N,N-DIHYDROCARBONYL AMINO CARBOXYLIC ACID, PREPARATION METHOD THEREFOR AND USE THEREOF

Abstract

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.

Claims

1. An N,N-dihydrocarbonyl amino carboxylic acid with a structure represented by Formula I: ##STR00043## wherein, R.sub.1 and R.sub.2 are each independently a linear or branched, saturated or unsaturated, and substituted or unsubstituted C7 or more hydrocarbonyl; R.sub.3 is a linear or branched, saturated or unsaturated, and substituted or unsubstituted hydrocarbonyl; X is H or OH; n is a natural number from 1 to 10.

2. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.1 and R.sub.2 are each independently a linear or branched, saturated or unsaturated, and substituted or unsubstituted C7-C30 hydrocarbonyl.

3. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.3 is selected from a linear or branched, saturated or unsaturated, and substituted or unsubstituted C6 or more hydrocarbonyl.

4. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.1 and R.sub.2 are each independently a linear or branched, saturated or unsaturated, and substituted or unsubstituted C7-C18 hydrocarbonyl.

5. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.1 and R.sub.2 are each independently a linear or branched, saturated or unsaturated, and unsubstituted C7 or more hydrocarbonyl.

6. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 5, wherein, R.sub.1 and R.sub.2 are each independently a branched, saturated or unsaturated, and unsubstituted C7-C30 hydrocarbonyl.

7. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.1 and R.sub.2 are each independently a linear or branched and unsubstituted C7-C30 alkyl.

8. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.1 and R.sub.2 are each independently a linear or branched and unsubstituted C7-C18 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.sub.1 and R.sub.2 are independently ##STR00044## wherein 3≤a+b≤10, represents a connecting site.

11. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein R.sub.1 and R.sub.2 are independently any one selected from the group consisting of the following groups, wherein represents a connecting site, ##STR00045##

12. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 2, wherein, R.sub.3 is selected from a linear or branched, saturated or unsaturated, and substituted or unsubstituted C6-C30 hydrocarbonyl.

13. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.3 is selected from a linear or branched, unsaturated, and unsubstituted C6 or more hydrocarbonyl.

14. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.3 is a linear C10 or more alkenyl.

15. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein R.sub.3 is any one selected from the group consisting of the following groups, wherein represents a connecting site, ##STR00046##

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 Reaction Scheme: ##STR00047##

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 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. Use of the N,N-dihydrocarbonyl amino carboxylic acid according to claim 1 in preparing an extractant for separating rare earth elements.

22. 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.

23. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.3 is a linear C10-C18 alkenyl.

24. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 9, wherein n is a natural number from 1 to 6.

25. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 1, wherein, R.sub.1 and R.sub.2 are each independently a linear or branched and unsubstituted C7-C10 alkyl.

26. The N,N-dihydrocarbonyl amino carboxylic acid according to claim 5, wherein, R.sub.1 and R.sub.2 are each independently a branched, saturated or unsaturated, and unsubstituted C7-C12 hydrocarbonyl.

Description

MODE OF CARRYING OUT THE INVENTION

[0038] In the following, the technical solution of the present application will be further explained with reference to specific embodiments. It should be understood to those skilled in the art that the detailed description is intended to aid in the understanding of the present application, and should not be regarded as a specific limitation of the present application.

Example 1

[0039] The present Example provides a compound I-1 represented by Formula I, which has a structural Formula as follows:

##STR00007##

[0040] Compound I-1 was prepared by the synthesis route as follows:

##STR00008##

[0041] The synthesis method was as follows: [0042] (1) N,N-diheptyl secondary amine represented by Formula II-1 (21.4 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; octenyl glutaric anhydride compound represented by Formula III-1 (22.5 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0043] (2) the solution 1 was added into the solution 2, the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for two hours; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-1; [0044] (3) compound IV-1 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-1.

[0045] In the present application, compound I-1 was analyzed by NMR:

[0046] .sup.1H NMR (500 MHz, CDCl.sub.3), δ 12.01 (1H), 5.42 (1H), 5.34 (1H), 2.46 (2H), 2.40 (4H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.54 (2H), 1.45 (4H), 1.33 (2H), 1.31 (4H), 1.31 (2H), 1.31 (2H), 1.29 (2H), 1.25 (4H), 1.19 (4H), 0.93 (6H), 0.88 (3H), 0.88 (6H).

[0047] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 134.9, 129.3, 64.6, 64.4 (2C), 34.8 (2C), 31.9, 31.6, 31.3 (2C), 31.2, 29.9, 29.4, 29.0 (2C), 28.0, 27.5, 23.0 (2C), 22.7, 18.7 (2C), 14.1, 14.1 (2C).

Example 2

[0048] The present Example provides a compound I-2 represented by Formula I, which has a structural Formula as follows:

##STR00009##

[0049] Compound I-2 was prepared by the synthesis route as follows:

##STR00010##

[0050] The synthesis method was as follows: [0051] (1) N,N-diisooctyl secondary amine represented by Formula II-2 (24.1 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decenyl glutaric anhydride compound represented by Formula III-2 (25.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0052] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-2; [0053] (3) Compound IV-2 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-2.

