CN108164460A - A kind of method for preparing 3- methylpyridine N oxides - Google Patents
A kind of method for preparing 3- methylpyridine N oxides Download PDFInfo
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- CN108164460A CN108164460A CN201810030946.0A CN201810030946A CN108164460A CN 108164460 A CN108164460 A CN 108164460A CN 201810030946 A CN201810030946 A CN 201810030946A CN 108164460 A CN108164460 A CN 108164460A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- 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
- C07D213/89—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 with hetero atoms directly attached to the ring nitrogen atom
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Abstract
A kind of method for preparing 3 picoline N oxides, belongs to pesticide/pharmaceutical chemicals intermediate synthetic technology.The present invention is quickly mixed in micro-mixer with hydrogen peroxide by 3 picolines and completes to aoxidize under the high temperature conditions in microreactor, and 3 picoline N oxide solutions of generation obtain product by further flash distillation.Compared to prior art, oxidation reaction process is carried out in microreactor, heat exchange characteristics are more preferable, are conducive to the controllability of intensified response, eliminate reaction hot spot in equipment, improve the operation temperature upper limit；Further, since quick mixing easy to implement in micro-mixer, moment reaches uniform reaction environment, and the efficiency of reaction improves, and reacts flux amplification easy to implement；It is optimized with the technique, the utilization ratio higher of hydrogen peroxide, while raw material is saved, can also reduce the energy consumption of the techniques such as subsequent purification.
Description
Technical field
The present invention relates to a kind of preparation methods of 3- methylpyridine N oxides, belong to pesticide/pharmaceutical chemicals intermediate
Synthesis technical field.
Background technology
3- methylpyridine N oxides (3-METHYLPYRIDINE N-OXIDE) be usually white to light yellow crystal,
It is the intermediate of the important drugs such as imidacloprid, acetamiprid synthesis.At present, by 3- methylpyridine N oxides and phosphorus oxychloride
The chloro- 3- picolines of 2- and chloro--methylpyridine for reacting synthesis are all widely used in terms of pesticide, medical synthesis.
In current research (CN102718705B, CN105001155A, CN104974088B, CN 106749000A),
Generally using hydrogen peroxide as oxidant, wherein the mass fraction of hydrogen peroxide is between 25%~30%.In catalyst (titanium
Si molecular sieves, transition metal oxide or its esters etc.) under the action of, it is being catalyzed under heating condition with 3- picolines raw material
It reacts and is made in the presence of agent.Specifically, certain 3- picolines are added in reaction kettle, add in acid and catalyst, 60~
75 DEG C are added dropwise hydrogen peroxide in batches, then keep the temperature 7~8h, are then flashed and obtain 3- methylpyridine N oxides.Due to oxygen
Change exothermic heat of reaction, and it is efficient combustion adjuvant that hydrogen peroxide, which decomposes the oxygen generated, makes such technique in actual mechanical process
There are a series of stubborn problems such as temperature-responsive is slow, reaction time is long, amplification difficulty, are added significantly to the energy consumption of production process
Material consumption.Therefore it is very necessary to develop more efficient, safe synthetic technology.
Invention content
The object of the present invention is to provide a kind of methods for preparing 3- methylpyridine N oxides, it is intended to solve practical operation
A series of stubborn problems such as existing temperature-responsive is slow in the process, reaction time is long, amplification difficulty, further reduce and produced
Energy and material consumption in journey, and then make preparation process more efficient and more safely carry out.
Technical scheme is as follows：
A kind of method for preparing 3- methylpyridine N oxides, it is characterised in that described method includes following steps：
1) the feed liquid A and catalyst of 3- picolines are positioned in A storage tanks and uniformly mixed, feed liquid A is made, wherein being catalyzed
Agent is the 1%~5% of 3- picoline mass fractions；Hydrogen peroxide feed liquid B is positioned in B storage tanks simultaneously；
2) feed liquid A and feed liquid B are delivered in micro-mixer, make the total flow of feed liquid A and feed liquid B being averaged at mixing
Flow velocity is at least 1m/s, obtains mixed liquor C；Mixed liquor C occurs in the microreactor pyroreaction section that temperature is 75~90 DEG C
Oxidation reaction obtains the reaction solution D of the methylpyridine N oxide containing 3-；
3) it is transmitted back in A storage tanks after reaction solution D being cooled to 20~30 DEG C in microreactor sub-cooled section, with A
Original feed liquid in storage tank mixes under stiring, until the feed liquid in B storage tanks is all mixed and anti-by micro-mixer with feed liquid A
It answers, the mixed solution E of the methylpyridine N oxide containing 3- is obtained in A storage tanks；
4) mixed solution E is input in microreactor and reacted, and the reaction solution after reaction is passed through in A storage tanks,
After the concentration of hydrogen peroxide in A storage tanks is at or below 1%, stopping is passed through solution E, then pumps out anti-in microreactor
It answers in liquid to A storage tanks, the solution F of the methylpyridine N oxide containing 3- is obtained in A storage tanks；
5) the solution F that step 4) obtains in flash tank is flashed, is distilled out of 3- methylpyridine N oxides,
The 3- methylpyridine N oxides being distilled out of obtain the product of 3- methylpyridine N oxides after fractional condensation, drying；It will
Remaining solid object recycling containing catalyst after flash distillation.
