CN105384683A - 2-Methyl-pyridine and 4-methylpyridine production method - Google Patents
2-Methyl-pyridine and 4-methylpyridine production method Download PDFInfo
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- CN105384683A CN105384683A CN201510953953.4A CN201510953953A CN105384683A CN 105384683 A CN105384683 A CN 105384683A CN 201510953953 A CN201510953953 A CN 201510953953A CN 105384683 A CN105384683 A CN 105384683A
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- picoline
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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
- C07D213/06—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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Abstract
The present invention discloses a 2-methylpyridine and 4-methylpyridine production method, the steps are as follows: aniline as a raw material flows through a fixed bed reactor containing a molecular sieve catalyst, the reactor temperature and pressure are controlled, by the condensation reaction, the aniline is converted into a mixture reaction solution comprising diphenylamine, ammonia, 2-methylpyridine, 4-methylpyridine, water, acridine, 4-aminobiphenyl, and the like, the a low boiling point mixed fraction is obtained by multistage distillation of the mixture reaction solution, the low boiling point mixed fraction is dehydrated, the dehydrated mixture is dried, the dried mixture is distilled to obtain 2-methylpyridine and 4-methylpyridine according to different boiling points. The advantages are that: a feasible new 2-methylpyridine and 4-methylpyridine production method using the aniline as the raw material is provided, and use value and economic benefits of by-products generated by the conversion of the aniline into the diphenylamine are improved.
Description
Technical field
The present invention relates to extraordinary fine chemistry industry organic raw material and manufacture field, particularly relate to the production method of a kind of 2-picoline, 4-picoline.
Background technology
2-picoline, fusing point-70 DEG C, boiling point 128-129 DEG C, with water and ethanol miscible, being dissolved in most organic solvent, density 0.95, colourless liquid, is a kind of colourless oil liquid with strong unhappy pyridine smell.
4-picoline, fusing point 3.7 DEG C, boiling point 144.9 DEG C, water-soluble, ethanol and ether.There is light flowers and plants fragrance, colourless, inflammable, volatile, there is offending sweet taste.
Most common use:
1. for producing 2-vinyl pyridine, nitrogen fertilizer potentiating agent (N-Serve), long-acting sulfanilamide, anti-silicosis medicine, livestock insect repellent, poultry medication, organophosphorus toxinicide, local anesthetic, cathartic, the additive of light reaching the film agent, dyestuff intermediate and rubber accelerator etc.
2. for producing dyestuff, resin, agricultural chemicals, veterinary drug, rubber accelerator, light reaching the film agent additive etc.Pharmaceutically for the preparation of medicines such as Si Kani, Toldrin, Pyridine a-Aldoxime Methiodide, acetylcysteines.
3., for the synthesis of the chemical such as medicine, dyestuff, rubber, be also used as solvent, experiment reagent.
4. examine and determine cobalt, cyanate and iron.
5, for the synthesis of feature resin polyvinyl pyridine and 2-vinyl pyridine, and nylon cord tackiness agent---the butadiene styrene vinyl pyridine latex in radial is produced.
Common production method, pyridine and picoline reclaim usually from coking of coal by-product, and it is distributed in coke-oven gas, crude benzol and tar.The pyridines hydrate boiling point generally transferred to ammonium sulfate liquor from coal gas is all very low, and between 95-97 DEG C, reclaim in the light crude pyridine alkali obtained, 2-picoline is containing about 15%, and further rectifying can cut and obtain 2-picoline.Along with the expansion of pyridine and picoline purposes, synthesis method produces pyridine and picoline development, abroad about 95% pyridine and pyridine compounds and their synthesis method produce.Main synthesis method has Acetaldehyde, acetylene method, vinyl cyanide method etc.
It is technology leading in the world that aniline serialization catalyzes and synthesizes pentanoic, is also main flow production technology.Its by-product 2-picoline and 4-picoline generate simultaneously, and the transformation efficiency of 2-picoline, 4-picoline is aniline 0.1%-2%.But general distillation technology is difficult to them to be separated, forms single product supply market, generally make organic waste treatment, burner can be sprayed into fuel oil simultaneously do fuel.
Summary of the invention
In order to favourable Appropriate application aniline catalyzes and synthesizes the byproduct of pentanoic generation, decreasing pollution, improve the economic benefit of byproduct, the invention provides 2-picoline, production technique that 4-picoline is new, dewater in present method, dry and rectifying makes byproduct become single product to carry out collection and treatment, thus Each answers the purpose intended, the utilization ratio of raw material can be improved, increase the income of product in the production process of pentanoic.
