CN110105227A - A kind of technique synthesizing 4,4 ' diaminodiphenyl ethers - Google Patents
A kind of technique synthesizing 4,4 ' diaminodiphenyl ethers Download PDFInfo
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- CN110105227A CN110105227A CN201910491820.8A CN201910491820A CN110105227A CN 110105227 A CN110105227 A CN 110105227A CN 201910491820 A CN201910491820 A CN 201910491820A CN 110105227 A CN110105227 A CN 110105227A
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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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- 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
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Abstract
The present invention relates to a kind of synthesis 4, the technique of 4 ' diaminodiphenyl ethers, the solvent that solubility is good is used when its hydrogenation reaction, the solvent of poor solubility is gradually added when crystallization, the solubility of product is reduced, while reducing temperature, the rate of solvent is added by control, with control rate of temperature fall, product crystal is precipitated.By filtering, being dried to obtain product after the completion of crystallization.The product does not need sublimation purification again, and quality fully meets user's requirement, and product is lenticular, does not need to recrystallize.Compared with the prior art, the present invention does not need the process of sublimation purification again and recrystallization, have the advantages that process route is short, production cost is low, labor intensity is low, environmental pollution is small, while lenticular product can be directly obtained, product quality fully meets user's requirement.
Description
Technical field
The invention belongs to 4,4 '-diamino hexichol of technical field of fine more particularly to a kind of Fine Organic Chemical product
The synthetic method of ether.
Background technique
4,4'- diaminodiphenyl ether be new special engineering plastics polyimides, polyetherimide, polyesterimide,
One of important source materials of fire resistant resins such as poly maleimide, Nomex.It still synthesizes 3,3', 4,4'- tetraminos two
The raw material of phenylate, the latter are a series of principal monomers for preparing heteroaromatic heat-proof macromolecule materials.It also serves as high performance heat resistant
Property the high molecular raw material of the synthesis such as epoxy resin, polyurethane and crosslinking agent.It is also used to substitute the biphenyl with carcinogenesis simultaneously
Amine produces the fields such as azo dyes, reactive dye and fragrance.
It is that raw material adds hydrogen to obtain 4,4'- bis- that the production technology that the country is widely used at present, which is with 4,4 '-dinitro diphenyl ethers,
Amino-diphenylethers.Big body technology is as follows: 4,4'- dinitro diphenyl ethers make catalyst with palladium carbon in a solvent, hydrogenation reaction of pressurizeing
4,4'- diaminodiphenyl ether is obtained, through crystallisation by cooling, crude product 4,4'- diaminodiphenyl ether is obtained by filtration；Then, crude product 4,4'-
Diaminodiphenyl ether distils at 200 DEG C or more of temperature and high vacuum, obtains block-like product.Bulk product can be made
For low-end product direct marketing, the high-end product of lenticular can also be recrystallized to give with solvent again.
This technique has the disadvantage that:
1. obtained product be it is blocky, this bulk product uniformity is inconsistent, can only make low-end product sale, but high-end user
Especially Foreign User is required of lenticular product, in order to obtain lenticular product, and 4,4'- of bulk diaminodiphenyl ether is also
It needs to be recrystallized with solvent, process is long, increases production cost.
2. sublimation purification process large labor intensity, production environment are poor.
3. sublimation purification requires to carry out under high temperature high vacuum, technique requires relatively high；Because of 4,4'- in sublimation process
Diaminodiphenyl ether oxidation, causes product yield to reduce, and generate the black residue of 5-10%, this residue can only make solid dangerous waste
Processing, increases three-protection design cost.
Summary of the invention
The purpose of the present invention is providing for existing defect, a kind of process route is short, production cost is low, labour is strong
Spend that low, environmental pollution is small and 4,4 ' diaminodiphenyl ether synthesis technologies of product yield, purity is high.
