EP2707462A2 - Procédé de production de coupes kérosène ou gazole a partir d'une charge oléfinique ayant majoritairement de 4 a 6 atomes de carbone faisant appel a deux unités d'oligomérisation - Google Patents
Procédé de production de coupes kérosène ou gazole a partir d'une charge oléfinique ayant majoritairement de 4 a 6 atomes de carbone faisant appel a deux unités d'oligomérisationInfo
- Publication number
- EP2707462A2 EP2707462A2 EP12713203.3A EP12713203A EP2707462A2 EP 2707462 A2 EP2707462 A2 EP 2707462A2 EP 12713203 A EP12713203 A EP 12713203A EP 2707462 A2 EP2707462 A2 EP 2707462A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- carbon atoms
- oligomerization
- predominantly
- cut
- zsm
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 125000004432 carbon atom Chemical group C* 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 25
- 150000001336 alkenes Chemical class 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 239000003350 kerosene Substances 0.000 title claims description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title abstract 2
- 238000000746 purification Methods 0.000 claims abstract description 16
- 239000002808 molecular sieve Substances 0.000 claims abstract description 8
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000006384 oligomerization reaction Methods 0.000 claims description 68
- 239000003054 catalyst Substances 0.000 claims description 23
- 239000010457 zeolite Substances 0.000 claims description 20
- 239000003502 gasoline Substances 0.000 claims description 19
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 16
- 229910021536 Zeolite Inorganic materials 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Chemical class [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 150000004645 aluminates Chemical class 0.000 claims description 3
- 229910001657 ferrierite group Inorganic materials 0.000 claims description 3
- 229910052680 mordenite Inorganic materials 0.000 claims description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 2
- 229910004298 SiO 2 Inorganic materials 0.000 claims description 2
- 239000002283 diesel fuel Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 8
- 229930195733 hydrocarbon Natural products 0.000 description 7
- 150000002430 hydrocarbons Chemical class 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 description 3
- 150000002830 nitrogen compounds Chemical class 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000004523 catalytic cracking Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000006471 dimerization reaction Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- -1 iso olefins Chemical class 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical class CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- 241000269350 Anura Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000755816 Homo sapiens Inactive rhomboid protein 1 Proteins 0.000 description 1
- 102100022420 Inactive rhomboid protein 1 Human genes 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 241000083552 Oligomeris Species 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical class CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000013844 butane Nutrition 0.000 description 1
- UNYSKUBLZGJSLV-UHFFFAOYSA-L calcium;1,3,5,2,4,6$l^{2}-trioxadisilaluminane 2,4-dioxide;dihydroxide;hexahydrate Chemical compound O.O.O.O.O.O.[OH-].[OH-].[Ca+2].O=[Si]1O[Al]O[Si](=O)O1.O=[Si]1O[Al]O[Si](=O)O1 UNYSKUBLZGJSLV-UHFFFAOYSA-L 0.000 description 1
- 229910052676 chabazite Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 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 1
- 238000009533 lab test Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 150000002897 organic nitrogen compounds Chemical class 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
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical class CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/02—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material
- C10G25/03—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents with ion-exchange material with crystalline alumino-silicates, e.g. molecular sieves
- C10G25/05—Removal of non-hydrocarbon compounds, e.g. sulfur 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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
-
- 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
- C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
- C10G25/003—Specific sorbent material, not covered by C10G25/02 or C10G25/03
-
- 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
- C10G50/00—Production of liquid hydrocarbon mixtures from lower carbon number hydrocarbons, e.g. by oligomerisation
-
- 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
- C10G57/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one cracking process or refining process and at least one other conversion process
- C10G57/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one cracking process or refining process and at least one other conversion process with polymerisation
-
- 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
- C10G67/06—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 a sorption process 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
- C10G69/126—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 polymerisation, e.g. oligomerisation
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1088—Olefins
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/20—Characteristics of the feedstock or the products
- C10G2300/201—Impurities
- C10G2300/202—Heteroatoms content, i.e. S, N, O, P
-
- 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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/40—Characteristics of the process deviating from typical ways of processing
- C10G2300/4006—Temperature
-
- 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
- C10G2400/04—Diesel 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/08—Jet fuel
Definitions
- the present invention is in the field of refining processes for converting an olefinic fraction having predominantly 4 to 6 carbon atoms in a so-called middle distillate cut having predominantly 10 to 20 carbon atoms.
