Aliphatic-aromatic heterocyclic compounds and uses thereof in metal extractant compositions

Patent metadata

Field	Value
Publication number	US-2016244860-A1
Application number	US-201615048034-A
Country	US
Kind code	A1
Filing date	Feb 19, 2016
Priority date	Feb 20, 2015
Publication date	Aug 25, 2016
Grant date	—

Abstract

The invention relates to an aliphatic-aromatic heterocyclic compound A which comprises at least two heterocyclic rings B and C, to a metal extractant composition E comprising this aliphatic-aromatic heterocyclic compound A and an organic acid D having at least one carboxylic, sulfonic, sulfuric, phosphinic, phosphonic, or phosphoric acid group, and to a process to extract one or more metals M selected from the group consisting of Ni and Co from an aqueous acidic leach solution PL comprising ions of at least one of the metals M, and further, at least one kind of further ions selected from the group consisting of Fe ions, Al ions, Cu ions, Mg ions, Mn ions, and also silicate anions, by mixing the solution PL with an extractant composition E, separating the organic and aqueous phases, and recovering the metal M from the separated organic phase.

First claim

We claim:

1 . An aliphatic-aromatic heterocyclic compound A of formula I, or salts or tautomers thereof, which comprises two rings B and C, each ring being independently five- or six-membered, and each ring having at least one nitrogen atom as heteroatom in the ring structure, wherein at least one of the rings B and C has at least one further heteroatom selected from the group consisting of nitrogen atoms and of oxygen atoms, and wherein at least two of the heteroatoms in at least one of the rings having two or more heteroatoms are directly attached to each other by a chemical bond, and wherein at least one of the rings B and C bears a further substituent R at one or more substitutable position which substituent R has from six to twenty-five carbon atoms which are optionally substituted, and wherein from 1 to 3 carbon atoms is optionally substituted with a nitrogen or oxygen atom

wherein in ring B, there is one heteroatom X1 which is directly bonded to ring atom B1 in ring B, and B1 is selected from the group consisting of a carbon atom and a nitrogen atom, and in ring C, there is one heteroatom Y1 which is directly bonded to ring atom C1 in ring C, and C1 is a carbon atom, and atoms B1 and C1 are connected to each other by a chemical bond which may be a single bond or a double bond, and wherein X2 and Y2 are each separately a sequence of from three atoms, in the case of a five-membered ring, to four atoms in the case of a six-membered ring, and are selected from heteroatoms and carbon atoms.

2 . The aliphatic-aromatic heterocyclic compound A of claim 1 wherein ring B has five ring atoms, and ring C has five or six ring atoms.

3 . The aliphatic-aromatic heterocyclic compound A of claim 1 , wherein the substituent R is selected from the group consisting of a linear alkyl group, a branched alkyl group, a cyclic alkyl group, and an alkyl-substituted aryl group.

4 . The aliphatic-aromatic heterocyclic compound A of claim 1 , wherein the ring B is a five-membered ring having two heteroatoms whereof one is a nitrogen atom, and one further heteroatom selected from the group consisting of nitrogen and oxygen atoms, which two heteroatoms are directly attached to each other by a chemical bond.

5 . The aliphatic-aromatic heterocyclic compound A of claim 1 , wherein the ring B is a five-membered ring having three heteroatoms whereof two are nitrogen atoms, and one further heteroatom selected from the group consisting of nitrogen atoms and of oxygen atoms.

6 . The aliphatic-aromatic heterocyclic compound A of claim 1 , wherein the ring B is a five-membered ring having four heteroatoms whereof all four are nitrogen atoms.

7 . The aliphatic-aromatic heterocyclic compound A of claim 4 , wherein the ring C has five or six atoms in the heterocyclic ring which is either an aromatic ring, or a cycloaliphatic ring having at least one double carbon-carbon bond in the cycloaliphatic ring, and has a nitrogen atom in the 2-position relative to the atom connected to the ring B.

