WO2018180210A1 - Procédé de régénération de film - Google Patents
Procédé de régénération de film Download PDFInfo
- Publication number
- WO2018180210A1 WO2018180210A1 PCT/JP2018/008118 JP2018008118W WO2018180210A1 WO 2018180210 A1 WO2018180210 A1 WO 2018180210A1 JP 2018008118 W JP2018008118 W JP 2018008118W WO 2018180210 A1 WO2018180210 A1 WO 2018180210A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- membrane
- zeolite membrane
- separation
- inert gas
- zeolite
- Prior art date
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- 238000011069 regeneration method Methods 0.000 title claims abstract description 34
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 182
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 180
- 239000010457 zeolite Substances 0.000 claims abstract description 180
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 111
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 102
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 89
- 239000000203 mixture Substances 0.000 claims abstract description 80
- 239000011261 inert gas Substances 0.000 claims abstract description 78
- 239000012528 membrane Substances 0.000 claims description 280
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 229910001873 dinitrogen Inorganic materials 0.000 claims description 26
- 238000000926 separation method Methods 0.000 abstract description 136
- 230000001172 regenerating effect Effects 0.000 abstract description 7
- 239000007789 gas Substances 0.000 description 57
- 239000012466 permeate Substances 0.000 description 39
- 125000004432 carbon atom Chemical group C* 0.000 description 28
- 230000007246 mechanism Effects 0.000 description 27
- 239000002994 raw material Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 17
- 125000000753 cycloalkyl group Chemical group 0.000 description 13
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 9
- 230000006872 improvement Effects 0.000 description 8
- 230000008569 process Effects 0.000 description 8
- 230000008929 regeneration Effects 0.000 description 8
- 239000013078 crystal Substances 0.000 description 6
- 239000011148 porous material Substances 0.000 description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- 230000004907 flux Effects 0.000 description 3
- 238000003825 pressing Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 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
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 229910000323 aluminium silicate Inorganic materials 0.000 description 2
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- KZHJGOXRZJKJNY-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Si]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O.O=[Al]O[Al]=O KZHJGOXRZJKJNY-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 229910052863 mullite Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 2
- QMMOXUPEWRXHJS-UHFFFAOYSA-N pentene-2 Natural products CCC=CC QMMOXUPEWRXHJS-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052878 cordierite Inorganic materials 0.000 description 1
- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- JSKIRARMQDRGJZ-UHFFFAOYSA-N dimagnesium dioxido-bis[(1-oxido-3-oxo-2,4,6,8,9-pentaoxa-1,3-disila-5,7-dialuminabicyclo[3.3.1]nonan-7-yl)oxy]silane Chemical compound [Mg++].[Mg++].[O-][Si]([O-])(O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2)O[Al]1O[Al]2O[Si](=O)O[Si]([O-])(O1)O2 JSKIRARMQDRGJZ-UHFFFAOYSA-N 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000010304 firing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- 239000001282 iso-butane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000005288 shirasu porous glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D65/00—Accessories or auxiliary operations, in general, for separation processes or apparatus using semi-permeable membranes
- B01D65/02—Membrane cleaning or sterilisation ; Membrane regeneration
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D71/00—Semi-permeable membranes for separation processes or apparatus characterised by the material; Manufacturing processes specially adapted therefor
- B01D71/02—Inorganic material
Definitions
- the present invention relates to a membrane regeneration method, and more particularly to a membrane regeneration method for regenerating a membrane that can be suitably used when separating some hydrocarbons from a hydrocarbon mixture.
- a membrane separation method has been used as a method for separating a specific component from a multi-component mixture with low energy.
- the separation membrane for example, a zeolite membrane formed by forming a zeolite on a support in the form of a membrane is used.
- the performance of the zeolite membrane used for membrane separation is expressed by the permeation flux of the permeate and the separation factor. And the zeolite membrane used for membrane separation is calculated
- an object of the present invention is to provide a membrane regeneration method that can sufficiently increase the separation factor of a separation membrane for membrane separation of a hydrocarbon mixture.
- the present inventors have intensively studied to achieve the above object.
- the present inventors have found that if the zeolite membrane used for membrane separation of the hydrocarbon mixture is regenerated using a specific regeneration gas, the separation factor of the zeolite membrane can be sufficiently increased, and the present invention has been completed. I let you.
- the present invention aims to advantageously solve the above problems, and the membrane separation method of the present invention comprises a step (A) of bringing a hydrocarbon mixture into contact with a zeolite membrane, and an inert gas. And (B) exposing the zeolite membrane to an atmosphere to raise the temperature of the inert gas atmosphere. In this way, the zeolite membrane brought into contact with the hydrocarbon mixture is exposed to an inert gas atmosphere, and the atmosphere is regenerated while raising the temperature, so that the separation factor of the zeolite membrane obtained through the step (B) is sufficient. Can be increased.
