CA2605672A1 - Procedes de conversion catalytique de lignine en biocarburants - Google Patents
Procedes de conversion catalytique de lignine en biocarburants Download PDFInfo
- Publication number
- CA2605672A1 CA2605672A1 CA002605672A CA2605672A CA2605672A1 CA 2605672 A1 CA2605672 A1 CA 2605672A1 CA 002605672 A CA002605672 A CA 002605672A CA 2605672 A CA2605672 A CA 2605672A CA 2605672 A1 CA2605672 A1 CA 2605672A1
- Authority
- CA
- Canada
- Prior art keywords
- lignin
- reaction
- partially
- catalyst
- product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 121
- 230000008569 process Effects 0.000 title claims abstract description 107
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 90
- 229920005610 lignin Polymers 0.000 title claims abstract description 82
- 239000002551 biofuel Substances 0.000 title claims abstract description 20
- 230000003197 catalytic effect Effects 0.000 title description 11
- 239000007788 liquid Substances 0.000 title description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 82
- 239000000463 material Substances 0.000 claims abstract description 47
- 230000006641 stabilisation Effects 0.000 claims abstract description 21
- 238000011105 stabilization Methods 0.000 claims abstract description 21
- 238000007670 refining Methods 0.000 claims abstract description 17
- 238000012691 depolymerization reaction Methods 0.000 claims abstract description 10
- 238000004517 catalytic hydrocracking Methods 0.000 claims description 30
- 230000002378 acidificating effect Effects 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 20
- 238000005984 hydrogenation reaction Methods 0.000 claims description 18
- 238000006266 etherification reaction Methods 0.000 claims description 15
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 13
- -1 transition metal nitrides Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 10
- 150000005205 dihydroxybenzenes Chemical class 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052723 transition metal Inorganic materials 0.000 claims description 9
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 8
- 239000011949 solid catalyst Substances 0.000 claims description 7
- 229910052750 molybdenum Inorganic materials 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 5
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 5
- 235000011118 potassium hydroxide Nutrition 0.000 claims description 5
- 239000000377 silicon dioxide Substances 0.000 claims description 5
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 4
- 235000011116 calcium hydroxide Nutrition 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 claims description 3
- 239000000347 magnesium hydroxide Substances 0.000 claims description 3
- 229910001862 magnesium hydroxide Inorganic materials 0.000 claims description 3
- 235000012254 magnesium hydroxide Nutrition 0.000 claims description 3
- 229910003178 Mo2C Inorganic materials 0.000 claims description 2
- 229910015421 Mo2N Inorganic materials 0.000 claims description 2
- 229910002839 Pt-Mo Inorganic materials 0.000 claims description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 235000012239 silicon dioxide Nutrition 0.000 claims description 2
- 150000003624 transition metals Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 89
- 238000004939 coking Methods 0.000 abstract description 16
- 239000000446 fuel Substances 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 239000002816 fuel additive Substances 0.000 abstract description 8
- 238000013461 design Methods 0.000 abstract description 3
- 239000012263 liquid product Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003502 gasoline Substances 0.000 description 15
- 239000002585 base Substances 0.000 description 13
- 150000002989 phenols Chemical class 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 12
- 239000001301 oxygen Substances 0.000 description 12
- 238000011282 treatment Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 238000012545 processing Methods 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 7
- 239000002028 Biomass Substances 0.000 description 6
- 150000008378 aryl ethers Chemical class 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000004996 alkyl benzenes Chemical class 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000003350 kerosene Substances 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 230000000607 poisoning effect Effects 0.000 description 5
