Ether amine compounds and use thereof as flotation collector
The present invention relates to a compound of formula (I): in which: the R 1 and R 2 groups, which may be identical or different, are, independently of one another, a saturated or unsaturated, linear, branched or cyclic hydrocarbon group having from 1 to 15 carbon atoms, preferably from 1 to 10 carbon atoms; the R 3 and R 4 groups, which may be identical or different, are selected, independently of one another, from a hydrogen atom, a methyl group or an ethyl group; the R, R 6 and R 7 groups, which may be identical or different, are selected, independently of one another, from a hydrogen atom or an alkyl group comprising from 1 to 6 carbon atoms; n is an integer of 0 to 20; and m is an integer of 1 to 6.
1. A compound of formula (I):
wherein:
the group R 1 is hexyl and the group R 2 is methyl;
the groups R 3 and R 4 , which may be identical or different, are selected, independently of each other, from a hydrogen atom, a methyl group or an ethyl group;
the groups R 5 , R 6 and R 7 , which may be identical or different, are selected, independently of each other, from a hydrogen atom or an alkyl group comprising from 1 to 6 carbon atoms;
n is an integer ranging from 0 to 20, inclusive; and
m is an integer ranging from 1 to 6, inclusive.
2. The compound according to claim 1 , wherein n is an integer ranging from 0 to 10, inclusive.
3. The compound according to claim 1 wherein the groups R 3 and R 4 , which may be identical or different, are selected, independently of each other, from a hydrogen atom or a methyl group.
4. The compound according to claim 1 wherein m is an integer ranging from 1 to 4, inclusive.
5. A process for manufacturing a compound of formula (I) according to claim 1 comprising the steps of:
a) a step of reacting a compound of formula (II):
with an α,β-unsaturated nitrile;
b) a step of hydrogenation of the product of step a); and
c) when m is an integer greater than 1, reacting the product derived from step a) and step b) in series (m−1) times with the α,β-unsaturated nitrile, and then with dihydrogen,
wherein R 1 , R 2 , R 3 , R 4 , m and n are as defined in claim 1 .
6. The process according to claim 5 , wherein the α,β-unsaturated nitrile is selected from acrylonitrile or methacrylonitrile.
7. The process according to claim 5 wherein the mole ratio of the α,β-unsaturated nitrile to the compound of formula (II) ranges from 0.8 to 1.2, inclusive.
8. The process according to claim 5 wherein the mole ratio of the α,β-unsaturated nitrile to the compound of formula (II) ranges from 1.01 to 1.1, inclusive.
9. The process according to claim 5 wherein the step a) reaction of said compound of formula (II) with the α,β-unsaturated nitrile is performed in the presence of at least one basic catalyst (BC).
10. The process according to claim 9 , wherein the basic catalyst (BC) is selected from the group consisting of alkali metal hydroxides, alkaline-earth metal hydroxides, alkali metal alkoxides, alkali metal hydrides, basic resins, quaternary ammonium hydroxides, and mixtures thereof.
11. The process according to claim 5 wherein said process comprises, prior to the step a), a step of reacting an alcohol of formula (III):
R 1 —CH(OH)—R 2 (III),
wherein the group R 1 is hexyl and the group R 2 is methyl,
with n compound(s) of formula (IV):
in which:
the groups R 3 and R 4 , which may be identical or different, are selected, independently of each other, from a hydrogen atom, a methyl group or an ethyl group, and
n is an integer ranging from 0 to 20, inclusive, whereby the compound of Formula (II) is produced.
12. A method of manufacturing a lubricant, a cationic surfactant, an ore flotation collector, a corrosion inhibitor, a fuel additive, or a crosslinking agent for epoxy resins comprising incorporating the compound of formula (I) according to claim 1 into a lubricant, a cationic surfactant, an ore flotation collector, a corrosion inhibitor, a fuel additive, or a crosslinking agent for epoxy resins.
13. The compound according to claim 1 , wherein n is equal to 0, R 5 , R 6 and R 1 denote a hydrogen atom, and m is an integer ranging from 2 to 6.