EP0448439A1 - Verfahren zur Fraktionierung von einem Gasgemisch enthaltend Wasserstoff, leichte alifatische Kohlenwasserstoffe und leichte aromatische Kohlenwasserstoffe - Google Patents

Verfahren zur Fraktionierung von einem Gasgemisch enthaltend Wasserstoff, leichte alifatische Kohlenwasserstoffe und leichte aromatische Kohlenwasserstoffe Download PDF

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Publication number
EP0448439A1
EP0448439A1 EP91400637A EP91400637A EP0448439A1 EP 0448439 A1 EP0448439 A1 EP 0448439A1 EP 91400637 A EP91400637 A EP 91400637A EP 91400637 A EP91400637 A EP 91400637A EP 0448439 A1 EP0448439 A1 EP 0448439A1
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Prior art keywords
fraction
liquid
gaseous
hydrocarbons
gas
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EP91400637A
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English (en)
French (fr)
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EP0448439B1 (de
Inventor
Ari Minkkinen
Serge Mouratoff
Larry Mank
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IFP Energies Nouvelles IFPEN
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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
    • 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
    • C10G5/00—Recovery of liquid hydrocarbon mixtures from gases, e.g. natural gas
    • C10G5/04—Recovery of liquid hydrocarbon mixtures from gases, e.g. natural gas with liquid absorbents

