CN106866985B - A kind of metal-organic framework materials and preparation method thereof separated for acetylene and methane adsorption - Google Patents
A kind of metal-organic framework materials and preparation method thereof separated for acetylene and methane adsorption Download PDFInfo
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- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 239000000463 material Substances 0.000 title claims abstract description 41
- 239000012621 metal-organic framework Substances 0.000 title claims abstract description 35
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- 238000001179 sorption measurement Methods 0.000 title claims abstract description 11
- 239000013110 organic ligand Substances 0.000 claims abstract description 14
- NGDQQLAVJWUYSF-UHFFFAOYSA-N 4-methyl-2-phenyl-1,3-thiazole-5-sulfonyl chloride Chemical compound S1C(S(Cl)(=O)=O)=C(C)N=C1C1=CC=CC=C1 NGDQQLAVJWUYSF-UHFFFAOYSA-N 0.000 claims abstract description 5
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 9
- 125000000524 functional group Chemical group 0.000 abstract description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract description 3
- 239000013336 microporous metal-organic framework Substances 0.000 abstract description 3
- 210000003850 cellular structure Anatomy 0.000 abstract 1
- 150000002394 hexacarboxylic acid derivatives Chemical class 0.000 abstract 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N hexane carboxylic acid Natural products CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 10
- 238000000926 separation method Methods 0.000 description 8
- 238000010521 absorption reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 6
- 239000003345 natural gas Substances 0.000 description 5
- 238000005336 cracking Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BEDFIBPNPHRGDO-UHFFFAOYSA-N yttrium;hydrate Chemical compound O.[Y] BEDFIBPNPHRGDO-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000003317 industrial substance Substances 0.000 description 2
- -1 methane Alkynes Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- SXFQCTMHFJARRW-UHFFFAOYSA-N acetylene;methane Chemical compound C.C#C SXFQCTMHFJARRW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 150000003746 yttrium Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
- C08G83/008—Supramolecular polymers
-
- 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
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
- C10L3/00—Gaseous fuels; Natural gas; Synthetic natural gas obtained by processes not covered by subclass C10G, C10K; Liquefied petroleum gas
- C10L3/06—Natural gas; Synthetic natural gas obtained by processes not covered by C10G, C10K3/02 or C10K3/04
- C10L3/10—Working-up natural gas or synthetic natural gas
-
- 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)
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/702—Hydrocarbons
- B01D2257/7022—Aliphatic hydrocarbons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D2257/00—Components to be removed
- B01D2257/70—Organic compounds not provided for in groups B01D2257/00 - B01D2257/602
- B01D2257/702—Hydrocarbons
- B01D2257/7022—Aliphatic hydrocarbons
- B01D2257/7025—Methane
-
- 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
- Y02C20/20—Capture or disposal of greenhouse gases of methane
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- Chemical & Material Sciences (AREA)
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- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Analytical Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Inorganic Chemistry (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The present invention relates to Inorganic-organic Hybrid Material technical field, specific a kind of novel microporous metal-organic framework materials and the preparation method and application thereof.The preparation method uses the hexacarboxylic acid for containing equal ipazine (s-heptazine) and imino group functional group as reaction organic ligand, reacts to obtain a kind of novel microporous metal-organic framework materials under hydrothermal conditions with yttrium nitrate.Had uniformly and the cellular structure of rule and excellent acetylene and methane adsorption separating capacity using the micropore metal organic framework material that the preparation method obtains.
Description
Technical field
The present invention relates to Inorganic-organic Hybrid Material technical field, a kind of specific micropore metal organic framework material and its system
Preparation Method and application.
Background technique
Energy crisis is solved by global extensive concern, energy shortage problems demand in recent years.Although new energy skill
Art is by positive research and development and utilization, but fossil energy (such as coal, oil and natural gas) is still the main energy of human society
Source, the service efficiency for how improving fossil energy become the key to solve the problem approach.Methane is the main component of natural gas, no
It is only the common clean fuel of life, or a kind of important industrial chemicals.However impurity in methane (such as other alkane, alkene,
Alkynes and non-hydrocarbon gas) presence will affect use and the transformation efficiency of methane.In addition, methane cracking acetylene is industrially to make
A kind of common method of standby acetylene, master equation are as follows:
The reaction not only needs the higher methane of purity as raw material (90% or more), but also methane is converted into the production of acetylene
Rate only has 40%~50%, and the cracking gas of generation is the gaseous mixture comprising a large amount of methane and acetylene.So separating second from methane
Alkynes is a kind of important industrial process stream, can not only improve the purity of natural gas, moreover it is possible to provide the second of purifying for Chemical Manufacture
Alkynes raw material.
