WO2018222255A1 - Polymer blended membranes for sour gas separation - Google Patents

Polymer blended membranes for sour gas separation Download PDF

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Publication number
WO2018222255A1
WO2018222255A1 PCT/US2018/024299 US2018024299W WO2018222255A1 WO 2018222255 A1 WO2018222255 A1 WO 2018222255A1 US 2018024299 W US2018024299 W US 2018024299W WO 2018222255 A1 WO2018222255 A1 WO 2018222255A1
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WO
WIPO (PCT)
Prior art keywords
pebax
membrane
poly
weight
amide
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.)
Ceased
Application number
PCT/US2018/024299
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English (en)
French (fr)
Inventor
Junyan YANG
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Saudi Arabian Oil Co
Aramco Services Co
Original Assignee
Saudi Arabian Oil Co
Aramco Services Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Saudi Arabian Oil Co, Aramco Services Co filed Critical Saudi Arabian Oil Co
Priority to KR1020197038502A priority Critical patent/KR20200015914A/ko
Priority to CN201880036436.2A priority patent/CN111542384B/zh
Priority to JP2019564505A priority patent/JP6944543B2/ja
Priority to EP18717796.9A priority patent/EP3634609A1/en
Publication of WO2018222255A1 publication Critical patent/WO2018222255A1/en
Priority to SA519410667A priority patent/SA519410667B1/ar
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D53/00—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols
    • B01D53/22—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion
    • B01D53/228—Separation of gases or vapours; Recovering vapours of volatile solvents from gases; Chemical or biological purification of waste gases, e.g. engine exhaust gases, smoke, fumes, flue gases, aerosols by diffusion characterised by specific membranes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002—Organic membrane manufacture
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002—Organic membrane manufacture
    • B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
    • B01D67/0011—Casting solutions therefor
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002—Organic membrane manufacture
    • B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
    • B01D67/0013—Casting processes
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0002—Organic membrane manufacture
    • B01D67/0009—Organic membrane manufacture by phase separation, sol-gel transition, evaporation or solvent quenching
    • B01D67/0016—Coagulation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D67/00—Processes specially adapted for manufacturing semi-permeable membranes for separation processes or apparatus
    • B01D67/0081—After-treatment of organic or inorganic membranes
    • B01D67/009—After-treatment of organic or inorganic membranes with wave-energy, particle-radiation or plasma
    • 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
    • B01D71/06—Organic material
    • B01D71/40—Polymers of unsaturated acids or derivatives thereof, e.g. salts, amides, imides, nitriles, anhydrides, esters
    • B01D71/401—Polymers based on the polymerisation of acrylic acid, e.g. polyacrylate
    • 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
    • B01D71/06—Organic material
    • B01D71/52—Polyethers
    • 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
    • B01D71/06—Organic material
    • B01D71/52—Polyethers
    • B01D71/521—Aliphatic polyethers
    • 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
    • B01D71/06—Organic material
    • B01D71/52—Polyethers
    • B01D71/521—Aliphatic polyethers
    • B01D71/5211—Polyethylene glycol or polyethyleneoxide
    • 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
    • B01D71/06—Organic material
    • B01D71/56—Polyamides, e.g. polyester-amides
    • 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
    • B01D71/06—Organic material
    • B01D71/76—Macromolecular material not specifically provided for in a single one of groups B01D71/08 - B01D71/74
    • B01D71/80—Block polymers
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2256/00—Main component in the product gas stream after treatment
    • B01D2256/24—Hydrocarbons
    • B01D2256/245—Methane
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/50—Carbon oxides
    • B01D2257/504—Carbon dioxide
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/08—Specific temperatures applied
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/12—Specific ratios of components used
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/15—Use of additives
    • B01D2323/218—Additive materials
    • B01D2323/2182—Organic additives
    • B01D2323/21839—Polymeric additives
    • B01D2323/2185—Polyethylene glycol
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/30—Cross-linking
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/34—Use of radiation
    • B01D2323/345—UV-treatment
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2323/00—Details relating to membrane preparation
    • B01D2323/52—Use of a mould
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/22—Thermal or heat-resistance properties
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/24—Mechanical properties, e.g. strength
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2325/00—Details relating to properties of membranes
    • B01D2325/32—Melting point or glass-transition temperatures

