CN105153019A - 2-pyridinemethanol and synthetic method thereof - Google Patents
2-pyridinemethanol and synthetic method thereof Download PDFInfo
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- CN105153019A CN105153019A CN201510494815.4A CN201510494815A CN105153019A CN 105153019 A CN105153019 A CN 105153019A CN 201510494815 A CN201510494815 A CN 201510494815A CN 105153019 A CN105153019 A CN 105153019A
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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
- C07D213/04—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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses 2-pyridinemethanol and a synthetic method thereof. According to the method, 2-picoline and hydrogen peroxide are taken as raw materials, glacial acetic acid is taken as a solvent, the mixture has a reaction for 3-5 hours at the temperature of 70 DEG C-80 DEG C under the action of a catalyst, and 2-picoline nitrogen oxide is obtained after separation; 2-picoline nitrogen oxide and acetic anhydride react for 3-6 hours under the reflux condition, and acetic acid-2 pyridine methyl ester is obtained after separation; acetic acid-2 pyridine methyl ester is directly hydrolyzed under the alkali separating condition by sodium hydroxide, and a product 2-pyridinemethanol is obtained after separation. 2-pyridinemethanol and the synthetic method have the benefits as follows: the selectivity of process target products is high, material loss is low, the product content and the total yield can reach 98.5% and 65% respectively, and 2-pyridinemethanol is suitable for industrial mass production.
Description
Technical field
The invention belongs to fine chemistry industry to produce and technical field of pesticide, particularly relate to the product that a kind of synthetic method of 2-piconol and the method obtain.
Background technology
2-piconol, has another name called 2-4-hydroxymethylpiperidine, molecular formula C
6h
7nO, molecular weight 109.12, outward appearance is micro-yellow clarified liq, water-soluble and organic solvent, being soluble in chloroform and methylene dichloride, being mainly used in medicine intermediate, is NSAID (non-steroidal anti-inflammatory drug) piconol ibuprofen ester, the intermediate of the important drugs such as caccagogue bisacodyl and a kind of Cardiovarscular medicine newly developed, has huge development potentiality.
At present, China about the bibliographical information of research and development 2-piconol fewer, be mostly research and produce with reference to state's external mature technology.The producer that Some Domestic produces this product is also small-scale production, and product purity is not high, and product is mainly from developed country's imports such as America and Europes, and annual requirement is at about 1000 tons, and supply falls short of demand for product, has good market outlook.The synthetic method of 2-piconol, divides according to adopted starting raw material, and mainly contain halo method and the large route of shortening method two, wherein the severe reaction conditions of halo method, wayward, and production cost is high, is unsuitable for industrialized production; Shortening method reaction pressure is high, and catalyst levels is large, and long reaction time, yield is low, is not suitable for suitability for industrialized production.
Summary of the invention
The object of this invention is to provide a kind of synthetic method of 2-piconol, improve target product transformation efficiency, improve product content and total recovery, be suitable for suitability for industrialized production.
The object of the invention is to be achieved through the following technical solutions:
A synthetic method for 2-piconol, concrete steps are as follows:
(1) oxidizing reaction: at ambient pressure, mixes by a certain percentage by 2-picoline, glacial acetic acid, catalyzer, stirs after 20-40 minute, presses certain speed and drip 30%H at 70 ~ 80 DEG C
2o
2, reaction 3-6h, is cooled to normal temperature, obtains 2-methyl pyridine nitrogen oxide dilute solution;
(2) oxide compound is separated: by the catalyst filtration in 2-methyl pyridine nitrogen oxide dilute solution out, filtrate passes through underpressure distillation again, reclaim moisture and glacial acetic acid, mother liquor appropriate extraction agent extraction, separatory, precipitation, obtain 2-methyl pyridine nitrogen oxide;
(3) acidylate rearrangement reaction: 2-methyl pyridine nitrogen oxide is joined in aceticanhydride, under reflux conditions react 3-6h, revolve steaming after reaction terminates and slough glacial acetic acid and aceticanhydride, mother liquor pH adjusting agent adjusts pH to certain value, filter, with the extraction of appropriate extraction agent, separatory, precipitation, obtain acetic acid-2-picolyl;
(4) hydrolysis reaction: add in basic solvent by acetic acid-2-picolyl, reacts 2 ~ 4 hours under reflux conditions, filters, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation after being down to normal temperature.
