CN101538275A - Calixarene compound porous water-absorbing material and preparation method thereof - Google Patents
Calixarene compound porous water-absorbing material and preparation method thereof Download PDFInfo
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- CN101538275A CN101538275A CN200910066678A CN200910066678A CN101538275A CN 101538275 A CN101538275 A CN 101538275A CN 200910066678 A CN200910066678 A CN 200910066678A CN 200910066678 A CN200910066678 A CN 200910066678A CN 101538275 A CN101538275 A CN 101538275A
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- calixarene
- calixarene compound
- compound porous
- salt
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- -1 Calixarene compound Chemical class 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000011358 absorbing material Substances 0.000 title claims description 25
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000463 material Substances 0.000 claims abstract description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 8
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims abstract description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 5
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical group [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 claims abstract description 5
- VTJUKNSKBAOEHE-UHFFFAOYSA-N calixarene Chemical compound COC(=O)COC1=C(CC=2C(=C(CC=3C(=C(C4)C=C(C=3)C(C)(C)C)OCC(=O)OC)C=C(C=2)C(C)(C)C)OCC(=O)OC)C=C(C(C)(C)C)C=C1CC1=C(OCC(=O)OC)C4=CC(C(C)(C)C)=C1 VTJUKNSKBAOEHE-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011148 porous material Substances 0.000 claims abstract description 5
- 239000011734 sodium Chemical group 0.000 claims abstract description 5
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 4
- 239000011591 potassium Chemical group 0.000 claims abstract description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims abstract description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 3
- 229910052792 caesium Inorganic materials 0.000 claims abstract description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims abstract description 3
- 150000002602 lanthanoids Chemical class 0.000 claims abstract description 3
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 3
- 229910052701 rubidium Inorganic materials 0.000 claims abstract description 3
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical group [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052706 scandium Inorganic materials 0.000 claims abstract description 3
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 3
- 229910052727 yttrium Inorganic materials 0.000 claims abstract description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 10
- 239000002994 raw material Substances 0.000 claims description 10
- 230000035484 reaction time Effects 0.000 claims description 10
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 229910003002 lithium salt Inorganic materials 0.000 claims description 2
- 159000000002 lithium salts Chemical class 0.000 claims description 2
- 150000001455 metallic ions Chemical class 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 150000003297 rubidium Chemical class 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 claims description 2
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical group C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims description 2
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 claims description 2
- PCMOZDDGXKIOLL-UHFFFAOYSA-K yttrium chloride Chemical compound [Cl-].[Cl-].[Cl-].[Y+3] PCMOZDDGXKIOLL-UHFFFAOYSA-K 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- 238000001179 sorption measurement Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 2
- GQPLZGRPYWLBPW-UHFFFAOYSA-N calix[4]arene Chemical compound C1C(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC(C=2)=CC=CC=2CC2=CC=CC1=C2 GQPLZGRPYWLBPW-UHFFFAOYSA-N 0.000 abstract 1
- 230000004087 circulation Effects 0.000 abstract 1
- 238000001027 hydrothermal synthesis Methods 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 230000003252 repetitive effect Effects 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 abstract 1
- 239000002178 crystalline material Substances 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 230000000274 adsorptive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Abstract
The invention discloses a calixarene compound porous material with water-absorbing performance and a preparation method thereof. The structural formula of the material is MxLn(PHEN)2(C4AS)-yH2O, wherein M is lithium, sodium, potassium, rubidium, cesium, ammonia or organic ammonium; Ln is yttrium, scandium or lanthanide; PHEN is o-phenanthroline; C4AS is calix[4]arene sulfonate; x is one of 0 to 1.0; and y is one of 1 to 15. The material is a three-dimensional network formed by the covalent bond coordination of calixarene and metal ion, and one-dimensional pore canals parallel in the network are mutually connected to form three-dimensional pore spaces. The material is prepared by adopting a hydrothermal method. The material selectively and reversibly absorbs water vapor or small molecular steam such as methanol, and adsorption capacity reaches 23% of self-weight; stable temperature can reach 390 DEG C, and the material is easily reproduced; and adsorption properties are not influenced by repetitive circulations.
Description
Technical field
What the present invention relates to is calixarene compound porous water-absorbing material.
Background technology
The property of water-absorbing material and application prospect are attracting the common concern of Chinese scholars, conduct a research one after another and the work of development of new water-absorbing material.J.L.Atwood, G.WilliamOrr, J.Barbourl etc. disclose Composition for operating a replenishablefuel cell comprises a stable guest-host assembly having a spheroidal hostassembly formed of trimers of calixarene molecules in a hexagonalclose-packed assembly by name patent (United States Patent (USP), US2003212301-A1).This compound is to form subunit by calixarene and object, and these subunits are piled up by model ylid bloom action power and formed one-dimensional channels, and class spheric structure is piled into by model ylid bloom action power again in these ducts.When temperature surpassed 150 ℃, compound structure was destroyed.At present, being prepared into and having three-dimensional nanometer material hole or that come in every shape, all is that intermolecular weak interaction force forms, so compound equilibrium temperature majority is in 200 ℃.
