CN108927153A - It is a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol - Google Patents
It is a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol Download PDFInfo
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- CN108927153A CN108927153A CN201810741059.4A CN201810741059A CN108927153A CN 108927153 A CN108927153 A CN 108927153A CN 201810741059 A CN201810741059 A CN 201810741059A CN 108927153 A CN108927153 A CN 108927153A
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- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/60—Platinum group metals with zinc, cadmium or mercury
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
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Abstract
The invention discloses a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol, and the catalyst is Pt-SnO2/ C catalyst.Catalyst Pt-SnO2/ C promotes p-nitrophenyl ethyl alcohol and hydrazine hydrate to obtain 4- Aminophenethyl alcohol by reduction reaction.Under neutral or weak basic condition, Pt-SnO2/ C Compounds with Hydrazine Hydrate Catalyzed nitro compound reducing is amino-compound, and Pt first is catalyzed hydrazine betatopic, resolves into nitrogen and reactive hydrogen ions, and then p-nitrophenyl ethyl alcohol obtains electronics under the action of reactive hydrogen ions and obtains product Aminophenethyl alcohol through three step reduction reactions.Homemade Pt-SnO2/ C is the catalyst of hydrazine hydrate reduction Nitrophenethyl alcohol, and reaction condition is mild, high catalytic efficiency, and the purity and yield of product have reached ideal effect.
Description
Technical field
The present invention relates to a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol, belongs to chemical industry synthesis field.
Background technique
4- Aminophenethyl alcohol (4-amino phenethyl alcohol) CAS:104-10-9 is in the important medicine of one kind
Mesosome can be used for synthesizing p-hydroxyphenylethanol, and then synthesize drugs and other perfume (or spice) such as metoprolol, rhodioside, betaxolol
Material, organic synthesis intermediate.The problem of preparing equal amido phenenyl alcohol technique for traditional benzyl carbinol synthetic method: ortho position is different
The structure scale of construction is big, and synthesis technology is complicated, and total yield of products is low, and the synthetic method of 4- Aminophenethyl alcohol mainly has two by raw material difference
Class: being raw material and using bata-phenethyl alcohol as raw material using paranitrophenylacetic acid.Two methods are to first pass through reaction to obtain p-nitrophenyl
Then ethyl alcohol obtains 4- Aminophenethyl alcohol through reduction reaction.But since reaction step is more, equipment will be increased in the industrial production and thrown
Rate, and ortho isomer is produced in nitration reaction, the total recovery of equal amido phenenyl alcohol is greatly reduced, to hinder
It industrializes paces.Therefore, 4- Aminophenethyl alcohol new technique for synthesizing is explored, it is very urgent to find suitable catalyst.
Summary of the invention
The purpose of the present invention is to provide a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol, and the catalyst is in optimization item
The reduction reaction of p-nitrophenyl ethyl alcohol and hydrazine hydrate, product yield with higher can be catalyzed under part.
One is a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol, and the catalyst is Pt-SnO2/ C catalyst.
The Pt-SnO2/ C catalyst the preparation method is as follows:
Step 1, by 0.2gSnCl2·2H25ml deionized water, ultrasonic 5min is added in O and 50ml ethylene glycol ultrasonic mixing 0.5h
It is uniformly mixed, microwave 10min；
It is step 2, the mixed solution of above-mentioned preparation and the abundant ultrasonic mixing of 2g carbon black is uniform, it is stirred overnight, filters, 80 DEG C of vacuum
Dry 12 hours to get SnO2/ C complex carrier；
Step 3, into the 100ml beaker containing 25ml ethylene glycol, be added 10ml contain 0.001molH2PtC16Ethylene glycol it is molten
Liquid adds the above-mentioned SnO prepared2/ C complex carrier, ultrasonic wave disperse 30 min；
After being uniformly dispersed, the ethylene glycol solution of the KOH of concentration 0.1M is added dropwise in step 4, is adjusted pH=10 of solution, is continued to surpass
Sound disperses 30min, keeps mixture fully dispersed uniformly；
Above-mentioned mixed slurry is put into micro-wave oven by step 5, using microwave heating 20s, stops l0s, and 6 times repeatedly, slurry takes out cold
But it filters, with distillation water washing three times to no Cl-, 80 DEG C of vacuum drying 12h are to get Pt-SnO2/ C catalyst.
