CN108722465A - A kind of NiFe@CN catalyst and its application - Google Patents

A kind of NiFe@CN catalyst and its application Download PDF

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Publication number
CN108722465A
CN108722465A CN201810554946.0A CN201810554946A CN108722465A CN 108722465 A CN108722465 A CN 108722465A CN 201810554946 A CN201810554946 A CN 201810554946A CN 108722465 A CN108722465 A CN 108722465A
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catalyst
nife
aminopropyl
solution
added dropwise
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张素兰
朱亚飞
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Fuzhou Xingchuang Yun Da Xin Mstar Technology Ltd
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Fuzhou Xingchuang Yun Da Xin Mstar Technology Ltd
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    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/24—Nitrogen compounds
    • 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
    • B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
    • B01J37/08—Heat treatment
    • B01J37/082—Decomposition and pyrolysis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
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  • Thermal Sciences (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses a kind of NiFe@CN catalyst and in the application for synthesizing N- [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides; NiFe@CN catalyst with core-casing structure; the preparation process is without being passed through hydrogen; suitable ferronickel ratio and nickel content are conducive to generate smaller catalyst granules; to make it have the ability of stronger catalytic activation; there is excellent catalytic effect, product yield to be largely increased the formylation reaction of 3- aminopropyl -2- hydroxyethyl thioethers.

