EP3455336A1 - Use of platforming process to isomerize light paraffins - Google Patents
Use of platforming process to isomerize light paraffinsInfo
- Publication number
- EP3455336A1 EP3455336A1 EP17796584.5A EP17796584A EP3455336A1 EP 3455336 A1 EP3455336 A1 EP 3455336A1 EP 17796584 A EP17796584 A EP 17796584A EP 3455336 A1 EP3455336 A1 EP 3455336A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- stream
- passing
- normal
- naphtha
- generate
- 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
- 238000000034 method Methods 0.000 title claims abstract description 42
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 54
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 53
- 238000002407 reforming Methods 0.000 claims abstract description 35
- 238000000926 separation method Methods 0.000 claims abstract description 35
- 238000005336 cracking Methods 0.000 claims abstract description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 38
- 150000001336 alkenes Chemical class 0.000 claims description 26
- 238000005194 fractionation Methods 0.000 claims description 26
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 21
- 238000000605 extraction Methods 0.000 claims description 21
- UAEPNZWRGJTJPN-UHFFFAOYSA-N Methylcyclohexane Natural products CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 14
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 12
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 10
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 8
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 6
- IJDNQMDRQITEOD-UHFFFAOYSA-N sec-butylidene Natural products CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 239000001294 propane Substances 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 17
- 239000005977 Ethylene Substances 0.000 description 17
- 239000010457 zeolite Substances 0.000 description 15
- 238000001179 sorption measurement Methods 0.000 description 12
- 238000009835 boiling Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 238000004519 manufacturing process Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 11
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 11
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- 229910021536 Zeolite Inorganic materials 0.000 description 9
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- -1 olefin hydrocarbons Chemical class 0.000 description 7
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 6
- 230000001965 increasing effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004523 catalytic cracking Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000001282 iso-butane Substances 0.000 description 3
- 235000013847 iso-butane Nutrition 0.000 description 3
- 238000005649 metathesis reaction Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910052680 mordenite Inorganic materials 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000004230 steam cracking Methods 0.000 description 3
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000005673 monoalkenes Chemical class 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 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
- 239000003575 carbonaceous material Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052676 chabazite Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000012013 faujasite Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 150000002910 rare earth metals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000002352 steam pyrolysis Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G61/00—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen
- C10G61/10—Treatment of naphtha by at least one reforming process and at least one process of refining in the absence of hydrogen processes also including other conversion steps
-
- 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
- C10G21/06—Refining of hydrocarbon oils, in the absence of hydrogen, by extraction with selective solvents characterised by the solvent used
- C10G21/12—Organic compounds only
- C10G21/14—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
- 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
- C10G35/00—Reforming naphtha
-
- 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
- C10G55/00—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process
- C10G55/02—Treatment of hydrocarbon oils, in the absence of hydrogen, by at least one refining process and at least one cracking process plural serial 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
- C10G63/00—Treatment of naphtha by at least one reforming process and at least one other conversion process
- C10G63/06—Treatment of naphtha by at least one reforming process and at least one other conversion process plural parallel stages only
- C10G63/08—Treatment of naphtha by at least one reforming process and at least one other conversion process plural parallel stages only including at least one cracking step
-
- 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
- C10G2300/1037—Hydrocarbon fractions
- C10G2300/1044—Heavy gasoline or naphtha having a boiling range of about 100 - 180 °C
-
- 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
- C10G2400/22—Higher 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
- C10G2400/00—Products obtained by processes covered by groups C10G9/00 - C10G69/14
- C10G2400/30—Aromatics
Definitions
- Ethylene and propylene, light olefin hydrocarbons with two or three atoms per molecule, respectively, are important chemicals for use in the production of other useful materials, such as polyethylene and polypropylene.
- Polyethylene and polypropylene are two of the most common plastics found in use today and have a wide variety of uses for both as a material fabrication and as a material for packaging.
- Other uses for ethylene and propylene include the production of vinyl chloride, ethylene oxide, ethylbenzene and alcohol.
- Steam cracking or pyrolysis of hydrocarbons produces essentially all of the ethylene and propylene.
- Hydrocarbons used as feedstock for light olefin production include natural gas, petroleum liquids, naphtha, and carbonaceous materials including coal, recycled plastics or any organic material.
- An ethylene plant is a very complex combination of reaction and gas recovery systems.
