CN101987831A - Process for preparing of n-methyl pyrrolidone - Google Patents
Process for preparing of n-methyl pyrrolidone Download PDFInfo
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- CN101987831A CN101987831A CN201010228714XA CN201010228714A CN101987831A CN 101987831 A CN101987831 A CN 101987831A CN 201010228714X A CN201010228714X A CN 201010228714XA CN 201010228714 A CN201010228714 A CN 201010228714A CN 101987831 A CN101987831 A CN 101987831A
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- monomethylamine
- methyl pyrrolidone
- preparing
- butyrolactone
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/04—Formation or introduction of functional groups containing oxygen of ether, acetal or ketal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B43/00—Formation or introduction of functional groups containing nitrogen
- C07B43/04—Formation or introduction of functional groups containing nitrogen of amino groups
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Abstract
The present invention provides a process for preparing of N-methyl pyrrolidone, and more particularly to a following process for preparing of N-methyl pyrrolidone, wherein, monomethylamine (MMA) solution and gamma-butyrolactone (GBL) are provided into a reactor. The N-methyl pyrrolidone obtained through the reaction between the monomethylamine and the gamma-butyrolactone is separated from water. The separated water is mixed with the monomethylamine for preparing the monomethylamine solution, and then the monomethylamine solution is introduced into the reactor. The provided process for preparing of N-methyl pyrrolidone is advantageous in that: the water generated by the reaction between the monomethylamine and the gamma-butyrolactone is collected for preparing the monomethylamine solution and circulates into the reactor, thereby saving energy and causes easy separation of the N-methyl pyrrolidone product.
Description
Technical field
The present invention relates to prepare the method for N-Methyl pyrrolidone (NMP), more specifically, relate to the following method for preparing N-Methyl pyrrolidone, wherein, Monomethylamine (MMA) aqueous solution and gamma-butyrolactone (GBL) are provided in reactor, N-Methyl pyrrolidone that will be obtained by the reaction of Monomethylamine and gamma-butyrolactone and water sepn and the isolating water of institute mixed with Monomethylamine to prepare monomethylamine aqueous solution it is drawn be back in the reactor then.
Background technology
N-Methyl pyrrolidone is to have low viscosity and excellent stable on heating colourless, nonpoisonous organic solvent.As chemically stable high polar solvent, it is very useful in needing the various chemical reactions of inert media.Along with the increasingly stringent of environmental legislation, environmental friendliness, nontoxic N-Methyl pyrrolidone are syntheticly made with processing, paint at polymkeric substance, the metallic surface cleaning, that medicine is synthetic is also more and more with purifying, semi-conductor and Application for Field such as electron device processing or lithium cell manufacturing.
Industrial, N-Methyl pyrrolidone is by the dehydration of Monomethylamine and gamma-butyrolactone prepares under the catalyzer using or do not use.
As not using the Preparation of catalysts method, following method was disclosed: gamma-butyrolactone and Monomethylamine are reacted 4 hours with preparation N-Methyl pyrrolidone (yield: [J.Amer.Chem.Soc. 90%～93%) in 280 ℃ in batch reactor, 71 (1949), 896].In addition, disclose for Japanese patent laid-open 1-190667 number a kind of by with gamma-butyrolactone, water and Monomethylamine in the high pressure batch reactor under 240 ℃～265 ℃ and 50atm reaction prepared the method (yield: 94.3%) of methyl-2-pyrrolidone in 3 hours.
As using the Preparation of catalysts method, following method was disclosed: with gamma-butyrolactone and Monomethylamine in the presence of the y-type zeolite catalyzer of Copper Ion Exchange in 280 ℃ and normal pressure successive reaction with preparation N-Methyl pyrrolidone (yield: [Bull.Chem.Soc.Japan 98%), 50 (10) (1977), 2517].In addition, also disclose following method, wherein, prepared N-Methyl pyrrolidone (yield: [J.Org.Chem. 98.2%) 300 ℃ successive reaction by gamma-butyrolactone and the Monomethylamine ZSM-5 zeolite catalyst by using the chromium ion exchange, 50 (1994), 3998].In addition, the Japanese Patent spy opens clear 49-20582 number and discloses catalyzer such as a kind of use such as aluminum oxide, silica-alumina, activated carbon, silica gel or silica-magnesia are prepared N-Methyl pyrrolidone by gamma-butyrolactone and Monomethylamine method (yield: 63%～93%).Recently, Akzo Noble is at United States Patent (USP) the 5th, 478, reported in No. 950 and used the X type zeolite catalyst of sodium ion exchange to prepare N-Methyl pyrrolidone (yield: 96%) by the successive reaction at 275 ℃.