Traditional separating technology is cracking gas cold separation technology, utilizes the difference of hydrocarbon relative volatilities all kinds of in cracking gas
It is different, hydro carbons in addition to the hydrogen is all condensed at low temperature, rectifying column is transferred to later and carries out multicomponent rectification separation, not only energy consumption
It is larger, and equipment manufacturing cost is higher [CN205774195U, CN205700034U, CN1292486A, CN104534812A].In addition
Industrially also common solvent absorption method separates acetylene, such as United States Patent (USP) US1960326 is made with benzene derivative and sulfuric acid
Adsorbing separation is carried out to acetylene for lyosoption；United States Patent (USP) US3647843, which is then used, contains coordination metal compound CuAlCl4
Toluene solution and acetylene occur complex reaction, to be separated to acetylene methane mixed gas.But such methods are used largely
Organic solvent, higher cost have pollution to environment.
In order to improve separative efficiency, reduce separation costs, exploitation new selective adsorbent material is unusual meaning.Metal
Organic framework material (Metal-Organic Frameworks, MOF) has large specific surface area, pore structure adjustable and duct table
Face is easy to the advantages that modifying, and can be widely used in gas absorption separation field.Capture due to MOFs material to multiple gases
There is good effect, the functionality of adjustment hole carrys out selective absorption class gas to carry out the focus for being separated into research.
Chinese patent CN10505524083A discloses a kind of preparation method of zinc metal-organic framework materials for purified natural gas,
This method is reacted in N, N '-dimethyl formamide solvent with zinc nitrate and bis- (3,5- dicarboxyphenyi) phosphinic acids organic ligands
A kind of metal organic framework compound is made, then immersion, vacuum drying obtain a kind of adsorbent material, for the pure of natural gas
Change.The preparation method uses organic solvent N, N '-dimethyl formamide, non-green environmental protection, and lacks in obtained porous material
It is used for the functional group (such as amino, pyridyl group) of Selective Separation less.
Summary of the invention
The technical problem to be solved by the present invention is to make up the deficiency of appeal original technology, propose a kind of for acetylene and first
The metal-organic framework materials and preparation method thereof of alkane adsorbing separation.
Technical problem of the invention is resolved by technical solution below:
A kind of micropore metal organic framework material, molecular formula are Y (C30N10O12H15), structural formula is as follows:
The micropore metal organic framework compounds category hexagonal crystal system, P31c space group.
The present invention provides a kind of preparation methods of micropore metal organic framework material: by yttrium nitrate and organic ligand 2,5,
8- tri- (3,5- dicarboxyanyline)-ipazine (C30N10O10H18, H6TDPAH) soluble in water, in 140~180 DEG C react 24~
Obtain within 48 hours micropore metal organic framework material crude product；It is thick that the micropore metal organic framework material is washed with anhydrous propanone
The micropore metal organic framework material that product is purified dries in 80 DEG C~100 DEG C, obtains colourless bulk crystals；It is organic to match
Body H6TDPAH, yttrium nitrate, water molar ratio be 1:3~5:800~1200.
The utility model has the advantages that
1. a kind of micropore metal organic framework material prepared by the present invention separated for acetylene and methane adsorption is based on Y
(III) metal ion and organic ligand 2,5,8- tri- (3,5- dicarboxyanyline)-ipazine (C30N10O10H18, H6TDPAH) water
The metal-organic framework materials synthesized under heat condition, due in organic ligand include equal ipazine and imino functionalities,
The feature that the material had both kept metallo organic material large specific surface area, physical absorption ability strong, further through equal ipazine and imido
Base functional group collective effect improves duct and acetylene interacts.
2. a kind of micropore metal organic framework material pretreatment prepared by the present invention separated for acetylene and methane adsorption
Program is simple to operation.
3. a kind of micropore metal organic framework material prepared by the present invention separated for acetylene and methane adsorption can be real
Efficient selective absorption under existing normal pressure.
4. a kind of micropore metal organic backbone prepared by the present invention separated for acetylene and methane adsorption is in small point of absorption
After sub- gas, the gas molecule of absorption can be removed by way of simply reheating, be conducive to Reusability.
5. reaction makees solvent with water, environmental-friendly.