- the feedstock is charged to a cracking zone in the presence of steam at effective thermal conditions to produce a pyrolysis reactor effluent gas mixture.
- the pyrolysis reactor effluent gas mixture is stabilized and separated into purified components through a sequence of cryogenic and conventional fractionation steps.
- a typical ethylene separation section of an ethylene plant containing both cryogenic and conventional fractionation steps to recover an ethylene product with a purity exceeding 99.5% ethylene is described in an article by V. Kaiser and M. Picciotti, entitled, "Better Ethylene Separation Unit.” The article appeared in HYDROCARBON PROCESSING MAGAZINE, November 1988, pages 57-61 and is hereby incorporated by reference.
- the hydrocarbon feedstream to the zeolitic catalyst typically contains a mixture of 40 to 95 wt-% paraffins having 4 or more carbon atoms per molecule and 5 to 60 wt-% olefins having 4 or more carbon atoms per molecule.
- the preferred catalyst for such a zeolitic cracking process is an acid zeolite, examples includes several of the ZSM-type zeolites or the borosilicates. Of the ZSM-type zeolites, ZSM-5 was preferred.
- zeolites containing materials which could be used in the cracking process to produce ethylene and propylene included zeolite A, zeolite X, zeolite Y, zeolite ZK-5, zeolite ZK-4, synthetic mordenite, dealuminized mordenite, as well as naturally occurring zeolites including chabazite, faujasite, mordenite, and the like. Zeolites which were ion-exchanged to replace alkali metal present in the zeolite were preferred. Preferred cation exchange cations were hydrogen, ammonium, rare earth metals and mixtures thereof.
- European Patent No. 109,059B 1 discloses a process for the conversion of a feedstream containing olefins having 4 to 12 carbon atoms per molecule into propylene by contacting the feedstream with a ZSM-5 or a ZSM-1 1 zeolite having a silica to alumina atomic ratio less than or equal to 300 at a temperature from 400 to 600°C.
- the ZSM-5 or ZSM-1 1 zeolite is exchanged with a hydrogen or an ammonium cation.
- the reference also discloses that, although the conversion to propylene is enhanced by the recycle of any olefins with less than 4 carbon atoms per molecule, paraffins which do not react tend to build up in the recycle stream.
- the reference provides an additional oligomerization step wherein the olefins having 4 carbon atoms are oligomerized to facilitate the removal of paraffins such as butane and particularly isobutane which are difficult to separate from C4 olefins by conventional fractionation.
- a process is disclosed for the conversion of butenes to propylene. The process comprises contacting butenes with a zeolitic compound selected from the group consisting of silicalites, boralites, chromosilicates and those zeolites ZSM-5 and ZSM-11 in which the mole ratio of silica to alumina is greater than or equal to 350.
- the conversion is carried out at a temperature from 500 to 600°C. and at a space velocity of from 5 to 200 kg/hr of butenes per kg of pure zeolitic compound.
- European Patent 109060B1 discloses the use of silicalite-1 in an ion-exchanged, impregnated, or co-precipitated form with a modifying element selected from the group consisting of chromium, magnesium, calcium, strontium and barium.
- the heavier olefins having six or more carbon atoms per molecule which are produced in commercial ethylene plants are useful for the production of aromatic hydrocarbons.
- Portions of the olefin product include olefins with four carbon atoms per molecule. This portion includes both mono-olefins and di-olefins and some paraffins, including butane and iso-butane. Because the portion with four carbon atoms per molecule is generally less valuable and requires significant processing to separate di-olefins from the mono-olefins, processes are sought to improve the utilization of this portion of the ethylene plant product and enhancing the overall yield of ethylene and propylene.
- the present invention provides for a process to improve the yields of light olefins.
- a first embodiment of the invention is a process for improved naphtha cracking and reforming, comprising passing a naphtha feedstream to a naphtha splitter to generate a light naphtha and a heavy naphtha; passing the light naphtha to a separation unit to generate an extract stream comprising normal hydrocarbons, and a raffinate stream comprising non- normal hydrocarbons; passing the heavy naphtha to a reforming unit to generate a reformed effluent comprising aromatics, naphthenes and paraffins; and passing the extract stream to a cracking unit to generate a light olefin stream.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the reformed effluent to an aromatics extraction unit to generate an aromatics stream and an aromatics extraction raffinate stream comprising C5 and C6 paraffins.
- embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the aromatics extraction raffinate stream to the cracking unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the aromatics stream to an aromatics complex.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph wherein the adsorption separation unit uses a light desorbent having a boiling point lower than the lightest component in the feed.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph wherein the light desorbent is normal butane, normal pentane, propane or ethane.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph wherein the adsorption separation unit uses a heavy desorbent having a boiling point greater than the heaviest component in the feed.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph wherein the heavy desorbent is normal heptane, normal octane, normal nonane, normal decane, normal undecane or normal dodecane.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the raffinate stream to the reforming unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing a portion or all of the raffinate stream to an second fractionation column to generate a second overhead stream comprising iC5 and iC6, and a second bottoms stream comprising methyl cyclopentane, cyclohexane and benzene.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the raffinate stream to a second fractionation column to generate a second overhead stream comprising iC5, iC6, methyl cyclopentane, cyclohexane and benzene, and a second bottoms stream comprising cyclohexane and benzene.
- a second embodiment of the invention is a process for improved light olefin yields from naphtha, comprising passing a naphtha feedstream to a naphtha splitter to generate a light naphtha comprising C6 and lighter hydrocarbons and a heavy naphtha; passing the light naphtha to an adsorption separation unit to generate an extract stream comprising normal hydrocarbons, and a raffinate stream comprising non-normal
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the aromatics stream to an aromatics extraction unit to generate an aromatics stream and an extraction raffinate.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the raffinate stream to the reforming unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the raffinate stream to a fractionation unit to generate an overhead stream comprising isoparaffins having 5 and 6 carbons, and a bottoms stream comprising methyl cyclopentane, cyclohexane and benzene.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the bottoms stream to the reforming unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the overhead stream to a gasoline blending stock or to a reformer.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph wherein the adsorption separation unit uses a light desorbent.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph wherein the fractionation unit generates a bottoms stream, a side draw stream for passing to a gasoline blending stock, and an overhead stream for providing control over the Reid vapor pressure of the gasoline blending stock.
- Figure 1 is a diagram of the process to improve the quality of the feeds to a cracking unit and a reforming unit.
- the present invention is a process that improves flexibility in the operation of a refinery, and enables the refiner to readily shift product with minimal additional equipment.
- the operation of the new and existing equipment allows for shifting of production to increase higher value products as the market shifts.
- Market shifts include the price of raw materials, or oil, and the demand for different products such as precursor materials to plastics, such as light olefins or aromatics, or increased production of gasoline blending streams.
- Traditional processing of a naphtha feedstream is to only use the naphtha splitter, which segregates according to boiling point ranges.
- the present invention allows for increasing the normal hydrocarbon content to be passed to a cracking unit, while separating desirable aromatic to be passed to a reforming unit.
- n- hexane which is preferred for the steam cracker, has a very close boiling point to the benzene precursors (methylcyclohexane and cyclohexane) that are preferred for the reforming unit.
- the present invention is a process for improving the feeds to a naphtha cracking unit and a reforming unit, thereby increasing the efficiencies and yields of naphtha cracking units and reforming units.
- the process as shown in Figure 1, includes passing a naphtha feedstream 8 to a naphtha splitter 10 to generate a light naphtha 12 and a heavy naphtha 14.
- the light naphtha 12 is passed to a separation unit 20 to generate an extract stream 22 and a raffinate stream 24
- the extract stream 22 comprises normal hydrocarbons
- the raffinate stream 24 comprises non-normal hydrocarbons.
- the heavy naphtha 14 is passed to a reforming unit 30 to generate a reformed effluent stream 32 comprising aromatics naphthenes and paraffins.
- the extract stream 22 is passed to a cracking unit 40 to generate a light olefin stream 42.
- the process can further include passing the reformed effluent stream 32 to an aromatics extraction unit 50 to generate an aromatics stream 52 and an extraction raffinate stream 54.
- the extraction raffinate stream 54 includes C5 and C6 paraffins, and in particular, normal C5 and C6 paraffins.
- the aromatics stream 52 can be passed to an aromatics complex 60.
- the extraction raffinate stream 54 is passed to the cracking unit 40.
- the extraction raffinate stream 54 is passed to the adsorption separation unit 20.
- the raffinate stream 54 When the raffinate stream 54 is passed to the separation unit 20, it may be first hydrotreated, or passed to a hydrotreatment unit 80, before being passed to the separation unit 20.
