WO2020130954A1 - Adsorbant de réseau métallo-organique - Google Patents

Adsorbant de réseau métallo-organique Download PDF

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Publication number
WO2020130954A1
WO2020130954A1 PCT/TH2019/000068 TH2019000068W WO2020130954A1 WO 2020130954 A1 WO2020130954 A1 WO 2020130954A1 TH 2019000068 W TH2019000068 W TH 2019000068W WO 2020130954 A1 WO2020130954 A1 WO 2020130954A1
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WO
WIPO (PCT)
Prior art keywords
metal
organic framework
copper
framework according
sample
Prior art date
Application number
PCT/TH2019/000068
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English (en)
Inventor
Taradon PIROMCHART
Kittipong CHAINOK
Original Assignee
Ptt Exploration And Production Public Company Limited
Kit Chemicals (Thailand) Co., Ltd.
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Application filed by Ptt Exploration And Production Public Company Limited, Kit Chemicals (Thailand) Co., Ltd. filed Critical Ptt Exploration And Production Public Company Limited
Publication of WO2020130954A1 publication Critical patent/WO2020130954A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/33—Polycyclic acids
    • C07C63/337—Polycyclic acids with carboxyl groups bound to condensed ring systems
    • C07C63/34—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings
    • C07C63/38—Polycyclic acids with carboxyl groups bound to condensed ring systems containing two condensed rings containing two carboxyl groups both bound to carbon atoms of the condensed ring system
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
    • B01J20/223—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material containing metals, e.g. organo-metallic compounds, coordination complexes
    • B01J20/226—Coordination polymers, e.g. metal-organic frameworks [MOF], zeolitic imidazolate frameworks [ZIF]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
    • C07C63/14—Monocyclic dicarboxylic acids
    • C07C63/15—Monocyclic dicarboxylic acids all carboxyl groups bound to carbon atoms of the six-membered aromatic ring
    • C07C63/26—1,4 - Benzenedicarboxylic acid
    • C07C63/30—Halides thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G25/00—Refining of hydrocarbon oils in the absence of hydrogen, with solid sorbents
    • C10G25/003—Specific sorbent material, not covered by C10G25/02 or C10G25/03
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2253/00—Adsorbents used in seperation treatment of gases and vapours
    • B01D2253/20—Organic adsorbents
    • B01D2253/204—Metal organic frameworks (MOF's)
    • 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D2257/00—Components to be removed
    • B01D2257/30—Sulfur compounds
    • B01D2257/304—Hydrogen sulfide
    • 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
    • B01D2257/502—Carbon monoxide
    • 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
    • B01D2257/00—Components to be removed
    • B01D2257/60—Heavy metals or heavy metal compounds
    • B01D2257/602—Mercury or mercury compounds
    • 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
    • B01D53/02—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 adsorption, e.g. preparative gas chromatography
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/205—Metal content
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
    • C10G2300/20—Characteristics of the feedstock or the products
    • C10G2300/201—Impurities
    • C10G2300/207—Acid gases, e.g. H2S, COS, SO2, HCN
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02C—CAPTURE, STORAGE, SEQUESTRATION OR DISPOSAL OF GREENHOUSE GASES [GHG]
    • Y02C20/00—Capture or disposal of greenhouse gases
    • Y02C20/40—Capture or disposal of greenhouse gases of CO2
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/151—Reduction of greenhouse gas [GHG] emissions, e.g. CO2

