CN108816230A - A kind of novel Mg2FeAl-LDH catalyst and its application - Google Patents
A kind of novel Mg2FeAl-LDH catalyst and its application Download PDFInfo
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- 239000003054 catalyst Substances 0.000 title claims abstract description 45
- 238000006243 chemical reaction Methods 0.000 claims abstract description 37
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 238000003756 stirring Methods 0.000 claims abstract description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 12
- GRDXCFKBQWDAJH-UHFFFAOYSA-N 4-acetamidobenzenesulfonyl chloride Chemical compound CC(=O)NC1=CC=C(S(Cl)(=O)=O)C=C1 GRDXCFKBQWDAJH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 9
- 238000002425 crystallisation Methods 0.000 claims abstract description 8
- 230000008025 crystallization Effects 0.000 claims abstract description 8
- 238000001035 drying Methods 0.000 claims abstract description 7
- 239000003513 alkali Substances 0.000 claims abstract description 6
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(III) nitrate Inorganic materials [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 6
- 238000009938 salting Methods 0.000 claims abstract description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 4
- 238000005119 centrifugation Methods 0.000 claims abstract description 4
- 239000008367 deionised water Substances 0.000 claims abstract description 4
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 238000003786 synthesis reaction Methods 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 13
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 11
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002994 raw material Substances 0.000 claims description 5
- 206010013786 Dry skin Diseases 0.000 claims description 3
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- TURGSUHERZMDLT-UHFFFAOYSA-N 2-(3-aminopropylsulfanyl)ethanol Chemical compound NCCCSCCO TURGSUHERZMDLT-UHFFFAOYSA-N 0.000 claims 1
- 150000003457 sulfones Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- NOXAGGBPVGNKIW-UHFFFAOYSA-N 5-amino-1-(5-amino-2-hydroxypentyl)sulfanylpentan-2-ol Chemical compound NCCCC(CSCC(CCCN)O)O NOXAGGBPVGNKIW-UHFFFAOYSA-N 0.000 abstract description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 10
- 239000011777 magnesium Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 229910002651 NO3 Inorganic materials 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 230000033228 biological regulation Effects 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229960004756 ethanol Drugs 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- MBDUIEKYVPVZJH-UHFFFAOYSA-N 1-ethylsulfonylethane Chemical compound CCS(=O)(=O)CC MBDUIEKYVPVZJH-UHFFFAOYSA-N 0.000 description 1
- 241001062009 Indigofera Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000011938 amidation process Methods 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000011258 core-shell material Substances 0.000 description 1
- 229960000935 dehydrated alcohol Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- -1 magnesium iron ion Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000010792 warming 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/78—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with alkali- or alkaline earth metals
-
- 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
- B01J35/33—Electric or magnetic properties
-
- 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
- B01J35/396—Distribution of the active metal ingredient
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a kind of novel Mg2FeAl-LDH catalyst and its application, the Mg2FeAl-LDH method for preparing catalyst is as follows：By Mg（NO3）3·6H2O, Fe（NO3）3·9H20 and A1（NO3）3·9H20 addition deionized water is made into salting liquid, separately by NaOH and Na2CO3Ionized water is added and is made into mixed ammonium/alkali solutions；Above-mentioned aqueous slkali is poured into bottle, by salting liquid with 100mLh‑1Rate be added drop-wise in the aqueous slkali under being vigorously stirred, by above-mentioned reaction solution, crystallization 6h, crystallization terminate under 100 DEG C of stirring conditions, and reaction solution is put into drying box dry after repeatedly centrifugation water washing, obtain Mg2FeAl-LDH catalyst.The catalyst can be catalyzed the reaction of 4- acetamidobenzenesulfonyl chloride and 3- aminopropyl -2- hydroxyethyl thioether, product yield with higher with optimal conditions.
Description
Technical field
The present invention relates to a kind of synthesis of intermediate N [3- aminopropyl -2- hydroxyl ethyl sulfone] -4- nitrobenzene sulfonamide
Method belongs to chemical industry synthesis field.
Background technique
.N- [3- aminopropyl -2- hydroxyl ethyl sulfone] -4- nitrobenzene sulfonamide ()
As important dyestuff intermediate, the preparation field of reactive dye has extensive market application prospect, and synthetic reaction relies on
Catalyst improves reactivity, and the catalyst for seeking a kind of high catalytic activity is highly desirable.