- the hydrotreatment unit 80 can be used to hydrogenate olefins, or facilitate the removal of any sulfur that is obtained from the aromatics recovery unit 50.
- the separation unit 20 comprises an adsorption- separation unit that includes an adsorbent for preferentially adsorbing normal hydrocarbons to generate the extract stream 22 comprising normal hydrocarbons and the raffinate stream 24.
- the light naphtha 12 comprises n-C6 and lighter
- the heavy naphtha 14 comprises C6 aromatics, cyclohexane, and C7+ hydrocarbons.
- the naphtha splitter 12 can have the operating conditions altered to shift the separation, or split, of the naphtha feedstream 8.
- the naphtha splitter 10 is operated to generate a light naphtha 12 comprising iC6 and lighter hydrocarbons, and a heavy naphtha 14 comprises C6 aromatics and C7+ hydrocarbons.
- the adsorption- separation unit can use a light desorbent, or a heavy desorbent.
- a light desorbent the light desorbent is chosen to have a boiling point lower than the lightest component in the feed to the adsorption-separation unit 20.
- the desorbent has a boiling point lower than the lightest component in the light naphtha.
- Preferred desorbents for the light desorbent include normal butane, normal pentane, propane, or ethane, or even a mixture of light normal paraffins.
- the heavy desorbent is chosen to have a boiling point greater than the heaviest component in the light naphtha feed to the adsorption-separation unit 20.
- Preferred desorbents for the heavy desorbent include normal heptane, normal octane, normal nonane, normal decane, normal undecane or normal dodecane, or even a mixture of heavy normal paraffins.
- the process can further include passing the raffinate stream 24 to the reforming unit 30. While the raffinate stream 24 can contain lighter hydrocarbons, such as iC4, iC5 and iC6s, the reforming unit 30 will isomerize a portion of the lighter hydrocarbons to normal hydrocarbons, and these normal hydrocarbons can be sent to the cracking unit. By separating the light iso-paraffins from the normal paraffins in the light naphtha stream 12, one can improve the quality of the feed to the cracking unit and thereby improve the operating parameters.
- lighter hydrocarbons such as iC4, iC5 and iC6s
- the raffinate stream 24 is passed to a second fractionation column 70.
- the second fractionation column 70 can be a fractionation column to generate a second overhead stream 72 and a second bottoms stream 74.
- the second fractionation column can be operated to generate a second overhead stream 72 comprising iC5 and iC6 hydrocarbons, and a second bottoms stream having methyl cyclopentane, cyclohexane and benzene.
- the second fractionation column 70 can be operated to send methyl cyclopentane and some of the cyclohexane and benzene into the second overhead stream 72, with the second bottoms stream comprising cyclohexane and benzene in the bottoms stream 74.
- the second bottoms stream 74 can be passed to the reforming unit 30.
- the process is for improved light olefin yields from a naphtha feedstream.
- the naphtha feedstream is passed to a naphtha splitter to generate a light naphtha stream and a heavy naphtha stream.
- the heavy naphtha stream is passed to a reforming unit to generate a reformate stream, comprising aromatics.
- the light naphtha stream is passed to an adsorption separation unit to generate an extract stream and a raffinate stream.
- the extract stream comprises normal hydrocarbons and is passed to a cracking unit to generate light olefins.
- the cracking unit can be a steam cracking unit or a catalytic cracking unit.
- the raffinate stream is passed to the reforming unit.
- the isoparaffins can isomerize to normal paraffins, and the unaromatized paraffins can be recovered and recycled for passing to the cracking unit.
- the raffinate stream can be passed to a fractionation unit.
- the fractionation unit can generate an overhead stream, a bottoms stream and a side draw stream 76.
- the fractionation column can be a divided wall column.
- the overhead stream can comprises isoparaffins having 5 and 6 carbon atoms, and the bottoms stream can comprise methyl cyclopentane, cyclohexane and benzene.
- the overhead stream can be passed to a gasoline blending stock, or to the reformer to isomerizes the isoparaffins to normal paraffins.
- the fractionation unit can be operated to control for the production of the side draw stream, where the side draw stream can be passed to a gasoline blending stock.
- the overhead stream can be used to control the hydrocarbon compositions of the gasoline blending stock to provide control over the Reid vapor pressure.
