Processes for producing beta-lactone and beta-lactone derivatives with heterogenous catalysts
The present invention is directed to processes from producing beta-lactone and beta-lactone derivatives using heterogenous catalysts. In preferred embodiments of the present invention, the processes comprise the steps: passing a feed stream comprising an epoxide reagent and a carbon monoxide reagent to a reaction zone; contacting the epoxide reagent and the carbon monoxide reagent with a heterogenous catalyst to produce a beta-lactone product in the reaction zone; and removing the beta-lactone product from the reaction zone. In preferred embodiments, the heterogenous catalyst comprises a solid support containing a cationic Lewis acid functional group and a metal carbonyl compound comprising at least one of anionic metal carbonyl compound or a neutral metal carbonyl compound. In certain preferred embodiments, the epoxide reagent and carbon monoxide reagent have a biobased content.
1. A heterogeneous catalyst useful for producing beta-lactone from an epoxide reagent, a carbon monoxide reagent, and mixtures thereof in a carbonylation process, said heterogeneous catalyst comprising a solid component comprising a catalytically effective amount of cationic Lewis acid functional group and anionic metal carbonyl compound associated with a solid support and wherein the cationic Lewis acid functional group is anchored or covalently bonded to the solid support, wherein the heterogeneous catalyst further comprises from about 0.1 weight percent to about 10 weight percent cationic Lewis acid functional group and anionic metal carbonyl compound.
2. The heterogeneous catalyst of claim 1 , wherein the heterogeneous catalyst further comprises from about 0.1 weight percent to about 2 weight percent each of cationic Lewis acid functional group and anionic metal carbonyl compound.
3. The heterogeneous catalyst of claim 1 , wherein the anionic metal carbonyl compound is selected from a group consisting of [Co(CO) 4 ] − , [Ti(CO) 6 ] 2− , [V(CO) 6 ] − , [Rh(CO) 4 ] − , [Fe(CO) 4 ] 2− , [Ru(CO) 4 ] 2− , [Os(CO) 4 ] 2− , [Cr 2 (CO) 10 ] 2− , [Fe 2 (CO) 8 ] 2− , [Tc(CO) 5 ] − , [Re(CO) 5 ] − , and [Mn(CO) 5 ].
4. The heterogeneous catalyst of claim 1 , wherein the catalytically effective amount of cationic Lewis acid functional group comprises at least one Lewis acidic metal complex selected from a group consisting of Zn(II), Cu(II), Mn(II), Co(II), Ru(II), Fe(II), Rh(II), Ni(II), Pd(II), Mg(II), Al(III), Cr(III), Fe(III), Co(III), Ga(III), Mn(III), Ti(IV) and Cr(IV).
5. The heterogeneous catalyst of claim 1 , wherein the solid support is selected from a group consisting of silica, alumina, titania, silica/alumina, pyrogenic silica, high purity silica, zirconia, carbon black, activated carbon, metal halide, zeolite and the combination thereof.
6. The heterogeneous catalyst of claim 5 , wherein the zeolite is selected from a group consisting of a faujasite structure, a mordenite structure, a ZSM-5 (MFI) structure, a hexagonal pore arrangement of MCM-41, a cubic pore arrangement.
7. A process for carbonylation using the heterogeneous catalyst of claim 1 , wherein the process comprises the steps:
passing a feed stream comprising an epoxide reagent and a carbon monoxide reagent to a reaction zone;
contacting the epoxide reagent and the carbon monoxide reagent with the heterogeneous catalyst to produce a beta-lactone product in the reaction zone; and
removing the beta-lactone product from the reaction zone.
8. The process of claim 7 , wherein the step for contacting the epoxide reagent and the carbon monoxide reagent with the heterogeneous catalyst to produce the beta-lactone product in the reaction zone is performed in a vapor phase.
9. The process of claim 7 , wherein the step for contacting the epoxide reagent and the carbon monoxide reagent with the heterogeneous catalyst to produce the beta-lactone product in the reaction zone is performed in a liquid phase using a solvent.
10. The process of claim 9 , wherein the process further comprises a distillation step to separate the beta-lactone product from the solvent.
11. The process of claim 7 , wherein the process further comprises a step of contacting the epoxide reagent and the carbon monoxide reagent with the heterogeneous catalyst to produce a beta-lactone intermediate in the reaction zone.
12. The process of claim 11 , wherein the process further comprises a step of polymerizing the beta-lactone intermediate in the reaction zone to produce a polylactone product.
13. The process of claim 11 , wherein the process further comprises a step of reacting the beta-lactone intermediate with a derivative reagent in the reaction zone to produce a beta-lactone derivative.
14. The process of claim 13 , wherein the derivative reagent is chosen from a list selected from the group consisting of a carbon monoxide reagent, a beta-lactone reagent, an ammonia reagent, and an alcohol reagent.
15. A process for making the heterogeneous catalyst of claim 1 , wherein the process comprises the steps:
impregnating a solid support with a solution comprising a Lewis acid functional group and a metal carbonyl compound in a non-oxygenated hydrocarbon solvent to form an impregnated solid support; and
calcining the impregnated solid support to form the heterogeneous catalyst.
16. The process of claim 15 , wherein the solid support comprises a crystalline structured zeolite.
17. The process of claim 16 , wherein the process further comprises a step of mixing the Lewis acid functional group and the metal carbonyl compound with the crystalline structured zeolite.
18. The process of claim 17 , wherein the process further comprises a step of drying and calcining at 100° C.-400° C.