- the maximum temperature of the inert gas atmosphere in the step (B) is 100 ° C. or higher and 450 ° C. or lower. If the maximum temperature of the inert gas atmosphere to which the zeolite membrane is exposed during the step (B) is 100 ° C. or higher and 450 ° C. or lower, the separation factor of the zeolite membrane is more sufficiently suppressed while suppressing the loss of the zeolite membrane due to heat. Can be increased.
- the inert gas is preferably nitrogen gas. If the atmosphere to which the zeolite membrane is exposed is nitrogen gas, the separation coefficient of the zeolite membrane can be further sufficiently increased by effectively regenerating the porosity of the zeolite membrane.
- the zeolite membrane in the step (B), is exposed to the inert gas atmosphere before the temperature of the inert gas atmosphere is increased. It is preferable to further include a film pressurizing operation for pressurization. By performing such a membrane pressurizing step, the separation factor of the zeolite membrane can be further sufficiently increased.
- the membrane regeneration method of the present invention can be used for regeneration of a zeolite membrane that can be suitably used for membrane separation of a hydrocarbon mixture.
- the membrane regeneration method of the present invention can remarkably improve the separation factor of a zeolite membrane when a new zeolite membrane brought into contact with a hydrocarbon mixture is treated for the first time.
- the membrane regeneration method of the present invention is a method for regenerating a zeolite membrane that can be used for membrane separation of a hydrocarbon mixture.
- a membrane regeneration method includes a step (A) of bringing a hydrocarbon mixture into contact with a zeolite membrane, and a step (B) of exposing the zeolite membrane to an inert gas atmosphere to raise the temperature of the inert gas atmosphere.
- the membrane regeneration method of the present invention after bringing the hydrocarbon mixture into contact with the zeolite membrane, the zeolite membrane is exposed to an inert gas atmosphere, and the membrane is regenerated while raising the temperature of the inert gas atmosphere. Therefore, the separation factor of the zeolite membrane can be sufficiently increased. As a result, it is possible to achieve good separation performance when the regenerated zeolite membrane is used for separation of a hydrocarbon mixture.
- the reason why it is possible to sufficiently increase the separation factor of the zeolite membrane by regenerating the zeolite membrane while raising the temperature in an inert gas atmosphere is not clear, but it is assumed that it is as follows.
- the zeolite membrane brought into contact with the hydrocarbon mixture retains the hydrocarbon component adsorbed or adhered to the membrane.
- Such a component can block or narrow the innumerable pores of a zeolite membrane that is originally porous.
- the permeation flux and the separation factor are reduced in the zeolite membrane after the operation of bringing the hydrocarbon mixture into contact, such as separating the hydrocarbon mixture.
- the zeolite membrane is a membrane formed by growing zeolite crystals on a support.
- zeolite crystals include micropores having a pore diameter of 2 nm or less, and mesopores having a pore diameter of more than 2 nm and not more than 50 nm are formed at a crystal grain boundary formed between the plurality of crystals.
- the plural types of hydrocarbon compounds contained in the hydrocarbon mixture to be separated include those that are relatively easy to pass through the pores and those that are difficult to pass depending on their structure.
- the separation factor is obtained due to the difference in pore permeability of each hydrocarbon compound.
- the pores may be blocked or narrowed with the passage of the separation time. For this reason, a separation factor falls by operation which makes a hydrocarbon mixture contact.
- the zeolite membrane is regenerated while raising the temperature in an inert gas atmosphere. Since it can be created well during regeneration, it is presumed that the separation factor of the zeolite membrane can be sufficiently increased compared to the zeolite membrane before the regeneration treatment.
- the hydrocarbon mixture that is the separation target of the zeolite membrane that can be regenerated by the membrane regeneration method of the present invention is a plurality of types of carbonized compounds that can separate some hydrocarbon compounds using the zeolite membrane.
- the hydrocarbon mixture include a mixture containing a straight-chain hydrocarbon having the same number of carbon atoms, a branched hydrocarbon and / or a cyclic hydrocarbon.
- the hydrocarbon mixture is preferably a mixture containing as a main component a linear hydrocarbon having 4 carbon atoms and a branched hydrocarbon having 4 carbon atoms and / or a cyclic hydrocarbon having 4 carbon atoms, Alternatively, it is a mixture containing as a main component a linear hydrocarbon having 5 carbon atoms and a branched hydrocarbon having 5 carbon atoms and / or a cyclic hydrocarbon having 5 carbon atoms, and more preferably a carbon number Is a mixture containing as a main component a linear hydrocarbon having 5 and a branched hydrocarbon having 5 carbon atoms and / or a cyclic hydrocarbon having 5 carbon atoms.
- linear hydrocarbons and branched hydrocarbons and / or cyclic hydrocarbons as main components means linear hydrocarbons and branched hydrocarbons in a hydrocarbon mixture. It refers to containing 50 mol% or more of hydrogen and / or cyclic hydrocarbons in total.
