EP0792928B1 - Procédé de récupération d'aromates à partir d'essence de reforming - Google Patents
Procédé de récupération d'aromates à partir d'essence de reforming Download PDFInfo
- Publication number
- EP0792928B1 EP0792928B1 EP96120033A EP96120033A EP0792928B1 EP 0792928 B1 EP0792928 B1 EP 0792928B1 EP 96120033 A EP96120033 A EP 96120033A EP 96120033 A EP96120033 A EP 96120033A EP 0792928 B1 EP0792928 B1 EP 0792928B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aromatics
- benzene
- hydrogenation
- extractive distillation
- distillation
- 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
- 238000000034 method Methods 0.000 title claims abstract description 37
- 230000008569 process Effects 0.000 title claims abstract description 21
- 238000011084 recovery Methods 0.000 title abstract 2
- 238000002407 reforming Methods 0.000 title description 5
- 238000000895 extractive distillation Methods 0.000 claims abstract description 56
- 238000000622 liquid--liquid extraction Methods 0.000 claims abstract description 12
- 238000000638 solvent extraction Methods 0.000 claims abstract description 12
- 150000001336 alkenes Chemical class 0.000 claims abstract description 9
- 150000001993 dienes Chemical class 0.000 claims abstract description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 186
- 238000005984 hydrogenation reaction Methods 0.000 claims description 61
- 239000002904 solvent Substances 0.000 claims description 43
- 238000004821 distillation Methods 0.000 claims description 23
- 239000003054 catalyst Substances 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 12
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 238000004508 fractional distillation Methods 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- -1 N-substituted-morpholine Chemical class 0.000 claims description 3
- 239000012876 carrier material Substances 0.000 claims description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 150000001346 alkyl aryl ethers Chemical group 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- 239000000047 product Substances 0.000 description 33
- 239000002253 acid Substances 0.000 description 26
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 24
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 24
- 229910052794 bromium Inorganic materials 0.000 description 24
- 238000000605 extraction Methods 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 12
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 238000004061 bleaching Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- SODQFLRLAOALCF-UHFFFAOYSA-N 1lambda3-bromacyclohexa-1,3,5-triene Chemical compound Br1=CC=CC=C1 SODQFLRLAOALCF-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 239000008096 xylene Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000001833 catalytic reforming Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 150000003738 xylenes Chemical class 0.000 description 4
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 3
- 239000010779 crude oil Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 238000011144 upstream manufacturing Methods 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
- 239000000446 fuel Substances 0.000 description 2
- 230000036571 hydration Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AFVDZBIIBXWASR-AATRIKPKSA-N (E)-1,3,5-hexatriene Chemical compound C=C\C=C\C=C AFVDZBIIBXWASR-AATRIKPKSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- WHDPTDWLEKQKKX-UHFFFAOYSA-N cobalt molybdenum Chemical compound [Co].[Co].[Mo] WHDPTDWLEKQKKX-UHFFFAOYSA-N 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- APPOKADJQUIAHP-UHFFFAOYSA-N hexa-2,4-diene Chemical class CC=CC=CC APPOKADJQUIAHP-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000010802 sludge Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
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
-
- 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
- C10G21/00—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents
-
- 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
- C10G7/00—Distillation of hydrocarbon oils
- C10G7/08—Azeotropic or extractive distillation
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)
- Catalysts (AREA)
Claims (6)
- Procédé pour l'obtention d'arômes purs à partir de reformat,
au cours duquel procédé, une étape de reformat est obtenue au cours d'une première étape du procédé à partir de reformat par distillation fractionnée avec un aromate d'un nombre de carbone sélectionné Cx ou à l'aide d'aromates de plusieurs nombres de carbone sélectionnés,
dans lequel l'étape de reformat est hydratée au cours d'une seconde étape du procédé de façon sélective avec du nickel ou du palladium sur un matériau support en tant que catalyseur d'hydratation et par conséquent, les conditions d'hydratation sont réglées de telle sorte que des non-aromates essentiellement soient notamment des oléfines, des dioléfines et des trioléfines, soient hydratées et par conséquent, les dioléfines et les trioléfines conjuguées soient hydratées, si possible, intégralement,
et au cours duquel procédé ensuite les produits hydratés de façon sélective contenant des aromates sont séparés au cours d'une troisième étape du procédé par distillation d'extraction et / ou par extraction liquide-liquide en des aromates et des non-aromates. - Procédé selon la revendication 1 dans lequel une étape de reformat est obtenue au cours d'une première étape du procédé, laquelle étape contient comme portion aromatique essentiellement du benzène.
- Procédé selon l'une quelconque des revendications 1 ou 2 au cours duquel la distillation extractive et / ou l'extraction liquide-liquide est réalisée à l'aide d'un solvant sélectif du groupe N-formylmorphine, N-méthylpyrrolidone, sulfolane, éthylène glycol ou de dérivés d'éthylène glycol.
- Procédé selon l'une quelconque des revendications 1 à 3, dans lequel une morpholine N-substituée comprenant 1 à 8 atomes de carbone est utilisée dans des substituants comme solvant sélectif.
- Procédé selon l'une quelconque des revendications 1 à 4, dans lequel les alcanes diols comprenant 2 à 5 atomes de carbone et / ou leurs éthers de mono et / ou dialkyle sont utilisés comme solvant sélectif.