Definitions

  • the invention relates to a process for fractionating a gaseous mixture containing hydrogen, light aliphatic hydrocarbons and light aromatic hydrocarbons.
  • the invention aims, more particularly, to separately collect (1) hydrogen of high purity, and in particular only contain traces of aromatic hydrocarbons, (2), aliphatic hydrocarbons C2 - C5, in particular C3 or C3 - C4, which can be recycled, at least in part, to a hydrocarbon conversion process, for example a dehydrocyclodimerization process, and (3) light aromatic hydrocarbons alone or as a mixture (BTX).
  • a hydrocarbon conversion process for example a dehydrocyclodimerization process
  • BTX light aromatic hydrocarbons alone or as a mixture
  • the effluent is a mixture of hydrogen, light aliphatic hydrocarbons, in particular from C1 to C5, and light aromatic hydrocarbons, in particular benzene, toluene and / or xylene or their mixtures ( BTX).
  • these processes mention may be made of catalytic reforming, aromatization, dehydrogenation, dehydrocyclization, steam cracking and dehydrocyclodimerization.
  • light paraffins or olefins for example C3 and C4 are converted into light aromatic hydrocarbons in contact with zeolitic catalysts.
  • the hydrogen is separated in a high pressure separator and the hydrocarbons are separated in a train of distillation columns.
  • perm-selective membranes have also been proposed for separating hydrogen from hydrocarbons, for example in US 4180388, 4398926 and 4654047.
  • the use of a perm-selective membrane and fractionation columns is described in US 45488619 In this latter patent, the effluent from a dehydrocyclodimerization unit is first briefly fractionated; the liquid fraction is distilled to collect the BTX and the gaseous fraction is compressed and then washed with aromatic hydrocarbons or with C7 - C10 paraffinic hydrocarbons of external origin.
  • the present invention relates to a process for fractionating a gaseous mixture containing hydrogen, light aliphatic hydrocarbons and aromatic hydrocarbons, energy efficient, in particular in which the energy requirements for fractionation of the products are reduced; and also a process in which the hydrogen obtained is substantially free of aromatic hydrocarbons; a process also which makes it possible to use membranes sensitive to aromatic hydrocarbons, due to the virtual absence of these in the gas subjected to permeation. In the process of the invention, the undesirable crystallization of aromatic hydrocarbons is avoided.
  • a gaseous mixture and for example, the gaseous effluent from a hydrocarbon conversion reactor, which contains hydrogen, light aliphatic hydrocarbons and light aromatic hydrocarbons is first cooled at a temperature allowing the condensation of part of the hydrocarbons. Separating a first non-condensed gaseous fraction relatively poor in aromatics and a first liquid fraction relatively poor in aromatics and a first liquid fraction relatively rich in aromatics.
  • the first gaseous fraction is compressed and cooled, so as to condense at least a second liquid fraction, and the second liquid fraction is separated from a second non-condensed gaseous fraction.
  • the second gaseous fraction is brought into contact with a liquid phase of aliphatic hydrocarbons, defined below, in a contact zone, under conditions ensuring at the same time the vaporization of at least one fraction, for example at least 50% ( preferably 60-95%), of the liquid phase of aliphatic hydrocarbons, and the condensation of at least part of the aromatic hydrocarbons of the second gaseous fraction, said condensation being caused, at least in part by the cooling due to the vaporization of aliphatic hydrocarbons, and a third gas fraction is separated from a third liquid fraction comprising aliphatic hydrocarbons and aromatic hydrocarbons.
  • the second and third liquid fractions can also be drawn off as a mixture.
  • the third gas fraction is treated to bring it above the dew point, it is circulated in contact with at least one membrane permeable to hydrogen and a gas fraction enriched in hydrogen and a fourth depleted gas fraction are collected. into hydrogen.
  • the fourth gas fraction is cooled so as to partially condense it and a fifth gas fraction, rich in methane, which can constitute a "fuel-gas", and a fourth liquid fraction containing at least one C3 hydrocarbon are collected. to C5.
  • the first, second, third and fourth liquid fractions are subjected to distillation, together or separately, in one or more columns, and at least a sixth gaseous fraction containing at least one C3 or C5 hydrocarbon is collected at the top and at least in the tail a fifth liquid fraction which constitutes a desired aromatic hydrocarbon fraction. At least a part of the hydrocarbons of the sixth gaseous fraction are condensed and sent to the contact zone to constitute at least a part of the liquid phase of aliphatic hydrocarbons.
  • Preferably another part of the sixth gaseous fraction is sent to the hydrocarbon conversion reactor, as a recycling stream, at least when one or more of the hydrocarbons from C3 to C5 constitute a reagent for said conversion.
  • the hydrocarbon conversion reactor can be, for example, a C2-C5, particularly C3 and / or C4 light hydrocarbon aromatization reactor, using a zeolite as catalyst, in particular a zeolite described in French patent 2634139 or 2634140 .
  • the pressure at the outlet of the reactor is, for example 1.5 to 10 bars, commonly 2-5 bars. If the temperature is high, it is lowered to 10-60 ° C, preferably 30-50 ° C, so as to condense part of the gaseous effluent from the reactor and to collect at least part of the aromatic hydrocarbons. If desired, the pressure can be modified to promote the condensation of aromatic hydrocarbons.
  • the first gas fraction is then compressed to, for example, 15-40 bars, preferably 20-30 bars, and cooled, to bring its temperature to 0-50 ° C, preferably 25-35 ° C, and condense at least a second liquid fraction, containing aromatics.
  • This liquid fraction is separated from the second gaseous fraction under the above pressure.
  • several compression stages can be used, each followed by partial condensation and fractionation.
  • the bringing of the second gaseous fraction into contact with the recycled liquid phase of aliphatic hydrocarbons containing at least one hydrocarbon C3 to C5, preferably C4-C5, constitutes an essential point of the invention.