The present invention realizes with following technical scheme, and 2-picoline, the production method that 4-picoline is new, comprise the steps:
S1. be raw material with aniline, under volume pump effect, flow through the fixed-bed reactor that molecular sieve catalyst is housed, control the temperature and pressure of reactor, described aniline changes into the mixture reaction liquid of the compositions such as pentanoic, ammonia, 2-picoline, 4-picoline, water, acridine, 4-phenylaniline through condensation reaction;
S2. described mixture reaction liquid is obtained lower boiling mixed fraction, unconverted aniline, medium boiling point mixed fraction, pentanoic and high boiling point residual night through multistage rectification, described lower boiling mixed fraction main component is 2-picoline, 4-picoline and water;
S3. described lower boiling mixed fraction and dewatering agent are pumped into dehydration tower dehydration with certain proportioning, control described dehydration tower temperature, make mixture gasification azeotropic, described gaseous mixture is through cooling, and separate lower layer of water through quantizer, upper strata is refluxed in described dehydration tower, be continuously pumped into described lower boiling mixed fraction, continuous stratification removes lower layer of water, and stop charging when liquid level in described dehydration tower reaches 1/3 height, dehydration stops heating to without water stratification;
S4. mixture in described dehydration tower is cooled to normal temperature, again described mixture is entered drying chamber dehydration, under the effect of pump, make mixture dehydration cycle dry, when karl Fischer instrument detects that moisture is less than 0.2% and terminates for dry, the described mixed solution main component after drying processed is benzene, 2-picoline and 4-picoline;
S5. the mixture pump after described drying and dehydrating is entered rectifying tower rectifying, according to the different boiling of described mixed solution main component, control the temperature of described rectifying tower, obtain benzene, 2-picoline and 4-picoline respectively through rectifying;
S6. remaining certain liquid level in rectifying tower, stops rectifying heating, continues the mixed solution after pumping into drying processed and carry out rectifying.
Concrete, molecular sieve catalyst described in S1 take aluminium sesquioxide as many micropores pentanoic special-purpose catalyst of main component.
Concrete, the temperature controlling described reactor in S1 is 280 DEG C-350 DEG C, and pressure is 1.6MPa-4.0MPa.
Preferably, the proportioning of the mixed fraction of lower boiling described in S3 and dewatering agent is 4:1.
Concrete, dewatering agent described in S3 is that boiling point is lower than 2-picoline, and can be separated with 4-picoline with 2-picoline by rectificating method, density ratio water is little, water insoluble, can with all organism of water azeotropic.
Preferably, described dewatering agent is benzene.
Concrete, the mode of control temperature described in S1, S2, S3 and S5 is steam jacket heating.
Concrete, siccative described in S4 be easily water suction formation binding substances or complex compound, does not form binding substances or complex compound, be insoluble to the inorganics of organic solvent class, be separated by simple filtration with organic mixture with benzene and 2-picoline and 4-picoline.
Preferably, described siccative is Calcium Chloride Powder Anhydrous, and described Calcium Chloride Powder Anhydrous cloth bag installs and hangs.
Further, the rectifying in S5 comprises the following steps:
When S51. controlling described rectifying tower top temperature for 70-128 DEG C, cut is benzene and a small amount of 2-picoline, collects through cooling, then is back to dehydration tower and repeats to do dewatering agent and use;
When S52. controlling described rectifying tower top temperature for 128-129 DEG C, cut is 2-picoline, collects through cooling;
When S53. controlling described rectifying tower top temperature for 130-144 DEG C, cut is 2-picoline and 4-methyl pyridine mixture, after cooling is collected, continues pump and enters rectifying tower rectifying.
When S54. controlling described rectifying tower top temperature for 144-146 DEG C, cut is 4-picoline, collects through cooling.
The invention has the beneficial effects as follows: provide one feasible take aniline as the novel method of raw material production 2-picoline and 4-picoline.Waste is turned waste into wealth, produces 5000 tons of pentanoic per year, the 2-picoline 80 tons of 99.5% and 4-picoline 20 tons can be greater than by by-product content simultaneously, improve utility value and the economic benefit of the byproduct produced when aniline is converted into pentanoic.
