CN103787906A - Method for preparing N,N-dimethylacetylamide - Google Patents
Method for preparing N,N-dimethylacetylamide Download PDFInfo
- Publication number
- CN103787906A CN103787906A CN201410060502.3A CN201410060502A CN103787906A CN 103787906 A CN103787906 A CN 103787906A CN 201410060502 A CN201410060502 A CN 201410060502A CN 103787906 A CN103787906 A CN 103787906A
- Authority
- CN
- China
- Prior art keywords
- formaldehyde
- dimethylacetamide
- formic acid
- methylacetamide
- reaction
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 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 27
- 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 10
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims abstract description 8
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims abstract description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 21
- -1 catalyzer Chemical compound 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
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 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
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 238000003912 environmental pollution Methods 0.000 abstract description 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 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
- 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
- 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
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
That N,N-dimethylacetamide has is thermally-stabilised, hydrolysis, the advantage such as corrosion-resistant, is widely used in the synthetic 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 take diacetyl oxide (or Acetyl Chloride 98Min. or acetic acid) and dimethylamine as raw material, exists and substitution reaction occurs forms N,N-dimethylacetamide down through catalyzer.Diacetyl oxide method exists energy consumption high, 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 height in acetyl chloride method; Acetic exists energy consumption high, and reaction process is long, high in cost of production defect.
Summary of the invention
In order to overcome the problem of prior art existence, 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 ℃ simultaneously, formaldehyde, formic acid, catalyzer, N-methylacetamide, feeding intake of water are (0.01%-10%) in mass ratio: (0.01%-23%): (0.01%-5%): (0.01%-24.33%): (37.67%-99.96%) add;
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 for (0.01%-10%): (0.01%-24.33%), maintenance system temperature 30-120 ℃, reaction 1-30 h, through centrifugal, filter, underpressure distillation, 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, take formic acid and formaldehyde as starting raw material, first, under catalyzer exists, utilizes formic acid and formaldehyde reaction to produce active intermediate compound; Secondly, utilize active intermediate compound to react with N-methylacetamide; 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, temperature of reaction height, have also avoided the problem of environmental pollution in preparation process.The present invention has advantages of that low temperature, environmental protection, flow process are short.
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 ℃, vigorous stirring reaction 1h;
Speed dropping 24gN-methylacetamide with constant pressure funnel with 0.5d/s, maintains at 50 ℃ and reacts 2h;
Reaction solution is through too 3000 turning centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 100 ℃ of underpressure distillation 5h, collect 164-166 ℃ 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 ℃, vigorous stirring reaction 1.5h;
Speed dropping 24gN-methylacetamide with dropping funnel with 0.5d/s, maintains at 55 ℃ and reacts 3h;
Reaction solution is through too 3000 turning centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 105 ℃ of underpressure distillation 6h, collect 164-166 ℃ of cut, obtain N,N-dimethylacetamide.
Embodiment 3
Take 10g formaldehyde, 21g formic acid, 5g catalyzer and 106g water and join in reactor, maintain 70 ℃, vigorous stirring reaction 2h;
Speed dropping 25gN-methylacetamide with dropping funnel with 0.5d/s, maintains at 60 ℃ and reacts 4h;
Reaction solution is through too 3000 turning centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 110 ℃ of underpressure distillation 3h, collect 164-166 ℃ of cut, obtain N,N-dimethylacetamide.
Embodiment 4
Take 10g formaldehyde, 20g formic acid, 5g catalyzer and 189g water and join in reactor, maintain 75 ℃, vigorous stirring reaction 4h;
Speed dropping 26g ethanamide with dropping funnel with 0.5d/s, maintains at 65 ℃ and reacts 6h;
Reaction solution is through too 3000 turning centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.09MPa, and 120 ℃ of underpressure distillation 6h, collect 164-166 ℃ of cut, obtain N,N-dimethylacetamide.
Embodiment 5
Take 10g formaldehyde, 18g formic acid, 5 catalyzer and 441g water and join in reactor, maintain 80 ℃, vigorous stirring reaction 6h;
Speed dropping 26g urea with dropping funnel with 0.5d/s, maintains at 70 ℃ and reacts 5h;
Reaction solution is through too 3000 turning centrifugation 30min; Adopt qualitative filter paper decompress filter 30min, gained filtrate is in-0.1MPa, and 115 ℃ of underpressure distillation 6h, collect 164-166 ℃ of cut, obtain N,N-dimethylacetamide.
Claims (3)
1. a preparation method for N,N-dimethylacetamide, 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 ℃ simultaneously, the mass ratio that feeds intake of formaldehyde, formic acid, catalyzer, N-methylacetamide, water is 0.01%-10%:0.01%-23%:0.01%-5%:0.01%-24.33%: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 ℃, reaction 1-30 h, obtains product N,N-dimethylacetamide.
2. the method processed of N,N-dimethylacetamide according to claim 1 is standby, it is characterized in that: described catalyzer is through one or more mixtures in pretreated HTS, gac, palladium charcoal.
3. the method processed of N,N-dimethylacetamide according to claim 1 is standby, it is characterized in that: described nitrogenous compound is one or more mixtures in N-methylacetamide, ethanamide, urea.
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 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410060502.3A CN103787906B (en) | 2014-02-24 | 2014-02-24 | Method for preparing N,N-dimethylacetylamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN103787906A true CN103787906A (en) | 2014-05-14 |
| CN103787906B CN103787906B (en) | 2015-06-17 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410060502.3A Expired - Fee Related CN103787906B (en) | 2014-02-24 | 2014-02-24 | Method for preparing N,N-dimethylacetylamide |
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| Country | Link |
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| CN (1) | CN103787906B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
Citations (2)
| 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 |
-
2014
- 2014-02-24 CN CN201410060502.3A patent/CN103787906B/en not_active Expired - Fee Related
Patent Citations (2)
| 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 |
Non-Patent Citations (1)
| Title |
|---|
| JAMES A.MITCHELL ET AL.,: "Preparation of aliphatic amides", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》, vol. 53, 31 May 1931 (1931-05-31), pages 1879 - 1883 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 | Publication date |
|---|---|
| CN103787906B (en) | 2015-06-17 |
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| C14 | Grant of patent or utility model | ||
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Inventor after: Gao Nan Inventor before: Yu Wangwang |
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| CB03 | Change of inventor or designer information | ||
| 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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