Description

A kind of NiFe@CN catalyst and its application
Technical field
The present invention relates to a kind of NiFe@CN catalyst and its applications, belong to the field of catalyzing and synthesizing.
Background technology
The structural formula of N- [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides：
It is important reactive dye, N- [3- aminopropyl -2- hydroxyethyls sulfenyl] - The high synthetic ratio of 4- nitrobenzamides is synthesized dependent on catalyst, seeks a kind of catalyst promotion N- [3- of high activity Aminopropyl -2- hydroxyethyls sulfenyl] synthetic ratios of -4- nitrobenzamides is highly desirable.
Invention content
The purpose of the present invention is to provide a kind of NiFe@CN catalyst, which can be catalyzed 4- nitre with optimal conditions The reaction of base chlorobenzoyl chloride and 3- aminopropyl -2- hydroxyethyl thioethers has higher product yield.
A kind of NiFe@CN catalyst, which is characterized in that preparation method is as follows：
Step 1, by 1.2g Ni（NO3）2·6H2O and 0.8g Fe（NO3）3·9H20 uses 100ml deionized water dissolvings in beaker In, make [Fe3+]=0.02mo1·L-1, it is solution A, 0.4g NaOH and 0.4g Na is added in 100m1 deionized waters2C03, For solution B；
Above two solution is slowly mixed together and is added in colloid mill by step 2 at room temperature, and control rotating speed is 3000rpm, Muddy liquid is obtained, first centrifuges liquid, rear washing is until pH=7；
Step 3 then by centrifugation product be scattered in 500ml four-hole bottles, be added appropriate amount of deionized water, ultrasonic 3min, crystallization 6h, Crystallization temperature is 60 DEG C, is centrifuged after crystallization and obtains Ni2Fe-LDH；
Step 4, in mortar by Ni2Fe-LDH and melamine in mass ratio 1:It is fully ground after 3 mixing, then in N2Protection It is calcined in pipe type stove, heating rate is 50 DEG C of min-1, 550 DEG C of target temperature, soaking time 4h obtains after calcination NiFe@CN catalyst.
NiFe@CN catalyst is answered in synthesis N- [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides With.
Advantageous effect：The present invention provides a kind of NiFe@CN catalyst, are successfully prepared not using nucleation crystallization isolation method Nickel-ferric spinel in proportion still keeps itself and the compound rear crystal form of melamine；By presoma from also in nitrogen atmosphere Former method is successfully prepared NiFe@CN catalyst with core-casing structure, and the preparation process is without being passed through hydrogen, the energy saving and side of preparation Method is more novel, and suitable ferronickel ratio and nickel content are conducive to generate smaller catalyst granules, relatively strong to make it have The ability of catalytic activation has excellent catalytic effect, product to the formylation reaction of 3- aminopropyl -2- hydroxyethyl thioethers Yield is largely increased, and 4- nitrobenzoyl chlorides and 3- aminopropyl -2- hydroxyethyl thioethers are sent out under the effect of the catalyst Midbody product N- [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides are obtained by the reaction in raw formamide.
Specific implementation mode
Embodiment 1
NiFe@CN method for preparing catalyst is as follows：
Step 1, by 1.2g Ni（NO3）2·6H2O and 0.8g Fe（NO3）3·9H20 uses 100ml deionized water dissolvings in beaker In, make [Fe3+]=0.02mo1·L-1, it is solution A, 0.4g NaOH and 0.4g Na is added in 100m1 deionized waters2C03, For solution B；
Above two solution is slowly mixed together and is added in colloid mill by step 2 at room temperature, and control rotating speed is 3000rpm, Muddy liquid is obtained, first centrifuges liquid, rear washing is until pH=7；
Step 3 then by centrifugation product be scattered in 500ml four-hole bottles, be added appropriate amount of deionized water, ultrasonic 3min, crystallization 6h, Crystallization temperature is 60 DEG C, is centrifuged after crystallization and obtains Ni2Fe-LDH；
Step 4, in mortar by Ni2Fe-LDH and melamine in mass ratio 1:It is fully ground after 3 mixing, then in N2Protection It is calcined in pipe type stove, heating rate is 50 DEG C of min-1, 550 DEG C of target temperature, soaking time 4h obtains after calcination NiFe@CN catalyst.
A kind of synthetic method of intermediate N [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides, it is special Sign is that this approach includes the following steps：
8.0g 3- mercaptoethanols are added in step 1 in 250ml four-hole boiling flasks, and 20mL is slowly added dropwise under the conditions of room temperature magnetic agitation 30% sodium hydroxide solution of concentration is added dropwise rear system and is warming up to 50 DEG C, and 21.9g 3- propylamine hydrobromates are stirred with 9ml water Dissolving is mixed, is slowly added dropwise into above-mentioned reaction bulb, 50 DEG C of insulated and stirred 1h are continued；
Step 2 stops stirring after reaction, and solution is in yellowish transparent, and bottom has a small amount of white solid to be precipitated, regulation system PH =10,50 DEG C of supernatant liquid is spin-dried for obtaining thick liquid, with 50 DEG C of recrystallizations of absolute ethyl alcohol, obtains 12.4g light yellow viscous liquids Product 3- aminopropyl -2- hydroxyethyl thioethers；
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 15.0g 3- aminopropyls -2- Hydroxyethyl thioether is dissolved in 80 ml toluene, and 30ml chloroacetic chlorides 1h, TLC is slowly added dropwise after 1.0g NiFe@CN catalyst is added Tracking reaction；
Step 4, the sodium hydroxide solution that lOml concentration 30% is slowly added dropwise to above-mentioned system, to keep solution system pH=10, instead Continue that condition of ice bath is kept to be stirred to react 2h after answering, -4 DEG C of refrigerator cold-storages are stayed overnight, and are filtered after the completion of refrigeration, and filter cake is with anhydrous Ethyl alcohol recrystallization obtains white intermediate N [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides.
Embodiment 2
Step 3, under ice-water bath mechanical agitation, by 14.6g 4- nitrobenzoyl chlorides and 15.0g 3- aminopropyls -2- Hydroxyethyl thioether is dissolved in 80 ml toluene, and 30ml chloroacetic chlorides 1h, TLC is slowly added dropwise after 1.0g NiFe@CN catalyst is added Tracking reaction；Remaining step is the same as embodiment 1.
Embodiment 3
