CN106629691B - A kind of preparation method of sulfonated redox graphene - Google Patents
A kind of preparation method of sulfonated redox graphene Download PDFInfo
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 73
- 229910021389 graphene Inorganic materials 0.000 title claims abstract description 69
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- 239000002994 raw material Substances 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 75
- 239000000243 solution Substances 0.000 claims description 38
- XYXNTHIYBIDHGM-UHFFFAOYSA-N ammonium thiosulfate Chemical compound [NH4+].[NH4+].[O-]S([O-])(=O)=S XYXNTHIYBIDHGM-UHFFFAOYSA-N 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 12
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 claims description 10
- 229950000244 sulfanilic acid Drugs 0.000 claims description 10
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 9
- 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 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 238000004140 cleaning Methods 0.000 claims description 7
- 239000008367 deionised water Substances 0.000 claims description 7
- 229910021641 deionized water Inorganic materials 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000908 ammonium hydroxide Substances 0.000 claims description 4
- 229910002804 graphite Inorganic materials 0.000 claims description 4
- 239000010439 graphite Substances 0.000 claims description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- -1 graphite Alkene Chemical class 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 238000000967 suction filtration Methods 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims 2
- ZAJAQTYSTDTMCU-UHFFFAOYSA-N 3-aminobenzenesulfonic acid Chemical compound NC1=CC=CC(S(O)(=O)=O)=C1 ZAJAQTYSTDTMCU-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 7
- 125000003700 epoxy group Chemical group 0.000 abstract description 4
- 238000007142 ring opening reaction Methods 0.000 abstract description 4
- 235000015424 sodium Nutrition 0.000 description 6
- 238000002604 ultrasonography Methods 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- RBTBFTRPCNLSDE-UHFFFAOYSA-N 3,7-bis(dimethylamino)phenothiazin-5-ium Chemical compound C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 RBTBFTRPCNLSDE-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 150000001989 diazonium salts Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229960000907 methylthioninium chloride Drugs 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910001416 lithium ion Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011232 storage material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000010148 water-pollination Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B2204/00—Structure or properties of graphene
- C01B2204/20—Graphene characterized by its properties
- C01B2204/22—Electronic properties
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/01—Particle morphology depicted by an image
- C01P2004/03—Particle morphology depicted by an image obtained by SEM
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Abstract
The invention discloses a kind of preparation method of sulfonated redox graphene, this method by epoxy group ring-opening reaction, introduces sulfonated group, sulfonated redox graphene is prepared using redox graphene as raw material.The present invention introduces sulfonated group by epoxy group ring-opening reaction, and reaction condition is mild, safe and stable, reliable, avoids diazo-reaction safety issue, has broad application prospects as moisture sensor material aspect.
Description
Technical field
The preparation method of the present invention relates to a kind of sulfonated redox graphene material with wet sensitive performance.
Background technique
Light, reliable and stable and inexpensive moisture sensor is in national defence, industry, agricultural, medicine, space flight, weather monitoring
Play very important effect.Humidity-sensitive material physical and chemical performance itself is the key factor for influencing its wet sensitive performance.Currently, preparing wet
The material of dependent sensor mainly has: organic polymer, ceramics, metal oxide and its compound etc..There is spirit in these materials
The parameters such as sensitivity, recovery time response time-, humidity hysteresis are not able to satisfy increasingly strict demand of the rapid technological growth to sensor.
Therefore, the superior performances humidity-sensitive materials such as high sensitivity, quick-speed response-recovery time, humidity hysteresis be short are researched and developed as the area research
Emphasis and hot spot.
Graphene is the two dimensional crystal for the only one layer of atomic thickness being made of carbon atom, is made of hexagonal lattice, this
The special structure of kind imparts the unique calorifics of grapheme material, mechanics and electric property.Currently, graphene is applied to
Lithium ion battery electrode material, supercapacitor, electrode of solar battery material, hydrogen storage material, sensor, optical material, medicine
Object carrier etc. illustrates the wide application prospect of grapheme material.How integrated use various graphene preparation methods
Advantage is learnt from other's strong points to offset one's weaknesses, and solves the problems, such as the insoluble and unstability of graphene, and perfect frame and electrical property etc. are to grind from now on
The hot and difficult issue studied carefully.Therefore, design prepares that high sensitivity, low humidity be stagnant, graphene-based material of quick response is that the field is ground
The key points and difficulties studied carefully.
In order to overcome the poor problem of graphene hydrophily, graphene and its derivative oxide are most potential wet sensitive materials
Material.Method with application prospect is exactly to adjust graphene thin layer hydrophilic-hydrophobic group, adjusts active point, graphene sulfonic acid
Change is exactly a kind of relatively effective method.Related sulfonated graphene is as humidity-sensitive material there is not yet document report.Sulfonic acid at present
Changing main method is to prepare graphene oxide with the Hummer method of modification, introduces sulphur on the surface of graphene by diazo-reaction
It is acidified group ,-COOH existing for surface and-SO3H group adsorbs the activity of methylene blue (MB), and height contains only epoxy better than surface
The graphene of base and hydroxyl.However, diazonium salt caused by diazo-reaction is higher to temperature control requirement, temperature it is slightly higher or
It under the action of light, i.e., easily decomposes, some even can also be decomposed in room temperature.In the dry state, some diazonium salts are unstable, living
Power is big, is heated or rubs, hits, can decomposition explosion.Therefore, sulfonated graphene is prepared using diazo-reaction there are a Dingan County
Full problem.
