CN107162959A - The synthetic method of 2 pyridine carboxylic acids - Google Patents
The synthetic method of 2 pyridine carboxylic acids Download PDFInfo
- Publication number
- CN107162959A CN107162959A CN201710428761.0A CN201710428761A CN107162959A CN 107162959 A CN107162959 A CN 107162959A CN 201710428761 A CN201710428761 A CN 201710428761A CN 107162959 A CN107162959 A CN 107162959A
- Authority
- CN
- China
- Prior art keywords
- pyridine carboxylic
- carboxylic acids
- pyridine
- synthetic method
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- 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
- C07D213/04—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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
-
- 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
- C07D213/04—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
- C07D213/06—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 containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/08—Preparation by ring-closure
- C07D213/09—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles
- C07D213/12—Preparation by ring-closure involving the use of ammonia, amines, amine salts, or nitriles from unsaturated compounds
-
- 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
- C07D213/04—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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/04—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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
-
- 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
- C07D213/04—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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The invention provides a kind of synthetic method of 2 pyridine carboxylic acid, organic chemical synthesis field comprises the following steps：The catalyst and acetonitrile that dicyclopentadiene is closed into cobalt, manganese acetate and cobalt acetate composition are added in reactor, and acetylene is passed through at room temperature, temperature reaction is stirred, 2 picolines are made；By 2 picolines, heating becomes steam on heating bed, then by catalyst layer catalysis oxidation after mix with ammonia, vapor and air, you can obtained 2 pyridine carbonitriles；2 pyridine carbonitriles are added in sodium hydroxide solution, heat temperature raising, stirring reaction is cooled to room temperature, suction filtration, after filter cake washing after drying crystallization, you can obtain 2 pyridine carboxylic acids, the present invention has yield high, simple production process, product is easy to separation, " three wastes " few advantage.
Description
Technical field
The present invention relates to organic chemical synthesis field, and in particular to a kind of synthetic method of 2- pyridine carboxylic acids.
Background technology
The molecular formula of pyridine carboxylic acid is：C5H5NO2.In structure be all containing lewis acid and lewis basic functionalities,
It is typical heterocyclic amphoteric compound.Pyridine carboxylic acid series is widely used in medicine, chemical industry, food and life, with not
Alternative effect and value.Therefore scholar and expert both domestic and external have carried out substantial amounts of research to pyridine carboxylic acid synthesis.Pyridine
Formic acid includes tri- kinds of isomers of α, β, γ：Picolinic acid, nicotinic acid and isonicotinic acid.
Wherein, α-pyridine carboxylic acid is known as 2- pyridine carboxylic acids again, and 2- pyridine carboxylic acids are in the middle of a kind of important organic synthesis
Body, fabrication carbocaine medicine is can be used on medical industry, the intermediate such as herbicide and nerve medicine is also acted as, in nerve
Suppress and local anaesthesia aspect is widely used, the huge market demand.What 2- pyridine carboxylic acids still synthesized many pyridine carboxylic acid salt must
Standby raw material, wherein 2- chromium picolinates are the important health medicines of the mankind, be widely used in human body chromium supplementing agent, feed addictive and
Treatment of diabetes etc..
Most of current 2- pyridine carboxylic acids are synthesized by aoxidizing the method for 2- picolines, and conventional oxidizing process has chemistry
Oxidizing process.Chemical oxidation fado, using potassium permanganate, selenium dioxide or potassium bichromate as oxidant, is more ripe synthesis side
Method, but this method cost is high, and a large amount of waste liquids can be produced in production process, pollutes environment, and also it is serious to equipment corrosion.
The content of the invention
(1) technical problem solved
In view of the shortcomings of the prior art, it is high with yield the invention provides a kind of synthetic method of 2- pyridine carboxylic acids, it is raw
Production. art is simple, and product is easy to separation, " three wastes " few advantage.