Preferably, the catalyzer described in step (1) is molybdic oxide or aluminum oxide, and wherein catalyst levels is 0.5% ~ 1.2% of 2-picoline quality, the catalyzer molybdic oxide (MoO selected
3) there is special structure---by atoms metal Mo at center, Sauerstoffatom is at [the MoO of the arm of angle
6] octahedron is basic structural unit, corner-sharing, forms chain and connects, every two similar chains are connected to form the MoO of stratiform in limit altogether
3stoichiometric structure, depends on van der Waals interaction to interlock packing arrangement between layers, is applicable to very much the embedding of other small molecules or ion.This special laminate structure makes molybdic oxide have good catalytic performance.The alumina catalyst selected, is generally loose porous shape, specific surface area is large, porosity is high, Active sites is many, for reactant provides contact interface to react, has unique catalytic perfomance.The association rate of 2-picoline and hydrogen peroxide can be accelerated after catalyzer adds system, greatly improve the transformation efficiency of 2-methyl pyridine nitrogen oxide, and then improve the yield of target product.
Preferably, H described in step (1)
2o
2omnidistance dropping, wherein 2-picoline and H
2o
2mol ratio: 1:1.1 ~ 1.8.
Preferably, pH adjusting agent described in step (3) is powder sodium carbonate or salt of wormwood, adjust ph is 10 ~ 12, the danger of selecting carbonate to not only avoid highly basic to corrode people, cause the shortcomings such as other decomposition product, and carbonate is gentleer for the control ratio of pH, be easier to the adjustment of system pH.
Preferably, step (2), (3), the extraction agent described in (4) are any one or combination above between two in methylene dichloride, ethylene dichloride, trichloromethane, toluene, extraction liquid in this external step (2), (3), (4) and the volume ratio of extraction agent are 1:1 ~ 1:3, the catalyzer the selected feature that not only concrete extraction efficiency is high, and its boiling point is lower, energy consumption required during recovery is also lower.
Preferably, the basic solvent described in step (3) is the sodium hydroxide solution of 20%, and the mol ratio of acetic acid-2-picolyl and sodium hydroxide is 1:1.2 ~ 2.0, and acetic acid-2-picolyl can be fully hydrolyzed.
Another object of the present invention is to provide the 2-piconol that a kind of aforesaid method obtains.
The invention has the beneficial effects as follows:
1) the method using 2-picoline be raw material, glacial acetic acid as solvent, enormously simplify 2-piconol synthesis production stage, simple, convenient, decrease the discharge of waste water, realize the close friend to environment;
2) select molybdic oxide or aluminum oxide as catalyzer, price is relatively cheap, has saved production cost; Not easily produce deactivation phenomenom, long service life, excellent catalytic effect, substantially increase the transformation efficiency of 2-methyl pyridine nitrogen oxide, product assay and total recovery bring up to 98.5% and 65% respectively, are suitable for industrialized production;
Embodiment
Below in conjunction with embodiment, the present invention is further described.
Embodiment 1
In the enamel glass reactor of 3000L, add 310Kg2-picoline, 930kg glacial acetic acid, 3.0kg molybdic oxide, stir after 20-40 minute, at 75 DEG C of temperature, drip 753.7Kg30%H2O2, reaction 3-5h, is down to normal temperature, filtering catalyst, filtrate is again by underpressure distillation, and reclaim moisture and glacial acetic acid, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain 2-methyl pyridine nitrogen oxide.2-methyl pyridine nitrogen oxide is added 862.5Kg aceticanhydride, under reflux conditions react 3-6h, revolve steaming and slough glacial acetic acid and aceticanhydride after reaction terminates, mother liquor powder salt of wormwood adjusts pH to 10, filter, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain acetic acid-2-picolyl.Acetic acid-2-picolyl is added the NaOH solution of 500Kg20%, react 2 ~ 4 hours under reflux conditions, filter after being down to normal temperature, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation, yield is 65.4%.
Embodiment 2
In the enamel glass reactor of 3000L, add 310Kg2-picoline, 930kg glacial acetic acid, 1.6kg molybdic oxide, stir after 20-40 minute, at 75 DEG C of temperature, drip 753.7Kg30%H2O2, reaction 3-5h, is down to normal temperature, filtering catalyst, filtrate is again by underpressure distillation, and reclaim moisture and glacial acetic acid, the extraction of mother liquor 600L ethylene dichloride, separatory, precipitation obtain 2-methyl pyridine nitrogen oxide.2-methyl pyridine nitrogen oxide is added 862.5Kg aceticanhydride, under reflux conditions react 3-6h, revolve steaming and slough glacial acetic acid and aceticanhydride after reaction terminates, mother liquor powder salt of wormwood adjusts pH to 10, filter, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain acetic acid-2-picolyl.Acetic acid-2-picolyl is added the NaOH solution of 500Kg20%, react 2 ~ 4 hours under reflux conditions, filter after being down to normal temperature, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation, yield is 64.7%.
