CN103787906B - Method for preparing N,N-dimethylacetylamide - Google Patents
Method for preparing N,N-dimethylacetylamide Download PDFInfo
- Publication number
- CN103787906B CN103787906B CN201410060502.3A CN201410060502A CN103787906B CN 103787906 B CN103787906 B CN 103787906B CN 201410060502 A CN201410060502 A CN 201410060502A CN 103787906 B CN103787906 B CN 103787906B
- Authority
- CN
- China
- Prior art keywords
- formaldehyde
- formic acid
- dimethylacetamide
- reaction
- dimethylacetylamide
- 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.)
- Expired - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 30
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 24
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 15
- 235000019253 formic acid Nutrition 0.000 claims abstract description 15
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 9
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims abstract description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 20
- -1 catalyzer Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003125 aqueous solvent Substances 0.000 claims description 2
- 238000012423 maintenance Methods 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 2
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 238000001914 filtration Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000005292 vacuum distillation Methods 0.000 abstract 1
- 238000004821 distillation Methods 0.000 description 7
- 238000005119 centrifugation Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for preparing N,N-dimethylacetylamide. The method comprises the following steps: by taking formaldehyde, formic acid and N-methylacetamide as raw materials, firstly, enabling formaldehyde to react with the formic acid to form an active intermediate under a catalyst and the heating condition; secondly, enabling the generated active intermediate to react with the N-methylacetamide, so as to form the N,N-dimethylacetylamide; finally, obtaining the N,N-dimethylacetylamide from the product by the processes of centrifuging, filtering, vacuum distillation and the like. The method is short in preparation flow, and low in reaction temperature, and has the advantages of being low in temperature, environmental, and short in flow, and the problem of environmental pollution in the preparation process is avoided.
Description
Technical field
The present invention relates to a kind of preparation method of organic solvent N,N-dimethylacetamide.
Background technology
N,N-dimethylacetamide has thermally-stabilised, hydrolysis, the advantage such as corrosion-resistant, is widely used in the synthesis of the resin such as polyimide, polysulfonamides.Therefore, it is more and more taken seriously.
At present, the preparation method of N,N-dimethylacetamide mainly contains diacetyl oxide method, acetyl chloride method and Acetic.This several method is all with diacetyl oxide (or Acetyl Chloride 98Min. or acetic acid) and dimethylamine for raw material, exists substitution reaction occurs form N,N-dimethylacetamide down through catalyzer.It is high to there is energy consumption in diacetyl oxide method, and reaction process is long, high in cost of production defect; There is the problems such as raw materials cost is high, reaction conditions requirement is high in acetyl chloride method; It is high to there is energy consumption in Acetic, and reaction process is long, high in cost of production defect.
Summary of the invention
In order to overcome prior art Problems existing, the object of this invention is to provide a kind of preparation method of N,N-dimethylacetamide, the method is by changing reactant feed and solvent species, and preparation flow is short, and temperature of reaction is low.
The object of the invention is to be achieved through the following technical solutions:
A kind of method processed of N,N-dimethylacetamide is standby, it is characterized in that: the method comprises the following steps:
1) under catalyzer existence condition, formic acid and formaldehyde are put in aqueous solvent, stir, and being heated to 30-120 DEG C simultaneously, feeding intake of formaldehyde, formic acid, catalyzer, N-methylacetamide, water is (0.01%-10%) in mass ratio: (0.01%-23%): (0.01%-5%): (0.01%-24.33%): (37.67%-99.96%) adds;
2) formic acid and formaldehyde reaction 1-6 hour is treated, dropwise add nitrogenous compound, the mass ratio that feeds intake of formaldehyde and nitrogenous compound is for (0.01%-10%): (0.01%-24.33%), maintenance system temperature 30-120 DEG C, reaction 1-30 h, through centrifugal, filter, underpressure distillation, namely obtains product N,N-dimethylacetamide.
In the present invention, described catalyzer is through one or more mixtures in pretreated HTS, gac, palladium charcoal.
Described nitrogenous compound is one or more mixtures in N-methylacetamide, ethanamide, urea.
The present invention for starting raw material, first, in the presence of a catalyst, utilizes formic acid and formaldehyde reaction to produce active intermediate compound with formic acid and formaldehyde; Secondly, active intermediate compound and N-methylacetamide is utilized to react; Finally, through centrifugal, filter, reduced pressure distillation process, obtains N,N-dimethylacetamide.The defects such as it is long that the present invention not only solves N,N-dimethylacetamide preparation flow, and temperature of reaction is high, also avoid the problem of environmental pollution in preparation process.The present invention has the short advantage of low temperature, environmental protection, flow process.
Embodiment
Embodiment 1
A kind of method processed of N,N-dimethylacetamide is standby, takes 10g formaldehyde, 23g formic acid, 5g catalyzer and 38g water and joins in reactor, maintains 60 DEG C, vigorous stirring reaction 1h;
Drip 24gN-methylacetamide with constant pressure funnel with the speed of 0.5d/s, at maintaining 50 DEG C, react 2h;
Reaction solution is through too 3000 turns of centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 100 DEG C of underpressure distillation 5h, collect 164-166 DEG C of cut, obtain N,N-dimethylacetamide.