[0054] In the present application, compound I-2 was analyzed by NMR:

[0055] .sup.1H NMR (500 MHz, CDCl.sub.3), δ 12.01 (1H), 5.42 (1H), 5.34 (1H), 2.46 (2H), 2.40 (4H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.55 (2H), 1.54 (2H), 1.33 (2H), 1.31 (4H), 1.30 (2H), 1.29 (2H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.25 (2H), 1.25 (4H), 1.19 (4H), 0.99 (6H), 0.88 (3H), 0.88 (6H).

[0056] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 134.9, 129.3, 64.6, 63.1 (2C), 38.0 (2C), 32.3 (2C), 31.9, 31.6, 31.2, 29.9, 29.7, 29.3, 29.3 (2C), 28.0, 27.5, 26.3 (2C), 22.7, 14.1, 14.1 (2C), 11.6 (2C).

Example 3

[0057] The present Example provides a compound I-3 represented by Formula I, which has a structural Formula as follows:

##STR00011##

[0058] Compound I-3 was prepared by the synthesis route as follows:

##STR00012##

[0059] The synthesis method was as follows: [0060] (1) N,N-diisodecyl secondary amine represented by Formula II-3 (29.8 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; dodecenyl pimelic anhydride compound represented by Formula III-3 (32.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0061] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-3; [0062] (3) compound IV-3 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) to obtain compound I-3.

[0063] In the present application, compound I-3 was analyzed by NMR:

[0064] .sup.1H NMR (500 MHz, CDCl.sub.3), δ 11.87 (1H), 5.42 (1H), 5.34 (1H), 5.31 (1H), 4.66 (1H), 2.40 (4H), 2.21 (2H), 2.03 (1H), 1.94 (2H), 1.55 (4H), 1.54 (2H), 1.33 (2H), 1.30 (2H), 1.30 (2H), 1.29 (2H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.26 (4H), 1.26 (4H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (4H), 1.25 (4H), 1.19 (4H), 0.99 (6H), 0.88 (3H), 0.88 (6H).

[0065] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 133.5, 132.4, 55.7 (2C), 29.6, 95.0, 38.3 (2C), 37.5, 34.0, 32.6 (2C), 31.8 (2C), 31.9, 29.9, 29.6 (2C), 29.7, 29.7, 29.6, 29.4, 29.3, 28.0, 27.2, 27.1 (2C), 27.0, 26.3 (2C), 24.7, 22.7 (2C), 22.7, 14.1 (2C), 14.1, 11.6 (2C).

Example 4

[0066] The present Example provides a compound I-4 represented by Formula I, which has a structural Formula as follows:

##STR00013##

[0067] Compound I-4 was prepared by the synthesis route as follows:

##STR00014##

[0068] The synthesis method was as follows: [0069] (1) N,N-dioctadecyl secondary amine represented by Formula II-4 (52.1 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; hexadecenyl azelaic anhydride compound represented by Formula III-4 (37.8 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0070] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-4; [0071] (3) compound IV-4 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-4.

[0072] In the present application, compound I-4 was analyzed by NMR:

[0073] .sup.1H NMR (500 MHz, CDCl.sub.3), δ11.87 (1H), 5.42 (1H), 5.34 (1H), 2.46 (2H), 2.43 (4H), 2.21 (2H), 2.03 (1H), 1.94 (2H), 1.54 (2H), 1.36 (4H), 1.33 (2H), 1.33 (2H), 1.30 (2H), 1.30 (2H), 1.29 (2H), 1.29 (4H), 1.27 (4H), 1.26 (48H), 1.26 (4H), 1.26 (16H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 0.88 (3H), 0.88 (6H).

[0074] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 133.5, 132.4, 64.3, 57.6 (2C), 34.0, 33.2, 32.2, 31.9, 31.9 (2C), 29.9, 29.7, 29.7, 29.7, 29.6 (6C), 29.6 (20C), 29.3, 29.3 (2C), 29.3 (2C), 29.0, 28.3 (2C), 28.0, 27.3 (2C), 27.2, 24.7, 22.7, 22.7 (2C), 14.1, 14.1 (2C).

Example 5

[0075] The present Example provides a compound I-5 represented by Formula I, which has a structural Formula as follows:

##STR00015##

[0076] Compound I-5 was prepared by the synthesis route as follows:

##STR00016##

[0077] The synthesis method was as follows: [0078] (1) N,N-dieicosyl secondary amine represented by Formula II-5 (57.8 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; dodecenyl adipic anhydride compound represented by Formula III-5 (29.4 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0079] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-5; [0080] (3) compound IV-5 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) to obtain compound I-5.

[0081] In the present application, compound I-5 was analyzed by NMR:

[0082] .sup.1H NMR (500 MHz, CDCl.sub.3), δ 11.87 (1H), 5.42 (1H), 5.34 (1H), 5.31 (1H), 4.66 (1H), 2.43 (4H), 2.33 (2H), 2.03 (2H), 1.94 (2H), 1.54 (2H), 1.37 (4H), 1.33 (2H), 1.30 (2H), 1.30 (2H), 1.29 (2H), 1.29 (4H), 1.27 (4H), 1.26 (4H), 1.26 (8H), 1.26 (56H), 1.25 (2H), 0.88 (3H), 0.88 (6H).