- 239000012429 reaction media Substances 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000013459 approach Methods 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 229910052681 coesite Inorganic materials 0.000 description 4
- 229910052906 cristobalite Inorganic materials 0.000 description 4
- 238000005516 engineering process Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 4
- 231100000572 poisoning Toxicity 0.000 description 4
- 229910052682 stishovite Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229910052905 tridymite Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 150000004074 biphenyls Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 239000003254 gasoline additive Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 150000002468 indanes Chemical class 0.000 description 3
- 150000002790 naphthalenes Chemical class 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 125000005329 tetralinyl group Chemical class C1(CCCC2=CC=CC=C12)* 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- 239000002023 wood Substances 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000592342 Tracheophyta Species 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229920001222 biopolymer Polymers 0.000 description 2
- HUCVOHYBFXVBRW-UHFFFAOYSA-M caesium hydroxide Chemical compound [OH-].[Cs+] HUCVOHYBFXVBRW-UHFFFAOYSA-M 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 210000002421 cell wall Anatomy 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000001247 metal acetylides Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229930015704 phenylpropanoid Natural products 0.000 description 2
- 150000002995 phenylpropanoid derivatives Chemical class 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- YHEWWEXPVKCVFY-UHFFFAOYSA-N 2,6-Dimethoxy-4-propylphenol Chemical compound CCCC1=CC(OC)=C(O)C(OC)=C1 YHEWWEXPVKCVFY-UHFFFAOYSA-N 0.000 description 1
- OMNGOGILVBLKAS-UHFFFAOYSA-N 2-methoxyphenol Chemical compound COC1=CC=CC=C1O.COC1=CC=CC=C1O OMNGOGILVBLKAS-UHFFFAOYSA-N 0.000 description 1
- KLSLBUSXWBJMEC-UHFFFAOYSA-N 4-Propylphenol Chemical compound CCCC1=CC=C(O)C=C1 KLSLBUSXWBJMEC-UHFFFAOYSA-N 0.000 description 1
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- 229910003320 CeOx Inorganic materials 0.000 description 1
- 229910019923 CrOx Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005224 alkoxybenzenes Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 150000002765 bicyclohexyls Chemical class 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000000571 coke Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
- 230000003635 deoxygenating effect Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000004674 formic acids Chemical class 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
- 229920005611 kraft lignin Polymers 0.000 description 1
- 150000005573 methoxybenzenes Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000010813 municipal solid waste Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 150000004767 nitrides Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000123 paper Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000010235 potassium benzoate Nutrition 0.000 description 1
- 229940103091 potassium benzoate Drugs 0.000 description 1
- 239000004300 potassium benzoate Substances 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000003797 solvolysis reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000003930 superacid Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010457 zeolite 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
- C10G1/002—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
- C10G1/086—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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Liquid Carbonaceous Fuels (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67766205P | 2005-05-02 | 2005-05-02 | |
| US60/677,662 | 2005-05-02 | ||
| PCT/US2006/016969 WO2006119357A2 (fr) | 2005-05-02 | 2006-05-02 | Procedes de conversion catalytique de lignine en biocarburants |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2605672A1 true CA2605672A1 (fr) | 2006-11-09 |
Family
ID=37308674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002605672A Abandoned CA2605672A1 (fr) | 2005-05-02 | 2006-05-02 | Procedes de conversion catalytique de lignine en biocarburants |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1888713A4 (fr) |
| CN (1) | CN101171324B (fr) |
| BR (1) | BRPI0611343A2 (fr) |
| CA (1) | CA2605672A1 (fr) |
| MX (1) | MX2007013672A (fr) |
