EP1972678B1 - Procédé de désulfuration de fractions hydrocarbonées issues d'effluents de vapocraquage - Google Patents
Procédé de désulfuration de fractions hydrocarbonées issues d'effluents de vapocraquage Download PDFInfo
- Publication number
- EP1972678B1 EP1972678B1 EP08290204A EP08290204A EP1972678B1 EP 1972678 B1 EP1972678 B1 EP 1972678B1 EP 08290204 A EP08290204 A EP 08290204A EP 08290204 A EP08290204 A EP 08290204A EP 1972678 B1 EP1972678 B1 EP 1972678B1
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- EP
- European Patent Office
- Prior art keywords
- catalyst
- stage
- cut
- alkylation
- fraction
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 20
- 150000002430 hydrocarbons Chemical class 0.000 title claims description 16
- 238000004230 steam cracking Methods 0.000 title claims description 15
- 229930195733 hydrocarbon Natural products 0.000 title claims description 14
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims description 63
- 238000005804 alkylation reaction Methods 0.000 claims description 32
- 230000029936 alkylation Effects 0.000 claims description 30
- 238000004821 distillation Methods 0.000 claims description 27
- 150000003464 sulfur compounds Chemical class 0.000 claims description 24
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 239000011593 sulfur Substances 0.000 claims description 23
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 238000005984 hydrogenation reaction Methods 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- 239000011973 solid acid Substances 0.000 claims description 4
- 239000010457 zeolite Substances 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 2
- 230000003716 rejuvenation Effects 0.000 claims description 2
- 238000005342 ion exchange Methods 0.000 claims 2
- 239000000295 fuel oil Substances 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 25
- 239000001257 hydrogen Substances 0.000 description 12
- 229910052739 hydrogen Inorganic materials 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 11
- 238000000197 pyrolysis Methods 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 230000008569 process Effects 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 9
- 150000005673 monoalkenes Chemical class 0.000 description 9
- 150000001336 alkenes Chemical class 0.000 description 8
- 239000000446 fuel Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000003377 acid catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000001993 dienes Chemical class 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- 238000006477 desulfuration reaction Methods 0.000 description 3
- 230000023556 desulfurization Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000002485 combustion reaction Methods 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- -1 diolefins Chemical class 0.000 description 2
- 235000021183 entrée Nutrition 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052750 molybdenum Inorganic materials 0.000 description 2
- 239000011733 molybdenum Substances 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 150000003738 xylenes Chemical class 0.000 description 2
- YZUPZGFPHUVJKC-UHFFFAOYSA-N 1-bromo-2-methoxyethane Chemical compound COCCBr YZUPZGFPHUVJKC-UHFFFAOYSA-N 0.000 description 1
- BZYUMXXOAYSFOW-UHFFFAOYSA-N 2,3-dimethylthiophene Chemical compound CC=1C=CSC=1C BZYUMXXOAYSFOW-UHFFFAOYSA-N 0.000 description 1
- MNDZHERKKXUTOE-UHFFFAOYSA-N 2-butylthiophene Chemical compound CCCCC1=CC=CS1 MNDZHERKKXUTOE-UHFFFAOYSA-N 0.000 description 1
- JCCCMAAJYSNBPR-UHFFFAOYSA-N 2-ethylthiophene Chemical compound CCC1=CC=CS1 JCCCMAAJYSNBPR-UHFFFAOYSA-N 0.000 description 1
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical compound CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 1
- BTXIJTYYMLCUHI-UHFFFAOYSA-N 2-propylthiophene Chemical compound CCCC1=CC=CS1 BTXIJTYYMLCUHI-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical class SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- QENGPZGAWFQWCZ-UHFFFAOYSA-N Methylthiophene Natural products CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 1
- 101100412856 Mus musculus Rhod gene Proteins 0.000 description 1
- 241001080024 Telles Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 210000000540 fraction c Anatomy 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 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 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 230000009466 transformation Effects 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
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Images
Classifications
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- 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
- C10G67/08—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 acid treatment as the refining step in the absence of hydrogen
-
- 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
- C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
- C10G69/02—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only
- C10G69/12—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step
- C10G69/123—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural serial stages only including at least one polymerisation or alkylation step alkylation
-
- 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/205—Organic compounds not containing metal atoms by reaction with hydrocarbons added to the hydrocarbon oil
-
- 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
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
-
- 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
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
- C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
- C10G45/40—Selective hydrogenation of the diolefin or acetylene compounds 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
- C10G69/00—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process
- C10G69/14—Treatment of hydrocarbon oils by at least one hydrotreatment process and at least one other conversion process plural parallel stages only
-
- 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/02—Gasoline
Definitions
- the present invention relates to a process for treating hydrocarbon steam cracking effluents.