Embodiment 3
In the enamel glass reactor of 3000L, add 310Kg2-picoline, 1240kg glacial acetic acid, 3.0kg molybdic oxide, stir after 20-40 minute, at 75 DEG C of temperature, drip 753.7Kg30%H2O2, reaction 3-5h, is down to normal temperature, filtering catalyst, filtrate is again by underpressure distillation, and reclaim moisture and glacial acetic acid, mother liquor 600L chloroform extraction, separatory, precipitation obtain 2-methyl pyridine nitrogen oxide.2-methyl pyridine nitrogen oxide is added 862.5Kg aceticanhydride, under reflux conditions react 3-6h, revolve steaming and slough glacial acetic acid and aceticanhydride after reaction terminates, mother liquor powder salt of wormwood adjusts pH to 10, filter, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain acetic acid-2-picolyl.Acetic acid-2-picolyl is added the NaOH solution of 500Kg20%, react 2 ~ 4 hours under reflux conditions, filter after being down to normal temperature, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation, yield is 68.5%.
Embodiment 4
In the enamel glass reactor of 3000L, add 310Kg2-picoline, 1240kg glacial acetic acid, 3.0kg molybdic oxide, stir after 20-40 minute, at 75 DEG C of temperature, drip 1133.3Kg30%H2O2, reaction 3-5h, is down to normal temperature, filtering catalyst, filtrate is again by underpressure distillation, and reclaim moisture and glacial acetic acid, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain 2-methyl pyridine nitrogen oxide.2-methyl pyridine nitrogen oxide is added 862.5Kg aceticanhydride, under reflux conditions react 3-6h, revolve steaming and slough glacial acetic acid and aceticanhydride after reaction terminates, mother liquor powder salt of wormwood adjusts pH to 10, filter, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain acetic acid-2-picolyl.Acetic acid-2-picolyl is added the NaOH solution of 500Kg20%, react 2 ~ 4 hours under reflux conditions, filter after being down to normal temperature, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation, yield is 67.9%.
Embodiment 5
In the enamel glass reactor of 3000L, add 310Kg2-picoline, 1240kg glacial acetic acid, 3.0kg molybdic oxide, stir after 20-40 minute, at 75 DEG C of temperature, drip 753.7Kg30%H2O2, reaction 3-5h, is down to normal temperature, filtering catalyst, filtrate is again by underpressure distillation, and reclaim moisture and glacial acetic acid, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain 2-methyl pyridine nitrogen oxide.2-methyl pyridine nitrogen oxide is added 680Kg aceticanhydride, under reflux conditions react 3-6h, revolve steaming and slough glacial acetic acid and aceticanhydride after reaction terminates, mother liquor powder salt of wormwood adjusts pH to 10, filter, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain acetic acid-2-picolyl.Acetic acid-2-picolyl is added the NaOH solution of 500Kg20%, react 2 ~ 4 hours under reflux conditions, filter after being down to normal temperature, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation, yield is 65.9%.
Embodiment 6
In the enamel glass reactor of 3000L, add 310Kg2-picoline, 1240kg glacial acetic acid, 3.0kg molybdic oxide, stir after 20-40 minute, at 75 DEG C of temperature, drip 753.7Kg30%H2O2, reaction 3-5h, is down to normal temperature, filtering catalyst, filtrate is again by underpressure distillation, and reclaim moisture and glacial acetic acid, the extraction of mother liquor 600L ethylene dichloride, separatory, precipitation obtain 2-methyl pyridine nitrogen oxide.2-methyl pyridine nitrogen oxide is added 680Kg aceticanhydride, under reflux conditions react 3-6h, revolve steaming and slough glacial acetic acid and aceticanhydride after reaction terminates, mother liquor powder salt of wormwood adjusts pH to 10, filter, mother liquor 600L dichloromethane extraction, separatory, precipitation obtain acetic acid-2-picolyl.Acetic acid-2-picolyl is added the NaOH solution of 400Kg20%, react 2 ~ 4 hours under reflux conditions, filter after being down to normal temperature, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation, yield is 64.7%.
Claims (7)
1. a synthetic method for 2-piconol, is characterized in that, concrete steps are as follows:
(1) oxidizing reaction: at ambient pressure, mixes by a certain percentage by 2-picoline, glacial acetic acid, catalyzer, stirs after 20-40 minute, presses certain speed and drip 30%H at 70 ~ 80 DEG C
2o
2, reaction 3-6h, is cooled to normal temperature, obtains 2-methyl pyridine nitrogen oxide dilute solution;
(2) oxide compound is separated: by the catalyst filtration in 2-methyl pyridine nitrogen oxide dilute solution out, filtrate passes through underpressure distillation again, reclaim moisture and glacial acetic acid, mother liquor appropriate extraction agent extraction, separatory, precipitation, obtain 2-methyl pyridine nitrogen oxide;
(3) acidylate rearrangement reaction: 2-methyl pyridine nitrogen oxide is joined in aceticanhydride, under reflux conditions react 3-6h, revolve steaming after reaction terminates and slough glacial acetic acid and aceticanhydride, mother liquor pH adjusting agent adjusts pH to certain value, filter, with the extraction of appropriate extraction agent, separatory, precipitation, obtain acetic acid-2-picolyl;
(4) hydrolysis reaction: add in basic solvent by acetic acid-2-picolyl, reacts 2 ~ 4 hours under reflux conditions, filters, obtain 2-piconol with the extraction of appropriate extraction agent, separatory, precipitation after being down to normal temperature.
