CA2875668A1 - Procede de conversion d'une matiere hydrocarbonee en un produit hydrocarbone fluide comprenant du p-xylene - Google Patents

Procede de conversion d'une matiere hydrocarbonee en un produit hydrocarbone fluide comprenant du p-xylene Download PDF

Info

Publication number: CA2875668A1
Authority: CA; Canada
Prior art keywords: reactor; catalyst; seconds; silicone; hour
Prior art date: 2012-06-05
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

Application number

CA2875668A

Other languages

English (en)

Inventor

George W. Huber

Yu-Ting Cheng

Zhuopeng Wang

Wei Fan

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

University of Massachusetts Amherst

Original Assignee

University of Massachusetts Amherst

Priority date (The priority date 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 date listed.)

2012-06-05

Filing date

2013-06-17

Publication date

2013-12-12

2013-06-17 Application filed by University of Massachusetts Amherst filed Critical University of Massachusetts Amherst

2013-12-12 Publication of CA2875668A1 publication Critical patent/CA2875668A1/fr

Status Abandoned legal-status Critical Current

Links

239000000463 material Substances 0.000 title claims abstract description 165
URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 119
239000012530 fluid Substances 0.000 title claims abstract description 89
150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 57
229930195733 hydrocarbon Natural products 0.000 title claims abstract description 56
239000004215 Carbon black (E152) Substances 0.000 title claims abstract description 51
238000000034 method Methods 0.000 title claims description 137
239000003054 catalyst Substances 0.000 claims abstract description 374
229920001296 polysiloxane Polymers 0.000 claims abstract description 89
150000001875 compounds Chemical class 0.000 claims abstract description 69
239000010457 zeolite Substances 0.000 claims abstract description 67
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 62
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 56
239000002028 Biomass Substances 0.000 claims abstract description 46
238000004519 manufacturing process Methods 0.000 claims abstract description 25
239000011148 porous material Substances 0.000 claims description 180
239000007787 solid Substances 0.000 claims description 141
238000000197 pyrolysis Methods 0.000 claims description 93
238000006243 chemical reaction Methods 0.000 claims description 83
239000000203 mixture Substances 0.000 claims description 61
230000003197 catalytic effect Effects 0.000 claims description 56
-1 methylethyl Chemical group 0.000 claims description 48
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 39
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 36
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 36
229910052799 carbon Inorganic materials 0.000 claims description 36
150000001336 alkenes Chemical class 0.000 claims description 33
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 31
150000001491 aromatic compounds Chemical class 0.000 claims description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 30
IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 30
239000008096 xylene Substances 0.000 claims description 28
239000000571 coke Substances 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 23
150000003738 xylenes Chemical class 0.000 claims description 22
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 17
239000000377 silicon dioxide Substances 0.000 claims description 17
FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 claims description 16
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 16
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 16
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 15
229940078552 o-xylene Drugs 0.000 claims description 15
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 11
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 11
QNLZIZAQLLYXTC-UHFFFAOYSA-N 1,2-dimethylnaphthalene Chemical compound C1=CC=CC2=C(C)C(C)=CC=C21 QNLZIZAQLLYXTC-UHFFFAOYSA-N 0.000 claims description 10
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 10
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
239000008103 glucose Substances 0.000 claims description 10
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 10
239000002023 wood Substances 0.000 claims description 10
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 9
229920002488 Hemicellulose Polymers 0.000 claims description 8
240000008042 Zea mays Species 0.000 claims description 8
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 8
229910052733 gallium Inorganic materials 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229920005610 lignin Polymers 0.000 claims description 8
241000609240 Ambelania acida Species 0.000 claims description 7
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 7
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 7
240000000111 Saccharum officinarum Species 0.000 claims description 7
235000007201 Saccharum officinarum Nutrition 0.000 claims description 7
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 7
239000010905 bagasse Substances 0.000 claims description 7
229910052802 copper Inorganic materials 0.000 claims description 7
239000010949 copper Substances 0.000 claims description 7
235000005822 corn Nutrition 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
150000001720 carbohydrates Chemical class 0.000 claims description 6
235000014633 carbohydrates Nutrition 0.000 claims description 6
230000006324 decarbonylation Effects 0.000 claims description 6
238000006606 decarbonylation reaction Methods 0.000 claims description 6
238000006114 decarboxylation reaction Methods 0.000 claims description 6
230000018044 dehydration Effects 0.000 claims description 6
238000006297 dehydration reaction Methods 0.000 claims description 6
238000006356 dehydrogenation reaction Methods 0.000 claims description 6
238000006317 isomerization reaction Methods 0.000 claims description 6
239000010813 municipal solid waste Substances 0.000 claims description 6
239000004033 plastic Substances 0.000 claims description 6
229920003023 plastic Polymers 0.000 claims description 6
229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 claims description 6
239000010907 stover Substances 0.000 claims description 6
HYFLWBNQFMXCPA-UHFFFAOYSA-N 1-ethyl-2-methylbenzene Chemical compound CCC1=CC=CC=C1C HYFLWBNQFMXCPA-UHFFFAOYSA-N 0.000 claims description 5
ZMXIYERNXPIYFR-UHFFFAOYSA-N 1-ethylnaphthalene Chemical compound C1=CC=C2C(CC)=CC=CC2=C1 ZMXIYERNXPIYFR-UHFFFAOYSA-N 0.000 claims description 5
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
RJTJVVYSTUQWNI-UHFFFAOYSA-N beta-ethyl naphthalene Natural products C1=CC=CC2=CC(CC)=CC=C21 RJTJVVYSTUQWNI-UHFFFAOYSA-N 0.000 claims description 5
229910052804 chromium Inorganic materials 0.000 claims description 5
239000011651 chromium Substances 0.000 claims description 5
229910017052 cobalt Inorganic materials 0.000 claims description 5
239000010941 cobalt Substances 0.000 claims description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 5
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
229910052759 nickel Inorganic materials 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229910052697 platinum Inorganic materials 0.000 claims description 5
229910052720 vanadium Inorganic materials 0.000 claims description 5
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 5
229910052725 zinc Inorganic materials 0.000 claims description 5
239000011701 zinc Substances 0.000 claims description 5
GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 claims description 4
TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 4
239000010828 animal waste Substances 0.000 claims description 4
239000010794 food waste Substances 0.000 claims description 4
239000012978 lignocellulosic material Substances 0.000 claims description 4
HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
238000006384 oligomerization reaction Methods 0.000 claims description 4
239000013502 plastic waste Substances 0.000 claims description 4
LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 claims description 4
239000000811 xylitol Substances 0.000 claims description 4
HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 4
229960002675 xylitol Drugs 0.000 claims description 4
235000010447 xylitol Nutrition 0.000 claims description 4
VSIKJPJINIDELZ-UHFFFAOYSA-N 2,2,4,4,6,6,8,8-octakis-phenyl-1,3,5,7,2,4,6,8-tetraoxatetrasilocane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VSIKJPJINIDELZ-UHFFFAOYSA-N 0.000 claims description 3
VCYDUTCMKSROID-UHFFFAOYSA-N 2,2,4,4,6,6-hexakis-phenyl-1,3,5,2,4,6-trioxatrisilinane Chemical compound O1[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si](C=2C=CC=CC=2)(C=2C=CC=CC=2)O[Si]1(C=1C=CC=CC=1)C1=CC=CC=C1 VCYDUTCMKSROID-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
CCDWGDHTPAJHOA-UHFFFAOYSA-N benzylsilicon Chemical compound [Si]CC1=CC=CC=C1 CCDWGDHTPAJHOA-UHFFFAOYSA-N 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 3
235000010290 biphenyl Nutrition 0.000 claims description 3
125000006267 biphenyl group Chemical group 0.000 claims description 3
HIHIPCDUFKZOSL-UHFFFAOYSA-N ethenyl(methyl)silicon Chemical compound C[Si]C=C HIHIPCDUFKZOSL-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
150000002468 indanes Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 claims description 3
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
239000002910 solid waste Substances 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 1
239000000376 reactant Substances 0.000 abstract description 47
238000007233 catalytic pyrolysis Methods 0.000 abstract description 12
239000000047 product Substances 0.000 description 155
239000002245 particle Substances 0.000 description 56
VQKFNUFAXTZWDK-UHFFFAOYSA-N 2-Methylfuran Chemical compound CC1=CC=CO1 VQKFNUFAXTZWDK-UHFFFAOYSA-N 0.000 description 44
230000008569 process Effects 0.000 description 44
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 43
239000007789 gas Substances 0.000 description 42
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 40
238000009826 distribution Methods 0.000 description 35
239000007788 liquid Substances 0.000 description 30
239000007795 chemical reaction product Substances 0.000 description 26
229910002092 carbon dioxide Inorganic materials 0.000 description 21