(2) technical scheme
To realize object above, the present invention is achieved by the following technical programs：
A kind of synthetic method of 2- pyridine carboxylic acids, comprises the following steps：
(1) catalyst and acetonitrile that dicyclopentadiene is closed into cobalt, manganese acetate and cobalt acetate composition are added in reactor, room temperature
Under be passed through acetylene to reactor pressure and rise to 0.8-1.2MPa, stirring is warming up to 140-160 DEG C, reacts 8-10h, and reaction solution is dense
Contracting, rectification and purification, you can obtain 2- picolines；
(2) above-mentioned 2- picolines are heated to 330-370 DEG C on heating bed and become steam, then with ammonia, vapor
By catalyst layer catalysis oxidation after being mixed with air, you can 2- pyridine carbonitriles are made, the catalyst layer includes catalyst, helped
Urge agent and catalytic carrier, the catalyst is germanium oxide, antimony oxide and vanadium oxide, the cocatalyst is copper and zirconium, described
Catalytic carrier is aluminum oxide；
(3) above-mentioned 2- pyridine carbonitriles are added in sodium hydroxide solution, are heated to 70-90 DEG C, stirring reaction 5-
After 7h, room temperature is cooled to, suction filtration is dried, you can obtain 2- pyridine carboxylic acid crude products after filter cake washing, and above-mentioned 2- pyridine carboxylic acids is thick
Product are added in dichloromethane, are heated to reflux stirring and are completely dissolved to it, then the mixed solution of methanol and ethanol is slowly added dropwise, and are dripped
Add after finishing, be cooled to and 5-10h is stirred at room temperature, suction filtration, filtration cakes torrefaction, you can obtain 2- pyridine carboxylic acids after purification.
Preferably, the mass ratio that dicyclopentadiene closes cobalt, manganese acetate and cobalt acetate in the step (1) is 10:2:1.
Preferably, acetylene need to first pass through drying process in the step (1).
Preferably, concentration of sodium hydroxide solution is 40-60% in the step (3).
Preferably, the volume ratio of methanol and ethanol is 2 in mixed solution in the step (3):1.
Preferably, filtration cakes torrefaction temperature is 65-80 DEG C in the step (3).
(3) beneficial effect
The invention provides a kind of synthetic method of 2- pyridine carboxylic acids, with advantages below：
(1) in the production process of 2- picolines, composite catalyst is added, reaction time and reaction temperature is reduced, saved
The energy and production cost are saved, simultaneous reactions pressure is also decreased, and production security is improved；
(2) 2- pyridine carbonitriles are produced using ammoxidation, reaction can be carried out at ambient pressure, yield is high, reaction product is easily divided
From suitable large-scale production, while using the catalyst layer of compounding, improving the service life of catalyst layer, also reducing Jiao
The generation of oil and pernicious gas.
(3) the 2- pyridine carboxylic acids purity that production is obtained is high, and accessory substance is few, is easily purified, it is only necessary to which primary crystallization purity is just
More than 99% can be obtained.
Brief description of the drawings
Fig. 1 is reaction process schematic diagram of the invention.
Embodiment
To make the purpose, technical scheme and advantage of the embodiment of the present invention clearer, below in conjunction with the embodiment of the present invention,
Technical scheme in the embodiment of the present invention is clearly and completely described, it is clear that described embodiment is the present invention one
Divide embodiment, rather than whole embodiments.Based on the embodiment in the present invention, those of ordinary skill in the art are not making
The every other embodiment obtained under the premise of creative work, belongs to the scope of protection of the invention.
Embodiment 1：
1st, a kind of synthetic method of 2- pyridine carboxylic acids, comprises the following steps：
(1) it is 10 in mass ratio dicyclopentadiene to be closed into cobalt, manganese acetate and cobalt acetate:2:The catalyst and acetonitrile of 1 composition
Add in reactor, dry acetylene to reactor pressure is passed through at room temperature and rises to 1.1MPa, stirring is warming up to 145 DEG C, reaction
9.5h, reaction solution concentration, rectification and purification, you can obtain 2- picolines；
(2) above-mentioned 2- picolines are heated to 350-370 DEG C on heating bed and become steam, then with ammonia, vapor
By catalyst layer catalysis oxidation after being mixed with air, you can 2- pyridine carbonitriles are made, the catalyst layer includes catalyst, helped
Urge agent and catalytic carrier, the catalyst is germanium oxide, antimony oxide and vanadium oxide, the cocatalyst is copper and zirconium, described
Catalytic carrier is aluminum oxide；
(3) above-mentioned 2- pyridine carbonitriles are added in the sodium hydroxide solution that concentration is 55%, are heated to 85 DEG C, stir
Mix after reaction 7h, be cooled to room temperature, suction filtration is dried, you can 2- pyridine carboxylic acid crude products are obtained, by above-mentioned 2- pyridines after filter cake washing
Formic acid crude product is added in dichloromethane, is heated to reflux stirring and is completely dissolved to it, then the volume of methanol and ethanol is slowly added dropwise
Than for 2:1 mixed solution, completion of dropping is cooled to after room temperature and stirs 7h, suction filtration, and filter cake is put into 65-80 DEG C of baking oven and dried
Afterwards, you can obtain 2- pyridine carboxylic acids after purification.