Preferably, the catalyst is using phosphomolybdic acid and the mixture of molybdenum trioxide, wherein the mass ratio of the two is 1：2 arrive
2：Between 1.
Preferably, in step 1), the purity of used 3- picolines should be greater than or equal to 80%；The hydrogen peroxide
Mass fraction between 25%~35%, pH is buffered to 3.8~4.2 ranges with phosphate buffer.
Preferably, the molar ratio of hydrogen peroxide and 3- picolines is 1.1~1.2 in step 2)：1.
In above-mentioned technical proposal, the micro-mixer is preferably using micro-channel mixer, film dispersion micro-mixer or micro-
Sieve pore mixer.
The technical characteristic of the present invention also resides in：Agitating device is equipped in the A storage tanks, and the temperature control of A storage tanks (1) exists
Between 20~30 DEG C.
It is furthermore preferred that mixed liquor C reacts in microreactor in step 3), the reaction time should ensure that any time reaction is molten
The concentration of hydrogen peroxide is equal to or less than 5% in liquid D.
Compared with prior art, the present invention haing the following advantages and the technique effect of high-lighting：In the present invention, using micro- anti-
Answer technique, 3- picolines-catalyst mixture quickly mixed with hydrogen peroxide in micro-mixer, and under the high temperature conditions in
Oxidation reaction is carried out in microreactor, compared to existing research, it would be desirable to which the oxidation reaction of heating is improved to from reaction kettle
It is carried out in microreactor, can effectively avoid and directly heated to containing a large amount of feed liquid containers, so as to be easier to realize to reaction
It is precisely controlled；Under the technique of the present invention, the exchange capability of heat of equipment is strengthened significantly, and oxidation reaction can be in up to 90 DEG C of temperature
The lower safety and steady of degree carries out, and faster, the time that raw material dosage is lower, single batch reaction is required is more for the reaction rate of oxidation reaction
Short, the follow-up flash separation cost of product feed liquid is lower；Two fluids is realized in micro-mixer rapidly and efficiently to be mixed, and moment reaches
Uniform reaction environment, reaction efficiency are high；The flux amplification process of micro- reaction process is more succinct, the amplification for producing technical grade
It is more easy to realize.
Description of the drawings
Fig. 1 is the process flow chart of the present invention.
In figure：1--A storage tanks；2-B storage tanks；3-3- picolines and transport catalyst pump；4- hydrogen peroxide transports pump；5- is micro-
Mixer；6- microreactor pyroreaction sections；7- microreactor sub-cooled sections；8- flash separators；9-3- picolines-N-
Oxide product；10- catalytic agent reuses.
Specific embodiment
The present invention will be further described with reference to the accompanying drawings and examples.
Referring to Fig. 1, a kind of method for preparing 3- methylpyridine N oxides provided by the invention specifically includes as follows
Step：
1) the feed liquid A and catalyst of 3- picolines are positioned in A storage tanks 1, are allowed to be uniformly mixed at normal temperatures, A storages
Agitating device in tank 1 should be set, be kept stirring, making the feed liquid in A storage tanks 1, wherein catalyst is 3- always in uniform state
The 1%~5% of picoline mass fraction；The catalyst preferably uses the mixture of phosphomolybdic acid and molybdenum trioxide, the two
Mass ratio is 1：2~2：Between 1, it is possible to use it is other to have the catalyst for being catalyzed the reaction effect, such as Titanium Sieve Molecular Sieve, transition
Metal oxide or its esters etc.；The purity of used 3- picolines should be greater than or equal to 80%；The hydrogen peroxide
Mass fraction preferably between 25%~35%, and need to be buffered with phosphate buffer, be allowed to pH between 3.8~4.2.Together
When hydrogen peroxide feed liquid B is positioned in B storage tanks 2；Microreactor sub-cooled section 7 is controlled, makes A storage tanks 1 in operating process
Temperature is always positioned between 20~30 DEG C.