The utility model has the advantages that p-nitrophenyl ethyl alcohol and hydrazine hydrate are in catalyst Pt-SnO2It is obtained under the action of/C by reduction reaction
4- Aminophenethyl alcohol.Under neutral or weak basic condition, Pt-SnO2/ C Compounds with Hydrazine Hydrate Catalyzed nitro compound reducing is amino chemical combination
Object, first Pt are catalyzed hydrazine betatopic, resolve into nitrogen and reactive hydrogen ions, then p-nitrophenyl ethyl alcohol is in reactive hydrogen ions
Effect is lower that electronics obtains product Aminophenethyl alcohol through three step reduction reactions.Homemade Pt-SnO2/ C is hydrazine hydrate reduction nitre
The catalyst of base benzyl carbinol, reaction condition is mild, high catalytic efficiency, and the purity and yield of product have reached ideal effect.
Specific embodiment
Embodiment 1
Pt-SnO2/ C catalyst the preparation method is as follows:
Step 1, by 0.2gSnCl2·2H25ml deionized water, ultrasonic 5min is added in O and 50ml ethylene glycol ultrasonic mixing 0.5h
It is uniformly mixed, microwave 10min；
It is step 2, the mixed solution of above-mentioned preparation and the abundant ultrasonic mixing of 2g carbon black is uniform, it is stirred overnight, filters, 80 DEG C of vacuum
Dry 12 hours to get SnO2/ C complex carrier；
Step 3, into the 100ml beaker containing 25ml ethylene glycol, be added 10ml contain 0.001molH2PtC16Ethylene glycol it is molten
Liquid adds the above-mentioned SnO prepared2/ C complex carrier, ultrasonic wave disperse 30 min；
After being uniformly dispersed, the ethylene glycol solution of the KOH of concentration 0.1M is added dropwise in step 4, is adjusted pH=10 of solution, is continued to surpass
Sound disperses 30min, keeps mixture fully dispersed uniformly；
Above-mentioned mixed slurry is put into micro-wave oven by step 5, using microwave heating 20s, stops lOs, and 6 times repeatedly, slurry takes out cold
But it filters, with distillation water washing three times to no Cl-, 80 DEG C of vacuum drying 12h are to get Pt-SnO2/ C catalyst.
In the application of synthesis 4- Aminophenethyl alcohol:
Step 1, to equipped with thermometer, mechanical stirring, reflux condensing tube 1000ml three-necked flask in, be added 10ml concentration 0.1M
Hydrochloric acid solution, 500ml methanol and 2g catalyst Pt-SnO2/ C is warming up to 68 DEG C；
P-nitrophenyl ethyl alcohol 100g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 75g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；
Step 3, thin-layered chromatography monitoring reaction, until raw material point disappears, reaction terminates, and cold filtration removes in reaction mixture
Methanol is recycled in catalyst, air-distillation；
Above-mentioned mixed system is cooled to 20 DEG C by step 4, and suitable quantity of water and a small amount of NaOH solution, chilled suction filtration is added, and vacuum is done
It is dry to obtain white 4- Aminophenethyl alcohol.