  • the vaporization of at least 50% of the hydrocarbons C3 to C5 from this liquid phase causes the second gaseous fraction to cool and the condensation of at least part of the residual aromatic hydrocarbons.
  • the temperature is, for example, between - 10 and + 40 ° C, preferably between 5 and 35 ° C. At the top the temperature is between - 10 and + 30 ° C, preferably for example between 0 and 20 ° C.
  • the pressure may be substantially that of the second gas fraction (after compression of the first gas fraction), that is to say, 15-40 bars, preferably 20-30 bars.
  • the quantity of liquid phase of aliphatic hydrocarbons can represent, for example, 5 to 35% preferably 10 to 25% of the quantity of second gaseous fraction, but the invention is not limited to particular proportions .
  • the recycled liquid phase of aliphatic hydrocarbons also to contain a certain proportion of non-aromatic hydrocarbons C6, C7 and / or C8.
  • the resulting gas stream is then brought above its dew point, for example by heating or by dilution with a dry gas, but preferably by additional compression ensuring overheating (an increment of 2 to 7 bars is generally sufficient). It is then brought into contact with at least one selective permeation membrane, in one or more stages.
  • the overheating is preferably such that no condensation occurs during the withdrawal of hydrogen from the membrane.
  • permeation membrane For permeation, reference may be made to one of the aforementioned patents, and it will preferably be carried out in several stages with gas recompression between the stages.
  • the permeation membrane may be a commercial or prior art membrane and will therefore not be described in detail.
  • the operating conditions depend on the membrane, for example around 80-150 ° C at 20-40 bars with the usual membranes.
  • the fraction of hydrogen-depleted gas which usually contains C1-C5 hydrocarbons is subjected to cooling in order to condense a liquid phase containing C3-C5 hydrocarbons.
  • the cooling may use, in part, relatively cold streams of the process, for example the stream of the fifth gaseous fraction, and, in part, streams of liquefied gas, for example a stream of liquid propane or ethane.
  • the distillation of the liquid fractions can be carried out separately or after mixing 2 or more fractions. It is also possible not to distill the second liquid fraction directly and to return it to the first fractionation zone in order to be fractionated again in mixture with the reactor effluent.
  • a mixture of the first liquid fraction and the second liquid fraction can be distilled; the third and fourth liquid fractions are then distilled separately.
  • the first, second, third and fourth liquid fractions can also be distilled together. Other combinations of fractions can also be used.
  • the third gaseous fraction is compressed before passing through the permeation zone.
  • the compressor can then be in line with the compressors of the previous stages.
  • the compressor for the third gaseous fraction receives the energy, preferably mechanical energy, produced by a regulator placed on the circuit of the fifth gaseous fraction.
  • a turbocharger and a turboexpander are preferably used respectively.
  • the sixth gaseous fraction is subjected to partial condensation: at least part of the condensate rich in butanes and pentanes is used as liquid for contacting with the second gaseous fraction, the rest is returned as reflux to the column in which said sixth gas fraction was separated from said fifth liquid fraction; the non-condensed part, constituting a seventh gas fraction rich in propane, can be returned to the dehydrocyclodimerization reactor.
  • the figure illustrates a non-limiting mode of implementation of the invention.
  • the gaseous effluent (1) from a paraffin flavoring unit C3 - C9 available at 1.5 - 5 bars is cooled to 30 - 40 ° C in the exchanger (2). It optionally receives the current (3).
  • part of the gas phase is condensed and a liquid phase (5) and a gas phase (6) are separated in the flask (4). This undergoes one or more compression stages (7) followed by cooling (8).
  • the liquids collected can be sent by line (9) for distillation or by line (3) at the entrance to the installation. From the flask (10) a gas stream (11) comes out which is contacted in the flask (12) with a liquid stream C3-C5 from the line (13).
  • the gas phase (14) undergoes compression with overheating in the compressor (15) and then passes into the permeation unit (16).
  • Purified hydrogen exits through line (17).
  • the residual gas (38) is cooled, for example by cold water (18), by a stream of cold gas (19-21) and by liquid propane (20) at low temperature, for example - 30 to - 40 ° C.
  • a partial liquefaction takes place and a methane-rich gas is collected at the top of the column (23) via the line (21) and a liquid stream (22) at the bottom of the column (23).
  • the liquid stream (24) withdrawn from the contactor (12) is also sent to the column (23), but preferably at a point lower than that of admission of the stream coming from the permeation unit.
  • the liquid (22) is refracted in the column (25) which, in the example considered, also receives the liquid from line (5).
  • the latter is preferably introduced at a relatively low point of the column (25), lower than the level of introduction of the liquid (22).
  • a mixture rich in aromatic hydrocarbons is collected by line (26).
  • the vapors (27), rich in hydrocarbons (C3-C5) are cooled and partially condensed (28).
  • a liquid phase is collected, for example C3-C5 or C4-C5, which is returned in part to the contactor (12) by the line (13).
  • a reflux can be ensured by the line (31). If a gas phase (32) remains, it can be returned to the dehydrocyclodimerization reactor.
  • the separator (10) is not used and the current which has passed through the cooler (8) is sent directly to the bottom of the contactor (12).
  • the second and third liquid fractions exit in mixture through the line (24). Lines (9) and (3) are then not used.
  • the heat released by compression in a compression stage (7) is used to heat the reboiler of a distillation column (23), the gas leaving (33) from the compressor (7) then passes through an exchanger in the reboiler (32) of this column then is sent (34) to the balloon (10) or to the contactor (12).
  • the cooler (8) can then be removed (35,36,37) are expansion valves.