[0083] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 133.5, 132.4, 94.4, 51.4 (2C), 37.2, 34.4, 31.9, 31.9 (2C), 29.9, 29.7, 29.7, 29.6, 29.6, 29.6 (24C), 29.3, 29.3 (2C), 29.3 (2C), 28.6 (2C), 28.0, 27.3 (2C), 26.4, 25.5, 22.7, 22.7 (2C), 14.1 (2C), 14.1.

Example 6

[0084] The present Example provides a compound I-6 represented by Formula I, which has a structural Formula as follows:

##STR00017##

[0085] Compound I-6 was prepared by the synthesis route as follows:

##STR00018##

[0086] The synthesis method was as follows: [0087] (1) N,N-diisooctenyl secondary amine represented by Formula II-6 (23.8 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decenyl azelaic anhydride compound represented by Formula III-6 (30.8 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0088] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-6; [0089] (3) compound IV-6 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-6.

[0090] In the present application, compound I-6 was analyzed by NMR:

[0091] .sup.1H NMR (500 MHz, CDCl.sub.3), δ11.87 (1H), 5.92 (1H), 5.42 (1H), 5.34 (1H), 3.23 (2H), 2.21 (2H), 2.18 (4H), 2.03 (1H), 2.00 (4H), 1.94 (2H), 1.54 (2H), 1.38 (4H), 1.33 (2H), 1.33 (2H), 1.30 (2H), 1.29 (2H), 1.29 (4H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 0.93 (6H), 0.88 (3H), 0.85 (6H).

[0092] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 133.5, 132.4, 124.6 (2C), 116.6 (2C), 62.0, 34.0, 33.4, 32.4, 31.9, 29.9, 29.7, 29.7, 29.7, 29.6 (2C), 29.3, 29.0, 28.3 (2C), 28.0, 28.0 (2C), 27.2, 24.7, 23.1 (2C), 22.7, 11.8 (2C), 14.1, 14.1 (2C).

Example 7

[0093] The present Example provides a compound I-7 represented by Formula I, which has a structural Formula as follows:

##STR00019##

[0094] Compound I-7 was prepared by the synthesis route as follows:

##STR00020##

[0095] The synthesis method was as follows: [0096] (1) N,N-diisodecenyl secondary amine represented by Formula II-7 (29.3 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; octadecenyl tridecandioic anhydride compound represented by Formula III-7 (47.6 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0097] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-7; [0098] (3) compound IV-7 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-7.

[0099] In the present application, compound I-7 was analyzed by NMR:

[0100] .sup.1H NMR (500 MHz, CDCl.sub.3), δ 11.87 (1H), 5.92 (2H), 5.42 (1H), 5.34 (1H), 3.23 (2H), 2.21 (2H), 2.18 (4H), 2.03 (1H), 2.00 (4H), 1.94 (2H), 1.54 (2H), 1.33 (2H), 1.33 (2H), 1.33 (4H), 1.31 (4H), 1.31 (4H), 1.30 (2H), 1.30 (2H), 1.30 (2H), 1.29 (2H), 1.29 (4H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.26 (20H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 0.88 (3H), 0.88 (6H), 0.85 (6H).

[0101] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 133.5, 132.4, 124.6 (2C), 116.6 (2C), 62.0, 34.0, 33.4, 32.4, 31.9, 31.9 (2C), 30.0, 29.9, 29.7, 29.7, 29.6 (8C), 29.6, 29.6, 29.6, 29.7 (2C), 29.3, 29.3, 29.0, 28.6 (2C), 28.6 (2C), 28.0, 28.0 (2C), 27.2, 24.7, 22.7, 22.7 (2C), 14.1, 14.1 (2C), 11.8 (2C).

Example 8

[0102] The present Example provides a compound I-8 represented by Formula I, which has a structural Formula as follows:

##STR00021##

[0103] Compound I-8 was prepared by the synthesis route as follows:

##STR00022##

[0104] The synthesis method was as follows: [0105] (1) N,N-didecynyl secondary amine represented by Formula II-8 (28.9 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; eicosyl azelaic anhydride compound represented by Formula III-8 (45.0 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0106] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-8; [0107] (3) compound IV-8 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-8.

[0108] In the present application, compound I-8 was analyzed by NMR:

[0109] .sup.1H NMR (500 MHz, CDCl.sub.3), δ 11.87 (1H), 2.69 (2H), 2.46 (4H), 2.21 (2H), 1.55 (2H), 1.54 (2H), 1.44 (4H), 1.33 (2H), 1.29 (4H), 1.26 (4H), 1.26 (4H), 1.26 (4H), 1.26 (4H), 1.26 (26H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.19 (2H), 1.19 (2H), 1.15 (1H), 1.10 (1H), 0.99 (3H), 0.88 (3H), 0.88 (6H).

[0110] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 83.3 (2C), 81.9 (2C), 56.6, 34.9, 37.3, 34.0, 31.9, 31.9 (2C), 29.9, 29.6, 29.6 (10C), 29.3, 29.3 (2C), 29.0, 28.9, 28.7 (2C), 28.7 (2C), 28.4 (2C), 28.3, 27.7, 27.4, 24.7, 23.5, 22.7, 22.7 (2C), 15.9 (2C), 12.2, 14.1, 14.1 (2C).