Definitions

  • This invention relates to a metal organic framework adsorbent for removing contaminants from petroleum fluid.
  • the petroleum fluid obtained from drilling wells normally contains a mixture of gas including CO2, NO , So x , water, condensate, and contaminants including mercury (Hg) and arsenic (As). These contaminants can cause many drawbacks to the operations, such as corrosion and process fouling. Accordingly, there are many researches on removing CO2, and mercury Hg and As from the petroleum product in order to obtain the petroleum product with less impurities before feeding to other units.
  • Metal-organic framework is a crystalline material constructed from metal- containing nodes and linkers. Combinations of properties of a metal part and organic linker part in the same structure lead to special properties such as designable porosity, internal pore surface functionality, and high surface area. This makes MOFs an interesting material for many applications including, but not limited to, adsorbents, gas storage, chemical separations, chemical sensing and catalysis, ion exchange, light harvesting, and drug delivery.
  • MOF iron carboxylate metal-organic frameworks
  • MOFs metal-organic frameworks
  • BDC metal-organic frameworks
  • BDC 1,4-benzenedicarboxylate
  • para-disubstituted alkylaromatics such as p-xylene from an isomer mixture.
  • MOFs Their unique structure of MOFs contains octahedral cages, which can separate molecules based on differences in packing and interaction with the pore walls, as well as smaller tetrahedral cages, which are capable of separating molecules by molecular sieving.
  • BPDC Zn 2
  • BPEE 4.4-biphenyldicarboxylic acid
  • BPPE 1,2- bis(4-pyridyl)ethylene
  • This porous MOF is solvothermally synthesized by mixing Zn 2 (N0 3 )-6H 2 0, H 2 BDPC, and BPEE at molar ratio of 1 : 1 : 1 in 15 mL of dimethylformamide (DMF) and heating at 165 °C. for 3 days.
  • DMF dimethylformamide
  • the present invention provides a metal-organic framework that is suitable for the removal of CO2 and other contaminants such as Hg, As, and hydrogen sulfide (H2S) from the petroleum fluid with a high performance.
  • the metal-organic framework has a chemical formula:
  • n, n, x and y are independently selected from an integer of 1 to 5.
  • the metal-organic framework according to the present invention is obtained from a method comprising steps of: i) mixing copper (II) salt (Cu 2+ ) and 1,2,4,5-tetrabromobenzenedicarboxylic acid (Br 4 BDC), methanol (CH 3 OH) and water together; and ii) heating the mixture from step i) and collecting product. wherein the mixture from step ii) is heated at temperature in the range of 90 to 130 °C. for 1 to 3 days.
  • Figure 1 shows green plate- shaped single crystals of Sample 1.
  • Figure 2 shows FT-IR spectrum of Sample 1.
  • Figure 3 shows PXRD pattern of Sample 1.
  • Figure 4 shows asymmetric unit of Sample 1.
  • Figure 5 shows 3 D framework structure of Sample 1.
  • Figure 6 shows Brunauer-EmmetWTeller surface area of Sample 1.
  • Figure 7 shows thermal stability (TGA curve) of Sample 1.
  • Figure 8 shows mercury adsorption performance of Sample 1.
  • the present invention provides a metal organic framework (MOF) that is suitable for the removal of CO2 and other contaminants such as Hg, As, and hydrogen sulfide (H2S) from the petroleum fluid with a high performance.
  • MOF metal organic framework
  • Hg As
  • H2S hydrogen sulfide
  • Equipment, apparatus, methods, or chemicals mentioned here means equipment, apparatus, processes, or chemicals commonly operated or used by those skilled in the art, unless explicitly stated otherwise that they are equipment, apparatus, methods, or chemicals specifically used in this invention.
  • the present invention provides a metal-organic framework having a chemical formula:
  • n, n and x are independently selected from an integer of 1 to 5.
  • the metal-organic framework having a chemical formula:
  • n is selected from an integer of 1 to 2;
  • n is selected from an integer of 1 to 2;
  • x is selected from an integer of 1 to4.
  • the metal-organic framework having a chemical formula:
  • the metal-organic framework according to the present invention is obtained from a method comprising steps of: i) mixing copper (II) salt (Cu 2+ ) and 1 ,2,4,5-tetrabromobenzenedicarboxylic acid (Br 4 BDC), methanol (CH 3 OH) and water together; and ii) heating the mixture from step i) and collecting product. wherein the mixture from step ii) is heated at temperature in the range of 90 to 130 °C. for 1 to 3 days.
  • the salt of copper is selected from copper (II) nitrate, copper (II) chloride, copper (II) sulfate, copper (II) acetate, or a mixture thereof.
  • the salt of copper is copper (II) nitrate.
  • a mole ratio of the salt of copper and 1 , 2,4,5- tetrabromobenzenedicarboxylic acid (Br 4 BDC) is 4:1 to 6: 1 .
  • a mole ratio of methanol (CH 3 OH) and H 2 O is 4:1 to 6:1
  • step i) 0.05 to 0.15 mole of benzene- 1,3,5 - tricarboxylic acid (TMA) is further added into the mixture.
  • TMA benzene- 1,3,5 - tricarboxylic acid
  • the mixture of step ii) is heated at temperature in the range of 100 to 125 OC. for 1.5 to 2.5 days.
  • the mole ratio between the metal-organic framework according to the present invention can be used for removing mercury vapor, hydrogen sulfide, carbon dioxide gas, carbon monoxide, or the combination thereof from petroleum fluid.
  • the metal-organic framework according to the present invention can be used for removing mercury vapor, hydrogen sulfide, carbon dioxide gas, carbon monoxide, or the combination thereof from petroleum fluid by an adsorption between the petroleum fluid and the metal-organic framework.
  • the metal-organic framework according to the present invention can be used for adsorbing mercury vapor, carbon dioxide, or the combination thereof from petroleum fluid.
  • bipy is 2, 2 '-Bipyridine
  • Attenuated Total Reflection-Fourier Transform Infrared Spectroscopy (ATR- FTIR) spectrum of Sample 1 was recorded in the region of 650 to 4,000 cm 1 .
  • the broad band around 3,400 to 3,500 cm 1 was assigned to the OH characteristic stretching vibration of hydroxy group.
  • the asymmetric stretching bands about 1,640 to 1,550 cm 1 were assigned to the carboxylate groups of Br4BDC or formate.
  • the symmetric vibrations of the carboxylate group was at about 1,400 to 1,363 cm 1 .
  • No characteristic absorption band of any protonated forms of carboxylic group was observed between about 1,715 and 1,680 cm 1 .
  • the bands at around l,580to 1,600 cm 1 were C-C stretches of the aromatic ring.
  • Powder X-ray diffraction (PXRD), and single crystal X-ray diffraction) of Sample 1 were investigated.
  • PXRD pattern of Sample 1 indicated that the bulk of Sample 1 was a highly pure crystalline product, since sharp peaks are observed from the PXRD pattern.
  • SCXRD a summary of crystal data of obtained MOF shows in Table 2. It implied that Sample 1 crystallized in the monoclinic crystal with I2/a space group.
  • the asymmetric unit of Sample 1 consisted of 1 copper ion, half of Br4BDC ligand and 1 coordination of MeOH molecule as shown in Figure 4.
  • the three dimensional framework structure had different porous sizes in the range of about 0.7 to 1.0 nm.
  • the Cu position would be empty and could act as an active site, potentially suitable for chemical reaction or molecule capture.
  • Sample 1 was activated by soaking in acetone at room temperature for about 7 days then heating under vacuum at about 100 °C overnight.
  • the testing condition was at N2 loading about 0.047 cm 3 (STP) g _1 , at about 77 K, and about 1 bar.
  • STP 0.047 cm 3
  • Sample 1 had the type-I sorption isotherm.
  • the Brunauer-Emmett-Teller surface area of Sample 1 was 5.65 cm 2 g _1 and a mean pore width of Sample 1 was about 17.77 A (based on Horvath-Kawazoe mode).
  • thermal stability was investigated by thermal analysis in the temperature range 25 to 1000 °C under nitrogen atmosphere. As shown in Figure 7, the host framework of Sample 1 was collapsed after temperature o f about 320 °C. The decomposition of the Br4BDC ligand occurs at about 350 °C. A minor weight loss at about 25 to 200 °C, was attributed to the loss of methanol. The final residual product was possibly CuO.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (AREA)
  • Analytical Chemistry (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)

