N,N-dihydrocarbonyl amino carboxylic acid, preparation method therefor and use thereof
The present application provides an N,N-dihydrocarbonyl amino carboxylic acid, preparation method therefor and use thereof. The N,N-dihydrocarbonyl amino carboxylic acid can be used as an extractant for enriching rare earth elements from raw materials containing low-concentration rare earth elements, separating and purifying yttrium element from a mixed rare earth raw material, and separating elements such as aluminum, iron, radioactive thorium, radioactive uranium and actinide from a mixed rare earth raw material, etc. The compound can be synthesized in a simple and cost-efficient way. As an extractant, it has good chemical stability and has good resistance against strong acid and strong alkali without decomposition.
1. An N,N-dihydrocarbonyl amino carboxylic acid with a structure represented by Formula I:
wherein, R 1 and R 2 are each independently a linear or branched, saturated or unsaturated, and unsubstituted C7-C30 alkyl, alkenyl or alkynyl, or a linear or branched, saturated or unsaturated, and substituted C7-C30 alkyl, alkenyl or alkynyl, wherein the substituents of the alkyl, alkenyl or alkynyl are each independently any one or a combination of at least two selected from the group consisting of halogen, hydroxyl, carboxyl, phenyl, phenoxy, amino, nitro, cyano and thiol;
R 3 is a linear or branched, saturated or unsaturated, and unsubstituted C6-C30 alkyl, alkenyl or alkynyl, or a linear or branched, saturated or unsaturated, and substituted C6-C30 alkyl, alkenyl or alkynyl, wherein the substituents of the alkyl, alkenyl or alkynyl are each independently any one or a combination of at least two selected from the group consisting of halogen, hydroxyl, carboxyl, phenyl, phenoxy, amino, nitro, cyano and thiol;
X is H or OH; and
n is a natural number from 1 to 10.
2. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched, saturated or unsaturated, and unsubstituted C7-C18 alkyl, alkenyl or alkynyl, or a linear or branched, saturated or unsaturated, and substituted C7-C18 alkyl, alkenyl or alkynyl.
3. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear, saturated or unsaturated, and unsubstituted C7-C30 alkyl, alkenyl or alkynyl.
4. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a branched, saturated or unsaturated, and unsubstituted C7-C30 alkyl, alkenyl or alkynyl.
5. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a branched, saturated or unsaturated, and unsubstituted C7-C17 alkyl, alkenyl or alkynyl.
6. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 5 , wherein, R 1 and R 2 are each independently a linear or branched and unsubstituted C7-C30 alkyl.
7. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched and unsubstituted C7-C18 alkyl.
8. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched and unsubstituted C7-C10 alkyl.
9. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein X is H.
10. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein R 1 and R 2 are independently
wherein 3≤a+b≤10, represents a connecting site.
11. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein R 1 and R 2 are independently any one selected from the group consisting of the following groups, wherein represents a connecting site,
12. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 2 , wherein, R 3 is selected from a linear or branched, unsaturated, and unsubstituted C6-C30 alkenyl or alkynyl.
13. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 3 is a linear C10-C30 alkenyl.
14. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein, R 3 is a linear C10-C18 alkenyl.
15. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 , wherein R 3 is any one selected from the group consisting of the following groups, wherein represents a connecting site,
16. A method for preparing the N, N-dihydrocarbonyl amino carboxylic acid according to claim 1 comprising steps of:
mixing and reacting N, N-dihydrocarbonyl secondary amine represented by Formula II and anhydride compound represented by Formula III to obtain N, N-dihydrocarbonyl amide carboxylic acid represented by Formula IV, and then reducing the N, N-dihydrocarbonyl amide carboxylic acid represented by Formula IV with reducing agent to obtain the N, N-dihydrocarbonyl amino carboxylic acid represented by Formula I, as shown in the following
17. The method for preparing the N,N-dihydrocarbonyl amino carboxylic acid according to claim 16 , wherein a molar ratio between the N,N-dihydrocarbonyl secondary amine represented by Formula II and the anhydride compound represented by Formula III is 1: (0.8-1.2).
18. The method for preparing the N,N-dihydrocarbonyl amino carboxylic acid according to claim 16 , wherein the N,N-dihydrocarbonyl secondary amine represented by Formula II and the anhydride compound represented by Formula III are mixed and reacted at temperature of 0° C. to 125° C. for 0.5 to 4 hours.
19. The method for preparing the N,N-dihydrocarbonyl amino carboxylic acid according to claim 16 , wherein the N,N-dihydrocarbonyl secondary amine represented by Formula II and the anhydride compound represented by Formula III are mixed and reacted in the absence of a solvent.
20. The method for preparing the N,N-dihydrocarbonyl amino carboxylic acid according to claim 16 , wherein the N,N-dihydrocarbonyl secondary amine represented by Formula II and the anhydride compound represented by Formula III are mixed and reacted in a solvent.
21. The method for preparing the N,N-dihydrocarbonyl amino carboxylic acid according to claim 20 , wherein the solvent is an inert solvent selected from any one or a combination of at least two selected from the group consisting of hexane, dichloromethane, petroleum ether, toluene, xylene or kerosene.
22. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 9 , wherein n is a natural number from 1 to 6.
23. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 5 , wherein, R 1 and R 2 are each independently a branched, saturated or unsaturated, and unsubstituted C7-C12 hydrocarbonyl.