CN106831572A - A kind of preparation method of quinolinic acid - Google Patents
A kind of preparation method of quinolinic acid Download PDFInfo
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- CN106831572A CN106831572A CN201611058883.7A CN201611058883A CN106831572A CN 106831572 A CN106831572 A CN 106831572A CN 201611058883 A CN201611058883 A CN 201611058883A CN 106831572 A CN106831572 A CN 106831572A
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- CN
- China
- Prior art keywords
- acid
- preparation
- quinolinic acid
- quinolinic
- quinoline
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- Organic Chemistry (AREA)
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Abstract
The invention discloses a kind of preparation method of quinolinic acid.With quinoline as raw material, preparation method includes the present invention：Oxidation, alkaline hydrolysis, acidifying.The preparation method is simple and quick, sewage zero-discharge can be realized in process of production, speed of production can improve 3 ~ 4 times of production efficiency than electrolysis production quinolinic acid, used catalyst is more cheap than common sodium chlorate oxidizing process, production auxiliary material used can be reclaimed to be recycled, and separate out the filtrate after quinolinic acid acid adding can separate out repeatedly, and the rate of recovery is up to 98%, greatly economize on resources, wide market.
Description
Technical field
The present invention relates to chemical field, and in particular to a kind of preparation method of quinolinic acid.
Technical background
Quinolinic acid is a kind of important agricultural chemicals, medicine and pressure sensitive dye intermediate.It can be used for synthesis containing pyridine or quinoline ring
Imidazolinone herbicide.Can be used for synthetic antibiotic.The synthetic method of quinolinic acid is more, according to initiation material not
Together, following two methods can be divided into：8-hydroxyquinoline oxidizing process and quinoline oxidizing process.Because 8-hydroxyquinoline is expensive,
Use quinoline oxidizing process mostly at present, according to the difference of oxidant, quinoline oxidizing process can be divided into four kinds of methods again：（1）Gao Meng
Sour potassium oxidizing process；（2）Hydrogen peroxide oxidation method；（3）Hydrogen peroxide-sodium hypochlorite co-oxidation method；（4）Sodium chlorate oxidizing process.Gao Meng
The reaction of sour potassium oxidizing process is violent, and selectivity is low, and product complicated difficult is isolating and purifying.Hydrogen peroxide oxidation method and hydrogen peroxide --- secondary chlorine
Sour sodium co-oxidation method is required to a large amount of more than 50% hydrogen peroxide, and the reaction time is long.Utilization rate of equipment and installations is low.Sodium chlorate oxidizing process
Reaction condition is gentle, and the reaction time is relatively short, and selectivity is good, and synthesis yield is high, but the catalyst price that tradition is used at present
Costliness, a large amount of productions of serious restriction to quinolinic acid.
The content of the invention
For problem above, the present invention is catalyst by adding potassium permanganate in oxidation stage, replaces traditional catalyst, is carried
A kind of preparation method of quinolinic acid is supplied.Potassium permanganate is cheap, at the same catalytic effect effect is more compared with traditional catalyst
It is good.
To achieve these goals, the technical scheme taken：A kind of preparation method of quinolinic acid, the method includes following
Step：
1st step：Oxidation, generation quinolinic acid copper is aoxidized using quinoline, cupric oxide, sulfuric acid and sodium chlorate, while adding permanganic acid
Potassium is catalyst；
Second step：Alkaline hydrolysis, reacts 1 hour filtering cupric oxide under the conditions of PH10, and activated carbon alkalescence is decolourized；
Third step：Acidifying, PH3 is neutralized in alkaline destainer acid adding, plus activated carbon is acid decolourizes, acid destainer acid adding again
Product is separated out, white products are filtered to obtain.
Further, the quinoline for being used is that purity is 99%.
Further, the intermediate for being used is cupric oxide, and can be recycled.
Further, this method carries out adsorption bleaching using activated carbon to product, using can be by processing Reusability.
Further, the filtrate that product is filtrated to get after acidifying acid adding can separate out repeatedly, not cause wastage of material.
Beneficial effect
The beneficial effects of the present invention are more current quinolinic acid preparation method, the cupric oxide used in production process and activity
Carbon can be recycled, while taking potassium permanganate to replace traditional catalyst, reduce production cost, be economized on resources.
Specific embodiment
The technical problems to be solved by the invention are to provide a kind of preparation method of quinolinic acid.
Technical scheme includes oxidation-alkaline hydrolysis-acidifying.
