DE2366504C2 - Verfahren zum Hydroisomerisieren von Kohlenwasserstoffen an einem Katalysator, der Platin und/oder Palladium als hydrierungsaktive Metallkomponente auf oder in einem entkationisierten zeolithischen Träger enthält - Google Patents

Verfahren zum Hydroisomerisieren von Kohlenwasserstoffen an einem Katalysator, der Platin und/oder Palladium als hydrierungsaktive Metallkomponente auf oder in einem entkationisierten zeolithischen Träger enthält

Info

Publication number: DE2366504C2
Authority: DE; Germany
Prior art keywords: weight; sieve; zeolite; percent; catalyst
Prior art date: 1972-10-19
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

Application number

DE2366504A

Other languages

German (de)

English (en)

Inventor

Hans Uwe Houston Tex. Schutt

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.)

Shell Internationale Research Maatschappij BV

Original Assignee

Shell Internationale Research Maatschappij BV

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.)

1972-10-19

Filing date

1973-10-17

Publication date

1987-01-29

1972-10-19 Priority claimed from US298920A external-priority patent/US3864283A/en

1973-10-17 Application filed by Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV

1987-01-29 Application granted granted Critical

1987-01-29 Publication of DE2366504C2 publication Critical patent/DE2366504C2/de

Status Expired legal-status Critical Current

Links

239000003054 catalyst Substances 0.000 title claims description 57
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 title claims description 27
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims description 16
238000000034 method Methods 0.000 title claims description 15
229910052697 platinum Inorganic materials 0.000 title claims description 13
229930195733 hydrocarbon Natural products 0.000 title claims description 10
150000002430 hydrocarbons Chemical class 0.000 title claims description 10
229910052751 metal Inorganic materials 0.000 title claims description 10
239000002184 metal Substances 0.000 title claims description 10
229910052763 palladium Inorganic materials 0.000 title claims description 8
239000010457 zeolite Substances 0.000 claims description 60
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 48
229910021536 Zeolite Inorganic materials 0.000 claims description 47
239000000203 mixture Substances 0.000 claims description 28
239000011148 porous material Substances 0.000 claims description 24
229910052680 mordenite Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
239000003513 alkali Substances 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 5
239000012013 faujasite Substances 0.000 claims description 3
239000006069 physical mixture Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 13
239000000463 material Substances 0.000 description 12
238000006317 isomerization reaction Methods 0.000 description 11
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 8
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 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
239000004215 Carbon black (E152) Substances 0.000 description 5
239000007789 gas Substances 0.000 description 5
239000002245 particle Substances 0.000 description 5
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
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
229910052784 alkaline earth metal Inorganic materials 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000005342 ion exchange Methods 0.000 description 4
QWTDNUCVQCZILF-UHFFFAOYSA-N iso-pentane Natural products CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001354 calcination Methods 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000002195 synergetic effect Effects 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000001340 alkali metals Chemical class 0.000 description 2
150000001342 alkaline earth metals Chemical class 0.000 description 2
239000012876 carrier material Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000000320 mechanical mixture Substances 0.000 description 2
239000008188 pellet Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
239000010453 quartz Substances 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910000323 aluminium silicate Inorganic materials 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
ZCCIPPOKBCJFDN-UHFFFAOYSA-N calcium nitrate Chemical class [Ca+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ZCCIPPOKBCJFDN-UHFFFAOYSA-N 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000004523 catalytic cracking Methods 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000001833 catalytic reforming Methods 0.000 description 1
239000007806 chemical reaction intermediate Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000010960 commercial process Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
230000007423 decrease Effects 0.000 description 1
AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000009533 lab test Methods 0.000 description 1
238000011068 loading method Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
150000002736 metal compounds Chemical class 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000010970 precious metal Substances 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000001577 simple distillation Methods 0.000 description 1
239000002002 slurry Substances 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
- C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
- C10G47/10—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used with catalysts deposited on a carrier
- C10G47/12—Inorganic carriers
- C10G47/16—Crystalline alumino-silicate carriers
- 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
- B01J29/80—Mixtures of different zeolites
- 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
- 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
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2791—Catalytic processes with metals
- 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
- B01J2229/26—After treatment, characterised by the effect to be obtained to stabilize the total catalyst structure
- 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
- B01J2229/42—Addition of matrix or binder particles
- 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
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/084—Y-type faujasite
- 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
- B01J29/18—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the mordenite type
- 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
- B01J29/60—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the type L, as exemplified by patent document US3216789
- 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
- C10G2400/02—Gasoline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Oil, Petroleum & Natural Gas (AREA)
Inorganic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Materials Engineering (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)