| WO (1) | WO2006119357A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527065A (zh) * | 2021-07-14 | 2021-10-22 | 中国科学院广州能源研究所 | Pd/C催化剂协同碱催化剂在乙醇-水溶剂中催化解聚碱木质素制备航油前驱体的方法 |
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| US7964761B2 (en) | 2005-05-02 | 2011-06-21 | University Of Utah Research Foundation | Processes for catalytic conversion of lignin to liquid bio-fuels and novel bio-fuels |
| JP2010514548A (ja) | 2006-12-20 | 2010-05-06 | ヴァイレント エナジー システムズ インク． | 気体生成物生成用リアクタシステム |
| US7977517B2 (en) | 2007-03-08 | 2011-07-12 | Virent Energy Systems, Inc. | Synthesis of liquid fuels and chemicals from oxygenated hydrocarbons |
| US8119847B2 (en) | 2007-06-15 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Catalytic process for converting renewable resources into paraffins for use as diesel blending stocks |
| WO2009037281A2 (fr) * | 2007-09-18 | 2009-03-26 | Basf Se | Procédé d'hydrogénolyse de lignine sur des carbures de métaux de transition |
| US8697924B2 (en) | 2008-09-05 | 2014-04-15 | Shell Oil Company | Liquid fuel compositions |
| BRPI0918489A2 (pt) | 2008-09-08 | 2015-12-01 | Basf Se | processo integrado para produzir polpa e pelo menos um material de valor de baixo peso molecular |
| WO2010094697A1 (fr) | 2009-02-17 | 2010-08-26 | Bergen Teknologioverføring As | Liquéfaction de lignine avec des composants gazeux |
| US8871989B2 (en) * | 2009-02-27 | 2014-10-28 | Uop Llc | Combination of hydrogenation and base catalyzed depolymerization for lignin conversion |
| AU2010259937B2 (en) | 2009-06-13 | 2016-07-14 | Archer-Daniels-Midland Company | Production of adipic acid and derivatives from carbohydrate-containing materials |
| US8669397B2 (en) | 2009-06-13 | 2014-03-11 | Rennovia, Inc. | Production of adipic acid and derivatives from carbohydrate-containing materials |
| AU2010259935B2 (en) | 2009-06-13 | 2016-05-26 | Archer-Daniels-Midland Company | Production of glutaric acid and derivatives from carbohydrate-containing materials |
| WO2011028788A1 (fr) * | 2009-09-01 | 2011-03-10 | Paul O'connor | Conversion à température optimisée de biomasse lignocellulosique |
| US8882924B2 (en) | 2009-09-01 | 2014-11-11 | Kior, Inc. | Pretreatment of solid biomass material comprising cellulose with ionic liquid medium |
| WO2011027220A1 (fr) | 2009-09-01 | 2011-03-10 | Paul O'connor | Procédé amélioré de dissolution de biomasse cellulosique dans un milieu liquide ionique |
| US8404908B2 (en) * | 2009-10-13 | 2013-03-26 | Uop Llc | Process for lignin conversion to chemicals or fuels with H2 generated from lignin depolymerization products |
| US9447347B2 (en) | 2009-12-31 | 2016-09-20 | Shell Oil Company | Biofuels via hydrogenolysis-condensation |
| US9303226B2 (en) | 2009-12-31 | 2016-04-05 | Shell Oil Company | Direct aqueous phase reforming of bio-based feedstocks |
| US8669393B2 (en) | 2010-03-05 | 2014-03-11 | Rennovia, Inc. | Adipic acid compositions |
| EP2566595A4 (fr) * | 2010-05-07 | 2014-08-06 | Solray Energy Ltd | Biomasses pour la production de stock d'alimentation pétrochimique de substitution |
| CN102947248B (zh) | 2010-05-12 | 2016-06-29 | 国际壳牌研究有限公司 | 包括生物质氢解及随后脱氢和醇醛缩合以生产链烷烃的方法 |
| CN102933525A (zh) | 2010-05-12 | 2013-02-13 | 国际壳牌研究有限公司 | 包括生物质氢解及随后脱氢和醇醛缩合以生产链烷烃的方法 |
| US9770705B2 (en) | 2010-06-11 | 2017-09-26 | Rennovia Inc. | Oxidation catalysts |
| PL3401410T3 (pl) | 2010-06-26 | 2021-11-29 | Virdia, Llc | Sposoby wytwarzania mieszanek cukrów |
| IL206678A0 (en) | 2010-06-28 | 2010-12-30 | Hcl Cleantech Ltd | A method for the production of fermentable sugars |
| EP2635659B1 (fr) * | 2010-11-04 | 2023-03-01 | Albemarle Europe Sprl. | Procede de hydrodeoxygenation d'huile de pyrolyse en présence d'un alcohol ajouté |
| BR112013015553A2 (pt) * | 2010-12-20 | 2016-09-20 | Shell Int Research | sistema de conversão de biomassa, ,e, método |
| US9512495B2 (en) | 2011-04-07 | 2016-12-06 | Virdia, Inc. | Lignocellulose conversion processes and products |
| KR20140051255A (ko) * | 2011-06-17 | 2014-04-30 | 바이오켐텍스 에스.피.에이 | 리그린 전환 공정 |
| US8754275B2 (en) | 2011-07-26 | 2014-06-17 | Uop Llc | Methods and apparatuses for producing aromatic hydrocarbon-rich effluent from lignocellulosic material |
| US8772558B2 (en) | 2011-07-26 | 2014-07-08 | Uop Llc | Methods and apparatuses for producing aromatic hydrocarbon-containing effluent |
| US8772557B2 (en) | 2011-07-26 | 2014-07-08 | Uop Llc | Aromatic hydrocarbons from depolymerization and deoxygenation of lignin |