- the steam cracking process is a well-known petrochemical process, which is the basis for producing the major petrochemical intermediates, in particular ethylene and propylene.
- Steam cracking produces, in addition to ethylene and propylene, significant quantities of less valuable co-products, especially aromatic pyrolysis gasoline, which is found in significant quantities when cracking propane or butane, and even more so. , when you crack naphtha, diesel or even condensates.
- the aim of the invention is to find a technically simple and inexpensive solution to the aforementioned problem, in order to produce at the petrochemical site C7 + or C8 + or C9 + fractions from steam cracking units that can be used directly as a low sulfur gasoline base. .
- the patent US 6,048,451 describes how to desulphurize species from catalytic cracking by a process of converting the sulfur compounds to heavier sulfur compounds using an alkylating agent in the presence of an acid catalyst.
- the alkylating agent includes olefins or alcohols.
- this invention is described for application to catalytic cracking gasolines and is intended to increase the sulfur compounds of the thiophene and methylthiophene type.
- the invention therefore makes it possible, by departing from the conventional technical philosophy of reducing the sulfur of the pyrolysis gasolines by treatment under hydrogen, to produce low sulfur pyrolysis gasolines which can be used directly as a gasoline base and which have a high index. octane.
- steps a), b), c), and e) as described in this application are often present in petrochemical complexes equipped with steam cracking units.
- the investment required to produce pyrolysis gasolines depleted in sulfur is then weak since it consists only in the implementation of step d) of increasing the sulfur compounds.
- the charge is derived from one or more fractionations of steam cracking gasoline and corresponds to a section whose boiling point is generally between 0 ° C. and 250 ° C., preferably between 10 ° C. and 220 ° C.
- this feed consists essentially of CS-C11 with traces (a few wt%) of C3, C4, C12, C13, C14.
- This charge generally undergoes the selective hydrogenation step a) and the effluent from step a) is sent to step b).
- Step a) consists in bringing the charge to be treated into contact with hydrogen introduced in excess into one or more reactors containing a hydrogenation catalyst. The hydrogen flow rate is adjusted in order to dispose of it in sufficient quantity to theoretically hydrogenate all the diolefins, acetylenics and alkenyl aromatics and to maintain an excess of hydrogen at the reactor outlet.
- the selective hydrogenation step HD1 also known as the hydrodenialization step, is well known to those skilled in the art and is described in particular in the book Petrochemical Processes, Volume 1, Technip Edition, A. Chauvel and G. Lefebvre, pages 155-160 .
- the operating temperature during step a) is generally between 50 ° C. and 200 ° C.
- the space hourly speed is between 1 h -1 and 6 h -1
- the pressure is between 1.0 MPa. and 4.0 MPa.
- step a It is a fractionation step in one or more distillation columns of the feedstock or the effluent of step a) in order to produce at least one light cut consisting essentially of C5, an intermediate cut consisting essentially of C6 or C6-C7 or C6-C8 typically for the production of aromatics and a heavy cut consisting essentially of C7 + or C8 + or C9 + typically for the production of gasoline.
- the feedstock undergoes two successive distillations in order to produce the 3 cuts.
- the first distillation results in a light cut consisting essentially of C5 and a C6 + cut.
- the C6 + cut is sent to a second distillation column which leads to an intermediate cut consisting essentially of C6 or C6-C7 or C6-C8 for the production of aromatics and a heavy cut consisting essentially of C7 + or C8 + or C9 + intended for the production of gasoline.
- the feedstock firstly passes through a first distillation in order to obtain a light cut consisting essentially of C5 and a C6 + cut which is sent to step a).
