CN109824525A - A kind of method that p-tert-butylphenol nitrification synthesizes adjacent amino-p-tert butyl phenol - Google Patents
A kind of method that p-tert-butylphenol nitrification synthesizes adjacent amino-p-tert butyl phenol Download PDFInfo
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Abstract
The invention discloses a kind of p-tert-butylphenols to nitrify the method for synthesizing adjacent amino-p-tert butyl phenol, and using adjacent nitro p-tert-butylphenol as raw material, methanol is solvent, and Raney's nickel is catalyst, carries out catalytic hydrogenation reaction in a high pressure reaction kettle；The volume ratio m/v of adjacent nitro p-tert-butylphenol quality and methanol is 1:(10 ~ 12), the mass ratio of catalyst and adjacent nitro p-tert-butylphenol is 1:(20 ~ 30), reaction pressure is 0.4 ~ 0.6Mpa, and reaction temperature is 30 ~ 40 DEG C, and the reaction time is 6 ~ 8h；System is cooled to 20 ~ 30 DEG C, can successively obtain the adjacent amino-p-tert butyl phenol of white powder through filters pressing, concentration, crystallization, centrifugation, drying under inert gas protection.The present invention can be reacted to obtain purity and yield higher adjacent amino-p-tert butyl phenol under the conditions of lower temperature and pressure, oxidation is not susceptible to production process to guarantee product coloration, wastewater flow rate is few, and solvent methanol is reusable, pollutes the advantages that small and controllable.
Description
Technical field
The invention belongs to technical field of organic synthesis, are related to a kind of synthetic method of adjacent amino-p-tert butyl phenol, especially
It is to be related to a kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol.
Background technique
Adjacent amino-p-tert butyl phenol, molecular formula C10H15NO structural formula is as follows:
Sterling neighbour's amino-p-tert butyl phenol is white powder, and exposed placement color can gradually deepen to become for a long time in air
Grey, fusing point are 164 ~ 166 DEG C, are a kind of important organic chemical industry's intermediates and industrial chemicals, are synthesis fluorescent whitening agents
The key intermediate of bis- [5- tert-butyl -2- benzene fourth oxazolyl] thiophene (OB) of 2,5-.
The quality of adjacent amino-p-tert butyl phenol is directly related to the quality of OB, and China's fluorescent whitening agent OB quality is simultaneously
It is unstable, it is unstable the main reason for be adjacent amino-p-tert butyl phenol unstable quality.Currently, neighbour available on the market
The purity of amino-p-tert butyl phenol is generally 92 ~ 95%, and all grays, this is because system is in post-processing stages after reaction
Caused by being oxidized.
Currently, adjacent amino-p-tert butyl phenol synthesis route mainly have it is several following:
(1) sulfide reduction method: making raw material with p-tert-butylphenol, and adjacent amino is made with sodium sulfide reducing again after mixed acid nitrifies
P-tert-butylphenol；This method can generate a large amount of waste water due to using mixed acid and sulfide, seriously polluted, be unfavorable for realizing work
Industry metaplasia produces；
(2) electrolytic reduction: p-tert-butylphenol electroreduction in a cell, intermediate product is to tert-butyl hydroxy aniline through weight
Row obtains adjacent amino-p-tert butyl phenol；The method power consumption is very big, and production cost is too high, is unfavorable for industrialized production；
(3) iron powder reducing method: adjacent nitro p-tert-butylphenol in acidic aqueous solution through iron powder reducing, after being filtered to remove iron cement,
Burnt sodium nitrite is added into mother liquor, then obtains product neighbour's amino to tert-butyl benzene after the processing such as cooling, recrystallization, drying
Phenol；It is seriously polluted because generating many reluctant wastes although the method process is simple, it is unfavorable for industrialized production；
(4) hydrazine hydrate reduction method: using with compared with the nitro in the hydrazine hydrate reduction adjacent nitro p-tert-butylphenol of strong reducing property
For amino, then after the processing such as cooling, recrystallization, drying obtain adjacent amino-p-tert butyl phenol；Although there is the method reaction to hold
It easily carries out, the advantages that yield is higher, less pollution, but because hydrazine hydrate is a kind of high-risk compound, and price itself is too high, puts
Mass production is at high cost and has quite high risk, is unfavorable for industrialized production；
(5) hydrogenating reduction method: using adjacent nitro p-tert-butylphenol for raw material, under the action of hydrogenation catalyst, utilizes hydrogen
Nitro in adjacent nitro p-tert-butylphenol is reduced to amino, then obtains adjacent amino after the processing such as cooling, recrystallization, drying
P-tert-butylphenol.The method reaction selectivity is high, high income, reacts and is easy to carry out, and the three wastes are few, and pollution is small, is a kind of typical
Greenization reaction is a kind of current domestic technology widely developed and promoted.But because in current industrialized production, reaction is warm mostly
Degree is 90 DEG C or more, and reaction pressure is 1.0MPa or more, and hydrogen is easy leakage and serious accident occurs, and equipment is wanted in reaction
It asks higher, therefore needs constantly to reduce reaction temperature and pressure under conditions of guaranteeing reaction efficiency, finding out has higher catalysis effect
The catalyst of rate.