The principle of the present invention is: the crude product 4,4'- diaminodiphenyl ether obtained relative to prior art needs sublimation purification
The problem of, this technique uses mixed solvent crystallization method: using the solvent that solubility is good when hydrogenation reaction, when crystallization, is gradually added molten
The solvent of solution degree difference, reduces the solubility of product, while reducing temperature, and the rate of solvent, and control cooling are added by control
Product crystal is precipitated in rate.By filtering, being dried to obtain product after the completion of crystallization.The product does not need sublimation purification again, matter
Amount fully meets user's requirement, and product is lenticular, does not need to recrystallize.
Based on the above principles, technical scheme is as follows:
A kind of technique synthesizing 4,4 ' diaminodiphenyl ethers, includes the following steps:
(1) dissolve: by 4,4'- dinitro diphenyl ether, mixed solvent investment dissolution kettle, heating stirring is made it completely dissolved, so
Impurity is filtered out by filter afterwards, filtered lysate, which enters, to be added in hydrogen kettle；The mixed solvent is by dimethylformamide, first
Benzene mixes, and according to mass ratio meter 4,4'- dinitro diphenyl ether: dimethylformamide: toluene=1:(1.4-1.5):
(1.2-1.3)；
(2) add hydrogen: palladium catalyst charcoal is added in hydrogen kettle, heating up and being passed through hydrogen carries out hydrogenation reaction, thoroughly complete wait react
Cheng Hou, Filtration of catalyst, filtered reaction solution enter in crystallization kettle while hot；
(3) crystallize: the material in crystallization kettle, which is first warming up to 80-83 DEG C, makes its Quan Rong, then slow cooling, and simultaneously to crystallization
It is continuously added into water in kettle, stops adding water when temperature is down to 45-50 DEG C, according to mass ratio meter, the additional amount of the water is 4,
1.3-1.5 times of 4'- dinitro diphenyl ether；It then proceedes to make product be fully crystallized precipitation material cooling down；
(4) dry: to be centrifugally separating to obtain wet product with centrifuge, then be dried to obtain 4,4'- diaminodiphenyl ether product.
Further, the temperature dissolved by heating in the step (1) is 60-75 DEG C；According to mass ratio in the step (1)
Count 4,4'- dinitro diphenyl ether: dimethylformamide: toluene=1:1.42:1.24.
Further, palladium mass content is 5% in palladium charcoal in the step (2), according to mass ratio meter, additional amount 4,
The 0.3% of 4'- dinitro diphenyl ether.
Further, the catalyst recycling being filtered to remove in the step (2) re-uses, and adding in next batch
Hydrogen using when fill into the 4% of first usage amount.
Further, step (2) hydrogenation reaction controls pressure 0.7-0.9MPa, 65-75 DEG C of temperature, and reacts to hydrogen
Pressure keeps temperature, pressure 1 hour after no longer declining.
Further, the slow cooling in the step (3) controls as follows: being down to 68-72 DEG C by 80-83 DEG C
It is 130-150 minutes time-consuming；50-55 DEG C of time-consuming is down to 130-150 minutes by 68-72 DEG C；34-38 DEG C of time-consuming is down to by 50-55 DEG C
130-150 minutes.More into it is further preferred that the slow cooling in the step (3) controls as follows: being dropped by 83 DEG C
To 70 DEG C time-consuming 140 minutes；53 DEG C of time-consumings are down to 140 minutes by 70 DEG C；36 DEG C of time-consumings are down to 140 minutes by 53 DEG C.
Further, the additional amount of step (3) water is 1.4 times of 4,4'- dinitro diphenyl ether quality, and control adds
Water speed is 3~4 kg/minutes, guarantees that crystallization kettle temperature is down to 45~50 DEG C of this section Shi Jiashui and is finished.
Further, the end temperature that cooling down crystallizes in the step (3) is lower than 20 DEG C.
Further, dry using vacuum drying in the step (4), and control 70-80 DEG C of vacuum drying temperature, vacuum
Drying time 3 hours.