- a mixture containing a linear hydrocarbon having 4 carbon atoms and a branched hydrocarbon and / or a cyclic hydrocarbon having 4 carbon atoms as main components (hereinafter referred to as “a hydrocarbon mixture having 4 carbon atoms”)
- a hydrocarbon mixture having 4 carbon atoms As a straight chain hydrocarbon having 4 carbon atoms such as n-butane, 1-butene, 2-butene and butadiene, and a branched hydrocarbon having 4 carbon atoms such as isobutane and isobutene.
- a mixture containing a cyclic hydrocarbon having 4 carbon atoms such as cyclobutane and cyclobutene.
- the hydrocarbon mixture having 4 carbon atoms includes, for example, a C4 fraction produced as a by-product when pyrolyzing naphtha to produce ethylene, or after recovering at least a part of butadiene from the C4 fraction. Examples include remaining fractions.
- a mixture containing as a main component a linear hydrocarbon having 5 carbon atoms and a branched hydrocarbon and / or cyclic hydrocarbon having 5 carbon atoms (hereinafter referred to as “a hydrocarbon mixture having 5 carbon atoms”) And a linear hydrocarbon having 5 carbon atoms such as n-pentane, 1-pentene, 2-pentene, 1,3-pentadiene, isopentane, 2-methyl-1-butene, A mixture containing a branched hydrocarbon having 5 carbon atoms such as 2-methyl-2-butene, 3-methyl-1-butene and isoprene and / or a cyclic hydrocarbon having 5 carbon atoms such as cyclopentane and cyclopentene.
- the hydrocarbon mixture having 5 carbon atoms includes, for example, a C5 fraction produced as a by-product when pyrolyzing naphtha to produce ethylene, or after recovering at least a portion of isoprene from the C5 fraction. Examples include remaining fractions.
- examples of the zeolite membrane regenerated by the membrane regeneration method of the present invention include any zeolite membrane capable of separating a desired hydrocarbon compound from a hydrocarbon mixture.
- the zeolite membrane includes a porous support and a porous separation layer provided on the porous support, and a porous separation layer is desired.
- a porous support that is a zeolite membrane that can be suitably used for membrane separation of a hydrocarbon mixture having 4 carbon atoms or a hydrocarbon mixture having 5 carbon atoms, and a porous support on the porous support.
- a separation membrane comprising an MFI-type zeolite (aluminosilicate having a MFI structure and / or silicalite).
- porous support a porous body made of any material can be used as long as it is a porous body capable of supporting the porous separation layer.
- porous bodies made of porous ceramics such as alumina, mullite, zirconia, cordierite, etc .; glass such as shirasu porous glass; and porous sintered metals such as stainless steel are preferable. This is because a porous body made of porous ceramics or porous sintered metal is excellent in mechanical strength.
- the shape of the porous support is not particularly limited, and can be any shape such as a flat film shape, a flat plate shape, a tube shape, and a honeycomb shape.
- the porous separation layer can be formed, for example, by synthesizing zeolite having a desired structure such as MFI-type zeolite on a porous support or a porous support to which a zeolite seed crystal is attached.
- the porous separation layer is obtained by immersing a porous support optionally attached with a zeolite seed crystal in an aqueous sol containing a silica source and a structure-directing agent, and synthesizing the zeolite by hydrothermal synthesis.
- the zeolite membrane obtained by forming the porous separation layer on the porous support is subjected to a calcination treatment for removing the structure-directing agent and a boiling washing treatment, followed by oxygen-containing conditions such as in an air atmosphere. It may have been subjected to a baking treatment in an atmosphere.
- step (A) the hydrocarbon mixture is brought into contact with the zeolite membrane.
- step (A) can be a separation step for performing membrane separation or an exposure step for exposing the zeolite membrane to a hydrocarbon mixture gas. That is, the step (A) is a step that can be carried out by any specific operation without particular limitation as long as the hydrocarbon mixture can be brought into contact with the zeolite membrane.
- the hydrocarbon component can be adsorbed or adhered to the zeolite membrane by bringing the hydrocarbon mixture into contact with the zeolite membrane.
- step (A) is a separation step
- a part of the hydrocarbon compound contained in the hydrocarbon mixture is separated by the zeolite membrane.
- the step (A) that is the separation step for example, carbonization including linear hydrocarbons, branched hydrocarbons and / or cyclic hydrocarbons having the same number of carbon atoms.
- linear hydrocarbons can be efficiently separated and removed from the hydrogen mixture, thereby increasing the content of branched hydrocarbons and / or cyclic hydrocarbons in the hydrocarbon mixture.
- step (A) which is a separation step
- a part of the components can be separated and removed from the hydrocarbon mixture by passing the hydrocarbon mixture through a zeolite membrane. it can.
- the separation step using a zeolite membrane can be performed under any conditions, but is preferably performed under heating conditions. Specifically, the separation step is preferably performed under conditions of 20 ° C. or higher and 300 ° C. or lower, more preferably 25 ° C. or higher and 250 ° C. or lower, and further preferably 50 ° C. or higher and 200 ° C. or lower.
