WO2010098801A1 - Combination of hydrogenation and base catalyzed depolymerization for lignin conversion - Google Patents
Combination of hydrogenation and base catalyzed depolymerization for lignin conversion Download PDFInfo
- Publication number
- WO2010098801A1 WO2010098801A1 PCT/US2009/067422 US2009067422W WO2010098801A1 WO 2010098801 A1 WO2010098801 A1 WO 2010098801A1 US 2009067422 W US2009067422 W US 2009067422W WO 2010098801 A1 WO2010098801 A1 WO 2010098801A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- lignin
- metal
- base
- mixtures
- hydrogenation catalyst
- Prior art date
Links
- 229920005610 lignin Polymers 0.000 title claims abstract description 45
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 title abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 48
- 230000008569 process Effects 0.000 claims abstract description 47
- 239000003054 catalyst Substances 0.000 claims abstract description 21
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 17
- 238000006392 deoxygenation reaction Methods 0.000 claims abstract description 12
- 150000001491 aromatic compounds Chemical class 0.000 claims abstract description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002585 base Substances 0.000 claims description 32
- 239000000203 mixture Substances 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 12
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 9
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 239000011651 chromium Substances 0.000 claims description 6
- 238000005336 cracking Methods 0.000 claims description 6
- 239000013067 intermediate product Substances 0.000 claims description 6
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 claims description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 4
- 239000010953 base metal Substances 0.000 claims description 4
- 229910052976 metal sulfide Inorganic materials 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052804 chromium Inorganic materials 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 229910052759 nickel Inorganic materials 0.000 claims description 3
- 229910000510 noble metal Inorganic materials 0.000 claims description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052721 tungsten Inorganic materials 0.000 claims description 3
- 239000010937 tungsten Substances 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 claims description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052681 coesite Inorganic materials 0.000 claims description 2
- 229910052593 corundum Inorganic materials 0.000 claims description 2
- 229910052906 cristobalite Inorganic materials 0.000 claims description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 claims description 2
- 239000002808 molecular sieve Substances 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052682 stishovite Inorganic materials 0.000 claims description 2
- 229910052905 tridymite Inorganic materials 0.000 claims description 2
- 229910001845 yogo sapphire Inorganic materials 0.000 claims description 2
- 239000010457 zeolite Substances 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 11
- 230000002378 acidificating effect Effects 0.000 abstract description 10
- 229930195733 hydrocarbon Natural products 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 7
- 150000007513 acids Chemical class 0.000 abstract description 2
- 239000012707 chemical precursor Substances 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 239000002028 Biomass Substances 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000000446 fuel Substances 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- -1 alkyl- benzene compounds Chemical class 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000209149 Zea Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 238000005815 base catalysis Methods 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 150000001924 cycloalkanes Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000002918 Fraxinus excelsior Nutrition 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- 241000209504 Poaceae Species 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 239000002956 ash Substances 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- JBQYATWDVHIOAR-UHFFFAOYSA-N tellanylidenegermanium Chemical compound [Te]=[Ge] JBQYATWDVHIOAR-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
-
- 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/002—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal in combination with oil conversion- or refining processes
-
- 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
- C10G1/083—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts in the presence of a solvent
-
- 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
- C10G1/00—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal
- C10G1/08—Production of liquid hydrocarbon mixtures from oil-shale, oil-sand, or non-melting solid carbonaceous or similar materials, e.g. wood, coal with moving catalysts
- C10G1/086—Characterised by the catalyst used
-
- 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
-
- 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
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4018—Spatial velocity, e.g. LHSV, WHSV
-
- 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
- C10G2400/30—Aromatics
-
- 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
Definitions
- This invention relates to processes for obtaining hydrocarbons from biomass. More particularly, this invention relates to the treatment of lignin and cellulosic waste to produce chemicals or fuels.
- Biomass is a renewable resource that can provide some of the needs for sources of chemicals and fuels.
- Biomass includes, but is not limited to, plant parts, fruits, vegetables, plant processing waste, wood chips, chaff, grain, grasses, corn, corn husks, weeds, aquatic plants, hay, paper, paper products, recycled paper and paper products, and any cellulose containing biological material or material of biological origin.
- the economics depend on the ability to produce large amounts of biomass on marginal land, or in a water environment where there are few or no other significantly competing economic uses of that land or water environment. The economics can also depend on the disposal of biomass that would normally be placed in a landfill.
- biomass contributes to the removal of carbon dioxide from the atmosphere as the biomass grows.
- the use of biomass can be one process for recycling atmospheric carbon while producing fuels and chemical precursors.
- Biomass when heated in an environment with low or no oxygen will generate a liquid product known as pyrolysis oil.
- Biomass also contains a significant amount of lignin, which contains a substantial amount of material that can be used as precursors for chemical and fuels.
- the lignin structure contains aromatic rings that are linked together through carbon-carbon bonds and through carbon-oxygen bonds.
- the compounds that have high value are the alkyl- benzene compounds and phenolic compounds that can be recovered from the biomass.