The Pt-SnO2/ C catalyst the preparation method is as follows:
Step 1, by 0.2gSnCl2·2H25ml deionized water, ultrasonic 5min is added in O and 50ml ethylene glycol ultrasonic mixing 0.5h
It is uniformly mixed, microwave 10min；
It is step 2, the mixed solution of above-mentioned preparation and the abundant ultrasonic mixing of 2g carbon black is uniform, it is stirred overnight, filters, 80 DEG C of vacuum
Dry 12 hours to get SnO2/ C complex carrier；
Step 3, into the 100ml beaker containing 25ml ethylene glycol, be added 10ml contain 0.001molH2PtC16Ethylene glycol it is molten
Liquid adds the above-mentioned SnO prepared2/ C complex carrier, ultrasonic wave disperse 30 min；
After being uniformly dispersed, the ethylene glycol solution of the KOH of concentration 0.1M is added dropwise in step 4, is adjusted pH=10 of solution, is continued to surpass
Sound disperses 30min, keeps mixture fully dispersed uniformly；
Above-mentioned mixed slurry is put into micro-wave oven by step 5, using microwave heating 20s, stops lOs, and 6 times repeatedly, slurry takes out cold
But it filters, with distillation water washing three times to no Cl-, 80 DEG C of vacuum drying 12h are to get Pt-SnO2/ C catalyst.
Embodiment 2
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 80g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 75g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 3
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 60g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 75g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 4
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 50g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 75g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 5
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 40g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 75g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 6
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 100g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 65g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 7
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 100g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 55g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 8
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 100g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 45g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 9
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 100g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 35g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；Remaining step is the same as embodiment 1.
Embodiment 10
Synthesize 4- Aminophenethyl alcohol step:
P-nitrophenyl ethyl alcohol 100g is added to above-mentioned ethanol solution in step 2, adjusts pH=7 with 30% concentration NaOH, after mixing evenly
Hydrazine hydrate 25g, temperature rising reflux reaction is slowly added dropwise, reflux temperature is 68 DEG C；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, uses the Pt of equivalent as catalyst, remaining step and reality
It is identical to apply example 1.
Reference examples 2
It is with 1 difference of embodiment: in the synthesis step 1 of intermediate, does not add catalyst Pt-SnO2/ C, remaining step
It is identical with embodiment 1.
Reference examples 3
It is with 1 difference of embodiment: in the synthesis step 1 of catalyst, does not add SnCl2·2H2O, remaining step and reality
It is identical to apply example 1.
Reference examples 4
It is with 1 difference of embodiment: in the synthesis step 1 of catalyst, with the FeCl of equivalent2·4H2O replaces SnCl2·
2H2O, remaining step are identical with embodiment 1.
Reference examples 5
It is with 1 difference of embodiment: in the synthesis step 2 of catalyst, the mixed solution of above-mentioned preparation and 2g white carbon black is filled
Divide ultrasonic mixing uniform, remaining step is identical with embodiment 1.
Reference examples 6
It is with 1 difference of embodiment: in the synthesis step 2 of catalyst, the mixed solution of above-mentioned preparation and 2g kaolin is filled
Divide ultrasonic mixing uniform, remaining step is identical with embodiment 1.
Reference examples 7
It is with 1 difference of embodiment: in the synthesis step 2 of catalyst, SnCl2·2H2O, carbon black mass ratio is 1:1；Remaining
Step is identical with embodiment 1.
Reference examples 8
It is with 1 difference of embodiment: in the synthesis step 2 of catalyst, SnCl2·2H2O, carbon black mass ratio is 10:1；Remaining
Step is identical with embodiment 1.
Reference examples 9
It is with 1 difference of embodiment: in the synthesis step 4 of catalyst, adjusts pH=7 of solution, remaining step and embodiment 1
It is identical.