Example 9

[0111] The present Example provides a compound I-9 represented by Formula I, which has a structural Formula as follows:

##STR00023##

[0112] Compound I-9 was prepared by the synthesis route as follows:

##STR00024##

[0113] The synthesis method can be carried out with or without a solvent, and the synthesis method with a solvent was as follows: [0114] (1) N,N-dihexadecynyl secondary amine represented by Formula II-9 (45.8 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; myricyl azelaic anhydride compound represented by Formula III-9 (52.0 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0115] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-9; [0116] (3) compound IV-9 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-9.

[0117] In the present application, compound I-9 was analyzed by NMR:

[0118] .sup.1H NMR (500 MHz, CDCl.sub.3), δ11.87 (1H), 2.69 (2H), 2.46 (4H), 2.21 (2H), 1.54 (2H), 1.44 (4H), 1.33 (2H), 1.30 (1H), 1.29 (4H), 1.26 (40H), 1.26 (16H), 1.26 (22H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.19 (2H), 1.19 (2H), 1.19 (2H), 1.15 (1H), 1.00 (1H), 0.88 (3H), 0.88 (3H), 0.88 (3H), 0.88 (6H).

[0119] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 83.3 (2C), 81.9 (2C), 56.9, 43.9, 35.5, 35.1, 34.0, 32.7, 31.9, 31.9, 31.9 (2C), 29.9, 29.9, 29.6, 29.6 (5C), 29.6 (8C), 29.6 (12C), 29.3, 29.3, 29.3 (2C), 29.2, 29.0, 28.7 (2C), 28.7 (2C), 28.4 (2C), 28.0, 27.4, 27.4, 26.1, 24.7, 22.7, 22.7, 22.7 (2C), 19.1, 15.9 (2C), 14.1, 14.1, 14.1 (2C).

Example 10

[0120] The present Example provides a compound I-10 represented by Formula I, which has a structural Formula as follows:

##STR00025##

[0121] Compound I-10 was prepared by the synthesis route as follows:

##STR00026##

[0122] The synthesis method can be carried out with or without a solvent, and the synthesis method with a solvent was as follows: [0123] (1) N,N-dichlorohexadecyl secondary amine represented by Formula II-10 (47.9 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decenyl glutaric anhydride compound represented by Formula III-10 (32.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0124] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 2 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-10; [0125] (3) compound IV-10 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-10.

[0126] In the present application, compound I-10 was analyzed by NMR: 1H NMR (500 MHz, CDCl.sub.3), δ 12.01 (1H), 5.48 (1H), 5.43 (1H), 3.60 (2H), 3.60 (2H), 2.46 (2H), 2.43 (1H), 2.33 (1H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.77 (2H), 1.77 (2H), 1.54 (2H), 1.49 (2H), 1.49 (2H), 1.46 (2H), 1.35 (1H), 1.33 (2H), 1.31 (2H), 1.31 (2H), 1.30 (2H), 1.29 (2H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.26 (6H), 1.26 (10H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 1.25 (2H), 0.88 (3H), 0.88 (3H), 0.87 (3H).

[0127] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 134.9, 129.3, 77.0, 75.5, 59.9, 44.7, 44.7, 40.1, 38.2, 34.0, 32.3, 31.9, 31.3, 31.3, 31.1, 31.2, 29.9, 29.7, 29.7, 29.6, 29.6, 29.6, 29.6, 29.6, 29.6, 29.6, 29.6, 29.3, 28.8, 28.8, 27.6, 27.5, 27.3, 26.7, 26.3, 26.2, 22.7, 18.5, 16.7, 14.1, 11.6, 11.0.

Example 11

[0128] The present Example provides a compound I-11 represented by Formula I, which has a structural Formula as follows:

##STR00027##

[0129] Compound I-11 was prepared by the synthesis route as follows:

##STR00028##

[0130] The synthesis method was as follows: [0131] (1) N,N-dichlorotetradecanyl secondary amine represented by Formula II-11 (47.9 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decenyl glutaric anhydride compound represented by Formula III-11 (32.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0132] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 2 hours; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-11; [0133] (3) compound IV-11 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) and ZnCl.sub.2 to obtain compound I-11.

[0134] In the present application, compound I-11 was analyzed by NMR: .sup.1H NMR (500 MHz, CDCl.sub.3), δ 12.01 (1H), 5.48 (1H), 5.43 (1H), 3.60 (4H), 2.46 (2H), 2.43 (2H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.77 (4H), 1.54 (2H), 1.49 (4H), 1.46 (4H), 1.33 (2H), 1.31 (4H), 1.30 (2H), 1.29 (2H), 1.26 (2H), 1.26 (2H), 1.26 (2H), 1.26 (20H), 1.25 (4H), 1.25 (4H), 0.88 (3H), 0.87 (6H).

[0135] .sup.13C NMR (500 MHz, CDCl.sub.3), δ 178.4, 134.9, 129.3, 75.2 (2C), 59.6, 44.7 (2C), 38.2, 34.0, 32.3 (2C), 31.9, 31.2, 31.1 (2C), 29.9, 29.7, 29.7, 29.6 (10C), 29.3, 28.8 (2C), 27.5, 27.3 (2C), 26.7 (2C), 26.2 (2C), 22.7, 14.1, 11.0 (2C).