- One of ways to convert lignin to fuels or chemicals is by base catalyzed depolymerization followed by hydrotreating. This process uses a strong base to partially break up the lignin compounds.
- One major problem of this approach is high consumption of strong base such as NaOH which makes it not very attractive from economic stand point of view.
- Our recent study showed that final pH of reaction product need to be above 12.4 in order to have high lignin conversion. This makes the use of low cost basic materials such as boiler ashes impractical.
- the present invention for recovering chemicals from lignin includes a combining lignin with a hydrogenation catalyst to form a mixture under a hydrogen atmosphere. The mixture is reacted at hydrolysis process conditions to form an intermediate product stream having reduced oxygen content, and producing less acidic mixture of oxygenates and hydrocarbons.
- the intermediate product stream is contacted with a dehydrogenation and deoxygenation catalyst at dehydrogenation and deoxygenation reaction conditions thereby generating a product stream comprising aromatic compounds.
- a dehydrogenation and deoxygenation catalyst at dehydrogenation and deoxygenation reaction conditions thereby generating a product stream comprising aromatic compounds.
- Figure 1 shows the basic steps of the process as applied to an idealized situation, where a phenolic compound is hydrogenated and then deoxygenated;
- Figure 2 shows the effect of pH on the insoluble yield of two lignin samples.
- Biomass comprises a substantial amount of carbonaceous material that can be converted to hydrocarbons.
- the biomass material comprises carbohydrates, and other oxygenates.
- One important organic material is the lignin that is found in most vegetative biomass.
- the lignin comprises useful aromatic ring compounds, such that when the lignin is broken down, the aromatic ring compounds can be recovered and used as precursors to polymers, fuels, or other materials.
- Base catalysis for the depolymerization of the lignin can break down the lignin for the recovery of phenols and other aromatic compounds.
- base catalysis uses a large amount of a strong basic material for this process.
- the high usages of a strong base is required for obtaining sufficient solubility of the lignin, in order for the hydrodeoxygenation reaction to proceed.
- One of the main reasons for the large consumption of the base is that the reaction products include phenols and phenolic derivatives and carbon dioxide. These are acidic compounds and neutralize the base during the process.
- the reduction in the need for a strong base can reduce cost and the handling of strong chemicals.
- the acidic environment from the aromatic oxygenate derivatives can be reduced by hydrogenating the aromatic rings and removing some of the oxygen to convert the aromatic oxygenates to less acidic saturated hydrocarbon compounds.
- An example is the conversion of phenolic compounds to less acidic alcohols, such as cyclohexanol.
- the hydrogenated compounds can be further deoxygenated to naphthenic compounds, such as cyclohexane with the oxygen atoms removed.
- a base when a base is used in the process, it is liberated and can be recovered and reused. Hydrogen can be recovered in the subsequent dehydrogenation and deoxygenation step for converting the cyclic hydrocarbons back to aromatics.
- the present invention for producing chemicals from lignin comprises combining the lignin with a hydrogenation catalyst under a hydrogen atmosphere, forming a lignin slurry mixture.
- the mixture is reacted at lignin hydrolysis process conditions to form an intermediate product stream having a reduced oxygenate content and a lower acidity.
- lignin hydrolysis process conditions to form an intermediate product stream having a reduced oxygenate content and a lower acidity.
- some of the aromatic compounds are hydrogenated to saturated or partially saturated hydrocarbon compounds.
- the intermediate product stream is contacted with a dehydrogenation and deoxygenation catalyst at dehydrogenation reaction conditions to form a product stream comprising aromatic compounds.
- the two-step process is shown in Figure 1, which is an idealized simplification of the process.
- the first step hydrogenates more acidic oxygenate compounds, such as phenolic compounds, by removing some of the oxygen and performing at least a partial catalytic hydrogenation of the aromatic compounds to produce much less acidic hydrocarbons, such as cycloalkane alcohols or cycloalkanes, and to depolymerize the lignin and remove oxygen from the lignin.
- the second step catalytically deoxygenates and dehydrogenates the hydrocarbons, such as cycloalkane alcohols or cycloalkanes, to produce aromatics.
- the process can further comprise adding a base to the slurry and hydrogenation catalyst to form a mixture having a pH greater than 6, and preferably having a pH between 8 and 12 during the hydrolysis process.
- the process further comprises recovering the base used in the hydrolysis process.
- a weaker base can be used, and bases are selected from alkali metal hydroxides, alkaline earth metal hydroxides, alkaline earth metal oxides, alkali metal carbonates, and mixtures thereof.
- the hydrolysis reaction conditions include heating the reactor to a temperature between 100 0 C and 450°C, with a preferred temperature between 25O 0 C and 450°C.
- the hydrolysis requires the addition of hydrogen, and the hydrogen is under an atmosphere at a pressure between 0.7 MPa (100 psia) to 21 MPa (3050 psia), and preferably between 3.4 MPa (493 psia) to 14 MPa (2030 psia).
- the hydrogenation reaction condition is operated at a liquid hourly space velocity (LHSV) is between 0.1 and 100 hr "1 .
- LHSV liquid hourly space velocity
- the hydrolysis process is operated over a hydrogenation catalyst, which comprises a metal on a support.