2) feed liquid A and feed liquid B are delivered in micro-mixer 5, are quickly mixed at normal temperatures, obtain mixed liquor C；Its
The molar ratio of middle hydrogen peroxide and 3- picolines is preferably 1.1~1.2：1, this is to ensure that the substance item that reaction fully occurs
Part；Mean flow rate of the total flow of feed liquid A and feed liquid B at mixing is at least 1m/s during mixing, this is to ensure that feed liquid A and feed liquid
B realizes the essential condition of quick mixing and then fast reaction in micro-mixer；Flow at mixing should ensure that hydrogen peroxide
Molar ratio with 3- picolines is 0.05~0.25：Between 1, which contributes to the controllability of intensified response, is fully adding
The decomposition of hydrogen peroxide is reduced while fast main reaction；Mixed liquor C is obtained after mixing, make mixed liquor C temperature be 75~90 DEG C
Microreactor pyroreaction section 6 in oxidation reaction occurs, the reaction solution D of the methylpyridine N oxide containing 3- can be obtained；
Reaction time in microreactor pyroreaction section 6 should ensure that the concentration of hydrogen peroxide in any time reaction solution D be equal to or
Less than 5%.
Micro-channel mixer can be used in the micro-mixer, film dispersion micro-mixer or Microtraps hole mixer etc. have soon
The mixing arrangement of fast mixed effect, for example, it is micro- mixed described in patent CN200510012114.9, CN200710177813.8
Clutch, the micro-mixer can realize the efficient mixing between two fluids, and moment reaches uniform reaction environment, other to realize soon
The device of speed mixing can also be used for the present invention.
3) reaction solution D is cooled to 30 DEG C in microreactor sub-cooled section 7 hereinafter, usually at 20~30 DEG C, so
After be transmitted back in A storage tanks 1, mixed under stiring with original feed liquid in A storage tanks 1, until B storage tanks 2 in feed liquid all pass through
Micro-mixer 5 is mixed and is reacted with feed liquid A, later into A storage tanks 1；A storage tanks 1 need to carry out isothermal holding, are controlled by cooling down
Its temperature is made between 20~30 DEG C；The mixed solution E of the methylpyridine N oxide containing 3- is obtained in A storage tanks 1；
4) mixed solution E is input in microreactor pyroreaction section 6 and reacted, and the reaction solution after reaction is led to
Enter in A storage tanks 1, after the concentration of hydrogen peroxide in A storage tanks 1 is at or below 1%, stopping is passed through solution E, obtains first containing 3-
The solution F of pyridine-N-oxide；
5) the solution F that step 4) obtains in flash tank 8 is flashed, is distilled out of 3- methylpyridine N oxides,
The 3- methylpyridine N oxides being distilled out of obtain the product of 3- methylpyridine N oxides after fractional condensation, drying；It will
The remaining solid object containing catalyst is recycled after flash distillation, and is added in A storage tanks 1 and is continuing with.
Several specific embodiments are enumerated below, so that those of ordinary skill in the art further appreciate that the present invention.
Embodiment 1
1) the 3- picolines and 2.4g catalyst preparations for weighing 240g are feed liquid A, weigh 275g35wt% hydrogen peroxide
Solution with phosphate buffer stabilization to pH=4, is formulated as feed liquid B；Wherein catalyst for phosphomolybdic acid and molybdenum trioxide in mass ratio
2：1 mixes.
2) heating temperature of control microreactor pyroreaction section 6 is 75 DEG C, the feed liquid A and feed liquid B obtained in step 1)
It is passed through in micro-mixer 5 with the flow of 50mL/min and 2mL/min respectively, wherein A is continuous phase, and B is dispersed phase, micro-mixer
5 structure is referring to patent CN200510012114.9, containing 5 parallel channels, using 10 microns of stainless steel porous media as point
Dispersion media.Residence times of the mixed liquor C in microreactor pyroreaction section 6 is 4min.Mixing and reaction are completed by about 2h
Process, using the product solution in ultra performance liquid chromatography calibration A storage tanks 1, the yield of 3- methylpyridine N oxides reaches
82.4%.
