CN104447523B - Method for synthesizing aminopyridine with pyridine base mixture as well as separation and purification method of aminopyridine - Google Patents
Method for synthesizing aminopyridine with pyridine base mixture as well as separation and purification method of aminopyridine Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention discloses a method for synthesizing aminopyridine with a pyridine base mixture as well as a separation and purification method of the aminopyridine and belongs to the field of fine chemical engineering. According to the method, the pyridine base mixture reacts with sodium amide under proper conditions, then a mixture of 2-amino-4-methylpyridine, 2-aminopyridine and 2-amino-6-methylpyridine is obtained through a hydrolysis reaction, the 2-amino-4-methylpyridine, the 2-aminopyridine and the 2-amino-6-methylpyridine are separated one by one according to different melting points and different boiling points of all the components in the mixture, and the high-purity 2-amino-4-methylpyridine, the high-purity 2-aminopyridine and the high-purity 2-amino-6-methylpyridine are obtained. The synthesizing method and the separation and purification method have the advantages of simple technology, reasonable design, convenience in operation, and the synthesizing method is an environment-friendly synthesizing technology and has the broad application prospect.
Description
Technical field
The invention belongs to field of fine chemical, specifically, it is related to a kind of synthetic method of chemical intermediate, more specifically
Say, be related to a kind of method and its isolation and purification method by pyridine base mixture synthesizing amino pyridine.
Background technology
Pyridine compounds and their is one of development and application kind widest in area in current heterocyclic compound, important as one kind
Fine chemical material, its derivative mainly has alkyl pyridine, haloperidid, aminopyridine, bromopyridine, picoline, iodine pyrrole
Pyridine, chloropyridine, nitropyridine, pyridone, benzyl pyridine, ethylpyridine, cyanopyridine, fluorine pyridine, dihydropyridine etc., wherein
Agricultural chemicals accounts for 50% or so of pyridine series product consumption total amount, and feed addictive is about 30%, and medicine and other field account for 20%.
Pyridine bases compound is the important source material of organic synthesis industry, medical industry, rubber industry and agricultural chemical industry, is produced
The larger pyridine base of amount mainly includes：Pyridine, 2- picolines, 3- picolines, 4- picolines, 2- methyl -5- ethyl pyrroles
Pyridine.
Pyridine is that, containing a 6-membered heterocyclic compound for nitrogen heteroatom, its boiling point is 115.3 DEG C, and fusing point is -41.6 DEG C,
It is used to synthesize PA in medical industry, as manufacture herbicide and the raw material of insecticide in pesticide industry, in weaving
It is used to manufacture waterproofing agent and surfactant in dyestuff.2- picolines are industrially mainly used for as manufacture butadiene-vinylpyridine copylymer latex
Raw material.4- picolines are mainly used in producing rimifon in pharmaceuticals industry, and 2- picolines have similar property.Due to day
Right pyridine alkali content is low, complicated component, separating-purifying are relatively difficult and the reason such as is limited by the utilization of resources, and much meets not
The development need of industrial or agricultural each side, thus the production of pyridine base is set up with coal tar and acetaldehyde, acetylene etc. as raw material
Mixed type pyridine base production system.Under the conditions of normal pressure and 350-500 DEG C, the gas-phase dehydration of acetaldehyde (para-acetaldehyde) and ammonia,
Deamination and the catalytic reaction of cyclization, its major product are 2- picolines, 4- picolines and other pyridine alkali cpds
Mixture.Through retrieval, the A of Chinese Patent Application No. CN 1506353, the applying date is that the patent of invention on December 11 in 2002 is disclosed
A kind of preparation method of pyridine and picoline, the invention under gas phase, with ammonia, formaldehyde and acetaldehyde as raw material, with siliconized
Compound or germanium compound and its modified molecular sieve of mixture organic solution are catalyst pyridine synthesis and picoline, are solved
There is product pyridine in conventional art when molecular sieve catalytic ammonia, carbonyls and the selectivity and yield of picoline are relatively low
Problem.The A of Chinese Patent Application No. CN 1886195, the applying date is that the patent of invention on December 31 in 2003 discloses synthesis 2-
The catalyst of picoline and 4- picolines and the method for preparing 2- picolines and 4- picolines and catalyst, the hair
Catalyst in bright is included in the heteropoly acid on the carriers such as silica gel, aluminum oxide, and the invention prepares 2- picolines and 4- methyl pyrroles
The method of pyridine is in the presence of a catalyst, heating obtains acetaldehyde and ammonia reaction.But the pyridine and picoline for obtaining are
Exist as a mixture, often there is the mixture of 2- picolines, pyridine and 4- picolines, wherein 2- methyl in the market
Pyridine content be 90% or so, pyridine content be 6% or so, 4- picoline contents be 4% or so, due to 2- picolines,
Closely, therefore such component is difficult separating-purifying to the property of pyridine and 4- picolines, and its application is restricted, it is impossible to
The requirement of pharmaceuticals industry and agricultural to intermediate purity is met, in order to make full use of this kind of mixture, it is necessary to study a kind of separation
The method of purifying 2- picolines, pyridine and 4- methyl pyridine mixtures, makes its each component to be effectively utilized.
