DE2659105A1 - Katalytisches hydrierungs-dreistufenverfahren - Google Patents
Katalytisches hydrierungs-dreistufenverfahrenInfo
- Publication number
- DE2659105A1 DE2659105A1 DE19762659105 DE2659105A DE2659105A1 DE 2659105 A1 DE2659105 A1 DE 2659105A1 DE 19762659105 DE19762659105 DE 19762659105 DE 2659105 A DE2659105 A DE 2659105A DE 2659105 A1 DE2659105 A1 DE 2659105A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- weight
- percent
- product
- stage
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 32
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title description 2
- 239000003054 catalyst Substances 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 12
- 229930195733 hydrocarbon Natural products 0.000 claims description 12
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000004215 Carbon black (E152) Substances 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 238000005984 hydrogenation reaction Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910000510 noble metal Inorganic materials 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910017052 cobalt Inorganic materials 0.000 claims description 4
- 239000010941 cobalt Substances 0.000 claims description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 4
- 238000000197 pyrolysis Methods 0.000 claims description 4
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052721 tungsten Inorganic materials 0.000 claims description 4
- 239000010937 tungsten Substances 0.000 claims description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052750 molybdenum Inorganic materials 0.000 claims description 3
- 239000011733 molybdenum Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 26
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 14
- 230000003197 catalytic effect Effects 0.000 description 14
- 239000000126 substance Substances 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
- 238000004064 recycling Methods 0.000 description 8
- -1 alkenyl aromatic Hydrocarbons Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- 230000000295 complement effect Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000004939 coking Methods 0.000 description 3
- 230000009849 deactivation Effects 0.000 description 3
- 239000000446 fuel Substances 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000004230 steam cracking Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KBJMLQFLOWQJNF-UHFFFAOYSA-N nickel(ii) nitrate Chemical compound [Ni+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O KBJMLQFLOWQJNF-UHFFFAOYSA-N 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 125000005595 acetylacetonate group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- 239000004058 oil shale Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003348 petrochemical agent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 229910001930 tungsten oxide 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
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/44—Hydrogenation of the aromatic hydrocarbons
- C10G45/46—Hydrogenation of the aromatic hydrocarbons characterised by the catalyst used
- C10G45/52—Hydrogenation of the aromatic hydrocarbons characterised by the catalyst used containing platinum group metals or compounds thereof
-
- 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
- C10G65/00—Treatment of hydrocarbon oils by two or more hydrotreatment processes only
- C10G65/02—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only
- C10G65/04—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7600202A FR2337195A1 (fr) | 1976-01-05 | 1976-01-05 | Procede de traitement catalytique, en trois etapes, sous pression d'hydrogene de coupes lourdes tres fortement insaturees |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2659105A1 true DE2659105A1 (de) | 1977-07-14 |
| DE2659105C2 DE2659105C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-21 |
Family
ID=9167660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762659105 Granted DE2659105A1 (de) | 1976-01-05 | 1976-12-28 | Katalytisches hydrierungs-dreistufenverfahren |
