CA2633446C - Process for converting carbohydrates to hydrocarbons - Google Patents

Process for converting carbohydrates to hydrocarbons Download PDF

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Publication number
CA2633446C
CA2633446C CA2633446A CA2633446A CA2633446C CA 2633446 C CA2633446 C CA 2633446C CA 2633446 A CA2633446 A CA 2633446A CA 2633446 A CA2633446 A CA 2633446A CA 2633446 C CA2633446 C CA 2633446C
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CA
Canada
Prior art keywords
mixture
carbohydrate
range
zeolite
zsm
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CA2633446A
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French (fr)
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CA2633446A1 (en
Inventor
Jianhua Yao
Edward L. Sughrue
James B. Kimble
Joseph B. Cross
Marvin M. Johnson
Dhananjay B. Ghonasgi
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Phillips 66 Co
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Phillips 66 Co
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Publication date
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Priority to CA2808278A priority Critical patent/CA2808278C/en
Publication of CA2633446A1 publication Critical patent/CA2633446A1/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B30/00—Preparation of starch, degraded or non-chemically modified starch, amylose, or amylopectin
    • C08B30/12—Degraded, destructured or non-chemically modified starch, e.g. mechanically, enzymatically or by irradiation; Bleaching of starch
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/45—Catalytic treatment characterised by the catalyst used containing iron group metals or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/47—Catalytic treatment characterised by the catalyst used containing platinum group metals or compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/42—Catalytic treatment
    • C10G3/44—Catalytic treatment characterised by the catalyst used
    • C10G3/48—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support
    • C10G3/49—Catalytic treatment characterised by the catalyst used further characterised by the catalyst support containing crystalline aluminosilicates, e.g. molecular sieves
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G3/00—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids
    • C10G3/50—Production of liquid hydrocarbon mixtures from oxygen-containing organic materials, e.g. fatty oils, fatty acids in the presence of hydrogen, hydrogen donors or hydrogen generating compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/10—Feedstock materials
    • C10G2300/1011—Biomass
    • C10G2300/1014—Biomass of vegetal origin
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/80—Additives
    • C10G2300/805—Water
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
    • C10G2400/02—Gasoline
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E50/00—Technologies for the production of fuel of non-fossil origin
    • Y02E50/10—Biofuels, e.g. bio-diesel
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P30/00—Technologies relating to oil refining and petrochemical industry
    • Y02P30/20—Technologies relating to oil refining and petrochemical industry using bio-feedstock

Abstract

Processes for the conversion of carbohydrates to gasoline boiling range hydrocarbons, and processes for increasing the solubility of carbohydrates used in such processes are disclosed. The solubility of carbohydrates may be increased by contacting the carbohydrate with an ion-exchange resin. The dissolved product may be hydrogenated and reacted in the present of a catalyst to form a reaction product containing non-aromatic and aromatic gasoline boiling range hydrocarbons.

Claims (58)