Example 12

[0136] The present Example provides a compound I-12 represented by Formula I, which has a structural Formula as follows:

##STR00029##

[0137] Compound I-12 was prepared by the synthesis route as follows:

##STR00030##

[0138] The synthesis method was as follows: [0139] (1) N,N-dialkyl secondary amine represented by Formula II-12 (49.9 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; eicosyl azelaic anhydride compound represented by Formula III-12 (30.8 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0140] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-12; [0141] (3) compound IV-12 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) to obtain compound I-12.

[0142] In the present application, compound I-12 was analyzed by NMR:

[0143] .sup.1H NMR (500 MHz, CDCl.sub.3), δ11.87 (1H), 5.31 (1H), 5.20 (1H), 4.66 (1H), 2.65 (2H), 2.43 (2H), 2.21 (2H), 2.03 (1H), 1.94 (2H), 1.79 (3H), 1.64 (3H), 1.43 (2H), 1.37 (2H), 1.33 (4H), 1.30 (2H), 1.29 (4H), 1.27 (2H), 1.26 (46H), 1.25 (10H), 0.88 (9H).

[0144] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 138.0, 128.9, 91.7, 64.3, 52.9, 51.2, 48.1, 41.5, 34.0, 31.9, 31.9, 31.8, 30.2, 29.7, 29.7, 29.6 (6C), 29.6 (8C), 29.4, 29.4, 29.3, 29.3, 29.3, 29.3, 29.0, 28.6, 27.8, 27.5, 27.3, 24.7, 24.5, 22.7, 22.7, 22.7, 21.7, 15.2, 14.1, 14.1, 14.1.

Example 13

[0145] The present Example provides a compound I-13 represented by Formula I, which has a structural Formula as follows:

##STR00031##

[0146] Compound I-13 was prepared by the synthesis route as follows:

##STR00032##

[0147] The synthesis method was as follows: [0148] (1) N,N-dialkyl secondary amine represented by Formula II-13 (35.4 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; hexadecanyl pimelic anhydride compound represented by Formula III-13 (36.7 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0149] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-13; [0150] (3) compound IV-13 was reduced in tetrahydrofuran solution dissolved with sodium borohydride-zinc chloride (NaBH.sub.4—ZnCl.sub.2) to obtain compound I-13.

[0151] In the present application, compound I-13 was analyzed by NMR:

[0152] .sup.1H NMR (500 MHz, CDCl.sub.3), δ11.87 (1H), 2.43 (2H), 2.40 (2H), 2.40 (2H), 2.21 (2H), 1.54 (2H), 1.45 (1H), 1.36 (2H), 1.29 (2H), 1.27 (2H), 1.26 (24H), 1.26 (24H), 1.25 (4H), 1.25 (2H), 1.25 (1H), 1.25 (4H), 1.19 (2H), 1.19 (2H), 1.19 (2H), 0.93 (3H), 0.88 (9H).

[0153] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 64.0, 63.0, 57.8, 35.8, 35.1, 34.0, 32.9, 32.6, 31.9, 31.9, 31.9, 31.3, 29.9, 29.9, 29.6 (2C), 29.6 (4C), 29.6 (9C), 29.3, 29.3, 29.3, 29.3, 28.3, 27.3, 27.1, 26.8, 26.5, 25.0, 22.7, 22.7, 22.7, 18.7, 14.1, 14.1, 14.1.

Example 14

[0154] The present Example provides a compound I-14 represented by Formula I, which has a structural Formula as follows:

##STR00033##

[0155] Compound I-14 was prepared by the synthesis route as follows:

##STR00034##

[0156] The synthesis method was as follows: [0157] (1) N,N-dialkyl secondary amine represented by Formula II-14 (24.1 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decenyl glutaric anhydride compound represented by Formula III-14 (25.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0158] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-14; [0159] (3) compound IV-14 was reduced in tetrahydrofuran solution dissolved with sodium borohydride-zinc chloride (NaBH.sub.4—ZnCl.sub.2) to obtain compound I-14.

[0160] In the present application, compound I-14 was analyzed by NMR:

[0161] .sup.1H NMR (500 MHz, CDCl.sub.3), δ12.01 (1H), 5.48 (1H), 5.43 (1H), 2.46 (2H), 2.43 (4H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.54 (2H), 1.36 (4H), 1.33 (2H), 1.30 (2H), 1.29 (6H), 1.27 (4H), 1.26 (18H), 0.88 (9H).

[0162] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 134.9, 129.3, 64.0, 57.6 (2C), 37.6, 34.0, 31.9 (2C), 31.9, 31.2, 29.9, 29.7, 29.7, 29.3 (4C), 29.3, 28.3 (2C), 27.5, 27.3 (2C), 22.7 (2C), 22.7, 14.1 (2C), 14.1.

Example 15

[0163] The present Example provides a compound I-15 represented by Formula I, which has a structural Formula as follows:

##STR00035##

[0164] Compound I-15 was prepared by the synthesis route as follows:

##STR00036##

[0165] The synthesis method can be carried out with or without a solvent, and the synthesis method with a solvent was as follows: [0166] (1) N,N-dialkyl secondary amine represented by Formula II-15 (92.8 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decynyl butanedioic anhydride compound represented by Formula III-15 (22.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0167] (2) the solution 1 was added into the solution 2, the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-15; [0168] (3) compound IV-15 was reduced in tetrahydrofuran solution dissolved with sodium borohydride (NaBH.sub.4) to obtain compound I-15.