- This middle distillate cut may be a kerosene cut or a diesel cut.
- the present invention uses a first purification step to remove the nitrogen compounds contained in the feed followed by two different oligomerization,
- a first oligomerization making it possible to essentially react the isoolefins and leading to a gasoline cut composed of isoolefins having predominantly from 8 to 10 carbon atoms, an excellent octane number which can be separated and recovered as such, and
- hydrocarbon cut (02) comprising at least partly hydrocarbons having a number of carbon atoms of between 6 and 10, of which at least 2% by weight of olefins, in the presence of at least one catalyst promoting the dimerization and alkylation reactions of the species present in the mixture resulting from said contacting,
- step b) a separation of the effluents from step b) into at least two slices of which:
- This patent does not describe any pretreatment step, in particular purification of the feedstock (01).
- Patent FR 2,887,555 describes a process for preparing a diesel cut from an olefinic C2 Cl 2 cut comprising the following steps:
- step 2) a separation of the product mixture obtained in step 1), in three sections, including an intermediate section with a final boiling point of between 200 and 220 ° C.
- This process therefore uses a very broad olefinic fraction as filler and uses two distinct oligomerizations. It does not mention the possibility of a pretreatment of said charge, including purification against any nitrogen compounds contained in said charge.
- the patents FR 2 871 167 and FR 2 871 168 describe processes for producing diesel fuel cut from gasoline cuts comprising a first step of separation of the normal and isoolef, the oligomerization step relating only to the normal olefins.
- the process according to the present invention does not require any prior separation of the normal and iso olefins.
- the process according to the present invention does not use any alkylation step and therefore does not require any BTX-type cutting.
- FIG. 1 represents a diagram of the process according to the invention using two distinct oligomerization units preceded by a step of purification of the charge on a capture mass.
- the process according to the present invention uses two distinct oligomerization units working on different catalysts and under different operating conditions.
- the process according to the invention can be defined as a process for producing an average distillate cut having predominantly from 12 to 25 carbon atoms from an olefinic feed having predominantly between 4 and 6 carbon atoms, comprising the following process: 'following steps:
- a second oligomerization step of the remaining effluents (that is to say effluents reduced by the gasoline cut extracted in the previous step) from the first oligomerization step carried out at a temperature greater than 120 ° C on an amorphous silico aluminate catalyst, or on a zeolite catalyst,
- the starting olefins cut must comprise a minimum of branched olefins, called isoolefins, minimum which can be set at 10% by weight and preferably at 20% by weight, relative to all olefms of the charge.
- the feed consists of a section of olefinic hydrocarbons containing from 3 to 8 carbon atoms, preferably from 4 to 6 carbon atoms. It contains from 20% to 100% of olefins, preferably from 20% to 80% of olefins, and more preferably from 40% to 60% of olefins.
- It can come from a fluidized catalytic cracking unit or a naphtha steam cracking unit, or an alcohol dehydration unit or a Fischer-Tropsch synthesis unit or other available sources. from refining or petrochemical units.
- the charge to be treated (1) is sent to a purification unit (PUR) using an adsorbent such as a molecular sieve (for example of the Na X or NaY type) working under the following operating conditions:
- PUR purification unit
- an adsorbent such as a molecular sieve (for example of the Na X or NaY type) working under the following operating conditions:
- adsorbents used in the purification unit include metal oxides such as aluminas, crystallized silico-aluminates such as zeolites (often called molecular sieves), or mixtures of these compounds.
- zeolite-based molecular sieves of the faujasite type are preferred.
- An example is the NaX zeolite, for example that marketed by Axens under the name SBE 13X.
- This purifying unit is mainly intended to eliminate the nitrogenous compounds contained in the feed and which constitute poisons with respect to the catalysts used in downstream oligomerization units.