Embodiment 2
1) the 3- picolines and 9.6g catalyst preparations for weighing 240g are feed liquid A, weigh 275g35wt% hydrogen peroxide
Solution with phosphate buffer stabilization to pH=4, is formulated as feed liquid B；Wherein catalyst for phosphomolybdic acid and molybdenum trioxide in mass ratio
1：1 mixes.
2) heating temperature of control microreactor pyroreaction section 6 is 90 DEG C, the feed liquid A and feed liquid B obtained in step 1)
It is passed through in micro-mixer 5 with the flow of 50mL/min and 5mL/min respectively, wherein A is continuous phase, and B is dispersed phase, micro-mixer
5 structure is referring to patent CN200510012114.9, containing 5 parallel channels, using 10 microns of stainless steel porous media as point
Dispersion media.Residence times of the mixed liquor C in microreactor pyroreaction section 6 is 6min.It completes to mix by about 0.8h and anti-
Process is answered, using the product solution in ultra performance liquid chromatography calibration A storage tanks 1, the yield of 3- methylpyridine N oxides reaches
90.7%.
Embodiment 3
1) the 3- picolines and 12.0g catalyst preparations for weighing 240g are feed liquid A, weigh 360g27wt% hydrogen peroxide
Solution with phosphate buffer stabilization to pH=4, is formulated as feed liquid B；Wherein catalyst for phosphomolybdic acid and molybdenum trioxide in mass ratio
1：2 mix.
2) heating temperature of control microreactor pyroreaction section 6 is 80 DEG C, the feed liquid A and feed liquid B obtained in step 1)
It is passed through in micro-mixer 5 with the flow of 50mL/min and 5mL/min respectively, wherein A is continuous phase, and B is dispersed phase, micro-mixer
5 structure is referring to patent CN200510012114.9, containing 10 parallel channels, using 10 microns of stainless steel porous media as point
Dispersion media.Residence times of the mixed liquor C in microreactor pyroreaction section 6 is 4min.It completes to mix by about 2.6h and anti-
Process is answered, is demarcated using ultra performance liquid chromatography, the yield of 3- methylpyridine N oxides reaches 91.0%.
Embodiment 4
1) the 3- picolines and 24g catalyst preparations for weighing 480g are feed liquid A, weigh 550g 35wt% hydrogen peroxide
Solution with phosphate buffer stabilization to pH=4, is formulated as feed liquid B；Wherein catalyst for phosphomolybdic acid and molybdenum trioxide in mass ratio
1：1 mixes.
2) heating temperature of control microreactor pyroreaction section 6 is 85 DEG C, the feed liquid A and feed liquid B obtained in step (1)
It is passed through in micro-mixer 5 with the flow of 100mL/min and 5mL/min respectively, wherein A is continuous phase, and B is dispersed phase, microring array
The structure of device 5 is 10 referring to patent CN200710177813.8, the wherein quantity of parallel channels.Mixed liquor C is in microreactor
Residence time in pyroreaction section 6 is 2min.Mixing is completed by about 1.6h and reaction process obtains product solution E1, is used
Ultra performance liquid chromatography is demarcated, and the yield of 3- methylpyridine N oxides reaches 85.0%.
3) temperature of microreactor pyroreaction section 6 is down to 75 DEG C, continues cycling through solution E 12h, reaction is made further to turn
Change, obtain final products solution F.It is demarcated using ultra performance liquid chromatography, the yield of 3- methylpyridine N oxides reaches
90.4%.
Embodiment 5
1) the 3- picolines and 30g catalyst preparations for weighing 1000g are feed liquid A, weigh 1200g 35wt% peroxidating
Hydrogen solution with phosphate buffer stabilization to pH=4, is formulated as feed liquid B.Feed liquid B is divided into B1 and B2, it is spare；Wherein it is catalyzed
Agent is phosphomolybdic acid and molybdenum trioxide in mass ratio 1：1 mixes.