[0169] In the present application, compound I-15 was analyzed by NMR:

[0170] .sup.1H NMR (500 MHz, CDCl.sub.3), δ12.01 (1H), 5.31 (1H), 4.60 (1H), 3.54 (4H), 2.84 (2H), 2.81 (1H), 2.46 (2H), 1.96 (2H), 1.44 (2H), 1.31 (4H), 1.29 (2H), 1.28 (4H), 1.26 (96H), 1.25 (8H), 0.88 (9H).

[0171] .sup.13C NMR (500 MHz, CDCl.sub.3), δ177.3, 86.5, 86.3, 80.8, 58.6 (2C), 50.9 (2C), 36.7, 31.9 (2C), 31.2 (2C), 30.9, 29.6 (44C), 29.3 (2C), 29.0, 28.1, 27.1, 26.5 (2C), 22.7 (2C), 22.7, 19.4, 14.1 (2C), 14.1.

Comparative Example 1

[0172] The present Example provides a compound I-d1 represented by Formula I, which has a structural Formula as follows:

##STR00037##

[0173] Compound I-d1 was prepared by the synthesis route as follows:

##STR00038##

[0174] The synthesis method was as follows: [0175] (1) N,N-dialkyl secondary amine represented by Formula II-d1 (18.5 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; octenyl glutaric anhydride compound represented by Formula III-d1 (22.4 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0176] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-d1; [0177] (3) compound IV-d1 was reduced in tetrahydrofuran solution dissolved with sodium borohydride-zinc chloride (NaBH.sub.4—ZnCl.sub.2) to obtain compound I-d1.

[0178] In the present application, compound I-d1 was analyzed by NMR:

[0179] .sup.1H NMR (500 MHz, CDCl.sub.3), δ12.01 (1H), 5.48 (1H), 5.43 (1H), 2.63 (2H), 2.46 (2H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.54 (2H), 1.33 (2H), 1.31 (12H), 1.29 (2H), 1.25 (4H), 1.06 (6H), 0.88 (9H).

[0180] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 134.9, 129.3, 61.3 (2C), 59.0, 38.2, 34.6 (2C), 34.0, 31.9, 31.2, 29.9, 29.7 (2C), 29.4, 27.5, 22.7 (2C), 22.7, 21.0 (2C), 14.1 (2C), 14.1.

Comparative Example 2

[0181] The present Example provides a compound I-d2 represented by Formula I, which has a structural Formula as follows:

##STR00039##

[0182] Compound I-d2 was prepared by the synthesis route as follows:

##STR00040##

[0183] The synthesis method was as follows: [0184] (1) N,N-dihexyl secondary amine represented by Formula II-d2 (18.5 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; decenyl glutaric anhydride compound represented by Formula III-d2 (25.2 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0185] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-d2; [0186] (3) compound IV-d2 was reduced in tetrahydrofuran solution dissolved with sodium borohydride-zinc chloride (NaBH.sub.4—ZnCl.sub.2) to obtain compound I-d2.

[0187] In the present application, compound I-d2 was analyzed by NMR:

[0188] .sup.1H NMR (500 MHz, CDCl.sub.3), δ12.01 (1H), 5.48 (1H), 5.43 (1H), 2.46 (2H), 2.43 (4H), 2.33 (2H), 2.03 (1H), 1.94 (2H), 1.54 (2H), 1.36 (4H), 1.33 (2H), 1.30 (2H), 1.29 (6H), 1.28 (8H), 1.26 (6H), 0.88 (9H).

[0189] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 134.9, 129.3, 64.0, 57.6 (2C), 37.6, 34.0, 31.9, 31.5 (2C), 31.2, 29.9, 29.7, 29.7, 29.3, 28.3 (2C), 27.5, 27.0 (2C), 22.7 (2C), 22.7, 14.1 (2C), 14.1.

Comparative Example 3

[0190] The present Example provides a compound I-d3 represented by Formula I, which has a structural Formula as follows:

##STR00041##

[0191] Compound I-d3 was prepared by the synthesis route as follows:

##STR00042##

[0192] The synthesis method was as follows: [0193] (1) N,N-dialkenyl secondary amine represented by Formula II-d3 (15.3 g, 0.10 mol) was dissolved in toluene (20 mL) to obtain solution 1; octadecenyl tridecanedioic anhydride compound represented by Formula III-d3 (47.6 g, 0.10 mol) was dissolved in toluene (30 mL) to obtain solution 2; [0194] (2) the solution 1 was added into the solution 2, and the thus obtained mixture was stirred while heating to 80° C. and then kept at 80° C. for 1 hour; after the reaction was finished, toluene was removed by concentrating in vacuum to obtain compound IV-d3; [0195] (3) compound IV-d3 was reduced in tetrahydrofuran solution dissolved with sodium borohydride-zinc chloride (NaBH.sub.4—ZnCl.sub.2) to obtain compound I-d3.