Definitions

  • FIG. 5 is Thermogravimetric Analyzer (TGA) thermograms of the percent weight loss as a function of temperature in degrees Celsius of: (3) neat Pebax®; (2) Pebax®/PEGDA; and (1) Pebax®/XLPEGDA membranes.
  • TGA Thermogravimetric Analyzer
  • FIG. 6 is a graph of C0 2 permeability (Barrer) of (3) neat Pebax® and (1) Pebax®/XLPEGDA membranes versus the feed pressure (50 pounds per square inch (psi) to 500 psi).
  • FIG. 7 is a graph of relative C0 2 permeability (P p /Pso ps i) versus the feed pressure (50 psi to 500 psi), in which the relative C0 2 permeability equals the permeability at given pressure divided by the permeability at 50 psi.
  • FIG. 8A is a curve of swelling resistance of percent weight loss as a function of time in minutes of: (2) Pebax®/PEGDA; and (1) Pebax®/XLPEGDA membranes in water.
  • FIG. 8B is a curve of swelling resistance of percent weight loss as a function of time in minutes of: (2) Pebax®/PEGDA; and (1) Pebax®/XLPEGDA membranes in hexane.
  • each R is independently a -CH 3 (methyl) or -H (hydrogen radical), and subscript n is an integer from 2 to 30. In some embodiments, the subscript n is an integer from 2 to 14.
  • methods of making a gas separation membrane include dissolving a poly(ether- ⁇ -amide) (PEBA) copolymer, an acrylate-terminated PEG according to formula (I) or formula (II), and a photoinitiator in a solvent to form a polymer solution.
  • PEBA poly(ether- ⁇ -amide)
  • acrylate-terminated PEG chains By incorporating and crosslinking acrylate-terminated PEG chains within PEBA polymer solution, interpenetrating polymer networks are formed.
  • the polymer solution is casted or placed in a mold. In some embodiments, the polymer solution is casted at a temperature from 30 °C to 80 °C.
  • a film is formed. The film may optionally be removed from the mold. The film is then exposed to a photoactivator to form the gas separation membrane.
  • the gas separation membrane optionally may be cured.
  • terminal refers to a carbon-carbon double bond in which one of the carbon atoms in the double bond is at the end of the chain, and therefore is bonded to two hydrogen atoms.
  • the two types of polymers are dissolved in a solvent and mixed at a temperature from 70 °C to 100 °C.
  • the solvent may be a mixture of various solvents such as water; alcohol; dimethylfuran; dimethylacetamide; and dimethyl sulfoxide (DMSO).
  • the solvent is a mixture of water and alcohol.
  • the water is deionized water and the alcohol may be chosen from ethanol, methanol, propanol, z ' so-propanol, butanol, or combinations thereof.
  • the alcohol is ethanol.
  • the photoinitiator may include ketone compositions such as 1- hydroxycyclohexyl phenyl ketone (HCPK) or benzophenone.
  • HCPK 1- hydroxycyclohexyl phenyl ketone
  • the photoinitiator may be added in amounts of from 0.5 wt.% to 5.0 wt.%, 0.5 wt.% to 3.0 wt.%, or 1.0 wt. % to 2 wt. % based on the total weight of the acrylate-terminated PEG.
  • the film is exposed to a photoactivator to facilitate crosslinking and thereby form the gas separation membrane.
  • the photoactivator can be any light source that activates the photoinitiator and causes the photoinitiator to react with the acrylate-terminated PEG.
  • the photoactivator is ultraviolet light at a wavelength of from 300 nm to 350 nm or 315 nm to 320 nm.
  • the film is exposed to ultraviolet light of 318 nm.
  • the exposure time may range from 30 seconds to 300 seconds or from 90 seconds to 180 seconds.
  • the light intensity may vary from 11,000 mW/cm to 12,000 mW/cm (milliwatt per centimeters squared).
  • the gas separation membrane has other structural benefits. For examples, as the pressure increase, the C0 2 permeability does not increase as much as other gas separation membrane and has approximately 50% less C0 2 permeability increase. This indicates that the gas separation membrane of this disclosure is more plasticization resistant. Additionally, the gas separation membrane does not swell or leech in comparison to non-crosslinked membranes having similar composition. In some embodiments, the gas separation membrane achieves a greater than 100% reduction in weight loss than uncrosslinked poly(ether-b-amide) copolymers. In other embodiments, the gas separation membrane achieves a greater than 250%, 500%, 750% or 1000% reduction in weight loss than uncrosslinked poly(ether-b-amide) copolymers.
  • Pebax 1657 was dried in a vacuum oven at 60 °C for 24 hours.
  • a sample of 0.8 g of dried Pebax 1657 was dissolved in a mixture of 20 mL ethanol/deionized (DI) water (70/30 v/v).
  • DI ethanol/deionized
  • the reaction mixture was vigorously stirred at 85 °C under reflux for at least 6 hour to obtain a homogeneous solution.
  • the obtained Pebax solution was placed at 50-60 °C to remove gas bubbles and then was poured within pre-heated (50 to 60 °C) polytetrafluoroethylene (PTFE) flat-bottomed Petri dishes to prepare the dense film.
  • the dense film was dried at room temperature overnight with a cover for solvent evaporation, and then dried in a vacuum oven at 60 °C for 48hr. Subsequent to that the membranes were easily peeled off the Petri dishes for permeation testing.
  • Pebax 1657 was dried in a vacuum oven at 60 °C for 24 hours. A sample of 0.8 g of dried Pebax 1657 was dissolved in a mixture of 20 mL ethanol/deionized (DI) water (70/30 v/v). The reaction mixture was vigorously stirred at 85 °C under reflux for at least 6 hour to obtain a homogeneous solution.
  • DI ethanol/deionized
  • PEGDA polyethylene glycol diacrylate
  • the PEGDA showed characteristics of a plasticizer behavior in that a plasticizer decreases intermolecular forces such as hydrogen bonding (H-bonding).
  • H-bonding hydrogen bonding
  • the membrane thermal properties were characterized by Differential Scanning Calorimetry (DSC).
  • the thermographs, FIG. 3 A (the heating curves) and FIG. 3B (cooling curves) of neat Pebax and the prepared blended membranes were shown in FIGS. 3A-3B.
  • Glass transition temperature (T g ), melting temperature (T m ) of polyamide hard (PA) and polyether soft (PE) segments of neat Pebax and the prepared blended membranes are shown in Table 3.
  • T g Glass transition temperature
  • T m melting temperature
  • PET m melting temperature
  • PE polyether soft

