CN109261214A - A kind of photochemical catalyzing prepares the preparation method of hydrogen catalyst - Google Patents
A kind of photochemical catalyzing prepares the preparation method of hydrogen catalyst Download PDFInfo
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- CN109261214A CN109261214A CN201811199868.3A CN201811199868A CN109261214A CN 109261214 A CN109261214 A CN 109261214A CN 201811199868 A CN201811199868 A CN 201811199868A CN 109261214 A CN109261214 A CN 109261214A
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- compound
- preparation
- graphene oxide
- modification
- amine
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- 239000001257 hydrogen Substances 0.000 title claims abstract description 38
- 229910052739 hydrogen Inorganic materials 0.000 title claims abstract description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 239000003054 catalyst Substances 0.000 title claims abstract description 21
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 68
- 229910021389 graphene Inorganic materials 0.000 claims abstract description 56
- 230000004048 modification Effects 0.000 claims abstract description 32
- 238000012986 modification Methods 0.000 claims abstract description 32
- -1 amine compound Chemical class 0.000 claims abstract description 25
- 150000003851 azoles Chemical class 0.000 claims abstract description 8
- 238000005406 washing Methods 0.000 claims abstract description 6
- 238000005119 centrifugation Methods 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000001291 vacuum drying Methods 0.000 claims abstract description 5
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 4
- 239000002105 nanoparticle Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical group 0.000 claims description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
- 229910002804 graphite Inorganic materials 0.000 claims description 13
- 239000010439 graphite Substances 0.000 claims description 13
- 239000000243 solution Substances 0.000 claims description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical class C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 235000019441 ethanol Nutrition 0.000 claims description 9
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 6
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 6
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 239000003929 acidic solution Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 3
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 3
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 claims description 3
- 229920002873 Polyethylenimine Polymers 0.000 claims description 3
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 claims description 3
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 229940045713 antineoplastic alkylating drug ethylene imines Drugs 0.000 claims description 3
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 3
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 3
- 150000002475 indoles Chemical class 0.000 claims description 3
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000005002 naphthylamines Chemical class 0.000 claims description 3
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 3
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 239000012286 potassium permanganate Substances 0.000 claims description 3
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 3
- 229940080818 propionamide Drugs 0.000 claims description 3
- 150000003233 pyrroles Chemical class 0.000 claims description 3
- XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 claims description 2
- GWIAAIUASRVOIA-UHFFFAOYSA-N 2-aminonaphthalene-1-sulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(N)=CC=C21 GWIAAIUASRVOIA-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 230000008859 change Effects 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 229960004125 ketoconazole Drugs 0.000 claims description 2
- 238000009210 therapy by ultrasound Methods 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 239000004575 stone Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 13
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 22
- 239000007789 gas Substances 0.000 description 19
- 238000010926 purge Methods 0.000 description 15
- 230000007246 mechanism Effects 0.000 description 11
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 230000001699 photocatalysis Effects 0.000 description 8
- 230000003197 catalytic effect Effects 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 229960004756 ethanol Drugs 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000002604 ultrasonography Methods 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound 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 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000007146 photocatalysis Methods 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- MLPVBIWIRCKMJV-UHFFFAOYSA-N 2-ethylaniline Chemical compound CCC1=CC=CC=C1N MLPVBIWIRCKMJV-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229960000935 dehydrated alcohol Drugs 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229940018564 m-phenylenediamine Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- GPRYKVSEZCQIHD-UHFFFAOYSA-N 1-(4-aminophenyl)ethanone Chemical compound CC(=O)C1=CC=C(N)C=C1 GPRYKVSEZCQIHD-UHFFFAOYSA-N 0.000 description 1
- FOYHNROGBXVLLX-UHFFFAOYSA-N 2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1N FOYHNROGBXVLLX-UHFFFAOYSA-N 0.000 description 1
