Method for producing unsaturated organics from organic-containing feeds

• US 5,543,558 A
• Filed: 12/23/1993
• Issued: 08/06/1996
• Est. Priority Date: 12/23/1993
• Status: Expired due to Fees

• Current Assignee: Quantum Catalytics LLC
• Original Assignee: Molten Metal Technology Incorporated
• Inventors: Nagel, Christopher J., Bach, Robert D.
• Primary Examiner(s): Killos, Paul J.
• Application Number:
  US08/173,362
• Time in Patent Office: 957 Days
• Field of Search: 560/211, 560/214
• US Class Current: 560/214
• CPC Class Codes: C07B 61/00 Other general methods
• CPC Class Codes: C07C 11/04 Ethylene
• CPC Class Codes: C07C 4/10 from acyclic hydrocarbons
• CPC Class Codes: C07C 67/333 by isomerisation; by change of size of the carbon skeleton introduction or elimination of carboxyl groups C07C67/313, C07C67/32
• CPC Class Codes: C07C 69/54 Acrylic acid esters; Methacrylic acid esters

Abstract

A method includes producing an unsaturated organic compound from an organic component of an organic-containing feed. A reactor is provided which contains a molten metal bath. The molten metal bath includes a metal, such as a suitable transition metal, which can interact with an organic component of the feed. The feed is directed into the molten metal bath at a rate which causes the metal to interact with the organic component. Operating conditions are established and maintained in the reactor to cause the metal to interact with the organic component. At least one carbon-carbon double bond is formed in the organic component to produce an unsaturated organic compound that is discharged from the molten metal bath.

Claims

1. A method for producing an alkene compound from an alkane component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including an elemental metal which can interact with an alkane component of the feed;

b) directing said feed into the molten metal bath at a rate which causes the elemental metal to interact with said alkane component; and

c) establishing and maintaining operating conditions in said reactor to cause said elemental metal to interact with the alkane component, whereby at least one carbon-carbon double bond is formed in the alkane component to produce an alkene compound.

2. A method of claim 1 wherein the metal includes a transition metal.

3. A method of claim 2 wherein the reactor which is provided contains a molten metal bath including a transition metal that has an energy gap between its ground and first excited electronic states that is less than about 1.5 eV.

4. A method of claim 1 wherein the metal bath provided includes more than one metal.

5. A method of claim 4 wherein at least two of the metals of the molten metal bath provided include transition metals that have energy gaps between their ground and first excited electronic states of less than about 1.5 eV.

6. A method of claim 3 wherein the operating conditions established and maintained in the reactor include a temperature of the molten metal bath which is less than about 1,000°

C.

7. A method of claim 3 wherein the operating conditions established and maintained in the reactor include a temperature of the molten metal bath which is less than about 2,000°

C.

8. A method of claim 7 wherein the alkane component includes an aryl substituent.

9. A method of claim 8 wherein the alkane component includes butane, whereby the alkene compound that is discharged from the molten metal bath includes ethylene.

10. A method of claim 9 wherein the organic feed includes at least two alkane components.

11. A method of claim 10 wherein the operating conditions of said reactor include a concentration of dissolved carbon in the molten metal bath to be less than that of saturation.

12. A method of claim 1 wherein the feed further includes polymethyl methacrylate and wherein methyl methacrylate is formed.

13. A method of claim 1 wherein the feed includes at least one hydrogen-containing component.

14. A method of claim 1 wherein the metal is a component of the organic feed.

15. A method of claim 14 wherein the metal component is in an oxidized state.

16. A method of claim 14 wherein the metal component is in an anionic state.

17. A method of claim 1 wherein the molten metal bath provided includes at least two metals which can insert into the organic component of the feed.

18. A method of claim 14 wherein the metal of the molten metal bath is a metal anion formed by reduction of a metal component of the organic feed.

19. A method of claim 18 wherein the metal component of the organic feed is reduced in the molten metal bath by a metal component of said bath.