- the effluent of step a) then undergoes distillation so as to obtain an intermediate cut consisting essentially of C6 or C6-C7 or C6-C8 intended for the production of aromatics and a heavy cut consisting essentially of C7 + or C8 + or C9 + for the production of gasoline.
- the intermediate cut is then sent to step c) hydrodesulphurization and deep hydrogenation while the heavy cut is sent to step d) alkylation.
- the effluent of the alkylation step d) is then sent to the distillation step e).
- Step c) comprises contacting the intermediate cut to be treated with hydrogen in one or more reactors containing hydrogenation and hydrodesulfurization catalyst.
- This step is also well known to those skilled in the art and is particularly described in the book Petrochemical Processes, Volume 1, Technip Edition, A. Chauvel and G. Lefebvre, page 160 .
- the operating temperature during stage c) is generally between 220 ° C. and 380 ° C.
- the space hourly speed is between 1 h -1 and 6 h -1
- the pressure is between 1.0 MPa. and 4.0 MPa.
- the alkylation step d) is a step of treatment of the C7 +, C8 + or C9 + heavy cut, and is mixed with a fraction of the C5 light cut consisting of an acid catalyst treatment which makes it possible to desulphurize the fraction of the said boiling cut. in gasoline without the addition of hydrogen by increasing the sulfur compounds.
- the feedstock treated in the alkylation step d) is a hydrocarbon fraction derived from a steam cracking unit. The charge corresponds to a C7 +, C8 + or C9 + cut pretreated in a hydrogenation unit HD1.
- the unit HD1 used in step a) is intended to selectively hydrogenate diolefins, acetylenes and a fraction of the alkenylaromatician.
- the filler is generally a mixture of olefinic, aromatic, paraffinic and naphthenic compounds as well as sulfur up to 20 ppm by weight at 1000 pm weight.
- the alkylation step d) is carried out in the alkylation section which may comprise one or more reactors.
- the main objective of step d) is to increase the sulfur compounds, by adding mono-olefins present in the feedstock.
- Sulfur compounds that can react are thiophene compounds of alkylthiophene type, and to a lesser extent mercaptan type compounds. These reactions do not involve any transformation of the aromatic compounds because these compounds have a much lower reactivity than the olefinic and sulfur compounds and are therefore not transformed, which is favorable to maintaining the octane number.
- alkylate alkylthiophenes whose alkyl groups contain 1 to 4 carbon atoms in particular alkylthiophenes of the ethylthiophene, dimethylthiophene, propylthiophene and butylthiophene type, with monoolefins comprising 7 or more carbon atoms and aromatic alkenyls.
- alkylthiophenes whose alkyl groups contain 1 to 4 carbon atoms
- monoolefins comprising 7 or more carbon atoms and aromatic alkenyls.
- the reactivity of the long olefins is lower than the reactivity of the short olefins, it may be advantageous to mix a feed containing butenes or pentenes with the feedstock.
- the alkylation step d) generally consists in bringing the fraction to be treated into contact with a solid acid catalyst under conditions of flow, temperature and pressure chosen to promote the addition of the monoolefins and alkenylaromatic compounds to the sulfur compounds.
- the heavy sulfur compounds thus formed generally have a boiling point higher than the typical end point of the gasoline, that is to say higher than 220 ° C. Typically, they can be separated from gasoline by simple distillation.
- the catalyst employed in the alkylation step d) is preferably a solid acid catalyst. Any catalyst capable of promoting the addition of unsaturated hydrocarbon compounds to the sulfur compounds can be used in the present invention.
- Zeolites, clays, functionalized silicas, silico-aluminates having acidity or grafted supports of acidic functional groups or acidic ion exchange resins are generally used.
- acidic ion exchange resins are used, most preferably polymeric acidic ion exchange resins such as sulfonic acid resins.
- the resins marketed by the company Rhom & Haas sounds the name of Amberlyst15, Amberlyst35 or Amberlyst 36 can be used. It is also possible to use the TA801 resin marketed by the company Axens.
- catalysts based on phosphoric acid as described in the patent US 6,736,963 obtained by the comalaxing of phosphoric acid and amorphous silica of kieselguhr type.