The content of the invention
1. the problem to be solved
For the problem that 2- picolines present in prior art, pyridine and 4- methyl pyridine mixtures are difficult separate,
The present invention provides a kind of method and its isolation and purification method by pyridine base mixture synthesizing amino pyridine, by pyridine base mixture
Under suitable conditions with Sodamide react, the reaction that is then hydrolyzed obtain 2-AMINO-4-PICOLINE, PA and
The mixture of 2- amino -6- picolines, the fusing point according to each component in mixture is different with boiling point, by 2- amino -4- first
Yl pyridines, PA and 2- amino -6- picolines separate the 2- amino -4- methyl pyrroles for obtaining high-purity one by one
Pyridine, PA and 2- amino -6- picolines.
2. technical scheme
In order to solve the above problems, the technical solution adopted in the present invention is as follows：
A kind of method by pyridine base mixture synthesizing amino pyridine, its step is：
A () adds dimethylbenzene in reaction bulb, stirred during pyridine base mixture then is added into reaction bulb by constant pressure funnel
Mix uniform, wherein dimethylbenzene and the mass ratio of pyridine base mixture is (2-3):1；
B reaction bulb in step (a) is heated to 80-135 DEG C and carries out reflux dewatering reaction by ()；
C the dehydration in () step (b) is cooled to room temperature after terminating, stirring is equal during Sodamide is added into reaction bulb
It is even, micro- back flow reaction is then carried out, wherein Sodamide and the mass ratio of pyridine base mixture is 1:(1-1.5)；
D the micro- back flow reaction in () step (c) terminates after, enter in water droplet is added into reaction bulb under conditions of being stirred continuously
Row hydrolysis, its reclaimed water is 1 with the mass ratio of pyridine base mixture:(2-3)；
E the hydrolysis in () step (d) terminates after, stopping is stirred and stood, and water phase is layered with dimethylbenzene, obtains amino
Pyridine mixtures are dissolved in organic phase.
Preferably, described pyridine base mixture is the mixture being made up of 2- picolines, pyridine and 4- picolines.
Preferably, iron ion and water are not contained in dimethylbenzene in described step (a).
Preferably, the addition speed of Sodamide is 10-20g/min in described step (c).
Preferably, the rate of addition of described step (d) reclaimed water is 7-14g/min, and hydrolysis time is 0.5-1h.
A kind of above-mentioned isolation and purification method by pyridine base mixture synthesizing amino pyridine, its step is：
(1) by the water phase in above-mentioned steps (e) and the organic phase separation of dimethylbenzene, the organic phase that will be obtained first is concentrated into originally
The 1/3-2/3 of volume, is subsequently cooled to 93-99 DEG C and is incubated 2-3h, has solid to separate out；
(2) solidliquid mixture in step (1) is separated by filtration, the solid for obtaining is 2-AMINO-4-PICOLINE, will be filtered
Liquid is cooled to 57-63 DEG C and is incubated 2-3h, has solid to separate out；
(3) solidliquid mixture in step (2) is separated by filtration, the solid for obtaining is PA, and filtrate is lowered the temperature
To 18-23 DEG C and 2-3h is incubated, there is solid to separate out；
(4) solidliquid mixture in step (3) is separated by filtration, the solid for obtaining is 2- amino -6- picolines, is collected
Filtrate；
(5) by the filtrate Distillation recovery dimethylbenzene in step (4).
Preferably, the organic phase that will be obtained in described step (1) is cooled to 98 DEG C and is incubated 2h.
Preferably, 62 DEG C are cooled the filtrate in described step (2) and is incubated 2h.