20. A method of claim 18 wherein the metal component of the organic feed is reduced in the molten metal bath by a carbon component of said bath.

21. A method of claim 1 wherein the metal which can interact with the alkane component of the feed is an alkaline metal.

22. A method of claim 1 wherein the metal which can interact with the alkane component of the feed is an alkaline earth metal.

23. A method of claim 14 wherein the metal of the molten metal bath is a metal cation formed by oxidation of a metal component of the organic feed.

24. A method of claim 23 wherein the metal of the metal component of the organic feed is oxidized in the molten metal bath by a metal component of said bath.

25. A method of claim 23 wherein the metal of the metal component of the organic waste feed is oxidized by halogenation in said bath.

26. A method of claim 25 wherein the metal is a metal ion.

27. A method of claim 26 wherein the metal ion is formed by an induction field.

28. A method of claim 26 wherein the metal ion is formed by a plasma gas.

29. A method for producing ethylene from a polyethylene terephthalate, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including a metal which can interact with polyethylene terephthalate;

b) directing said polyethylene terephthalate into the molten metal bath at a rate which causes the metal to interact with said polyethylene terephthalate; and

c) establishing and maintaining operating conditions in said reactor to cause said metal to interact with at least a portion of the polyethylene terephthalate, whereby at least one carbon-carbon double bond is formed in the polyethylene terephthalate to produce ethylene.

30. A method for producing a methyl methacrylate from polymethyl methacrylate, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including a metal which can interact with the polymethyl methacrylate;

b) directing said polymethyl methacrylate into the molten metal bath at a rate which causes the metal to interact with said polymethyl methacrylate; and

c) establishing and maintaining operating conditions in said reactor to cause said metal to interact with at least a portion of the polymethyl methacrylate, whereby at least one carbon-carbon double bond is formed in the polymethyl methacrylate to produce a methyl methacrylate.

31. A method for producing an alkene compound from an alkane component of an organic-containing feed, comprising the steps of:

a) providing a reactor containing a molten metal bath including an elemental metal having an energy gap between its ground and first excited electronic states that can cause the elemental metal to be inserted into a sigma bond of an alkane component of the organic-containing feed;

b) directing the organic-containing feed into the molten metal bath; and

c) establishing and maintaining operating conditions in said reactor which cause the metal to insert into said sigma bond of said alkane component to form an organometallic intermediate by an oxidative addition reaction, and which cause the metal of the organometallic intermediate to be subsequently eliminated, whereby the organometallic intermediate is reformed to an alkene compound.

32. A method for producing an alkene compound from an alkane component of an organic-containing feed, comprising the steps of:

a) providing a reactor containing a molten metal bath including an elemental metal having an energy gap between its ground and first excited electronic states of less than about 1.5 eV, whereby the metal can be inserted into a sigma bond of an alkane component of the organic-containing feed;

b) directing the organic-containing feed into the molten metal bath; and

c) establishing and maintaining operating conditions in said reactor which cause the metal to insert into said sigma bond of said alkane component to form an organometallic intermediate by an oxidative addition reaction, and which cause a metal-containing organic fragment to be subsequently eliminated from the organometallic intermediate, thereby causing a remaining fragment of the organometallic intermediate to be reformed to an alkene compound.

33. A method of claim 32 wherein the metal is in its oxidized state.

34. A method of claim 32 wherein the metal is a metal ion.

35. A method of claim 34 wherein the metal ion is formed by an induction field.

36. A method of claim 34 wherein the metal ion is formed by a plasma gas.

37. A method of claim 32 wherein the metal is in its anionic state.

38. A method of claim 32 wherein the molten metal bath includes more than one metal having an energy gap of less than about 1.5 eV.