CN200910154478.9 discloses a kind of synthetic method of adjacent amino-p-tert butyl phenol, and this method is adjacent nitro
P-tert-butylphenol is under the conditions of ammonia and aliphatic alcohol solvent, using Raney's nickel as catalyst, in 1.0 ~ 3.0Mpa, 90 ~ 150 DEG C of conditions
Lower reaction；Post-reaction treatment is rotated, is recrystallized, filtering is dried to obtain adjacent amino-p-tert butyl phenol by filtering.But by
Ammonia in raw material has very big penetrating odor and is difficult to control, and has very big harm, such technology to human and environment
Even if enterprise reluctantly run, can also be turned off by Environmental Protection Agency, the method not only also make the means of production and equipment by pollution of ecological environment
At great waste, laboratory lab scale is fine, and the applicability and promotional value of industrialized production are poor.
Summary of the invention
In order to solve the problems in the existing technology, the invention discloses a kind of adjacent nitro p-tert-butylphenols, and hydrogen to be added to close
At the method for adjacent amino-p-tert butyl phenol, can be reacted to obtain under the conditions of lower reaction temperature and reaction pressure pure
Degree and the higher adjacent amino-p-tert butyl phenol of yield, there is production process to be not susceptible to oxidation to guarantee product coloration, give up
Water is few, and reaction raw materials methanol is reusable, pollutes the advantages that small and controllable.
The present invention is achieved through the following technical solutions:
The invention discloses a kind of methods of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, with adjacent nitre
Base p-tert-butylphenol, using Raney's nickel as catalyst, carries out catalytic hydrogenation using methanol as solvent for raw material in a high pressure reaction kettle
Reaction；Adjacent nitro p-tert-butylphenol quality and methanol volume ratio are 1:(10 ~ 12), catalyst and adjacent nitro p-tert-butylphenol
Mass ratio be 1:(20 ~ 30), reaction pressure be 0.4 ~ 0.6Mpa, reaction temperature be 30 ~ 40 DEG C, the reaction time be 6 ~ 8h, body
System is cooled to 20 ~ 30 DEG C, can successively obtain the neighbour of white powder through filters pressing, concentration, crystallization, centrifugation, drying under an inert atmosphere
Amino-p-tert butyl phenol.
The mass ratio of catalyst and adjacent nitro p-tert-butylphenol is 1:(20 ~ 30 as a preferred implementation manner).
Preferably, reaction temperature is 30 ~ 40 DEG C.
The inert gas is nitrogen as a preferred implementation manner,.
The synthetic method of adjacent amino-p-tert butyl phenol of the invention is first proportionally added into adjacent nitro into autoclave
P-tert-butylphenol, methanol, Raney's nickel are displaced then with after the air in inert gas discharge autoclave with hydrogen
Inert atmosphere in autoclave, and control using hydrogen is passed through the pressure of reaction system.Synthetic route of the invention is such as
Under:
Compared with prior art, the present invention having the following beneficial effects:
(1) simple process, the yield of products obtained therefrom are up to 95%, and purity is up to 99.5%, hence it is evident that are higher than commercially available and prior art energy
The purity enough reached；
(2) post-processing does not have waste water and gas substantially, and the methanol in centrifuge mother liquor can recycle and reuse, and catalyst can also weigh
It is multiple to utilize, greatly reduce production cost；The minimal amount of water phase in the bottom of a pan repeats after our wastewater treatment equipment processing
It utilizes, further reduces costs；It is very friendly to environment；
(3) whole inert gas shielding, ensure that the purity and quality of final products, avoid existing commercially available adjacent amino to uncle
Butylphenol in last handling process due to oxidation caused by color change；
(4) hydrogenation technique low-temp low-pressure, it is economic and environment-friendly, it is very suitable to industrialized production.
Detailed description of the invention
Fig. 1 is the liquid chromatogram of the adjacent amino-p-tert butyl phenol of the present invention.