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 101000878457 Macrocallista nimbosa FMRFamide Proteins 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical group N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229940031098 ethanolamine Drugs 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002594 fluoroscopy Methods 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- VSHTWPWTCXQLQN-UHFFFAOYSA-N n-butylaniline Chemical compound CCCCNC1=CC=CC=C1 VSHTWPWTCXQLQN-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004355 nitrogen functional group Chemical group 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002525 ultrasonication Methods 0.000 description 1
Classifications
-
- 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
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/26—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24
- B01J31/28—Catalysts comprising hydrides, coordination complexes or organic compounds containing in addition, inorganic metal compounds not provided for in groups B01J31/02 - B01J31/24 of the platinum group metals, iron group metals or copper
-
- 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
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/30—Catalysts, in general, characterised by their form or physical properties characterised by their physical properties
- B01J35/39—Photocatalytic properties
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B3/00—Hydrogen; Gaseous mixtures containing hydrogen; Separation of hydrogen from mixtures containing it; Purification of hydrogen
- C01B3/02—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen
- C01B3/04—Production of hydrogen or of gaseous mixtures containing a substantial proportion of hydrogen by decomposition of inorganic compounds, e.g. ammonia
- C01B3/042—Decomposition of water
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
- C01B32/182—Graphene
- C01B32/184—Preparation
-
- 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
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/36—Hydrogen production from non-carbon containing sources, e.g. by water electrolysis
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nanotechnology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Combustion & Propulsion (AREA)
- Catalysts (AREA)
Abstract
The invention discloses the preparation methods that a kind of photochemical catalyzing prepares hydrogen catalyst, the modification of preparation and graphene oxide including graphene oxide, wherein the graphene oxide is first handled in the ultrasonic wave of organic alcoholic solution, afterwards by organic amine compound or azoles modification, graphene oxide after the modification is through organic solvent washing, centrifugation and vacuum drying, last graphene oxide original position Supported Pt Nanoparticles after the modification.The method for preparing catalyst that the photochemical catalyzing that the present invention invents prepares hydrogen has the characteristics that preparation flow is simple, production cost is low.
Description
Technical field
The present invention relates to catalysis material fields, and the preparation of hydrogen catalyst is prepared more particularly to a kind of photochemical catalyzing
Method.
Background technique
In face of the worldwide energy and environmental problem in face of growing tension, solar energy photocatalytic hydrogen manufacturing being probed into and developing
Become worldwide important topic again.Under suitable catalyst action, water is decomposed using sunlight catalytic and prepares hydrogen, at
For one of the method for fundamentally solving the energy and environmental protection problem in the world today.According to system difference, light can be realized
There are mainly two types of the approach of hydrogen production by water decomposition: first is that electrode photoelectric chemical breakdown water hydrogen manufacturing；Another kind is suspension system photocatalysis
Decompose water oxygen.Compared with the former, the latter has the advantages such as react relatively easy, solid-liquid contact area obviously expands.Therefore, exist
When researching and developing to photocatalysis hydrogen production technology, choosing to suitable photochemical catalyst becomes very crucial problem；It looks for simultaneously
The preparation method that the photochemical catalyzing simple to a kind of process, production cost is low prepares hydrogen catalyst is similarly important.
Summary of the invention
The purpose of the present invention is to provide the preparation method that a kind of photochemical catalyzing prepares hydrogen catalyst, the preparation sides
Method has the characteristics that preparation flow is simple, production cost is low, while gained catalyst has urging for good photochemical catalyzing
Change activity, and hydrogen production efficiency is high, catalytic component is simple.
The technical solution adopted by the present invention is that: a kind of photochemical catalyzing prepares the preparation method of hydrogen catalyst, at least
Following steps: the preparation of graphene oxide and the modification of graphene oxide, wherein the preparation of the graphene oxide includes
Graphite reacts in strongly acidic solution with potassium permanganate strong oxidizer, carry out after having reacted it is cooling, distill water washing, centrifugation and
It is dry；
The modification of the graphene oxide are as follows: graphene oxide first is handled in the ultrasonic wave of organic alcoholic solution, after by
A kind of organic amine compound or azoles modification, the graphene oxide after modification are washed through organic solvent
It washs, be centrifuged and be dried in vacuo, finally the Supported Pt Nanoparticles on the graphene oxide of modification.
Organic amine compound of the present invention refers to aromatic amine compounds, fat amine compound, alcamines
Close object, amides compound, alicyclic ring aminated compounds, naphthalene system aminated compounds and polyethyleneimine, azanol, in hydrazine compound
Any one compound.