- the effluent (2) of the purification unit (PUR) is sent in a first oligomerization step (OLG1) working at a temperature below 120 ° C on a silica-alumina catalyst.
- the oligomerization catalyst for the first oligomerization step (OLG1) is an amorphous catalyst based on silico-aluminate, preferably chosen from silica-aluminas and silica aluminas, and preferably silicified alumina.
- the mass ratio SiO 2 / Al 2 O 3 is between 0.05 and 10, and preferably between 0.2 and 1.
- a preferred catalyst is for example that marketed by AXENS under the name IP 811.
- the effluent (3) leaving the first oligomerization step (OLG1) is optionally sent to a separation unit (DISTl) for extracting a gasoline cut (3 ') with a good octane number and which can therefore join the gasoline pool (POOL). Part of this species (3 ') can also be directed to the oligomerization unit (OLG2).
- the effluent (3) of the first oligomerization step (OLG1), or the effluent (4) of the optional separation step (DIST1) when it exists, is sent to a second oligomerization step (OLG2) working at a temperature above 120 ° C,
- zeolitic type catalyst such as, for example, a catalyst containing a zeolite ZSM-5.
- the zeolite catalyst used in the second oligomerization step (OLG2) preferably comprises at least one zeolite selected from the group consisting of aluminosilicate zeolites having an overall Si / Al atomic ratio greater than 10 and a pores 8, 10 or 12MR.
- Said zeolite is even more preferably selected from the group consisting of zeolites: ferrierite, chabazite, zeolites Y and US-Y, ZSM-5, ZSM-12, NU-86, mordenite, ZSM-22, NU-10, ZBM-30, ZSM-11, ZSM-57, ZSM-35, ⁇ -2, ITQ-6 and IM-5, SAPO, taken alone or in admixture.
- said zeolite is selected from the group consisting of ferrierite zeolites, ZSM-5, Mordenite and ZSM-22, taken alone or as a mixture.
- the zeolite used is ZSM-5.
- the effluents (5) of the second oligomerization step (OLG2) are then separated in a separation unit (DIST2) from which at least 4 sections are extracted:
- raffinate corresponding to an LPG cut
- intermediate cut (7) which corresponds to a gasoline with a number of carbon atoms of between 5 and 10
- Example 1 Charge C5-C6 (LCN)
- the various beds are arranged in series.
- the filler used is a so-called light gasoline C5-C6 cut that comes from an FCC unit, under the name LCN (Light Cut Naphta).
- the charge has a density of 0.6548.
- It also contains organic nitrogen compounds totaling a content of 11.6 ppm by weight expressed as elemental nitrogen and 15 ppm by weight of elemental sulfur.
- the effluent of the first bed is sent integrally into the second bed carrying out the first oligomerization step (OLGl) in which the temperature is gradually raised between 60 ° C and 120 ° C, in order to keep constant the conversion of the iso-olefins into C5, between 80% and 85%
- the effluent from the second bed is sent integrally into the third bed carrying out the second oligomerization step (OLG2), in which the temperature is gradually raised between 150 ° C and 230 ° C, in order to keep the conversion of the olefins in C5 constant. between 75% and 80%.
- OLG2 second oligomerization step
- the effluent of the third stage is separated by distillation into four sections:
- the hydrogenation is carried out with a nickel catalyst at 180 ° C. under 50 bar of hydrogen with a VVH of 0.5 and a hydrogen flow rate of 50 NL / h and a feed rate of 48 g / h.
- the catalysts used in the OLG1 and OLG2 steps and the capture mass used in the PUR step are the same as in Example 1.
- the feedstock used is a C4 ex-catalytic cracking unit (FCC) feed to which a so-called light gasoline C5-C6 cut has been added from one FCC unit under the name LCN (Light Cut Naphtha).
- FCC C4 ex-catalytic cracking unit
- the pressure is maintained at 50 bars effective at room temperature.
- the effluent from the first bed is sent integrally into the second bed carrying out the first oligomerization step (OLG1), in which the temperature gradually increases between 50 ° C and 110 ° C, in order to keep the conversion of the iso-olefins constant.
