CN110372580A - A kind of separation method of 2- chloropyridine and 3- chloropyridine - Google Patents
A kind of separation method of 2- chloropyridine and 3- chloropyridine Download PDFInfo
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- CN110372580A CN110372580A CN201910536826.2A CN201910536826A CN110372580A CN 110372580 A CN110372580 A CN 110372580A CN 201910536826 A CN201910536826 A CN 201910536826A CN 110372580 A CN110372580 A CN 110372580A
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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 the separation methods of a kind of 2- chloropyridine and 3- chloropyridine, using the mixture of double two bromine oxethyls column [6] aromatic hydrocarbons crystalline material adsorbing separation 2- chloropyridines and 3- chloropyridine, the structural formula of described double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials is as follows:Separation process of the present invention is easy to operate, is not necessarily to complex device, good operation safety；Separation is not necessarily to distillation operation, energy saving, reduces production cost；Crystalline material stability used is high, can be recycled, separating effect will not reduce.
Description
Technical field
The present invention relates to adsorption separation technology fields, and in particular to a kind of separation method of 2- chloropyridine and 3- chloropyridine.
Background technique
2- chloropyridine is as a very important intermediate in industrial production, in the synthesis and dailyization of medicine, pesticide
The fields such as work are widely used, and are had a vast market foreground.In recent years, as 2- chloropyridine market application field constantly expands
Greatly, demand is also increasing, therefore in widespread attention.
Currently, industrially synthesis 2- chloropyridine mainly has three kinds of N- oxidizing process, light chlorination process, thermal chlorination methods, wherein
Thermal chlorination is widely applied because of the feature that synthetic route is short, yield is high.Pyridine high temperature direct chlorination, product with temperature and
Different, 170~270 DEG C, electrophilic attack occurs to generate 3- chloropyridine and 3,5- dichloropyridine in the position 3- of pyridine；270~300 DEG C,
Electrophilic attack and free radical attack occurs simultaneously, product is extremely complex；300~500 DEG C are free radical attack, and reaction occurs in 2-
Position, primary product are 2- chloropyridine (J.Am.Chem.Soc., 1950,72:4362-4364).Thermal chlorination reaction temperature be 260~
420 DEG C, therefore during synthesizing 2- chloropyridine, inevitably there are 3- chloropyridine and other polysubstituted chloropyridines to generate, after
Person can be removed since boiling point is higher by gas-liquid separation, but due to 3- chloropyridine (148 DEG C) and 2- chloropyridine (166 DEG C) boiling point
Close, the former is difficult to remove, and 2- chloropyridine purity is caused to be affected.How 2- chloropyridine and 3- chloropyridine be separated into 2-
The key link of chloropyridine purifying.
The Chinese patent literature of 101270079 A of Publication No. CN discloses in a kind of preparation of chloro-pyridine compounds
The separation method of gaseous mix products.It is reacted in the reactor for raw material with chlorinating agent by pyridine and chloro-pyridine class gas is prepared
State product is directly entered two rectification cells for including at least the setting that is linked in sequence in the presence of nitrogen and divides in rectification cell
Do not include the distillation system of rectifying still and rectifying column, realizes online rectification and purification.
The Chinese patent literature of 1245167 A of Publication No. CN discloses a kind of separation method of chloropyridine product, adopts
With first carrying out water-oil separating, then is neutralized, dechlorinated respectively, being flashed, the technique of rectifying.
Required temperature is high in above method distillation process, needs huge energy consumption, is unfavorable for China's green energy resource hair
Exhibition；And rectifying device maintenance cost is high, improves enterprise's production cost, reduces the economic benefit of enterprise.
In conclusion finding, one kind is novel can be efficiently separated 2- chloropyridine and 3- chloropyridine and the less energy is only needed to disappear
The method of consumption becomes the key of current industry 2- chloropyridine purifying.