Preferably, the fat amine compound be selected from methylamine, ethamine, ethylenediamine, propylamine, cyclopropylamine, n-butylamine, oneself
Diamines, trioctylamine, decyl amine, any one compound in octadecylamine；
Or the alcamine compound is selected from ethyl alcohol, Propanolamine, N, N- dimethylethanolamine, N are appointed in N- diethyl ethylene diamine
It anticipates a kind of compound；
Or the amides compound be selected from formamide, acetamide, propionamide, butyramide, polyacrylamide, caprolactam,
Any one compound in dimethylformamide；
Or the alicyclic ring aminated compounds be selected from triethylenediamine, hexa, cyclic ethylene imines, morpholine, piperazine,
Any one compound in cyclohexylamine；
Or the naphthalene system aminated compounds is selected from naphthylamines, 1-Naphthylamine-5-sulfonic, Kerafyrm acid, tobias acid, phthalimide, ox sulphur
Any one compound in acid.
Azoles of the present invention in pyrroles, indoles, heteroauxin, tryptophan, ketoconazole any one
Compound.
Strong acid of the present invention is preferably any one of phosphoric acid or sulfuric acid.
Graphite of the present invention is preferably 40 DEG C of ∽ with the reaction temperature of potassium permanganate strong oxidizer in strongly acidic solution
60℃。
Graphene oxide of the present invention is first handled in the ultrasonic wave of organic alcoholic solution, and the Organic Alcohol is methanol
Or ethyl alcohol, processing time are 0.5 ∽ 2 hours.
The temperature of modification of the present invention is 60 ~ 150 DEG C, and the time is 10 ~ 30 hours.
Graphene oxide after modification of the present invention is organic solvent washing and vacuum drying.
Graphene receives the concern and research of common people as a kind of current novel electronic material.One layer of graphitic molecules
One layer of arrangement, this leads to its interlayer physical active force very little, and also exactly it makes it in these excellent properties of configuration aspects
There are important value and application in field of compound material.Graphite oxide is prepared into using graphite powder as raw material through aoxidizing.And oxygen
Graphite alkene passes through under the physical means such as ultrasound, stirring in the solution usually using graphite oxide as presoma, and remove
Individual layer laminated structure substance, graphene oxide have good dispersibility.
Graphene oxide is as being oxidation product by graphene, and oxygen-containing functional group thereon significantly increases, this makes it
Property in terms of itself physics and chemistry is more active compared with graphene；Correspondingly, many substances are chemically reacted with oxygen-containing functional group, just
The property of itself can be improved.
The present invention utilizes the oxygen-containing functional group on graphene oxide and containing on machine aminated compounds or azoles
Certain chemical action occurs for nitrogen functional group, forms new compound, and noval chemical compound is provided with good photochemical catalyzing
Catalytic activity, and the feature that hydrogen production efficiency is high, catalytic component is simple.
The method of the present invention has the characteristics that preparation flow is simple, production cost is low, while gained catalyst is with good
The catalytic activity of photochemical catalyzing, and hydrogen production efficiency is high, catalytic component is simple.
Detailed description of the invention
Fig. 1 is graphene oxide infared spectrum prepared by embodiment 1；
Fig. 2 is graphene oxide X-ray diffraction scanning figure prepared by embodiment 1；
Fig. 3 is the graphene oxide infared spectrum modified through p-phenylenediamine prepared by embodiment 1；
Fig. 4 is the device structure schematic diagram that a kind of photochemical catalyzing prepares hydrogen；
In figure, 1, purge gas mechanism；2, gas vent control valve；3, high-pressure mercury light source；4, purge gas is vented valve；5, it blows
Scavenging body is vented mechanism；6, control valve；7, hydrogen testing agency；8, photochemical catalyst and reacting solution；9, reactor；10, surpass
Sound instrument；11, rabbling mechanism.
Specific embodiment
Below by example, present invention be described in more detail, but the present invention is not limited thereto.
Embodiment 1
(1) preparation of graphene oxide
The 360mL concentrated sulfuric acid and 40mL concentrated phosphoric acid are successively measured, and is successively transferred in the three-neck flask equipped with magnetite, magnetic force is placed in
It is mixed on blender；3.0g graphite powder is weighed again to put into above-mentioned three-necked flask, and three-necked flask is placed in ice bath cryogenic conditions
Under, then 18g KMnO is added in batches4, KMnO to be finished4Afterwards, the reactant in there-necked flask is made to be warming up to 50 DEG C, and in this condition
Under, it flows back 20 hours.