DE2366504A 1972-10-19 1973-10-17 Verfahren zum Hydroisomerisieren von Kohlenwasserstoffen an einem Katalysator, der Platin und/oder Palladium als hydrierungsaktive Metallkomponente auf oder in einem entkationisierten zeolithischen Träger enthält Expired DE2366504C2 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US29889872A	1972-10-19	1972-10-19
US298920A US3864283A (en)	1972-10-19	1972-10-19	Hydrocarbon conversion catalyst

Publications (1)

Publication Number	Publication Date
DE2366504C2 true DE2366504C2 (de)	1987-01-29

Family

ID=26970933

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE2366504A Expired DE2366504C2 (de)	1972-10-19	1973-10-17	Verfahren zum Hydroisomerisieren von Kohlenwasserstoffen an einem Katalysator, der Platin und/oder Palladium als hydrierungsaktive Metallkomponente auf oder in einem entkationisierten zeolithischen Träger enthält

Country Status (1)

Country	Link
DE (1)	DE2366504C2 (nl)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1941948A1 (de) *	1968-08-19	1970-02-26	Shell Int Research	Verfahren zur Umwandlung von Kohlenwasserstoffen
US3507931A (en) *	1967-12-22	1970-04-21	Texaco Inc	Isomerization of paraffinic hydrocarbons in the presence of a mordenite catalyst
GB1189850A (en) *	1967-12-29	1970-04-29	Shell Int Research	Catalyst Manufacture by Controlled Calcination
US3527835A (en) *	1968-01-24	1970-09-08	Shell Oil Co	Hydroisomerization with mordenite catalyst prepared by competitive cationic exchange
US3549558A (en) *	1968-08-29	1970-12-22	Shell Oil Co	Crystalline alumino-silicate catalyst

1973
- 1973-10-17 DE DE2366504A patent/DE2366504C2/de not_active Expired

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3507931A (en) *	1967-12-22	1970-04-21	Texaco Inc	Isomerization of paraffinic hydrocarbons in the presence of a mordenite catalyst
GB1189850A (en) *	1967-12-29	1970-04-29	Shell Int Research	Catalyst Manufacture by Controlled Calcination
US3527835A (en) *	1968-01-24	1970-09-08	Shell Oil Co	Hydroisomerization with mordenite catalyst prepared by competitive cationic exchange
DE1941948A1 (de) *	1968-08-19	1970-02-26	Shell Int Research	Verfahren zur Umwandlung von Kohlenwasserstoffen
US3549558A (en) *	1968-08-29	1970-12-22	Shell Oil Co	Crystalline alumino-silicate catalyst

Legal Events

Date	Code	Title	Description
1982-07-15	AC	Divided out of	Ref country code: DE Ref document number: 2352156 Format of ref document f/p: P
1982-07-15	Q172	Divided out of (supplement):	Ref country code: DE Ref document number: 2352156
1982-12-09	8110	Request for examination paragraph 44
1986-03-27	8125	Change of the main classification	Ipc: C07C 15/02
1987-01-29	AC	Divided out of	Ref country code: DE Ref document number: 2352156 Format of ref document f/p: P
1987-01-29	D2	Grant after examination
1987-07-23	8364	No opposition during term of opposition

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DE2352156A1 (de)	1974-04-25	Verfahren zur herstellung eines kristallinen alumosilikat-zeolith-katalysators fuer kohlenwasserstoffumwandlungen, insbesondere fuer die hydrierende kohlenwasserstoffumwandlung und verwendung des auf diese weise hergestellten katalysators
DE1418009C3 (nl)	1973-10-31
DE2366504C2 (de)	1987-01-29	Verfahren zum Hydroisomerisieren von Kohlenwasserstoffen an einem Katalysator, der Platin und/oder Palladium als hydrierungsaktive Metallkomponente auf oder in einem entkationisierten zeolithischen Träger enthält