OLEFIN CONVERSION PROCESS AND OLEFIN RECOVERY PROCESS

Abstract

The present invention provides a process for converting olefins from a mixture of olefins and non-olefinic organic compounds of comparable boiling point to olefin products with a larger difference in boiling point from the boiling point of the non-olefinic organic compounds. Additional steps may be performed to recover the olefin product including separating the olefin product from the mixture produced in the conversion step.

Description

Claims

1. A process comprising: (a) providing a mixture comprising feed olefins and non-olefinic organic compounds, and(b) converting the feed olefins in the mixture to converted olefins to increase the difference in boiling point of the olefins from the non-olefinic organic compounds.

2. The process of claim 1 wherein the feed olefins are converted into converted olefins for which the difference in boiling point from the boiling point of the non-olefinic organic compounds is larger than the difference in boiling point of the feed olefins from the boiling point of the non-olefinic organic compounds.

3. The process of claim 2 wherein the difference in the boiling points of the feed olefins and the non-olefinic organic compounds is about 10° C. or less.

4. The process of claim 2 wherein the difference in the boiling points of the converted olefins and the non-olefinic organic compounds is more than about 5° C.

5. The process of claim 2 wherein the difference in the boiling points of the converted olefins and the non-olefinic organic compounds is more than about 10° C.

6. The process of claim 2 wherein an additional step c) is performed which comprises separating the converted olefins from the mixture produced in step b).

7. The process of claim 6 wherein the converted olefins comprise lower boiling olefin products and higher boiling olefin products and step c) comprises c) (i) separating the lower boiling olefin products from the mixture produced in step b), andc) (ii) separating the higher boiling olefin products from the remaining material.

8. The process of claim 7 wherein steps b) and c) (i) are carried out together at the same time.

9. The process of claim 2 wherein at least a portion of the converted olefins are separated from the reaction mixture of step b) as they are formed.

10. The process of claim 6 wherein steps b) and c) are carried out in the same reaction vessel.

11. The process of claim 6 wherein all of the steps are carried out in the same reaction vessel.

12. The process of claim 2 wherein the olefins are comprised of internal olefins.

13. The process of claim 12 wherein the internal olefins are comprised of mid-chain internal olefins.

14. The process of claim 2 wherein the mixture of step a) is a single carbon number cut.

15. A process comprising: (a) providing a mixture comprising feed olefins and paraffins, and(b) metathesizing the feed olefins in the mixture to converted olefins to increase the difference in boiling point of the olefins from the paraffins.

16. The process of claim 15 wherein the feed olefins are metathesized into converted olefins which comprise lower boiling olefin products and higher boiling olefin products for which the difference in boiling point from the boiling point of the paraffins is larger than the difference in boiling point of the feed olefins from the boiling point of the paraffins.

17. The process of claim 16 wherein the difference in boiling points of the feed olefins and the paraffins is about 10° C. or less.

18. The process of claim 16 wherein the difference in the boiling points of the converted olefins and the paraffins is more than about 5° C.

19. The process of claim 16 wherein the difference in the boiling points of the converted olefins and the paraffins is more than about 10° C.

20. The process of claim 16 wherein an additional step c) is performed which comprises separating the converted olefins from the mixture produced in step b).

21. The process of claim 20 wherein the converted olefins comprise lower boiling olefin products and higher boiling olefin products and step c) comprises c) (i) separating the lower boiling olefin products from the mixture produced in step b), andc) (ii) separating the higher boiling olefin products from the remaining material.

22. The process of claim 21 wherein steps b) and c) (i) are carried out together at the same time.

23. The process of claim 16 wherein the lower boiling olefin product is removed from the reaction mixture of step b) as it is formed.

24. The process of claim 16 wherein steps b) and c) are carried out in the same reaction vessel.

25. The process of claim 16 wherein all of the steps are carried out in the same reaction vessel.

26. The process of claim 16 wherein the olefins are comprised of internal olefins.

27. The process of claim 26 wherein the internal olefins are comprised of mid-chain internal olefins.

28. The process of claim 16 wherein the metathesis is carried out at a temperature from about −10° C. to about 300° C.

29. The process of claim 16 wherein the metathesis catalyst is a tungsten-based catalyst is used and the temperature is from about 200 to about 300° C.

30. The process of claim 16 wherein the metathesis catalyst is a molybdenum-based catalyst is used and the metathesis is carried out at a temperature from about 100 to about 150° C.

