Alkylation processes using liquid Lewis acid catalysts
An alkylation process is described. The alkylation process includes contacting a feed comprising a paraffin or an aromatic with an olefin feed in the presence of a liquid Lewis acid catalyst in an alkylation reaction zone under alkylation conditions to form a reaction mixture comprising alkylation products and the liquid Lewis acid catalyst. The liquid Lewis acid catalyst is the liquid reaction product of a donor molecule and a metal halide. The alkylation products are separated from the liquid Lewis acid catalyst and recovered.
1. An alkylation process comprising:
contacting a hydrocarbon feed comprising a butane with an olefin feed comprising a butene in the presence of a liquid Lewis acid catalyst and in the absence of hydrofluoric acid in an alkylation reaction zone under alkylation conditions to form a biphasic reaction mixture comprising alkylation products comprising trimethylpentanes and the liquid Lewis acid catalyst, wherein the liquid Lewis acid catalyst is a liquid reaction product of a donor molecule and a metal halide, wherein the metal in the metal halide is Al, wherein the donor molecule comprises caprolactam, N-methylcaprolactam, delta-valerolactone, tetrahydrofuran, caprolactone, alpha-acetolactone, beta-propiolactone, gamma-butyrolactone, morpholine, beta-propiolactam, gamma-butyrolactam, delta-valerolactam, or combinations thereof, wherein a mole fraction of the metal halide in the liquid Lewis acid is greater than about 0.5 to less than about 1;
separating the biphasic reaction mixture into the alkylation products and the liquid Lewis acid catalyst; and
recovering the alkylation products.
2. The process of claim 1 wherein the halide in the metal halide comprises Br, Cl, I, F, or combinations thereof.
3. The process of claim 1 wherein the metal halide comprises AlCl 3 , AlCl 2 Br, AlBr 3 , or combinations thereof.
4. The process of claim 1 wherein the donor molecule comprises caprolactam, N-methylcaprolactam, delta-valerolactone, tetrahydrofuran, caprolactone, alpha-acetolactone, beta-propiolactone, gamma-butyrolactone, morpholine, beta-propiolactam, gamma-butyrolactam, delta-valerolactam, or combinations thereof.
5. The process of claim 1 further comprising adding a metal, an acid, or an acid precursor to the alkylation reaction zone.
6. The process of claim 1 further comprising recovering the liquid Lewis acid catalyst.
7. The process of claim 1 further comprising recycling the liquid Lewis acid catalyst to the alkylation reaction zone.
8. The process of claim 1 further comprising regenerating the liquid Lewis acid catalyst.
9. The process of claim 1 wherein the alkylation conditions include a temperature of from about 0° C. to about 100° C., a pressure from about 0.3 MPa(g) to about 2.5 MPa(g), a hydrocarbon to olefin molar ratio from about 2:1 to about 20:1, and a residence time of about 1 min to about 1 hour.
10. The process of claim 1 wherein the liquid Lewis acid catalyst is present in an amount between about 1 vol % and about 75 vol % of a total volume of material in the alkylation reaction zone.
11. An alkylation process comprising:
contacting a hydrocarbon feed with an olefin feed in the presence of a liquid Lewis acid catalyst and in the absence of hydrofluoric acid in an alkylation reaction zone under alkylation conditions to form a biphasic reaction mixture comprising alkylation products and the liquid Lewis acid catalyst, wherein the liquid Lewis acid catalyst is a liquid reaction product of a donor molecule and a metal halide, wherein the donor molecule comprises caprolactam, N-methylcaprolactam, delta-valerolactone, tetrahydrofuran, caprolactone, alpha-acetolactone, beta-propiolactone, gamma-butyrolactone, morpholine, beta-propiolactam, gamma-butyrolactam, delta-valerolactam, or combinations thereof, and wherein the hydrocarbon feed comprises a paraffin having 3 to 8 carbon atoms and wherein the olefin feed has 2 to 8 carbon atoms;
separating the biphasic reaction mixture into the alkylation products and the liquid Lewis acid catalyst;
recovering the alkylation products; and
recovering the liquid Lewis acid catalyst.
12. The process of claim 11 wherein the metal in the metal halide comprises Sn, Al, Zn, Mn, Fe, Ga, Cu, Ni, Co, In, or combinations thereof, and wherein the halide comprises Br, Cl, I, F, or combinations thereof.
13. The process of claim 11 wherein the metal halide comprises AlCl 3 , AlCl 2 Br, AlBr 3 , GaCl 3 , GaCl 2 Br, FeCl 3 , GaBr 3 , InCl 3 , InBr 3 , InCl 2 Br, or combinations thereof.
14. The process of claim 11 wherein a mole fraction of metal halide in the liquid Lewis acid is greater than about 0.5 to less than about 1.
15. The process of claim 11 further comprising adding a metal, an acid, or an acid precursor to the alkylation reaction zone.
16. The process of claim 11 further comprising at least one of:
recycling the liquid Lewis acid catalyst to the alkylation reaction zone; and
regenerating the liquid Lewis acid catalyst.
17. The process of claim 11 wherein the alkylation conditions include a temperature of from about 0° C. to about 100° C., a pressure from about 0.3 MPa(g) to about 2.5 MPa(g), an isobutane to olefin molar ratio from about 2:1 to about 20:1, and a residence time of about 1 min to about 1 hour; and wherein liquid Lewis acid catalyst is present in an amount between about 1 vol % and about 75 vol % of the total volume of material in the alkylation reaction zone.
18. An alkylation process comprising:
contacting a hydrocarbon feed comprising a paraffin or an aromatic with an olefin feed in the presence of a liquid Lewis acid catalyst in an alkylation reaction zone under alkylation conditions to form a biphasic reaction mixture comprising alkylation products and the liquid Lewis acid catalyst, wherein the liquid Lewis acid catalyst is a liquid reaction product of a donor molecule and a metal halide, wherein the metal in the metal halide is Al, wherein the donor molecule is a Lewis base capable of donating electrons to the metal, wherein the donor molecule comprises caprolactam, N-methylcaprolactam, delta-valerolactone, tetrahydrofuran, caprolactone, alpha-acetolactone, beta-propiolactone, gamma-butyrolactone, morpholine, beta-propiolactam, gamma-butyrolactam, delta-valerolactam, or combinations thereof, wherein a mole fraction of the metal halide in the liquid Lewis acid is greater than about 0.5 to less than about 1;
separating the biphasic reaction mixture into the alkylation products and the liquid Lewis acid catalyst; and
recovering the alkylation products.
19. The process of claim 18 wherein the donor molecule comprises caprolactam, N-methylcaprolactam, delta-valerolactone, tetrahydrofuran, caprolactone, alpha-acetolactone, beta-propiolactone, gamma-butyrolactone, morpholine, beta-propiolactam, gamma-butyrolactam, delta-valerolactam, or combinations thereof.