N,N-dihydrocarbonylamide carboxylic acid, preparation method therefor and use thereof
The present invention provides an N,N-dihydrocarbyl amide carboxylic acid, preparation method therefor and use thereof. The N,N-dihydrocarbyl amide 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 mixed rare earth raw material, and separating elements such as aluminum, iron, radioactive thorium, radioactive uranium and actinide from 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 can withstand strong acid and strong alkali without decomposition.
1. An N,N-dihydrocarbyl amide 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 C6 or more hydrocarbyl;
R 3 is a linear or branched, saturated or unsaturated, and unsubstituted C6 or more hydrocarbyl;
n is a natural number from 1 to 10.
2. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched, saturated or unsaturated, and unsubstituted C6-C30 hydrocarbyl.
3. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a branched, saturated or unsaturated, and unsubstituted C6 or more hydrocarbyl.
4. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched and unsubstituted C6-C30 alkyl.
5. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein n is a natural number from 1 to 6.
6. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein R 1 and R 2 are independently
wherein 2≤a+b≤10, and represents a connecting site.
7. The N,N-dihydrocarbyl amide 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,
8. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 3 is selected from a linear or branched, saturated or unsaturated, and unsubstituted C6-C30 hydrocarbyl.
9. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 3 is selected from a linear or branched, unsaturated, and unsubstituted C6 or more hydrocarbyl.
10. The N,N-dihydrocarbyl amide 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,
11. A method for preparing the N,N-dihydrocarbyl amide carboxylic acid according to claim 1 comprising a step of:
mixing and reacting an N,N-dihydrocarbyl secondary amine represented by Formula II and an anhydride compound represented by Formula III to obtain the N,N-dihydrocarbyl amide carboxylic acid represented by Formula I, as shown in the following Reaction Scheme:
or mixing and reacting the N,N-dihydrocarbyl secondary amine represented by Formula II and a carboxylic acid-monoacyl chloride compound represented by Formula IV to obtain the N,N-dihydrocarbyl amide carboxylic acid represented by Formula I, as shown in the following Reaction Scheme:
12. The method for preparing the N,N-dihydrocarbyl amide carboxylic acid according to claim 11 , wherein a molar ratio between the N,N-dihydrocarbyl secondary amine represented by Formula II and the anhydride compound represented by Formula III is 1:(0.8-1.2); or
the molar ratio of the N,N-dihydrocarbyl secondary amine represented by Formula II and the carboxylic acid-mono acyl chloride compound represented by Formula IV is 1:(0.8-1.2).
13. The method for preparing the N,N-dihydrocarbyl amide carboxylic acid according to claim 11 , wherein the N,N-dihydrocarbyl secondary amine represented by Formula II and the anhydride compound represented by Formula III are mixed and reacted at a temperature of 0° C. to 125° C. for 0.5 to 4 hours; or
the N,N-dihydrocarbyl secondary amine represented by Formula II and the carboxylic acid-mono acyl chloride compound represented by Formula IV are mixed and reacted at temperature of 0° C. to 125° C. for 0.5 to 4 hours.
14. The method for preparing the N,N-dihydrocarbyl amide carboxylic acid according to claim 11 , wherein the N,N-dihydrocarbyl secondary amine represented by Formula II and the anhydride compound represented by Formula III are mixed and reacted in the absence of a solvent or in a solvent; or
the N,N-dihydrocarbyl secondary amine represented by Formula II and the carboxylic acid-monoacyl chloride compound represented by Formula IV are mixed and reacted in the absence of a solvent or in a solvent; and
when mixed in the solvent, the solvent is an inert solvent and selected from any one or a combination of at least two selected from the group consisting of hexane, dichloromethane, petroleum ether, toluene, xylene and kerosene.
15. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched, saturated or unsaturated, and unsubstituted C6-C18 hydrocarbyl.
16. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a branched, saturated or unsaturated, and unsubstituted C6-C30 hydrocarbyl.
17. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a branched, saturated or unsaturated, and unsubstituted C6-C10 hydrocarbyl.
18. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched and unsubstituted C6-C18 alkyl.
19. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 1 and R 2 are each independently a linear or branched and unsubstituted C6-C10 alkyl.
20. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 3 is selected from a linear C10 or more alkenyl.
21. The N,N-dihydrocarbyl amide carboxylic acid according to claim 1 , wherein, R 3 is selected from a linear C10-C18 alkenyl.