Summary of the invention
The purpose of the present invention is to provide a kind of novel Mg2FeAl-LDH catalyst and its application, the catalyst to optimize
Under the conditions of can be catalyzed the reaction of 4- acetamidobenzenesulfonyl chloride and 3- aminopropyl -2- hydroxyethyl thioether, production with higher
Object yield.
A kind of novel Mg2FeAl-LDH catalyst, which is characterized in that the Mg2FeAl-LDH method for preparing catalyst is such as
Under：
Step 1, by Mg（NO3）3·6H2O, Fe（NO3）3·9H20 and A1（NO3）3·9H2It is molten that 0 addition deionized water is made into salt
Liquid, separately by NaOH and Na2CO3100mL ionized water is added and is made into mixed ammonium/alkali solutions；
Step 2 pours into above-mentioned aqueous slkali in four-hole bottle, by salting liquid with 100mLh-1Rate be added drop-wise to and be vigorously stirred down
Aqueous slkali in, after completion of dropwise addition solution adjust pH=10；
Step 3, by above-mentioned reaction solution, crystallization 6h, crystallization terminate under 100 DEG C of stirring conditions, and reaction solution is through repeatedly centrifugation water washing
Afterwards, 60 DEG C of dryings in drying box are put into and for 24 hours, obtain Mg2FeAl-LDH catalyst.
The catalyst is anti-for catalyzing and synthesizing N- [3- aminopropyl -2- hydroxyl ethyl sulfone] -4- nitrobenzene sulfonamide
It answers.
Described synthesis N- [3- aminopropyl -2- hydroxyl the ethyl sulfone] -4- nitrobenzene sulfonamide reaction response condition is as follows：
4- acetamidobenzenesulfonyl chloride, 3- aminopropyl -2- hydroxyethyl thioether, glacial acetic acid, hydrogen peroxide are primary raw material, used in
Raw material is according to the following ratio：4- acetamidobenzenesulfonyl chloride, 3- aminopropyl -2- hydroxyethyl thioether mass ratio are 6：7.
Beneficial effect：The present invention provides a kind of novel Mg2FeAl-LDH catalyst can be catalyzed 4- acetamidobenzenesulfonyl chloride
With the reaction of 3- aminopropyl -2- hydroxyethyl thioether, product yield with higher, LDH and control LDH thermally decomposes to yield mixed
It closes metal oxide and there is alkali center, thus can be used as solid base catalyst and reacted applied to amidation catalysis, will have change
The transition metal of valence characteristic quantitatively introduces LDH laminate, edits and laminate metallic element atom level after heat treatment with Gao Bibiao
High dispersive feature obtains the magnetic retention base catalysis of core-shell structure by assembling MgAI-LDH activity phase progressive functionalization
Agent has higher catalytic activity in the reaction, is recycled by externally-applied magnetic field to catalyst after reaction, can greatly improve catalysis
The agent rate of recovery, is applied to amidation process again, and product yield still keeps higher level.
Specific embodiment
Embodiment 1
A kind of synthetic method of intermediate N [3- aminopropyl -2- hydroxyl ethyl sulfone] -4- nitrobenzene sulfonamide, including following step
Suddenly：
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 23.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 28.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；
Step 2 uses glacial acetic acid regulation system pH=5 after reaction, and 0.2g wolframic acid is added, is slowly added dropwise under stirring at room temperature
The hydrogen peroxide of 12ml concentration 30%, 0.5h, which is added dropwise, is warming up to 85 DEG C；
Step 3 continues the hydrogen peroxide that 12ml concentration 30% is slowly added dropwise, and 1h is detected with starch KI test paper in indigo plant after being added dropwise
Color, 85 DEG C of insulated and stirreds react 3h, are cooled to room temperature after reaction, and -4 DEG C of refrigerated overnights have orange/yellow solid precipitation, filter,
Filter cake is recrystallized with dehydrated alcohol, obtains glassy yellow intermediate N [3- aminopropyl -2- hydroxyl ethyl sulfone] -4- nitrobenzene sulphonyl
Amine.