| US9080109B2 (en) * | 2011-12-14 | 2015-07-14 | Uop Llc | Methods for deoxygenating biomass-derived pyrolysis oil |
| US20130232852A1 (en) * | 2012-03-09 | 2013-09-12 | Thesis Chemistry, Llc | Method for tiered production of biobased chemicals and biofuels from lignin |
| US20130232853A1 (en) * | 2012-03-09 | 2013-09-12 | Thesis Chemistry, Llc | Method for selective production of biobased chemicals and biofuels from plant lignin |
| CN102604668B (zh) * | 2012-03-16 | 2014-09-03 | 山西盛驰科技有限公司 | 一种过渡金属碳化物在生物质油加氢脱氧中的应用 |
| CA2877498A1 (fr) * | 2012-06-28 | 2014-01-03 | Joseph Broun Powell | Systemes de conversion de biomasse fournissant une stabilisation integree d'un hydrolysat grace a un catalyseur en bouillie apres pretraitement de la biomasse et methode d'utilisation de ceux-ci |
| SE1551720A1 (sv) * | 2013-05-29 | 2015-12-29 | Kiram Ab | A method for the treatment of spent pulping liquor for the removal and production of a ligning containing product |
| CN105378036B (zh) * | 2013-07-24 | 2017-07-04 | 华东理工大学 | 由生物质产生烷烃的方法 |
| US9435002B2 (en) * | 2014-06-07 | 2016-09-06 | Api Intellectual Property Holdings, Llc | Continuous processes for hydrolyzing hemicelluloses from ligocellulosic materials with cleaning system |
| CN104073278A (zh) * | 2014-07-15 | 2014-10-01 | 厦门大学 | 一种将木质素两步法转化为液体燃料的方法 |
| WO2016081082A1 (fr) * | 2014-11-20 | 2016-05-26 | Exxonmobil Chemical Patents Inc. | Conversion de lignine en carburants et en composés aromatiques |
| FR3030560B1 (fr) * | 2014-12-18 | 2017-01-27 | Ifp Energies Now | Procede de transformation de biomasse lignocellulosique en hydrocarbures et en molecules oxygenees |
| CA2998574C (fr) * | 2015-09-16 | 2022-07-19 | Sca Forest Products Ab | Procede discontinu de production de bio-huile a partir d'une liqueur noire usee |
| DK3350289T3 (da) * | 2015-09-16 | 2020-06-02 | Sca Forest Prod Ab | Kontinuerlig fremgangsmåde til fremstilling af bioolie ud fra brugt sortlud |
| EP3371279B1 (fr) * | 2015-11-04 | 2020-01-15 | SCA Forest Products AB | Procédé de production d'un produit hydrocarboné à partir d'huile de lignine |
| US10240099B2 (en) | 2016-10-27 | 2019-03-26 | Uop Llc | Processes for producing a fuel from a renewable feedstock |
| CN107417498B (zh) * | 2017-05-24 | 2020-01-31 | 中国科学技术大学 | 一种催化解聚木质素的方法 |
| EP3561177A1 (fr) | 2018-04-26 | 2019-10-30 | Sca Forest Products AB | Procédé de production de papier hydrophobe |
| CN112892539A (zh) * | 2019-12-03 | 2021-06-04 | 中国科学院广州能源研究所 | 一种非均相催化剂与均相催化剂耦合氢解木质素的方法 |
| CN113117688A (zh) * | 2021-04-22 | 2021-07-16 | 福州大学 | 一种mof前驱体钼镍催化剂、其制备方法以及其在木质素降解中的应用 |
| CN115106111B (zh) * | 2022-03-21 | 2023-08-15 | 安徽理工大学 | 一种碳化钼粒径依赖型氮掺杂碳材料催化剂及其制备方法和应用 |
| SE2230431A1 (en) * | 2022-12-19 | 2024-06-20 | Votion Biorefineries Ab | A method for the preparation of chemicals and fuels from biomass |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067654C (zh) * | 1996-02-02 | 2001-06-27 | 中国科学院大连化学物理研究所 | 大比表面双组元过渡金属氮化物及其合成方法 |
| US5959167A (en) * | 1997-08-25 | 1999-09-28 | The University Of Utah Research Foundation | Process for conversion of lignin to reformulated hydrocarbon gasoline |
| US6172272B1 (en) * | 1998-08-21 | 2001-01-09 | The University Of Utah | Process for conversion of lignin to reformulated, partially oxygenated gasoline |
| CN1169621C (zh) * | 2002-04-10 | 2004-10-06 | 中国科学院大连化学物理研究所 | 一种过渡金属碳化物催化剂的制备方法及其催化性能 |
-
2006
- 2006-05-02 MX MX2007013672A patent/MX2007013672A/es not_active Application Discontinuation
- 2006-05-02 CN CN2006800150036A patent/CN101171324B/zh not_active Expired - Fee Related
- 2006-05-02 WO PCT/US2006/016969 patent/WO2006119357A2/fr active Application Filing
- 2006-05-02 EP EP06758980A patent/EP1888713A4/fr not_active Withdrawn
- 2006-05-02 CA CA002605672A patent/CA2605672A1/fr not_active Abandoned
- 2006-05-02 BR BRPI0611343-5A patent/BRPI0611343A2/pt not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113527065A (zh) * | 2021-07-14 | 2021-10-22 | 中国科学院广州能源研究所 | Pd/C催化剂协同碱催化剂在乙醇-水溶剂中催化解聚碱木质素制备航油前驱体的方法 |
| CN113527065B (zh) * | 2021-07-14 | 2023-10-13 | 中国科学院广州能源研究所 | Pd/C催化剂协同碱催化剂在乙醇-水溶剂中催化解聚碱木质素制备航油前驱体的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1888713A4 (fr) | 2011-04-13 |
| EP1888713A2 (fr) | 2008-02-20 |
| MX2007013672A (es) | 2008-01-28 |
| CN101171324B (zh) | 2012-12-12 |
| WO2006119357A3 (fr) | 2007-01-25 |
| WO2006119357A2 (fr) | 2006-11-09 |
| BRPI0611343A2 (pt) | 2010-08-31 |
| CN101171324A (zh) | 2008-04-30 |
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