Embodiment 2
The method processed of another N,N-dimethylacetamide is standby, takes 10g formaldehyde, 22g formic acid, 5g catalyzer and 64g water and joins in reactor, maintains 65 DEG C, vigorous stirring reaction 1.5h;
Drip 24gN-methylacetamide with dropping funnel with the speed of 0.5d/s, at maintaining 55 DEG C, react 3h;
Reaction solution is through too 3000 turns of centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 105 DEG C of underpressure distillation 6h, collect 164-166 DEG C of cut, obtain N,N-dimethylacetamide.
Embodiment 3
Taking 10g formaldehyde, 21g formic acid, 5g catalyzer and 106g water joins in reactor, maintains 70 DEG C, vigorous stirring reaction 2h;
Drip 25gN-methylacetamide with dropping funnel with the speed of 0.5d/s, at maintaining 60 DEG C, react 4h;
Reaction solution is through too 3000 turns of centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 110 DEG C of underpressure distillation 3h, collect 164-166 DEG C of cut, obtain N,N-dimethylacetamide.
Embodiment 4
Taking 10g formaldehyde, 20g formic acid, 5g catalyzer and 189g water joins in reactor, maintains 75 DEG C, vigorous stirring reaction 4h;
Drip 26g ethanamide with dropping funnel with the speed of 0.5d/s, at maintaining 65 DEG C, react 6h;
Reaction solution is through too 3000 turns of centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.09MPa, and 120 DEG C of underpressure distillation 6h, collect 164-166 DEG C of cut, obtain N,N-dimethylacetamide.
Embodiment 5
Taking 10g formaldehyde, 18g formic acid, 5 catalyzer and 441g water joins in reactor, maintains 80 DEG C, vigorous stirring reaction 6h;
Drip 26g urea with dropping funnel with the speed of 0.5d/s, at maintaining 70 DEG C, react 5h;
Reaction solution is through too 3000 turns of centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 115 DEG C of underpressure distillation 6h, collect 164-166 DEG C of cut, obtain N,N-dimethylacetamide.
Claims (2)
1. a preparation method for N,N-dimethylacetamide, is characterized in that: the method comprises the following steps:
1) under catalyzer existence condition, put in aqueous solvent by formic acid and formaldehyde, stir, and be heated to 30-120 DEG C simultaneously, the mass ratio that feeds intake of formaldehyde, formic acid, catalyzer, water is 0.01%-10%:0.01%-23%:0.01%-5%:37.67%-99.96%;
2) treat formic acid and formaldehyde reaction 1-6 hour, dropwise add nitrogenous compound, the mass ratio that feeds intake of formaldehyde and nitrogenous compound is 0.01%-10%:0.01%-24.33%, maintenance system temperature 30-120 DEG C, reaction 1-30 h, namely obtains product N,N-dimethylacetamide; Described nitrogenous compound is one or more mixtures in N-methylacetamide, ethanamide.
2. the preparation method of N,N-dimethylacetamide according to claim 1, is characterized in that: described catalyzer is through one or more mixtures in pretreated HTS, gac, palladium charcoal.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410060502.3A CN103787906B (en) | 2014-02-24 | 2014-02-24 | Method for preparing N,N-dimethylacetylamide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410060502.3A CN103787906B (en) | 2014-02-24 | 2014-02-24 | Method for preparing N,N-dimethylacetylamide |
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| Publication Number | Publication Date |
|---|---|
| CN103787906A CN103787906A (en) | 2014-05-14 |
| CN103787906B true CN103787906B (en) | 2015-06-17 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201410060502.3A Expired - Fee Related CN103787906B (en) | 2014-02-24 | 2014-02-24 | Method for preparing N,N-dimethylacetylamide |
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Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110483325A (en) * | 2019-09-26 | 2019-11-22 | 新乡双鹭药业有限公司 | A kind of method of purification of NN dimethyl acetamide |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5041659A (en) * | 1990-04-26 | 1991-08-20 | The Standard Oil Company | Synthesis of n-disubstituted amides by reaction of amides with certain organic hydroxyl compounds |
| US5118846A (en) * | 1990-04-27 | 1992-06-02 | The Standard Oil Company | Synthesis of N-disubstituted amides by reaction of amides with certain organic hydroxyl compounds |
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| CN103787906A (en) | 2014-05-14 |
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| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CB03 | Change of inventor or designer information | ||
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Inventor after: Gao Nan Inventor before: Yu Wangwang |
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| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20170915 Address after: 221000, No. 7, Xiao Huang Town, Zhang Zhuang Town, Xuzhou, Jiangsu, Peixian Patentee after: Gao Nan Address before: 210016 Jiangsu Province, Nanjing Xianlin University City, Yang Shan Road No. 1 Patentee before: Nanjing Institute of Industry Technology |
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| CF01 | Termination of patent right due to non-payment of annual fee | ||
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Granted publication date: 20150617 |