Embodiment 2：
1st, a kind of synthetic method of 2- pyridine carboxylic acids, comprises the following steps：
(1) it is 10 in mass ratio dicyclopentadiene to be closed into cobalt, manganese acetate and cobalt acetate:2:The catalyst and acetonitrile of 1 composition
Add in reactor, dry acetylene to reactor pressure is passed through at room temperature and rises to 1MPa, stirring is warming up to 150 DEG C, reacts 9h, instead
Liquid is answered to concentrate, rectification and purification, you can to obtain 2- picolines；
(2) above-mentioned 2- picolines are heated to 350-370 DEG C on heating bed and become steam, then with ammonia, vapor
By catalyst layer catalysis oxidation after being mixed with air, you can 2- pyridine carbonitriles are made, the catalyst layer includes catalyst, helped
Urge agent and catalytic carrier, the catalyst is germanium oxide, antimony oxide and vanadium oxide, the cocatalyst is copper and zirconium, described
Catalytic carrier is aluminum oxide；
(3) above-mentioned 2- pyridine carbonitriles are added in the sodium hydroxide solution that concentration is 45%, are heated to 80 DEG C, stir
Mix after reaction 6h, be cooled to room temperature, suction filtration is dried, you can 2- pyridine carboxylic acid crude products are obtained, by above-mentioned 2- pyridines after filter cake washing
Formic acid crude product is added in dichloromethane, is heated to reflux stirring and is completely dissolved to it, then the volume of methanol and ethanol is slowly added dropwise
Than for 2:1 mixed solution, completion of dropping is cooled to after room temperature and stirs 8h, suction filtration, and filter cake is put into 65-80 DEG C of baking oven and dried
Afterwards, you can obtain 2- pyridine carboxylic acids after purification.
Embodiment 3：
Substantially the same manner as Example 1, difference is, reactor pressure is 0.8MPa in step (1), and temperature is 140 DEG C, instead
Answer 8h；Concentration of sodium hydroxide solution is 40% in step (3), is heated to 70 DEG C, stirring reaction 5h is cooled to after room temperature and stirred
Mix 5h.
Embodiment 4：
Substantially the same manner as Example 1, difference is, reactor pressure is 1.2MPa in step (1), and temperature is 160 DEG C, instead
Answer 10h；Concentration of sodium hydroxide solution is 60% in step (3), is heated to 90 DEG C, stirring reaction 7h is cooled to after room temperature
Stir 10h.
Embodiment 5：
Substantially the same manner as Example 1, difference is, reactor pressure is 0.9MPa in step (1), and temperature is 155 DEG C, instead
Answer 9h；Concentration of sodium hydroxide solution is 55% in step (3), is heated to 75 DEG C, stirring reaction 6h is cooled to after room temperature and stirred
Mix 9h.
It should be noted that herein, such as first and second or the like relational terms are used merely to a reality
Body or operation make a distinction with another entity or operation, and not necessarily require or imply these entities or deposited between operating
In any this actual relation or order.Moreover, term " comprising ", "comprising" or its any other variant are intended to
Nonexcludability is included, so that process, method, article or equipment including a series of key elements not only will including those
Element, but also other key elements including being not expressly set out, or also include being this process, method, article or equipment
Intrinsic key element.In the absence of more restrictions, the key element limited by sentence "including a ...", it is not excluded that
Also there is other identical element in process, method, article or equipment including the key element.
The above embodiments are merely illustrative of the technical solutions of the present invention, rather than its limitations；Although with reference to the foregoing embodiments
The present invention is described in detail, it will be understood by those within the art that：It still can be to foregoing each implementation
Technical scheme described in example is modified, or carries out equivalent substitution to which part technical characteristic；And these modification or
Replace, the essence of appropriate technical solution is departed from the spirit and scope of various embodiments of the present invention technical scheme.