31. The process of claim 16 wherein the metathesis catalyst is a rhenium-based catalyst is used and the metathesis is carried out at a temperature from about 30 to about 60° C.

32. The process of claim 16 wherein the mixture of step a) is a single carbon number cut.

33. The process of claim 16 wherein a metathesis catalyst is used and the metathesis catalyst is comprised of one or more—metals selected from the group consisting of Mo, W, Re, and Ru.

34. The process of claim 23 wherein the metathesis is carried out under non-equilibrium conditions.

35. The process of claim 34 wherein a metathesis catalyst is used and the metathesis catalyst is a non-isomerizing metathesis catalyst.

36. The process of claim 35 wherein the non-isomerizing metathesis catalyst is selected from the group consisting of heterogeneous catalysts in which rhenium, molybdenum or tungsten is deposited on a support of silica, alumina, or alumina phosphate and homogeneous catalysts based on ruthenium.

37. The process of claim 36 wherein the non-isomerizing metathesis catalyst is comprised of rhenium deposited on alumina.

38. The process of claim 35 wherein the non-isomerizing metathesis catalyst is a Grubbs catalyst.

39. The process of claim 35 wherein the metathesis catalyst is comprised of one or more metals selected from the group consisting of Mo, W, Re, and Ru.

40. The process of claim 16 wherein a metathesis catalyst is used and the metathesis catalyst is a non-isomerizing metathesis catalyst.

41. The process of claim 40 wherein the non-isomerizing metathesis catalyst is selected from the group consisting of heterogeneous catalysts in which rhenium, molybdenum or tungsten is deposited on a support of silica, alumina, or alumina phosphate and homogeneous catalysts based on ruthenium.

42. The process of claim 41 wherein the non-isomerizing metathesis catalyst is comprised of rhenium deposited on alumina.

43. The process of claim 40 wherein the non-isomerizing metathesis catalyst is a Grubbs catalyst.

44. The process of claim 16 wherein the feed olefins and paraffins provided in step a) are of the same carbon number.

45. A process for producing derivatives of olefins which comprises: (a) providing a mixture comprising feed olefins and non-olefinic organic compounds,(b) converting the feed olefins in the mixture to converted olefins to increase the difference in boiling point of the olefins from the non-olefinic organic compounds,(c) recovering the olefin products, and(d) either: (i) hydroformylating the olefin products to produce alcohols; or(ii) hydroformylating the olefin products to produce alcohols, and adding an alkylene oxide to the alcohols in the presence of an alkoxylation catalyst to produce alcohol alkoxylates; or(iii) hydroformylating the olefin products to produce alcohols, adding an alkylene oxide to the alcohols in the presence of an alkoxylation catalyst, and sulfonating the alcohol alkoxylates; or(iv) hydroformylating the olefin products to produce alcohols, and sulfonating the alcohols; or(v) contacting the olefin products with aromatic hydrocarbons under alkylating conditions effective to alkylate the aromatic hydrocarbons to produce alkyl aromatic hydrocarbons; or(vi) contacting the olefin products with aromatic hydrocarbons under alkylating conditions effective to alkylate the aromatic hydrocarbons to produce alkyl aromatic hydrocarbons, and sulfonating the alkyl aromatic hydrocarbons to produce alkylarylsulfonates; or(vii) sulfonating the olefin products to produce sulfated olefins; or(viii) hydroformylating the olefin products to produce alcohols, adding an alkylene oxide to the alcohols in the presence of an alkoxylation catalyst to produce alcohol alkoxylates, and combining the alcohol alkoxylates with conventional detergents additives; or(ix) hydroformylating the olefin products to produce alcohols, adding an alkylene oxide to the alcohols in the presence of an alkoxylation catalyst to produce alcohol alkoxylates, sulfonating the alcohol alkoxylates, and combining the sulfonated alcohol alkoxylates with conventional detergents additives; or(x) hydroformylating the olefin products to produce alcohols, sulfonating the alcohols, and combining the sulfonated alcohols with conventional detergents additives; or(xi) contacting the olefin products with aromatic hydrocarbons under alkylating conditions effective to alkylate the aromatic hydrocarbons to produce alkyl aromatic hydrocarbons, sulfonating the alkyl aromatic hydrocarbons to produce alkylarylsulfonates, and combining the alkylarylsulfonates with conventional detergents additives.