Embodiment 1
First, aoxidize.
Cupric oxide and dilute sulfuric acid are pressed 1:1 mixing is put into reaction vessels, is heated to 40 DEG C.
After all being dissolved Deng cupric oxide, quinoline and 2% potassium permanganate are added, be stirred and heated to 97 DEG C.
Be added dropwise sodium chlorate solution, after the completion of be cooled to 30 DEG C.
Vacuum filtration obtains quinolinic acid copper filter cake, and filter cake is in neutrality using 30 DEG C of water washing to filtrate, after filtration cakes torrefaction
Obtain blue quinolinic acid copper products.
2nd, alkaline hydrolysis
Quinolinic acid copper products and alkali lye are heated with stirring to 70 DEG C, regulation PH is 10, after completion of the reaction, is cooled to 60 DEG C, while hot
Vacuum filtration, filter cake cupric oxide is used with being reclaimed after 50 DEG C of hot washes, and filtrate is quinoline acid sodium solution.
3rd, it is acidified
Quinoline acid sodium solution is added in reactor, 5 DEG C are cooled to, concentrated hydrochloric acid is added dropwise, stop being added dropwise when reaction solution PH is 3
Continue to stir, add activated carbon to be decolourized.Destainer acid adding can separate out quinolinic acid, after reaction terminates, vacuum filtration, filter cake
Quinolinic acid can obtain quinolinic acid with 30 DEG C of hot washes after drying.
Continue addition acid out when contained quinolinic acid can be produced next time again in filtrate to go out, the activated carbon of decolouring is after treatment
Can be continuing with.
Embodiment 2
First, aoxidize.
Cupric oxide and dilute sulfuric acid are pressed 1:1 mixing is put into reaction vessels, is heated to 45 DEG C.
After all being dissolved Deng cupric oxide, quinoline and 3% potassium permanganate are added, be stirred and heated to 100 DEG C.
Be added dropwise sodium chlorate solution, after the completion of be cooled to 35 DEG C.
Vacuum filtration obtains quinolinic acid copper filter cake, and filter cake is in neutrality using 35 DEG C of water washing to filtrate, after filtration cakes torrefaction
Obtain blue quinolinic acid copper products.
2nd, alkaline hydrolysis
Quinolinic acid copper products and alkali lye are heated with stirring to 70 DEG C, regulation PH is 10, after completion of the reaction, is cooled to 60 DEG C, while hot
Vacuum filtration, filter cake cupric oxide is used with being reclaimed after 50 DEG C of hot washes, and filtrate is quinoline acid sodium solution.
3rd, it is acidified
Quinoline acid sodium solution is added in reactor, 0 DEG C is cooled to, concentrated hydrochloric acid is added dropwise, stop being added dropwise when reaction solution PH is 3
Continue to stir, add activated carbon to be decolourized.Destainer acid adding can separate out quinolinic acid, after reaction terminates, vacuum filtration, filter cake
Quinolinic acid can obtain quinolinic acid with 35 DEG C of hot washes after drying.
Continue addition acid out when contained quinolinic acid can be produced next time again in filtrate to go out, the activated carbon of decolouring is after treatment
Can be continuing with.
Embodiment 3
First, aoxidize.
Cupric oxide and dilute sulfuric acid are pressed 1:1 mixing is put into reaction vessels, is heated to 50 DEG C.
After all being dissolved Deng cupric oxide, quinoline and 4% potassium permanganate are added, be stirred and heated to 103 DEG C.
Be added dropwise sodium chlorate solution, after the completion of be cooled to 40 DEG C.
Vacuum filtration obtains quinolinic acid copper filter cake, and filter cake is in neutrality using 40 DEG C of water washing to filtrate, after filtration cakes torrefaction
Obtain blue quinolinic acid copper products.
2nd, alkaline hydrolysis
Quinolinic acid copper products and alkali lye are heated with stirring to 70 DEG C, regulation PH is 10, after completion of the reaction, is cooled to 60 DEG C, while hot
Vacuum filtration, filter cake cupric oxide is used with being reclaimed after 50 DEG C of hot washes, and filtrate is quinoline acid sodium solution.
3rd, it is acidified
Quinoline acid sodium solution is added in reactor, 0 DEG C is cooled to, concentrated hydrochloric acid is added dropwise, stop being added dropwise when reaction solution PH is 3
Continue to stir, add activated carbon to be decolourized.Destainer acid adding can separate out quinolinic acid, after reaction terminates, vacuum filtration, filter cake
Quinolinic acid can obtain quinolinic acid with 40 DEG C of hot washes after drying.