Summary of the invention
For in industry purify 2- chloropyridine during high energy consumption, the device is complicated, operation risk factor is high the problems such as and
Shortcoming existing for this field, the present invention provides the separation method of a kind of 2- chloropyridine and 3- chloropyridine, use is non-porous
Adaptive double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials purify 2- chloropyridine.The material can be effectively from 2- chlorine pyrrole
Highly selective absorption 2- chloropyridine in pyridine and 3- chloropyridine mixture, low energy consumption, equilibration time is short, easy to operate.
A kind of separation method of 2- chloropyridine and 3- chloropyridine is inhaled using double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials
Mixture of the Fufen from 2- chloropyridine and 3- chloropyridine.
Since the difference of the position of substitution leads to the architectural difference of 2- chloropyridine and 3- chloropyridine, institute to chlorine atom on pyridine ring
The Subjective and Objective complexing that stoichiometric ratio is 1:2 can be formed with 2- chloropyridine by stating double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials
Object.Due to the weak interaction force that host-guest interaction power is non-covalent bond, cause the complex compound unstable, Subjective and Objective meeting when heating
Solution complexing, 2- chloropyridine are released.Described double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials are stable under desorption temperature
, it is reusable after the completion of desorption, and selective effect will not decline.
The structural formula of described double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials is as follows:
The preparation method of described double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials includes: by bis- bromo of 1,1- to benzene diethyl
Ether is added in 1,2- dichloroethane solvent, and lewis acid is added, reacts 20~30 minutes at 25~30 DEG C, uses carbon after reaction
Sour hydrogen sodium saturated solution is quenched, and obtains crude product, the isolated double dibromo ethoxies of crude by column chromatography after washing liquid separation concentration
Pilum [6] aromatic hydrocarbons.
Double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials after column chromatography for separation can it is dry by vacuum decompression,
110~130 DEG C of overnight modes remove solvent molecule, to be activated.Double two bromine oxethyl column [6] aromatic hydrocarbons crystal after activation
Material is used directly for the adsorbing separation of 2- chloropyridine and 3- chloropyridine.
The separation method of the 2- chloropyridine and 3- chloropyridine specifically: will double two bromine oxethyl column [6] aromatic hydrocarbons crystal
Material is placed in the mixed vapour atmosphere of 2- chloropyridine and 3- chloropyridine, and temperature is 20~30 DEG C, and adsorption time is according to 2- chlorine pyrrole
Depending on the time that pyridine reaches adsorption saturation.
In adsorption process, described double two bromine oxethyl column [6] aromatic hydrocarbons crystalline material cavitys are opened, and accommodate gas molecule,
To which the change of crystal form occur.Due to the multiple weak interaction of CH- π, pi-pi accumulation, 2- chloropyridine in mixed vapour can be with
Double two bromine oxethyls column [6] aromatic hydrocarbons form host-guest complex, and the stoichiometric ratio of the host-guest complex is 2:1.
The mode that normal heating or heating under reduced pressure can be used removes double two bromine oxethyl column [6] aromatic hydrocarbons crystalline material surfaces suctions
The mixture of attached 2- chloropyridine and 3- chloropyridine.
The temperature of the normal heating or heating under reduced pressure is 30~50 DEG C.Heating time can it is specific depending on.
The condition will not destroy Host guest complexation power, therefore the host-guest complex is still stabilized, and table
The chloropyridine mixture of face absorption then can be removed gradually.By removing the mixed vapour of adsorption, adsorbed to improve
The purity of 2- chloropyridine.
The 2- chlorine pyrrole of double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials absorption complexings is desorbed in the mode that heating in vacuum can be used
Pyridine molecule.
The temperature of the heating in vacuum is 110~130 DEG C.Heating time can it is specific depending on.
The condition destroys Host guest complexation power, and the 2- chloropyridine molecule being adsorbed can be released gradually, and double
Two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials be then it is stable, the change of crystal form only occurs during desorption.Desorption is completed
Double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials afterwards are then restored to the state for being initially activated completion, can continue on for inhaling
Fufen is recycled next time from 2- chloropyridine and 3- chloropyridine.Double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials pass through five times
Adsorption desorption circulation, significant change does not occur to the selectivity of 2- chloropyridine.