After reaction sufficiently, crude product is obtained, room temperature is naturally cooled to.To shift to an earlier date again ready 400mL deionized water with
10mL30% H2O2The mixing ice cube of composition is poured into the reaction solution for having been transferred to large beaker, and is stirred, and whipping process exists
It is carried out in ice bank, to absorb diluting concentrated sulfuric acid amplification calorimetric.
Then, above-mentioned product (successively operated wash and centrifugation three to four times) is purified with deionized water, it is molten to make that treated
Liquid pH value can't detect SO near neutral value4 2-；Every time before centrifugation, being placed on magnetic stirring apparatus to centrifugate, stir
Mix a quarter of an hour.
Product after purification is placed in 10 hours of processing in 60 DEG C of vacuum drying oven.It is then ground to powder, after being used for
Continuous experiment.
Fig. 1 is the infrared spectrum of the graphene oxide of above method preparation, it can be seen that infrared spectroscopy 3402cm-1Place
It is-OH stretching vibration peak, 1732cm-1Place is C=O flexural vibrations peak, 1228cm-1Place is that C-O-C stretching vibration peak is (most strong to absorb
Peak) and 1049cm-1Place is C-O stretching vibration peak.Above-mentioned data are demonstrated with the presence of oxygen-containing functional group in the structure of matter, that is,
It says that graphite completes the process being oxidized, generates novel substance.Wherein the not strong cause in the peak C=O is that it is only at graphite linings edge
It can be formed；And epoxy group peak is not weak, illustrates that the quantity of epoxy group and hydroxyl is not within minority.
Fig. 2 is the graphene oxide X-ray diffraction scanning figure of above method preparation, it can be seen that x-ray diffraction pattern
Scanning range is 100To 900, in 2 θ=11. 920, there is the characteristic diffraction peak of graphene oxide, and peak strength is big, i.e., in place
Preparation relatively succeeds；2 θ are 20 to 300In section, there are graphite features diffraction maximum, show that its graphite oxidation is not enough.
(2) modification of the p-phenylenediamine to graphene oxide
0.500g graphene oxide powder is weighed with electronic balance, is dissolved in the beaker equipped with 100mL dehydrated alcohol, it is close
Seal, and place it in Ultrasound Instrument handle 1 hour it is spare；
Then, 4.000g paraphenylenediamine is accurately weighed with balance, is dissolved in the three-necked flask equipped with 200mL same solvent
In, paraphenylenediamine is easily oxidized rotten in the presence of light, therefore when taking p-phenylenediamine, should be protected from light, keep away oxygen, operation is wanted
Rapidly.In logical protectiveness nitrogen, and under the premise of covering in reaction unit with the plastic bag of black, then by graphene oxide
Ethanol solution is poured into paraphenylenediamine's solution, is reacted, is heated at reflux 24 hours at 80 DEG C.
To after the reaction was completed, with ethanol washing and be centrifuged above-mentioned crude product three to four times, then washed with tetrahydrofuran and from
Heart product.The product of purification is finally placed in a vacuum drying oven room temperature to handle 2 hours.
Fig. 3 is the infrared spectrum of the graphene oxide after p-phenylenediamine is modified of above method preparation, it can be seen that
1398cm-1Place is C-N stretching vibration peak, 1576cm-1Place is-NH2Flexural vibrations peak, they are the characteristic peaks of amine.1005cm-1
Place is C-O stretching vibration peak (most at strong absworption peak), 1099cm-1Place is C-O-C stretching vibration peak, 2359cm-1Place is nitrogen nitrogen three
The stretching vibration peak of key.Illustrate that p-phenylenediamine is reacted with graphene oxide, p-phenylenediamine carries out graphene oxide
Modification.
(3) foundation of photocatalytic hydrogen production by water decomposition device
The device of photocatalytic hydrogen production by water decomposition gas is established according to Fig. 4, the device that the photocatalysis Decomposition prepares hydrogen mainly wraps
Reactor (8), photochemical catalyst and reacting solution (9) and high-pressure sodium lamp light source (3) are included, wherein photochemical catalyst and reaction are water-soluble
Liquid (9) is placed in reactor (8), and high-pressure sodium lamp light source (3) is placed in reactor (8) outside, and the wall of reactor (8) can allow x ray fluoroscopy x
In to reactor (8).