Compared with the prior art, the present invention does not need the process of sublimation purification again and recrystallization, short with process route,
The advantage that production cost is low, labor intensity is low, environmental pollution is small, while lenticular product can be directly obtained, product quality is complete
Full up foot user requires.
Specific embodiment
Below by embodiment the present invention is described in detail, it should be understood that these embodiments are only used for the purpose of illustration,
It is never limited in protection scope of the present invention.It will be understood by those skilled in the art that without departing from spirit and model of the invention
Can be with the details and forms of the technical scheme of the invention are modified or replaced under enclosing, but these modifications or substitutions each fall within this hair
In bright protection scope.
Embodiment 1
A kind of technique synthesizing 4,4 ' diaminodiphenyl ethers, includes the following steps:
1. dissolution:
1200 kilograms of DMF are first added in dissolution kettle, is then added 840 kilograms of 4,4'- dinitro diphenyl ether (based on sterling),
Add 1040 kilograms of toluene.After feeding intake, stirring is heated to 60~75 DEG C, and kept for half an hour or more, guarantees that material is complete
It dissolves in portion.Then dissolved material is squeezed into filter with pump, the impurity in material is filtered out by filter, filtered material
Into adding hydrogen kettle.
2. adding hydrogen:
(5%) 2.5 kilogram of palladium carbon catalyst is added in hydrogen kettle toward adding, closed plus hydrogen kettle is passed through nitrogen pressure testing, guarantees to add hydrogen kettle gas
Close property is well air tight.It is re-filled with nitrogen displacement, continuous displacement ensures that the oxygen in kettle is replaced completely three times.Starting stirring,
Opening collet heating makes material heat up, and hydrogen is passed through into kettle, starts hydrogenation reaction.65~75 DEG C of reaction temperature of control, pressure
0.7~0.9MPa.Often observation plus hydrogen speed illustrate that reaction is basically completed, react when hydrogen pressure no longer declines in reaction process
After the completion there is still a need for temperature, pressure 1 hour is kept, carry out reaction complete.After reaction, hydrogen in net kettle is put, nitrogen is used
Remaining hydrogen displacement is clean.Then material is squeezed into filter with pump while hot, filters off catalyst, filtered material enters knot
Brilliant kettle.It can be recycled for multiple times after catalyst is washed.
3. crystallization
Material after adding hydrogen is first passed through hot water in the collet of crystallization kettle before entering crystallization kettle, makes to crystallize autoclave body holding one
Fixed temperature, 80~82 DEG C of the hot water temperature being passed through, and it is with nitrogen that the air displacement in crystallization kettle is clean.Material after adding hydrogen
Into after crystallization kettle, the hot water temperature of crystallization kettle collet is controlled at 85~90 DEG C, crystallization kettle is heated, when material in kettle
When temperature reaches 80~83 DEG C, adjustment collet hot water temperature is 83~85 DEG C, keeps this temperature 1 hour.
The temperature fall off rate of material in kettle is controlled thereafter through the method for control crystallization kettle collet hot water temperature: by 83
DEG C it is down to 70 DEG C of time-consumings 140 minutes；53 DEG C of time-consumings are down to 140 minutes by 70 DEG C；36 DEG C of time-consumings are down to 140 minutes by 53 DEG C,
While starting cooling, 1180 kg of water are squeezed into crystallization kettle with metering pump, control plus water speed are 3~4 kg/minutes,
It asks when crystallization kettle temperature is down in 45~50 DEG C of this sections, water is added to finish.The directly cooling knot of cooling water is passed through in collet
Brilliant kettle after temperature is down to 36 DEG C, then uses chilled brine instead, and crystallization temperature in the kettle is made to be down to 20 DEG C hereinafter, then passing through centrifuge
The crystalline product of 20 ~ 80 mesh is obtained by filtration.
4. filtering, drying
It is filtered with centrifuge, obtained crystal is dry using double conic rotary vacuum dryer.It is passed through hot water in drier collet, controls
70-80 DEG C of temperature in drier processed is dried 3 hours at this temperature.Then it discharges after material in drier being cooled to room temperature,
Obtain product.