- acids based on inorganic oxides including aluminas, silica, silica aluminas and more particularly zeolites such as zeolites faujasites, mordenites, L, omega, X, Y, beta, ZSM-3, ZSM-4, ZSM-5, ZSM-18 and ZSM-20.
- the catalysts can also consist of a mixture of different acids of Lewis (e.g. BF4, BC13, SbF5 and AlCl3) with a non-zeolitic metal oxide such as silica, alumina, silica-aluminas.
- the operating temperature is generally adjusted according to the chosen catalyst, in order to reach the conversion rate of the desired sulfur compounds.
- the temperature is generally between 30 ° C and 300 ° C, and preferably between 40 ° C and 250 ° C.
- the temperature does not exceed 200 ° C and preferably 150 ° C to preserve the integrity of the catalyst.
- the temperature is greater than 100 ° C and less than 250 ° C, preferably greater than 140 ° C and less than 220 ° C.
- the volume of catalyst used is such that the ratio between the volume flow rate of the feedstock to be treated and the catalytic volume, also called the space hourly speed, is typically between 0.05 h -1 and 5 h -1 , preferably between 0, 07 h -1 and 3 h -1 and very preferably between 0.1 h -1 and 2 h -1 .
- the pressure is generally adjusted to maintain the reaction mixture in the liquid phase.
- the pressure is between 1.0 MPa and 4.0 MPa, preferably between 1.5 MPa and 4.0 MPa.
- the alkylation step d) is typically carried out in at least one fixed bed cylindrical reactor. However, it is preferable to have several reactors operated in series or in parallel in order to guarantee continuous operation despite deactivation of the catalyst. According to a preferred embodiment of the invention, the alkylation step is carried out in two identical reactors connected to each other, one being in operation while the other is stopped and loaded with fresh ready catalyst. to be used. This device makes it possible in particular to operate the unit continuously during the replacement phases or during the regeneration phases in situ of the spent catalyst.
- the alkylation step is carried out in 3 reactors which can be operated in parallel or in series.
- the feed successively feeds two reactors, one containing a partially spent catalyst, and the second containing fresh catalyst.
- the third reactor is left stationary, charged with fresh catalyst and ready for use.
- the catalyst of the first reactor is deactivated, the reactor is stopped, the second reactor is then operated in first position and the third reactor initially stopped is operated in second position.
- the first stopped reactor can then be discharged and its catalyst replaced with a batch of fresh catalyst.
- olefin dimerization reactions can occur in the reactor, resulting in an increase in the treated hydrocarbon fraction.
- the aromatic compounds are very little or not even converted in the reactor.
- the conversion of aromatics is less than 10%, preferably 5%, which allows to preserve the octane number of the cut.
- the alkylation reactions of sulfur compounds and of olefin dimerization are exothermic, that is, they are favored at low temperature and give off heat.
- the recycling rate defined as the recycled effluent flow divided by the fresh feed rate is typically between 0.2 and 4 and preferably between 0.5 and 2.
- the catalyst used is an ion exchange resin
- the charge is generally injected through the bottom of the reactor, at a linear velocity sufficient to cause suspension of the catalyst beads.
- This type of implementation has the advantage of limiting the temperature gradient in the reactor, that is to say the temperature difference between the outlet and the inlet of the reactor, and of ensuring a good distribution of the liquid hydrocarbon feedstock and good thermal homogeneity in the reactor.
- a system for supplementing / withdrawing the catalyst can be added to the reactor in order to continuously withdraw spent catalyst and make a supplement of fresh catalyst.
- an acid ion exchange resin catalyst is used because it is a catalyst which proves to be very active and which makes it possible to operate the reactor at a low temperature. That is to say at a temperature generally below 200 ° C, which is to limit the formation of gums and polymers which are easily formed products by condensation reaction of unsaturated compounds of polyolefin or alkenylaromatic type in the intermediate fractions of steam cracking.
- the space velocity (VVH) is adjusted to allow operation at the lowest temperature possible, compatible with the desired performance.
- the reactor can be operated at a VVH between 0.1 hr-1 and 2 hr-1 and a temperature below 80 ° C.
