DE1470495B2 - Mehrstufiges hydrierverfahren fuer dampfgekrackte benzine - Google Patents
Mehrstufiges hydrierverfahren fuer dampfgekrackte benzineInfo
- Publication number
- DE1470495B2 DE1470495B2 DE19631470495 DE1470495A DE1470495B2 DE 1470495 B2 DE1470495 B2 DE 1470495B2 DE 19631470495 DE19631470495 DE 19631470495 DE 1470495 A DE1470495 A DE 1470495A DE 1470495 B2 DE1470495 B2 DE 1470495B2
- Authority
- DE
- Germany
- Prior art keywords
- hydrogenation
- resin
- nickel
- hydrogen
- catalyst
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 230000036571 hydration Effects 0.000 title 1
- 238000006703 hydration reaction Methods 0.000 title 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 41
- 238000005984 hydrogenation reaction Methods 0.000 claims description 39
- 239000003054 catalyst Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 34
- 239000007789 gas Substances 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 229910052759 nickel Inorganic materials 0.000 claims description 16
- 239000011347 resin Substances 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 16
- 150000001993 dienes Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000002430 hydrocarbons Chemical class 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 11
- 229930195733 hydrocarbon Natural products 0.000 claims description 11
- 150000005673 monoalkenes Chemical class 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 239000011593 sulfur Substances 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 5
- 238000004230 steam cracking Methods 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000005336 cracking Methods 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 6
- 239000000470 constituent Substances 0.000 claims 3
- 238000000926 separation method Methods 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims 2
- 238000007700 distillative separation Methods 0.000 claims 2
- 238000000605 extraction Methods 0.000 claims 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- 239000005977 Ethylene Substances 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 claims 1
- KYYSIVCCYWZZLR-UHFFFAOYSA-N cobalt(2+);dioxido(dioxo)molybdenum Chemical compound [Co+2].[O-][Mo]([O-])(=O)=O KYYSIVCCYWZZLR-UHFFFAOYSA-N 0.000 claims 1
- 150000001907 coumarones Chemical class 0.000 claims 1
- 230000001627 detrimental effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000003208 petroleum Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000009877 rendering Methods 0.000 claims 1
- 229930195734 saturated hydrocarbon Natural products 0.000 claims 1
- 238000010626 work up procedure Methods 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 230000009102 absorption Effects 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 229910000428 cobalt oxide Inorganic materials 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 6
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 6
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 6
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 3
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical compound CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 3
- 239000004113 Sepiolite Substances 0.000 description 3
- 229910052624 sepiolite Inorganic materials 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- ORMNPSYMZOGSSV-UHFFFAOYSA-N dinitrooxymercury Chemical compound [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004523 catalytic cracking Methods 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000003918 fraction a Anatomy 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-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
- C10G67/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only
- C10G67/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only
- C10G67/04—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one process for refining in the absence of hydrogen only plural serial stages only including solvent extraction as the refining step in the absence of hydrogen
- C10G67/0409—Extraction of unsaturated hydrocarbons
- C10G67/0427—The hydrotreatment being a selective hydrogenation of diolefins or acetylenes
-
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C7/00—Purification; Separation; Use of additives