Step 3, under ice-water bath mechanical agitation, by 10.6g 4- nitrobenzoyl chlorides and 15.0g 3- aminopropyls -2- Hydroxyethyl thioether is dissolved in 80 ml toluene, and 30ml chloroacetic chlorides 1h, TLC is slowly added dropwise after 1.0g NiFe@CN catalyst is added Tracking reaction；Remaining step is the same as embodiment 1.
Embodiment 4
Step 3, under ice-water bath mechanical agitation, by 6.6g 4- nitrobenzoyl chlorides and 15.0g 3- aminopropyl -2- hydroxyls Base ethyl thioether is dissolved in 80 ml toluene, be added 1.0g NiFe@CN catalyst after be slowly added dropwise 30ml chloroacetic chlorides 1h, TLC with Track reacts；Remaining step is the same as embodiment 1.
Embodiment 5
Step 3, under ice-water bath mechanical agitation, by 2.6g 4- nitrobenzoyl chlorides and 15.0g 3- aminopropyl -2- hydroxyls Base ethyl thioether is dissolved in 80 ml toluene, be added 1.0g NiFe@CN catalyst after be slowly added dropwise 30ml chloroacetic chlorides 1h, TLC with Track reacts；Remaining step is the same as embodiment 1.
Embodiment 6
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 12.0g 3- aminopropyls -2- Hydroxyethyl thioether is dissolved in 80 ml toluene, and 30ml chloroacetic chlorides 1h, TLC is slowly added dropwise after 1.0g NiFe@CN catalyst is added Tracking reaction；Remaining step is the same as embodiment 1.
Embodiment 7
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 9.0g 3- aminopropyl -2- hydroxyls Base ethyl thioether is dissolved in 80 ml toluene, be added 1.0g NiFe@CN catalyst after be slowly added dropwise 30ml chloroacetic chlorides 1h, TLC with Track reacts；Remaining step is the same as embodiment 1.
Embodiment 8
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 6.0g 3- aminopropyl -2- hydroxyls Base ethyl thioether is dissolved in 80 ml toluene, be added 1.0g NiFe@CN catalyst after be slowly added dropwise 30ml chloroacetic chlorides 1h, TLC with Track reacts；Remaining step is the same as embodiment 1.
Embodiment 9
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 3.0g 3- aminopropyl -2- hydroxyls Base ethyl thioether is dissolved in 80 ml toluene, be added 1.0g NiFe@CN catalyst after be slowly added dropwise 30ml chloroacetic chlorides 1h, TLC with Track reacts；Remaining step is the same as embodiment 1.
Embodiment 10
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 20.0g 3- aminopropyls -2- Hydroxyethyl thioether is dissolved in 80 ml toluene, and 30ml chloroacetic chlorides 1h, TLC is slowly added dropwise after 1.0g NiFe@CN catalyst is added Tracking reaction；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, 3- mercaptoethanols, 3- propylamine hydrobromate mass ratioes are 11：1, remaining step is identical with embodiment 1.
Reference examples 2
It is with 1 difference of embodiment：In the synthesis step 1 of intermediate, 3- mercaptoethanols, 3- propylamine hydrobromate mass ratioes are 1：1, remaining step is identical with embodiment 1.
Reference examples 3
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, Ni is not added（NO3）2·6H2O, remaining step with Embodiment 1 is identical.
Reference examples 4
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 5
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, sodium hydroxide and sodium carbonate mass ratio are 1:10, remaining Step is identical with embodiment 1.
Reference examples 6
It is with 1 difference of embodiment：In the synthesis step 1 of catalyst, sodium hydroxide and sodium carbonate mass ratio are 10:1, remaining Step is identical with embodiment 1.
Reference examples 7
It is with 1 difference of embodiment：In the synthesis step 2 of catalyst, regulation system PH=3；Remaining step and embodiment 1 are complete It is exactly the same.
Reference examples 8
It is with 1 difference of embodiment：In the synthesis step 2 of catalyst, regulation system PH=11；Remaining step and embodiment 1 are complete It is exactly the same.
Reference examples 9
It is with 1 difference of embodiment：In the synthesis step 4 of catalyst, Ni2Fe-LDH and melamine in mass ratio 1:1, Remaining step is identical with embodiment 1.
Reference examples 10
It is with 1 difference of embodiment：In the synthesis step 4 of catalyst, Ni2Fe-LDH and melamine in mass ratio 3:1, Remaining step is identical with embodiment 1.
It is as shown in the table for reaction result under embodiment and reference examples different condition
The experimental results showed that synthetic reaction of the catalyst to 4- nitrobenzoyl chlorides and 3- aminopropyl -2- hydroxyethyl thioethers With good catalytic effect, in one timing of reaction condition, intermediate yield is higher, and catalytic performance is better, otherwise poorer；4- nitre When base chlorobenzoyl chloride, 3- aminopropyl -2- hydroxyethyl thioether mass ratioes are Examples 1 and 2, other dispensings are fixed, synthesis effect Fruit is best, with embodiment 1 the difference lies in that embodiment 3 to embodiment 10 changes primary raw material 4- nitrobenzoyl chlorides, 3- respectively The dosage and proportioning of aminopropyl -2- hydroxyethyl thioethers, have the yield of synthetic product different influences；Reference examples 1 are to right 2 change 3- mercaptoethanols, 3- propylamine hydrobromate mass ratioes as usual, other steps are identical, and product yield is caused obviously to drop It is low, it is very big to illustrate that 3- mercaptoethanols, 3- propylamine hydrobromate mass ratioes influence the product that the first step is reacted；Reference examples 3 are to right 4 do not add Ni as usual（NO3）2·6H2O and Fe（NO3）3·9H20, effect is still bad, illustrates that two kinds of metal salts are catalyst Important composition raw material；Reference examples 5 to reference examples 6 change sodium hydroxide and sodium carbonate mass ratio, and yield is not still high, illustrates alkali The proportioning in source is critically important：The PH of reference examples 7 to 8 system of reference examples changes, and is catalyzed the variation with obvious effects of reaction, in explanation The catalyst effect handled under the conditions of property is preferable；Reference examples 9 are to 10 Ni of reference examples2Fe-LDH and melamine are sent out in mass ratio Changing, the variation of catalyst nucleocapsid ratio, the conversion ratio and selectivity of reaction are very low, and reaction effect is obviously deteriorated, product yield It is still not high；Therefore using the catalyst of the present invention to N- [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides Synthetic reaction have excellent catalytic effect.