Summary of the invention
The purpose of the present invention is to solve defect existing in the prior art, it is mild, more to provide a kind of reaction condition
The preparation method of safety.
In order to achieve the above object, the present invention provides a kind of preparation method of sulfonated redox graphene, the party
Method, by epoxy group ring-opening reaction, introduces sulfonated group using redox graphene as raw material, and sulfonated go back is prepared
Former graphene oxide.
Specifically includes the following steps:
(1) redox graphene is taken, is dissolved in methanol, redox graphene methanol solution is prepared；It is described to go back
The concentration of former graphene oxide methanol solution is 3-5mg/mL；
(2) metallic sodium is added in Xiang Suoshu redox graphene methanol solution, is reacted 2-6 hours under stirring condition；Institute
The dosage for stating sodium is that 0.1-0.5g is added in every 20-50mL redox graphene methanol solution；
(3) after reaction, epoxychloropropane is added to be stirred to react 5-10 hours, 40-60 DEG C of backspin at 30-60 DEG C
Turn evaporation, obtains powder I；The dosage of the epoxychloropropane is the addition of every 20-50mL redox graphene methanol solution
0.1-0.5g；
(4) powder I is added in p-aminobenzene sulfonic acid anhydrous DMF solution, reacts 5- under 50-80 DEG C of stirring condition
15 hours；The dosage of the p-aminobenzene sulfonic acid is that 0.1-0.6g is added in every 20-50mL redox graphene methanol solution；Institute
The additional proportion for stating p-aminobenzene sulfonic acid and anhydrous DMF is 0.1-0.6g:20mL-50mL；
(5) reaction solution for obtaining step (4) filters, and taking precipitate cleaning, drying are to get the sulfonated reduction-oxidation
Graphene powder.
Wherein, the optium concentration of redox graphene methanol solution is 3.6mg/mL；Sodium and redox graphene
Addition molar ratio is 1:1-1.5, preferably 1:1；The addition molar ratio of epoxychloropropane and redox graphene is 1:1-
1.5, preferably 1:1；The molar ratio of p-aminobenzene sulfonic acid and redox graphene is 1:1-1.5, preferably 1:1.
Redox graphene is prepared using graphene oxide as raw material by ATS (Ammonium thiosulphate) reduction.Especially by
Following steps preparation: taking 0.1-1g graphene oxide, be dissolved in 100-200mL deionized water, 2-4 hours ultrasonic；It is molten with alkalinity
Liquid adjusts solution ph to 8-10, and 2-4 hours ultrasonic, then addition 1-5g reducing agent, reacts 5-15 hours at 60-90 DEG C；
To get the redox graphene after suction filtration, deionized water cleaning.
Wherein, alkaline solution is ammonium hydroxide or sodium hydroxide.Reducing agent is ATS (Ammonium thiosulphate) or hydrazine hydrate.
The present invention has the advantage that the present invention by epoxy group ring-opening reaction, introduces sulfonated compared with prior art
Group, reaction condition is mild, safe and stable, reliable, avoids diazo-reaction safety issue, as moisture sensor material
Material aspect has broad application prospects.
Detailed description of the invention
Fig. 1 is that the SEM of sulfonated redox graphene obtained by the embodiment of the present invention 2 characterizes photo.
Specific embodiment
The present invention is described in detail combined with specific embodiments below.
Embodiment 1
The sulfonated redox graphene of the present invention the preparation method is as follows:
(1) 0.1 g graphene oxide is weighed, is dissolved in 100 mL deionized waters, ultrasound 2 hours；
(2) 2 hours ultrasonic with sodium hydrate regulator solution pH value to 8, above-mentioned graphene oxide solution is moved into four necks and is burnt
In bottle；
(3) 1g hydrazine hydrate is weighed, is added in four-neck flask, is reacted 15 hours under the conditions of 60 DEG C；
(4) it filters, after deionized water cleaning, 20mL methanol is added, is prepared into redox graphene methanol solution.
(5) 0.1 g metallic sodium is weighed, is added in redox graphene methanol solution, is stirred to react 2 hours.
(6) epoxychloropropane 0.1g is weighed, in the solution after being added to step (5) reaction, is heated to 30 DEG C, stirring is anti-
It answers 10 hours, 30 DEG C of rotary evaporations obtain powder I.
(7) p-aminobenzene sulfonic acid 0.1g is weighed, is added in 20 mL anhydrous DMF solutions, is added the powder I of step 6,50
It is stirred to react under the conditions of DEG C 15 hours.
(8) it filters, clean, is dry.