Compared with prior art, the present invention major advantage includes: that separation process is easy to operate, it is not necessarily to complex device, operation
Safety is good；Separation is not necessarily to distillation operation, energy saving, reduces production cost；Crystalline material stability used is high, can recycle
It uses, separating effect will not reduce.
Detailed description of the invention
Fig. 1 is the powder x-ray diffraction (PXRD) of double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials of Examples 1 to 4
Figure；
Fig. 2 is double two bromine oxethyl column [6] aromatic hydrocarbons crystalline material adsorbing separation 2- chloropyridines and 3- chloropyridine of embodiment 3
Gas-chromatography characterization result figure；
Fig. 3 is when double bromine diethoxy pilum [6] aromatic hydrocarbons crystalline materials of embodiment 5 are recycled to 2- chloropyridine and 3- chlorine
Pyridine adsorption separating effect selective figure.
Specific embodiment
With reference to the accompanying drawing and specific embodiment, the present invention is further explained.It should be understood that these embodiments are merely to illustrate
The present invention rather than limit the scope of the invention.The operating method of actual conditions is not specified in the following example, usually according to
Normal condition, or according to the normal condition proposed by manufacturer.
Embodiment 1
The preparation of double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials: double two are prepared to benzene diethyl ether using bis- bromo of 1,1-
Bromine oxethyl column [6] aromatic hydrocarbons.
1,1- bis- bromo is added to 100mL 1 to benzene diethyl ether (6.74g, 23.0mmol), in 2- dichloroethanes, is added
BF3·O(C2H5)2(23.0~23.5mmol), mixed liquor stir 20~30 minutes at 25 DEG C, use saturated sodium bicarbonate solution
It is quenched that reaction was completed, is washed twice with deionized water, organic phase is concentrated under reduced pressure to give crude product, and crude product rapid column chromatography is pure
Change (petroleum ether/methylene chloride volume ratio=1:2) obtains double two bromine oxethyl column [6] aromatic hydrocarbons, and (1.20g, yield are
It 16.9%), is white solid.The white solid is placed in 120 DEG C of vacuum drying oven overnight, double dibromo second after being activated
Oxygroup column [6] aromatic hydrocarbons crystalline material is white powder, is denoted as BrP6.
Product characterize data manufactured in the present embodiment is as follows:
BrP6,1H NMR(400MHz,CDCl3, 298K, ppm) and δ 6.78 (s, 12H), 4.16 (t, J=5.8Hz, 24H),
3.87 (s, 12H), 3.55 (t, J=5.8Hz, 24H).
PXRD testing result as shown in Figure 1, obtained double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials have it is good
Crystallinity.
Embodiment 2
Absorption of double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials to independent 2- chloropyridine or 3- chloropyridine: two are taken
20mL seed bottle is separately added into 2mL 2- chloropyridine and 2mL 3- chloropyridine, is named as BrP6@2-CP and BrP6@3-CP, respectively
Bis- two bromine oxethyls column [6] the aromatic hydrocarbons crystalline materials of 30mg are taken to be placed in two 5mL seed bottles, by two opening 5mL seed bottles
It is placed in two 20mL seed bottles, 20mL seed bottle is sealed, placed 48 hours at 25 DEG C of room temperature, by obtained powder 40
It is placed 30 minutes in DEG C baking oven.
Product characterize data manufactured in the present embodiment is as follows:
BrP6@2-CP,1H NMR (400MHz, CDCl3,298K, ppm) δ 8.42-8.39 (m, 2H), 7.66 (td, J=
7.7,2.0Hz, 2H), 7.34 (dt, J=8.1,0.9Hz, 2H), 7.23 (ddd, J=7.4,4.9,1.0Hz, 2H), 6.78 (s,
12H), 4.16 (t, J=5.8Hz, 24H), 3.87 (s, 12H), 3.55 (t, J=5.8Hz, 24H).
BrP6@3-CP,1H NMR(400MHz,CDCl3, 298K, ppm) and δ 8.59 (d, J=2.5Hz, 2H), 8.50 (d, J=
5.8Hz, 2H), 7.68 (d, J=10.6Hz, 2H), 6.78 (s, 12H), 4.16 (t, J=5.8Hz, 24H), 3.87 (s, 12H),
3.55 (t, J=5.8Hz, 24H).
