CA2266003C - Procede de conversion d'hydrocarbures par traitement dans une zone de distillation associee a une zone reactionnelle et son utilisation en hydrogenation du benzene - Google Patents
Procede de conversion d'hydrocarbures par traitement dans une zone de distillation associee a une zone reactionnelle et son utilisation en hydrogenation du benzene Download PDFInfo
- Publication number
- CA2266003C CA2266003C CA002266003A CA2266003A CA2266003C CA 2266003 C CA2266003 C CA 2266003C CA 002266003 A CA002266003 A CA 002266003A CA 2266003 A CA2266003 A CA 2266003A CA 2266003 C CA2266003 C CA 2266003C
- Authority
- CA
- Canada
- Prior art keywords
- zone
- level
- distillation
- hydrogenation
- reaction
- 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 - Lifetime
Links
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 title claims abstract description 183
- 238000004821 distillation Methods 0.000 title claims abstract description 83
- 238000000034 method Methods 0.000 title claims abstract description 80
- 238000006243 chemical reaction Methods 0.000 title claims abstract description 65
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 25
- 150000002430 hydrocarbons Chemical class 0.000 title claims abstract description 25
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 51
- 238000010992 reflux Methods 0.000 title claims description 25
- 239000007788 liquid Substances 0.000 claims abstract description 62
- 239000001257 hydrogen Substances 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 40
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 15
- 230000003197 catalytic effect Effects 0.000 claims abstract description 14
- 238000005070 sampling Methods 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000007789 gas Substances 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 11
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 238000000605 extraction Methods 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 125000003118 aryl group Chemical group 0.000 description 15
- 238000010926 purge Methods 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 10
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 10
- 238000011084 recovery Methods 0.000 description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- 239000000446 fuel Substances 0.000 description 6
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical class CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 5
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 235000013844 butane Nutrition 0.000 description 5
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical class CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- 239000012188 paraffin wax Substances 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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 4
- 125000004836 hexamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000004088 simulation Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 125000004817 pentamethylene group Chemical class [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- 239000003570 air Substances 0.000 description 2
- 238000001833 catalytic reforming Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical class CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- AFCARXCZXQIEQB-UHFFFAOYSA-N N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CCNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 AFCARXCZXQIEQB-UHFFFAOYSA-N 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 239000012080 ambient air Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- -1 clays Substances 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000009928 pasteurization Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000006552 photochemical reaction Methods 0.000 description 1
- 229910001404 rare earth metal oxide Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000066 reactive distillation Methods 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000010457 zeolite Substances 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
-
- 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
- C10G49/00—Treatment of hydrocarbon oils, in the presence of hydrogen or hydrogen-generating compounds, not provided for in a single one of groups C10G45/02, C10G45/32, C10G45/44, C10G45/58 or C10G47/00
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9804351 | 1998-04-06 | ||
| FR9804352A FR2777013B1 (fr) | 1998-04-06 | 1998-04-06 | Procede de conversion d'hydrocarbures par traitement dans une zone de distillation comprenant un reflux circulant, associee a une zone reactionnelle et son utilisation en hydrogenation du benzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2266003A1 CA2266003A1 (fr) | 1999-10-06 |
| CA2266003C true CA2266003C (fr) | 2009-06-23 |
Family
ID=9524985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002266003A Expired - Lifetime CA2266003C (fr) | 1998-04-06 | 1999-04-01 | Procede de conversion d'hydrocarbures par traitement dans une zone de distillation associee a une zone reactionnelle et son utilisation en hydrogenation du benzene |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6174428B1 (2) |
| EP (1) | EP0949316B1 (2) |
| JP (1) | JP4482837B2 (2) |
| CA (1) | CA2266003C (2) |
| DE (1) | DE69919061T2 (2) |
| ES (1) | ES2226301T3 (2) |
| FR (1) | FR2777013B1 (2) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1425196A (zh) | 1999-11-24 | 2003-06-18 | 霍尼韦尔国际公司 | 导电互连 |
| US6855853B2 (en) * | 2002-09-18 | 2005-02-15 | Catalytic Distillation Technologies | Process for the production of low benzene gasoline |
| FR2933987B1 (fr) | 2008-07-18 | 2010-08-27 | Inst Francais Du Petrole | Procede d'hydrogenation du benzene |
| US7910070B2 (en) * | 2008-12-09 | 2011-03-22 | Uop Llc | Process for reducing benzene concentration in reformate |
| FR2948380B1 (fr) * | 2009-07-21 | 2011-08-12 | Inst Francais Du Petrole | Procede de reduction selective de la teneur en benzene et en composes insatures legers de differentes coupes hydrocarbures |
| US8808533B2 (en) * | 2010-04-23 | 2014-08-19 | IFP Energies Nouvelles | Process for selective reduction of the contents of benzene and light unsaturated compounds of different hydrocarbon fractions |
| EP2277980B1 (fr) * | 2009-07-21 | 2018-08-08 | IFP Energies nouvelles | Procédé de réduction sélective de la teneur en benzène et en composés insatures legers de differentes coupes hydrocarbures |
| SG11201404461WA (en) | 2012-02-01 | 2014-09-26 | Saudi Arabian Oil Co | Catalytic reforming process and system for producing reduced benzene gasoline |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3926785A (en) * | 1971-11-01 | 1975-12-16 | Chevron Res | Integrated distillation and hydrodesulfurization process for jet fuel production |
| US4302356A (en) * | 1978-07-27 | 1981-11-24 | Chemical Research & Licensing Co. | Process for separating isobutene from C4 streams |
| US5073236A (en) * | 1989-11-13 | 1991-12-17 | Gelbein Abraham P | Process and structure for effecting catalytic reactions in distillation structure |
| US5258560A (en) * | 1992-06-22 | 1993-11-02 | Uop | Etherification of C5 -plus olefins by catalytic distillation |
| FR2743080B1 (fr) * | 1995-12-27 | 1998-02-06 | Inst Francais Du Petrole | Procede de reduction selective de la teneur en benzene et en composes insatures legers d'une coupe d'hydrocarbures |
-
1998
- 1998-04-06 FR FR9804352A patent/FR2777013B1/fr not_active Expired - Lifetime
-
1999
- 1999-03-25 DE DE69919061T patent/DE69919061T2/de not_active Expired - Lifetime
- 1999-03-25 EP EP99400740A patent/EP0949316B1/fr not_active Expired - Lifetime
- 1999-03-25 ES ES99400740T patent/ES2226301T3/es not_active Expired - Lifetime
- 1999-04-01 CA CA002266003A patent/CA2266003C/fr not_active Expired - Lifetime
- 1999-04-05 US US09/285,777 patent/US6174428B1/en not_active Expired - Lifetime
- 1999-04-06 JP JP09850399A patent/JP4482837B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0949316A1 (fr) | 1999-10-13 |
| JP4482837B2 (ja) | 2010-06-16 |
| US6174428B1 (en) | 2001-01-16 |
| CA2266003A1 (fr) | 1999-10-06 |
| JPH11323353A (ja) | 1999-11-26 |
| ES2226301T3 (es) | 2005-03-16 |
| EP0949316B1 (fr) | 2004-08-04 |
| FR2777013A1 (fr) | 1999-10-08 |
| DE69919061T2 (de) | 2004-12-23 |
| DE69919061D1 (de) | 2004-09-09 |
| FR2777013B1 (fr) | 2000-05-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20190401 |