From figure 1 it appears that being impurity peaks in 2min, 8min, 10min, 11min or so, the sum of peak area accounting is
0.2776%, 9min or so are product peak, and peak area 99.7224%, i.e., adjacent amino-p-tert butyl phenol product is pure in explanatory diagram 1
Degree is 99.7% or so.
Specific embodiment
It is described below for disclosing the present invention so that those skilled in the art can be realized the present invention.It is excellent in being described below
Embodiment is selected to be only used as illustrating, it may occur to persons skilled in the art that other obvious modifications.
Embodiment 1
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4.0g, autoclave examination
It is replaced 5 times after closely sealed lattice with nitrogen, hydrogen is replaced 8 times, and 30 DEG C of temperature control, being passed through hydrogen to autoclave intermittent makes high pressure
Pressure in reaction kettle is maintained at 0.4 MPa, reaction time 8h；System after reaction is cooled to 30 DEG C, nitrogen is by reaction under high pressure
Reaction system in kettle filters after being transferred to conical flask, and filtrate is transferred to 500ml single port bottle in batches and is concentrated into 240ml, is then added dropwise
80ml water is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, and system filters, the Shui Hejia that filtrate is 1:10 with 80ml volume ratio
The mixed solution of alcohol elutes, and solid is dried to obtain adjacent amino-p-tert butyl phenol with drying box after suction filtration, and yield 94.7% is pure
Degree is 99.2%.
Embodiment 2
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4g, autoclave examination it is close
It is replaced 5 times after qualification with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and into autoclave
Intermittence, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.4MPa, reaction time 7h；System after reaction is cooled to
30 DEG C, nitrogen filters after the reaction system in autoclave is transferred to conical flask, and filtrate is transferred to the concentration of 500ml single port bottle in batches
To 240ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, filtrate 80ml volume
Mixed solution than water and methanol for 1:10 elutes, and solid is dried to obtain adjacent amino to tert-butyl benzene with drying box after suction filtration
Phenol, yield 95.23%, purity 99.5%.
Embodiment 3
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4g, autoclave examination it is close
It is replaced 5 times after qualification with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 40 DEG C, and into autoclave
Intermittence, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.4MPa, reaction time 6h；System after reaction is cooled to
30 DEG C, nitrogen filters after the reaction system in autoclave is transferred to conical flask, and filtrate is transferred to the concentration of 500ml single port bottle in batches
To 240ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, filtrate 80ml volume
Mixed solution than water and methanol for 1:10 elutes, and solid is dried to obtain adjacent amino to tert-butyl benzene with drying box after suction filtration
Phenol, yield 95.13%, purity 99.32%.
Embodiment 4
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4g, autoclave examination it is close
It is replaced 5 times after qualification with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and into autoclave
Intermittence, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.5MPa, reaction time 7h；System after reaction is cooled to
It 30 DEG C, is filtered after the reaction system in autoclave is transferred to conical flask with nitrogen, it is dense that filtrate is transferred to 500ml single port bottle in batches
It is reduced to 240ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, filtrate 80ml body
Product is eluted than the mixed solution of the water and methanol that are 1:10, and solid is dried to obtain adjacent amino to tert-butyl benzene with drying box after suction filtration
Phenol, yield 94.82%, purity 99.1%.
Embodiment 5
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4g, autoclave examination it is close
It is replaced 5 times after qualification with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and into autoclave
Intermittence, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.6MPa, reaction time 6h；System after reaction is cooled to
It 30 DEG C, is filtered after the reaction system in autoclave is transferred to conical flask with nitrogen, it is dense that filtrate is transferred to 500ml single port bottle in batches
It is reduced to 240ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, filtrate 80ml body
Product is eluted than the mixed solution of the water and methanol that are 1:10, and solid is dried to obtain adjacent amino to tert-butyl benzene with drying box after suction filtration
Phenol, yield 95.20%, purity 99.60%.
Embodiment 6
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4g, autoclave examination it is close
It is replaced 5 times after qualification with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and into autoclave
Intermittence, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.6MPa, reaction time 6h；System after reaction is cooled to
It 30 DEG C, is filtered after the reaction system in autoclave is transferred to conical flask with nitrogen, it is dense that filtrate is transferred to 500ml single port bottle in batches
It is reduced to 160ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, filtrate 80ml body
Product is eluted than the mixed solution of the water and methanol that are 1:10, and solid is dried to obtain adjacent amino to tert-butyl benzene with drying box after suction filtration
Phenol, yield 95.06%, purity 99.35%.