Summary of the invention
In order to solve the problem that prior art exists, the invention provides calixarene compound porous water-absorbing material and preparation method thereof.The chemical formula of this water-absorbing material is M
xLn (PHEN)
2(C
4AS) yH
2O, M is lithium, sodium, potassium, rubidium, caesium, ammonia or organic ammonium in the formula, and Ln is yttrium, scandium or lanthanon, and PHEN is a phenanthroline, and molecular formula is C
12H
8N
2, C
4AS is cup four aromatic hydrocarbons sulfonate radicals, and molecular formula is (C
28H
20O
16S
4)
4-, x is 0～1.0, y is 1～15.
Calixarene compound porous water-absorbing material preparation method's provided by the invention step and condition are as follows: reaction raw materials is cup four arene sulfonates, rare earth chloride and phenanthroline, their mol ratio is followed successively by 1.0～5.0: 1.0～5.0: 1.0～10.0, temperature of reaction is 120～160 ℃, reacting liquid pH value is 1～6, in 1～7 day reaction times, obtain calixarene compound porous water-absorbing material; Described cup four arene sulfonates comprise lithium salts, sodium salt, sylvite, rubidium salt, cesium salt, ammonia salt or organic ammonium salt; Described organic ammonium is tetramethyl-ammonium, tetraethyl ammonium, tetrapropyl ammonium or TBuA; Described rare earth chloride comprises Yttrium trichloride, Scium trichloride or group of the lanthanides muriate.
The characterization result of this calixarene compound porous water-absorbing material is as follows:
Molecular formula: C
208H
227.34N
16O
105.67S
16Eu
4Na
4, tetragonal system;
Spacer: P4
2/ mcm;
Unit cell parameters: a=18.9201
B=18.9201
C=21.2096
α＝90.000°，β＝90.000°，γ＝90.000°；
Molecular formula: C
208H
236N
16O
110S
16Ce
4Na
4, tetragonal system;
Spacer: P4
2/ mcm;
Unit cell parameters: a=19.3791
B=19.3791
C=20.6569
α＝90.000°，β＝90.000°，γ＝90.000°。
Beneficial effect: calixarene compound porous water-absorbing material provided by the invention is as part with calixarene, by the three-dimensional network that covalent linkage and metallic ion coordination form, one-dimensional channels parallel in the network also has been interconnected to form three-dimensional pore space by the form of covalent linkage.This all with covalent linkage form bonded three-dimensional nanometer material, stability is high, and equilibrium temperature can reach 390 ℃.
Calixarene compound porous water-absorbing material energy selectivity reversible adsorption steam provided by the invention or small molecules steam (as methyl alcohol), adsorptive capacity reaches 23% of deadweight, and equilibrium temperature reaches 390 ℃; Material is regenerated easily, and heat treated is promptly renewable under the vacuum, and does not influence absorption property after the regeneration, can be recycled more than 10 times.Repeatedly recycling does not influence absorption property.Can be used for the dehumidifying and the degassing in the particular surroundings, have good application prospects in a plurality of fields such as biology, medicine, environment.
Description of drawings
Fig. 1 is the crystalline structure figure of calixarene compound porous water-absorbing material skeleton.
Fig. 2 is crystalline material thermogravimetric analysis figure.
Fig. 3 is water vapor absorption and desorption graphic representation.
Embodiment
Embodiment 1: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four arene sulfonates, LaCl
37H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,120 ℃ of temperature of reaction, reacting liquid pH value is 4, in 4 days reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 2: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four arene sulfonates, PrCl
37H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,140 ℃ of temperature of reaction, reacting liquid pH value is 4, in 4 days reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 3: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four arene sulfonates, EuCl
36H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,160 ℃ of temperature of reaction, reacting liquid pH value is 4, in 4 days reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 4: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four aromatic hydrocarbons sulfonic acid rubidiums, GdCl
36H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,130 ℃ of temperature of reaction, reacting liquid pH value is 6, in 5 days reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 5: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four aromatic hydrocarbons sulfonic acid caesiums, TmCl
36H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0.130 ℃ of temperature of reaction, reacting liquid pH value are 1, in 1 day reaction times, obtain the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 6: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four aromatic hydrocarbons potassium sulfonates, TbCl
36H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,140 ℃ of temperature of reaction, reacting liquid pH value is 3, in 1 day reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 7: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four arene sulfonates, YCl
36H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,140 ℃ of temperature of reaction, reacting liquid pH value is 3, in 7 days reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Embodiment 8: calixarene compound porous water-absorbing material Hydrothermal Preparation provided by the invention, reaction raw materials are cup four arene sulfonates, ScCl
36H
2O and phenanthroline, its mol ratio was followed successively by 1.0: 1.0: 1.0,140 ℃ of temperature of reaction, reacting liquid pH value is 6, in 7 days reaction times, obtains the air-breathing suction crystalline material of three-dimensional hole.