- OLG1 first oligomerization step
- C5 between 80% and 85%.
- the effluent from the second bed is sent integrally into the third bed carrying out the second oligomerization step (OLG2), in which the temperature is gradually raised between 150 ° C and 230 ° C, in order to keep the conversion of the olefins in C5 constant. between 75% and 80%.
- OLG2 second oligomerization step
- the conversion of olefins to C4 is greater than 80%.
- the effluent of the third stage is separated by distillation into four sections:
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- 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)
- Crystallography & Structural Chemistry (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1101444A FR2975103B1 (fr) | 2011-05-12 | 2011-05-12 | Procede de production de coupes kerosene ou gazole a partir d'une charge olefinique ayant majoritairement de 4 a 6 atomes de carbone |
FR1102873A FR2975104B1 (fr) | 2011-05-12 | 2011-09-19 | Procede de production de coupes kerosene ou gazole a partir d'une charge olefinique ayant majoritairement de 4 a 6 atomes de carbone faisant appel a deux unites d'oligomerisation |
PCT/FR2012/000087 WO2012153010A2 (fr) | 2011-05-12 | 2012-03-13 | Procédé de production de coupes kérosène ou gazole a partir d'une charge oléfinique ayant majoritairement de 4 a 6 atomes de carbone faisant appel a deux unités d'oligomérisation |
Publications (2)
Publication Number | Publication Date |
---|---|
EP2707462A2 true EP2707462A2 (fr) | 2014-03-19 |
EP2707462B1 EP2707462B1 (fr) | 2016-06-08 |
Family
ID=45937406
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP12713204.1A Ceased EP2707461A2 (fr) | 2011-05-12 | 2012-03-13 | Procede de production de coupes kerosene ou gazole a partir d'une charge olefinique ayant majoritairement de 4 a 6 atomes de carbone |
EP12713203.3A Active EP2707462B1 (fr) | 2011-05-12 | 2012-03-13 | Procede production de coupes kerosene ou gazole a partir d'un charge olefinique ayant majoritairement de 4a 6 atomes de carbone faisant appel a deux unites d'oligomerisation |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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EP12713204.1A Ceased EP2707461A2 (fr) | 2011-05-12 | 2012-03-13 | Procede de production de coupes kerosene ou gazole a partir d'une charge olefinique ayant majoritairement de 4 a 6 atomes de carbone |
Country Status (4)
Country | Link |
---|---|
EP (2) | EP2707461A2 (fr) |
FR (2) | FR2975103B1 (fr) |
HU (1) | HUE030396T2 (fr) |
WO (2) | WO2012153011A2 (fr) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3134110A1 (fr) | 2022-04-05 | 2023-10-06 | Axens | Procédé amélioré de production de distillats moyens par oligomérisation d’une charge oléfinique |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3002770B1 (fr) * | 2013-03-04 | 2015-03-27 | IFP Energies Nouvelles | Procede de production de distillats moyens a partir d'une charge comprenant du butanol et du pentanol |
WO2014154803A1 (fr) * | 2013-03-28 | 2014-10-02 | Bp P.L.C. | Production d'une composition d'hydrocarbures issus du distillat moyen |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2547830B1 (fr) * | 1983-06-22 | 1988-04-08 | Inst Francais Du Petrole | Procede de production de supercarburant par polymerisation des coupes c4 |
JPH01259089A (ja) * | 1988-03-04 | 1989-10-16 | Res Assoc Util Of Light Oil | 重質油熱分解軽質留分の処理方法 |
DE69012295T2 (de) * | 1989-11-16 | 1995-01-05 | Mobil Oil Corp | Verfahren zur Qualitätserhöhung von Leichtolefinströmen. |