2) temperature of control microreactor pyroreaction section 6 is 85 DEG C, the feed liquid A obtained in step 1) and feed liquid B1 difference
It is passed through in micro-mixer 5 with the flow of 200mL/min and 20mL/min, wherein A is continuous phase, and B1 is dispersed phase, micro-mixer 5
Structure referring to patent CN201110179977.0, the quantity of straight slot is 1 wherein on first fluid distribution grid, the width of straight slot
For 2mm, length-width ratio 5.The quantity of straight slot is 1 on fluid mixed plate, and the width of straight slot is 1mm, depth 0.3mm.Mixed liquor C
Residence time in microreactor pyroreaction section 6 is 2min.Mixing is completed by about 0.5h and reaction process obtains product
Solution E 1.
3) heating temperature of control microreactor pyroreaction section 6 is 85 DEG C, the feed liquid E1 and feed liquid obtained in step 2)
B2 is passed through with the flow of 200mL/min and 10mL/min in micro-mixer respectively, and wherein E1 is continuous phase, and B2 is dispersed phase, micro-
The structure of mixer 5 is the same as described in (2).Residence times of the mixed liquor C in microreactor pyroreaction section 6 is 2min.By
About 1h completes mixing and reaction process obtains product solution E2, is demarcated using ultra performance liquid chromatography, 3- picolines-N-
The yield of oxide reaches 87.0%.
4) temperature of microreactor pyroreaction section 6 is down to 75 DEG C, continues cycling through solution E 21h, it is molten to obtain final products
Liquid F.It is demarcated using ultra performance liquid chromatography, the yield of 3- methylpyridine N oxides reaches 94.6%.
Embodiment 6
1) the 3- picolines and 30g catalyst preparations for weighing 1000g are feed liquid A, weigh 1400g 30wt% peroxidating
Hydrogen solution with phosphate buffer stabilization to pH=4, is formulated as feed liquid B.Feed liquid B is divided into B1 and B2, it is spare；Wherein it is catalyzed
Agent is phosphomolybdic acid and molybdenum trioxide in mass ratio 1：1 mixes.
2) temperature of control microreactor pyroreaction section 6 is 85 DEG C, the feed liquid A obtained in step 1) and feed liquid B1 difference
It is passed through in micro-mixer 5 with the flow of 200mL/min and 20mL/min, wherein A is continuous phase, and B1 is dispersed phase, micro-mixer 5
Structure referring to patent CN201110179977.0, the quantity of straight slot is 1 wherein on first fluid distribution grid, the width of straight slot
For 2mm, length-width ratio 5.The quantity of straight slot is 1 on fluid mixed plate, and the width of straight slot is 1mm, depth 0.3mm.By about
0.5h completes mixing and reaction process obtains product solution E1.
3) temperature of control microreactor pyroreaction section 6 is 85 DEG C, B2 points of the feed liquid E1 obtained in step 2) and feed liquid
It is not passed through in micro-mixer 5 with the flow of 200mL/min and 10mL/min, wherein E1 is continuous phase, and B2 is dispersed phase, microring array
The structure of device 5 is the same as described in (2).Residence times of the mixed liquor C in microreactor pyroreaction section 6 is 2min.By about 1h
It completes mixing and reaction process obtains product solution E2, demarcated using ultra performance liquid chromatography, 3- picolines-N- oxidations
The yield of object reaches 85.7%.
4) temperature of microreactor pyroreaction section 6 is down to 75 DEG C, continues cycling through solution E 21h, it is molten to obtain final products
Liquid F.It is demarcated using ultra performance liquid chromatography, the yield of 3- methylpyridine N oxides reaches 94.1%.
Claims (7)
- A kind of 1. method for preparing 3- methylpyridine N oxides, it is characterised in that described method includes following steps：1) the feed liquid A and catalyst of 3- picolines are positioned in A storage tanks (1) and uniformly mixed, feed liquid A is made, wherein being catalyzed Agent is the 1%~5% of 3- picoline mass fractions；Hydrogen peroxide feed liquid B is positioned in B storage tanks (2) simultaneously；2) feed liquid A and feed liquid B are delivered in micro-mixer (5), make the total flow of feed liquid A and feed liquid B being averaged at mixing Flow velocity is at least 1m/s, obtains mixed liquor C；Mixed liquor C is sent out in the microreactor pyroreaction section (6) that temperature is 75~90 DEG C Raw oxidation reaction, obtains the reaction solution D of the methylpyridine N oxide containing 3-；3) it is transmitted back in A storage tanks (1) after reaction solution D being cooled to 20~30 DEG C in microreactor sub-cooled section (7), with Original feed liquid in A storage tanks (1) mixes under stiring, until the feed liquid in B storage tanks (2) all passes through micro-mixer (5) and material Liquid A is mixed and is reacted, and the mixed solution E of the methylpyridine N oxide containing 3- is obtained in A storage tanks (1)；4) mixed solution E is input in microreactor pyroreaction section (6) and reacted, and the reaction solution after reaction is passed through In A storage tanks (1), after the concentration of hydrogen peroxide in A storage tanks (1) is at or below 1%, stopping is passed through solution E, then pumps out In reaction solution to A storage tanks (1) in microreactor (6) and microreactor sub-cooled section (7), obtained in A storage tanks (1) containing 3- The solution F of methylpyridine N oxide；5) the solution F that step 4) obtains in flash separator (8) is flashed, is steamed 3- methylpyridine N oxides Go out, the 3- methylpyridine N oxides being distilled out of obtain the production of 3- methylpyridine N oxides after fractional condensation, drying Product；Remaining solid object containing catalyst after flash distillation is recycled.