238000005243 fluidization Methods 0.000 description 21
235000011089 carbon dioxide Nutrition 0.000 description 19
238000000227 grinding Methods 0.000 description 17
239000002253 acid Substances 0.000 description 16
238000010438 heat treatment Methods 0.000 description 16
229910052734 helium Inorganic materials 0.000 description 16
239000001307 helium Substances 0.000 description 15
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 15
229910052751 metal Inorganic materials 0.000 description 14
239000002184 metal Substances 0.000 description 14
239000000126 substance Substances 0.000 description 14
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 12
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 12
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 12
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 11
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 11
229910044991 metal oxide Inorganic materials 0.000 description 11
150000004706 metal oxides Chemical class 0.000 description 11
AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000012071 phase Substances 0.000 description 10
238000001179 sorption measurement Methods 0.000 description 10
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 10
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
238000006884 silylation reaction Methods 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
229910001868 water Inorganic materials 0.000 description 9
CBMXCNPQDUJNHT-UHFFFAOYSA-N 1,6-dimethylnaphthalene Chemical compound CC1=CC=CC2=CC(C)=CC=C21 CBMXCNPQDUJNHT-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
238000006555 catalytic reaction Methods 0.000 description 8
238000010926 purge Methods 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 7
238000002441 X-ray diffraction Methods 0.000 description 7
125000004435 hydrogen atom Chemical class [H]* 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
239000007800 oxidant agent Substances 0.000 description 7
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 7
238000012546 transfer Methods 0.000 description 7
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
230000005587 bubbling Effects 0.000 description 6
238000001354 calcination Methods 0.000 description 6
239000001913 cellulose Substances 0.000 description 6
229920002678 cellulose Polymers 0.000 description 6
238000004891 communication Methods 0.000 description 6
238000000151 deposition Methods 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
239000000843 powder Substances 0.000 description 6
ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 6
238000011084 recovery Methods 0.000 description 6
241000894007 species Species 0.000 description 6
241000196324 Embryophyta Species 0.000 description 5
239000005977 Ethylene Substances 0.000 description 5
230000002902 bimodal effect Effects 0.000 description 5
230000008021 deposition Effects 0.000 description 5
238000013461 design Methods 0.000 description 5
238000005516 engineering process Methods 0.000 description 5
238000000769 gas chromatography-flame ionisation detection Methods 0.000 description 5
150000002739 metals Chemical class 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
238000012545 processing Methods 0.000 description 5
230000009467 reduction Effects 0.000 description 5
238000006722 reduction reaction Methods 0.000 description 5
239000011343 solid material Substances 0.000 description 5
239000002699 waste material Substances 0.000 description 5
GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 description 4
SDDBCEWUYXVGCQ-UHFFFAOYSA-N 1,5-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1C SDDBCEWUYXVGCQ-UHFFFAOYSA-N 0.000 description 4
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 4
JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 description 4
ZLCSFXXPPANWQY-UHFFFAOYSA-N 3-ethyltoluene Chemical compound CCC1=CC=CC(C)=C1 ZLCSFXXPPANWQY-UHFFFAOYSA-N 0.000 description 4
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
230000009286 beneficial effect Effects 0.000 description 4
238000004364 calculation method Methods 0.000 description 4
239000012159 carrier gas Substances 0.000 description 4
230000008859 change Effects 0.000 description 4
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 4
238000003795 desorption Methods 0.000 description 4
230000000670 limiting effect Effects 0.000 description 4
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
239000001301 oxygen Substances 0.000 description 4
229910052760 oxygen Inorganic materials 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 4
BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
238000012216 screening Methods 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
229910052786 argon Inorganic materials 0.000 description 3
230000008901 benefit Effects 0.000 description 3
239000012075 bio-oil Substances 0.000 description 3
239000002551 biofuel Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
238000009792 diffusion process Methods 0.000 description 3
238000001035 drying Methods 0.000 description 3
XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 description 3
238000005342 ion exchange Methods 0.000 description 3
229910052680 mordenite Inorganic materials 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