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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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
EP91400637A 1990-03-20 1991-03-07 Verfahren zur Fraktionierung von einem Gasgemisch enthaltend Wasserstoff, leichte alifatische Kohlenwasserstoffe und leichte aromatische Kohlenwasserstoffe Expired - Lifetime EP0448439B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9003652A FR2659964B1 (fr) 1990-03-20 1990-03-20 Procede de fractionnement d'un melange gazeux renfermant de l'hydrogene des hydrocarbures aliphatiques legers et des hydrocarbures aromatiques legers.
FR9003652 1990-03-20

Publications (2)

Publication Number Publication Date
EP0448439A1 true EP0448439A1 (de) 1991-09-25
EP0448439B1 EP0448439B1 (de) 1995-07-26

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EP91400637A Expired - Lifetime EP0448439B1 (de) 1990-03-20 1991-03-07 Verfahren zur Fraktionierung von einem Gasgemisch enthaltend Wasserstoff, leichte alifatische Kohlenwasserstoffe und leichte aromatische Kohlenwasserstoffe

Country Status (5)

Country Link
US (1) US5157200A (de)
EP (1) EP0448439B1 (de)
JP (1) JP2905942B2 (de)
DE (1) DE69111497T2 (de)
FR (1) FR2659964B1 (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100197145B1 (ko) * 1989-12-19 1999-06-15 후지이 히로시 금속표면의 인산아연 처리방법
WO1994002438A1 (en) * 1992-07-24 1994-02-03 Chevron Chemical Company Reforming process for producing high-purity benzene
WO1997041085A1 (en) * 1996-04-30 1997-11-06 Mitsubishi Chemical Corporation Method for separating hydrogen and methane from gaseous hydrocarbon
JPH10203803A (ja) * 1997-01-20 1998-08-04 Ngk Insulators Ltd 水素ガスの回収・精製・貯蔵装置
US6159272A (en) * 1997-01-24 2000-12-12 Membrane Technology And Research, Inc. Hydrogen recovery process
US5980609A (en) * 1997-01-24 1999-11-09 Membrane Technology And Research, Inc. Hydrogen recovery process
US5769927A (en) * 1997-01-24 1998-06-23 Membrane Technology And Research, Inc. Monomer recovery process
US5785739A (en) * 1997-01-24 1998-07-28 Membrane Technology And Research, Inc. Steam cracker gas separation process
US6264828B1 (en) 1998-05-22 2001-07-24 Membrane Tehnology And Research, Inc. Process, including membrane separation, for separating hydrogen from hydrocarbons
US6171472B1 (en) 1998-05-22 2001-01-09 Membrane Technology And Research, Inc. Selective purge for reactor recycle loop
US6011192A (en) * 1998-05-22 2000-01-04 Membrane Technology And Research, Inc. Membrane-based conditioning for adsorption system feed gases
US6190540B1 (en) 1998-05-22 2001-02-20 Membrane Technology And Research, Inc. Selective purging for hydroprocessing reactor loop
US6165350A (en) * 1998-05-22 2000-12-26 Membrane Technology And Research, Inc. Selective purge for catalytic reformer recycle loop
US6179996B1 (en) 1998-05-22 2001-01-30 Membrane Technology And Research, Inc. Selective purge for hydrogenation reactor recycle loop
US6190536B1 (en) 1998-05-22 2001-02-20 Membrane Technology And Research, Inc. Catalytic cracking process
US6183628B1 (en) 1999-03-19 2001-02-06 Membrane Technology And Research, Inc. Process, including PSA and membrane separation, for separating hydrogen from hydrocarbons
US6592749B1 (en) 1999-03-19 2003-07-15 Membrane Technology And Research, Inc. Hydrogen/hydrocarbon separation process, including PSA and membranes
US6589303B1 (en) 1999-12-23 2003-07-08 Membrane Technology And Research, Inc. Hydrogen production by process including membrane gas separation
FR2856697B1 (fr) * 2003-06-24 2005-08-26 Air Liquide Procede de traitement de l'effluent d'une unite de reformage catalytique
WO2005037421A2 (en) * 2003-10-14 2005-04-28 Advanced Technology Materials, Inc. Hydrogen generation
US9517933B2 (en) 2013-09-23 2016-12-13 Uop Llc Process for catalytic reforming
US9637426B2 (en) * 2014-10-27 2017-05-02 Uop Llc Methods and apparatuses for reforming of hydrocarbons including recovery of products using a recontacting zone