- the pressure conditions for performing the separation step are not particularly limited, but it is preferable that the differential pressure between the non-permeation side and the permeation side (pressure on the non-permeation side ⁇ pressure on the permeation side) be 10 kPa or more and 600 kPa or less, More preferably, it is 50 kPa or more and 300 kPa or less. In the present specification, the pressure is a gauge pressure.
- step (A) is an exposure step
- a hydrocarbon mixture containing linear hydrocarbons having the same number of carbon atoms and branched hydrocarbons and / or cyclic hydrocarbons is used as the zeolite membrane. It can be introduced on the non-permeable side and / or on the transmissive side.
- the pressure of the hydrocarbon mixture-containing atmosphere to which the zeolite membrane is exposed is preferably, for example, 0 kPa or more and 600 kPa or less.
- the place where the zeolite membrane is exposed to the hydrocarbon mixture is, for example, the case where the zeolite membrane is accommodated in the housing as in the case where the present step (A) is a separation step as described above. It may be in a place where the separation operation can be carried out, such as in the membrane separation module, or in a storage container for storing the zeolite membrane outside the membrane separation module.
- the zeolite membrane is exposed to an inert gas atmosphere to raise the temperature of the inert gas atmosphere.
- the inert gas atmosphere to which the zeolite membrane is exposed in the step (B) is heated, the temperature of the atmosphere may be lowered during the execution of the step (B) or may not be lowered. May be.
- the zeolite membrane is exposed from the viewpoint of suppressing the destruction of the zeolite membrane due to a rapid temperature drop when the hydrocarbon mixture is subjected to membrane separation using the regenerated zeolite membrane that has undergone the step (B). It is preferable to lower the temperature of the inert gas atmosphere during the implementation of the step (B).
- the inert gas atmosphere to which the zeolite membrane is exposed in the step (B) includes an atmosphere made of an inert gas such as nitrogen gas, argon gas, and helium gas. These inert gases can be used singly or in combination. Among these, nitrogen gas is preferable as the inert gas. If the inert gas atmosphere to which the zeolite membrane is exposed is a nitrogen gas atmosphere, the separation factor of the zeolite membrane can be further sufficiently increased by effectively regenerating the porosity of the zeolite membrane.
- the regenerated zeolite membrane obtained by performing the step (B) using a nitrogen gas atmosphere increases the permeability coefficient of the hydrocarbon compound that easily permeates the micropores, and the hydrocarbon compound that permeates the mesopores. The transmission coefficient can be reduced.
- the inert gas used for constituting the inert gas atmosphere to which the zeolite membrane can be exposed in the step (B) it is preferable to use an inert gas having a very low content of components other than the inert gas, It is more preferable that it is an inert gas consisting essentially of an inert gas, and it is even more preferable that no gas other than the inert gas is contained.
- “consisting essentially of an inert gas” means that 99.9% by volume or more of the inert gas is the inert gas.
- the inert gas atmosphere can contain water vapor as a component other than the inert gas.
- the dew point of the inert gas atmosphere is ⁇ 20 ° C. or lower. Is preferably ⁇ 30 ° C. or less, more preferably ⁇ 40 ° C. or less, and particularly preferably ⁇ 50 ° C. or less.
- the “dew point” refers to a dew point under atmospheric pressure determined from the amount of water measured using Fourier transform infrared spectroscopy (FT-IR).
- the maximum temperature of the inert gas atmosphere to which the zeolite membrane is exposed during the step (B) is preferably 100 ° C. or higher, more preferably 150 ° C. or higher, and further preferably 200 ° C. or higher.
- the temperature is 450 ° C. or lower, and more preferably 400 ° C. or lower.
- the temperature of the inert gas atmosphere to which the zeolite membrane is exposed during the step (B) is preferably in the range of 10 ° C. or higher and 450 ° C. or lower, and preferably in the range of 20 ° C. or higher and 450 ° C. or lower. More preferred.
- the pressure (gauge pressure) of the inert gas atmosphere to which the zeolite membrane is exposed is preferably 1 MPa or less, for example. This is because if the pressure is too high, the zeolite membrane may be damaged.
- the pressure (gauge pressure) of the inert gas atmosphere to which the zeolite membrane is exposed is usually 10 kPa or more.
- the time for which the dew point is exposed to the inert gas atmosphere in the step (B) is not particularly limited and is preferably 5 hours or more, more preferably 10 hours or more, and 15 hours. More preferably, it is usually 500 hours or less. This is because the separation factor of the regenerated zeolite membrane obtained through the step (B) can be further sufficiently increased if the time for exposing the zeolite membrane to the inert gas atmosphere is equal to or more than the above lower limit value.
- the time for exposing the zeolite membrane to the inert gas atmosphere at the highest temperature during the step (B) is not particularly limited, but is preferably 5 hours or longer, for example, 10 hours or longer.