It is analyzed through HPLC, product purity 99.8%, yield 92.2%.
Embodiment 2
A kind of technique synthesizing 4,4 ' diaminodiphenyl ethers, includes the following steps:
1. dissolution:
1180 kilograms of DMF are first added in dissolution kettle, is then added 840 kilograms of 4,4'- dinitro diphenyl ether (based on sterling),
Add 1080 kilograms of toluene.After feeding intake, stirring is heated to 60~75 DEG C, and kept for half an hour or more, guarantees that material is complete
It dissolves in portion.Then dissolved material is squeezed into filter with pump, the impurity in material is filtered out by filter, filtered material
Into adding hydrogen kettle.
2. adding hydrogen:
(5%) 2.5 kilogram of palladium carbon catalyst is added in hydrogen kettle toward adding, closed plus hydrogen kettle is passed through nitrogen pressure testing, guarantees to add hydrogen kettle gas
Close property is well air tight.It is re-filled with nitrogen displacement, continuous displacement ensures that the oxygen in kettle is replaced completely three times.Starting stirring,
Opening collet heating makes material heat up, and hydrogen is passed through into kettle, starts hydrogenation reaction.65~75 DEG C of reaction temperature of control, pressure
0.7~0.9MPa.Often observation plus hydrogen speed illustrate that reaction is basically completed, react when hydrogen pressure no longer declines in reaction process
After the completion there is still a need for temperature, pressure 1 hour is kept, carry out reaction complete.After reaction, hydrogen in net kettle is put, nitrogen is used
Remaining hydrogen displacement is clean.Then material is squeezed into filter with pump while hot, filters off catalyst, filtered material enters knot
Brilliant kettle.It can be recycled for multiple times after catalyst is washed.
3. crystallization
Material after adding hydrogen is first passed through hot water in the collet of crystallization kettle before entering crystallization kettle, makes to crystallize autoclave body holding one
Fixed temperature, 80~82 DEG C of the hot water temperature being passed through, and it is with nitrogen that the air displacement in crystallization kettle is clean.Material after adding hydrogen
Into after crystallization kettle, the hot water temperature of crystallization kettle collet is controlled at 85~90 DEG C, crystallization kettle is heated, when material in kettle
When temperature reaches 80~83 DEG C, adjustment collet hot water temperature is 83~85 DEG C, keeps this temperature 1 hour.
The temperature fall off rate of material in kettle is controlled thereafter through the method for control crystallization kettle collet hot water temperature: by 83
DEG C it is down to 68 DEG C of time-consumings 150 minutes；50 DEG C of time-consumings are down to 130 minutes by 68 DEG C；38 DEG C of time-consumings are down to 145 minutes by 50 DEG C,
While starting cooling, 1100 kg of water are squeezed into crystallization kettle with metering pump, control plus water speed are 3~4 kg/minutes,
It asks when crystallization kettle temperature is down in 45~50 DEG C of this sections, water is added to finish.The directly cooling knot of cooling water is passed through in collet
Brilliant kettle after temperature is down to 38 DEG C, then uses chilled brine instead, and crystallization temperature in the kettle is made to be down to 20 DEG C hereinafter, then passing through centrifuge
The crystalline product of 20 ~ 80 mesh is obtained by filtration.
4. filtering, drying
It is filtered with centrifuge, obtained crystal is dry using double conic rotary vacuum dryer.It is passed through hot water in drier collet, controls
70-80 DEG C of temperature in drier processed is dried 3 hours at this temperature.Then it discharges after material in drier being cooled to room temperature,
Obtain product.
It is analyzed through HPLC, product purity 99.4%, yield 91.5%.
Embodiment 3
A kind of technique synthesizing 4,4 ' diaminodiphenyl ethers, includes the following steps:
1. dissolution:
1250 kilograms of DMF are first added in dissolution kettle, is then added 840 kilograms of 4,4'- dinitro diphenyl ether (based on sterling),
Add 990 kilograms of toluene.After feeding intake, stirring is heated to 60~75 DEG C, and kept for half an hour or more, guarantees that material is complete
It dissolves in portion.Then dissolved material is squeezed into filter with pump, the impurity in material is filtered out by filter, filtered material
Into adding hydrogen kettle.