Detailed description of the invention
Fig. 1 micropore metal organic framework material crystal prototype figure of the present invention；
Fig. 2 micropore metal organic framework material structural schematic diagram of the present invention；
The XRD spectrum of the micropore metal organic framework material prepared in Fig. 3 embodiment of the present invention 1；
The infared spectrum of the micropore metal organic framework material prepared in Fig. 4 embodiment of the present invention 1；
Micropore metal organic framework material prepared by the embodiment of the present invention 1 under the conditions of Fig. 5 77K, 0~101324Pa
Nitrogen adsorption isotherm；
Fig. 6 micropore metal organic framework material prepared by the embodiment of the present invention 1 under the conditions of 298K, 0~101324Pa
Acetylene and methane adsorption isotherm.
Specific embodiment
Below in conjunction with attached drawing, present invention is further described in detail with embodiment, it should be pointed out that its purpose only exists
In the protection scope for being best understood from the contents of the present invention and being not intended to limit the present invention.
Embodiment 1:
The synthesis actual conditions for the novel microporous metal-organic framework materials prepared below to the present invention are done further in detail
It describes in detail bright.In the present embodiment, the synthesis condition that metal organic framework poromerics uses is as follows:
Reaction is C with organic ligand30N10O10H18(0.07g)；
Metal yttrium salt is six nitric hydrate yttrium Y (NO)3·6H2O(0.15g)；
Reaction dissolvent is water (7ml).
Specific synthesis step is as follows:
Sequence weighs 0.07g organic ligand C30N10O10H18With six nitric hydrate yttrium of 0.15g into 10ml reaction kettle, then plus
Enter 1.8ml water, stir evenly, be put into after being reacted 24 hours in 160 DEG C of baking ovens with 3 DEG C/h be down to room temperature be obtained by filtration it is colourless
Bulk crystals, yield are 90% (with organic ligand H6TDPAH is calculated).Cell parameter is 15.0326,15.0326,13.4206,
90,90,120.
Embodiment 2:
The solution of embodiment 1 is moved in glass tube, glass tube is vacuumized, is then sintered and is sealed with alcohol blast burner,
His condition is constant, obtains and identical material described in embodiment 1.
Embodiment 3
Sequence weighs 0.07g organic ligand C30N10O10H18With six nitric hydrate yttrium of 0.12g into 10ml reaction kettle, then plus
Enter 1.4ml water, stir evenly, is put into and is down to room temperature after reacting 24 hours in 180 DEG C of baking ovens with 3 DEG C/h implementation is obtained by filtration
Metal-organic framework materials described in example 1, yield are 80% (with organic ligand H6TDPAH is calculated).
Embodiment 4
Sequence weighs 0.07g organic ligand C30N10O10H18With six nitric hydrate yttrium of 0.19g into 15ml reaction kettle, then plus
Enter 2.2ml water, stir evenly, is put into and is down to room temperature after reacting 48 hours in 140 DEG C of baking ovens with 3 DEG C/h implementation is obtained by filtration
Metal-organic framework materials described in example 1, yield are 65% (with organic ligand H6TDPAH is calculated).
In conclusion the present invention utilizes simple and environmentally-friendly method, one kind has been synthesized centered on Y (III), has contained equal ipazine
With the micropore metal organic framework material of imino group functional group, which has biggish specific surface area (798m2g-1), duct
Diameter isThere is good acetylene and methane adsorption separating capacity under normal temperature and pressure, C can be captured in the industrial production2H2Make
For important industrial chemicals.
The above content is a further detailed description of the present invention in conjunction with specific preferred embodiments, and it cannot be said that
Specific implementation of the invention is only limited to these instructions.It for those of ordinary skill in the art, can be according to the present invention
Technical solution and inventive concept, make it is corresponding change and substitution, and performance or use is identical, all should be considered as of the invention
Protection scope.
Claims (2)
1. a kind of micropore metal organic framework material separated for acetylene and methane adsorption, molecular formula Y
(C30N10O12H15), structural formula is as follows:
The micropore metal organic framework material category hexagonal crystal system, P31c space group.
2. a kind of system of micropore metal organic framework material separated for acetylene and methane adsorption according to claim 1
Preparation Method, which is characterized in that by yttrium nitrate and organic ligand 2,5,8- tri- (3,5- dicarboxyanyline)-equal ipazine
(C30N10O10H18, H6TDPAH) soluble in water, it is reacted 24~48 hours in 140~180 DEG C and obtains micropore metal organic backbone material
Expect crude product；The organic bone of micropore metal that the micropore metal organic framework material crude product is purified is washed with anhydrous propanone
Frame material dries in 100 DEG C, obtains colourless bulk crystals；Organic ligand H6TDPAH, yttrium nitrate, water molar ratio be 1:3~
5:800~1200.
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