DE1468991C3 - Verfahren zum Isomerisieren von geradkettigen Kohlenwasserstoffen - Google Patents
Verfahren zum Isomerisieren von geradkettigen KohlenwasserstoffenInfo
- Publication number
- DE1468991C3 DE1468991C3 DE1468991A DE1468991A DE1468991C3 DE 1468991 C3 DE1468991 C3 DE 1468991C3 DE 1468991 A DE1468991 A DE 1468991A DE 1468991 A DE1468991 A DE 1468991A DE 1468991 C3 DE1468991 C3 DE 1468991C3
- Authority
- DE
- Germany
- Prior art keywords
- hydrogen
- mordenite
- ions
- aluminum
- isomerization
- 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
Links
- 238000000034 method Methods 0.000 title claims description 21
- 229930195733 hydrocarbon Natural products 0.000 title claims description 17
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 16
- 239000003054 catalyst Substances 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 37
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 229910052680 mordenite Inorganic materials 0.000 claims description 30
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 30
- 238000006317 isomerization reaction Methods 0.000 claims description 16
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 15
- 229910052697 platinum Inorganic materials 0.000 claims description 15
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 12
- 239000010457 zeolite Substances 0.000 claims description 11
- 229910021536 Zeolite Inorganic materials 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 6
- 229910001415 sodium ion Inorganic materials 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- -1 ammonium ions Chemical class 0.000 claims description 5
- 238000001354 calcination Methods 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000002441 X-ray diffraction Methods 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- 150000002500 ions Chemical class 0.000 claims 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 5
- 239000003513 alkali Substances 0.000 claims 4
- 229910052782 aluminium Inorganic materials 0.000 claims 4
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 claims 3
- YKTSYUJCYHOUJP-UHFFFAOYSA-N [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] Chemical compound [O--].[Al+3].[Al+3].[O-][Si]([O-])([O-])[O-] YKTSYUJCYHOUJP-UHFFFAOYSA-N 0.000 claims 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims 2
- 229910052710 silicon Inorganic materials 0.000 claims 2
- 239000010703 silicon Substances 0.000 claims 2
- 238000005727 Friedel-Crafts reaction Methods 0.000 claims 1
- 241001676573 Minium Species 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 229910000323 aluminium silicate Inorganic materials 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000004566 building material Substances 0.000 claims 1
- 229910052675 erionite Inorganic materials 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 60
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 26
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 4
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 4
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 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
- 150000001768 cations Chemical class 0.000 description 3
- 238000005336 cracking Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- AXCGVFCNSUNRML-UHFFFAOYSA-N butane;hexane Chemical compound CCCC.CCCCCC AXCGVFCNSUNRML-UHFFFAOYSA-N 0.000 description 2
- 229910052804 chromium Inorganic materials 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012013 faujasite Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012266 salt solution Substances 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 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 1
- HFGHRUCCKVYFKL-UHFFFAOYSA-N 4-ethoxy-2-piperazin-1-yl-7-pyridin-4-yl-5h-pyrimido[5,4-b]indole Chemical compound C1=C2NC=3C(OCC)=NC(N4CCNCC4)=NC=3C2=CC=C1C1=CC=NC=C1 HFGHRUCCKVYFKL-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001833 catalytic reforming Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 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
- 230000002265 prevention Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C07C5/27—Rearrangement of carbon atoms in the hydrocarbon skeleton
- C07C5/2767—Changing the number of side-chains
- C07C5/277—Catalytic processes
- C07C5/2775—Catalytic processes with crystalline alumino-silicates, e.g. molecular sieves
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US303126A US3190939A (en) | 1963-08-19 | 1963-08-19 | Paraffin isomerization process using hydrogen mordenite catalyst |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1468991A1 DE1468991A1 (de) | 1968-12-19 |