- the aromatics stream from the reforming unit can be passed to an aromatics extraction unit to generate an aromatics product stream and an aromatics extraction raffinate.
- the aromatics extraction raffinate can be passed to the adsorption separation column to separate the normal paraffins from the non-normal hydrocarbons.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the reformed effluent to an aromatics extraction unit to generate an aromatics stream and an extraction raffinate stream comprising C5 and C6 paraffins.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the extraction raffinate stream to the cracking unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the aromatics stream to an aromatics complex.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph wherein the heavy desorbent is normal heptane, normal octane, normal nonane, normal decane, normal undecane or normal dodecane.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the first embodiment in this paragraph further comprising passing the raffinate stream to the reforming unit.
- a second embodiment of the invention is a process for improved light olefin yields from naphtha, comprising passing a naphtha feedstream to a naphtha splitter to generate a light naphtha comprising C6 and lighter hydrocarbons and a heavy naphtha;
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the reformate stream to an aromatics extraction unit to generate an aromatics stream and an extraction raffinate.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the raffinate stream to the reforming unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the raffinate stream to a fractionation unit to generate an overhead stream comprising isoparaffins having 5 and 6 carbons, and a bottoms stream comprising methyl cyclopentane, cyclohexane and benzene.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the bottoms stream to the reforming unit.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph further comprising passing the overhead stream to a gasoline blending stock or to a reformer.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph wherein the adsorption separation unit uses a light desorbent.
- An embodiment of the invention is one, any or all of prior embodiments in this paragraph up through the second embodiment in this paragraph wherein the fractionation unit generates a bottoms stream, a side draw stream for passing to a gasoline blending stock, and an overhead stream for providing control over the Reid vapor pressure of the gasoline blending stock.
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US201662334891P | 2016-05-11 | 2016-05-11 | |
PCT/US2017/030949 WO2017196619A1 (en) | 2016-05-11 | 2017-05-04 | Use of platforming process to isomerize light paraffins |
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EP3455336A1 true EP3455336A1 (en) | 2019-03-20 |
EP3455336A4 EP3455336A4 (en) | 2019-11-13 |
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EP (1) | EP3455336B1 (en) |
KR (1) | KR102142606B1 (en) |
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WO (1) | WO2017196619A1 (en) |
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US11072748B2 (en) | 2019-12-09 | 2021-07-27 | Saudi Arabian Oil Company | Selective reforming process to produce gasoline blending components and aromatics |
US11028329B1 (en) | 2020-04-10 | 2021-06-08 | Saudi Arabian Oil Company | Producing C6-C8 aromatics from FCC heavy naphtha |
US11597883B2 (en) * | 2021-06-07 | 2023-03-07 | Uop Llc | Process for removing olefins from normal paraffins in an isomerization effluent stream |
US20230036734A1 (en) * | 2021-07-15 | 2023-02-02 | Uop Llc | Process for increasing the concentration of normal paraffins in a light naphtha stream |
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EP0109060B1 (en) | 1982-11-10 | 1987-03-11 | MONTEDIPE S.p.A. | Process for the conversion of linear butenes to propylene |
US4747933A (en) | 1987-03-27 | 1988-05-31 | Uop Inc. | Isomerization unit with integrated feed and product separation facilities |
US6407301B1 (en) * | 2000-10-30 | 2002-06-18 | Uop Llc | Ethylene production by steam cracking of normal paraffins |
WO2006063201A1 (en) * | 2004-12-10 | 2006-06-15 | Bhirud Vasant L | Steam cracking with naphtha dearomatization |
US8283511B2 (en) * | 2010-03-30 | 2012-10-09 | Uop Llc | Ethylene production by steam cracking of normal paraffins |
CN105264050B (en) * | 2013-06-04 | 2017-12-08 | 环球油品公司 | Naphtha pyrolysis |
US20150045598A1 (en) * | 2013-08-07 | 2015-02-12 | Uop Llc | Flexible process for enhancing steam cracker and platforming feedstocks |
US20150166435A1 (en) * | 2013-12-13 | 2015-06-18 | Uop Llc | Methods and apparatuses for processing hydrocarbons |
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US20180327675A1 (en) | 2018-11-15 |
EP3455336B1 (en) | 2020-12-23 |
KR102142606B1 (en) | 2020-08-07 |
KR20180100612A (en) | 2018-09-11 |
EP3455336A4 (en) | 2019-11-13 |
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