Claims (2)

1. a kind of NiFe@CN catalyst, which is characterized in that preparation method is as follows：
Step 1, by 1.2g Ni（NO3）2·6H2O and 0.8g Fe（NO3）3·9H20 uses 100ml deionized water dissolvings in beaker In, make [Fe3+]=0.02mo1·L-1, it is solution A, 0.4g NaOH and 0.4g Na is added in 100m1 deionized waters2C03, For solution B；
Above two solution is slowly mixed together and is added in colloid mill by step 2 at room temperature, and control rotating speed is 3000rpm, Muddy liquid is obtained, first centrifuges liquid, rear washing is until pH=7；
Step 3 then by centrifugation product be scattered in 500ml four-hole bottles, be added appropriate amount of deionized water, ultrasonic 3min, crystallization 6h, Crystallization temperature is 60 DEG C, is centrifuged after crystallization and obtains Ni2Fe-LDH；
Step 4, in mortar by Ni2Fe-LDH and melamine in mass ratio 1:It is fully ground after 3 mixing, then in N2Protection It is calcined in pipe type stove, heating rate is 50 DEG C of min-1, 550 DEG C of target temperature, soaking time 4h obtains after calcination NiFe@CN catalyst.
2. as power 1 catalyst synthesis N- [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides application, Its synthesis condition is as follows：
8.0g 3- mercaptoethanols are added in step 1 in 250ml four-hole boiling flasks, and 20mL is slowly added dropwise under the conditions of room temperature magnetic agitation 30% sodium hydroxide solution of concentration is added dropwise rear system and is warming up to 50 DEG C, and 21.9g 3- propylamine hydrobromates are stirred with 9ml water Dissolving is mixed, is slowly added dropwise into above-mentioned reaction bulb, 50 DEG C of insulated and stirred 1h are continued；
Step 2 stops stirring after reaction, and solution is in yellowish transparent, and bottom has a small amount of white solid to be precipitated, regulation system PH =10,50 DEG C of supernatant liquid is spin-dried for obtaining thick liquid, with 50 DEG C of recrystallizations of absolute ethyl alcohol, obtains 12.4g light yellow viscous liquids Product 3- aminopropyl -2- hydroxyethyl thioethers；
Step 3, under ice-water bath mechanical agitation, by 18.6g 4- nitrobenzoyl chlorides and 15.0g 3- aminopropyls -2- Hydroxyethyl thioether is dissolved in 80 ml toluene, and 30ml chloroacetic chlorides 1h, TLC is slowly added dropwise after 1.0g NiFe@CN catalyst is added Tracking reaction；
Step 4, the sodium hydroxide solution that lOml concentration 30% is slowly added dropwise to above-mentioned system, to keep solution system pH=10, instead Continue that condition of ice bath is kept to be stirred to react 2h after answering, -4 DEG C of refrigerator cold-storages are stayed overnight, and are filtered after the completion of refrigeration, and filter cake is with anhydrous Ethyl alcohol recrystallization obtains white intermediate N [3- aminopropyl -2- hydroxyethyls sulfenyl] -4- nitrobenzamides.
CN201810554946.0A 2018-06-01 2018-06-01 A kind of NiFe@CN catalyst and its application Withdrawn CN108722465A (en)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1271726A (en) * 1999-04-28 2000-11-01 华东理工大学 2-amino-N-[2-[[2-(sulfonate group) ethyl] sulfonyl] ethyl] benzoylamine and its preparing process
CN106732733A (en) * 2017-01-11 2017-05-31 北京化工大学 A kind of application of preparation and its catalysis o-chloronitrobenzene hydrogenation reaction of nitrogen-doped carbon coated core-shell structure dilval nanocatalyst

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1271726A (en) * 1999-04-28 2000-11-01 华东理工大学 2-amino-N-[2-[[2-(sulfonate group) ethyl] sulfonyl] ethyl] benzoylamine and its preparing process
CN106732733A (en) * 2017-01-11 2017-05-31 北京化工大学 A kind of application of preparation and its catalysis o-chloronitrobenzene hydrogenation reaction of nitrogen-doped carbon coated core-shell structure dilval nanocatalyst

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
刘春玲: "基于NiFe-LDH的新型纳米金属催化剂的制备及其性能研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 *

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