Carboxylic acid production process employing solvent from esterification of lignocellulosic material

• US 8,614,350 B2
• Filed: 08/24/2012
• Issued: 12/24/2013
• Est. Priority Date: 01/15/2008
• Status: Expired due to Fees

• Current Assignee: Eastman Chemical Company
• Original Assignee: Eastman Chemical Company
• Inventors: Janka, Mesfin Ejerssa, Sumner, Charles Edwan Jr., Howard, Adam Scott, Parker, Kenny Randolph
• Primary Examiner(s): Katakam, Sudhakar
• Application Number:
  US13/593,553
• Publication Number:
  US 20120323039A1
• Time in Patent Office: 487 Days
• Field of Search: None
• US Class Current: 562/412
• CPC Class Codes: C07B 41/08 of carboxyl groups or salts, halides or anhydrides thereof
• CPC Class Codes: C07C 51/087 by hydrolysis
• CPC Class Codes: C07C 51/265 having alkyl side chains which are oxidised to carboxyl groups
• CPC Class Codes: C07C 53/08 Acetic acid pyroligneous acid C10C; preparation of vinegar C12J
• CPC Class Codes: C07C 63/26 1,4 - Benzenedicarboxylic acid
• CPC Class Codes: D21C 11/0007 Recovery of by-products, i.e. compounds other than those necessary for pulping, for multiple uses or not otherwise provided for volatile compounds obtained by decomposition of spent liquors in order to regenerate them D21C11/125; compounds obtained by fractionating the liquors in order to regenerate them D21C11/0042
• CPC Class Codes: D21H 11/20 Chemically or biochemically modified fibres

Abstract

Methods and apparatus for producing a carboxylic acid employing a solvent from esterification of lignocellulosic materials. An acid-containing composition from esterification of lignocellulosic materials can be employed in the oxidation of para-xylene to terephthalic acid. The acid-containing composition can comprise acetic acid, acetic anhydride, and one or more terpenes or terpenes derivatives.

Claims

1. A process for producing an aromatic carboxylic acid, said process comprising oxidizing an oxidation feed comprising at least one oxidizable compound and at least one solvent comprising a monocarboxylic acid, wherein at least a portion of said monocarboxylic acid originated from a wood acetylation process;

and wherein said solvent further comprises one or more terpenes or terpene derivatives;

wherein at least 50% of the said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

2. The process of claim 1, wherein said solvent further comprises acetic anhydride in an amount of at least 0.01 weight percent based on the weight of monocarboxylic acid employed from said wood acetylation process.

3. The process of claim 2, wherein said oxidizing produces water as a byproduct, wherein at least a portion of said acetic anhydride consumes at least a portion of said water.

4. The process of claim 1, wherein said monocarboxylic acid comprises acetic acid, wherein at least 5 weight percent of said acetic acid is acetic acid originated from said wood acetylation process.

5. The process of claim 4, wherein said solvent comprises a combined concentration of all of said terpenes in an amount of at least 0.01 weight percent based on the weight of acetic acid employed from said wood acetylation process.

6. The process of claim 1, said process further comprising at least one purification step.

7. The process of claim 1, wherein said oxidizable compound comprises para-xylene, wherein said carboxylic acid comprises terephthalic acid.

8. A process for producing an aromatic carboxylic acid, said process comprising:

(a) contacting at least one lignocellulosic material with a compound containing at least one acetyl group to thereby produce an acetylated lignocellulosic material and an acid-containing composition; and

(b) introducing at least a portion of said acid-containing composition and an oxidizable compound into a carboxylic acid production process, wherein said acid-containing composition comprises acetic acid; and

wherein said acid-containing composition comprises one or more terpenes or terpene derivatives in an amount of at least 0.01 weight percent based on the weight of said acetic acid in said acid-containing composition;

wherein at least 50% of the said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

9. The process of claim 8, wherein said acid-containing composition further comprises acetic anhydride in an amount of at least 0.01 weight percent based on the weight of said acetic acid in said acid-containing composition.

10. The process of claim 8, wherein said carboxylic acid production process comprises an oxidation reactor, wherein said process further comprises oxidizing at least a portion of said oxidizable compound in the presence of at least a portion of said acid-containing composition in said oxidation reactor, wherein said oxidizing produces water as a byproduct, wherein at least a portion of said acetic anhydride consumes at least a portion of said water.

11. The process of claim 8, wherein said lignocellulosic material comprises wood, wherein said compound containing at least one acetyl group comprises acetic anhydride in an amount of at least 0.05 weight percent.

12. The process of claim 8, wherein said oxidizable compound comprises para-xylene, wherein said carboxylic acid comprises terephthalic acid.

13. The process of claim 10, wherein said carboxylic acid production process further comprises at least one purification step.

14. A process for producing an aromatic carboxylic acid, said process comprising oxidizing an oxidizable compound in an oxidation reactor in the presence of at least one solvent, wherein said solvent comprises acetic anhydride in an amount of at least 0.01 weight percent based on the total weight of the solvent;

wherein said solvent comprises acetic anhydride in an amount of at least 0.05 weight percent based on the total weight of the solvent.

15. The process of claim 14, wherein said solvent comprises terpenes in a cumulative amount of at least 0.01 weight percent based on the total weight of the solvent.

16. The process of claim 15, wherein at least a portion of said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

17. The process of claim 15, wherein at least 70% of the said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

18. The process of claim 15, wherein at least 90% of the said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

19. The process of claim 15, wherein at least 99% of the said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

20. The process of claim 15, wherein at least 99.9% of the said terpenes or terpenes derivatives are oxidized in said oxidation reactor to form carbon monoxide and carbon dioxide.

21. The process of claim 15, wherein at least a portion of said terpenes or terpenes derivatives are oxidized in said oxidation reactor but do not affect conversion, yield and product quality.

22. The process of claim 14, wherein said oxidizing produces water as a byproduct, wherein at least a portion of said acetic anhydride consumes at least a portion of said water.

23. The process of claim 14, wherein at least a portion of said solvent originates from a wood acetylation process.

24. The process of claim 14, wherein said solvent further comprises acetic acid and/or water, wherein said carboxylic acid comprises terephthalic acid, wherein said oxidizable compound comprises para-xylene.

25. The process of claim 14, said process further comprising at least one purification step.