The embodiments of the present invention for which an exclusive property or privilege is claimed are defined as follows:
1. A process comprising:
contacting a carbohydrate-containing material with an ion-exchange resin in a liquid medium to form a mixture;
heating the mixture at a temperature sufficient to substantially dissolve the carbohydrate-containing material in the liquid medium; and contacting the mixture with a hydrogenation catalyst under a condition sufficient to form a hydrogenated product.
2. The process of claim 1, wherein said carbohydrate-containing material has an effective hydrogen to carbon ratio of about one or less.
3. The process of claim 1 or claim 2, wherein said carbohydrate-containing material is a polysaccharide.
4. The process of any one of claims 1 to 3, wherein said carbohydrate-containing material is selected from the group consisting of starch, cellulose, glycogen and mixtures thereof.
5. The process of claim 4, wherein said carbohydrate-containing material is starch.
6. The process of any one of claims 1 to 5, wherein said ion-exchange resin comprises a strongly acidic cation-exchange resin.
7. The process of any one of claims 1 to 6, wherein said ion-exchange resin contains sulfonic groups.
8. The process of any one of claims 1 to 7, wherein said ion-exchange resin is present in an amount in the range of from about 0.02 to about 10 weight percent, based on the weight of the mixture.
9. The process of any one of claims 1 to 8, wherein said temperature is in the range of from about 100°C to about 180°C.
10. The process of claim 9, wherein said temperature is in the range of from about 120°C to about 160°C.
11. The process of claim 9, wherein said temperature is in the range of from about 120°C to about 140°C.
12. The process of any one of claims 1 to 8, wherein said contacting comprises loading the mixture into an autoclave, flushing the autoclave with nitrogen, and sealing the autoclave.
13. The process of any one of claims 1 to 8, wherein said heating comprises heating the mixture at a temperature in the range of from about 100°C to about 180°C until the mixture is dissolved.
14. The process of any one of claims 1 to 8, wherein said liquid medium is water.
15. The process of any one of claims 1 to 8, wherein said ion-exchange resin is a polystyrene supported resin containing sulfonic acid groups.
16. The process of any one of claims 1 to 8, wherein between 95% and 100% of said carbohydrate-containing material is dissolved in said liquid medium.
17. A process comprising:
contacting a carbohydrate-containing material with an ion-exchange resin in a liquid medium under a condition sufficient to substantially dissolve the carbohydrate-containing material in the liquid medium to form a mixture, contacting the mixture with a hydrogenation catalyst under a condition sufficient to form a hydrogenated product, and contacting a mixture comprising the hydrogenated product with a catalyst composition comprising a zeolite under a condition sufficient to form a reaction product containing gasoline boiling range hydrocarbons.
18. The process of claim 17, wherein said carbohydrate-containing material has an effective hydrogen to carbon ratio of about one or less.
19. The process of claim 17 or claim 18, wherein said carbohydrate-containing material is a polysaccharide.
20. The process of any one of claims 17 to 19, wherein said carbohydrate-containing material is selected from the group consisting of starch, cellulose, glycogen and mixtures thereof.
21. The process of claim 20, wherein said carbohydrate-containing material is starch.
22. The process of any one of claims 17 to 21, wherein the ion-exchange resin comprises an acidic cation-exchange resin.
23. The process of any one of claims 17 to 22, wherein the ion-exchange resin contains sulfonic groups.
24. The process of any one of claims 17 to 23, wherein said ion-exchange resin is present in an amount in the range of from about 0.02 to about 10 weight percent, based on the weight of the mixture.
25. The process of any one of claims 17 to 24, wherein said condition sufficient to substantially dissolve the carbohydrate-containing material in the liquid medium to form a mixture comprises a temperature in the range of from about 100°C to about 180°C
and a pressure in the range of from about 10 to about 500 psig.
26. The process of any one of claims 17 to 24, wherein said hydrogenation catalyst comprises a supported ruthenium catalyst.
27. The process of any one of claims 17 to 24, wherein said condition sufficient to form a hydrogenated product comprises a temperature in the range of from about 80°C to about 300°C and a pressure in the range of from about 100 to about 2000 psig.
28. The process of any one of claims 17 to 24, wherein said condition sufficient to form a reaction product containing gasoline boiling range hydrocarbons comprises a temperature in the range of about 200°C to about 800°C and a pressure in the range of from about 1 to about 500 psig.
29. The process of any one of claims 17 to 24, wherein said contacting comprises loading the mixture into an autoclave, flushing the autoclave with nitrogen, and sealing the autoclave.
30. The process of any one of claims 17 to 24, wherein said heating comprises heating the mixture at a temperature in the range of from about 100°C to about 180°C until the mixture is dissolved.
31. The process of any one of claims 17 to 24, wherein said liquid medium is water.
32. The process of any one of claims 17 to 24, wherein said ion-exchange resin is a polystyrene supported resin containing sulfonic acid groups.
33. The process of any one of claims 17 to 24, wherein between 95% and 100% of said carbohydrate-containing material is dissolved in said liquid medium.