| DE1468991B2 DE1468991B2 (enExample) | 1973-11-22 |
| DE1468991C3 true DE1468991C3 (de) | 1974-06-20 |
Family
ID=23170657
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1468991A Expired DE1468991C3 (de) | 1963-08-19 | 1964-08-17 | Verfahren zum Isomerisieren von geradkettigen Kohlenwasserstoffen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3190939A (enExample) |
| BE (1) | BE651891A (enExample) |
| DE (1) | DE1468991C3 (enExample) |
| GB (1) | GB1012206A (enExample) |
| NL (1) | NL148294B (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE652145A (enExample) * | 1963-08-22 | 1900-01-01 | ||
| US3247098A (en) * | 1963-11-12 | 1966-04-19 | Exxon Research Engineering Co | Cracking a naphtha with a cracking conversion catalyst comprising a synthetic mordenite zeolite |
| US3299153A (en) * | 1964-05-06 | 1967-01-17 | Exxon Research Engineering Co | Naphthenic isomerization process with synthetic mordenite |
| US3280212A (en) * | 1964-08-18 | 1966-10-18 | Mobil Oil Corp | Conversion of hydrocarbons |
| US3301917A (en) * | 1964-09-22 | 1967-01-31 | Mobil Oil Corp | Upgrading of paraffinic hydrocarbons in the presence of a mixed aluminosilicate, platinum metal catalyst |
| US3376214A (en) * | 1965-09-28 | 1968-04-02 | Standard Oil Co | Hydroforming process with mordenite, alumina and platinum catalyst |
| ES347490A1 (es) * | 1966-12-05 | 1969-06-01 | British Petroleum Co | Un procedimiento para la produccion de cera microcristalinaflexible. |
| US3475345A (en) * | 1967-06-07 | 1969-10-28 | Shell Oil Co | Catalyst for paraffin isomerization |
| NL159635B (nl) * | 1967-09-29 | 1979-03-15 | Shell Int Research | Werkwijze voor het bereiden van mordeniet. |
| US3507931A (en) * | 1967-12-22 | 1970-04-21 | Texaco Inc | Isomerization of paraffinic hydrocarbons in the presence of a mordenite catalyst |
| US3923639A (en) * | 1968-04-18 | 1975-12-02 | Mobil Oil Corp | Converting hydrocarbons with zeolite ZSM-4 |
| US3914331A (en) * | 1970-12-23 | 1975-10-21 | Mobil Oil Corp | Disproportionation of aliphatic compounds |
| GB1386004A (en) * | 1971-02-11 | 1975-03-05 | Shell Int Research | Process for increasing the octane number of a light gasoline fraction |
| JPS568080B1 (enExample) * | 1971-04-23 | 1981-02-21 | ||
| US4146462A (en) * | 1978-05-19 | 1979-03-27 | Rustamov Musa I O | Hydroisomerization of gasoline fraction |
| US4238319A (en) * | 1979-04-23 | 1980-12-09 | Standard Oil Company (Indiana) | Process for isomerization of petroleum hydrocarbons |
| US4232181A (en) * | 1979-06-28 | 1980-11-04 | Norton Company | Hydroisomerization of pentane utilizing Pd exchanged mordenite |
| US4855530A (en) * | 1982-05-18 | 1989-08-08 | Mobil Oil Corporation | Isomerization process |
| JPH0692582B2 (ja) * | 1986-01-14 | 1994-11-16 | 住友金属鉱山株式会社 | 石炭液化方法 |
| US4992617A (en) * | 1989-01-03 | 1991-02-12 | Exxon Research And Engineering Company | Isomerization using noble metal acidic zeolites |
| US6194602B1 (en) * | 1998-04-16 | 2001-02-27 | Arco Chemical Technology, L.P. | Tertiary alkyl ester preparation |
| CZ307177B6 (cs) * | 2017-01-09 | 2018-02-21 | Ústav fyzikální chemie J. Heyrovského AV ČR, v. v. i. | Katalyzátor pro hydroizomerizaci alkanů C4-C7, jeho příprava a použití |
| CN113200554A (zh) * | 2021-05-07 | 2021-08-03 | 中国矿业大学 | 一种纳米丝光沸石分子筛及其制备方法与应用 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE608029A (enExample) * | 1957-02-05 | 1900-01-01 | ||
| US2971904A (en) * | 1957-02-12 | 1961-02-14 | Exxon Research Engineering Co | Petroleum process catalyst supported on a molecular sieve zeolite |
| US3039953A (en) * | 1958-09-17 | 1962-06-19 | Exxon Research Engineering Co | Selective conversion of normal paraffins with a crystalline zeolite |
| NL262738A (enExample) * | 1961-02-15 | 1900-01-01 | ||
| US3140253A (en) * | 1964-05-01 | 1964-07-07 | Socony Mobil Oil Co Inc | Catalytic hydrocarbon conversion with a crystalline zeolite composite catalyst |
-
1963
- 1963-08-19 US US303126A patent/US3190939A/en not_active Expired - Lifetime
-
1964
- 1964-08-17 BE BE651891D patent/BE651891A/xx unknown
- 1964-08-17 DE DE1468991A patent/DE1468991C3/de not_active Expired
- 1964-08-17 GB GB33541/64A patent/GB1012206A/en not_active Expired
- 1964-08-19 NL NL646409546A patent/NL148294B/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL148294B (nl) | 1976-01-15 |
| BE651891A (enExample) | 1965-02-17 |
| GB1012206A (en) | 1965-12-08 |
| DE1468991B2 (enExample) | 1973-11-22 |
| US3190939A (en) | 1965-06-22 |
| DE1468991A1 (de) | 1968-12-19 |
| NL6409546A (enExample) | 1965-02-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 |