EP0734766B1 (fr) * | 1995-03-29 | 2001-08-29 | Koa Oil Company, Limited | Catalyseur pour l'oligomérisation des oléfines, procédé pour le préparer et procédé d'oligomérisation d'oléfines utilisant ledit catalyseur |
US6398946B1 (en) * | 1999-12-22 | 2002-06-04 | Chevron U.S.A., Inc. | Process for making a lube base stock from a lower molecular weight feedstock |
US20030136706A1 (en) * | 2001-10-25 | 2003-07-24 | Mcdaniel Stacey | Sulfur removal process |
FR2843969B1 (fr) | 2002-09-04 | 2007-03-23 | Inst Francais Du Petrole | Procede de valorisation d'une charge d'hydrocarbures et de diminution de la tension de vapeur de ladite charge |
FR2849051B1 (fr) * | 2002-12-23 | 2005-02-04 | Inst Francais Du Petrole | Procede de transformation d'hydrocarbures en une fraction presentant un indice d'octane ameliore et une fraction a fort indice de cetane |
FR2871167B1 (fr) * | 2004-06-04 | 2006-08-04 | Inst Francais Du Petrole | Procede d'amelioration de coupes essences et de transformation en gazoles |
FR2871168B1 (fr) | 2004-06-04 | 2006-08-04 | Inst Francais Du Petrole | Procede d'amelioration de coupes essences et de transformation en gazoles avec traitement complementaire permettant d'augmenter le rendement de la coupe gazole |
FR2873116B1 (fr) * | 2004-07-15 | 2012-11-30 | Inst Francais Du Petrole | Procede d'oligomerisation des olefines utilisant un catalyseur a base de silice-alumine |
US7473349B2 (en) * | 2004-12-30 | 2009-01-06 | Bp Corporation North America Inc. | Process for removal of sulfur from components for blending of transportation fuels |
FR2887555B1 (fr) | 2005-06-28 | 2009-06-26 | Inst Francais Du Petrole | Procede de preparation d'une coupe diesel par oligomerisation |
US7588738B2 (en) * | 2005-08-23 | 2009-09-15 | Exxonmobil Chemical Patents Inc. | Series catalyst beds |
EP1993980B1 (fr) * | 2006-03-10 | 2015-02-25 | ExxonMobil Chemical Patents Inc. | Diminution de la teneur en bases de lewis azotées pendant l'oligomérisation sur tamis moléculaire |
WO2011135206A1 (fr) | 2010-04-28 | 2011-11-03 | IFP Energies Nouvelles | Procede d'oligomerisation des olefines utilisant au moins un catalyseur organique possedant une forte densite de sites acides |
-
2011
- 2011-05-12 FR FR1101444A patent/FR2975103B1/fr active Active
- 2011-09-19 FR FR1102873A patent/FR2975104B1/fr active Active
-
2012
- 2012-03-13 HU HUE12713203A patent/HUE030396T2/hu unknown
- 2012-03-13 WO PCT/FR2012/000088 patent/WO2012153011A2/fr active Application Filing
- 2012-03-13 WO PCT/FR2012/000087 patent/WO2012153010A2/fr active Application Filing
- 2012-03-13 EP EP12713204.1A patent/EP2707461A2/fr not_active Ceased
- 2012-03-13 EP EP12713203.3A patent/EP2707462B1/fr active Active
Non-Patent Citations (1)
Title |
---|
See references of WO2012153010A2 * |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR3134110A1 (fr) | 2022-04-05 | 2023-10-06 | Axens | Procédé amélioré de production de distillats moyens par oligomérisation d’une charge oléfinique |
WO2023194337A1 (fr) | 2022-04-05 | 2023-10-12 | Axens | Procédé amélioré de production de distillats moyens par oligomérisation d'une charge oléfinique |
Also Published As
Publication number | Publication date |
---|---|
EP2707462B1 (fr) | 2016-06-08 |
WO2012153010A3 (fr) | 2013-01-03 |
HUE030396T2 (hu) | 2017-05-29 |
FR2975103B1 (fr) | 2014-08-29 |
EP2707461A2 (fr) | 2014-03-19 |
FR2975103A1 (fr) | 2012-11-16 |
WO2012153011A2 (fr) | 2012-11-15 |
WO2012153010A2 (fr) | 2012-11-15 |
WO2012153011A3 (fr) | 2013-01-03 |
FR2975104A1 (fr) | 2012-11-16 |
FR2975104B1 (fr) | 2015-03-20 |
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