3. beneficial effect
Compared to prior art, beneficial effects of the present invention are：
(1) a kind of method by pyridine base mixture synthesizing amino pyridine of the invention, can make full use of by 2- methyl pyrroles
The pyridine base mixture of pyridine, pyridine and 4- picolines composition, isolates and purifies by aminating reaction, hydrolysis and suitably
To the monomer of the 2- amino -6- picolines, PA and 2-AMINO-4-PICOLINE of high-purity, medicine conjunction can be met
Requirement into field to intermediate purity；
(2) a kind of method by pyridine base mixture synthesizing amino pyridine of the invention, can in the market as useless
Chemical intermediate that the pyridine base mixture of solvent treatment reacts generation high-purity under mild conditions, having economic worth is former
Material, turns waste into wealth, it is to avoid environmental pollution；
(3) a kind of method by pyridine base mixture synthesizing amino pyridine of the invention, is first mixed pyridine base with dimethylbenzene
Compound carries out dehydration, to ensure the yield and conversion ratio of follow-up aminating reaction, by the dropwise addition speed for controlling Sodamide and water
Degree so that it is more thorough that aminating reaction and hydrolysis are carried out, the equal energy of purity of reaction yield and the aminopyridine products for obtaining
It is a kind of synthesis technique of environmental protection higher than 99%, low cost, income is high, has broad application prospects；
(4) a kind of isolation and purification method by pyridine base mixture synthesizing amino pyridine in the present invention, according to product
The physical properties such as fusing point, boiling point are different, with reference to their growth characteristics, the method for using cooling separate, by three kinds of products according to
Secondary to separate, process is simple is reasonable in design, easy to operate, isolated 2- amino -6- picolines, PA
99% is above with the monomer purity of 2-AMINO-4-PICOLINE, and quality is not different compared with commercially available single raw material.
Brief description of the drawings
Fig. 1 is the schematic flow sheet of synthetic method of the present invention；
Fig. 2 is the structural representation of 6 kinds of materials of the invention.
In figure：1st, 2- picolines；2nd, pyridine；3rd, 4- picolines；4th, 2- amino -6- picolines；5th, 2- amino pyrrole
Pyridine；6th, 2-AMINO-4-PICOLINE.
Specific embodiment
The present invention is further described below with reference to specific embodiment.
Embodiment 1
As shown in figure 1, a kind of method by pyridine base mixture synthesizing amino pyridine, its step is：
A () adds dimethylbenzene (without iron ion and water) in reaction bulb, then will be by 2- picolines, pyridine and 4- first
The pyridine base mixture of yl pyridines composition is stirred in adding reaction bulb by constant pressure funnel, and wherein dimethylbenzene is mixed with pyridine base
The mass ratio of compound is 2.5:1, it is 6%, 4- picolines that 2- picolines account for gross mass 90%, pyridine in pyridine base mixture
4%；
B reaction bulb in step (a) is slowly heated to 80 DEG C and carries out reflux dewatering reaction until anhydrous in reaction bulb by ()
Drop is produced；
C the dehydration in () step (b) is cooled to room temperature after terminating, by Sodamide add (add speed be
10g/min) to enter stir in reaction bulb, then carry out micro- back flow reaction, wherein the quality of Sodamide and pyridine base mixture
Than being 1:1.13；
Water droplet d the micro- back flow reaction in () step (c) terminates after, adds (rate of addition is under conditions of being stirred continuously
7g/min) enter and be hydrolyzed in reaction bulb reaction, hydrolysis time is 1h, and its reclaimed water is with the mass ratio of pyridine base mixture
1:2.3；
E the hydrolysis in () step (d) terminates after, stopping is stirred and stood, and water phase is layered with dimethylbenzene, obtains amino
Pyridine mixtures are dissolved in organic phase.
A kind of above-mentioned isolation and purification method by pyridine base mixture synthesizing amino pyridine, its step is：
(1) the water phase in above-mentioned steps (e) is separated with dimethylbenzene, the organic phase that will be obtained first is concentrated into original volume
1/3, dimethylbenzene is reclaimed, organic phase is then cooled to 98 DEG C and 2h is incubated, there is solid to separate out；
(2) solidliquid mixture in step (1) is separated by filtration, the solid for obtaining is 2-AMINO-4-PICOLINE, will be filtered
Liquid is cooled to 62 DEG C and is incubated 2h, has solid to separate out；
(3) solidliquid mixture in step (2) is separated by filtration, the solid for obtaining is PA, and filtrate is lowered the temperature
To 18 DEG C and 1h is incubated, there is solid to separate out；
(4) solidliquid mixture in step (3) is separated by filtration, the solid for obtaining is 2- amino -6- picolines, is collected
Filtrate；
(5) by the filtrate Distillation recovery dimethylbenzene in step (4).