Continue addition acid out when contained quinolinic acid can be produced next time again in filtrate to go out, the activated carbon of decolouring is after treatment
Can be continuing with.
Embodiment 4
The present embodiment is tested the quinolinic acid harvest rate prepared by embodiments of the invention 1 ~ 3.
The test result of the present embodiment is as follows：
Finally it should be noted that the above embodiments are merely illustrative of the technical solutions of the present invention rather than to the scope of the present invention
Limitation, although being elaborated to the present invention with reference to preferred embodiment, it will be understood by those within the art that, can
Modified or equivalent with to technical scheme, without deviating from the spirit and scope of technical solution of the present invention.
Claims (5)
1. a kind of preparation method of quinolinic acid, it is characterised in that the method is comprised the following steps：
1st step：Oxidation, generation quinolinic acid copper is aoxidized using quinoline, cupric oxide, sulfuric acid and sodium chlorate, while adding permanganic acid
It is catalyst to solve；
Second step：Alkaline hydrolysis, reacts 1 hour filtering cupric oxide under the conditions of PH10, and activated carbon alkalescence is decolourized；
Third step：Acidifying, PH3 is neutralized in alkaline destainer acid adding, plus activated carbon is acid decolourizes, acid destainer acid adding again
Product is separated out, white products are filtered to obtain.
2. the preparation method of a kind of quinolinic acid according to claim 1, it is characterised in that prepare quinoline using acid-base reaction
Acid.
3. the preparation method of a kind of quinolinic acid according to claim 1, it is characterised in that using cupric oxide for reaction in the middle of
Body.
4. the preparation method of a kind of quinolinic acid according to claim 1, it is characterised in that carried out to acid solution using activated carbon
Decolourize.
5. the preparation method of a kind of quinolinic acid according to claim 1, it is characterised in that add permanganic acid in oxidation stage
Potassium is catalyst.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201611058883.7A CN106831572A (en) | 2016-11-28 | 2016-11-28 | A kind of preparation method of quinolinic acid |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201611058883.7A CN106831572A (en) | 2016-11-28 | 2016-11-28 | A kind of preparation method of quinolinic acid |
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| CN106831572A true CN106831572A (en) | 2017-06-13 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997205A (en) * | 2018-09-13 | 2018-12-14 | 江苏师范大学 | A kind of synthetic method of 2,3- pyridinedicarboxylic acid |
| CN113603638A (en) * | 2021-08-11 | 2021-11-05 | 江西鑫海高分子材料有限公司 | Synthetic method of 2, 3-pyridinedicarboxylic acid |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4537971A (en) * | 1981-05-06 | 1985-08-27 | The Hilton-Davis Chemical Co. | Process for preparing quinolinic acid |
| CN102399182A (en) * | 2010-09-08 | 2012-04-04 | 鞍钢股份有限公司 | Process for producing quinolinic acid |
| CN104370808A (en) * | 2014-10-28 | 2015-02-25 | 常州大学 | Synthesis method of 2,3-dipicolinic acid |
-
2016
- 2016-11-28 CN CN201611058883.7A patent/CN106831572A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4537971A (en) * | 1981-05-06 | 1985-08-27 | The Hilton-Davis Chemical Co. | Process for preparing quinolinic acid |
| CN102399182A (en) * | 2010-09-08 | 2012-04-04 | 鞍钢股份有限公司 | Process for producing quinolinic acid |
| CN104370808A (en) * | 2014-10-28 | 2015-02-25 | 常州大学 | Synthesis method of 2,3-dipicolinic acid |
Non-Patent Citations (3)
| Title |
|---|
| 苏讯: "喹啉酸的催化合成研究", 《广东化工》 * |
| 邹星: "由喹啉制备2,3-吡啶二甲酸的方法研究", 《中国优秀博硕士学位论文全文数据库（硕士）工程科技I辑》 * |
| 霍俊超等: "《木材热解与活性炭生产》", 30 April 2003, 中国物资出版社 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108997205A (en) * | 2018-09-13 | 2018-12-14 | 江苏师范大学 | A kind of synthetic method of 2,3- pyridinedicarboxylic acid |
| CN113603638A (en) * | 2021-08-11 | 2021-11-05 | 江西鑫海高分子材料有限公司 | Synthetic method of 2, 3-pyridinedicarboxylic acid |
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Application publication date: 20170613 |