Selective catalytic production of linear alpha olefins from lactones and unsaturated carboxylic acids
Described is a method to make linear alpha olefins. The method includes the steps of contacting a feedstock having a lactone and/or an unsaturated carboxylic acid with a solid acid catalyst having acidic catalytic sites including Lewis acid catalytic sites, for a time and a temperature wherein at least a fraction of the lactone and/or unsaturated carboxylic acid present in the feedstock is converted into a linear alpha olefin. The method may optionally take place in the presence of water. The solid acid catalyst should preferably have at least 50% Lewis acid catalytic sites.
1. A method to make linear alpha olefins comprising:
a) contacting in a reactor a feedstock comprising a component selected from the group consisting of at least one lactone, at least one unsaturated carboxylic acid, at least one hydroxy carboxylic acid, and a combination thereof, with a solid acid catalyst having acidic catalytic sites, wherein the acidic catalytic sites include Lewis acid catalytic sites, for a time and a temperature wherein at least a fraction of the component is converted into linear alpha olefins; and
b) removing the linear alpha olefins from the solid acid catalyst by flowing an inert gas through the reactor, thereby minimizing isomerization of the linear alpha olefins to internal olefins;
wherein the solid acid catalyst is selected from the croup consisting of γ-Al 2 O 3 , ≤8 wt % WO x supported on γ-Al 2 O 3 and MgO; and
wherein the linear alpha olefins comprise at least 71.0 mol % of all olefins formed in the method.
2. The method of claim 1 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
3. The method of claim 2 , wherein the co-solvent is water.
4. The method of claim 1 , wherein at least 50% of the acidic catalytic sites on the solid acid catalyst are Lewis acid catalytic sites.
5. The method of claim 4 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
6. The method of claim 5 , wherein the co-solvent is water.
7. The method of claim 1 , wherein at least 60% of the acidic catalytic sites on the solid acid catalyst are Lewis acid catalytic sites.
8. The method of claim 7 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
9. The method of claim 8 , wherein the co-solvent is water.
10. The method of claim 1 , wherein at least 70% of the acidic catalytic sites on the solid acid catalyst are Lewis acid catalytic sites.
11. The method of claim 10 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
12. The method of claim 11 , wherein the co-solvent is water.
13. The method of claim 1 , wherein at least 80% of the acidic catalytic sites on the solid acid catalyst are Lewis acid catalytic sites.
14. The method of claim 13 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
15. The method of claim 14 , wherein the co-solvent is water.
16. The method of claim 1 , wherein at least 90% of the acidic catalytic sites on the solid acid catalyst are Lewis acid catalytic sites.
17. The method of claim 16 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
18. The method of claim 17 , wherein the co-solvent is water.
19. The method of claim 1 , comprising contacting the feedstock with the solid acid catalyst at a temperature of from 500 K to 1000 K.
20. The method of claim 19 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
21. The method of claim 20 , wherein the co-solvent is water.
22. The method of claim 1 , comprising contacting the feedstock with the solid acid catalyst at a temperature of from 600 K to 900 K.
23. The method of claim 22 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
24. The method of claim 23 , wherein the co-solvent is water.
25. The method of claim 1 , comprising contacting the feedstock with the solid acid catalyst at a temperature of from 625 K to 850 K.
26. The method of claim 25 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
27. The method of claim 26 , wherein the co-solvent is water.
28. The method of claim 1 , comprising contacting the feedstock with the solid acid catalyst at a temperature of from 650 K to 800 K.
29. The method of claim 28 , further comprising contacting the feedstock with the solid acid catalyst in the presence of a co-solvent.
30. The method of claim 29 , wherein the co-solvent is water.
31. The method of claim 1 , wherein the solid acid catalyst is γ-Al 2 O 3 .
32. The method of claim 1 , wherein the linear alpha olefins comprise at least 82.4 mol % of all olefins formed in the method.
33. The method of claim 1 , wherein the linear alpha olefins comprise at least 92.2 mol % of all olefins formed in the method.
34. The method of claim 1 , wherein the linear alpha olefins comprise at least 97.0 mol % of all olefins formed in the method.