- the separation coefficient of the regenerated zeolite membrane obtained through the step (B) can be further sufficiently increased. Because. Further, if the time during which the atmosphere to which the zeolite membrane is exposed is kept at the maximum temperature is set to the upper limit value or less, the loss of the zeolite membrane due to heat can be efficiently suppressed.
- any method for exposing the zeolite membrane to an inert gas atmosphere any method can be used as long as the atmosphere around the zeolite membrane can be changed to an inert gas atmosphere.
- the zeolite membrane may be exposed to an inert gas atmosphere by flowing an inert gas continuously or intermittently in a space in which the zeolite membrane is accommodated, or the zeolite membrane After the space in which the membrane is accommodated is replaced with an inert gas, the zeolite membrane may be exposed to an inert gas atmosphere by keeping the space airtight.
- the place which exposes a zeolite membrane to inert gas atmosphere may be in a housing or a storage container similarly to the said process (A).
- the temperature rise may be started from the beginning of the step (B) or in the middle of the step (B). May be.
- the initial stage may correspond to a ⁇ membrane pressing operation> described later.
- the temperature of the inert gas atmosphere is preferably raised to 100 ° C. or higher, more preferably raised to 150 ° C. or higher, further preferably raised to 200 ° C. or higher, and raised to 450 ° C. or lower. It is preferable to raise the temperature, and it is more preferable to raise the temperature to 400 ° C. or lower. This is because the separation factor of the regenerated zeolite membrane obtained through the step (B) can be further sufficiently increased by setting the temperature of the atmosphere after the temperature increase (temperature after the temperature increase) to the above lower limit value or more. Further, if the temperature of the atmosphere after the temperature rise (temperature after the temperature rise) is not more than the above upper limit value, it is possible to efficiently suppress the loss of the zeolite membrane due to heat.
- the time for maintaining the temperature of the atmosphere at the temperature after the temperature rise after the temperature rise is not particularly limited, but is preferably, for example, 5 hours or more, more preferably 10 hours or more, and 12 hours. More preferably, the time is 50 hours or less, and more preferably 30 hours or less.
- the separation coefficient of the regenerated zeolite membrane obtained through the step (B) can be further sufficiently increased by setting the time for maintaining the temperature at the temperature after raising the temperature to the above lower limit value or more.
- the temperature of the heated atmosphere can be arbitrarily lowered to, for example, 30 ° C. or lower, preferably 25 ° C. or lower. If the temperature of the atmosphere to which the zeolite membrane is exposed is lowered to the above upper limit value or less, when the hydrocarbon mixture is subjected to membrane separation using the regenerated zeolite membrane obtained through the step (B), a rapid temperature drop occurs. This is because the destruction of the zeolite membrane can be suppressed. Note that when the temperature of the atmosphere is lowered, the timing of ending the step (B) may be the same as the end of the temperature drop, or may be after an arbitrary time has elapsed after the temperature drop is ended.
- the membrane regeneration method of the present invention further includes a membrane pressurizing operation for pressurizing the zeolite membrane in a state where the zeolite membrane is exposed to an inert gas atmosphere in the initial stage of the step (B).
- a membrane pressurizing operation for pressurizing the zeolite membrane in a state where the zeolite membrane is exposed to an inert gas atmosphere in the initial stage of the step (B).
- the separation factor of the zeolite membrane obtained through the step (B) can be further sufficiently increased. The reason for this is not clear, but by pressing the zeolite membrane with the hydrocarbon mixture adsorbed or adhered, the hydrocarbon mixture can be "indented" closer to the inside of the porous structure of the zeolite membrane. It is guessed.
- the membrane pressurizing operation is not particularly limited as long as the zeolite membrane can be pressurized, and can be realized by any method.
- the zeolite membrane in the membrane pressurizing operation, can be pressurized by filling the space containing the zeolite membrane with an inert gas and further increasing the pressure in the space.
- the place where the film pressurizing operation which is a part of the step (B) is performed may be in the housing or in the storage container.
- the zeolite membrane in pressurizing the zeolite membrane in the membrane separation module, can be pressurized by applying a so-called “back pressure” to the zeolite membrane from the downstream side of the non-permeate side of the zeolite membrane.
- the zeolite membrane in the membrane separation module when the zeolite membrane in the membrane separation module is pressurized, the zeolite membrane can be pressurized by applying pressure to the zeolite membrane from the upstream side of the non-permeate side of the zeolite membrane.
- the differential pressure is preferably 1 MPa or less, and 700 kPa More preferably, it is more preferably 400 kPa or less, usually 10 kPa or more, and preferably 100 kPa or more.
- the pressure on the non-permeation side is preferably made higher than the pressure on the permeation side.
- the pressure of the atmosphere to which the zeolite membrane is exposed during the membrane pressurizing operation is preferably 1 MPa or less, and 700 kPa or less. More preferably, it is more preferably 400 kPa or less, and usually 10 kPa or more.
- a discharge operation for discharging the hydrocarbon mixture and the like from the space in which the zeolite membrane is accommodated is performed. It is preferable to do.