Abstract

Dans un mode de réalisation, la présente invention concerne un réseau métallo-organique qui est approprié pour l'élimination de CO2 et d'autres contaminants tels que Hg, As, et du sulfure d'hydrogène (H2S) à partir de fluide pétrolier avec des performances élevées. Le réseau métallo-organique a une formule chimique : — [Cum(Br4BDC)n(MeOH)x]— où m, n, x et y sont indépendamment choisis parmi un nombre entier de 1 à 5.
PCT/TH2019/000068 2018-12-21 2019-12-20 Adsorbant de réseau métallo-organique WO2020130954A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
TH1801007935 2018-12-21
TH1801007935 2018-12-21

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WO2020130954A1 true WO2020130954A1 (fr) 2020-06-25

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8758482B2 (en) * 2011-05-02 2014-06-24 Rutgers, The State University Of New Jersey Methods and compositions for removing carbon dioxide from a gaseous mixture
US8926736B2 (en) * 2008-06-11 2015-01-06 Centre National De La Recherche Scientifique -Cnrs- Reducible porous crystalline hybrid solid for the separation of mixtures of molecules having different degrees and/or a different number of unsaturations

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8926736B2 (en) * 2008-06-11 2015-01-06 Centre National De La Recherche Scientifique -Cnrs- Reducible porous crystalline hybrid solid for the separation of mixtures of molecules having different degrees and/or a different number of unsaturations
US8758482B2 (en) * 2011-05-02 2014-06-24 Rutgers, The State University Of New Jersey Methods and compositions for removing carbon dioxide from a gaseous mixture

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
JERMAINE A. SMITH, SINGH-WILMOT MARVADEEN A., CARTER KOREY P., CAHILL CHRISTOPHER L., RIDENOUR JAMES A.: "Lanthanide-2,3,5,6-Tetrabromoterephthalic Acid Metal-Organic Frameworks: Evolution of Halogen Halogen Interactions across the Lanthanide Series and Their Potential as Selective Bifunctional Sensors for the Detection of Fe3+, Cu2+, and Nitroaromatics", CRYSTAL GROWTH & DESIGN, vol. 19, no. 1, 20 November 2018 (2018-11-20), pages 305 - 319, XP055719573, Retrieved from the Internet <URL:https://pubs.acs.org/doi/abs/10.1021/acs.cgd.8b01426#> [retrieved on 20200409] *
XIAO ET AL.: "Syntheses and Crystal Structures of Two Cu( II ) Coordination Complexes Based on 2,3,5,6-Tetrabromoterephthalic Acid", CHINESE JOURNAL OF INORGANIC CHEMISTRY, September 2014 (2014-09-01), Retrieved from the Internet <URL:http://en.cnki.com.cn/Article-en/CJFDTotal-WJHX20140902l.htm> [retrieved on 20200409] *

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