Accompanying drawing explanation
In order to be illustrated more clearly in technical scheme of the present invention, be briefly described to the accompanying drawing used required in embodiment or description of the prior art below, apparently, accompanying drawing in the following describes is only some embodiments of invention, for those of ordinary skill in the art, under the prerequisite not paying creative work, other accompanying drawing can also be obtained according to these accompanying drawings.
The production technological process that Fig. 1 is 2-picoline, 4-picoline is new.
Embodiment
For making the object, technical solutions and advantages of the present invention clearly, below in conjunction with accompanying drawing, the present invention is described in further detail.
In one embodiment, as shown in Figure 1, a kind of 2-picoline, the production technique that 4-picoline is new, comprise the steps:
S1. be raw material with aniline, flow through the fixed-bed reactor that molecular sieve catalyst is housed, the temperature controlling reactor is 280 DEG C-350 DEG C, pressure is 1.6MPa-4.0MPa, and aniline changes into the mixture reaction liquid of the compositions such as pentanoic, ammonia, 2-picoline, 4-picoline, water, acridine, 4-phenylaniline through condensation reaction;
S2. mixture reaction liquid is obtained lower boiling mixed fraction, unconverted aniline, medium boiling point mixed fraction, pentanoic and high boiling point residual night through multistage rectification, lower boiling mixed fraction main component is 2-picoline, 4-picoline and water;
S3. lower boiling mixed fraction and dewatering agent are pumped into dehydration tower dehydration with the proportioning of 4:1, control dehydration tower temperature, make mixture gasification azeotropic, gaseous mixture is through cooling, and separate lower layer of water through quantizer, upper strata is refluxed in described dehydration tower, be continuously pumped into lower boiling mixed fraction, continuous stratification removes lower layer of water, and stop charging when liquid level in dehydration tower reaches 1/3 height, dehydration stops heating to without water stratification;
S4. mixture in dehydration tower is cooled to normal temperature, again mixture is entered drying chamber dehydration, under the effect of pump, make mixture dehydration cycle dry, when karl Fischer instrument detects that moisture is less than 0.2% and terminates for dry, the mixed solution main component after drying processed is benzene, 2-picoline and 4-picoline;
S5. the mixture pump after drying and dehydrating is entered rectifying tower rectifying, according to the different boiling of mixed solution main component, control the temperature of rectifying tower, when rectifying tower top temperature is 70-128 DEG C, cut is benzene and a small amount of 2-picoline, collects through cooling, then is back to dehydration tower and repeats to do dewatering agent and use; When rectifying tower top temperature is 128-129 DEG C, cut is 2-picoline, collects through cooling, and sampling gas chromatographic analysis content is greater than 99.5%.; When rectifying tower top temperature is 130-144 DEG C, cut is 2-picoline and 4-methyl pyridine mixture, after cooling is collected, continues pump and enters rectifying tower rectifying.When rectifying tower top temperature is 144-146 DEG C, cut is 4-picoline, collects through cooling, and sampling gas chromatographic analysis content is greater than 99.5%;
S6. remaining certain liquid level in rectifying tower, stops rectifying heating, continues the mixed solution after pumping into drying processed and carry out rectifying;
Wherein S1 Middle molecule sieve catalyst take aluminium sesquioxide as many micropores pentanoic special-purpose catalyst of main component;
In S3, dewatering agent is benzene;
In S4, siccative is Calcium Chloride Powder Anhydrous, and Calcium Chloride Powder Anhydrous cloth bag installs and hangs;
In S1, S2, S3 and S5, control temperature mode is steam jacket heating.
Above disclosedly be only present pre-ferred embodiments, certainly can not limit the interest field of the present invention with this, therefore according to the equivalent variations that the claims in the present invention are done, still belong to the scope that the present invention is contained.