39. A method of claim 32 wherein the metal is a transition metal.

40. A method of claim 32 wherein an anion of the metal is formed through reduction of the metal.

41. A method of claim 32 wherein an anion of the metal is formed through reduction of the metal by a second metal.

42. A method of claim 32 wherein an anion of the metal catalyst is formed through reduction of the metal by carbon.

43. A method of claim 32 wherein an alkaline metal is employed to produce an anion of the metal.

44. A method of claim 32 wherein an alkaline earth metal is employed to produce an anion of the metal.

45. A method of claim 32 wherein a cation of the metal is formed on oxidation of the metal.

46. A method of claim 32 wherein a cation of the metal is formed on oxidation of the metal by a second metal.

47. A method of claim 32 wherein a halide is employed to produce a cation of the metal.

48. A method for producing an unsaturated organic compound from an organic component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten rhodium-containing bath;

b) directing said feed into the molten rhodium-containing bath at a rate which causes the rhodium to interact with said organic component; and

c) establishing and maintaining operating conditions in said reactor to cause said rhodium to interact with the organic component, whereby at least one carbon-carbon double bond is formed in said portion of the organic component to produce an unsaturated organic compound.

49. A method for producing an unsaturated organic compound from an organic component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten copper-containing bath;

b) directing said feed into the molten copper-containing bath at a rate which causes the copper to interact with said organic component; and

c) establishing and maintaining operating conditions in said reactor to cause said copper to interact with the organic component, whereby at least one carbon-carbon double bond is formed in said organic component to produce an unsaturated organic compound.

50. A method for producing an unsaturated organic compound from a polyethylene terephthalate component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including a metal which can interact with a polyethylene terephthalate component of the feed;

b) directing said feed into the molten metal bath at a rate which causes the metal to interact with said polyethylene terephthalate component; and

c) establishing and maintaining operating conditions in said reactor to cause said metal to interact with the organic component, whereby at least one carbon-carbon double bond is formed in said polyethylene terephthalate component to produce ethylene that is discharged from the molten metal bath.

51. A method for producing an unsaturated organic compound from a polyethylene terephthalate component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including a metal which can interact with a polyethylene terephthalate component of the feed;

b) directing said feed into the molten metal bath at a rate which causes the metal to interact with said polyethylene terephthalate component; and

c) establishing and maintaining operating conditions in said reactor to cause said metal to interact with the polyethylene terephthalate component, whereby at least one carbon-carbon double bond is formed in said polyethylene terephthalate component to produce an aromatic compound that is discharged from the molten metal bath.

52. A method for producing an unsaturated organic compound from an organic containing feed, comprising the steps of:

a) providing a reactor containing a molten metal bath including an elemental metal having an energy gap between its ground and first excited electronic states that can cause the elemental metal to be inserted into a sigma bond of an alkane component of the organic containing feed;

b) directing the organic containing feed into the molten metal bath; and

c) establishing and maintaining conditions in said reactor which causes the metal to insert into said sigma bond of said alkane component to form an organometallic intermediate by an oxidative addition reaction, and which causes a metal-containing alkane fragment to be subsequently eliminated from the organometallic intermediate, thereby causing a substantial portion of a remaining alkane fragment of the organometallic intermediate to be reformed to an unsaturated organic compound containing fewer carbon atoms.

53. A method of claim 52 where the metal interaction occurs at a carbon-carbon bond of said alkane component.

54. A method of claim 52 where the metal interaction occurs at a carbon-hydrogen bond of said alkane component.

55. A method for producing an unsaturated organic compound from an organic containing feed, comprising the steps of:

a) providing a reactor containing a molten metal bath including an elemental metal having an energy gap between its ground and first excited electronic states of less than about 1.5 eV, whereby the metal can be inserted into a sigma bond of an alkane component of the organic containing feed;

b) directing the organic containing feed into the molten metal bath; and

c) establishing and maintaining conditions in said reactor which causes the metal to insert into said sigma bond of said alkane component to form an organometallic intermediate by an oxidative addition reaction, and which causes a metal containing alkane fragment to be subsequently eliminated from the organometallic intermediate, thereby causing a substantial portion of a remaining alkane fragment of the organometallic intermediate to be reformed to an unsaturated organic compound containing fewer carbon atoms.