The Mg2FeAl-LDH method for preparing catalyst is as follows：
Step 1, by 5.1g Mg（NO3）3·6H2O, 3.2g Fe（NO3）3·9H20 and 1.1g A1（NO3）3·9H20 is added
100mL deionized water is made into salting liquid, separately by 1.6gNaOH and 2.0g Na2CO3100mL ionized water is added and is made into mixing alkali soluble
Liquid；
Step 2 pours into above-mentioned aqueous slkali in four-hole bottle, by salting liquid with 100mLh-1Rate be added drop-wise to and be vigorously stirred down
Aqueous slkali in, after completion of dropwise addition solution adjust pH=10；
Step 3, by above-mentioned reaction solution, crystallization 6h, crystallization terminate under 100 DEG C of stirring conditions, and reaction solution is through repeatedly centrifugation water washing
Afterwards, 60 DEG C of dryings in drying box are put into and for 24 hours, obtain Mg2FeAl-LDH catalyst.
Embodiment 2
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 20.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 28.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 3
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 17.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 28.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 4
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 14.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 28.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 5
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 11.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 28.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 6
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 23.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 24.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 7
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 23.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 20.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 8
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 23.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 16.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 9
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 23.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 12.3g 3- aminopropyl -2- hydroxyethyl thioether, and solution is kept
PH=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Embodiment 10
Step 1 is being packed into 2.0gMg2In the three-necked flask of FeAl-LDH catalyst under ice bath stirring, by 23.4g 4- acetyl ammonia
Base benzene sulfonyl chloride, which is dissolved in 80ml toluene, to be slowly added dropwise into 8.3g 3- aminopropyl -2- hydroxyethyl thioether, and pH value of solution is kept
=10,3h keep ice bath stirring reaction 1h after being added dropwise；Remaining step is the same as embodiment 1.
Reference examples 1
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, replace toluene, remaining step with the methylene chloride of equivalent
It is identical with embodiment 1.
Reference examples 2
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, replace toluene, remaining step and reality with the ethyl alcohol of equivalent
It is identical to apply example 1.
Reference examples 3
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, with 2.0g Fe3O4As catalyst, remaining step with
Embodiment 1 is identical.
Reference examples 4
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, catalyst is not added, remaining step and embodiment 1
It is identical.
Reference examples 5
It is with 1 difference of embodiment：In the synthesis step 2 of intermediate, regulation system pH=3, remaining step and embodiment 1 are complete
It is exactly the same.
Reference examples 6
It is with 1 difference of embodiment：In the synthesis step 2 of intermediate, regulation system pH=10, remaining step and embodiment 1 are complete
It is exactly the same.
Reference examples 7
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, Mg is not added（NO3）3·6H2O；Remaining step with
Embodiment 1 is identical.
Reference examples 8
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, Fe is not added（NO3）3·9H20；Remaining step with
Embodiment 1 is identical.
Reference examples 9
It is with 1 difference of embodiment：In the synthesis step 2 of catalyst, sodium hydroxide is not added, remaining step and embodiment
1 is identical.
Reference examples 10
It is with 1 difference of embodiment：In the synthesis step 2 of catalyst, sodium carbonate is not added, remaining step and embodiment 1
It is identical.