[0196] In the present application, compound I-d3 was analyzed by NMR:

[0197] .sup.1H NMR (500 MHz, CDCl.sub.3), δ11.87 (1H), 5.82 (2H), 5.48 (1H), 5.43 (1H), 5.13 (2H), 4.88 (2H), 2.76 (2H), 2.46 (2H), 2.21 (2H), 2.13 (4H), 2.03 (1H), 1.94 (2H), 1.54 (2H), 1.33 (4H), 1.30 (4H), 1.29 (6H), 1.26 (26H), 1.25 (4H), 1.11 (6H), 0.88 (3H).

[0198] .sup.13C NMR (500 MHz, CDCl.sub.3), δ178.4, 133.5, 133.0 (2C), 132.4, 115.8 (2C), 59.8 (2C), 59.5, 41.1 (2C), 38.8, 34.0, 34.0, 33.2, 31.9, 30.0, 29.9, 29.7, 29.7, 29.6 (3C), 29.6 (8C), 29.3, 29.3, 29.0, 27.2, 24.7, 22.7, 18.1 (2C), 14.1.

Test Example 1

[0199] Test for Enrichment of Rare Earth Elements.

[0200] (1) the compounds prepared in the above Examples 1 to 15 and Comparative Examples 1 to 3 were used in weight of (5.51, 6.24, 8.08, 11.52, 11.36, 6.91, 9.83, 9.44, 12.53, 10.96, 10.23, 10.98, 9.36, 6.42, 14.78 and 5.15, 5.51, 8.01) g, respectively;

[0201] (2) The above extractants were respectively mixed with 0.96 mL of 10.8 mol/L sodium hydroxide aqueous solution, and saponified at 25° C. for 5 min to obtain viscous liquid of saponified extractants with saponification degree of 80%;

[0202] (3) at room temperature, the viscous liquid of saponified extractants were mixed with 2000 mL of ion-type rare earth leaching solution for enrichment time of 0.5 h. Ion-type rare earth leaching solution contained 15 rare earth elements including lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium and yttrium, with a total molar concentration of 0.00636 mol/L. pH=6.0 The concentration of rare earth ions in the water phase before and after enrichment was measured, and the total enrichment ratio of rare earth ions E % was calculated;

[0203] The specific test results (total enrichment ratio of rare earth ions) were shown in Table 1.

TABLE-US-00001 TABLE 1 Item Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Total 96.5 97.4 97.5 96.5 97.9 97.6 enrichment ratio E % Item Example 7 Example 8 Example 9 Example 10 Example 11 Example 12 Total 97.7 97.9 97.9 96.6 95.9 98.5 enrichment ratio E % Comparative Comparative Comparative Item Example 13 Example 14 Example 15 Example 1 Example 2 Example 3 Total 97.5 96.9 96.7 94.4 92.9 93.8 enrichment ratio E %

[0204] It can be seen from table 1 that the enrichment rate of N,N-dihydrocarbonyl amino carboxylic acid prepared according to the present application is over 95%, which can be used to enrich rare earth elements from raw materials containing low-concentration rare earth.

Test Example 2

[0205] Test for Separating Yttrium Ion

[0206] (1) the compounds prepared in the above Examples 1 to 15 and Comparative Example 1 were respectively prepared into extractant solutions; to be specific, the extractants prepared in Examples 1 to 15 and Comparative Examples 1 to 3 were taken in weight of 5.51 g, 6.24 g, 8.08 g, 11.52 g, 11.36 g, 6.91 g, 9.83 g, 9.44 g, 12.53 g, 10.96 g, 10.23 g, 10.98 g, 9.36 g, 6.42 g, 14.78 and 5.15 g, 5.51 g, 8.01 g, respectively; toluene was taken in weight of 19.5 g, 18.8 g, 16.9 g, 13.5 g, 13.6 g, 18.1 g, 15.2 g, 15.6 g, 12.5 g, 14.0 g, 14.8 g, 14.0 g, 15.6 g, 18.6 g, 10.2 g and 19.9 g, 19.5 g, 17.0 g respectively; the above two components were mixed to obtain extractant solutions with concentration of 0.52 mol/L and a total volume of 25 mL;

[0207] (2) the above extractant solutions were respectively mixed with 0.96 mL of 10.8 mol/L sodium hydroxide aqueous solution, and saponified at 25° C. for 5 min to obtain solution of saponified extractants with saponification degree of 80%;

[0208] (3) at room temperature, 25 mL of the saponified extractant solutions and 25 mL of mixed rare earth solution were mixed and extracted for 0.5 h. The mixed rare earth solution contained 15 rare earth elements including lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium, lutetium and yttrium, with a concentration of 0.020 mol/L for each element. The concentrations of rare earth ions in aqueous phase before and after extraction were measured, and the relative separation coefficient .sub.Ln/Y of each rare earth ion (Ln) relative to yttrium ion (Y) was calculated;

[0209] The specific test results (relative separation coefficient .sub.Ln/Y of rare earth ions (Ln) relative to yttrium ions (Y)) were shown in Table 2.

