl containing 1 to 18 carbon atoms is selected from the group consisting of alkyl, alkylene, alkoxy, alkylamino, thioalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, N-heterocyclyl, heterocyclylalkyl, aryl, aralkyl heteroaryl, N-heteroaryl, and heteroarylalkyl.

7. The composition of claim 5 wherein the substituted hydrocarbyl containing 1 to 18 carbon atoms is selected from the group consisting of substituted alkyl and substituted cycloalkyl.

8. The composition of claim 1 wherein the salt-forming ion is selected from the group consisting of ammonium ions, alkali metal ions, and alkaline earth metal ions.

9. The composition of claim 1 wherein each R of formulas (1), (2), and (3) is independently hydrogen or a salt-forming ion selected from the group consisting of ammonium ions, alkali metal ions, and alkaline earth metal ions.

10. The composition of claim 1 wherein each R of formulas (1), (2), and (3) is independently hydrogen.

11. The composition of claim 1 wherein each R₁ of formulas (1), (2), and (3) is independently hydrogen or OH.

3. A composition comprising at least about 99 wt % adipic acid and up to about 1 wt % of at least one compound selected from the group consisting of formula (2)

12. The composition of claim 3 wherein each R of formulas (2) and (3) is independently a salt-forming ion, hydrogen, hyrocarbyl containing 1 to 18 carbon atoms, or substituted hydrocarbyl containing 1 to 18 carbon atoms.

13. The composition of claim 12 wherein the hydrocarbyl containing 1 to 18 carbon atoms is selected from the group consisting of alkyl, alkylene, alkoxy, alkylamino, thioalkyl, haloalkyl, cycloalkyl, cycloalkylalkyl, heterocyclyl, N-heterocyclyl, heterocyclylalkyl, aryl, aralkyl heteroaryl, N-heteroaryl, and heteroarylalkyl.

14. The composition claim 12 wherein the substituted hydrocarbyl containing 1 to 18 carbon atoms is selected from the group consisting of substituted alkyl and substituted cycloalkyl.

15. The composition of claim 3 wherein the salt-forming son is selected from the group consisting of ammonium ions, alkali metal ions, and alkaline earth metal ions.

16. The composition of claim 3 wherein each R of formulas (2) and (3) is independently hydrogen or a salt-forming ion selected from the group consisting of ammonium ions, alkali metal ions, and alkaline earth metal ions.

17. The composition of claim 3 wherein each R of formula (2) and (3) is independently hydrogen.

18. The composition of claim 3 wherein each R₁ of formulas (2) and (3) is independently hydrogen or OH.