56. A method of claim 55 where the metal interaction occurs at a carbon-carbon bond of said alkane component.

57. A method of claim 55 where the metal interaction occurs at a carbon-hydrogen bond of said alkane component.

58. A method for producing an unsaturated organic compound from a component of a hydrocarbon feed, said component containing only hydrogen and carbon, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including an elemental metal which can interact with an organic component of the feed;

b) directing said feed into the molten metal bath at a rate which causes the elemental metal to interact with said hydrocarbon component; and

c) establishing and maintaining conditions in said reactor to cause said elemental metal to interact with the hydrocarbon component, whereby at least one carbon-carbon double bond is formed in the organic component to produce an unsaturated organic compound.

59. A method of claim 58 where the metal interaction occurs at the carbon-carbon bond.

60. A method of claim 58 where the metal interaction occurs at the carbon-hydrogen bond.

61. A method for producing an unsaturated organic compound from an alkane portion of an organic component contained in an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including an elemental metal which can interact to form an organometallic intermediate within the alkane portion of the organic component contained in said organic feed;

b) directing said feed into the molten metal bath at a rate which causes said interaction; and

c) establishing and maintaining conditions in said reactor to cause elimination of the interacted metal in its oxidized form from the alkane portion of the organic component contained in an organic feed, thereby producing predominately an organic compound containing a carbon-carbon double bond.

62. A method of claim 61 where the metal interaction occurs at a carbon-carbon bond of said alkane portion.

63. A method of claim 61 where the metal interaction occurs at a carbon-hydrogen bond of said alkane portion.

64. A method for producing an unsaturated organic compound from an organic component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten bath that includes a catalytic metal;

b) directing said feed into the molten bath at a rate which causes the catalytic metal to interact with said organic component; and

c) establishing and maintaining operating conditions in said reactor to cause said catalytic metal to interact with the organic component, whereby at least one carbon-carbon double bond is formed in said portion of the organic component to produce an unsaturated organic compound.

65. The method of claim 64, wherein said catalytic metal of the molten bath that is provided is rhodium.

66. The method of claim 64, wherein said catalytic metal of the molten bath that is provided is copper.

67. A method for producing an unsaturated organic compound from an organic component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath that includes an elemental metal component;

b) directing said feed into the molten metal bath at a rate which causes the elemental metal to interact with said organic component; and

c) establishing and maintaining operating conditions in said reactor to cause said elemental metal to interact with the organic component, whereby at least one carbon-carbon double bond is formed in said portion of the organic component to produce an unsaturated organic compound.

68. The method of claim 67, wherein the elemental metal is selected from the group consisting of elements having an atomic number of 39 through 46.

69. The method of claim 67, wherein the elemental metal is selected from the group consisting of elements having an atomic number of 21 through 29.

70. The method of claim 67, wherein the elemental metal is selected from the group consisting of elements in Group VIII of the Periodic Table of the Elements.

71. A method for producing ethylene from a polyethylene component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including a metal which can interact with a polyethylene component of the feed;

b) directing said feed into the molten metal bath at a rate which causes the metal to interact with said polyethylene component; and

c) establishing and maintaining operating conditions in said reactor to cause said metal to interact with the polyethylene component, whereby at least one carbon-carbon double bond is formed in said polyethylene component to produce ethylene.

72. A method for producing an unsaturated organic compound from a plastic component of an organic feed, comprising the steps of:

a) providing a reactor containing a molten metal bath, said molten metal bath including a metal which can interact with a plastic component of the feed;

b) directing said feed into the molten metal bath at a rate which causes the metal to interact with said plastic component; and

c) establishing and maintaining operating conditions in said reactor to cause said metal to interact with the plastic component, whereby at least one carbon-carbon bond is formed in the plastic component to produce an unsaturated organic compound.