Claims (2)
1, calixarene compound porous water-absorbing material is characterized in that, the chemical formula of this water-absorbing material is M
xLn (PHEN)
2(C
4AS) yH
2O, M is lithium, sodium, potassium, rubidium, caesium, ammonia or organic ammonium in the formula, and Ln is yttrium, scandium or lanthanon, and PHEN is a phenanthroline, and molecular formula is C
12H
8N
2, C
4AS is cup four aromatic hydrocarbons sulfonate radicals, and molecular formula is (C
28H
20O
16S
4)
4-, x is 0～1.0, y is 1～15; This material be with calixarene as part, by the three-dimensional network that covalent linkage and metallic ion coordination form, one-dimensional channels parallel in the network also has been interconnected to form three-dimensional pore space by the form of covalent linkage.
2, the preparation method of calixarene compound crystal water-absorbing material as claimed in claim 1, it is characterized in that step and condition are as follows: reaction raw materials is cup four arene sulfonates, rare earth chloride and phenanthroline, their mol ratio is followed successively by 1.0～5.0:1.0～5.0: 1.0～10.0, temperature of reaction is 120～160 ℃, reacting liquid pH value is 1～6, in 1～7 day reaction times, obtains calixarene compound porous water-absorbing material; Described cup four arene sulfonates comprise lithium salts, sodium salt, sylvite, rubidium salt, cesium salt, ammonia salt or organic ammonium salt; Described organic ammonium is tetramethyl-ammonium, tetraethyl ammonium, tetrapropyl ammonium or TBuA; Described rare earth chloride comprises Yttrium trichloride, Scium trichloride or group of the lanthanides muriate.
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|---|---|
| CN101538275A true CN101538275A (en) | 2009-09-23 |
| CN101538275B CN101538275B (en) | 2013-03-20 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104241676A (en) * | 2013-06-14 | 2014-12-24 | 中国科学院上海硅酸盐研究所 | Sodium battery containing pre wetting structure and preparation method thereof |
| US20160042825A1 (en) * | 2012-02-24 | 2016-02-11 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Solid-Liquid Process For Extraction Of Radionuclides From Waste Solutions |
| CN106673108A (en) * | 2016-12-26 | 2017-05-17 | 浙江大学 | Method for separating sodium from salt lake |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101003733A (en) * | 2006-01-20 | 2007-07-25 | 中国科学院福建物质结构研究所 | Fluorescence radiation material of rare earth metal |
| CN100575449C (en) * | 2008-01-11 | 2009-12-30 | 同济大学 | A kind of preparation method of rare earth aromatic carboxylic acids mesoporous red light material |
-
2009
- 2009-03-24 CN CN 200910066678 patent/CN101538275B/en not_active Expired - Fee Related
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160042825A1 (en) * | 2012-02-24 | 2016-02-11 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Solid-Liquid Process For Extraction Of Radionuclides From Waste Solutions |
| US9966157B2 (en) * | 2012-02-24 | 2018-05-08 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Solid-liquid process for extraction of radionuclides from waste solutions |
| CN104241676A (en) * | 2013-06-14 | 2014-12-24 | 中国科学院上海硅酸盐研究所 | Sodium battery containing pre wetting structure and preparation method thereof |
| CN104241676B (en) * | 2013-06-14 | 2016-03-23 | 中国科学院上海硅酸盐研究所 | Comprise sode cell of pre-wet structure and preparation method thereof |
| CN106673108A (en) * | 2016-12-26 | 2017-05-17 | 浙江大学 | Method for separating sodium from salt lake |
| CN106673108B (en) * | 2016-12-26 | 2019-10-29 | 浙江大学 | A method of separating sodium from salt lake |
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Effective date of registration: 20200904 Address after: Group 3, Tiantai village, Dongcheng Street, Jilin City, Jilin Province, 132000 Patentee after: Jilin Xinhua Industrial Co.,Ltd. Address before: 132000 Jilin Province Longtan District Tiedong District Longdong District 5 Units 91 Patentee before: Jilin Xinhua Investment Co.,Ltd. |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20130320 |