Method of producing imines
A method for forming an imine comprises reacting a first reactant comprising a hydroxyl functionality, a carbonyl functionality, or both a hydroxyl functionality and a carbonyl functionality with a second reactant having an amine functionality in the presence of ordered porous manganese-based octahedral molecular sieves and an oxygen containing gas at a temperature and for a time sufficient for the imine to be produced.
1. A method for forming an imine comprising:
reacting a first reactant comprising a hydroxyl functionality, a carbonyl functionality, or both a hydroxyl functionality and a carbonyl functionality with a second reactant having an amine functionality in the presence of ordered porous manganese-based octahedral molecular sieves and an oxygen containing gas at a temperature and for a time sufficient for the imine to be produced, wherein the ordered porous manganese-based octahedral molecular sieves are present in a catalytic amount.
2. The method of claim 1 wherein the ordered porous manganese-based octahedral molecular sieves comprise todorkites.
3. The method of claim 1 wherein the ordered porous manganese-based octahedral molecular sieves comprise hollandites.
4. The method of claim 1 wherein the ordered porous manganese-based octahedral molecular sieves have an average manganese oxidation state of about 3 to about 4.
5. The method of claim 1 wherein the hydroxyl functionality is a primary hydroxyl functionality.
6. The method of claim 1 wherein the molar ratio of ordered porous manganese-based octahedral molecular sieves to the first reactant is about 0.0625 to about 0.5.
7. The method of claim 1 wherein the amine functionality is a primary amine functionality.
8. The method of claim 1 wherein the first reactant, the second reactant or both the first reactant and the second reactant are dissolved in a solvent.
9. The method of claim 8 wherein the solvent is a non-polar aprotic solvent.
10. The method of claim 1 wherein the first reactant comprises a hydroxyl functionality and a carbonyl functionality and the temperature of the method is chosen to selectively react the carbonyl functionality with the second reactant.
11. The method of claim 1 wherein the oxygen containing gas is air.
12. The method of claim 1 wherein the ordered porous manganese-based octahedral molecular sieves have been recycled.
13. The method of claim 1 wherein the oxygen containing gas is flowing.
14. The method of claim 1 wherein the ordered porous manganese-based octahedral molecular sieves further comprise an additional transition metal.
15. A method for forming an imine comprising:
reacting a first reactant comprising a primary hydroxyl functionality, a carbonyl functionality, or both a primary hydroxyl functionality and a carbonyl functionality with a second reactant having a primary amine functionality in the presence of ordered porous manganese-based octahedral molecular sieves and an oxygen containing gas at a temperature and for a time sufficient for the imine to be produced, wherein the ordered porous manganese-based octahedral molecular sieves are present in a catalytic amount.