Claims (6)
1. a kind of synthetic method of 2- pyridine carboxylic acids, it is characterised in that comprise the following steps：
(1) catalyst and acetonitrile that dicyclopentadiene is closed into cobalt, manganese acetate and cobalt acetate composition are added in reactor, are led at room temperature
Enter acetylene to reactor pressure and rise to 0.8-1.2MPa, stirring is warming up to 140-160 DEG C, react 8-10h, reaction solution concentration, essence
Evaporate purification, you can obtain 2- picolines；
(2) above-mentioned 2- picolines are heated to 350-370 DEG C on heating bed and become steam, then with ammonia, vapor and sky
By catalyst layer catalysis oxidation after gas mixing, you can 2- pyridine carbonitriles are made, the catalyst layer includes catalyst, cocatalyst
And catalytic carrier, the catalyst is germanium oxide, antimony oxide and vanadium oxide, and the cocatalyst is copper and zirconium, the catalysis
Carrier is aluminum oxide；
(3) above-mentioned 2- pyridine carbonitriles are added in sodium hydroxide solution, are heated to after 70-90 DEG C, stirring reaction 5-7h,
Room temperature is cooled to, suction filtration is dried, you can obtain 2- pyridine carboxylic acid crude products, above-mentioned 2- pyridine carboxylic acids crude product is added after filter cake washing
Enter into dichloromethane, be heated to reflux stirring and be completely dissolved to it, then the mixed solution of methanol and ethanol is slowly added dropwise, drip
Bi Hou, is cooled to and 5-10h is stirred at room temperature, suction filtration, filtration cakes torrefaction, you can obtain 2- pyridine carboxylic acids after purification.
2. the synthetic method of 2- pyridine carboxylic acids as claimed in claim 1, it is characterised in that bicyclic penta 2 in the step (1)
The mass ratio that alkene closes cobalt, manganese acetate and cobalt acetate is 10:2:1.
3. the synthetic method of 2- pyridine carboxylic acids as claimed in claim 1, it is characterised in that acetylene needs elder generation in the step (1)
By drying process.
4. the synthetic method of 2- pyridine carboxylic acids as claimed in claim 1, it is characterised in that sodium hydroxide in the step (3)
Solution concentration is 40-60%.
5. the synthetic method of 2- pyridine carboxylic acids as claimed in claim 1, it is characterised in that mixed solution in the step (3)
The volume ratio of middle methanol and ethanol is 2:1.
6. the synthetic method of 2- pyridine carboxylic acids as claimed in claim 1, it is characterised in that filtration cakes torrefaction in the step (3)
Temperature is 65-80 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710428761.0A CN107162959A (en) | 2017-06-08 | 2017-06-08 | The synthetic method of 2 pyridine carboxylic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710428761.0A CN107162959A (en) | 2017-06-08 | 2017-06-08 | The synthetic method of 2 pyridine carboxylic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN107162959A true CN107162959A (en) | 2017-09-15 |
Family
ID=59825689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710428761.0A Pending CN107162959A (en) | 2017-06-08 | 2017-06-08 | The synthetic method of 2 pyridine carboxylic acids |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107162959A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108658848A (en) * | 2018-05-05 | 2018-10-16 | 湖北荆洪生物科技股份有限公司 | A kind of production technology of 2,2`- bipyridyls |
| CN111569947A (en) * | 2020-06-19 | 2020-08-25 | 安徽国星生物化学有限公司 | Method for synthesizing 2-methylpyridine organic cobalt catalyst |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101602715A (en) * | 2009-04-29 | 2009-12-16 | 南通醋酸化工股份有限公司 | The synthetic method of 2-pyridine carboxylic acid |
| CN101602719A (en) * | 2009-04-29 | 2009-12-16 | 南通醋酸化工股份有限公司 | The synthetic method of 4-cyanopyridine |
| CN102372666A (en) * | 2010-08-11 | 2012-03-14 | 东营石大宏益化工有限公司 | Method for synthesizing alfa-methylpyridine through continuous catalytic distillation |
-
2017