Yet because catalytic activity descends, therefore above-mentioned catalysis process needs frequent catalyst recycle and separated product.As a result, be difficult to catalyzer is used long time, do not use the method for catalyzer more effective economically.Therefore, need a kind of novel reaction system of exploitation, described novel reaction system can be under the mild conditions that does not use catalyzer with stable and chronically with the required product of high produced in yields.
Summary of the invention
Technical problem
The object of the present invention is to provide a kind of method for preparing N-Methyl pyrrolidone (NMP), described method can be produced N-Methyl pyrrolidone with high yield and high-purity large-scale ground under the reaction conditions of gentleness, and minimum and waste water generates less to the demand of purifying, wherein, Monomethylamine (MMA) aqueous solution and gamma-butyrolactone (GBL) are provided in reactor, N-Methyl pyrrolidone that utilizes temperature of reaction and pressure and need not to be obtained by the reaction of Monomethylamine and gamma-butyrolactone from indirect heating and water sepn and the isolating water of institute mixed with Monomethylamine to prepare monomethylamine aqueous solution it is drawn be back in the reactor then.
Technical scheme
In a total scheme, providing can be with the method for preparing N-Methyl pyrrolidone (NMP) of high yield and high-purity large-scale ground production N-Methyl pyrrolidone, wherein, Monomethylamine (MMA) aqueous solution and gamma-butyrolactone (GBL) are provided in reactor, N-Methyl pyrrolidone that will be obtained by the reaction of Monomethylamine and gamma-butyrolactone and water sepn and the isolating water of institute mixed with Monomethylamine to prepare monomethylamine aqueous solution it is drawn be back in the reactor then.
Consider economy and efficient, optimum reaction conditions can be that temperature is that 260 ℃～320 ℃ and pressure are 50 crust～120 crust, and preferred temperature is that 270 ℃～310 ℃ and pressure are 70 crust～110 crust.
Can cling to the separator that moves under the pressure of～70 crust by one or more temperature and 0 and collect the isolating water of institute, provide it to reactor then with the preparation monomethylamine aqueous solution at 100 ℃～300 ℃.When being recycled in reactor by pipeline isolating water, can come water back,, shorten the reaction times thus to prevent the inside reactor temperature variation by being arranged on pipeline external heated device.
Excessive Monomethylamine can mix with isolating water with the preparation monomethylamine aqueous solution in the reactor, provides to reactor then.
Monomethylamine aqueous solution can comprise the Monomethylamine of 25 weight %～65 weight % and the water of 35 weight %～75 weight %, and Monomethylamine can have 81%～100% purity, contain as 0%～19% dimethylamine (DMA) of impurity and 0%～19% Trimethylamine 99 (TMA).
In preparation method of the present invention, raw material Monomethylamine and gamma-butyrolactone can provide with 1.001～1.05, preferred 1.005～1.015 mol ratio.
Gamma-butyrolactone can be the gamma-butyrolactone of purifying or purifying not, and can be by 1,4-butyleneglycol (BDO) preparation.The gamma-butyrolactone of purifying or purifying can not have 80.000%～99.999% purity, and can contain as impurity 0.001%～10.000% be selected from C3 alcohol, C4 alcohol, tetrahydrofuran (THF), C3 aldehyde, hydroxyl tetrahydrofuran and 1, one or more materials of 4-butyleneglycol.Particularly, it can contain 1 of 0.001%～1.000% C3 alcohol as impurity, 0.001%～2.000% C4 alcohol, 0.001%～10.000% tetrahydrofuran (THF), 0.001%～5.000% C3 aldehyde, 0.001%～5.000% hydroxyl tetrahydrofuran and 0.001%～10.000%, 4-butyleneglycol.
The N-Methyl pyrrolidone that obtains can use the distiller purifying, and then by ion exchange resin, thereby preparation contains the following metal of 1ppb and do not contain the above particulate high purity N-methyl-2-pyrrolidone of 0.2 μ m.
Beneficial effect
The method for preparing N-Methyl pyrrolidone of the present invention (wherein, Monomethylamine (MMA) aqueous solution and gamma-butyrolactone (GBL) are provided in reactor, N-Methyl pyrrolidone that the reaction of Monomethylamine and gamma-butyrolactone is obtained and water sepn and with the isolating water of institute mix with Monomethylamine with prepare monomethylamine aqueous solution then it is drawn be back in the reactor) can be by reducing to the purifying demand minimum and under the reaction conditions of gentleness, making production efficiency reach the highest.In addition, because employed water is recycled in the reaction, so waste water generates and to be reduced to minimumly, and this has improved economy and has prevented environmental pollution.When being recycled in reactor by pipeline the isolating water of institute, can come water back,, shorten the reaction times thus to prevent the inside reactor temperature variation by being arranged on pipeline external heated device.In addition, by limiting the content of impurities in raw material Monomethylamine and the gamma-butyrolactone, be reduced to minimum for the restriction of raw material and working condition.Compare with existing method, the method for preparing N-Methyl pyrrolidone of the present invention can be produced desired product easily and need not complicated step with the high yield short period of time, and can simplify the yield of process and the commercial-scale production of improvement.
Description of drawings
Following description of the preferred embodiments in conjunction with the drawings, above-mentioned and other purpose of the present invention, feature and advantage will become apparent, in the accompanying drawing:
Fig. 1 is the synoptic diagram (R: reactor, S: separator) of the method for preparing N-Methyl pyrrolidone of an embodiment; And
Fig. 2 is the synoptic diagram (R: reactor, S: separator, D: distiller) of the method for preparing N-Methyl pyrrolidone of another embodiment.
The detailed description of key element
F1: gamma-butyrolactone (GBL)
F2: Monomethylamine (MMA)
F3: by mixing the monomethylamine aqueous solution for preparing with the water of supplying by F6 by the Monomethylamine of F2 supply
The mixture of F4:N-methyl-2-pyrrolidone (NMP) and water
The F5:N-methyl-2-pyrrolidone
F6: by collecting the monomethylamine aqueous solution that isolating water prepares F3
F7: ion exchange resin
Embodiment
Describe embodiments of the present invention below with reference to the accompanying drawings in detail.
As shown in Figure 1, in reactor R, provide monomethylamine aqueous solution F3 and gamma-butyrolactone F1, and it is reacted under the pressure of 260 ℃～320 ℃ temperature and 50 crust～120 crust.The N-Methyl pyrrolidone F4 that generates is thus separated by separator S with water F4.Isolating water F6 by one or more at 100 ℃～300 ℃ temperature and the pressure of 0 crust～70 crust under the separator that moves collect, and mix with Monomethylamine F2 and prepare the monomethylamine aqueous solution F3 that is recycled into once more among the reactor R.
In another embodiment, as shown in Figure 2, in reactor R, provide monomethylamine aqueous solution F3 and gamma-butyrolactone F1, and it is reacted under the pressure of 260 ℃～320 ℃ temperature and 50 crust～120 crust.The N-Methyl pyrrolidone F4 that generates is thus separated by separator S with water F4.Isolating water F6 by one or more at 100 ℃～300 ℃ temperature and the pressure of 0 crust～70 crust under the separator that moves collect, and mix with Monomethylamine F2 and prepare the monomethylamine aqueous solution F3 that is recycled into once more among the reactor R.By distiller D purifying, and by ion exchange resin F7, thereby preparation contains the following metal of 1ppb and does not contain the above particulate high-purity N-methyl-2-pyrrolidone of 0.2 μ m by the isolating N-Methyl pyrrolidone F5 of separator S.
Embodiment
Below embodiment and experiment will be described.Following examples and experiment and are not intended to and limit the scope of the invention only for illustration purposes.
Embodiment 1
Monomethylamine aqueous solution F3 and gamma-butyrolactone F1 are provided to flow reactor R, and it is reacted under the pressure of 300 ℃ temperature and 100 crust, and liquid hourly space velocity (LHSV) is 1.0.By being positioned at the separator S behind the reactor R, that the N-Methyl pyrrolidone F4 and the water F4 that generate thus is separated from one another.Isolating water F6 by one or more at 200 ℃ temperature and the pressure of 40 crust under the separator that moves collect, and mix with Monomethylamine F2 and prepare the monomethylamine aqueous solution F3 that is recycled into once more among the reactor R.To provide excessive Monomethylamine for 1.01 mol ratio with respect to gamma-butyrolactone.Transformation efficiency and yield (it depends on the concentration of reactant Monomethylamine (MMA)) are as shown in table 1.
Comparative example
Prepare N-Methyl pyrrolidone in the mode similar to embodiment 1, difference is, uses 99.9% Monomethylamine gas to replace monomethylamine aqueous solution.Transformation efficiency and yield are as shown in table 1.
Table 1
| MMA concentration (%) | Transformation efficiency (%) | Yield (%) | |
| Experiment 1 | 10.3 | 96.6 | 92.8 |
| Experiment 2 | 30.6 | 99.9 | 99.8 |
| Experiment 3 | 41.9 | 99.9 | 99.9 |
| Experiment 4 | 80.0 | 51.5 | 25.5 |
| Comparative example | 99.9 | 40.2 | 15.9 |
As shown in table 1, when Monomethylamine provides with the aqueous solution, higher transformation efficiency and yield when having obtained to provide with gas than Monomethylamine.Particularly, when the concentration of Monomethylamine in the aqueous solution was 30.6% or 41.9%, transformation efficiency was 99.9%, and yield is respectively 99.8% or 99.9%.
Embodiment 2
Under the reaction conditions identical, prepare N-Methyl pyrrolidone with embodiment 1.The result relevant with impurities in the monomethylamine aqueous solution is as shown in table 2.
Table 2
MMA: Monomethylamine, DMA: dimethylamine, TMA: Trimethylamine 99
As shown in table 2, though when Monomethylamine content only be 80% and impurity dimethylamine and Trimethylamine 99 content up to 30% the time, transformation efficiency also be 99.9% and yield also be more than 99.7%.
Embodiment 3
Under the reaction conditions identical, use the gamma-butyrolactone of purifying not or purifying to prepare N-Methyl pyrrolidone with embodiment 1.The result is as shown in table 3.
Table 3
GBL: gamma-butyrolactone, THF: tetrahydrofuran (THF), THFOH: hydroxyl tetrahydrofuran, BDO:1,4-butyleneglycol
What use in the experiment 9 is the gamma-butyrolactone of purifying, uses by 1 the gamma-butyrolactone of 4-butyleneglycol preparation in experiment 10 and the experiment 11 without any purifying.Transformation efficiency and yield are all 99.9% under all situations.
Embodiment 4
Will with embodiment 1 same reaction conditions under the reaction product F5 for preparing, use distiller D purifying and by ion exchange resin F7.The result is as shown in table 4.
Table 4
By ion exchange resin, N-Methyl pyrrolidone has not passed through ion exchange resin to N-Methyl pyrrolidone in 13 and test in the experiment 12.Make metal and anion-content be reduced to the degree that is applicable to electron device by ion exchange resin.
The application comprise with on July 29th, 2009 to 10-2009-0069391 number relevant theme of korean patent application that Korea S Department of Intellectual Property submits, by quoting its full content is incorporated in this specification sheets.
It will be understood to those of skill in the art that disclosed notion and embodiment in the above description can be easily with making an amendment or designing the basis of other embodiment of realizing same purpose of the present invention.Those skilled in the art also will understand, and this embodiment that is equal to can not deviate from as the spirit and scope of the present invention as illustrated in the claims.
Claims (10)
1. method for preparing N-Methyl pyrrolidone (NMP), wherein, Monomethylamine (MMA) aqueous solution and gamma-butyrolactone (GBL) are provided in reactor, N-Methyl pyrrolidone that will be obtained by the reaction of Monomethylamine and gamma-butyrolactone and water sepn and the isolating water of institute mixed with Monomethylamine to prepare monomethylamine aqueous solution it is drawn be back in the described reactor then.
2. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, the temperature of described inside reactor is 260 ℃～320 ℃, and the pressure of described inside reactor is 50 crust～120 crust.
3. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, described isolating water by one or more at 100 ℃～300 ℃ temperature and the pressure of 0 crust～70 crust under the separator that moves collect to prepare described monomethylamine aqueous solution, provide it to described reactor then.
4. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, described monomethylamine aqueous solution comprises the Monomethylamine of 25 weight %～65 weight % and the water of 35 weight %～75 weight %.
5. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, described Monomethylamine has 81%～100% purity, and contains as 0%～19% dimethylamine (DMA) of impurity and 0%～19% Trimethylamine 99 (TMA).
6. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, described Monomethylamine and described gamma-butyrolactone provide with 1.001～1.05 mol ratio.
7. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, described gamma-butyrolactone is the gamma-butyrolactone of purifying or purifying not.
8. the method for preparing N-Methyl pyrrolidone as claimed in claim 7, wherein, the gamma-butyrolactone of described not purifying or purifying is by 1, and 4-butyleneglycol (BDO) prepares.
9. the method for preparing N-Methyl pyrrolidone as claimed in claim 8, wherein, the gamma-butyrolactone of described not purifying or purifying has 80.000%～99.999% purity, and contain as impurity 0.001%～10.000% be selected from C3 alcohol, C4 alcohol, tetrahydrofuran (THF), C3 aldehyde, hydroxyl tetrahydrofuran and 1, one or more materials in the 4-butyleneglycol.
10. the method for preparing N-Methyl pyrrolidone as claimed in claim 1, wherein, the isolating N-Methyl pyrrolidone of institute uses the distiller purifying, and by ion exchange resin, thereby preparation contains the following metal of 1ppb and does not contain the above particulate high-purity N-methyl-2-pyrrolidone of 0.2 μ m.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103351321A (en) * | 2013-06-20 | 2013-10-16 | 滨州裕能化工有限公司 | Continuous energy-saving NMP (N-methyl pyrrolidone) production method |
| CN105175306A (en) * | 2015-08-13 | 2015-12-23 | 张铨望 | Synthetic method of N-methylpyrrolidone |
| CN105237456A (en) * | 2015-10-19 | 2016-01-13 | 北京石油化工学院 | Production method of pyrrolidone products |
| CN106278983A (en) * | 2015-06-05 | 2017-01-04 | 中国石化仪征化纤有限责任公司 | A kind of N-Methyl pyrrolidone continuous preparation method |
| CN108299266A (en) * | 2018-01-30 | 2018-07-20 | 宁波大学 | The preparation method of high purity N-methyl pyrrolidone |
| CN111978184A (en) * | 2020-09-14 | 2020-11-24 | 安徽英特力工业工程技术有限公司 | Retrieve device of methylamine in follow NMP crude |
| CN117088801A (en) * | 2023-08-01 | 2023-11-21 | 赣州中能实业有限公司 | Refining method of N-methyl pyrrolidone |
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| CN207632732U (en) * | 2017-05-10 | 2018-07-20 | 奥加诺株式会社 | The purification system of NMP aqueous solutions |
| CN115819312B (en) * | 2022-05-17 | 2023-11-07 | 重庆中润新材料股份有限公司 | Production method for preparing NMP (N-methyl pyrrolidone) from anhydrous monomethylamine |
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| CN103351321A (en) * | 2013-06-20 | 2013-10-16 | 滨州裕能化工有限公司 | Continuous energy-saving NMP (N-methyl pyrrolidone) production method |
| CN103351321B (en) * | 2013-06-20 | 2015-08-26 | 滨州裕能化工有限公司 | The continuous production method of a kind of NMP |
| CN106278983A (en) * | 2015-06-05 | 2017-01-04 | 中国石化仪征化纤有限责任公司 | A kind of N-Methyl pyrrolidone continuous preparation method |
| CN105175306A (en) * | 2015-08-13 | 2015-12-23 | 张铨望 | Synthetic method of N-methylpyrrolidone |
| CN105237456A (en) * | 2015-10-19 | 2016-01-13 | 北京石油化工学院 | Production method of pyrrolidone products |
| CN105237456B (en) * | 2015-10-19 | 2017-12-22 | 北京石油化工学院 | A kind of production method of pyrrolidinone compounds product |
| CN108299266A (en) * | 2018-01-30 | 2018-07-20 | 宁波大学 | The preparation method of high purity N-methyl pyrrolidone |
| CN111978184A (en) * | 2020-09-14 | 2020-11-24 | 安徽英特力工业工程技术有限公司 | Retrieve device of methylamine in follow NMP crude |
| CN117088801A (en) * | 2023-08-01 | 2023-11-21 | 赣州中能实业有限公司 | Refining method of N-methyl pyrrolidone |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20110011917A (en) | 2011-02-09 |
| CN105906542A (en) | 2016-08-31 |
| KR101125853B1 (en) | 2012-03-28 |
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