US 12,215,064 B2Granted

Compounds for chromatographic separation of rare earth elements and s-, p-, d-metals, method of separation, and use thereof

AssigneeUstav Organicke Chemie A Biochemie Av Cr, V.V.I.

InventorMiloslav Polasek

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Abstract

The present invention relates to compounds of general formula (I), wherein —X is selected from a group consisting of H; C1 to C6, alkyl; halogen (F, Cl, Br or I); Y is selected from a group consisting of nitrogen; N-oxide; Z1, Z2, Zm, wherein m is 1 or 2, are independently selected from the group consisting of —CH2—CH2— and —CH2—CH2—CH2; A, Am, wherein m is 1 or 2, are independently selected from H; —CH2COOH; —CH2C(O)NH2; —CH2P(O)(OH)2, and n is 1 or 2; R1, R2, R3 are independently H; C1 to C6, alkyl; C1 to C6 alkyloxy; C6 to C10 aryloxy; benzyloxy; C1 to C6 alkylthio; C6, to C10 arylthio; F; Cl; Br; I; OH; SH; NH2; C1 to C6, alkylamino; di(C1 to C6, alkyl)amino; C1 to C6 acylamino; di(C1 to C6 acyl) amino; C6 to C10 arylamino; di(C6 to C10 aryl)amino; CN; OH; nitro; COORn, C(O)NHRn, C(O)N(Rn)2, wherein Rn is independently H or C1 to C10 alkyl or C6, to C10 aryl; and/or neighboring two of R1, R2, R3 together with neighboring two carbon atoms of the aromatic cycle form a six-membered ring, optionally substituted with one or more substituents independently selected from the group consisting of OH, SH, CF3, F, Cl, Br, I, C1 to C6, alkyl, C1to C6, alkyloxy, C1 to C6 alkylthio, NH2, C1 to C6 alkylamino, di(C1 to C6 alkyl)amino, NO2, COOH, COORn, C(O)NHRn, C(O)N(Rn)2, wherein Rn is WO 2020/244686 A1 independently H or C1 to C10 alkyl or C6 to C10 aryl; with the proviso that when n is 2 and all of Z1, Z2, Zm are —CH2—CH2—, then A is not —CH2COOH; for chromatographic separation of rare earth elements and/or s-, p- and d-block metals, as well as to the method of the separation of rare earth elements.

Claims18

Dependent claims

A method of chromatographic separation comprising:

providing a mixture of at least one metal ion selected from Ce, Dy, Er, Eu, Gd, Ho, La, Lu, Nd, Pr, Pm, Sm, Sc, Tb, Tm, Yb, Y, alkaline earth metals, Al, Ga, In, Tl, Sn, Pb, Bi and transitional metals, and at least one further metal ion, wherein said further metal ion is selected from rare earth metal ions, transition metal ions, non-transition metal ions, and actinide ions,
contacting the mixture with at least one compound of general formula (I) to form a chelates;
applying the chelates to a chromatographic column;
and
eluting from the chromatographic column a chelate of the at least one metal ion and a chelate of the at least one further metal ion;
wherein:
formula (I) is:
X is H, C1 to C6 alkyl, F, Cl, Br or I;
Y is N or N-oxide;
Z1, Z2, and Zm, wherein m is 1 or 2, are -CH2-CH2-or -CH2-CH2-CH2-;
A and Am, wherein m is 1 or 2, are independently H, -CH2COOH, -CH2C(O)NH2;
-CH2P(O)(OH)2, or
n is 1 or 2;
R1, R2, and R3 are independently H, C1 to C6 alkyl, C1 to C6 alkyloxy, C6 to C10 aryloxy, benzyloxy, C1 to C6 alkylthio, C6 to C10 arylthio, F, Cl, Br, I, OH, SH, NH2, C1 to C6 alkylamino, di (C1 to C6 alkyl) amino, C1 to C6 acylamino, di(C1 to C6 acyl) amino, C6 to C10 arylamino, di(C6 to C10 aryl) amino, CN, OH, nitro, COORn, C(O)NHRn, or C(O)N(Rn)2, wherein Rn is independently H, C1 to C10 alkyl, or C6 to C10 aryl;
and/or wherein any neighboring two of R1, R2, and R3 together with any neighboring two carbon atoms of the aromatic cycle form a six-membered ring, optionally substituted with one or more substituents independently selected from the group consisting of OH, SH, CF3, F, Cl, Br, I, C1 to C6 alkyl, C1 to C6 alkyloxy, C1 to C6 alkylthio, NH2, C1 to C6 alkylamino, di(C1 to C6 alkyl) amino, NO2, COOH, COORn, C(O)NHRn, or C(O)N(Rn)2, wherein Rn is independently H, C1 to C10 alkyl, C6 to C10 aryl;
with the proviso that when n is 2 and all of Z1, Z2, Zm are -CH2-CH2-, then A is not -CH2COOH.

13 more elements

A compound represented by formula (Ia),

X is H, C1 to C6 alkyl, F, Cl, Br or I;
Y is N or N-oxide;
Z1, Z2, and Zm, wherein m is 1 or 2, are -CH2-CH2-or -CH2-CH2-CH2-;
A and Am, wherein m is 1 or 2, are independently H, -CH2COOH, -CH2C(O)NH2;
or -CH2P(O)(OH)2, and wherein at most one of A and Am is H;
n is 1 or 2;
R1, R2, and R3 are independently H, C1 to C6 alkyl, C1 to C6 alkyloxy, C6 to C10 aryloxy, benzyloxy, C1 to C6 alkylthio, C6 to C10 arylthio, F, Cl, Br, I, OH, SH, NH2, C1 to C6 alkylamino, di(C1 to C6 alkyl) amino, C1 to C6 acylamino, di(C1 to C6 acyl)amino, C6 to C10 arylamino, di(C6 to C10 aryl)amino, CN, OH, nitro, COORn, C(O)NHRn, or C(O)N(Rn)2, wherein Rn is independently H, C1 to C10 alkyl, or C6 to C10 aryl;
and/or wherein any neighboring two of R1, R2, and R3 together with any neighboring two carbon atoms of the aromatic cycle form a six-membered ring, optionally substituted with one or more substituents independently selected from the group consisting of OH, SH, CF3, F, Cl, Br, I, C1 to C6 alkyl, C1 to C6 alkyloxy, C1 to C6 alkylthio, NH2, C6 to C10 alkylamino, di(C6 to C10 alkyl) amino, NO2, COOH, COORn, C(O)NHRn, or C(O)N(Rn)2, wherein Rn is independently H, C1 to C10 alkyl, C6 to C10 aryl;
with the proviso that:
when n is 2, all of Z1, Z2, Zm are -CH2-CH2-, then A is not -CH2COOH;
when Y is nitrogen, then X is not H;
and
when n is 1, all of Z1, Z2, Zm are -CH2-CH2-, and Y is nitrogen, then X is not halogen.

10 more elements

Dependencies are inferred from the claim text.

Facts

Application: 17/616,340Filed 28 May 2020
Priority: EP 191784925 Jun 2019
Published: US 2022/0259119 A118 Aug 2022
Granted: 4 Feb 2025
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07B 59/00
Introduction of isotopes of elements into organic compounds
C07B 59/002
Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se: heterocyclic compounds
B01D 15/424
Characterised by the development mode, e.g. by displacement or by elution: elution mode
C07D 401/06
Containing two hetero rings: linked by a carbon chain containing only aliphatic carbon atoms

Family

US 2022/0259119 A1Pre-grant publication · published 18 Aug 2022
US 12,215,064 B2This patent

From the US filing history. Foreign family members aren’t listed.

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