- the discharge operation is not particularly limited, and can be realized by any specific operation as long as the atmosphere around the zeolite membrane can be replaced with the inert gas that can be used in the step (B), for example. .
- any hydrocarbon discharging operation, membrane pressurizing operation, or the like can be interposed.
- the step of exposing to an atmosphere other than the hydrocarbon mixture or inert gas, such as the atmosphere or carbon dioxide atmosphere, and raising the temperature is not included.
- the membrane separation apparatus 100 includes a membrane separation module 30 having a zeolite membrane therein, a raw material supply mechanism 20 for supplying a hydrocarbon mixture to the membrane separation module 30, and an inert gas (N 2 in the illustrated example) as a membrane separation module.
- a gas supply mechanism 40 is provided for supplying a space containing 30 zeolite membranes. Then, the membrane separation apparatus 100 supplies the hydrocarbon mixture to the membrane separation module 30 using the raw material supply mechanism 20 and performs membrane separation, and then raises the temperature in an inert gas atmosphere supplied using the gas supply mechanism 40. However, the membrane separation module can be regenerated.
- the membrane separation module 30 includes a housing 31 and a zeolite membrane 32 that is accommodated in the housing 31 and defines a non-permeation side region 33 and a permeation side region 34 in the housing 31.
- a non-permeate component outflow mechanism 60 that allows non-permeate components to flow out is provided on the downstream side of the non-permeate side region 33 of the membrane separation module 30.
- the non-permeable component outflow mechanism 60 includes a non-permeable component line 61, a back pressure valve 62, and a non-permeable component line valve 63.
- the non-permeable component line 61 is connected to a non-permeable component recovery device (not shown). Or may be connected to a hydrocarbon mixture reservoir 10 to form a circulation channel.
- a gas outflow line 71 for branching out the gas supplied from the gas supply mechanism branches and extends from the non-permeating component line 61, and a gas outflow line valve 72 is provided in the gas outflow line 71.
- the gas outflow line 71 and the gas outflow line valve 72 constitute a gas outflow mechanism 70 that outflows the gas (N 2 in the illustrated example) supplied from the gas supply mechanism 40 and in contact with the zeolite membrane.
- a permeate component outflow mechanism 50 including a permeate component line for allowing permeate components to flow out is provided on the downstream side of the permeate side region 34 of the membrane separation module 30.
- the transmission component line is provided with a transmission component line valve (not shown).
- the permeation component line is connected to a permeation component recovery device (not shown) such as a cold trap.
- the raw material supply mechanism 20 is provided with a raw material line 21 that connects the hydrocarbon mixture storage tank 10 and the non-permeate side region 33 of the membrane separation module 30, and the raw material line 21 is configured to remove the hydrocarbon mixture in the storage tank 10.
- a transfer device 22 for feeding to the permeate side region 33, a heater 23 provided in the raw material line 21 for heating the hydrocarbon mixture, and a raw material line valve 24 are provided.
- the hydrocarbon mixture fed through the transfer device 22 is heated by the heater 23 by operating the transfer device 22 and the heater 23 with the raw material line valve 24 opened. Then, it can be vaporized and supplied to the non-permeate side region 33 of the membrane separation module 30. Further, according to the raw material supply mechanism 20, the supply of the hydrocarbon mixture to the non-permeate side region 33 of the membrane separation module 30 can be stopped by closing the raw material line valve 24.
- the gas supply mechanism 40 is connected to the raw material line 21 between the raw material line valve 24 and the membrane separation module 30 to connect an inert gas supply source (not shown) and the non-permeate side region 33 of the membrane separation module 30.
- the gas line 41 to connect, the gas line valve 42, and the heater 43 which is provided in the gas line 41 and heats inert gas is provided.
- the gas supply mechanism 40 by operating the heater 43 with the gas line valve 42 open, the gas is heated by the heater 43 and supplied to the non-permeate side region 33 of the membrane separation module 30. can do. Further, according to the gas supply mechanism 40, the gas supply to the non-permeate side region 33 of the membrane separation module 30 can be stopped by closing the gas line valve 42.
- the raw material line valve 24, the non-permeate component line valve 63, and the permeate component line valve (not shown) are opened, the gas line valve 42 and the gas outflow line valve 72 are closed, and the raw material The hydrocarbon mixture can be flowed from the supply mechanism 20 to the membrane separation module 30 to separate the hydrocarbon mixture.
- the vaporized hydrocarbon mixture is sent to the non-permeate side region 33 of the membrane separation module 30 through the transfer device 22 and the heater 23, and the permeated component permeated through the zeolite membrane 32 is transmitted to the permeated component outflow mechanism 50.
- the non-permeate component that has not permeated the zeolite membrane 32 can be recovered or circulated through the non-permeate component outflow mechanism 60.
- the raw material line valve 24, the non-permeating component line valve 63 and the permeating component line valve (not shown) are closed, and the gas line valve 42 and the gas outflow line valve 72 are opened.