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Dispersion Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Plasma & Fusion (AREA)
  • Inorganic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Separation Using Semi-Permeable Membranes (AREA)
  • Graft Or Block Polymers (AREA)
PCT/US2018/024299 2017-05-30 2018-03-26 Polymer blended membranes for sour gas separation Ceased WO2018222255A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
KR1020197038502A KR20200015914A (ko) 2017-05-30 2018-03-26 사워 가스 분리를 위한 중합체 블렌딩된 멤브레인
CN201880036436.2A CN111542384B (zh) 2017-05-30 2018-03-26 用于酸气分离的聚合物共混膜
JP2019564505A JP6944543B2 (ja) 2017-05-30 2018-03-26 サワーガス分離用ポリマーブレンド膜
EP18717796.9A EP3634609A1 (en) 2017-05-30 2018-03-26 Polymer blended membranes for sour gas separation
SA519410667A SA519410667B1 (ar) 2017-05-30 2019-11-28 أغشية مولفة من البوليمر لفصل الغاز الحامض

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15/608,403 US10525406B2 (en) 2017-05-30 2017-05-30 Polymer blended membranes for sour gas separation
US15/608,403 2017-05-30

Publications (1)

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WO2018222255A1 true WO2018222255A1 (en) 2018-12-06

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PCT/US2018/024299 Ceased WO2018222255A1 (en) 2017-05-30 2018-03-26 Polymer blended membranes for sour gas separation

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US (2) US10525406B2 (cg-RX-API-DMAC10.html)
EP (1) EP3634609A1 (cg-RX-API-DMAC10.html)
JP (1) JP6944543B2 (cg-RX-API-DMAC10.html)
KR (1) KR20200015914A (cg-RX-API-DMAC10.html)
CN (1) CN111542384B (cg-RX-API-DMAC10.html)
SA (1) SA519410667B1 (cg-RX-API-DMAC10.html)
SG (1) SG10201914008WA (cg-RX-API-DMAC10.html)
WO (1) WO2018222255A1 (cg-RX-API-DMAC10.html)

Cited By (5)

* Cited by examiner, † Cited by third party
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JP2020532419A (ja) * 2017-08-30 2020-11-12 サウジ アラビアン オイル カンパニーＳａｕｄｉ Ａｒａｂｉａｎ Ｏｉｌ Ｃｏｍｐａｎｙ ガス分離のための架橋ポリマーブレンド膜
WO2021009463A1 (fr) 2019-07-15 2021-01-21 Arkema France Copolymères à blocs rigides polyamides et blocs souples comprenant du polyéthylène glycol
WO2022147579A1 (en) * 2021-01-04 2022-07-07 Saudi Arabian Oil Company Co2-philic crosslinked polyethylene glycol-based membranes for acid and sour gas separations
EP4559953A1 (en) 2023-11-21 2025-05-28 Arkema France Copolymers with polyamide blocks and flexible blocks
WO2025108985A1 (en) 2023-11-21 2025-05-30 Arkema France Copolymers with polyamide blocks and flexible blocks

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US10525406B2 (en) * 2017-05-30 2020-01-07 Saudi Arabian Oil Company Polymer blended membranes for sour gas separation
US11148103B2 (en) * 2019-12-03 2021-10-19 Saudi Arabian Oil Company Gas separation membrane comprising crosslinked blends of rubbery polymers
CN112619434A (zh) * 2020-12-02 2021-04-09 石河子大学 一种聚醚胺共混改性橡胶态高分子共混膜的制备及应用

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