2. method according to claim 1, is characterized in that, the catalyzer described in step (1) is molybdic oxide or aluminum oxide, and wherein catalyst levels is 0.5% ~ 1.2% of 2-picoline quality.
3. method according to claim 1, is characterized in that, H described in step (1)
2o
2omnidistance dropping, wherein 2-picoline and H
2o
2mol ratio: 1:1.1 ~ 1.8.
4. method according to claim 1, is characterized in that, the pH adjusting agent described in step (3) is powder sodium carbonate or salt of wormwood, and adjust ph is 10 ~ 12.
5. method according to claim 1, it is characterized in that, step (2), (3), the extraction agent described in (4) are any one or combination above between two in methylene dichloride, ethylene dichloride, trichloromethane, toluene, and the volume ratio of extraction liquid and extraction agent is 1:1 ~ 1:3.
6. method according to claim 1, is characterized in that, the basic solvent described in step (3) is the sodium hydroxide solution of 20%, and the mol ratio of acetic acid-2-picolyl and sodium hydroxide is 1:1.2 ~ 2.0.
7. the 2-piconol that method obtains according to any one of claim 1 to 6.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107043348A (en) * | 2017-06-26 | 2017-08-15 | 刘瑞海 | A kind of synthetic method of 4 pyridinemethanol |
| CN107162960A (en) * | 2017-06-08 | 2017-09-15 | 安徽星宇化工有限公司 | The synthetic method of 2 pyridinemethanols |
| CN107162961A (en) * | 2017-06-25 | 2017-09-15 | 刘瑞海 | A kind of synthetic method of 3 pyridinemethanol |
| CN107286079A (en) * | 2017-06-25 | 2017-10-24 | 刘瑞海 | A kind of synthetic method of 2 pyridinemethanol |
| CN107286080A (en) * | 2017-06-25 | 2017-10-24 | 刘瑞海 | A kind of synthetic method of 2 pyridine carboxaldehyde |
| CN107311917A (en) * | 2017-06-25 | 2017-11-03 | 刘瑞海 | A kind of synthetic method of 3 pyridine carboxaldehyde |
| CN107311918A (en) * | 2017-06-26 | 2017-11-03 | 刘瑞海 | A kind of synthetic method of 4 pyridine carboxaldehyde |
| CN108164460A (en) * | 2018-01-12 | 2018-06-15 | 清华大学 | A kind of method for preparing 3- methylpyridine N oxides |
| CN108191745A (en) * | 2018-01-08 | 2018-06-22 | 滁州学院 | The preparation method of 2- methylol -3,4- dimethoxy-pyridines |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107162960A (en) * | 2017-06-08 | 2017-09-15 | 安徽星宇化工有限公司 | The synthetic method of 2 pyridinemethanols |
| CN107162960B (en) * | 2017-06-08 | 2019-10-22 | 安徽星宇化工有限公司 | The synthetic method of 2- pyridinemethanol |
| CN107162961A (en) * | 2017-06-25 | 2017-09-15 | 刘瑞海 | A kind of synthetic method of 3 pyridinemethanol |
| CN107286079A (en) * | 2017-06-25 | 2017-10-24 | 刘瑞海 | A kind of synthetic method of 2 pyridinemethanol |
| CN107286080A (en) * | 2017-06-25 | 2017-10-24 | 刘瑞海 | A kind of synthetic method of 2 pyridine carboxaldehyde |
| CN107311917A (en) * | 2017-06-25 | 2017-11-03 | 刘瑞海 | A kind of synthetic method of 3 pyridine carboxaldehyde |
| CN107043348A (en) * | 2017-06-26 | 2017-08-15 | 刘瑞海 | A kind of synthetic method of 4 pyridinemethanol |
| CN107311918A (en) * | 2017-06-26 | 2017-11-03 | 刘瑞海 | A kind of synthetic method of 4 pyridine carboxaldehyde |
| CN108191745A (en) * | 2018-01-08 | 2018-06-22 | 滁州学院 | The preparation method of 2- methylol -3,4- dimethoxy-pyridines |
| CN108164460A (en) * | 2018-01-12 | 2018-06-15 | 清华大学 | A kind of method for preparing 3- methylpyridine N oxides |
| CN108164460B (en) * | 2018-01-12 | 2020-09-22 | 清华大学 | Method for preparing 3-methylpyridine-N-oxide |
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Application publication date: 20151216 |