- the catalyst deactivates, it is necessary to gradually increase the temperature to maintain the performance. The temperature can then be increased gradually until it reaches generally 150 ° C. or even 200 ° C. maximum.
- a fraction of the C5 light cut is injected into the C7 +, C8 + or C9 + heavy cut and then sent to the alkylation step. This mixture makes it possible to increase the amount of reactive monoolefins and thus to promote the conversion of the sulfur compounds.
- step d) It is a step of distillation of the effluent of step d) intended to produce a light fraction that can be used directly as a gasoline base, and a C11 + or C12 + heavy fraction rich in sulfur compounds and used as an average or fuel distillate.
- the light fraction has an end point generally less than 230 ° C and preferably less than 220 ° C.
- the figure 1 presents a preferred embodiment of the invention.
- the feedstock is fed via line 1 and treated in a selective hydrogenation unit HD1 to carry out in particular a prior art alkenyl reduction and dedenization.
- the dedenized charge flows through line 2 and is fractionated in a distillation column 3 into a fraction C5 flowing through line 4, typically recycled to steam cracking or used as a gasoline base, and a C6 + fraction flowing in line 5.
- the C6-C n fraction feeds a hydrotreating unit HD2 which performs a thorough desulfurization of the C6-Cn cut and a deep hydrogenation of mono-olefins.
- a hydrotreating unit HD2 which performs a thorough desulfurization of the C6-Cn cut and a deep hydrogenation of mono-olefins.
- the LD145 / HR406 catalysts marketed by Axens can be used to carry out this step.
- the treated C6-Cn cut evacuated via line 10 may have, for example, less than 1 ppm by weight of sulfur and less than 50 ppm by weight of mono-olefins. It is generally sought to minimize the hydrogenation of the aromatics in this section in order to maximize their subsequent recovery for petrochemical applications.
- the cut C n + 1 + leaving the bottom of the column 7 by the line 9 feeds the section ALK said alkylation section to produce an alkylated cut recovered by the line 11.
- a fraction of the C5 cut from column 3 is injected via line 6 into the charge of the alkylation section to increase the amount of reactive olefins and thereby promote the conversion of sulfur compounds.
- the cut produced in the alkylation section ALK is sent via line 11 to a distillation column 12 to produce, at the top, a C n + 1 -C 12 cut recovered by the sulfur-depleted line 13 for use as a base gasoline, and in bottom a C12 + cut recovered by line 14 which can be used as domestic fuel and in which the alkylated sulfur compounds are concentrated in the alkylation section.
- the C n + 1 -C 12 cut recovered by line 13 generally contains less than 100 ppm of sulfur or even less than 50 pm of sulfur or for the purpose of the production of very low sulfur species, less than 10 ppm of sulfur.
- the figure 2 details a preferred embodiment of the alkylation step d).
- the alkylation section consists of two reactors R1 and R2 which can be operated in parallel.
- the mixture thus formed (line 9a) is sent to the reactor R1 via line 9b and the alkylation product is recovered via line 9d.
- the reactor R2 is charged with fresh and active catalyst and left stationary.
- the reactor R1 is stopped and the feedstock to be treated is sent to the reactor R2 via the line 9c.
- the alkylation product is recovered via line 9e.
- the catalyst contained in the reactor R1 is discharged and replaced with a fresh catalyst charge. This particular device makes it possible to maintain a continuous operation even when the catalyst is deactivated.
- Naphtech steam-cracking effluents are fractionated in a treatment plant for these effluents, comprising a primary distillation, to produce, in particular, an ⁇ -pyrrolysis gasoline cut, essentially comprising C5 and heavier hydrocarbons up to an ASTM endpoint of 210 ° C.