Country Status (9)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2806854C2 (de) * | 1978-02-17 | 1986-01-02 | Linde Ag, 6200 Wiesbaden | Verfahren zum thermischen Spalten von Kohlenwasserstoffen zu Olefinen |
| DE2840986C2 (de) * | 1978-09-21 | 1987-03-26 | Linde Ag, 6200 Wiesbaden | Verfahren zur Aufarbeitung der bei der Spaltung von Kohlenwasserstoffen entstehenden über 200 °C siedenden Kohlenwasserstoff-Fraktionen |
| US4243519A (en) * | 1979-02-14 | 1981-01-06 | Exxon Research & Engineering Co. | Hydrorefining process |
| JPS58109592A (ja) * | 1981-12-22 | 1983-06-29 | アトランテイツク・リツチフイ−ルド・カンパニ− | 潤滑油の粘度を有する鉱物性炭化水素油から白鉱油を製造する方法 |
| DE3232395A1 (de) * | 1982-08-31 | 1984-03-01 | Linde Ag, 6200 Wiesbaden | Verfahren zur herstellung von olefinen |
| JPH01294796A (ja) * | 1988-05-23 | 1989-11-28 | Agency Of Ind Science & Technol | 化石燃料油の多段式水素化分解方法 |
| JP3187104B2 (ja) * | 1991-07-19 | 2001-07-11 | 日石三菱株式会社 | 低硫黄ディーゼル軽油の製造方法 |
| FR2729968B1 (fr) * | 1995-01-27 | 1997-04-11 | Inst Francais Du Petrole | Procede d'hydrogenation des diolefines et eventuellement des olefines de coupes hydrocarbures riches en composes aromatiques sur des catalyseurs metalliques impregenes de composes organiques soufres |
| DE19504595A1 (de) * | 1995-02-11 | 1996-08-14 | Basf Ag | Verfahren zur gemeinsamen Hydrierung von kohlenwasserstoffhaltigen Gasen und Kondensaten |
| DE69604407T2 (de) * | 1995-07-13 | 2000-05-11 | Engelhard De Meern B.V., De Meern | Hydrierung von thiofenische schwefel enthaltenden kohlenwasserstoffeinsätzen |
| US6821412B1 (en) | 1999-08-30 | 2004-11-23 | Cosmo Oil Co., Ltd. | Catalyst for hydrotreating of gas oil and method for hydrotreating of gas oil |
| FR2840620B1 (fr) * | 2002-06-07 | 2004-07-30 | Inst Francais Du Petrole | Procede de production d'hydrocarbures a faible teneur en soufre et en azote |
| US7597795B2 (en) * | 2003-11-10 | 2009-10-06 | Exxonmobil Research And Engineering Company | Process for making lube oil basestocks |
| US7816299B2 (en) * | 2003-11-10 | 2010-10-19 | Exxonmobil Research And Engineering Company | Hydrotreating catalyst system suitable for use in hydrotreating hydrocarbonaceous feedstreams |
| US20050109679A1 (en) * | 2003-11-10 | 2005-05-26 | Schleicher Gary P. | Process for making lube oil basestocks |
| JP7006685B2 (ja) * | 2017-04-18 | 2022-02-10 | 三菱瓦斯化学株式会社 | インダンカルボアルデヒドの製造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161586A (en) * | 1962-12-21 | 1964-12-15 | Universal Oil Prod Co | Hydrorefining of coke-forming hydrocarbon distillates |
| FR2197967B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-09-01 | 1975-01-03 | Inst Francais Du Petrole | |
| FR2240905B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-08-16 | 1980-01-04 | Inst Francais Du Petrole |
-
1976
- 1976-01-05 FR FR7600202A patent/FR2337195A1/fr active Granted
- 1976-12-28 DE DE19762659105 patent/DE2659105A1/de active Granted
- 1976-12-29 JP JP51160785A patent/JPS591431B2/ja not_active Expired
- 1976-12-31 NL NL7614638A patent/NL7614638A/xx not_active Application Discontinuation
-
1977
- 1977-01-04 IT IT19023/77A patent/IT1074375B/it active
- 1977-01-04 CA CA269,107A patent/CA1086673A/fr not_active Expired
- 1977-01-04 BE BE1007857A patent/BE850064A/xx not_active IP Right Cessation
- 1977-01-05 GB GB192/77A patent/GB1525361A/en not_active Expired
- 1977-12-20 US US05/862,324 patent/US4145276A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5285109A (en) | 1977-07-15 |
| CA1086673A (fr) | 1980-09-30 |
| FR2337195B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-03-06 |
| GB1525361A (en) | 1978-09-20 |
| FR2337195A1 (fr) | 1977-07-29 |
| BE850064A (fr) | 1977-07-04 |
| IT1074375B (it) | 1985-04-20 |
| NL7614638A (nl) | 1977-07-07 |
| JPS591431B2 (ja) | 1984-01-12 |
| US4145276A (en) | 1979-03-20 |
| DE2659105C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1987-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8126 | Change of the secondary classification |
Free format text: C10G 45/06 C10G 45/08 C10G 45/10 C10G 45/48 C10G 45/50 C10G 45/52 |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |