CN102863375A - Method for synthesizing and preparing 2-vinyl pyridine - Google Patents
Method for synthesizing and preparing 2-vinyl pyridine Download PDFInfo
- Publication number
- CN102863375A CN102863375A CN2011101916401A CN201110191640A CN102863375A CN 102863375 A CN102863375 A CN 102863375A CN 2011101916401 A CN2011101916401 A CN 2011101916401A CN 201110191640 A CN201110191640 A CN 201110191640A CN 102863375 A CN102863375 A CN 102863375A
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- CN
- China
- Prior art keywords
- vinyl pyridine
- pyridine
- solution
- preparing
- sodium hydroxide
- 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.)
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- KGIGUEBEKRSTEW-UHFFFAOYSA-N 2-vinylpyridine Chemical compound C=CC1=CC=CC=N1 KGIGUEBEKRSTEW-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims abstract description 11
- 230000002194 synthesizing effect Effects 0.000 title abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 45
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 31
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000002994 raw material Substances 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 6
- 238000010189 synthetic method Methods 0.000 claims description 8
- 239000007788 liquid Substances 0.000 claims description 5
- 239000012043 crude product Substances 0.000 abstract description 11
- 238000005406 washing Methods 0.000 abstract description 9
- BXGYBSJAZFGIPX-UHFFFAOYSA-N 2-pyridin-2-ylethanol Chemical compound OCCC1=CC=CC=N1 BXGYBSJAZFGIPX-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000047 product Substances 0.000 abstract description 6
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 abstract description 2
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009924 canning Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019606 astringent taste Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
The invention relates to a method for synthesizing and preparing 2-vinyl pyridine by synthesizing 2-methyl pyridine and formaldehyde, which comprises the following steps of: adding the raw materials 2-methyl pyridine and formaldehyde (36%) into a high pressure reactor according to the weight ratio of 1: 0.03, stirring and heating for reaction to obtain 2-hydroxyethyl pyridine solution; slowly adding the obtained 2-hydroxyethyl pyridine solution into a dehydration kettle filled with sodium hydroxide (50%) solution through a measuring tank (1 ton) to obtain the crude product 2-vinyl pyridine; and sending the obtained crude product 2-vinyl pyridine into a washing kettle through a pipeline, adding sodium hydroxide (95%) solution into the washing kettle, and carrying out cut fraction on the crude product 2-vinyl pyridine which is separated by washing to obtain the 2-vinyl pyridine with the gas phase chromatography test content of more than 98.5%. The method adopts novel catalyst, so that the unit comprehensive energy consumption is reduced by 20%; the production process is automatically controlled, the product purity is greatly improved, and the product content reaches up to more than 98.5%; and the whole process route is clean and environment-friendly.
Description
Technical field
The present invention relates to the preparation method of 2-vinyl pyridine, specifically provide a kind of with 2-picoline and the synthetic method for preparing the 2-vinyl pyridine of formaldehyde.
Background technology
What the operational path take the 2-picoline as raw material production 2-vinyl pyridine in the prior art adopted is two step method production, periodical operation, the temperature of this arts demand is relatively high, the pressure that reacts required is relatively large, the catalyzer preparation is complicated, cut contaminate environment, therefore be badly in need of new processing method and solve the deficiency that existing technique exists.
Summary of the invention
The object of the invention is to for existent defect in the above-mentioned prior art with not enough, provide a kind of and synthesize the method for preparing the 2-vinyl pyridine take 2-picoline and formaldehyde as raw material take sodium hydroxide as catalyzer.
The objective of the invention is to be achieved through the following technical solutions:
A kind of with 2-picoline and the synthetic method for preparing the 2-vinyl pyridine of formaldehyde, comprise the steps: A: the weight proportion of raw material 2-picoline, formaldehyde (36%) is added in the autoclave in 1: 0.03 ratio, stir temperature reaction, pressure is 0.5Mpa, temperature of reaction 130-160 ℃, react after 1 hour, be transported to and accept in the still, obtain 2-hydroxyethyl pyridine solution; B: by resulting 2-hydroxyethyl pyridine solution, slowly add in the dehydrating kettle that adds sodium hydroxide (50%) solution (100 kilograms) through test tank (1 ton), temperature keeps 90 ℃, reacted 5 hours, obtain crude product 2-vinyl pyridine, crude product 2-vinyl pyridine is delivered in the washing kettle through pipeline, added sodium hydroxide (95%) solution (75 kilograms), wash and separated 5 hours; C: the crude product 2-vinyl pyridine after the washing separation, deliver to through pipeline and to carry out cut in the rectifying still, keep 90 ℃ of temperature, rectifying 4 hours, sample examination in the rectifying, the underproof crude product of first half is put into again dehydration washing of receiving tank preparation, and qualified product are directly put into the finished pot canning and warehousing, get 2-vinyl pyridine gas chromatography and survey content more than 98.5%.
Process parameters range
1, raw material weight proportioning: 2-picoline: formaldehyde (36%)=1: 0.03.
2, catalyzer: sodium hydroxide (50%) solution, sodium hydroxide (95%) solution.
3,2-picoline: purity 〉=99%
4, reaction conditions: 90 ℃-160 ℃ of temperature, pressure is 0.5Mpa.
5, this technique gets finished product: colourless transparent liquid, content 〉=98%, moisture content≤0.5%.
The main raw material characteristic index
(1) 2-picoline: molecular formula: C
6H
7N, molecular weight: 93.13, content: 〉=99%, fusing point :-64 ℃, boiling point: 129.5 ℃, solvability: be dissolved in acetone, ether, miscible with water and ethanol, have the colourless oil liquid of pyridine smell.
(2) formaldehyde: molecular formula: CH
2O, HCHO, molecular weight: 30.03, boiling point :-19.5 ℃, fusing point :-118 ℃, a kind of colourless, the gas of intense stimulus smell is arranged, soluble in water, pure and mild ether, formaldehyde are gaseous state at normal temperatures, soluble in water and ethanol usually occurs with aqueous solution form.
(3) sodium hydroxide: chemical formula: NaOH, molecular weight: 40.01, water-soluble: very easily molten, boiling point: 1390 ℃, alkali dissociation constant (Kb)=3.0, NaOH is a kind of common important highly basic, its liquid is a kind of colourless, and the liquid of astringent taste and soapy feeling is arranged.
Beneficial effect of the present invention: the one, the reactor low-temp low-pressure, safety performance is high, effectively assurance device safety and stability, for a long time continuous operation; The 2nd, energy consumption is low, highlights cost advantage, owing to having adopted new catalyst, main raw material(s) descends 15%, and the unit comprehensive energy consumption has reduced by 20%; The 3rd, technical process is simplified, and production process realizes automatization control, and product purity increases substantially, and content reaches more than 98.5%; The 4th, integrated artistic route clean environment firendly, the operation of production process flowing water does not expose contact, does not produce waste water, waste gas, meets the requirement of clean environment firendly.
Embodiment
The present invention is further described below in conjunction with specific embodiment.
Embodiment
The weight proportion of getting raw material 2-picoline, formaldehyde (36%) adds in the autoclave in 1: 0.03 ratio, stirs, and is warming up to gradually 160 ℃, keep pressure 0.5Mpa, the reaction timing is after 1 hour, be transported to and accept in the still, obtain 2 one hydroxyethyl pyridine solutions; By resulting 2-hydroxyethyl pyridine solution, slowly add in the dehydrating kettle that adds sodium hydroxide (50%) solution (100 kilograms) through test tank (1 ton), temperature keeps 90 ℃, reacted 5 hours, obtain crude product 2-vinyl pyridine, crude product 2-vinyl pyridine is delivered in the washing kettle through pipeline, added sodium hydroxide (95%) solution (75 kilograms), wash and separated 5 hours; The crude product 2-vinyl pyridine after the washing separation, deliver to through pipeline and to carry out cut in the rectifying still, keep 90 ℃ of temperature, rectifying 4 hours, sample examination in the rectifying, the underproof crude product of first half is put into again dehydration washing of receiving tank preparation, and qualified product are directly put into the finished pot canning and warehousing, get 2-vinyl pyridine gas chromatography and survey content more than 98.5%.
Claims (5)
1. a synthetic method for preparing the 2-vinyl pyridine is characterized in that preparing 2-vinyl pyridine as raw material take sodium hydroxide as catalyzer synthesizes take 2-picoline and formaldehyde.
2. a kind of synthetic method for preparing the 2-vinyl pyridine according to claim 1, the weight proportion of raw material 2-picoline, formaldehyde (36%) 1: 0.03.
3. a kind of synthetic method for preparing the 2-vinyl pyridine according to claim 1, catalyzer: sodium hydroxide (50%) solution, sodium hydroxide (95%) solution.
4. a kind of synthetic method for preparing the 2-vinyl pyridine according to claim 1, the 2-picoline: purity 〉=99%, reaction conditions: 90 ℃-160 ℃ of temperature, pressure is 0.5Mpa.
5. a kind of synthetic method for preparing the 2-vinyl pyridine according to claim 1, this technique gets finished product: colourless transparent liquid, content 〉=98%, moisture content≤0.5%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101916401A CN102863375A (en) | 2011-07-03 | 2011-07-03 | Method for synthesizing and preparing 2-vinyl pyridine |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011101916401A CN102863375A (en) | 2011-07-03 | 2011-07-03 | Method for synthesizing and preparing 2-vinyl pyridine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102863375A true CN102863375A (en) | 2013-01-09 |
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| CN2011101916401A Pending CN102863375A (en) | 2011-07-03 | 2011-07-03 | Method for synthesizing and preparing 2-vinyl pyridine |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104109114A (en) * | 2014-07-17 | 2014-10-22 | 东南大学 | High-efficiency environment-friendly preparation method of 2-hydroxyethylpyridine |
| CN106699641A (en) * | 2015-11-14 | 2017-05-24 | 宁夏际华环境安全科技有限公司 | Production process for 4-vinylpyridine |
| CN108043460A (en) * | 2017-11-21 | 2018-05-18 | 江苏亚泰化工有限公司 | A kind of 2- phenylbenzothiazols ring metal Co catalysts and its synthetic method |
| CN111533683A (en) * | 2020-05-27 | 2020-08-14 | 鹤壁市赛科化工有限公司 | Method and device for preparing vinylpyridine by continuously dehydrating hydroxyethylpyridine |
| CN118577209A (en) * | 2024-08-01 | 2024-09-03 | 淄博奥固特科技有限公司 | A kind of synthesis process of high-yield 2-vinylpyridine |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86103091A (en) * | 1986-05-09 | 1987-11-18 | 中国科学院化学研究所 | Synthetic process of vinyl pyridine at atmomspheric pressure |
| US6727365B1 (en) * | 2002-10-31 | 2004-04-27 | Shivanand Janardan Kulkarni | Process for the preparation of vinylpyridine from picoline over modified zeolites |
| CN1580045A (en) * | 2004-05-18 | 2005-02-16 | 淄博张店东方化学股份有限公司 | Process for large-scale preparation of 2-vinyl pyridine |
-
2011
- 2011-07-03 CN CN2011101916401A patent/CN102863375A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN86103091A (en) * | 1986-05-09 | 1987-11-18 | 中国科学院化学研究所 | Synthetic process of vinyl pyridine at atmomspheric pressure |
| US6727365B1 (en) * | 2002-10-31 | 2004-04-27 | Shivanand Janardan Kulkarni | Process for the preparation of vinylpyridine from picoline over modified zeolites |
| CN1580045A (en) * | 2004-05-18 | 2005-02-16 | 淄博张店东方化学股份有限公司 | Process for large-scale preparation of 2-vinyl pyridine |
Non-Patent Citations (2)
| Title |
|---|
| 许建帼，等: "2-乙烯基吡啶的合成方法", 《天津化工》, vol. 18, no. 6, 30 November 2004 (2004-11-30) * |
| 赵鹬，等: "2-甲基吡啶合成2-乙烯基吡啶", 《南京工业大学学报》, vol. 28, no. 5, 30 September 2006 (2006-09-30), pages 37 - 41 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104109114A (en) * | 2014-07-17 | 2014-10-22 | 东南大学 | High-efficiency environment-friendly preparation method of 2-hydroxyethylpyridine |
| CN104109114B (en) * | 2014-07-17 | 2016-08-24 | 东南大学 | A kind of preparation method of the 2-ethoxy pyridine of high-efficiency environment friendly |
| CN106699641A (en) * | 2015-11-14 | 2017-05-24 | 宁夏际华环境安全科技有限公司 | Production process for 4-vinylpyridine |
| CN108043460A (en) * | 2017-11-21 | 2018-05-18 | 江苏亚泰化工有限公司 | A kind of 2- phenylbenzothiazols ring metal Co catalysts and its synthetic method |
| CN108043460B (en) * | 2017-11-21 | 2019-11-26 | 江苏亚泰化工有限公司 | A kind of 2- phenylbenzothiazol ring metal Co catalysts and its synthetic method |
| CN111533683A (en) * | 2020-05-27 | 2020-08-14 | 鹤壁市赛科化工有限公司 | Method and device for preparing vinylpyridine by continuously dehydrating hydroxyethylpyridine |
| CN111533683B (en) * | 2020-05-27 | 2023-05-09 | 鹤壁市赛科化工有限公司 | Method and device for preparing vinyl pyridine by continuous dehydration of hydroxyethyl pyridine |
| CN118577209A (en) * | 2024-08-01 | 2024-09-03 | 淄博奥固特科技有限公司 | A kind of synthesis process of high-yield 2-vinylpyridine |
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Application publication date: 20130109 |