1H NMR is the result shows that double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials can be the side of 1:2 with stoichiometric ratio
Formula adsorbs 2- chloropyridine and 3- chloropyridine.
PXRD testing result is as shown in Figure 1, relative to double two bromine oxethyl column [6] the aromatic hydrocarbons crystalline materials initially activated
PXRD spectrogram, double two bromine oxethyl column [6] aromatic hydrocarbons after placed a period of time in 2- chloropyridine or 3- chloropyridine steam are brilliant
There is variation in the PXRD spectrogram of body material, this shows that the cell parameter of material is changed, i.e. 2- chloropyridine or 3- chlorine
Pyridine can be adsorbed into double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials；But 2- chloropyridine or 3- chloropyridine are adsorbed
The PXRD spectrogram of double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials difference, this illustrates that material shows after adsorbing the two
Different microcosmic crystalline arrangement modes.
Embodiment 3
The 2- chloropyridine and 3- chloropyridine mixture that double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials are 1:1 to volume ratio
Absorption: take a 20mL seed bottle, 1mL 2- chloropyridine and 1mL 3- chloropyridine be added, is named as BrP6@2/3-CP, takes
Bis- diethoxy pilum [6] the aromatic hydrocarbons crystalline materials of 30mg are placed in 5mL seed bottle, and open 5mL seed bottle is placed in above-mentioned 20mL
In seed bottle, 20mL seed bottle is sealed, is placed 48 hours at 25 DEG C of room temperature, obtained powder is placed in 40 DEG C of baking ovens
30 minutes.
Product characterize data manufactured in the present embodiment is as follows:
BrP6@2/3-CP,1H NMR(400MHz,CDCl3, 298K, ppm) and δ 8.40 (dd, J=4.9,1.5Hz, 2H),
7.66 (td, J=7.9,2.0Hz, 2H), 7.34 (d, J=8.0Hz, 2H), 7.23 (ddd, J=7.4,4.9,0.9Hz, 2H),
6.78 (s, 12H), 4.16 (t, J=5.8Hz, 24H), 3.87 (s, 12H), 3.55 (t, J=5.8Hz, 24H).
?1The signal of hydrogen atom corresponding to 2- chloropyridine is only had found in H NMR spectra, this illustrates bright double dibromo ethoxies
The absorption 2- chloropyridine of pilum [6] the aromatic hydrocarbons crystalline material property of can choose.
PXRD testing result is as shown in Figure 1, relative to double two bromine oxethyl column [6] the aromatic hydrocarbons crystalline materials initially activated
PXRD spectrogram, double two bromine oxethyl columns [6] after placed a period of time in the mixed vapour of 2- chloropyridine and 3- chloropyridine
The PXRD spectrogram of aromatic hydrocarbons crystalline material changes, and spectrogram variation is identical as BrP6 2-CP, this illustrates double two bromine oxethyls
The absorption 2- chloropyridine of column [6] the aromatic hydrocarbons crystalline material property of can choose.
The result of headspace gas chromatography such as Fig. 2, the results showed that, double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials can select
The absorption 2- chloropyridine of selecting property, selectivity 96.4%.
Embodiment 4
The regeneration of double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials: by double two bromine oxethyls of saturation absorption 2- chloropyridine
Column [6] aromatic hydrocarbons crystalline material 30mg is heated 5 hours at 120 DEG C of vacuum drying oven, is denoted as BrP6-D.
Product characterize data manufactured in the present embodiment is as follows:
BrP6-D,1H NMR(400MHz,CDCl3, 298K, ppm) and δ 6.78 (s, 12H), 4.16 (t, J=5.8Hz, 24H),
3.87 (s, 12H), 3.55 (t, J=5.9Hz, 24H).
?1Find that the signal of hydrogen atom corresponding to 2- chloropyridine has disappeared in H NMR spectra, this illustrates double dibromo second
Oxygroup column [6] aromatic hydrocarbons crystalline material has been completed desorption and regeneration, has all discharged to 2- chloropyridine molecule.