230000036961 partial effect Effects 0.000 description 3
239000012466 permeate Substances 0.000 description 3
239000003348 petrochemical agent Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
239000012855 volatile organic compound Substances 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical class C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
239000007848 Bronsted acid Substances 0.000 description 2
244000025254 Cannabis sativa Species 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
241000195493 Cryptophyta Species 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
240000003433 Miscanthus floridulus Species 0.000 description 2
241001520808 Panicum virgatum Species 0.000 description 2
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
239000002154 agricultural waste Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
238000005882 aldol condensation reaction Methods 0.000 description 2
150000001361 allenes Chemical class 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
238000005899 aromatization reaction Methods 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
230000000903 blocking effect Effects 0.000 description 2
IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000004177 carbon cycle Methods 0.000 description 2
239000000969 carrier Substances 0.000 description 2
238000012512 characterization method Methods 0.000 description 2
238000001311 chemical methods and process Methods 0.000 description 2
239000012707 chemical precursor Substances 0.000 description 2
238000000576 coating method Methods 0.000 description 2
238000002485 combustion reaction Methods 0.000 description 2
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
150000001924 cycloalkanes Chemical class 0.000 description 2
LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
230000009849 deactivation Effects 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
210000003608 fece Anatomy 0.000 description 2
229910001657 ferrierite group Inorganic materials 0.000 description 2
239000000835 fiber Substances 0.000 description 2
238000004231 fluid catalytic cracking Methods 0.000 description 2
GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
239000000446 fuel Substances 0.000 description 2
CHPZKNULDCNCBW-UHFFFAOYSA-N gallium nitrate Inorganic materials [Ga+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O CHPZKNULDCNCBW-UHFFFAOYSA-N 0.000 description 2
238000001165 gas chromatography-thermal conductivity detection Methods 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000010871 livestock manure Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000001624 naphthyl group Chemical group 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000010815 organic waste Substances 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
150000002989 phenols Chemical class 0.000 description 2
125000003367 polycyclic group Chemical group 0.000 description 2
229920000728 polyester Polymers 0.000 description 2
229920000139 polyethylene terephthalate Polymers 0.000 description 2
239000005020 polyethylene terephthalate Substances 0.000 description 2
QROGIFZRVHSFLM-UHFFFAOYSA-N prop-1-enylbenzene Chemical class CC=CC1=CC=CC=C1 QROGIFZRVHSFLM-UHFFFAOYSA-N 0.000 description 2
238000005086 pumping Methods 0.000 description 2
238000001812 pycnometry Methods 0.000 description 2
239000010453 quartz Substances 0.000 description 2
238000001878 scanning electron micrograph Methods 0.000 description 2
239000011949 solid catalyst Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KEIFWROAQVVDBN-UHFFFAOYSA-N 1,2-dihydronaphthalene Chemical compound C1=CC=C2C=CCCC2=C1 KEIFWROAQVVDBN-UHFFFAOYSA-N 0.000 description 1
VCDNEJSJJUVVJY-UHFFFAOYSA-N 2,4,6-trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1.CC1=CC(C)=NC(C)=C1 VCDNEJSJJUVVJY-UHFFFAOYSA-N 0.000 description 1
GFJUOMJGSXRJJY-UHFFFAOYSA-N 2-methylprop-1-ene Chemical compound CC(C)=C.CC(C)=C GFJUOMJGSXRJJY-UHFFFAOYSA-N 0.000 description 1
229910000619 316 stainless steel Inorganic materials 0.000 description 1
235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
244000067602 Chamaesyce hirta Species 0.000 description 1
QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
239000005751 Copper oxide Substances 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
238000005698 Diels-Alder reaction Methods 0.000 description 1
240000003133 Elaeis guineensis Species 0.000 description 1
235000001950 Elaeis guineensis Nutrition 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
235000003222 Helianthus annuus Nutrition 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
HPLULNMDFWGYLR-UHFFFAOYSA-N O1C=CC=C1.O1C=CC=C1.O1C=CC=C1.O1C=CC=C1.O1C=CC=C1 Chemical compound O1C=CC=C1.O1C=CC=C1.O1C=CC=C1.O1C=CC=C1.O1C=CC=C1 HPLULNMDFWGYLR-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
235000019482 Palm oil Nutrition 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000219000 Populus Species 0.000 description 1
229920001131 Pulp (paper) Polymers 0.000 description 1
108700031620 S-acetylthiorphan Proteins 0.000 description 1
241000124033 Salix Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
VKLOLKHGESRJBL-UHFFFAOYSA-N [C].CC1=CC=C(C)C=C1 Chemical compound [C].CC1=CC=C(C)C=C1 VKLOLKHGESRJBL-UHFFFAOYSA-N 0.000 description 1
OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical group [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
230000004913 activation Effects 0.000 description 1
125000002015 acyclic group Chemical group 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000003915 air pollution Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical group [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
238000013459 approach Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
239000003225 biodiesel Substances 0.000 description 1
230000008033 biological extinction Effects 0.000 description 1
239000012620 biological material Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
235000009120 camo Nutrition 0.000 description 1
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
235000005607 chanvre indien Nutrition 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
229910000431 copper oxide Inorganic materials 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical compound CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
238000005235 decoking Methods 0.000 description 1
238000011161 development Methods 0.000 description 1
230000018109 developmental process Effects 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
239000004205 dimethyl polysiloxane Substances 0.000 description 1
235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000011066 ex-situ storage Methods 0.000 description 1
238000009313 farming Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001722 flash pyrolysis Methods 0.000 description 1
150000002240 furans Chemical class 0.000 description 1
238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical class COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
239000011487 hemp Substances 0.000 description 1
239000010903 husk Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000009616 inductively coupled plasma Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
239000002085 irritant Substances 0.000 description 1
231100000021 irritant Toxicity 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229910052746 lanthanum Inorganic materials 0.000 description 1
FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
239000003077 lignite Substances 0.000 description 1
239000012263 liquid product Substances 0.000 description 1
235000009973 maize Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
VUZPPFZMUPKLLV-UHFFFAOYSA-N methane;hydrate Chemical compound C.O VUZPPFZMUPKLLV-UHFFFAOYSA-N 0.000 description 1
150000005673 monoalkenes Chemical class 0.000 description 1
239000000178 monomer Substances 0.000 description 1
DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
229920001542 oligosaccharide Polymers 0.000 description 1
150000002482 oligosaccharides Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
150000002938 p-xylenes Chemical class 0.000 description 1
239000002540 palm oil Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000003415 peat Substances 0.000 description 1
RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
235000020030 perry Nutrition 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000010909 process residue Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
IGYQZAUNFSMNKH-UHFFFAOYSA-N prop-1-ene Chemical group CC=C.CC=C.CC=C.CC=C IGYQZAUNFSMNKH-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
229910052761 rare earth metal Inorganic materials 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000002407 reforming Methods 0.000 description 1
238000006057 reforming reaction Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000010865 sewage Substances 0.000 description 1
239000010801 sewage sludge Substances 0.000 description 1
239000003079 shale oil Substances 0.000 description 1
238000005029 sieve analysis Methods 0.000 description 1
239000004460 silage Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000010025 steaming Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000010936 titanium Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000009966 trimming Methods 0.000 description 1
238000010977 unit operation Methods 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000007740 vapor deposition Methods 0.000 description 1
229910052726 zirconium Inorganic materials 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
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/40—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the pentasil type, e.g. types ZSM-5, ZSM-8 or ZSM-11, as exemplified by patent documents US3702886, GB1334243 and US3709979, respectively
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65
- B01J29/72—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups B01J29/08 - B01J29/65 containing iron group metals, noble metals or copper
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/14—After treatment, characterised by the effect to be obtained to alter the inside of the molecular sieve channels
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/32—Reaction with silicon compounds, e.g. TEOS, siliconfluoride
- 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
- 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

Landscapes

Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Oil, Petroleum & Natural Gas (AREA)
Crystallography & Structural Chemistry (AREA)
Materials Engineering (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
General Chemical & Material Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)

CA2875668A 2012-06-05 2013-06-17 Procede de conversion d'une matiere hydrocarbonee en un produit hydrocarbone fluide comprenant du p-xylene Abandoned CA2875668A1 (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US201261655605P	2012-06-05	2012-06-05
US61/655,605		2012-06-05
US13/628,258		2012-09-27
US13/628,258 US20130324772A1 (en)	2012-06-05	2012-09-27	Method for converting a hydrocarbonaceous material to a fluid hydrocarbon product comprising p-xylene
PCT/US2013/046077 WO2013185149A1 (fr)	2012-06-05	2013-06-17	Procédé de conversion d'une matière hydrocarbonée en un produit hydrocarboné fluide comprenant du p-xylène

Publications (1)

Publication Number	Publication Date
CA2875668A1 true CA2875668A1 (fr)	2013-12-12

Family

ID=49671051

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2875668A Abandoned CA2875668A1 (fr)	2012-06-05	2013-06-17	Procede de conversion d'une matiere hydrocarbonee en un produit hydrocarbone fluide comprenant du p-xylene

Country Status (6)

Country	Link
US (1)	US20130324772A1 (fr)
EP (1)	EP2855404A1 (fr)
KR (1)	KR20150045995A (fr)
BR (1)	BR112014030260A2 (fr)
CA (1)	CA2875668A1 (fr)
WO (1)	WO2013185149A1 (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US9249080B2 (en)	2012-10-17	2016-02-02	Anellotech, Inc.	Chemical intermediates by catalytic fast pyrolysis process
US20150166899A1 (en) *	2013-12-14	2015-06-18	Anellotech, Inc.	Catalysts and Processes for Producing p-xylene from Biomass
US20150307418A1 (en) *	2014-04-23	2015-10-29	Uop Llc	Methods and apparatuses for producing xylene from lignin
MY182882A (en) *	2014-07-01	2021-02-05	Anellotech Inc	Processes for converting biomass to btx with low sulfur, nitrogen and olefin content via a catalytic fast pyrolysis process
EP3197984B1 (fr) *	2014-09-22	2023-08-16	Huntsman International LLC	Procédé de préparation de composés aromatiques
WO2016073209A1 (fr)	2014-11-03	2016-05-12	Anellotech, Inc.	Procédé amélioré pour la récupération de monoxyde de carbone à partir d'un produit de pyrolyse catalytique rapide
US10308877B2 (en)	2014-12-29	2019-06-04	Shell Oil Company	Process for production of aromatics via pyrolysis of lignin-comprising material
KR101600430B1 (ko)	2015-01-08	2016-03-07	한국화학연구원	이산화탄소가 풍부한 합성가스로부터 단환 방향족 화합물 및 장쇄올레핀 화합물의 직접 합성방법
DE102015108552A1 (de) *	2015-02-27	2016-09-01	Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V.	Pyrolyseöl und Verfahren zu dessen Herstellung
BR112017019379A2 (pt) *	2015-04-16	2018-06-05	Anellotech Inc	intermediários químicos derivados de biomassa
US10000703B2 (en) *	2015-05-08	2018-06-19	Anellotech, Inc.	Catalytic fast pyrolysis process
CN106565396B (zh) *	2015-10-12	2019-04-12	中国石油化工股份有限公司	环加成生产芳烃的方法
ES2618857B1 (es) *	2015-12-21	2018-07-27	Neoliquid Advanced Biofuels And Biochemicals, S.L.	Procedimiento termoquímico, e instalación, para transformar materiales poliméricos
EP3411461B1 (fr)	2016-02-05	2021-03-10	Anellotech, Inc.	Produits chimiques et mélanges de carburants obtenus par un processus de pyrolyse catalytique rapide
KR101725178B1 (ko) *	2016-03-25	2017-04-10	서울시립대학교 산학협력단	2단계 촉매 열분해를 통한 리그닌으로부터 바이오 오일의 생산
BR112021000789B1 (pt)	2018-07-16	2023-01-17	Anellotech, Inc	Injeção de biomassa em reator de pirólise catalítica de leito fluido
KR102308570B1 (ko) *	2019-04-05	2021-10-06	한국기계연구원	플라스틱 혼합 바이오매스를 이용한 바이오원유 제조시스템 및 이를 이용한 바이오원유 제조방법
EP3786356A1 (fr) *	2019-09-02	2021-03-03	Huntsman International LLC	Procédé de fabrication d'une huile biologique améliorée à partir de liqueur noire
WO2021163132A1 (fr) *	2020-02-10	2021-08-19	Eastman Chemical Company	Recyclage chimique de flux de coproduits de purge de réacteur de solvolyse
CN115052728A (zh) *	2020-02-10	2022-09-13	伊士曼化工公司	溶剂分解副产物流的化学回收
CN115052730A (zh)	2020-02-10	2022-09-13	伊士曼化工公司	处理的混合塑料废物流的化学回收
US12686753B2 (en)	2020-02-10	2026-07-21	Eastman Chemical Company	Chemical recycling of solvolysis terephthalyl column bottoms coproduct streams
WO2021163104A1 (fr)	2020-02-10	2021-08-19	Eastman Chemical Company	Recyclage chimique de flux de coproduits de fond de colonne de solvolyse
WO2021211520A1 (fr) *	2020-04-13	2021-10-21	Eastman Chemical Company	Recyclage chimique de flux de coproduits de solvolyse
CN114317026A (zh) *	2020-09-29	2022-04-12	中国科学技术大学	一种生物质热解油催化裂解的方法
CN113354533B (zh) *	2021-06-01	2024-03-29	中国科学技术大学	一种利用木质纤维素生物质制取对苯二甲酸的方法