Claims (10)
1. a production method for 2-picoline, 4-picoline, is characterized in that, comprise the steps:
S1. be raw material with aniline, flow through the fixed-bed reactor that molecular sieve catalyst is housed, control the temperature and pressure of reactor, described aniline changes into the mixture reaction liquid of the compositions such as pentanoic, ammonia, 2-picoline, 4-picoline, water, acridine, 4-phenylaniline through condensation reaction;
S2. described mixture reaction liquid is obtained lower boiling mixed fraction, unconverted aniline, medium boiling point mixed fraction, pentanoic and high boiling point residual night through multistage rectification, described lower boiling mixed fraction main component is 2-picoline, 4-picoline and water;
S3. described lower boiling mixed fraction and dewatering agent are pumped into dehydration tower dehydration with certain proportioning, control described dehydration tower temperature, make mixture gasification azeotropic, gaseous mixture is through cooling, and separate lower layer of water through quantizer, upper strata is refluxed in described dehydration tower, be continuously pumped into described lower boiling mixed fraction, continuous stratification removes lower layer of water, and stop charging when liquid level in described dehydration tower reaches 1/3 height, dehydration stops heating to without water stratification;
S4. mixture in described dehydration tower is cooled to normal temperature, again described mixture is entered drying chamber dehydration, under the effect of pump, make mixture dehydration cycle dry, when karl Fischer instrument detects that moisture is less than 0.2% and terminates for dry, the described mixed solution main component after drying processed is benzene, 2-picoline and 4-picoline;
S5. the mixture pump after described drying and dehydrating is entered rectifying tower rectifying, according to the different boiling of described mixed solution main component, control the temperature of described rectifying tower, obtain benzene, 2-picoline and 4-picoline respectively through rectifying;
S6. remaining certain liquid level in rectifying tower, stops rectifying heating, continues the mixed solution after pumping into drying processed and carry out rectifying.
2. the production method of a kind of 2-picoline according to claim 1,4-picoline, is characterized in that, molecular sieve catalyst described in S1 take aluminium sesquioxide as many micropores pentanoic special-purpose catalyst of main component.
3. the production method of a kind of 2-picoline according to claim 1,4-picoline, is characterized in that, the temperature controlling described reactor in S1 is 280 DEG C-350 DEG C, and pressure is 1.6MPa-4.0MPa.
4. the production method of a kind of 2-picoline according to claim 1,4-picoline, is characterized in that, the proportioning of the mixed fraction of lower boiling described in S3 and dewatering agent is 4:1.
5. the production method of a kind of 2-picoline according to claim 1,4-picoline, it is characterized in that, dewatering agent described in S3 is that boiling point is lower than 2-picoline, can be separated with 4-picoline with 2-picoline by rectificating method, density ratio water is little, water insoluble, can with all organism of water azeotropic.
6. the production method of a kind of 2-picoline, 4-picoline according to claim 1 or 5, it is characterized in that, described dewatering agent is benzene.
7. the production method of a kind of 2-picoline according to claim 1,4-picoline, is characterized in that, the mode of control temperature described in S1, S2, S3 and S5 is steam jacket heating.
8. the production method of a kind of 2-picoline according to claim 1,4-picoline, it is characterized in that, siccative described in S4 is that easily water suction forms binding substances or complex compound, binding substances or complex compound is not formed with benzene and 2-picoline and 4-picoline, be insoluble to the inorganics of organic solvent class, can be separated with organic mixture by simple filtration.
9. a kind of 2-picoline according to claim 1 or 8, the production method of 4-picoline, it is characterized in that, described siccative is Calcium Chloride Powder Anhydrous, and described Calcium Chloride Powder Anhydrous cloth bag installs and hangs.
10. the production method of a kind of 2-picoline according to claim 1,4-picoline, it is characterized in that, the rectifying in S5 comprises the following steps:
When S51. controlling described rectifying tower top temperature for 70-128 DEG C, cut is benzene and a small amount of 2-picoline, collects through cooling, then is back to dehydration tower and repeats to do dewatering agent and use;
When S52. controlling described rectifying tower top temperature for 128-129 DEG C, cut is 2-picoline, collects through cooling;
When S53. controlling described rectifying tower top temperature for 130-144 DEG C, cut is 2-picoline and 4-methyl pyridine mixture, after cooling is collected, continues pump and enters rectifying tower rectifying.
When S54. controlling described rectifying tower top temperature for 144-146 DEG C, cut is 4-picoline, collects through cooling.
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| CN201510953953.4A CN105384683B (en) | 2015-12-17 | 2015-12-17 | A kind of 2 picoline, the production method of 4 picolines |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023071891A1 (en) * | 2021-10-31 | 2023-05-04 | 中国石油化工股份有限公司 | Method for selectively and continuously producing 2-methylpyridine and diphenylamine from aniline |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023071891A1 (en) * | 2021-10-31 | 2023-05-04 | 中国石油化工股份有限公司 | Method for selectively and continuously producing 2-methylpyridine and diphenylamine from aniline |
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