In addition, being provided with rabbling mechanism (11) in reactor (8), the rabbling mechanism (11) is mainly used for being stirred to react
Photochemical catalyst and reacting solution (9) in device (8) improve the rate that photochemical catalyzing prepares hydrogen.And reactor (8) is outside
Bottom is also provided with Ultrasound Instrument (10), is mainly used for being dissolved to photochemical catalyst (9) is fully dispersed in reaction dissolvent before the reaction.
Reactor (8) top side is connected to purge gas mechanism (1), and the purge gas mechanism (1) provides purging
Gas source, the gas are nitrogen or rare gas, for the purging of reactor before reacting and as the carrier gas of reaction process,
Gas vent control valve (2) are provided in the purge gas mechanism (1), the throttling of gas is facilitated to control.
Reactor (8) top side has been also connected with purge gas emptying mechanism (5) and hydrogen testing agency (7), purge gass
Body is vented the purging that mechanism (5) are used for reactor, and purge gas emptying valve is also provided in purge gas emptying mechanism (5)
(4), after reactor purging, purge gas emptying valve (4) is closed, air-flow can enter hydrogen testing agency (7).
Hydrogen testing agency (7) is used to detect the hydrogen that reaction generates, and hydrogen testing agency (7) arrival end is provided with control valve (6), uses
Enter in hydrogen testing agency in control air-flow, hydrogen testing agency (7) is preferably gas chromatograph.
(4) photocatalytic hydrogen production by water decomposition
After establishing the device of photocatalytic hydrogen production by water decomposition gas according to above (3), 0.1000g is accurately weighed with assay balance
Graphene oxide in (2) after p-phenylenediamine is modified above, is put into three-necked flask.It is accurate to be distinguished again with pipette
Move into 0.67 mL chloroplatinic acid (concentration: 1.93 × 10-3Mol/L), 5 mL triethanolamines and isometric dehydrated alcohol are to flask
In, and the distilled water of appropriate volume is added, so that overall solution volume is maintained at 60 mL, and magnetite is added, wherein platinum and photochemical catalyst
Mass ratio is 0.25:100.Again by reaction system ultrasound 10min, and logical 25 min of high-purity nitrogen purges whole device, makes to fill
Middle oxygen is set to be discharged.
Reaction unit carries out in the environment of room temperature condition, adds magnetite.Before illumination, first switch power supply is pre- by high-pressure sodium lamp
Hot half an hour；After light intensity to be irradiated does not fluctuate, then reaction system is placed under lamp.Illumination reaction 3h rises, and carries out every hour
The hydrogen that sampling is prepared with gas chromatographic detection detects 5 times altogether.
Embodiment 2-16
The p-phenylenediamine of (2) in embodiment 1 is replaced with into aromatic amine compounds such as o-phenylenediamine, m-phenylene diamine (MPD), aniline, biphenyl
Amine, 23 dimethyl aniline, o ethyl aniline, N- butylaniline, 2,6- diethylaniline, formanilide, monoacetylaniline,
3- aminoanisole, parachloroanilinum, para-bromoaniline, the modification to fluorobenzene, paranitroanilinum to graphene oxide, other conditions with
Embodiment 1 is identical, respectively corresponds to obtain embodiment 2-16.
Embodiment 17-26
By the p-phenylenediamine of (2) in embodiment 1 replace with fat amine compound methylamine, ethamine, ethylenediamine, propylamine, cyclopropylamine,
The modification of n-butylamine, hexamethylene diamine, trioctylamine, decyl amine, octadecylamine to graphene oxide, other conditions are same as Example 1, respectively
Correspondence obtains embodiment 17-26.
Embodiment 27-30
The p-phenylenediamine of (2) in embodiment 1 is replaced with into alcamine compound such as ethanol amine, Propanolamine, N, N- dimethyl ethanol
Amine, N, modification of the N- diethyl ethylene diamine to graphene oxide, other conditions are same as Example 1, respectively correspond and implemented
Example 27-30.
Embodiment 31-37
By the p-phenylenediamine of (2) in embodiment 1 replace with amides compound for example formamide, acetamide, propionamide, butyramide,
The modification of polyacrylamide, caprolactam, dimethylformamide to graphene oxide, other conditions are same as Example 1, respectively
Correspondence obtains embodiment 31-37.
Embodiment 38-43
By the p-phenylenediamine of (2) in embodiment 1 replace with alicyclic ring aminated compounds for example triethylenediamine, hexa,
The modification of cyclic ethylene imines, morpholine, piperazine, cyclohexylamine to graphene oxide, other conditions are same as Example 1, respectively correspond
Obtain embodiment 38-43.