- C07C7/148—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound
- C07C7/163—Purification; Separation; Use of additives by treatment giving rise to a chemical modification of at least one compound by hydrogenation
-
- 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
- C10G65/06—Treatment of hydrocarbon oils by two or more hydrotreatment processes only plural serial stages only including only refining steps at least one step being a selective hydrogenation of the diolefins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Analytical Chemistry (AREA)
- Water Supply & Treatment (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8773/62A GB979257A (en) | 1962-03-10 | 1962-03-10 | Multi-stage hydrogenation process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1470495A1 DE1470495A1 (de) | 1968-12-19 |
| DE1470495B2 true DE1470495B2 (de) | 1976-01-29 |
Family
ID=9859000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19631470495 Pending DE1470495B2 (de) | 1962-03-10 | 1963-03-06 | Mehrstufiges hydrierverfahren fuer dampfgekrackte benzine |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3190830A (en, 2012) |
| AT (1) | AT242839B (en, 2012) |
| BE (1) | BE629307A (en, 2012) |
| CS (1) | CS151428B2 (en, 2012) |
| DE (1) | DE1470495B2 (en, 2012) |
| DK (1) | DK113661B (en, 2012) |
| FR (1) | FR1352360A (en, 2012) |
| GB (1) | GB979257A (en, 2012) |
| LU (1) | LU43302A1 (en, 2012) |
| NL (1) | NL289907A (en, 2012) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3287259A (en) * | 1963-12-17 | 1966-11-22 | Exxon Research Engineering Co | Electrical insulating oil |
| GB1141809A (en) * | 1965-10-04 | 1969-02-05 | British Petroleum Co | Improvements relating to the desulphurisation and hydrogenation of aromatic hydrocarbons |
| US3428697A (en) * | 1966-07-21 | 1969-02-18 | Air Prod & Chem | Hydrogenation process |
| US3494859A (en) * | 1967-06-07 | 1970-02-10 | Universal Oil Prod Co | Two-stage hydrogenation of an aromatic hydrocarbon feedstock containing diolefins,monoolefins and sulfur compounds |
| US3511771A (en) * | 1967-07-24 | 1970-05-12 | Exxon Research Engineering Co | Integrated hydrofining,hydrodesulfurization and steam cracking process |
| GB1400884A (en) * | 1972-03-13 | 1975-07-16 | Ici Ltd | Treatment of the feedstock for a aromatic hydrocarbon extraction process |
| US4113603A (en) * | 1977-10-19 | 1978-09-12 | The Lummus Company | Two-stage hydrotreating of pyrolysis gasoline to remove mercaptan sulfur and dienes |
| US4392945A (en) * | 1982-02-05 | 1983-07-12 | Exxon Research And Engineering Co. | Two-stage hydrorefining process |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872492A (en) * | 1956-03-29 | 1959-02-03 | Universal Oil Prod Co | Production of aromatics in the presence of nitrogen compounds |
| US2953612A (en) * | 1958-03-03 | 1960-09-20 | American Oil Co | Catalytic hydrogenation of dripolene |
| US3004914A (en) * | 1958-07-25 | 1961-10-17 | British Petroleum Co | Catalysts and hydrogenation processes using the catalyst |
| GB899653A (en) * | 1958-07-25 | 1962-06-27 | British Petroleum Co | Improvements relating to the hydrogenation of gasolines |
| BE595962A (en, 2012) * | 1959-10-13 | |||
| BE599030A (en, 2012) * | 1960-01-14 | |||
| NL134684C (en, 2012) * | 1960-05-04 |
-
1962
- 1962-03-10 GB GB8773/62A patent/GB979257A/en not_active Expired
-
1963
- 1963-02-26 US US261224A patent/US3190830A/en not_active Expired - Lifetime
- 1963-02-28 DK DK92163AA patent/DK113661B/da unknown
- 1963-03-05 LU LU43302D patent/LU43302A1/xx unknown
- 1963-03-06 DE DE19631470495 patent/DE1470495B2/de active Pending
- 1963-03-07 AT AT179263A patent/AT242839B/de active
- 1963-03-07 CS CS1303A patent/CS151428B2/cs unknown
- 1963-03-07 FR FR927192A patent/FR1352360A/fr not_active Expired
- 1963-03-07 NL NL289907D patent/NL289907A/xx unknown
- 1963-03-07 BE BE629307D patent/BE629307A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT242839B (de) | 1965-10-11 |
| FR1352360A (fr) | 1964-02-14 |
| DK113661B (da) | 1969-04-14 |
| GB979257A (en) | 1965-01-01 |
| NL289907A (en, 2012) | 1965-06-10 |
| BE629307A (en, 2012) | 1963-10-21 |
| DE1470495A1 (de) | 1968-12-19 |
| LU43302A1 (en, 2012) | 1963-05-06 |
| CS151428B2 (en, 2012) | 1973-10-19 |
| US3190830A (en) | 1965-06-22 |
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