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4002697A (en) *	1973-12-03	1977-01-11	Mobil Oil Corporation	Selective production of para-xylene
US4090981A (en)	1976-09-23	1978-05-23	Mobile Oil Corporation	Catalyst for selective production of para dialkyl substituted benzenes
US5243117A (en)	1990-06-05	1993-09-07	Mobil Oil Corp.	Catalyst and process for the selective production of para-dialkyl substituted benzenes
US5403800A (en)	1993-05-28	1995-04-04	Mobil Oil Corp.	Multiple impregnation technique for the preparation of ex situ selectivated zeolite catalysts
US5659098A (en)	1993-05-28	1997-08-19	Beck; Jeffrey S.	High conversion touluene disproportionation with ex situ selectivated zeolite catalysts
WO2009110402A1 (fr) *	2008-03-03	2009-09-11	東レ株式会社	Procédé de production du paraxylène

2012
- 2012-09-27 US US13/628,258 patent/US20130324772A1/en not_active Abandoned
2013
- 2013-06-17 CA CA2875668A patent/CA2875668A1/fr not_active Abandoned
- 2013-06-17 EP EP13742297.8A patent/EP2855404A1/fr not_active Withdrawn
- 2013-06-17 BR BR112014030260A patent/BR112014030260A2/pt not_active IP Right Cessation
- 2013-06-17 KR KR20157000180A patent/KR20150045995A/ko not_active Withdrawn
- 2013-06-17 WO PCT/US2013/046077 patent/WO2013185149A1/fr not_active Ceased

Also Published As

Publication number	Publication date
US20130324772A1 (en)	2013-12-05
WO2013185149A1 (fr)	2013-12-12
EP2855404A1 (fr)	2015-04-08
KR20150045995A (ko)	2015-04-29
BR112014030260A2 (pt)	2017-09-12

Legal Events

Date	Code	Title	Description
2017-07-31	FZDE	Discontinued	Effective date: 20170619

Publication	Publication Date	Title
US20130324772A1 (en)	2013-12-05	Method for converting a hydrocarbonaceous material to a fluid hydrocarbon product comprising p-xylene
US20130060070A1 (en)	2013-03-07	Method for producing fluid hydrocarbons
AU2009220133B2 (en)	2013-12-19	Catalytic pyrolysis of solid biomass and related biofuels, aromatic, and olefin compounds
AU2010292998B2 (en)	2016-03-03	Systems and processes for catalytic pyrolysis of biomass and hydrocarbonaceous materials for production of aromatics with optional olefin recycle, and catalysts having selected particle size for catalytic pyrolysis
US9534174B2 (en)	2017-01-03	Fast catalytic pyrolysis with recycle of side products
US20140031583A1 (en)	2014-01-30	Olefin conditioning in a fast catalytic pyrolysis recycle process
US9249080B2 (en)	2016-02-02	Chemical intermediates by catalytic fast pyrolysis process
US10173207B2 (en)	2019-01-08	Regeneration of catalytic fast pyrolysis catalyst
JP2011514927A5 (fr)	2012-04-12
US20150166899A1 (en)	2015-06-18	Catalysts and Processes for Producing p-xylene from Biomass
CN107207968A (zh)	2017-09-26	改进的催化快速热解工艺
JP2015519377A (ja)	2015-07-09	炭化水素系材料をｐ−キシレンを含んで成る流動性炭化水素生成物に転化するための方法