Catalysts for chemical reactions in a water-surfactant mixture

Patent metadata

Field	Value
Publication number	US-11235316-B2
Application number	US-201716316709-A
Country	US
Kind code	B2
Filing date	Jul 10, 2017
Priority date	Jul 13, 2016
Publication date	Feb 1, 2022
Grant date	Feb 1, 2022

Abstract

The present invention is directed to reaction mixtures comprising a water-surfactant mixture, wherein the catalyst comprises a compound with solubilizing groups. This technology improves the solubility of the reaction components in the water-surfactant mixture and thereby, greatly increases the productivity and selectivity of the chemical reaction.

First claim

The invention claimed is:

1. A reaction mixture comprising one or more reactants, a catalyst and a surfactant-water mixture, wherein the catalyst is
a coupling reagent, wherein the coupling reagent is a 1,3,5-triazine comprising one or more solubilizing groups;
wherein the solubilizing group comprises a C 5-50 alkyl group or a poly(alkylene glycol) group with 2 to 20 repeating units,
wherein the surfactant-water mixture comprises a surfactant and water, and the surfactant is DL-α-Tocopherol methoxypolyethylene glycol succinate.

2. The reaction mixture according to claim 1 , wherein the solubilizing group comprises a C 5-50 alkyl group and has one or more of the following features:
(i) the C 5-50 alkyl group is linear;
(ii) the C 5-50 alkyl group comprises 8-15 carbon atoms;
(iii) being substituted with one or more groups selected from methoxy, ethoxy, propoxy, hydroxy, amino optionally substituted with one or two of methyl, ethyl and propyl; and
(iv) 12-methoxydodecyl or dodecyl.

3. The reaction mixture according to claim 1 , wherein the solubilizing group comprises a poly(alkylene glycol) group with 2 to 20 repeating units, further wherein the poly(alkylene glycol) group has one or more of the following features:
(i) the poly(alkylene glycol) group is a poly(ethylene glycol) group or poly(propylene glycol) group;
(ii) the poly(alkylene glycol) group has 3 to 8 repeating units;
(iii) being substituted with one or more groups selected from methyl, ethyl, propyl, methoxy, ethoxy, propoxy, hydroxy, and amino optionally substituted with one or two of methyl, ethyl and propyl; and
(iv) a poly(ethylene glycol) group with 4 to 6 repeating units, optionally substituted with methyl or ethyl at a terminal oxygen.

4. The reaction mixture according to claim 3 , wherein the 1,3,5-triazine has one or more of the following features:
(i) comprising a quaternary amino group, wherein the quaternary amino group is attached to a 2-position of a triazine ring;
(ii) being substituted with at least one of methyl, ethyl, propyl, methoxy, ethoxy and propoxy at least one of a 4- and a 6-position of the triazine ring;
(iii) the one or more solubilizing groups being attached to at least one of the quaternary amino group, the 4- and 6-position of the triazine ring.

5. The reaction mixture according to claim 4 , wherein the quaternary amino group is a trimethylamino or an N-methyl-N-morpholino group.

6. The reaction mixture according to claim 1 , wherein the solubilizing group is attached to a remaining part of the coupling reagent or ligand via an ether, amine, ester or amide bond.

7. The reaction mixture according to claim 1 , wherein the coupling reagent or ligand comprises one or two solubilizing groups.

8. The reaction mixture according to claim 1 , wherein the concentration of the surfactant in the surfactant-water mixture is 0.5 to 5% (w/w).

9. The reaction mixture according to claim 1 , wherein the reaction mixture comprising one reactant or two reactants.

10. The reaction mixture according to claim 1 , further comprising an organic solvent.

11. The reaction mixture according to claim 1 , wherein the reaction mixture is a homogeneous mixture.

12. The reaction mixture according to claim 1 , wherein the reaction mixture is a colloidal suspension.

13. A method of performing a chemical reaction, comprising the steps of
(a) providing a reaction mixture according to claim 1 , and
(b) allowing the chemical reaction to proceed.

14. The method according to claim 13 , further comprising the step of isolating the product of the chemical reaction.

15. The method according to claim 13 , wherein the reaction mixture is a homogeneous mixture throughout the entire chemical reaction.

16. The method according to claim 13 , wherein the reaction mixture is a colloidal suspension throughout the entire chemical reaction.

17. A method of increasing a yield of a chemical reaction performed in a surfactant-water mixture, comprising the steps of
(a) providing a reaction mixture comprising one or more reactants, a catalyst, and a surfactant-water mixture, wherein the catalyst is
a coupling reagent, wherein the coupling reagent is a 1,3,5-triazine comprising one or more solubilizing groups,
wherein the solubilizing group comprises a C 5-50 alkyl group or a poly(alkylene glycol) group with 2 to 20 repeating units,
wherein the surfactant-water mixture comprises a surfactant and water, and the surfactant is DL-α-Tocopherol methoxypolyethylene glycol succinate; and

(b) allowing the chemical reaction to proceed.

18. A method of decreasing an amount of side products produced in a chemical reaction performed in a surfactant-water mixture, comprising the steps of
(a) providing a reaction mixture comprising one or more reactants, a catalyst, and a surfactant-water mixture, wherein the catalyst is
a coupling reagent, wherein the coupling reagent is a 1,3,5-triazine comprising one or more solubilizing groups;
wherein the solubilizing group comprises a C 5-50 alkyl group or a poly(alkylene glycol) group with 2 to 20 repeating units,
wherein the surfactant-water mixture comprises a surfactant and water, and the surfactant is DL-α-Tocopherol methoxypolyethylene glycol succinate; and
(b) allowing the chemical reaction to proceed.

Assignees

• Novartis Ag

Inventors

• Gallou Fabrice
• Guo Pengfei
• Zhou Jianguang
• Parmentier Michael

Classifications

• B01J31/2438

  and further hetero atoms as ring members, excluding the positions adjacent to P · CPC title

• B01J31/0215 Primary

  Sulfur-containing compounds · CPC title

• B01J2531/985

  in a water / organic solvent system · CPC title

• B01J2231/40

  Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions · CPC title

• B01J31/0271

  also containing elements or functional groups covered by B01J31/0201 - B01J31/0231 · CPC title