Process for producing long chain amino acids and dibasic acids

1. A process for producing long chain amino acid, dibasic acid, short chain alkylamine, and alkanoic acid of the following structures:

from an ammonia or ammonium hydroxide hydrolysis of the mixed amide derivatives of the following structures:

wherein m is an integer from 0 to 10;

n is an integer from 6 to 20;

X is OR or NR 1 R 2 , wherein OR is OH, C 1 -C 8 monohydric alcohol, or C 1 -C 8 polyhydric alcohol, and R 1 and R 2 are each independently hydrogen or C 1 -C 8 alkyl group; comprising:

(1) adding the mixed amide derivatives to an aqueous solution of ammonium hydroxide in the presence or absence of solvent or catalyst;

(2) subjecting the solution or suspension of step (1) to an hydrolysis reaction; and

(3) recovering excess ammonia and solvent in the presence of solvent in step (1) by evaporation to provide a mixture of long chain amino acid and alkylamine or ammonium salts of long chain dibasic acid and alkanoic acid.

2. The process according to claim 1 , wherein the hydrolysis reaction is performed at a temperature from 100° C. to 280° C.

3. The process according to claim 1 , wherein the hydrolysis reaction is performed at a temperature from 160° C. to 220° C.

4. The process according claim 1 , wherein the hydrolysis reaction is performed under a pressure from autogenous to 260 bars.

5. The process according to claim 1 , wherein the solvent is selected from the group consisting of methanol, ethanol, isopropanol, propanol, tetrahydrofuran, dioxane, tert-butanol, isobutanol, butanol, and a mixture of two or more thereof.

6. The process according to claim 1 , wherein the catalyst is selected from the group consisting of alkali and ammonium salts of hydroxide, bicarbonate, carbonate, bisulfite, sulfite, sulfate, nitrate, phosphate, and a mixture of two or more thereof.

7. The process according to claim 1 , wherein a process for separating long chain amino acid and ammonium or alkylamine salts of long chain dibasic acid and alkanoic acid comprises:

(a) crystallizing long chain amino acid by cooling the mixture of hydrolysis solution or suspension;

(b) separating the long chain amino acid by means of solid-liquid separation to provide a mother containing an ammonium or alkylamine salts of long chain dibasic acid and alkanoic acid;

(c) adding an acid to the mother liquor of step (b) to precipitate the long chain dibasic acid and to form the alkanoic acid in the absence or presence of an extractant solvent;

(d) separating the long chain dibasic acid by means of solid-liquid separation; and

(e) recovering the alkanoic acid from the mother liquor or an extractant phase.

8. The process according to claim 1 , wherein a process for separating long chain amino acid and ammonium or alkylamine salts of long chain dibasic acid and alkanoic acid comprises:

(a) adding an acid and an extractant solvent to the the mixture of hydrolysis solution or suspension;

(b) separating the aqueous phase of an acid salt of long chain amino acid and alkylamine and the extractant phase containing long chain dibasic acid, alkanoic acid, fatty acid, and impurities;

(c) crystallizing long chain dibasic acid by cooling the extractant phase and separating the long chain dibasic acid by means of solid-liquid separation;

(d) recovering the alkanoic acid from the mother liquor of step (c) by distillation;

(e) neutralizing the aqueous solution of step (b) with a basic agent to neutral pH to precipitate the long chain amino acid; and

(f) recovering the long chain amino acid of step (e) by means of solid-liquid separation.

9. The process according to claim 1 , wherein a process for purifying long chain amino acid comprises:

(a) dissolving the long chain amino acid in an acid aqueous solution in the presence of an extractant solvent;

(b) separating the aqueous phase containing the acid salt of long chain amino acid and the extractant solvent phase rich in fatty acid and colored materials;

(c) neutralizing the aqueous phase with a basic agent to precipitate the long chain amino acid; and

(d) recovering the long chain amino acid by means of solid-liquid separation.

10. The process according to claim 1 , wherein the acid is selected from the group consisting of hydrochloric acid, hydrobromic acid, hydroiodic acid, sulfuric acid, nitric acid, phosphoric acid, methanesulfonic acid, ethanesulfonic acid, propanesulfonic acid, isethionic acid, benzenesulfonic acid, toluenesulfonic acid, xylenesulfonic acid, sulfamic acid, malic acid, maleic acid, tartaric acid, glycolic acid, lactic acid, citric acid, oxalic acid, formic acid, acetic acid, propionic acid, and a mixture of two or more thereof.

11. The process according to claim 1 , wherein the acid is sulfuric acid.

12. The process according to claim 1 , wherein the extractant solvent is selected from the group consisting of butyl formate, isobutyl formate, butyl acetate, isobutyl acetate, propyl acetate, isopropyl acetate, ethyl acetate, ethyl propionate, octyl acetate, benzene, toluene, xylene, cumene, anisole, diethyl ether, diisopropyl ether, dibutyl ether, methyl tert-butyl ether, ethyl tert-butyl ether, methyl tetrahydrofuran, petroleum ether, cyclohexane, dichloroethane, methylene chloride, chloroform, carbon tetrachloride, and trifluoromethylbenzene, n-butanol, isobutanol, amyl alcohol, isoamyl alcohol, hexanol, cyclohexanol, 2 -ethylhexanol, isooctanol, sec-octanol, butanone, pentanone, hexanone, cyclohexanone, methyl isobutyl ketone, and a mixture of two or more thereof.

13. The process according to claim 1 , wherein the extractant solvent is toluene.

14. The process according to claim 1 , wherein the basic agent is selected from the group consisting of ammonia, alkali and ammonium salts of hydroxide, bicarbonate, carbonate, bisulfite, sulfite, carboxylate, and a mixture of two or more thereof.

15. The process according to claim 1 , wherein the basic agent is ammonia or ammonium hydroxide.

16. The process according to claim 1 , wherein the long chain amino acids are 9-aminononanoic acid, 11-aminoundecanoic acid, or 13- aminotridecanoic acid.

17. The process according to claim 1 , wherein the long chain amino acid is 11-aminoundecanoic acid.

18. The process according to claim 1 , wherein the long chain dibasic acids are sebacic acid, dodecanedioic acid, or brassylic acid.

19. The process according to claim 1 , wherein the long chain dibasic acid is dodecanedioic acid.

20. The process according to claim 1 , wherein the short chain alkanoic acids are heptanoic acid and pelargonic acid.

21. The process according to claim 1 , wherein the alkylamines are n-hexylamine and n-octylamine.