- the inert gas can flow from the gas supply mechanism 40 to the membrane separation module 30.
- the inert gas heated by the heater 43 can be caused to flow into the housing 31 of the membrane separation module 30 so that the heated inert gas and the zeolite membrane 32 can be brought into contact with each other.
- the inert gas after coming into contact with the zeolite membrane 32 can be discharged to an arbitrary processing apparatus via the gas outflow line 71.
- the zeolite membrane 32 provided in such a membrane separation apparatus 100 can be regenerated by the membrane regeneration method of the present invention described above.
- Such a membrane separation device 100 can membrane-separate the hydrocarbon mixture using the obtained regenerated zeolite membrane 32.
- ⁇ Separation factor improvement rate> new zeolite membranes were used. Then, each of the examples, as comparative examples step (A), performs a separation process to obtain a permeate side samples S 1. Further, by using the reproduction completion zeolite membrane after a step (B), subjected to a separation step under the same conditions as step (A), to obtain a permeate side samples S 2. Then, using the permeation side samples S 1 and S 2 , a new product separation coefficient ⁇ n and a regenerated membrane separation coefficient ⁇ r were calculated according to the following formula (I). Furthermore, the separation factor improvement rate before and after the regeneration was calculated according to the following formula (II).
- X n is the content ratio [mol%] of n-pentane in the raw material
- X iso is the content ratio [mol%] of isopentane in the raw material
- Y n is a content of the permeate side samples S 1 or in S 2 of n- pentane [mol%]
- Y iso are content of isopentane in the permeate side sample S 1 or S 2 [mol%].
- Example 1 ⁇ Process (A)> A structure separating agent is formed by forming a porous separation layer made of MFI-type zeolite on the outer surface of a cylindrical mullite porous support, followed by firing in an air atmosphere having a dew point of 2 ° C. at a temperature of 500 ° C. for 20 hours.
- a separation step as step (A) was performed using a membrane separation apparatus 100 as shown in FIG.
- the permeation component line of the membrane separation apparatus 100 was connected to a sampling cold trap, and the non-permeation component line 61 was connected to the storage tank 10 via a heat exchanger as a cooler.
- the storage tank 10 is filled with a hydrocarbon mixture of 5 carbon atoms composed of a mixed liquid of n-pentane and isopentane (a mixed liquid of n-pentane: 50 mol% and isopentane: 50 mol%).
- the deaeration operation was performed three times.
- the raw material line valve 24, the non-permeate component line valve 63, and the permeate component line valve (not shown) are closed, and the gas line valve 42 and the gas outflow line valve 72 are opened.
- Nitrogen gas (dew point: ⁇ 50 ° C., introduced nitrogen gas purity: 99.99% by volume) was passed through 30 to bring the nitrogen gas into contact with the zeolite membrane 32.
- nitrogen gas heated by the heater 43 is caused to flow into the housing 31 of the membrane separation module 30 and the temperature in the housing 31 is raised to 500 ° C. (maximum temperature), and then the maximum temperature 500 is reached.
- Nitrogen gas and the zeolite membrane 32 were contacted at 15 ° C. for 15 hours. Thereafter, the temperature in the housing 31 was lowered to 20 ° C., and the nitrogen gas and the zeolite membrane 32 were contacted at a temperature of 20 ° C. for 19 hours. Thereafter, the raw material line valve 24 and the non-permeate component line valve 63 were opened, and the gas line valve 42 and the gas outflow line valve 72 were closed. Then, the hydrocarbon mixture was heated to 70 ° C.
- the system is operated until the temperature in the system reaches a steady state.
- the back pressure valve 62 pressurizes the non-permeate side to 150 kPa (gauge pressure).
- the permeation side cold trap
- the permeation component line valve (not shown) was opened, and membrane separation was started.
- membrane separation was performed under the conditions of a temperature of 70 ° C. and a differential pressure of 250 kPa between the non-permeable side and the permeable side.
- discharge operation which discharges a raw material from the system as follows was performed.
- the discharging operation first, the raw material line valve 24 was closed and the gas line valve 42 was opened, and the hydrocarbon mixture in the line was pushed out to the storage tank 10 through the non-permeating component line valve 63. Then, nitrogen gas was supplied by the gas supply mechanism 40 until the pressure in 100 became 150 kPa, the pressure inside the system was increased, and a pressure release valve (not shown) was opened to release pressure from the storage tank 10. After the operation from the pressure increase to the pressure release was repeated four times, the non-permeate component line valve 63 was closed, the gas outflow line valve 72 was opened again, and supply of nitrogen gas (that is, nitrogen purge) was started.
- nitrogen gas that is, nitrogen purge
- a membrane pressurizing step was performed as follows. First, after starting the nitrogen purge, the back pressure valve 62 was opened and a back pressure of 100 kPa (gauge pressure) was applied to the non-permeating side. At this time, the pressure on the permeation side (cold trap) was kept at ⁇ 100 kPa (gauge pressure). That is, in the film pressurizing step, the differential pressure between the non-permeable side and the permeable side was set to 200 kPa. This state was maintained for 10 minutes.
