ES2210997T3 - Procedimiento de isomerizacion de los compuestos aromaticos de ocho atomos de carbono utilizando un catalizador que contiene una zeolita de tipo estructural euo. - Google Patents
Procedimiento de isomerizacion de los compuestos aromaticos de ocho atomos de carbono utilizando un catalizador que contiene una zeolita de tipo estructural euo.Info
- Publication number
- ES2210997T3 ES2210997T3 ES99400739T ES99400739T ES2210997T3 ES 2210997 T3 ES2210997 T3 ES 2210997T3 ES 99400739 T ES99400739 T ES 99400739T ES 99400739 T ES99400739 T ES 99400739T ES 2210997 T3 ES2210997 T3 ES 2210997T3
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- aromatic compounds
- zeolite
- catalyst
- approximately
- 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.)
- Expired - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 51
- 150000001491 aromatic compounds Chemical class 0.000 title claims abstract description 39
- 238000000034 method Methods 0.000 title claims abstract description 32
- 238000006317 isomerization reaction Methods 0.000 title claims abstract description 27
- 239000010457 zeolite Substances 0.000 title claims description 49
- 229910021536 Zeolite Inorganic materials 0.000 title claims description 46
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 title claims description 46
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title abstract description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 48
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 239000000203 mixture Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 238000000926 separation method Methods 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 239000011159 matrix material Substances 0.000 claims description 5
- 150000002736 metal compounds Chemical class 0.000 claims description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052796 boron Inorganic materials 0.000 claims description 3
- 239000010703 silicon Substances 0.000 claims description 3
- 229910052710 silicon Inorganic materials 0.000 claims description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052733 gallium Inorganic materials 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 238000011068 loading method Methods 0.000 claims description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 14
- 229910052680 mordenite Inorganic materials 0.000 description 11
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 7
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 238000004064 recycling Methods 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000001354 calcination Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- -1 aluminas Chemical compound 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 238000007323 disproportionation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010555 transalkylation reaction Methods 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- PFUQSACCWFVIBW-UHFFFAOYSA-N [C].C1=CC=CC=C1 Chemical group [C].C1=CC=CC=C1 PFUQSACCWFVIBW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- ILRRQNADMUWWFW-UHFFFAOYSA-K aluminium phosphate Chemical class O1[Al]2OP1(=O)O2 ILRRQNADMUWWFW-UHFFFAOYSA-K 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 150000005199 trimethylbenzenes Chemical class 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- LEHFSLREWWMLPU-UHFFFAOYSA-B zirconium(4+);tetraphosphate Chemical class [Zr+4].[Zr+4].[Zr+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LEHFSLREWWMLPU-UHFFFAOYSA-B 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2702—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously
- C07C5/2724—Catalytic processes not covered by C07C5/2732 - C07C5/31; Catalytic processes covered by both C07C5/2732 and C07C5/277 simultaneously with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9804526A FR2777275B1 (fr) | 1998-04-08 | 1998-04-08 | Procede d'isomerisation des composes aromatiques a huit atomes de carbone utilisant un catalyseur contenant une zeolithe de type structural euo |