Embodiment 7
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 4g, autoclave examination it is close
It is replaced 5 times after qualification with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and into autoclave
Intermittence, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.6MPa, reaction time 6h；System after reaction is cooled to
It 30 DEG C, is filtered after the reaction system in autoclave is transferred to conical flask with nitrogen, it is dense that filtrate is transferred to 500ml single port bottle in batches
It is reduced to 320ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, filtrate 80ml body
Product is eluted than the mixed solution of the water and methanol that are 1:10, and solid is dried to obtain adjacent amino to tert-butyl benzene with drying box after suction filtration
Phenol, yield 94.87%, purity 98.85%.
Embodiment 8
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 3.0g, autoclave examination
It is replaced 5 times after closely sealed lattice with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and to autoclave
Intermittent, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.6MPa, reaction time 6h；System cools down after reacting
It to 30 DEG C, is filtered after the reaction system in autoclave is transferred to conical flask with nitrogen, filtrate is transferred to 500ml single port bottle in batches
It is concentrated into 240ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, and filtrate uses 80ml
The mixed solution of water and methanol that volume ratio is 1:10 elutes, and solid is dried to obtain adjacent amino to tert-butyl with drying box after suction filtration
Phenol, yield 95.24%, purity 98.95%.
Embodiment 9
A kind of method of adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol, this method is in 1000ml high
Press reaction kettle in be added adjacent nitro p-tert-butylphenol 80g(0.4098mol), methanol 800mL, Raney's nickel 2.8g, autoclave examination
It is replaced 5 times after closely sealed lattice with nitrogen, hydrogen is replaced 8 times, the temperature of autoclave is controlled at 35 DEG C, and to autoclave
Intermittent, which is passed through hydrogen, makes the pressure in autoclave be maintained at 0.6MPa, reaction time 6h；System cools down after reacting
It to 30 DEG C, is filtered after the reaction system in autoclave is transferred to conical flask with nitrogen, filtrate is transferred to 500ml single port bottle in batches
It is concentrated into 240ml, 80ml water is then added dropwise, is cooled to 0 DEG C of heat preservation 3h after 20min is sufficiently stirred, system filters, and filtrate uses 80ml
The mixed solution of water and methanol that volume ratio is 1:10 elutes, and solid is dried to obtain adjacent amino to tert-butyl with drying box after suction filtration
Phenol, yield 95.14%, purity 98.65%.
The basic principles, main features and advantages of the present invention have been shown and described above.The technology of the industry
Personnel are it should be appreciated that the present invention is not limited to the above embodiments, and what is described in the above embodiment and the description is only the present invention
Principle, various changes and improvements may be made to the invention without departing from the spirit and scope of the present invention, these variation and
Improvement is both fallen in the range of claimed invention.The present invention claims protection scope by appended claims and its
Equivalent defines.
Claims (5)
1. a kind of method that p-tert-butylphenol nitrification synthesizes adjacent amino-p-tert butyl phenol, it is characterised in that: with adjacent nitro pair
Tert-butyl phenol is raw material, and using methanol as solvent, using Raney's nickel as catalyst, it is anti-to carry out catalytic hydrogenation in a high pressure reaction kettle
It answers；Adjacent nitro p-tert-butylphenol quality and methanol volume ratio are 1:(10 ~ 12), catalyst and adjacent nitro p-tert-butylphenol
Mass ratio is 1:(20 ~ 30), reaction pressure is 0.4 ~ 0.6Mpa, and reaction temperature is 30 ~ 40 DEG C, and the reaction time is 6 ~ 8h, system
20 ~ 30 DEG C are cooled to, can successively obtain the adjacent ammonia of white powder through filters pressing, concentration, crystallization, centrifugation, drying under an inert atmosphere
Base p-tert-butylphenol.
2. the method that p-tert-butylphenol nitrification as described in claim 1 synthesizes adjacent amino-p-tert butyl phenol, it is characterised in that:
Before reaction starts, adjacent nitro p-tert-butylphenol quality and methanol volume ratio are 1:(10 ~ 12 in added raw material).
3. the method that p-tert-butylphenol nitrification as described in claim 1 synthesizes adjacent amino-p-tert butyl phenol, it is characterised in that:
The mass ratio of catalyst and adjacent nitro p-tert-butylphenol is 1:(20 ~ 30).
4. the method that p-tert-butylphenol nitrification as described in claim 1 synthesizes adjacent amino-p-tert butyl phenol, it is characterised in that:
Reaction temperature is 30 ~ 40 DEG C.
5. such as the side of any adjacent nitro p-tert-butylphenol hydrogenation synthesis neighbour's amino-p-tert butyl phenol in claim 1 ~ 4
Method, it is characterised in that: the inert gas is nitrogen.
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