Reference examples 10
It is with 1 difference of embodiment: in the synthesis step 4 of catalyst, adjusts pH=3 of solution, 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
| 4- Aminophenethyl alcohol yield/% | |
| Embodiment 1 | 99.7 |
| Embodiment 2 | 81.0 |
| Embodiment 3 | 74.3 |
| Embodiment 4 | 66.3 |
| Embodiment 5 | 70.2 |
| Embodiment 6 | 60.7 |
| Embodiment 7 | 54.5 |
| Embodiment 8 | 67.3 |
| Embodiment 9 | 61.6 |
| Embodiment 10 | 53.9 |
| Reference examples 1 | 41.9 |
| Reference examples 2 | 35.4 |
| Reference examples 3 | 48.5 |
| Reference examples 4 | 50.2 |
| Reference examples 5 | 57.1 |
| Reference examples 6 | 40.7 |
| Reference examples 7 | 49.0 |
| Reference examples 8 | 59.1 |
| Reference examples 9 | 61.0 |
| Reference examples 10 | 48.5 |
The experimental results showed that catalyst has good catalytic effect to the reduction reaction of p-nitrophenyl ethyl alcohol and hydrazine hydrate, anti-
One timing of condition is answered, intermediate yield is higher, and catalytic performance is better, otherwise poorer；P-nitrophenyl ethyl alcohol, hydrazine hydrate mass ratio are
When 5:4, other ingredients are fixed, and synthetic effect is best, with embodiment 1 the difference lies in that embodiment 2 to embodiment 10 changes respectively
The dosage and proportion of primary raw material p-nitrophenyl ethyl alcohol, hydrazine hydrate in spite of certain effect, but are not so good as 1 high income of embodiment；It is right
As usual 1 catalyst Pt-SnO is not added to reference examples 22/ C is simultaneously replaced with Pt, other steps are identical, and product is caused to be received
Rate is substantially reduced, and it is very big to illustrate that composite catalyst influences the product of reaction；Reference examples 3 to the equivalent of reference examples 4 FeCl2·
4H2O replaces SnCl2·2H2O, effect is still bad, illustrates SnCl2·2H2The synthesis component effect that O does carrier is more preferable；Reference examples
5 replace carbon black to the white carbon black of reference examples 8 and kaolin respectively and change SnCl2·2H2O, carbon black mass ratio, catalytic effect are bright
It is aobvious to be deteriorated, illustrate carbon black-supported and both with compare catalytic performance influence it is very big；After reference examples 9 reduce reaction to reference examples 10
The activity of the PH of mixed system, catalyst change, and reaction effect is obviously deteriorated, and product yield is substantially reduced；Therefore it uses
Catalyst of the invention has excellent catalytic effect to the synthetic reaction of intermediate 4- Aminophenethyl alcohol.
Claims (2)
1. a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol, which is characterized in that the catalyst is Pt-SnO2/ C catalysis
Agent.
2. a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol according to claim 1, which is characterized in that
The Pt-SnO2/ C catalyst the preparation method is as follows:
Step 1, by 0.2gSnCl2·2H2O and 50ml ethylene glycol ultrasonic mixing 0.5h, is added 5ml deionized water, and ultrasonic 5min is mixed
It closes uniformly, microwave 10min；
It is step 2, the mixed solution of above-mentioned preparation and the abundant ultrasonic mixing of 2g carbon black is uniform, it is stirred overnight, filters, 80 DEG C of vacuum
Dry 12 hours to get SnO2/ C complex carrier；
Step 3, into the 100ml beaker containing 25ml ethylene glycol, be added 10ml contain 0.001molH2PtC16Ethylene glycol it is molten
Liquid adds the above-mentioned SnO prepared2/ C complex carrier, ultrasonic wave disperse 30 min；
After being uniformly dispersed, the ethylene glycol solution of the KOH of concentration 0.1M is added dropwise in step 4, is adjusted pH=10 of solution, is continued to surpass
Sound disperses 30min, keeps mixture fully dispersed uniformly；
Above-mentioned mixed slurry is put into micro-wave oven by step 5, using microwave heating 20s, stops lOs, and 6 times repeatedly, slurry takes out cold
But it filters, with distillation water washing three times to no Cl-, 80 DEG C of vacuum drying 12h are to get Pt-SnO2/ C is urged.
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| CN201810741059.4A CN108927153A (en) | 2018-07-08 | 2018-07-08 | It is a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol |
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|---|---|---|---|
| CN201810741059.4A CN108927153A (en) | 2018-07-08 | 2018-07-08 | It is a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol |
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| CN201810741059.4A Pending CN108927153A (en) | 2018-07-08 | 2018-07-08 | It is a kind of for synthesizing the catalyst of 4- Aminophenethyl alcohol |
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