- This essence cut of pyrolysis ⁇ has the following characteristics: - Sulfur content: 200 ppm by weight - Composition of the pyrolysis gasoline fraction ⁇ (% by weight) C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 + Total n-paraffins 0.0 0.1 3.6 1.3 0.2 0.0 0.0 0.0 0.0 0.0 5.2 i-paraffins 0.0 2.7 1.4 0.3 0.4 0.1 0.0 0.0 0.0 4.9 monoolefins 0.2 0.6 5.3 1.7 0.7 1.0 0.4 0.3 1.0 0.9 12.1 diolefins 0.0 1.1 10.3 3.9 3.4 1.8 0.1 20.8 naphthenes 0.5 1.3 0.5 0.1 0.0 0.0 0.0 2.5 aromatics 26.6 11.8 4.2 2.0 1.9 0.7 0.1 47.3 aromatic alkenyls 3.5 3.1 0.5 0.0 0.0 7.1 Total 0.2 1.8 22.4 36.4 13.5 9.2 5.6 6.2 3.6 1.1 100.0
- This essence pyrolysis cut is treated according to the process scheme described in figure 1 .
- the product thus hydrotreated is distilled to separate the fractions C5, C6-C8 and C9 +.
- Gasoline ⁇ is then distilled in order to recover a first light fraction ⁇ 1 whose boiling range corresponds to the gasoline fraction, and a heavy fraction ⁇ 2.
- the end point of gasoline ⁇ 1 can be adjusted according to the essence specifications of each country.
- Gasoline ⁇ 1 can be incorporated directly into the low-sulfur gasoline pool.
- Gasoline ⁇ 2 can be used as domestic fuel.
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- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
Applications Claiming Priority (1)
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FR0701896A FR2913692B1 (fr) | 2007-03-14 | 2007-03-14 | Procede de desulfuration de fractions hydrocarbonees issues d'effluents de vapocraquage |
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EP1972678A1 EP1972678A1 (fr) | 2008-09-24 |
EP1972678B1 true EP1972678B1 (fr) | 2010-04-28 |
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EP08290204A Active EP1972678B1 (fr) | 2007-03-14 | 2008-02-27 | Procédé de désulfuration de fractions hydrocarbonées issues d'effluents de vapocraquage |
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US (1) | US7947166B2 (ja) |
EP (1) | EP1972678B1 (ja) |
JP (1) | JP5412044B2 (ja) |
KR (1) | KR101453091B1 (ja) |
CN (1) | CN101265421B (ja) |
BR (1) | BRPI0800628B1 (ja) |
DE (1) | DE602008001068D1 (ja) |
ES (1) | ES2343289T3 (ja) |
FR (1) | FR2913692B1 (ja) |
SG (1) | SG146554A1 (ja) |
TW (1) | TWI452129B (ja) |
Families Citing this family (10)
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FR2953854B1 (fr) * | 2009-12-16 | 2012-12-28 | Inst Francais Du Petrole | Procede de conversion de charges issues de sources renouvelables avec pretraitement des charges par dephosphatation a chaud |
CN102234540B (zh) * | 2010-05-07 | 2013-09-11 | 中国石油化工集团公司 | 一种裂解汽油中心馏分加氢方法和装置 |
CN102234541B (zh) * | 2010-05-07 | 2013-07-17 | 中国石油化工集团公司 | 一种裂解汽油全馏分加氢节能方法和装置 |
CN103074104B (zh) * | 2011-10-26 | 2015-11-25 | 中国石油化工股份有限公司 | 一种汽油加氢脱硫方法 |
MX358364B (es) * | 2012-08-21 | 2018-08-15 | Catalytic Distillation Tech | Hidrodesulfuración selectiva de gasolina de fcc menos de 100 ppm de azufre. |
US20150119613A1 (en) * | 2013-10-25 | 2015-04-30 | Uop Llc | Pyrolysis gasoline treatment process |
US9834494B2 (en) * | 2014-09-29 | 2017-12-05 | Uop Llc | Methods and apparatuses for hydrocarbon production |
EP3144369A1 (de) * | 2015-09-18 | 2017-03-22 | Linde Aktiengesellschaft | Verfahren und anlage zur trenntechnischen bearbeitung eines kohlenwasserstoffe und schwefelverbindungen enthaltenden stoffgemischs |
FR3103822B1 (fr) * | 2019-12-02 | 2022-07-01 | Ifp Energies Now | Procede de traitement d’huiles de pyrolyse de plastiques en vue de leur valorisation dans une unite de vapocraquage |