- 2017-06-08 CN CN201710428761.0A patent/CN107162959A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101602715A (en) * | 2009-04-29 | 2009-12-16 | 南通醋酸化工股份有限公司 | The synthetic method of 2-pyridine carboxylic acid |
| CN101602719A (en) * | 2009-04-29 | 2009-12-16 | 南通醋酸化工股份有限公司 | The synthetic method of 4-cyanopyridine |
| CN102372666A (en) * | 2010-08-11 | 2012-03-14 | 东营石大宏益化工有限公司 | Method for synthesizing alfa-methylpyridine through continuous catalytic distillation |
Non-Patent Citations (2)
| Title |
|---|
| 张永华等: "吡啶甲酸合成方法综述", 《首都师范大学学报》 * |
| 黎四芳等: "《从乙炔制备精细化学品》", 31 December 2016 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108658848A (en) * | 2018-05-05 | 2018-10-16 | 湖北荆洪生物科技股份有限公司 | A kind of production technology of 2,2`- bipyridyls |
| CN108658848B (en) * | 2018-05-05 | 2021-04-02 | 湖北荆洪生物科技股份有限公司 | Production process of 2,2' -bipyridine |
| CN111569947A (en) * | 2020-06-19 | 2020-08-25 | 安徽国星生物化学有限公司 | Method for synthesizing 2-methylpyridine organic cobalt catalyst |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106925349A (en) | A kind of solid supported type metal porphyrin catalyst and its application in terms of maleic acid is prepared | |
| CN107162959A (en) | The synthetic method of 2 pyridine carboxylic acids | |
| CN101579625A (en) | Catalyst and reaction process for preparing pyruvic acid by lactic acid in catalytic oxydehydrogenation way | |
| Yang et al. | Two 1D Anderson-Type polyoxometalate-based metal–organic complexes as bifunctional heterogeneous catalysts for CO2 photoreduction and sulfur oxidation | |
| CN101623648B (en) | Catalyst of picolinic acid synthesized by selectively oxygenizing picoline as well as preparation method and application thereof | |
| CN107056697A (en) | A kind of method for synthesizing 3 cyanopyridines | |
| Li et al. | Hydrothermal syntheses and crystal structures of crystalline catalysts based on 3-D Ln3+–pdc2− frameworks and [BW12O40] 5− and their heterogeneous photocatalytic oxidation of thiophene | |
| CN111807970A (en) | Method for preparing N-benzylaniline by catalytic oxidation of aniline with polyoxometallate | |
| CN101623628B (en) | Catalyst of synthesized picolinic acid and as well as preparation method and application thereof | |
| CN108970604B (en) | Molybdenum vanadium niobium-based composite oxide and synthesis method and application thereof | |
| US10703720B2 (en) | Method for preparing chromium(III) pyridine-2-carboxylate using 2-OP rectification residues | |
| Peng et al. | Syntheses, structures and photocatalytic degradation of organic dyes for two isostructural copper coordination polymers involving in situ hydroxylation reaction | |
| CN106117041A (en) | A kind of synthetic method of isooctyl acid bismuth | |
| CN109251168B (en) | Method for preparing pyridine-2-formic acid by using 2-OP rectification residues | |
| Peng et al. | A novel Anderson-type polyoxometalate: hydrothermal synthesis, crystal structure, and catalytic performance of (H3O)[(3-C5H7N2) 2 (Cr (OH) 6Mo6O18)]· 3H2O | |
| Tang et al. | Photocatalytic Reduction of Nitrobenzene to Aniline by an Intriguing {Ru (C6H6)}-Based Heteropolytungstate | |
| Chen et al. | Self-assembly, bifunctional electrocatalytic behavior, and photocatalytic property of host–guest metal-oxide-based coordination polymers | |
| CN104387317B (en) | Preparation method and separation and purification method for 6-chloronicotinic acid | |
| CN106045864A (en) | Production process for preparing 4-chloro-2,5-dimethoxyaniline with hydrazine hydrate catalytic reduction method | |
| CN108299290A (en) | A kind of method optimization of 3- picolines synthesis nicotinonitrile | |
| CN103833628A (en) | Synthetic method of chromium picolinate | |
| CN110698333A (en) | Method for continuously synthesizing o-phthalaldehyde by using microchannel reaction device | |
| CN109096184B (en) | Preparation method of picolinic acid compound | |
| CN108640829A (en) | A kind of method that aqueous catalysis Oxidation of Lactic prepares pyruvic acid | |
| CN201864678U (en) | Novel tetrachloro phthalonitrile production device |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20170915 |