PXRD testing result is as shown in Figure 1, relative to double two bromine oxethyl column [6] the aromatic hydrocarbons crystalline materials initially activated
The PXRD spectrogram of PXRD spectrogram, double diethoxy pilum [6] the aromatic hydrocarbons crystalline materials being desorbed is same, this illustrates double dibromo second
Oxygroup column [6] aromatic hydrocarbons crystalline material has completed desorption process.
Embodiment 5
Double two bromine oxethyls column [6] aromatic hydrocarbons crystalline materials recycle: by double two bromine oxethyl columns [6] virtues after regeneration
Hydrocarbon crystalline material 30mg repeats embodiment 3.
Headspace gas chromatography the result shows that, such as Fig. 3, double two bromine oxethyls column [6] aromatic hydrocarbons crystalline material property of can choose
Absorption 2- chloropyridine, and in the experiment of 5 circulation absorptions, selectivity is not substantially reduced.
In addition, it should also be understood that, those skilled in the art can be to this hair after having read foregoing description content of the invention
Bright to make various changes or modifications, these equivalent forms also fall within the scope of the appended claims of the present application.
Claims (8)
1. a kind of separation method of 2- chloropyridine and 3- chloropyridine, which is characterized in that brilliant using double two bromine oxethyl column [6] aromatic hydrocarbons
The mixture of body material adsorbing separation 2- chloropyridine and 3- chloropyridine, described double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials
Structural formula is as follows:
2. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 1, which is characterized in that double dibromo second
The preparation method of oxygroup column [6] aromatic hydrocarbons crystalline material includes: that bis- bromo of 1,1- is molten to benzene diethyl ether addition 1,2- dichloroethanes
In agent, lewis acid is added, reacts 20~30 minutes at 25~30 DEG C, is quenched after reaction with saturated solution of sodium bicarbonate,
Crude product is obtained after washing liquid separation concentration, crude by column chromatography separation, dry activation obtain double two bromine oxethyl columns [6]
Aromatic hydrocarbons crystalline material.
3. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 1 or 2, which is characterized in that the 2- chlorine
The separation method of pyridine and 3- chloropyridine specifically: will double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials be placed in 2- chloropyridine and
In the mixed vapour atmosphere of 3- chloropyridine, temperature be 20~30 DEG C, adsorption time according to 2- chloropyridine reach adsorption saturation when
Between depending on.
4. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 3, which is characterized in that the mixed vapour
The volume ratio of middle 2- chloropyridine and 3- chloropyridine is 0.5~1.5:1.
5. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 1, which is characterized in that use normal heating
Or the mode of heating under reduced pressure removes the 2- chloropyridine and 3- chloropyridine of double two bromine oxethyl column [6] aromatic hydrocarbons crystalline material adsorptions
Mixture.
6. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 5, which is characterized in that the normal heating
Or the temperature of heating under reduced pressure is 30~50 DEG C.
7. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 1, which is characterized in that use heating in vacuum
Mode the 2- chloropyridine molecules of double two bromine oxethyl column [6] aromatic hydrocarbons crystalline materials absorption complexings is desorbed.
8. the separation method of 2- chloropyridine and 3- chloropyridine according to claim 7, which is characterized in that the heating in vacuum
Temperature be 110~130 DEG C.
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| CN111303084A (en) * | 2020-03-12 | 2020-06-19 | 浙江大学 | Method for separating 2-methylfuran and 2, 5-dimethylfuran |
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| CN112142545A (en) * | 2020-09-29 | 2020-12-29 | 浙江大学 | Method for separating isopropyl benzene and alpha-methyl styrene |
| CN114516778A (en) * | 2022-01-20 | 2022-05-20 | 浙江大学杭州国际科创中心 | Method for purifying m-methyl ethylbenzene |
| CN114773258A (en) * | 2022-05-10 | 2022-07-22 | 浙江大学杭州国际科创中心 | Separation and purification method of 2, 6-dimethylpyridine |
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