The conversion ratio reacted in the present embodiment is 95%, three kinds of product 2-AMINO-4-PICOLINEs, the 2- amino pyrroles for obtaining
Pyridine and 2- amino -6- picolines, through gas chromatographic analysis, three kinds of purity of product are respectively 99%, 99.5% and 99%.
Embodiment 2
A kind of method by pyridine base mixture synthesizing amino pyridine, its step is：
A () adds dimethylbenzene (being free of iron ion) in reaction bulb, then will be by 2- picolines, pyridine and 4- methyl pyrroles
The pyridine base mixture of pyridine composition stirs in adding reaction bulb by constant pressure funnel, wherein dimethylbenzene and pyridine base mixture
Mass ratio be 2:1, it is 11%, 4- picolines 7% that 2- picolines account for gross mass 82%, pyridine in pyridine base mixture；
B reaction bulb in step (a) is slowly heated to 100 DEG C and carries out reflux dewatering reaction until anhydrous in reaction bulb by ()
Drop is produced；
C the dehydration in () step (b) is cooled to room temperature after terminating, Sodamide is added with the speed of 15g/min
To enter stir in reaction bulb, then carry out micro- back flow reaction, wherein Sodamide and the mass ratio of pyridine base mixture is 1:1；
Water droplet d the micro- back flow reaction in () step (c) terminates after, adds (rate of addition is under conditions of being stirred continuously
10g/min) enter and be hydrolyzed in reaction bulb reaction, hydrolysis time is 0.5h, the quality of its reclaimed water and pyridine base mixture
Than being 1:2；
E the hydrolysis in () step (d) terminates after, stopping is stirred and stood, and water phase is layered with dimethylbenzene, obtains amino
Pyridine mixtures are dissolved in organic phase.
A kind of above-mentioned isolation and purification method by pyridine base mixture synthesizing amino pyridine, its step is：
(1) the water phase in above-mentioned steps (e) is separated with dimethylbenzene, the organic phase that will be obtained first is concentrated into original volume
2/3, it is subsequently cooled to 93 DEG C and is incubated 1h, there is solid to separate out；
(2) solidliquid mixture in step (1) is separated by filtration, the solid for obtaining is 2-AMINO-4-PICOLINE, will be filtered
Liquid is cooled to 57 DEG C and is incubated 1h, has solid to separate out；
(3) solidliquid mixture in step (2) is separated by filtration, the solid for obtaining is PA, and filtrate is lowered the temperature
To 20 DEG C and 2h is incubated, there is solid to separate out；
(4) solidliquid mixture in step (3) is separated by filtration, the solid for obtaining is 2- amino -6- picolines, is collected
Filtrate；
(5) by the filtrate Distillation recovery dimethylbenzene in step (4).
The conversion ratio reacted in the present embodiment is 98%, three kinds of product 2-AMINO-4-PICOLINEs, the 2- amino pyrroles for obtaining
Pyridine and 2- amino -6- picolines, through gas chromatographic analysis, three kinds of purity of product are respectively 99.7%, 99.1% He
99.3%.
Embodiment 3
A kind of method by pyridine base mixture synthesizing amino pyridine, its step is：
A () adds dimethylbenzene (being free of iron ion) in reaction bulb, then will be by 2- picolines, pyridine and 4- methyl pyrroles
The pyridine base mixture of pyridine composition stirs in adding reaction bulb by constant pressure funnel, wherein dimethylbenzene and pyridine base mixture
Mass ratio be 3:1, it is 28%, 4- picolines 17% that 2- picolines account for gross mass 55%, pyridine in pyridine base mixture；
B reaction bulb in step (a) is slowly heated to 135 DEG C and carries out reflux dewatering reaction until anhydrous in reaction bulb by ()
Drop is produced；
C the dehydration in () step (b) is cooled to room temperature after terminating, Sodamide is added with the speed of 20g/min
To enter stir in reaction bulb, then carry out micro- back flow reaction, wherein Sodamide and the mass ratio of pyridine base mixture is 1:
1.5；
Water droplet d the micro- back flow reaction in () step (c) terminates after, adds (rate of addition is under conditions of being stirred continuously
14g/min) enter and be hydrolyzed in reaction bulb reaction, hydrolysis time is 0.8h, the quality of its reclaimed water and pyridine base mixture
Than being 1:3；
E the hydrolysis in () step (d) terminates after, stopping is stirred and stood, and water phase is layered with dimethylbenzene, obtains amino
Pyridine mixtures are dissolved in organic phase.