2. adding hydrogen:
(5%) 2.5 kilogram of palladium carbon catalyst is added in hydrogen kettle toward adding, closed plus hydrogen kettle is passed through nitrogen pressure testing, guarantees to add hydrogen kettle gas
Close property is well air tight.It is re-filled with nitrogen displacement, continuous displacement ensures that the oxygen in kettle is replaced completely three times.Starting stirring,
Opening collet heating makes material heat up, and hydrogen is passed through into kettle, starts hydrogenation reaction.65~75 DEG C of reaction temperature of control, pressure
0.7~0.9MPa.Often observation plus hydrogen speed illustrate that reaction is basically completed, react when hydrogen pressure no longer declines in reaction process
After the completion there is still a need for temperature, pressure 1 hour is kept, carry out reaction complete.After reaction, hydrogen in net kettle is put, nitrogen is used
Remaining hydrogen displacement is clean.Then material is squeezed into filter with pump while hot, filters off catalyst, filtered material enters knot
Brilliant kettle.It can be recycled for multiple times after catalyst is washed.
3. crystallization
Material after adding hydrogen is first passed through hot water in the collet of crystallization kettle before entering crystallization kettle, makes to crystallize autoclave body holding one
Fixed temperature, 80~82 DEG C of the hot water temperature being passed through, and it is with nitrogen that the air displacement in crystallization kettle is clean.Material after adding hydrogen
Into after crystallization kettle, the hot water temperature of crystallization kettle collet is controlled at 85~90 DEG C, crystallization kettle is heated, when material in kettle
When temperature reaches 80~83 DEG C, adjustment collet hot water temperature is 83~85 DEG C, keeps this temperature 1 hour.
The temperature fall off rate of material in kettle is controlled thereafter through the method for control crystallization kettle collet hot water temperature: by 83
DEG C it is down to 72 DEG C of time-consumings 135 minutes；55 DEG C of time-consumings are down to 145 minutes by 72 DEG C；34 DEG C of time-consumings are down to 150 minutes by 55 DEG C,
While starting cooling, 1250 kg of water are squeezed into crystallization kettle with metering pump, control plus water speed are 3~4 kg/minutes,
It asks when crystallization kettle temperature is down in 45~50 DEG C of this sections, water is added to finish.The directly cooling knot of cooling water is passed through in collet
Brilliant kettle after temperature is down to 34 DEG C, then uses chilled brine instead, and crystallization temperature in the kettle is made to be down to 20 DEG C hereinafter, then passing through centrifuge
The crystalline product of 20 ~ 80 mesh is obtained by filtration.
4. filtering, drying
It is filtered with centrifuge, obtained crystal is dry using double conic rotary vacuum dryer.It is passed through hot water in drier collet, controls
70-80 DEG C of temperature in drier processed is dried 3 hours at this temperature.Then it discharges after material in drier being cooled to room temperature,
Obtain product.
It is analyzed through HPLC, product purity 99.3%, yield 91.8%.
Embodiment 1-3 can obtain the white crystal that product appearance is grayish, wherein being comprehensively compared, embodiment 1
Technical indicator it is best, therefore be optimal embodiment；Furthermore above-described embodiment be merely illustrative of the technical solution of the present invention and
Other modifications or equivalent replacement unrestricted, that those of ordinary skill in the art make technical solution of the present invention, as long as not
The spirit and scope of technical solution of the present invention are detached from, are intended to be within the scope of the claims of the invention.