- Procédé selon l'une quelconque des revendications 1 à 5, dans lequel les aromates purs sont séparés par distillation par le solvant sélectif au terme de la distillation extractive et / ou par extraction liquide-liquide.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19603901 | 1996-02-03 | ||
| DE19603901A DE19603901A1 (de) | 1996-02-03 | 1996-02-03 | Verfahren zur Gewinnung von Reinaromaten aus Reformatbenzin und Vorrichtung zur Durchführung des Verfahrens |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0792928A2 EP0792928A2 (fr) | 1997-09-03 |
| EP0792928A3 EP0792928A3 (fr) | 1998-04-01 |
| EP0792928B1 true EP0792928B1 (fr) | 2004-03-17 |
Family
ID=7784424
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP96120033A Expired - Lifetime EP0792928B1 (fr) | 1996-02-03 | 1996-12-13 | Procédé de récupération d'aromates à partir d'essence de reforming |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6124514A (fr) |
| EP (1) | EP0792928B1 (fr) |
| JP (1) | JP4514839B2 (fr) |
| KR (1) | KR970061835A (fr) |
| AT (1) | ATE262020T1 (fr) |
| CA (1) | CA2196585A1 (fr) |
| CZ (1) | CZ25097A3 (fr) |
| DE (2) | DE19603901A1 (fr) |
| ES (1) | ES2217298T3 (fr) |
| PL (1) | PL318211A1 (fr) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010102712A2 (fr) | 2009-03-11 | 2010-09-16 | Uhde Gmbh | Procédé de préparation de composés aromatiques purs a partir de fractions d'hydrocarbure renfermant des composés aromatiques |
| WO2011082993A1 (fr) | 2009-12-15 | 2011-07-14 | Basf Se | Procédé d'hydrogénation en phase gazeuse d'un courant d'hydrocarbures qui contient des composants polymérisables dans des conditions réactionnelles de l'hydrogénation en phase gazeuse |
| DE102010051396A1 (de) | 2010-11-16 | 2012-05-16 | Thyssenkrupp Uhde Gmbh | Verfahren zur Entfernung schwersiedender Kohlenwasserstoffe aus Lösungsmittelströmen |
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| US2960548A (en) * | 1958-09-19 | 1960-11-15 | Pure Oil Co | Extraction of aromatics from hydrocarbon fractions |
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-
1996
- 1996-02-03 DE DE19603901A patent/DE19603901A1/de not_active Withdrawn
- 1996-12-13 AT AT96120033T patent/ATE262020T1/de active
- 1996-12-13 EP EP96120033A patent/EP0792928B1/fr not_active Expired - Lifetime
- 1996-12-13 ES ES96120033T patent/ES2217298T3/es not_active Expired - Lifetime
- 1996-12-13 DE DE59610939T patent/DE59610939D1/de not_active Expired - Lifetime
-
1997
- 1997-01-28 CZ CZ97250A patent/CZ25097A3/cs unknown
- 1997-01-30 PL PL97318211A patent/PL318211A1/xx unknown
- 1997-01-31 JP JP01929297A patent/JP4514839B2/ja not_active Expired - Fee Related
- 1997-01-31 CA CA002196585A patent/CA2196585A1/fr not_active Abandoned
- 1997-01-31 KR KR1019970002925A patent/KR970061835A/ko not_active Withdrawn
- 1997-01-31 US US08/791,893 patent/US6124514A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010102712A2 (fr) | 2009-03-11 | 2010-09-16 | Uhde Gmbh | Procédé de préparation de composés aromatiques purs a partir de fractions d'hydrocarbure renfermant des composés aromatiques |
| DE102009012265A1 (de) | 2009-03-11 | 2010-09-23 | Uhde Gmbh | Verfahren zur Gewinnung von Reinaromaten aus aromatenhaltigen Kohlenwasserstofffraktionen |
| WO2011082993A1 (fr) | 2009-12-15 | 2011-07-14 | Basf Se | Procédé d'hydrogénation en phase gazeuse d'un courant d'hydrocarbures qui contient des composants polymérisables dans des conditions réactionnelles de l'hydrogénation en phase gazeuse |
| DE102010051396A1 (de) | 2010-11-16 | 2012-05-16 | Thyssenkrupp Uhde Gmbh | Verfahren zur Entfernung schwersiedender Kohlenwasserstoffe aus Lösungsmittelströmen |
| WO2012065703A1 (fr) | 2010-11-16 | 2012-05-24 | Thyssenkrupp Uhde Gmbh | Procédé pour l'élimination d'hydrocarbures à point d'ébullition élevé de courants de solvants |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH09309846A (ja) | 1997-12-02 |
| KR970061835A (ko) | 1997-09-12 |
| DE59610939D1 (de) | 2004-04-22 |
| PL318211A1 (en) | 1997-08-04 |
| EP0792928A2 (fr) | 1997-09-03 |
| JP4514839B2 (ja) | 2010-07-28 |
| DE19603901A1 (de) | 1997-08-07 |
| ES2217298T3 (es) | 2004-11-01 |
| ATE262020T1 (de) | 2004-04-15 |
| EP0792928A3 (fr) | 1998-04-01 |
| CA2196585A1 (fr) | 1997-08-04 |
| US6124514A (en) | 2000-09-26 |
| CZ25097A3 (en) | 1997-08-13 |
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