IP Library Granted Patent US 11,951,649
Granted Patent B2
US 11,951,649 · App. 17/854,196 · Granted Apr 9, 2024

Method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom

Inventors: Md Sayful Islam (Peachtree City, GA); Jun Zhang (Peachtree City, GA)
Assignee: Koppers Performance Chemicals, Inc.
B27K3/22C07C51/412
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Quick Facts
Patent No.
US 11,951,649
App. No.
17/854,196
Granted
Apr 9, 2024
Kind
B2
Abstract

A method for producing copper carboxylate, a wood preservative composition comprising copper carboxylate, and a wood product produced therefrom are provided. The method comprises combining a hydrocarbon solvent, a copper compound, and carboxylic acid and contacting the copper compound with the carboxylic acid in the presence of the hydrocarbon solvent to form a reaction product comprising copper carboxylate.

Claims (40)

1. A method for producing copper carboxylate, the method comprising:

combining a hydrocarbon solvent and a copper compound to form an intermediate mixture, wherein the hydrocarbon solvent comprises a flash point in a range of 58 degrees Celsius to 140 degrees Celsius;

heating a carboxylic acid having at least 8 carbon atoms to a temperature of at least 30 degrees Celsius to form a heated carboxylic acid; and

combining the intermediate mixture and the heated carboxylic acid to form a reaction product comprising

copper carboxylate, wherein an elemental copper concentration is in a range of 2 percent to 12 percent based on a total weight of the reaction product; and

at least 20 percent by weight hydrocarbon solvent based on the total weight of the reaction product.

2. The method of claim 1 , wherein the carboxylic acid comprises at least one of

a formula of R—COOH or R—CO 2 H, where R is an alkyl group, an alkenyl group, or an aryl group; or

a formula of C n H 2n-z O 2 , where Z is 0, 2, 4, 6, or 8 and n is in a range of 8 to 20.

3. The method of claim 1 , wherein the carboxylic acid is derived from petroleum.

4. The method of claim 1 , wherein the carboxylic acid comprises an acid value in a range of 100 mg*KOH/g to 455 mg*KOH/g, a molecular weight in a range of 120 grams per mole to 700 grams per mole, a water content of less than 0.5 percent by total weight of the carboxylic acid, and a viscosity at 70 degrees Celsius in a range of 50 cP to 1500 cP.

5. The method of claim 1 , wherein the carboxylic acid is naphthenic acid.

6. The method of claim 1 , wherein the intermediate mixture is at a temperature in a range of 55 degrees Celsius to 90 degrees Celsius prior to combining with the heated carboxylic acid.

7. The method of claim 1 , wherein the combining the intermediate mixture and the heated carboxylic acid forms a mixture with a viscosity of no greater than 2,500 cP at 25 degrees Celsius.

8. The method of claim 1 further comprising introducing a defoamer, a demulsifying agent, a biocide, or a combination thereof.

9. The method of claim 1 , wherein the hydrocarbon solvent comprises diesel, fuel oil, pole-treating oil, a creosote-petroleum mixture, or a combination thereof.

10. The method of claim 1 , wherein an elemental copper percentage in the copper compound is in a range of 55 percent to 65 percent by total weight of the copper compound.

11. The method of claim 1 , wherein the copper compound comprises copper metal, copper (I) oxide, copper (II) oxide, copper hydroxide, copper carbonate, basic copper carbonate, copper oxychloride, or a combination thereof.

12. The method of claim 1 , wherein a mean average particle size of the copper compound is in a range of 0.05 um to 500 um.

13. The method of claim 1 , wherein a yield of the copper carboxylate is at least 90 percent.

14. The method of claim 1 , wherein the copper carboxylate comprises copper naphthenate.

15. The method of claim 1 , wherein the carboxylic acid is heated to a temperature in a range of 50 degrees Celsius to 150 degrees Celsius to form the heated carboxylic acid.

16. The method of claim 1 , further comprising adding penflufen to the reaction product in a weight ratio of elemental copper: penflufen in a range of 5:1 to 250:1.

17. The method of claim 1 , wherein the hydrocarbon solvent comprises diesel and the copper compound comprises copper hydroxide.

18. The method of claim 1 , wherein the hydrocarbon solvent comprises a flash point in a range of 65 degrees Celsius to 100 degrees Celsius.

19. The method of claim 1 , wherein the hydrocarbon solvent comprises a flash point in a range of 58 degrees Celsius to 76 degrees Celsius.

20. The method of claim 19 , wherein the copper compound comprises copper hydroxide.

21. A method for producing copper naphthenate, the method comprising:

combining a hydrocarbon solvent and a copper compound to form an intermediate mixture, wherein the intermediate mixture is at a temperature in a range of 50 degrees Celsius to 125 degrees Celsius, wherein the hydrocarbon solvent comprises a flash point in a range of 58 degrees Celsius to 140 degrees Celsius;

heating naphthenic acid to a temperature in a range of 50 degrees Celsius to 150 degrees Celsius to form a heated naphthenic acid; and

combining the intermediate mixture with the heated naphthenic acid to form a reaction product comprising

copper naphthenate, wherein an elemental copper concentration is in a range of 2 percent to 12 percent based on a total weight of the reaction product; and

at least 20 percent by weight hydrocarbon solvent based on the total weight of the reaction product.

22. The method of claim 21 , wherein a weight ratio of carboxylic acid to copper compound is in a range of 3:1 to 10:1.

23. The method of claim 21 , wherein the hydrocarbon solvent comprises diesel and the copper compound comprises copper hydroxide.

24. A wood preservative composition produced by the method of claim 1 .

25. The wood preservative composition of claim 24 , further comprising penflufen.

26. A wood product produced by treating the wood product with the wood preservative composition of claim 24 .

27. The wood preservative composition of claim 25 , wherein a weight ratio of elemental copper: penflufen is in a range of 5:1 to 250:1.

28. A wood product produced by treating the wood product with the wood preservative composition of claim 25 , wherein a penflufen retention in the wood product is in a range of 0.004 kg/m 3 to 0.2 kg/m 3 and an elemental copper retention in the wood product is in a range of 0.5 kg/m 3 to 3.2 kg/m 3 .

Assignments (2)
SECURITY AGREEMENT Recorded Oct 11, 2023
From: KOPPERS PERFORMANCE CHEMICALS, INC.; KOPPERS DELAWARE, INC.
To: PNC BANK, NATIONAL ASSOCIATION, AS THE COLLATERAL AGENT
Reel/Frame 065217/0884 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 6, 2023
From: ISLAM, MD SAYFUL; ZHANG, JUN
To: KOPPERS PERFORMANCE CHEMICALS, INC.
Reel/Frame 063241/0477 →
Continuity (3)
Continuation PCTUS2021064126 · Dec 17, 2021
Provisional Application 63143396 · Jan 29, 2021
Related Publication 20220332008A1 · Oct 20, 2022