(1) the water phase in above-mentioned steps (e) is separated with dimethylbenzene, the organic phase that will be obtained first is concentrated into original volume
1/3, it is subsequently cooled to 99 DEG C and is incubated 3h, there is solid to separate out；
(2) solidliquid mixture in step (1) is separated by filtration, the solid for obtaining is 2-AMINO-4-PICOLINE, will be filtered
Liquid is cooled to 63 DEG C and is incubated 3h, has solid to separate out；
(3) solidliquid mixture in step (2) is separated by filtration, the solid for obtaining is PA, and filtrate is lowered the temperature
To 23 DEG C and 3h is incubated, there is solid to separate out；
(4) solidliquid mixture in step (3) is separated by filtration, the solid for obtaining is 2- amino -6- picolines, is collected
Filtrate；
(5) by the filtrate Distillation recovery dimethylbenzene in step (4).
The conversion ratio reacted in the present embodiment is 96%, three kinds of product 2-AMINO-4-PICOLINEs, the 2- amino pyrroles for obtaining
Pyridine and 2- amino -6- picolines, through gas chromatographic analysis, three kinds of purity of product are respectively 99.4%, 99.6% He
99.1%.
Claims (6)
1. a kind of method by pyridine base mixture synthesizing amino pyridine, described pyridine base mixture is useless for pyridine production
Material, is made up of 2- picolines, pyridine and 4- picolines, and its step is：
A () adds dimethylbenzene in reaction bulb, stirring is equal during pyridine base mixture then is added into reaction bulb by constant pressure funnel
Even, wherein dimethylbenzene and the mass ratio of pyridine base mixture is (2-3):1；
B reaction bulb in step (a) is heated to 80-135 DEG C and carries out reflux dewatering reaction by ()；
C the dehydration in () step (b) is cooled to room temperature after terminating, stirred during Sodamide is added into reaction bulb,
Then micro- back flow reaction is carried out, wherein Sodamide and the mass ratio of pyridine base mixture is 1:(1-1.5)；
D the micro- back flow reaction in () step (c) terminates after, water-filling is entered in water droplet is added into reaction bulb under conditions of being stirred continuously
Solution reaction, its reclaimed water is 1 with the mass ratio of pyridine base mixture:(2-3)；
E the hydrolysis in () step (d) terminates after, stopping is stirred and stood, and water phase is layered with dimethylbenzene, obtains aminopyridine
Mixture is dissolved in organic phase；
F water phase in step (e) and the organic phase separation of dimethylbenzene, the organic phase that will be obtained first are concentrated into the 1/ of original volume by ()
3-2/3, is subsequently cooled to 93-99 DEG C and is incubated 1-3h, has solid to separate out；
G be separated by filtration for solidliquid mixture in step (f) by (), the solid for obtaining is 2-AMINO-4-PICOLINE, and filtrate is dropped
Temperature is to 57-63 DEG C and is incubated 1-3h, has solid to separate out；
H be separated by filtration for solidliquid mixture in step (g) by (), the solid for obtaining is PA, cools the filtrate to 18-
23 DEG C and 1-3h is incubated, there is solid to separate out；
I be separated by filtration for solidliquid mixture in step (h) by (), the solid for obtaining is 2- amino -6- picolines, collects filter
Liquid；
J () is by the filtrate Distillation recovery dimethylbenzene in step (i).
2. a kind of method by pyridine base mixture synthesizing amino pyridine according to claim 1, it is characterised in that：It is described
The step of (a) in do not contain iron ion and water in dimethylbenzene.
3. a kind of method by pyridine base mixture synthesizing amino pyridine according to claim 1, it is characterised in that：It is described
The step of (c) in Sodamide addition speed be 10-20g/min.
4. a kind of method by pyridine base mixture synthesizing amino pyridine according to claim 1, it is characterised in that：It is described
The step of (d) reclaimed water rate of addition be 7-14g/min, hydrolysis time is 0.5-1h.
5. a kind of method by pyridine base mixture synthesizing amino pyridine according to claim 1, it is characterised in that：It is described
The step of (f) in the organic phase that will obtain be cooled to 98 DEG C and be incubated 2h.
6. a kind of method by pyridine base mixture synthesizing amino pyridine according to claim 1, it is characterised in that：It is described
The step of (g) in cool the filtrate to 62 DEG C and be incubated 2h.
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| WO1996018616A1 (en) * | 1994-12-12 | 1996-06-20 | Merck & Co., Inc. | Substituted 2-aminopyridines as inhibitors of nitric oxide synthase |
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