Claims (10)
1. a kind of technique for synthesizing 4,4 ' diaminodiphenyl ethers, which comprises the steps of:
(1) dissolve: by 4,4'- dinitro diphenyl ether, mixed solvent investment dissolution kettle, heating stirring is made it completely dissolved, so
Impurity is filtered out by filter afterwards, filtered lysate, which enters, to be added in hydrogen kettle；The mixed solvent is by dimethylformamide, first
Benzene mixes, and according to mass ratio meter 4,4'- dinitro diphenyl ether: dimethylformamide: toluene=1:(1.4-1.5):
(1.2-1.3)；
(2) add hydrogen: palladium catalyst charcoal is added in hydrogen kettle, heating up and being passed through hydrogen carries out hydrogenation reaction, thoroughly complete wait react
Cheng Hou, Filtration of catalyst, filtered reaction solution enter in crystallization kettle while hot；
(3) crystallize: the material in crystallization kettle, which is first warming up to 80-83 DEG C, makes its Quan Rong, then slow cooling, and simultaneously to crystallization
It is continuously added into water in kettle, stops adding water when temperature is down to 45-50 DEG C, according to mass ratio meter, the additional amount of the water is 4,
1.3-1.5 times of 4'- dinitro diphenyl ether；It then proceedes to make product be fully crystallized precipitation material cooling down；
(4) dry: to be centrifugally separating to obtain wet product with centrifuge, then be dried to obtain 4,4'- diaminodiphenyl ether product.
2. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that in the step (1)
The temperature of heating for dissolving is 60-75 DEG C；According to mass ratio meter 4,4'- dinitro diphenyl ether in the step (1): dimethyl formyl
Amine: toluene=1:1.42:1.24.
3. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that in the step (2)
Palladium mass content is 5% in palladium charcoal, according to mass ratio meter, additional amount 4, and the 0.3% of 4'- dinitro diphenyl ether.
4. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1 or 3, which is characterized in that the step
(2) in be filtered to remove catalyst recycling re-use, and next batch plus hydrogen using when fill into first usage amount
4%。
5. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that the step (2) adds
Hydrogen reaction controlling pressure 0.7-0.9MPa, 65-75 DEG C of temperature, and reaction no longer decline to hydrogen pressure after holding temperature, pressure 1 it is small
When.
6. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that in the step (3)
Slow cooling control as follows: be down to 68-72 DEG C of time-consuming 130-150 minutes by 80-83 DEG C；It is down to by 68-72 DEG C
50-55 DEG C time-consuming 130-150 minutes；34-38 DEG C of time-consuming is down to 130-150 minutes by 50-55 DEG C.
7. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 5, which is characterized in that in the step (3)
Slow cooling control as follows: be down to 70 DEG C of time-consumings 140 minutes by 83 DEG C；53 DEG C of time-consumings 140 are down to by 70 DEG C to divide
Clock；36 DEG C of time-consumings are down to 140 minutes by 53 DEG C.
8. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that step (3) water
Additional amount be 1.4 times of 4,4'- dinitro diphenyl ether quality；Control plus water speed are 3~4 kg/minutes, guarantee crystallization
Kettle temperature degree is down to 45~50 DEG C of this section Shi Jiashui and is finished.
9. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that in the step (3)
The end temperature of cooling down crystallization is lower than 20 DEG C.
10. the technique of 4,4 ' diaminodiphenyl ethers of synthesis according to claim 1, which is characterized in that the step (4)
It is middle dry using vacuum drying, and control 70-80 DEG C of vacuum drying temperature, vacuum drying time 3 hours.
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| CN111233678A (en) * | 2020-03-26 | 2020-06-05 | 阮楚君 | Improved method for preparing diphenyl ether derivative by micro-channel process |
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| WO2023098203A1 (en) * | 2021-12-04 | 2023-06-08 | 青岛科技大学 | Production method for 4,4'-diaminodiphenyl ether |
| CN114591178A (en) * | 2022-03-17 | 2022-06-07 | 宁夏德昊科技产业有限公司 | ODA production process and production system |
| CN114591178B (en) * | 2022-03-17 | 2023-08-29 | 宁夏德昊科技产业有限公司 | ODA production process and production system |
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