Method of purifying pine chemical compositions from aldehydes

Patent metadata

Field	Value
Publication number	US-10822302-B2
Application number	US-201916695231-A
Country	US
Kind code	B2
Filing date	Nov 26, 2019
Priority date	Nov 26, 2018
Publication date	Nov 3, 2020
Grant date	Nov 3, 2020

Abstract

A method to reduce the aldehyde content of a pine chemical composition is disclosed. The pine chemical composition is selected from gum turpentine, gum rosin, CST BLS, CTO, depitched CTO, DTO, TOH, TOR, TOP, TOFA, fractionated TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, stearic acid, and ester- and amide derivatives thereof. The pine chemical composition is treated with an aldehyde scavenger such as anthranilamide at a temperature between 20° C. to 300° C., for 1 minute to 5 hours.

First claim

The invention claimed is:

1. A method of reducing the aldehyde content of a pine chemical composition, the method comprising:
providing an aldehyde scavenger to react with functional —CHO moiety in the aldehydes;
treating the pine chemical composition with less than 6 wt % of the aldehyde scavenger to form an aldehyde - aldehyde scavenger reaction product;
optionally removing the formed aldehyde - aldehyde scavenger reaction product from the treated pine chemical composition to obtain a purified pine chemical composition;
wherein the aldehyde scavenger is an aromatic primary amine derivative
comprising an —NH2 group and an ortho-carboxamide,

wherein the aromatic primary amine derivative has a molecular weight less than 1000 g/mol, and comprises at least 4 elements in its molecular formula selected from the group of C, H, O, S, N, Cl, F, Br, I, B, Si and P,
wherein the pine chemical composition is a crude tall oil (CTO), or products derived therefrom.

2. The method of claim 1 , wherein the aromatic primary amine derivative is unsubstituted or substituted with 1-3 substituents selected from the group consisting of methyl, ethyl, tert-butyl, methoxy, ethoxy, 1-methylethoxy, cyclopropyloxy, isopropyl, phenylmethoxy, fluoro, chloro, bromo, iodo, trifluoromethyl, trifluoromethoxy, 4-methyl-1-piperazinyl, 3-(4-morpholinyl)propoxy, carbamoyl, nitro, amino, cyano, hydroxyl, dimethylamino, sulfamoyl, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholinyl, aminosulfonyl, acetyl, carboxyl, carbomethoxy, and any combinations thereof.

3. The method of claim 1 , wherein the aromatic primary amine comprising an —NH2 group and an ortho-carboxamide are optionally substituted with one or two substituents selected from the group consisting of methyl, ethyl, methoxy, fluoro, chloro, bromo, iodo, carbamoyl, nitro, amino, cyano, acetyl, carbomethoxy, sulfamoyl, and any combinations thereof.

4. The method of any of claim 1 , wherein the aryl group in the aromatic primary amine derivative represents a phenyl group.

5. The method of claim 1 , wherein the aldehyde scavenger is selected from the group consisting of anthranilamide, 3 amino-2-pyridinecarboxamide, 3-amino-4-pyridinecarboxamide, and derivatives of 2-aminobenzamide wherein the phenyl ring contains 1-3 additional substituents selected from the group consisting of methyl, ethyl, tert-butyl, methoxy, ethoxy, 1-methylethoxy, cyclopropyloxy, phenylmethoxy, fluoro, chloro, bromo, iodo, trifluoromethyl, trifluoromethoxy, 4-methyl-1-piperazinyl, 3-(4-morpholinyl)propoxy, carbamoyl, nitro, amino, cyano, hydroxyl, dimethylamino, sulfamoyl, 1-piperidinyl, 1-pyrrolidinyl, 4-morpholinyl, aminosulfonyl, acetyl, carboxyl, carbomethoxy, and any combinations thereof.

6. The method of claim 1 , wherein at least 50% of the aldehydes is removed from the pine chemical composition.

7. The method of claim 1 , wherein the aldehydes initially present in the pine chemical composition comprises C20 resin aldehydes, and wherein the C20 resin aldehydes content is reduced at least 80% after treatment.

8. The method of claim 1 , wherein the treatment of the pine chemical composition with the aldehyde scavenger is at a temperature of 120-250° C.

9. The method of claim 1 , wherein the aldehyde scavenger is anthranilamide.

10. The method of claim 1 , wherein the pine chemical composition is treated with 0.01-3 wt % of an aldehyde scavenger.

11. The method of claim 1 , wherein the wherein the pine chemical composition is treated with 0.01-3 wt % anthranilamide.

12. The method of claim 1 , wherein the CTO comprises one or more of, depitched CTO, DTO, TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, and stearic acid.

13. The method of claim 1 , wherein the formed aldehyde - aldehyde scavenger reaction product removal from the treated pine chemical composition to obtain a purified pine chemical composition comprises distillation under reduced pressure, wherein the formed aldehyde-aldehyde scavenger reaction product remains in the distillation residue fraction.

14. A pine chemical composition prepared by the method of claim 1 , wherein the pine chemical composition contains an aldehyde-aldehyde scavenger reaction product in an amount of between 0.01 wt. % and 10 wt %.

15. A pine chemical composition prepared by the method of claim 14 , wherein the aldehyde content is less than 1200 ppm.

16. A method of reducing the aldehyde content of a pine chemical composition, the method comprising:
treating the pine chemical composition with less than 6 wt % of anthranilamide at a temperature between 50° C. to about 250° C., for 5 minutes to 24 hours;
wherein at least 50% of the aldehydes is removed from the pine chemical composition, and wherein the pine chemical composition is a CTO or products derived therefrom.

17. The method of claim 16 , wherein the aldehydes initially present in the pine chemical composition comprises C20 resin aldehydes, wherein the C20 resin aldehydes content is reduced at least 80% after treatment, and wherein the CTO comprises one or more of depitched CTO, DTO, TOFA, TOFA dimer, TOFA trimer, TOFA monomer, isostearic acid, and stearic acid.

18. A pine chemical composition prepared by the method of claim 16 , wherein the pine chemical composition contains an aldehyde-anthranilamide reaction product in an amount of between 0.01 wt. % and 10 wt %.

19. A pine chemical composition prepared by the method of claim 18 , wherein the aldehyde content is less than 500 ppm.

20. A pine chemical composition prepared by the method of claim 18 , wherein the aldehyde content is less than 100 ppm.

Assignees

• Kraton Polymers Llc

Inventors

• Lange Jos H M
• Schaapman Mark C

Classifications

• C07G99/00 Primary

  Subject matter not provided for in other groups of this subclass · CPC title

• C07C233/65 Primary

  having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals · CPC title

• C07C231/24

  Separation; Purification · CPC title