TABLE-US-00002 TABLE 2 Ce/ Nd/ Sm/ Eu/ Gd/ Tb/ Dy/ Ho/ Tm/ Yb/ β.sub.Ln/Y La/Y Y Pr/Y Y Y Y Y Y Y Y Er/Y Y Y Lu/Y Example 1.12 1.27 1.77 2.08 3.00 2.94 2.16 2.24 2.28 2.39 2.48 2.59 2.88 3.15 1 Example 1.20 1.60 1.86 2.16 3.05 3.52 2.33 2.79 2.36 2.21 2.30 2.93 2.75 3.20 2 Example 1.11 1.30 1.72 2.06 3.01 2.96 2.18 2.26 2.29 2.37 2.46 2.57 2.85 3.14 3 Example 1.09 1.29 1.72 2.06 3.01 2.96 2.18 2.26 2.30 2.39 2.48 2.59 2.88 3.14 4 Example 1.12 1.27 1.72 2.06 3.01 2.96 2.18 2.27 2.29 2.37 2.47 2.57 2.85 3.11 5 Example 1.13 1.30 1.73 2.07 3.02 2.98 2.20 2.28 2.30 2.39 2.49 2.62 2.90 3.17 6 Example 1.14 1.31 1.73 2.07 3.02 2.98 2.20 2.28 2.30 2.39 2.50 2.62 2.91 3.19 7 Example 1.10 1.29 1.72 2.06 3.01 2.96 2.18 2.26 2.30 2.39 2.48 2.59 2.88 3.15 8 Example 1.21 1.32 1.82 2.08 3.02 2.97 2.19 2.28 2.32 2.42 2.51 2.61 2.97 3.35 9 Example 1.10 1.23 1.77 2.09 3.06 2.99 2.28 2.29 2.33 2.42 2.50 2.56 2.83 3.11 10 Example 1.13 1.32 1.80 2.04 3.05 2.98 2.12 2.23 2.32 2.41 2.48 2.54 2.86 3.13 11 Example 1.08 1.33 1.73 2.07 3.04 3.00 2.13 2.23 2.35 2.42 2.49 2.51 2.89 3.18 12 Example 1.16 1.30 1.74 2.09 3.03 2.93 2.12 2.29 2.30 2.40 2.43 2.59 2.88 3.19 13 Example 1.14 1.39 1.77 2.08 3.09 2.99 2.23 2.26 2.33 2.42 2.51 2.66 2.91 3.27 14 Example 1.28 1.35 1.75 2.05 3.12 3.02 2.24 2.27 2.32 2.43 2.54 2.68 2.91 3.29 15 Com- 0.98 1.18 1.50 1.84 2.87 2.91 2.11 2.16 2.04 2.13 2.21 2.42 2.71 2.97 parative Example 1 Com- 0.88 1.05 1.57 1.82 2.92 2.90 2.10 2.18 2.07 2.11 2.17 2.44 2.69 2.95 parative Example 2 Com- 1.03 1.21 1.55 1.94 2.91 2.93 2.10 2.15 2.17 2.19 2.25 2.43 2.68 2.94 parative Example 3

[0210] It can be seen from table 2 that the amino carboxylic acid provided in this application can be used to separate and purify yttrium from mixed rare earth raw materials.

Test Example 3

[0211] Stability Test

[0212] The stability of compound I-1 prepared in the above Example 1 was tested by the following procedure: compound I-1 was prepared into an extractant solution by dissolving 43.9 g of compound I-1 in 100 mL of toluene to prepare an extractant solution with a concentration of 1.0 mol/l; 50 mL of extractant solution and 50 mL of hydrochloric acid solution with concentration of 6 mol/L were mixed and stirred for 15 days, and another 50 mL of extractant solution and 50 mL of sodium hydroxide solution with concentration of 6 mol/L were mixed and stirred for 15 days, and then the extractant loss rate in both was tested by NMR.

[0213] The stability of compounds according to Examples 2 to 15 and Comparative Examples 1 to 3 was tested in the same manner as that of compound I-1;

[0214] Specific test results (the extractant loss rate in hydrochloric acid medium and liquid alkali medium) were shown in Table 3 below.

TABLE-US-00003 TABLE 3 extractant loss extractant loss rate in rate in hydrochloric liquid alkali Item acid medium (%) medium (%) Example 1 0.03 0.05 Example 2 0.03 0.04 Example 3 0.03 0.04 Example 4 0.03 0.04 Example 5 0.03 0.04 Example 6 0.04 0.05 Example 7 0.03 0.05 Example 8 0.04 0.05 Example 9 0.03 0.05 Example 10 0.03 0.05 Example 11 0.03 0.05 Example 12 0.03 0.05 Example 13 0.03 0.05 Example 14 0.03 0.05 Example 15 0.03 0.04 Comparative 0.06 0.07 Comparative 0.06 0.07 Comparative 0.06 0.07

[0215] It can be seen from table 3 that the loss rate of N,N-dihydrocarbonyl amino carboxylic acid in hydrochloric acid medium was below 0.04%; and the loss rate in caustic soda liquid was below 0.05%. Therefore, the N,N-dihydrocarbonyl amino carboxylic acids prepared by the present application have excellent chemical stability and can withstand strong acid and strong alkali without decomposition.

[0216] The applicant declares that the N,N-dihydrocarbonyl amino carboxylic acid and its preparation method and use according to the present application are illustrated by the above Examples, but the present application is not limited to the above Examples, which does not mean that the present application should be implemented only by relying on the above Examples. The protection scope of this application is defined by the claims.