CN115948180B (zh) * | 2023-03-14 | 2023-05-23 | 新疆天利石化股份有限公司 | 一种裂解碳九加氢生产混合芳烃的节能环保工艺 |
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US2846464A (en) * | 1956-09-25 | 1958-08-05 | Exxon Research Engineering Co | Oxo synthesis of alcohols from heavy petroleum coking reaction |
DE1183072B (de) * | 1960-12-15 | 1964-12-10 | Bayer Ag | Verfahren zur thermischen Spaltung fluessiger Kohlenwasserstoffe zu Olefinen |
CA936821A (en) * | 1969-12-11 | 1973-11-13 | Kureha Kagaku Kogyo Kabushiki Kaisha | Process for treating by-product heavy fractions formed in the production of olefins |
US3838039A (en) * | 1971-12-14 | 1974-09-24 | Universal Oil Prod Co | Continuous conversion and regeneration process |
US5863419A (en) | 1997-01-14 | 1999-01-26 | Amoco Corporation | Sulfur removal by catalytic distillation |
US6048451A (en) * | 1997-01-14 | 2000-04-11 | Bp Amoco Corporation | Sulfur removal process |
US6059962A (en) * | 1998-09-09 | 2000-05-09 | Bp Amoco Corporation | Multiple stage sulfur removal process |
US6024865A (en) | 1998-09-09 | 2000-02-15 | Bp Amoco Corporation | Sulfur removal process |
US6736963B2 (en) * | 2001-07-31 | 2004-05-18 | Bp Corporation North America Inc. | Multiple stage process for removal of sulfur from components for blending of transportation fuels |
FR2835530B1 (fr) * | 2002-02-07 | 2004-04-09 | Inst Francais Du Petrole | Procede integre de desulfuration d'un effluent de craquage ou de vapocraquage d'hydrocarbures |
US6740789B1 (en) * | 2002-05-14 | 2004-05-25 | Uop Llc | Alkylaromatic process with catalyst regeneration |
FR2858981B1 (fr) * | 2003-08-19 | 2006-02-17 | Inst Francais Du Petrole | Procede de traitement d'une fraction intermediaire issue d'effluents de vapocraquage |
BRPI0607069B1 (pt) * | 2005-02-28 | 2015-06-30 | Exxonmobil Res & Eng Co | Método para produzir um produto de faixa de ebulição da gasolina |
-
2007
- 2007-03-14 FR FR0701896A patent/FR2913692B1/fr active Active
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2008
- 2008-02-27 ES ES08290204T patent/ES2343289T3/es active Active
- 2008-02-27 EP EP08290204A patent/EP1972678B1/fr active Active
- 2008-02-27 DE DE602008001068T patent/DE602008001068D1/de active Active
- 2008-03-10 SG SG200801978-8A patent/SG146554A1/en unknown
- 2008-03-11 TW TW097108568A patent/TWI452129B/zh not_active IP Right Cessation
- 2008-03-11 BR BRPI0800628A patent/BRPI0800628B1/pt not_active IP Right Cessation
- 2008-03-13 US US12/047,631 patent/US7947166B2/en active Active
- 2008-03-14 KR KR1020080023984A patent/KR101453091B1/ko active IP Right Grant
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Publication number | Publication date |
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US20080223753A1 (en) | 2008-09-18 |
ES2343289T3 (es) | 2010-07-27 |
TW200902702A (en) | 2009-01-16 |
FR2913692B1 (fr) | 2010-10-15 |
FR2913692A1 (fr) | 2008-09-19 |
BRPI0800628A (pt) | 2008-11-04 |
SG146554A1 (en) | 2008-10-30 |
US7947166B2 (en) | 2011-05-24 |
KR101453091B1 (ko) | 2014-10-27 |
TWI452129B (zh) | 2014-09-11 |
BRPI0800628B1 (pt) | 2017-03-14 |
KR20080084746A (ko) | 2008-09-19 |
JP5412044B2 (ja) | 2014-02-12 |
EP1972678A1 (fr) | 2008-09-24 |
DE602008001068D1 (de) | 2010-06-10 |
CN101265421A (zh) | 2008-09-17 |
CN101265421B (zh) | 2013-03-27 |
JP2008223027A (ja) | 2008-09-25 |
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