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2265673A1 (en) * 1974-03-27 1975-10-24 Raffinage Cie Francaise Sepn of hydrogen from hydrocarbon conversion effluents - by passage through diffusion barriers, and recycling hydrogen
EP0002171A1 (de) * 1977-11-23 1979-05-30 Cosden Technology Inc. Verfahren zur Erhöhung der Reinheit von rezykliertem gasförmigem Wasserstoff
EP0061259A1 (de) * 1981-03-12 1982-09-29 Monsanto Company Hydrokrackverfahren mit verbessertem Wasserstoff-Nutzungsgrad
FR2506744A1 (fr) * 1981-05-26 1982-12-03 Air Prod & Chem Procede et appareil pour recuperer l'hydrogene a partir d'un courant d'alimentation contenant du methane, de l'ethylene, de l'hydrogene et de l'acetylene
EP0340465A2 (de) * 1988-04-28 1989-11-08 Linde Aktiengesellschaft Verfahren zur Abtrennung von Kohlenwasserstoffen

Family Cites Families (1)

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Publication number Priority date Publication date Assignee Title
US4548619A (en) * 1984-10-11 1985-10-22 Uop Inc. Dehydrocyclodimerization process

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2265673A1 (en) * 1974-03-27 1975-10-24 Raffinage Cie Francaise Sepn of hydrogen from hydrocarbon conversion effluents - by passage through diffusion barriers, and recycling hydrogen
EP0002171A1 (de) * 1977-11-23 1979-05-30 Cosden Technology Inc. Verfahren zur Erhöhung der Reinheit von rezykliertem gasförmigem Wasserstoff
EP0061259A1 (de) * 1981-03-12 1982-09-29 Monsanto Company Hydrokrackverfahren mit verbessertem Wasserstoff-Nutzungsgrad
FR2506744A1 (fr) * 1981-05-26 1982-12-03 Air Prod & Chem Procede et appareil pour recuperer l'hydrogene a partir d'un courant d'alimentation contenant du methane, de l'ethylene, de l'hydrogene et de l'acetylene
EP0340465A2 (de) * 1988-04-28 1989-11-08 Linde Aktiengesellschaft Verfahren zur Abtrennung von Kohlenwasserstoffen

Also Published As

Publication number Publication date
DE69111497D1 (de) 1995-08-31
FR2659964B1 (fr) 1992-06-05
FR2659964A1 (fr) 1991-09-27
EP0448439B1 (de) 1995-07-26
US5157200A (en) 1992-10-20
DE69111497T2 (de) 1996-04-04
JP2905942B2 (ja) 1999-06-14
JPH04217632A (ja) 1992-08-07

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