CA2036143C - Hydrodealkylation catalytique des composes aromatiques - Google Patents

Hydrodealkylation catalytique des composes aromatiques Download PDF

Info

Publication number: CA2036143C
Authority: CA; Canada
Prior art keywords: zeolite; aromatics; ray diffraction; diffraction pattern; interplanar
Prior art date: 1991-02-12
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 - Fee Related

Application number

CA 2036143

Other languages

English (en)

Other versions

CA2036143A1 (fr

Inventor

Paul A. Howley

Stuart S. Shih

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.)

Mobil Oil AS

Original Assignee

Mobil Oil AS

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.)

1991-02-12

Filing date

1991-02-12

Publication date

2002-04-09

1991-02-12 Application filed by Mobil Oil AS filed Critical Mobil Oil AS

1991-02-12 Priority to CA 2036143 priority Critical patent/CA2036143C/fr

1992-08-13 Publication of CA2036143A1 publication Critical patent/CA2036143A1/fr

2002-04-09 Application granted granted Critical

2002-04-09 Publication of CA2036143C publication Critical patent/CA2036143C/fr

2011-02-12 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000003197 catalytic effect Effects 0.000 title claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 81
239000010457 zeolite Substances 0.000 claims abstract description 37
229910021536 Zeolite Inorganic materials 0.000 claims abstract description 35
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 35
238000000034 method Methods 0.000 claims abstract description 34
239000003054 catalyst Substances 0.000 claims abstract description 30
238000002441 X-ray diffraction Methods 0.000 claims abstract description 16
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 10
229910000510 noble metal Inorganic materials 0.000 claims abstract description 6
229910052759 nickel Inorganic materials 0.000 claims abstract description 5
229930195733 hydrocarbon Natural products 0.000 claims abstract description 3
150000002430 hydrocarbons Chemical class 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 34
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
229910052710 silicon Inorganic materials 0.000 claims description 6
239000010703 silicon Substances 0.000 claims description 6
229910052782 aluminium Inorganic materials 0.000 claims description 5
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
229910052697 platinum Inorganic materials 0.000 claims description 5
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
229910052796 boron Inorganic materials 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 2
GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims description 2
229910052733 gallium Inorganic materials 0.000 claims description 2
229910052732 germanium Inorganic materials 0.000 claims description 2
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
229910052763 palladium Inorganic materials 0.000 claims description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 59
238000006243 chemical reaction Methods 0.000 description 39
239000000047 product Substances 0.000 description 26
238000001179 sorption measurement Methods 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000463 material Substances 0.000 description 11
239000011734 sodium Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 8
239000013078 crystal Substances 0.000 description 8
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000011230 binding agent Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000002156 adsorbate Substances 0.000 description 5
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
238000006900 dealkylation reaction Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000020335 dealkylation Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
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 4
229910001220 stainless steel Inorganic materials 0.000 description 4
239000010935 stainless steel Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
239000008096 xylene Substances 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 3
MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000002178 crystalline material Substances 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
-1 e.g. Chemical compound 0.000 description 3
239000011159 matrix material Substances 0.000 description 3
238000012545 processing Methods 0.000 description 3
229910001388 sodium aluminate Inorganic materials 0.000 description 3
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
238000013019 agitation Methods 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
238000001354 calcination Methods 0.000 description 2
239000002131 composite material Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
229910052809 inorganic oxide Inorganic materials 0.000 description 2
229910044991 metal oxide Inorganic materials 0.000 description 2
150000004706 metal oxides Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000002245 particle Substances 0.000 description 2
239000011148 porous material Substances 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000000926 separation method Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000010025 steaming Methods 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
239000004743 Polypropylene Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004115 Sodium Silicate Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
125000000217 alkyl group Chemical class 0.000 description 1
HPTYUNKZVDYXLP-UHFFFAOYSA-N aluminum;trihydroxy(trihydroxysilyloxy)silane;hydrate Chemical group O.[Al].[Al].O[Si](O)(O)O[Si](O)(O)O HPTYUNKZVDYXLP-UHFFFAOYSA-N 0.000 description 1
239000011324 bead Substances 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
LTPBRCUWZOMYOC-UHFFFAOYSA-N beryllium oxide Inorganic materials O=[Be] LTPBRCUWZOMYOC-UHFFFAOYSA-N 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
238000006555 catalytic reaction Methods 0.000 description 1
125000002091 cationic group Chemical group 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
238000007385 chemical modification Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
229910052802 copper Inorganic materials 0.000 description 1
239000010949 copper Substances 0.000 description 1
238000005336 cracking Methods 0.000 description 1
230000001934 delay Effects 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
229910001649 dickite Inorganic materials 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
229910052621 halloysite Inorganic materials 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
239000000395 magnesium oxide Substances 0.000 description 1
CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
238000005259 measurement Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
239000003921 oil Substances 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
238000005215 recombination Methods 0.000 description 1
230000006798 recombination Effects 0.000 description 1
NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
229910052911 sodium silicate Inorganic materials 0.000 description 1
241000894007 species Species 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000003068 static effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
238000007669 thermal treatment Methods 0.000 description 1

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Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

CA 2036143 1991-02-12 1991-02-12 Hydrodealkylation catalytique des composes aromatiques Expired - Fee Related CA2036143C (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2036143 CA2036143C (fr)	1991-02-12	1991-02-12	Hydrodealkylation catalytique des composes aromatiques

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2036143 CA2036143C (fr)	1991-02-12	1991-02-12	Hydrodealkylation catalytique des composes aromatiques

Publications (2)

Publication Number	Publication Date
CA2036143A1 CA2036143A1 (fr)	1992-08-13
CA2036143C true CA2036143C (fr)	2002-04-09

Family

ID=4146985

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2036143 Expired - Fee Related CA2036143C (fr)	1991-02-12	1991-02-12	Hydrodealkylation catalytique des composes aromatiques

Country Status (1)

Country	Link
CA (1)	CA2036143C (fr)

1991
- 1991-02-12 CA CA 2036143 patent/CA2036143C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2036143A1 (fr)	1992-08-13

Legal Events

Date	Code	Title	Description
1997-12-09	EEER	Examination request
2004-02-12	MKLA	Lapsed

Publication	Publication Date	Title
EP0445969B1 (fr)	1994-11-30	Hydrodealkylation catalytique des composés aromatiques
US4954325A (en)	1990-09-04	Composition of synthetic porous crystalline material, its synthesis and use
US5236575A (en)	1993-08-17	Synthetic porous crystalline mcm-49, its synthesis and use
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US4982033A (en)	1991-01-01	Process for converting light aliphatics to aromatics
US4982040A (en)	1991-01-01	Process for the catalytic disproportionation of methylnaphthalenes
US5173281A (en)	1992-12-22	Synthesis of a synthetic porous crystalline material
EP0457853B1 (fr)	1997-08-06	Procede de conversion catalytique d'une charge de composes c9+ aromatiques
US5043513A (en)	1991-08-27	Catalytic hydrodealkylation of aromatics
US5073655A (en)	1991-12-17	Method for preparing diarylalkanes
US5107054A (en)	1992-04-21	Zeolite MCM-22 based catalyst for paraffin isomerization
CA2036143C (fr)	2002-04-09	Hydrodealkylation catalytique des composes aromatiques
US5026943A (en)	1991-06-25	Catalytic conversion over catalyst comprising synthetic crystal MCM-35
EP0398998A1 (fr)	1990-11-28	Materiau cristallin poreux synthetique, sa synthese et son utilisation.
MXPA01007371A (es)	2002-06-05	Mcm-68 sintetica, porosa, cristalina, su sintesis y uso