Embodiment 44-49
The p-phenylenediamine of (2) in embodiment 1 is replaced with into naphthalene system aminated compounds such as naphthylamines, 1-Naphthylamine-5-sulfonic, Kerafyrm acid, Tu Shi
The modification of acid, phthalimide, taurine to graphene oxide, other conditions are same as Example 1, respectively correspond to obtain
Embodiment 44-49.
Embodiment 50-52
The p-phenylenediamine of (2) in embodiment 1 is replaced into other organic amine compounds such as to polyethyleneimine, azanol, hydrazine to oxygen
The modification of graphite alkene, other conditions are same as Example 1, respectively correspond to obtain embodiment 50-52.
Embodiment 53-57
The p-phenylenediamine of (2) in embodiment 1 is replaced into azoles such as pyrroles, indoles, heteroauxin, tryptophan, ketone health
The modification of azoles, other conditions are same as Example 1, respectively correspond to obtain embodiment 53-57.
Embodiment 58-61
(4) chloroplatinic acid additional amount in embodiment 1 is replaced with into 0.27mL, 1.34mL, 2.68mL, 13.4mL by 0.67mL respectively,
Respectively obtaining platinum and photochemical catalyst mass ratio is 0.1:100,0.5:100,1:100,5:100, other conditions and 1 phase of embodiment
Together, it respectively corresponds to obtain embodiment 58-61.
Embodiment 62-63
By (1) KMnO in embodiment 14Graphite oxide powder reactant is warming up to 50 DEG C of reactant liters replaced in there-necked flask respectively
For temperature to 40 DEG C, 60 DEG C, other conditions are same as Example 1, respectively correspond to obtain embodiment 62-63.
Embodiment 64-65
P-phenylenediamine modification is replaced with respectively by 80 DEG C of reaction temperature of (2) p-phenylenediamine modification graphene oxide in embodiment 1
60 DEG C of the reaction temperature of graphene oxide, 95 DEG C, other conditions are same as Example 1, respectively correspond to obtain embodiment 64-65.
Embodiment 66-67
(2) p-phenylenediamine modification graphene oxide in embodiment 1 was replaced with p-phenylenediamine in the reaction time 20 hours respectively and repairs
The 10 hours reaction time, 30 hours of graphene oxide are adornd, other conditions are same as Example 1, respectively correspond to obtain embodiment
66-67。
Embodiment 68-70
By (2) graphene oxide in embodiment 1, ultrasonication replaces with graphene oxide ultrasonic wave in methyl alcohol in ethanol
Processing, other conditions are same as Example 1, respectively correspond to obtain embodiment 68.
(2) graphene oxide ultrasonic treatment time in embodiment 1 is replaced with 0.5 hour, 2 hours, other for 1 hour
Part is same as Example 1, respectively corresponds to obtain embodiment 69-70.
Comparative example
Graphene oxide in embodiment 1 is directly used in photochemical catalyzing and prepares hydrogen, graphene oxide does not do any modification,
Other conditions are same as Example 1, obtain comparative example.