Embodiment 2
The sulfonated redox graphene of the present invention the preparation method is as follows:
(1) 0.2 g graphene oxide is weighed, is dissolved in 200 mL deionized waters, ultrasound 2 hours；
(2) solution ph is adjusted to 10 with ammonium hydroxide, above-mentioned graphene oxide solution is moved to four-neck flask by ultrasound 2 hours
In；
(3) 2.5 g ATS (Ammonium thiosulphate) are weighed, are added in four-neck flask, are reacted 12 hours under the conditions of 80 DEG C；
(4) it filters, after deionized water cleaning, 50mL methanol is added, is prepared into redox graphene methanol solution.
(5) 0.1 g metallic sodium is weighed, is added in redox graphene methanol solution, is stirred to react 4 hours.
(6) 0.31 g of epoxychloropropane is weighed, in the solution after being added to step 5 reaction, is heated to 50 DEG C, stirring is anti-
It answers 6 hours, 50 DEG C of rotary evaporations obtain powder I.
(7) 0.57 g of p-aminobenzene sulfonic acid is weighed, is added in 50mL anhydrous DMF solution, the powder I of step 6 is added,
It is stirred to react under the conditions of 80 DEG C 12 hours.
(8) it filters, clean, is dry.
By the SEM of products therefrom characterization photo (such as Fig. 1) can be visual and clear find out sulfonated reduction-oxidation graphite
Alkene shows loose laminar structured, is conducive to next step material in the application of wet sensitive aspect of performance.
Embodiment 3
The sulfonated redox graphene of the present invention the preparation method is as follows:
(1) 1 g graphene oxide is weighed, is dissolved in 200 mL deionized waters, ultrasound 2 hours；
(2) solution ph is adjusted to 10 with ammonium hydroxide, above-mentioned graphene oxide solution is moved to four-neck flask by ultrasound 4 hours
In；
(3) 5g ATS (Ammonium thiosulphate) is weighed, is added in four-neck flask, is reacted 5 hours under the conditions of 90 DEG C；
(4) it filters, after deionized water cleaning, 50mL methanol is added, is prepared into redox graphene methanol solution.
(5) 5 g metallic sodiums are weighed, are added in redox graphene methanol solution, are stirred to react 6 hours.
(6) epoxychloropropane 0.5g is weighed, in the solution after being added to step (5) reaction, is heated to 60 DEG C, stirring is anti-
It answers 5 hours, 60 DEG C of rotary evaporations obtain powder I.
(7) p-aminobenzene sulfonic acid 0.6g is weighed, is added in 50 mL anhydrous DMF solutions, is added the powder I of step 6,80
It is stirred to react under the conditions of DEG C 5 hours.
(8) it filters, clean, is dry.
Claims (5)
1. a kind of preparation method of sulfonated redox graphene, it is characterised in that: the sulfonated redox graphene
Preparation method the following steps are included:
(1) redox graphene is taken, is dissolved in methanol, redox graphene methanol solution is prepared；The oxygen reduction
The concentration of graphite alkene methanol solution is 3-5mg/mL；
(2) metallic sodium is added in Xiang Suoshu redox graphene methanol solution, is reacted 2-6 hours under stirring condition；The sodium
Dosage be every 20-50mL redox graphene methanol solution be added 0.1-0.5g；
(3) after reaction, epoxychloropropane is added, at 30-60 DEG C, is stirred to react to rotate at 5-10 hours, 40-60 DEG C and steam
Hair, obtains powder I；The dosage of the epoxychloropropane is that 0.1- is added in every 20-50mL redox graphene methanol solution
0.5g；
(4) powder I is added in p-aminobenzene sulfonic acid anhydrous DMF solution, it is small that 5-15 is reacted under 50-80 DEG C of stirring condition
When；The dosage of the p-aminobenzene sulfonic acid is that 0.1-0.6g is added in every 20-50mL redox graphene methanol solution；It is described right
Aminobenzenesulfonic acid and the additional proportion of anhydrous DMF are 0.1-0.6g:20mL-50mL；
(5) reaction solution for obtaining step (4) filters, and taking precipitate cleaning, drying are to get the sulfonated reduction-oxidation graphite
Alkene powder.
2. preparation method according to claim 1, it is characterised in that: the concentration of the redox graphene methanol solution
For 3.6mg/mL；The molar ratio of the sodium and redox graphene is 1:1；The epoxychloropropane and redox graphene
Molar ratio be 1:1；The molar ratio of the p-aminobenzene sulfonic acid and redox graphene is 1:1.
3. preparation method according to claim 1 or 2, it is characterised in that: the redox graphene is with graphite oxide
Alkene is raw material, is prepared by ATS (Ammonium thiosulphate) or hydrazine hydrate reduction.
4. preparation method according to claim 3, it is characterised in that: the redox graphene passes through following steps system
It is standby: 0.1-1g graphene oxide is taken, is dissolved in 100-200mL deionized water, it is 2-4 hours ultrasonic；Solution is adjusted with alkaline solution
PH value is to 8-10, and 2-4 hours ultrasonic, then addition 1-5g ATS (Ammonium thiosulphate) or hydrazine hydrate, it is small to react 5-15 at 60-90 DEG C
When；To get the redox graphene after suction filtration, deionized water cleaning.
5. the preparation method according to claim 4, it is characterised in that: the alkaline solution is ammonium hydroxide or sodium hydroxide.
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