- 2. a kind of method for preparing 3- methylpyridine N oxides according to claim 1, which is characterized in that described to urge Agent is using phosphomolybdic acid and the mixture of molybdenum trioxide, wherein the mass ratio of the two is 1：2~2：Between 1.
- 3. a kind of method for preparing 3- methylpyridine N oxides according to claim 1 or 2, it is characterised in that：Step 1) in, the purity of used 3- picolines is greater than or equal to 80%；The mass fraction of the hydrogen peroxide 25%~ Between 35%, pH is buffered to 3.8~4.2 ranges with phosphate buffer.
- A kind of 4. method for preparing 3- methylpyridine N oxides according to claim 3, which is characterized in that step 2) In, the feed intake molar ratio of total amount of hydrogen peroxide and 3- picolines is 1.1~1.2：1, and the flow at mixing ensures peroxide The molar ratio for changing hydrogen and 3- picolines is 0.05~0.25：Between 1.
- 5. a kind of method for preparing 3- methylpyridine N oxides according to claim 1, which is characterized in that described Micro-mixer is micro-channel mixer, film disperses micro-mixer or Microtraps hole mixer etc..
- A kind of 6. method for preparing 3- methylpyridine N oxides according to claim 1, which is characterized in that the A storages Agitating device is equipped in tank (1), and the temperature of A storage tanks (1) is controlled between 20~30 DEG C.
- A kind of 7. method for preparing 3- methylpyridine N oxides according to claim 1, which is characterized in that step 3) Middle mixed liquor C reacts in microreactor, and the reaction time is that the concentration of hydrogen peroxide in any time reaction solution D is equal to or low In 5%.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1736577A (en) * | 2005-07-08 | 2006-02-22 | 清华大学 | Multi-channeled micro-structured reactor |
| CN102942523A (en) * | 2012-12-05 | 2013-02-27 | 寿光富康制药有限公司 | Preparation method of omeprazole intermediate 2,3,5-trimethylpyridyl-N-oxide |
| CN103570617A (en) * | 2013-11-15 | 2014-02-12 | 浙江荣凯化工科技有限公司 | Preparation method of 3-cyano-pyridine N-oxide |
| CN104447531A (en) * | 2014-11-27 | 2015-03-25 | 爱斯特（成都）生物制药有限公司 | Preparation method of 3,5-dibromopyridine-N-oxide |
| CN105153019A (en) * | 2015-08-10 | 2015-12-16 | 安徽国星生物化学有限公司 | 2-pyridinemethanol and synthetic method thereof |
-
2018
- 2018-01-12 CN CN201810030946.0A patent/CN108164460B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1736577A (en) * | 2005-07-08 | 2006-02-22 | 清华大学 | Multi-channeled micro-structured reactor |
| CN102942523A (en) * | 2012-12-05 | 2013-02-27 | 寿光富康制药有限公司 | Preparation method of omeprazole intermediate 2,3,5-trimethylpyridyl-N-oxide |
| CN103570617A (en) * | 2013-11-15 | 2014-02-12 | 浙江荣凯化工科技有限公司 | Preparation method of 3-cyano-pyridine N-oxide |
| CN104447531A (en) * | 2014-11-27 | 2015-03-25 | 爱斯特（成都）生物制药有限公司 | Preparation method of 3,5-dibromopyridine-N-oxide |
| CN105153019A (en) * | 2015-08-10 | 2015-12-16 | 安徽国星生物化学有限公司 | 2-pyridinemethanol and synthetic method thereof |
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