Acid-catalyzed olefin oligomerizations

1. A process comprising:

(i) contacting a monomer comprising at least 50 wt. % linear internal olefins with a solid acid catalyst comprising a sulfonated styrene-divinylbenzene copolymer acid resin; and

(ii) oligomerizing the monomer to form an oligomer product.

2. The process of claim 1 , wherein the monomer comprises at least 75 wt. % C 8 to C 24 linear internal olefins and less than 15 wt. % C 8 to C 24 alpha olefins.

3. The process of claim 1 , wherein the monomer comprises at least 95 wt. % C 8 to C 20 linear internal olefins and less than 5 wt. % C 8 to C 20 alpha olefins.

4. The process of claim 1 , wherein the monomer comprises C 8 linear internal olefins, C 10 linear internal olefins, C 12 linear internal olefins, C 14 linear internal olefins, C 16 linear internal olefins, or any combination thereof.

5. The process of claim 1 , wherein:

a) the monomer is substantially free of oxygen-containing compounds;

b) the monomer is substantially free of nitrogen-containing compounds; or

c) the monomer is substantially free of oxygen-containing compounds and nitrogen-containing compounds.

6. The process of claim 1 , wherein:

a) a single pass conversion of the monomer to the oligomer product is at least 10 wt. %;

b) a single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period of at least 5 days; or

c) the single pass conversion of the monomer to the oligomer product is at least 10 wt. % and the single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period of at least 5 days.

7. The process of claim 1 , wherein:

a) a single pass conversion of the monomer to the oligomer product is at least 15 wt. %;

b) a single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period of at least 14 days; or

c) the single pass conversion of the monomer to the oligomer product is at least 15 wt. % and the single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period of at least 14 days.

8. The process of claim 1 , wherein:

a) the oligomer product comprises at least 50 wt. % dimers;

b) a weight ratio of dimers to trimers and higher oligomers in the oligomer product is greater than 4:1; or

c) the oligomer product comprises at least 50 wt. % dimers and the weight ratio of dimers to trimers and higher oligomers in the oligomer product is greater than 4:1.

9. The process of claim 1 , wherein:

a) the monomer and the solid acid catalyst are contacted at a WHSV in a range from 0.05 to 5;

b) the oligomerizing step is conducted at a temperature below a maximum operating temperature of the solid acid catalyst; or

c) the monomer and the solid acid catalyst are contacted at a WHSV in a range from 0.05 to 5 and the oligomerizing step is conducted at a temperature below a maximum operating temperature of the solid acid catalyst.

10. The process of claim 1 , further comprising a step of isomerizing an olefin feed to form the monomer.

11. The process of claim 1 , further comprising a step of isolating the oligomer product.

12. A process comprising:

(a) isomerizing an olefin feed comprising linear olefins to produce a linear internal olefin composition comprising linear internal olefins;

(b) contacting the linear internal olefin composition comprising linear internal olefins with a solid acid catalyst comprising a sulfonated styrene-divinylbenzene copolymer acid resin; and

(c) oligomerizing the linear internal olefin composition comprising linear internal olefins to form an oligomer product;

wherein the linear olefins of the olefin feed comprise at least 50 wt. % C 6 to C 24 normal alpha olefins, and linear olefins of the linear internal olefin composition comprise at least 50 wt. % C 6 to C 24 hydrocarbon linear internal olefins.

13. The process of claim 12 , wherein:

the linear olefins of the olefin feed comprise at least 75 wt. % C 6 to C 24 normal alpha olefins; and

the linear olefins of the linear internal olefin composition comprise less than 10 wt. % C 6 to C 24 normal alpha olefins.

14. The process of claim 12 , wherein:

the linear olefins of the olefin feed comprise at least 90 wt. % C 6 to C 24 normal alpha olefins; and

the linear olefins of the linear internal olefin composition comprise less than 2 wt. % C 6 to C 24 normal alpha olefins.

15. The process of claim 12 , wherein:

a single pass conversion of the linear internal olefin composition to the oligomer product is at least 10 wt. % and the single pass conversion of the linear internal olefin composition to the oligomer product is maintained substantially constant for a time period in a range from 5 to 60 days; or

a single pass conversion of the linear internal olefin composition to the oligomer product is at least 15 wt. % and the single pass conversion of the linear internal olefin composition to the oligomer product is maintained substantially constant for a time period in a range from 10 to 45 days.

16. A process comprising:

(i) contacting a monomer comprising at least 50 wt. % C 8 to C 12 linear internal olefins with a solid acid catalyst comprising a sulfonated styrene-divinylbenzene copolymer acid resin; and

(ii) oligomerizing the monomer to form an oligomer product.

17. The process of claim 16 , wherein the monomer comprises at least 75 wt. % C 8 to C 12 linear internal olefins and less than 15 wt. % C 8 to C 12 alpha olefins.

18. The process of claim 17 , wherein:

a single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period in a range from 5 to 60 days; or

a single pass conversion of the monomer to the oligomer product is at least 10 wt. % and the single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period in a range from 5 to 60 days.

19. The process of claim 17 , wherein:

a single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period in a range from 10 to 45 days; or

a single pass conversion of the monomer to the oligomer product is at least 15 wt. % and the single pass conversion of the monomer to the oligomer product is maintained substantially constant for a time period in a range from 10 to 45 days.

20. The process of claim 17 , wherein the monomer comprises at least 95 wt. % C 8 to C 12 linear internal olefins and less than 5 wt. % C 8 to C 12 alpha olefins.

21. The process of claim 17 , wherein the oligomer product comprises at least 50 wt. % dimers, and a weight ratio of dimers to trimers and higher oligomers in the oligomer product is greater than 4:1.

22. A process comprising:

(a) isomerizing an olefin feed comprising linear olefins to produce a linear internal olefin composition comprising linear internal olefins;

(b) contacting the linear internal olefin composition comprising linear internal olefins with a solid acid catalyst comprising a sulfonated styrene-divinylbenzene copolymer acid resin; and

(c) oligomerizing the linear internal olefin composition comprising linear internal olefins to form an oligomer product;

wherein the linear olefins of the olefin feed comprise at least 50 wt. % C 8 to C 12 normal alpha olefins, and linear olefins of the linear internal olefin composition comprise at least 50 wt. % C 8 to C 12 hydrocarbon linear internal olefins.

23. The process of claim 22 , wherein:

the linear internal olefin composition comprises at least 75 wt. % C 8 to C 12 hydrocarbon linear internal olefins and less than 15 wt. % C 8 to C 12 alpha olefins.

24. The process of claim 22 , wherein:

a single pass conversion of the linear internal olefin composition to the oligomer product is at least 10 wt. % and the single pass conversion of the linear internal olefin composition to the oligomer product is maintained substantially constant for a time period in a range from 5 to 60 days.