It is as shown in the table for reaction result under embodiment and reference examples different condition
| N- [3- aminopropyl -2- hydroxyl ethyl sulfone] -4- nitrobenzene sulfonamide yield/% | |
| Embodiment 1 | 99.8 |
| Embodiment 2 | 87.4 |
| Embodiment 3 | 74.4 |
| Embodiment 4 | 79.3 |
| Embodiment 5 | 81.7 |
| Embodiment 6 | 70.4 |
| Embodiment 7 | 84.0 |
| Embodiment 8 | 65.1 |
| Embodiment 9 | 61.5 |
| Embodiment 10 | 76.2 |
| Reference examples 1 | 50.1 |
| Reference examples 2 | 39.3 |
| Reference examples 3 | 37.0 |
| Reference examples 4 | 49.2 |
| Reference examples 5 | 44.5 |
| Reference examples 6 | 40.6 |
| Reference examples 7 | 45.4 |
| Reference examples 8 | 37.3 |
| Reference examples 9 | 41.0 |
| Reference examples 10 | 46.6 |
The experimental results showed that catalyst is anti-to the synthesis of 4- acetamidobenzenesulfonyl chloride and 3- aminopropyl -2- hydroxyethyl thioether
There should be good catalytic effect, in one timing of reaction condition, intermediate yield is higher, and catalytic performance is better, otherwise poorer；4-
Acetamidobenzenesulfonyl chloride, 3- aminopropyl -2- hydroxyethyl thioether mass ratio are 6：When 7, other ingredients are fixed, synthetic effect
Preferably, with embodiment 1 the difference lies in that embodiment 2 change respectively to embodiment 10 primary raw material 4- acetamidobenzenesulfonyl chloride,
The dosage and proportion of 3- aminopropyl -2- hydroxyethyl thioether, there is different influences to the yield of synthetic product；Reference examples 1 to
The methylene chloride and ethyl alcohol of the equivalent of reference examples 2 replace toluene respectively, other steps are identical, cause product yield obvious
It reduces, illustrates that toluene solvant is advantageous to the synthesis ratio of reaction；Reference examples 3 to reference examples 6 use Fe3O4Make catalyst and changes body
It is pH value, effect is still bad, illustrates importance of the control to reaction of catalyst and system PH；Reference examples 7 to reference examples 8 not
Magnesium nitrate and ferric nitrate are added, the effect for being catalyzed reaction is obviously deteriorated, and illustrates the catalyst after magnesium iron ion is compound to reaction
Good catalytic activity；Reference examples 9 to the single alkali of reference examples 10 replaces mixed ammonium/alkali solutions, and the reaction environment of catalyst becomes
Change, reaction effect is obviously deteriorated, and product yield is not still high；Therefore using catalyst of the invention to N- [3- aminopropyl -2-
Hydroxyl ethyl sulfone] -4- nitrobenzene sulfonamide synthetic reaction have excellent catalytic effect.
Claims (3)
1. a kind of novel Mg2FeAl-LDH catalyst, which is characterized in that the Mg2FeAl-LDH method for preparing catalyst is such as
Under：
Step 1, by Mg（NO3）3·6H2O, Fe（NO3）3·9H20 and A1（NO3）3·9H2It is molten that 0 addition deionized water is made into salt
Liquid, separately by NaOH and Na2CO3100mL ionized water is added and is made into mixed ammonium/alkali solutions；
Step 2 pours into above-mentioned aqueous slkali in four-hole bottle, by salting liquid with 100mLh-1Rate be added drop-wise to and be vigorously stirred down
Aqueous slkali in, after completion of dropwise addition solution adjust pH=10；
Step 3, by above-mentioned reaction solution, crystallization 6h, crystallization terminate under 100 DEG C of stirring conditions, and reaction solution is through repeatedly centrifugation water washing
Afterwards, 60 DEG C of dryings in drying box are put into and for 24 hours, obtain Mg2FeAl-LDH catalyst.
2. a kind of application of catalyst described in power 1, which is characterized in that for catalyzing and synthesizing N- [3- aminopropyl -2- hydroxyl second
Sulfuryl] reaction of -4- nitrobenzene sulfonamide.
3. application according to claim 2, which is characterized in that the synthesis N- [3- aminopropyl -2- hydroxyl second sulfone
Base] -4- nitrobenzene sulfonamide reaction response condition is as follows：4- acetamidobenzenesulfonyl chloride, 3- aminopropyl -2- hydroxyethyl sulphur
Ether, glacial acetic acid, hydrogen peroxide be primary raw material, it is raw materials used according to the following ratio：4- acetamidobenzenesulfonyl chloride, 3- aminopropan
Base -2- hydroxyethyl thioether mass ratio is 6：7.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810494243.3A CN108816230A (en) | 2018-05-22 | 2018-05-22 | A kind of novel Mg2FeAl-LDH catalyst and its application |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810494243.3A CN108816230A (en) | 2018-05-22 | 2018-05-22 | A kind of novel Mg2FeAl-LDH catalyst and its application |
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|---|---|
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115487825A (en) * | 2022-08-30 | 2022-12-20 | 北京化工大学 | Furfural reductive amination catalyst and preparation method thereof |
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| JP2006070406A (en) * | 2004-09-06 | 2006-03-16 | Tayca Corp | Fiber material containing lamellar double hydroxide incorporating ascorbic acid |
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| CN115487825A (en) * | 2022-08-30 | 2022-12-20 | 北京化工大学 | Furfural reductive amination catalyst and preparation method thereof |
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Application publication date: 20181116 |