| FR9804526 | 1998-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2210997T3 true ES2210997T3 (es) | 2004-07-01 |
Family
ID=9525123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99400739T Expired - Lifetime ES2210997T3 (es) | 1998-04-08 | 1999-03-25 | Procedimiento de isomerizacion de los compuestos aromaticos de ocho atomos de carbono utilizando un catalizador que contiene una zeolita de tipo estructural euo. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6337427B1 (enExample) |
| EP (1) | EP0949229B1 (enExample) |
| JP (1) | JP4423577B2 (enExample) |
| KR (1) | KR100599132B1 (enExample) |
| CN (1) | CN1174944C (enExample) |
| AR (1) | AR018834A1 (enExample) |
| CA (1) | CA2266765C (enExample) |
| ES (1) | ES2210997T3 (enExample) |
| FR (1) | FR2777275B1 (enExample) |
| TW (1) | TW473464B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2895282B1 (fr) * | 2005-12-22 | 2008-02-01 | Inst Francais Du Petrole | Catallyseur bizeolithique comprenant un metal du groupe viii et un metal du groupe iiia et son utilisation en isomerisation des composes c8 aromatiques |
| FR2915112B1 (fr) * | 2007-04-23 | 2009-11-20 | Inst Francais Du Petrole | Procede d'isomerisation d'une coupe c8 aromatique en presence d'un catalyseur a base d'une zeolithe euo desaluminee. |
| CN102039161B (zh) * | 2009-10-16 | 2012-12-26 | 中国石油化工股份有限公司 | C8芳烃异构化催化剂及其应用 |
| US8576521B2 (en) | 2011-08-16 | 2013-11-05 | Schneider Electric USA, Inc. | Adaptive light detection for arc mitigation systems |
| FR2984308B1 (fr) | 2011-12-20 | 2013-12-20 | IFP Energies Nouvelles | Procede d'isomerisation d'une coupe c8 aromatique en presence d'un catalyseur a base d'une zeolithe euo et d'un liant particulier |
| US9053881B2 (en) | 2012-08-24 | 2015-06-09 | Schneider Electric USA, Inc. | Arc detection with resistance to nuisance activation through light subtraction |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577475A (en) * | 1969-01-30 | 1971-05-04 | Chevron Res | Isomerization of c8 alkyl aromatics |
| US4062903A (en) * | 1976-09-24 | 1977-12-13 | Chevron Research Company | Process for isomerizing alkylaromatics |
| DE3165380D1 (en) * | 1980-06-12 | 1984-09-13 | Ici Plc | Zeolite eu-1 |
| DE3169731D1 (en) * | 1980-11-04 | 1985-05-09 | Teijin Petrochem Ind | A catalyst composition containing as catalytically active components alumina and a cristalline aluminosilicate zeolite, a process for isomerizing xylenes and ethylbenzene, and use of this catalyst composition |
| EP0793634B1 (en) * | 1994-11-23 | 1999-08-18 | Exxon Chemical Patents Inc. | Hydrocarbon conversion process using a zeolite bound zeolite catalyst |
-
1998
- 1998-04-08 FR FR9804526A patent/FR2777275B1/fr not_active Expired - Lifetime
-
1999
- 1999-03-25 ES ES99400739T patent/ES2210997T3/es not_active Expired - Lifetime
- 1999-03-25 EP EP99400739A patent/EP0949229B1/fr not_active Expired - Lifetime
- 1999-04-05 AR ARP990101529A patent/AR018834A1/es active IP Right Grant
- 1999-04-06 KR KR1019990011797A patent/KR100599132B1/ko not_active Expired - Lifetime
- 1999-04-07 CA CA002266765A patent/CA2266765C/fr not_active Expired - Lifetime
- 1999-04-07 TW TW088105524A patent/TW473464B/zh not_active IP Right Cessation
- 1999-04-07 US US09/287,622 patent/US6337427B1/en not_active Expired - Lifetime
- 1999-04-08 JP JP10074399A patent/JP4423577B2/ja not_active Expired - Lifetime
- 1999-04-08 CN CNB991048539A patent/CN1174944C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2266765A1 (fr) | 1999-10-08 |
| EP0949229B1 (fr) | 2003-10-29 |
| CN1235143A (zh) | 1999-11-17 |
| KR100599132B1 (ko) | 2006-07-12 |
| JP4423577B2 (ja) | 2010-03-03 |
| CA2266765C (fr) | 2009-10-27 |
| KR19990087890A (ko) | 1999-12-27 |
| JPH11349497A (ja) | 1999-12-21 |
| US6337427B1 (en) | 2002-01-08 |
| AR018834A1 (es) | 2001-12-12 |
| FR2777275A1 (fr) | 1999-10-15 |
| FR2777275B1 (fr) | 2000-05-19 |
| TW473464B (en) | 2002-01-21 |
| CN1174944C (zh) | 2004-11-10 |
| EP0949229A1 (fr) | 1999-10-13 |
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