- step (B) the nitrogen gas was heated while exposing the zeolite membrane 32 to nitrogen gas as an inert gas. Specifically, nitrogen gas (dew point: ⁇ 50 ° C., introduced nitrogen gas purity: 99.99 vol%) from the gas supply mechanism 40 to the membrane separation module 30 with the gas line valve 42 and the gas outflow line valve 72 opened. ) And nitrogen gas and the zeolite membrane 32 were brought into contact with each other. Specifically, nitrogen gas heated by the heater 43 is caused to flow into the housing 31 of the membrane separation module 30 and the temperature in the housing 31 is raised to 250 ° C. (maximum temperature), and then the maximum temperature 250 is reached. Nitrogen gas and the zeolite membrane 32 were contacted at 15 ° C.
- Example 2 A regenerated zeolite membrane was obtained in the same manner as in Example 1 except that the maximum temperature in the housing 31 in the step (B) was changed to 300 ° C. Using the obtained regenerated zeolite membrane, the separation factor and the improvement factor of the separation factor were evaluated according to the above method. The results are shown in Table 1.
- step (B) of Example 1 the atmosphere to which the zeolite membrane was exposed was raised using air having a dew point of 20 ° C. instead of nitrogen gas, and the zeolite membrane was held at a maximum temperature of 250 ° C. for 10 hours.
- the temperature lowering operation was performed after interposing a drying operation in which the atmosphere exposed to was maintained at 250 ° C. as a nitrogen gas atmosphere for 5 hours. Except for these points, a regenerated zeolite membrane was obtained in the same manner as in Example 1.
- the separation factor and the improvement factor of the separation factor were evaluated according to the above method. The results are shown in Table 1.
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- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
L'invention concerne un procédé de régénération de film pour régénérer un film qui est approprié pour une utilisation dans la séparation de certains hydrocarbures d'un mélange d'hydrocarbures. Plus spécifiquement, l'invention concerne un procédé de régénération de film qui comprend : une étape (A) dans laquelle un mélange d'hydrocarbures est mis en contact avec un film à zéolite; et une étape (B) le film à zéolite étant exposé à une atmosphère de gaz inerte et la température de l'atmosphère de gaz inerte étant augmentée.
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Cited By (3)
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WO2020136718A1 (fr) * | 2018-12-25 | 2020-07-02 | 日揮グローバル株式会社 | Dispositif de séparation de gaz non hydrocarboné et procédé de régénération de membrane de séparation inorganique |
JP2021028054A (ja) * | 2019-08-09 | 2021-02-25 | 三菱ケミカル株式会社 | ゼオライト膜複合体の再生方法 |
JP2022551428A (ja) * | 2019-09-25 | 2022-12-09 | コリア ユニバーシティ リサーチ アンド ビジネス ファウンデーション | メソ孔が含まれた階層構造の分離膜、その製造方法及びそれを用いたキシレンの分離方法 |
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US20130000484A1 (en) * | 2010-03-04 | 2013-01-03 | Paul Jason Williams | Method of separating gas mixtures |
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US20130000484A1 (en) * | 2010-03-04 | 2013-01-03 | Paul Jason Williams | Method of separating gas mixtures |
JP2016534112A (ja) * | 2013-08-20 | 2016-11-04 | エルジー・ケム・リミテッド | イソプロピルアルコールの精製方法 |
US20160008753A1 (en) * | 2014-06-20 | 2016-01-14 | Exxonmobil Research And Engineering Company | Separation and Storage of Fluids Using ITQ-55 |
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WO2020136718A1 (fr) * | 2018-12-25 | 2020-07-02 | 日揮グローバル株式会社 | Dispositif de séparation de gaz non hydrocarboné et procédé de régénération de membrane de séparation inorganique |
US11801478B2 (en) | 2018-12-25 | 2023-10-31 | Jgc Corporation | Non-hydrocarbon gas separation device and inorganic separation membrane regeneration method |
JP2021028054A (ja) * | 2019-08-09 | 2021-02-25 | 三菱ケミカル株式会社 | ゼオライト膜複合体の再生方法 |
JP7358827B2 (ja) | 2019-08-09 | 2023-10-11 | 三菱ケミカル株式会社 | ゼオライト膜複合体の再生方法 |
JP2022551428A (ja) * | 2019-09-25 | 2022-12-09 | コリア ユニバーシティ リサーチ アンド ビジネス ファウンデーション | メソ孔が含まれた階層構造の分離膜、その製造方法及びそれを用いたキシレンの分離方法 |
JP7480283B2 (ja) | 2019-09-25 | 2024-05-09 | コリア ユニバーシティ リサーチ アンド ビジネス ファウンデーション | メソ孔が含まれた階層構造の分離膜、その製造方法及びそれを用いたキシレンの分離方法 |
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