8 . The aliphatic-aromatic heterocyclic compound A of claim 4 , wherein the ring B carries a substituent R which is linear or branched or cyclic alkyl group having from six to twenty-five carbon atoms.

9 . The aliphatic-aromatic heterocyclic compound A of claim 7 wherein the ring C is a pyrrole ring, a pyrazole ring, a triazole ring, a 1,3,5-triazine ring, a pyrazine ring, a pyrimidine, a pyridazine or a pyridine ring.

10 . The aliphatic-aromatic heterocyclic compound A of claim 1 , wherein the ring B is selected from the group consisting of pyrazole, isoxazole, 1,3,4-oxadiazole, 1,2,4-oxadiazole, 1,2,4-triazole, 1,2,3-triazole, and 1,2,3,4-tetrazole.

11 . The aliphatic-aromatic heterocyclic compound A of claim 8 , wherein the ring C carries substituent R at one or more substitutable positions on the ring which is chosen from i) a linear or branched alkyl or alkenyl having from six to twenty-five carbon atoms wherein from one to three carbon atoms are optionally substituted with a nitrogen or oxygen atom; or ii) a cyclohexyl wherein from one to three carbon atoms are optionally substituted with a nitrogen or oxygen atom; N-cyclohexyl; N,N-dicylcohexyl; pyrazole; or phenyl, any of which is optionally substituted with a linear or branched alkyl having from one to six carbon atoms.

12 . A metal extractant composition E comprising an aliphatic-aromatic heterocyclic compound A as defined by claim 1 , and an organic acid D having at least one carboxylic, sulfonic, sulfuric, phosphinic, phosphonic, or phosphoric acid group, or salt thereof.

13 . The metal extractant composition E of claim 12 wherein the organic acid D has at least one carboxylic, sulfonic, sulfuric, phosphinic, phosphonic, or phosphoric acid group attached to an aromatic molecule.

14 . The metal extractant composition E of claim 12 wherein the organic acid D has at least one linear, branched, or cyclic alkyl substituent having from six to twenty-five carbon atoms on the aromatic molecule.

15 . The metal extractant composition E according to claim 12 , wherein the amount of substance-ratio of A and D is from 95 mol:5 mol to 5 mol:95 mol.

16 . The metal extractant composition E according to claim 12 , wherein the mixture of the heterocyclic compound A and the organic acid D is dissolved in an organic solvent S which is not homogeneously miscible with water.

17 . The metal extractant composition E as claimed in claim 16 , wherein the organic solvent S is selected from the group consisting of aliphatic hydrocarbons, and mixed aromatic-aliphatic hydrocarbons.

18 . A process to extract one or more metals M selected from the group consisting of Ni and Co from an aqueous acidic leach solution PL comprising ions of at least one of the metals M, and further, at least one kind of further ions selected from the group consisting of Fe ions, Al ions, Cu ions, Mg ions, Mn ions, and also silicate anions, by
mixing the solution PL with an extractant composition E as defined by claim 12 , until the following condition is fulfilled for the concentration c 1 (M) of metal M in the aqueous phase after mixing during a time t1: [c 0 (M)−c 1 (M)]/[c 0 (M)−c e (M)]>0.1, where c 0 (M) is the concentration of metal M in the solution PL before mixing, and c e (M) is the equilibrium concentration of metal M in the aqueous phase after mixing and reaching the equilibrium, separating the organic and aqueous phases, and recovering the metal M from the separated organic phase by re-extraction with an aqueous phase which is neutral, acidic or alkaline, or by precipitation of the metal M by addition of a chemical compound that forms an insoluble compound with the said metal M.

Assignees

• Cytec Ind Inc
• Univ Court Univ Of Edinburgh

Inventors

• Roebuck James William
• Sassi Thomas
• Fischmann Adam James
• GRIFFIN Violina
• Tasker Peter Anthony

Classifications

• C07D401/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title

• C07D403/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• C22B23/0415

  with acids or salt solutions except ammonium salts solutions · CPC title

• C07D231/12

  with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms · CPC title

• C07D401/14

  containing three or more hetero rings · CPC title