- a preferred hydrogenation catalytic metal is a noble metal, and especially one selected from the platinum group. Two metals that are preferred are platinum (Pt) and palladium (Pd).
- Supports for the catalyst include zeolites, molecular sieves, Al 2 O 3 , SiO 2 , MgO, ZrO 2 , TiO 2 , mixed metal oxides and carbon.
- the hydrogenation catalyst can comprise a base metal on a support.
- Base metals useable in this process include nickel (Ni), chromium (Cr), molybdenum (Mo) and tungsten (W).
- the process can also use a metal sulfide, wherein the metal in the metal sulfide is selected from one or more of the base metals listed.
- the hydrogenation process catalyst can comprise a second metal, wherein the second metal is includes one or more of the metals: tin (Sn), indium (In), ruthenium (Ru), rhodium (Rh), rhenium (Re), osmium (Os), iridium (Ir), germanium (Ge), lead (Pb), cobalt (Co), gallium (Ga), zinc (Zn) and thallium (Tl).
- the second step of the process comprises dehydrogenation and deoxygenation of the hydrocarbon ring compounds, or naphthenes, such as cyclohexane, and hydrocarbon compounds having cyclohexane rings.
- the dehydrogenation and deoxygenation reactions removes the oxygen and returns the naphthenes to a product stream comprising aromatic compounds under dehydrogenation conditions.
- the reaction conditions include a pressure between 1 kPa and 1013 kPa, a temperature between 40O 0 C and 900 0 C, and a liquid hourly space velocity (LHSV) between 0.1 and 100 hr "1 .
- the product stream has benzenes, toluenes, and other alkyl-benzenes that can be separated for use as precursors to other processes, including the formation of fuel feedstocks.
- the dehydrogenation and deoxygenation step can include a cracking function for further depolymerization of the lignin molecules.
- the cracking function can be provided by an acid function from the catalyst, or provided by a cracking function from the catalyst involving a cracking metal.
- Figure 2 illustrates the consumption of a base in the conversion of lignin from two different sources of lignin.
- the process requires the solubilization of lignin to enable the breakdown of lignin into smaller molecules.
- a large amount of base is required to carry out the process, and the base needs to be sufficiently strong to enable the raising of the pH to greater than 12.4 in order to achieve a low percentage of insoluble materials.
- the results illustrate that the amount of base, when the base is NaOH, has to be greater than 40% of the amount of lignin, by weight, to achieve a sufficiently high pH and the desired solubility.
- the hydrogenation process reduces the need for a significant addition of a strong base to the lignin solution by hydrogenating the more acidic oxygenates, such as phenolic compounds, in addition to depolymerizing the lignin, thereby creating an intermediate stream.
- the process is then continued with a second step where the intermediate stream is processed using a dehydrogenation and deoxygenation catalyst at dehydrogenation and deoxygenation conditions, thereby generating a hydrocarbon stream comprising aromatics.
- the effect of the hydrogenation function produces a higher soluble product without the need for the addition of strong base, as illustrated in Table 1.
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- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
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Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
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EP20090840947 EP2401344A4 (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
CA2753355A CA2753355C (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
MX2011009040A MX2011009040A (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion. |
BRPI0924309A BRPI0924309A2 (en) | 2009-02-27 | 2009-12-10 | process to produce chemicals from lignin |
CN200980158939.8A CN102414297B (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
AU2009341104A AU2009341104B2 (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
SG2011060449A SG173805A1 (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
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US12/394,892 | 2009-02-27 | ||
US12/394,892 US8871989B2 (en) | 2009-02-27 | 2009-02-27 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
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PCT/US2009/067422 WO2010098801A1 (en) | 2009-02-27 | 2009-12-10 | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
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US (1) | US8871989B2 (en) |
EP (1) | EP2401344A4 (en) |
CN (1) | CN102414297B (en) |
AU (1) | AU2009341104B2 (en) |
BR (1) | BRPI0924309A2 (en) |
CA (1) | CA2753355C (en) |
CL (1) | CL2011002085A1 (en) |
MX (1) | MX2011009040A (en) |
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SG (1) | SG173805A1 (en) |
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- 2009-12-10 SG SG2011060449A patent/SG173805A1/en unknown
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SG173805A1 (en) | 2011-09-29 |
US20100137663A1 (en) | 2010-06-03 |
MX2011009040A (en) | 2011-09-15 |
US8871989B2 (en) | 2014-10-28 |
EP2401344A1 (en) | 2012-01-04 |
CN102414297B (en) | 2014-09-17 |
AU2009341104B2 (en) | 2013-09-19 |
CL2011002085A1 (en) | 2012-04-13 |
CA2753355C (en) | 2014-01-28 |
CN102414297A (en) | 2012-04-11 |
BRPI0924309A2 (en) | 2016-01-26 |
MY156665A (en) | 2016-03-15 |
EP2401344A4 (en) | 2014-09-17 |
AU2009341104A1 (en) | 2011-09-08 |
CA2753355A1 (en) | 2010-09-02 |
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