34. The process of any one of claims 17 to 24, wherein said hydrogenated product is selected from the group consisting of ketones, epoxides, diols, glycols, furans, and organic acids.
35. The process of any one of claims 17 to 24, wherein said hydrogenated product is lactic acid.
36. The process of any one of claims 17 to 24, wherein said hydrogenated product is sorbitol.
37. The process of any one of claims 17 to 24, wherein said mixture further comprises a hydrocarbon.
38. The process of claim 37, wherein said hydrocarbon is isopentane.
39. The process in accordance with any one of claims 17 to 24, wherein said zeolite is selected from the group consisting of ZSM-5, ZSM-8, ZSM-11, ZSM-12, ZSM-35, ZSM-38 and combinations thereof.
40. The process in accordance with any one of claims 17 to 24, wherein said zeolite is ZSM-5.
41. The process in accordance with any one of claims 17 to 24, further comprising a step of modifying a zeolite by steam treatment prior to the step of contacting a mixture comprising the hydrogenated product with a catalyst composition comprising the steam treated zeolite.
42. The process in accordance with any one of claims 17 to 24, further comprising a step of modifying a zeolite by acid treatment prior to the step of contacting a mixture comprising the hydrogenated product with a catalyst composition comprising the acid treated zeolite.
43. The process in accordance with any one of claims 17 to 24, further comprising a step of modifying a zeolite with a metal cation prior to the step of contacting a mixture comprising the hydrogenated product with a catalyst composition comprising the metal cation treated zeolite.
44. The process in accordance with claim 43 wherein said metal cation is selected from the group consisting of zinc, gallium, and nickel.
45. A process in accordance with claim 1 further comprising the step:
contacting the hydrogenated product with a catalyst composition comprising a zeolite under reaction conditions sufficient to form a reaction product containing gasoline boiling range hydrocarbons.
46. The process of claim 45, wherein the hydrogenated carbohydrate-containing compound is sorbitol.
47. The process of claim 45, wherein said hydrogenated carbohydrate-containing compound is lactic acid.
48. The process of any one of claims 45 to 47, wherein said hydrocarbon comprises isopentane.
49. The process of claim 45, wherein said hydrogenated carbohydrate-containing compound is selected from the group consisting of ketones, epoxides, diols, glycols, furans, and organic acids.
50. A renewable hydrocarbon fuel produced by the process of any one of claims 45 to 49.
51. The process of any one of claims 45 to 49, wherein the reaction conditions sufficient to form a reaction product containing gasoline boiling range hydrocarbons comprises a temperature in the range of about 200°C to about 600°C and a pressure in the range of from about 1 to about 100 psig.
52. The process of any one of claims 45 to 49, wherein the reaction conditions comprise a pressure in the range of from about 20 to about 200 psig.
53. The process in accordance with of any one of claims 45 to 49, wherein said zeolite is selected from the group consisting of ZSM-5, ZSM-8, ZSM-11, ZSM-12, ZSM-35, ZSM-38 and combinations thereof.
54. The process in accordance with of any one of claims 45 to 49, wherein said zeolite is ZSM-5.
55. The process in accordance with of any one of claims 45 to 49, further comprising a step of modifying a zeolite by steam treatment prior to the step of contacting a mixture comprising a hydrogenated carbohydrate-containing compound and a hydrocarbon with a catalyst composition comprising the steam treated zeolite.
56. The process in accordance with of any one of claims 45 to 49, further comprising a step of modifying a zeolite by acid treatment prior to the step of contacting a mixture comprising a hydrogenated carbohydrate-containing compound and a hydrocarbon with a catalyst composition comprising the acid treated zeolite.
57. The process in accordance with of any one of claims 45 to 49, further comprising a step of modifying a zeolite with a metal cation prior to the step of contacting a mixture comprising a hydrogenated carbohydrate-containing compound and a hydrocarbon with a catalyst composition comprising the metal cation treated zeolite.
58. The process in accordance with claim 57, wherein said metal cation is selected from the group consisting of zinc, gallium, and nickel.
CA2633446A 2005-12-16 2006-12-14 Process for converting carbohydrates to hydrocarbons Active CA2633446C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2808278A CA2808278C (en) 2005-12-16 2006-12-14 Process for converting carbohydrates to hydrocarbons

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US11/303,636 2005-12-16
US11/303,636 US7678950B2 (en) 2005-12-16 2005-12-16 Process for converting carbohydrates to hydrocarbons
PCT/US2006/047807 WO2007075370A2 (en) 2005-12-16 2006-12-14 Process for converting carbohydrates to hydrocarbons

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CA2633446A1 CA2633446A1 (en) 2007-07-05
CA2633446C true CA2633446C (en) 2014-10-14

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US (1) US7678950B2 (en)
EP (1) EP1968917A4 (en)
BR (1) BRPI0619976A2 (en)
CA (2) CA2633446C (en)
WO (1) WO2007075370A2 (en)

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CA2808278A1 (en) 2007-07-05
US20070142633A1 (en) 2007-06-21
US7678950B2 (en) 2010-03-16
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CA2633446A1 (en) 2007-07-05
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