The accumulative hydrogen output of embodiment 1-70 and comparative example in 5 hours is as shown in the following chart:
| Embodiment | Hydrogen output (μm ol) | Embodiment | Hydrogen output (μm ol) |
| 1 | 4.3 | 37 | 3.4 |
| 2 | 4.0 | 38 | 3.6 |
| 3 | 4.0 | 39 | 3.6 |
| 4 | 3.9 | 40 | 3.3 |
| 5 | 3.9 | 41 | 3.1 |
| 6 | 3.8 | 42 | 3.1 |
| 7 | 3.8 | 43 | 3.6 |
| 8 | 3.8 | 44 | 3.1 |
| 9 | 3.8 | 45 | 3.1 |
| 10 | 3.7 | 46 | 3.1 |
| 11 | 3.7 | 47 | 3.0 |
| 12 | 3.8 | 48 | 3.0 |
| 13 | 3.7 | 49 | 2.9 |
| 14 | 3.7 | 50 | 3.3 |
| 15 | 3.7 | 51 | 3.5 |
| 16 | 3.9 | 52 | 3.0 |
| 17 | 3.9 | 53 | 4.1 |
| 18 | 3.9 | 54 | 3.8 |
| 19 | 3.9 | 55 | 3.9 |
| 20 | 3.9 | 56 | 3.9 |
| 21 | 3.7 | 57 | 3.9 |
| 22 | 3.7 | 58 | 3.8 |
| 23 | 3.1 | 59 | 4.2 |
| 24 | 3.1 | 60 | 4.1 |
| 25 | 2.8 | 61 | 4.1 |
| 26 | 2.8 | 62 | 3.9 |
| 27 | 3.7 | 63 | 4.1 |
| 28 | 3.7 | 64 | 3.8 |
| 29 | 3.7 | 65 | 4.0 |
| 30 | 3.6 | 66 | 3.9 |
| 31 | 3.8 | 67 | 4.2 |
| 32 | 3.8 | 68 | 4.1 |
| 33 | 3.5 | 69 | 3.9 |
| 34 | 3.5 | 70 | 4.2 |
| 35 | 3.5 | ||
| 36 | 3.4 | Comparative example | 2.1 |
From above-described embodiment it can be seen that the preparation flow of the method for the present invention is simple, production cost is low, while gained catalyst has
There is the catalytic activity of good photochemical catalyzing, hydrogen production efficiency greatly improves.
Claims (9)
1. the preparation method that a kind of photochemical catalyzing prepares hydrogen catalyst, it is characterised in that at least following steps: oxidation stone
The preparation of black alkene and the modification of graphene oxide, wherein the preparation of the graphene oxide includes that graphite is molten in highly acid
It is reacted in liquid with potassium permanganate strong oxidizer, cooling is carried out after having reacted, distills water washing, centrifugation and drying；
The modification of the graphene oxide are as follows: graphene oxide first is handled in the ultrasonic wave of organic alcoholic solution, after by
A kind of organic amine compound or azoles modification, the graphene oxide after modification are washed through organic solvent
It washs, be centrifuged and be dried in vacuo, finally the Supported Pt Nanoparticles on the graphene oxide of modification.
2. preparation method according to claim 1, it is characterised in that the organic amine compound refers to aromatic amine
Compound, fat amine compound, alcamine compound, amides compound, alicyclic ring aminated compounds, naphthalene system amine chemical combination
Object and polyethyleneimine, azanol, any one compound in hydrazine compound.
3. preparation method according to claim 2, it is characterised in that: the fat amine compound is selected from methylamine, second
Amine, ethylenediamine, propylamine, cyclopropylamine, n-butylamine, hexamethylene diamine, trioctylamine, decyl amine, any one compound in octadecylamine；
Or the alcamine compound is selected from ethyl alcohol, Propanolamine, N, N- dimethylethanolamine, N are appointed in N- diethyl ethylene diamine
It anticipates a kind of compound；
Or the amides compound be selected from formamide, acetamide, propionamide, butyramide, polyacrylamide, caprolactam,
Any one compound in dimethylformamide；
Or the alicyclic ring aminated compounds be selected from triethylenediamine, hexa, cyclic ethylene imines, morpholine, piperazine,
Any one compound in cyclohexylamine；
Or the naphthalene system aminated compounds is selected from naphthylamines, 1-Naphthylamine-5-sulfonic, Kerafyrm acid, tobias acid, phthalimide, ox sulphur
Any one compound in acid.
4. preparation method according to claim 1, it is characterised in that: the azoles be selected from pyrroles, indoles,
Heteroauxin, tryptophan, any one compound in ketoconazole.
5. preparation method according to claim 1, it is characterised in that: the strongly acidic solution is phosphoric acid or sulfuric acid.
6. according to claim 1 to any one preparation method described in 4, it is characterised in that: the graphite is in strongly acidic solution
In with the reaction temperature of strong oxidizer be 60 DEG C of 40 ∽.
7. according to claim 1 to any one preparation method described in 4, it is characterised in that: the Organic Alcohol be methanol or
Ethyl alcohol, the graphene oxide ultrasonic treatment time are 0.5 ∽ 2 hours.
8. according to claim 1 to any one preparation method described in 4, it is characterised in that: the temperature of the modification is
60 95 DEG C of ∽, time are 10 ∽ 30 hours.
9. according to claim 1 to any one preparation method described in 4, it is characterised in that: the modification change after oxidation
Graphene organic solvent washing and vacuum drying.
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Application publication date: 20190125 |
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