CN115894275A - Synthesis method of N, N-dialkyl-3-alkoxy propionamide - Google Patents
Synthesis method of N, N-dialkyl-3-alkoxy propionamide Download PDFInfo
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- CN115894275A CN115894275A CN202211255468.6A CN202211255468A CN115894275A CN 115894275 A CN115894275 A CN 115894275A CN 202211255468 A CN202211255468 A CN 202211255468A CN 115894275 A CN115894275 A CN 115894275A
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- 229940080818 propionamide Drugs 0.000 title claims abstract description 19
- 238000001308 synthesis method Methods 0.000 title description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 238000002360 preparation method Methods 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 20
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 230000002194 synthesizing effect Effects 0.000 claims abstract description 13
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims abstract description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims description 45
- 239000007787 solid Substances 0.000 claims description 41
- 239000002585 base Substances 0.000 claims description 37
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 22
- -1 alcohol compound Chemical class 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 4
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 claims description 4
- 239000002808 molecular sieve Substances 0.000 claims description 4
- 229910052901 montmorillonite Inorganic materials 0.000 claims description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims description 4
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 3
- 239000003208 petroleum Substances 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
- 238000007259 addition reaction Methods 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 claims description 2
- 229960001545 hydrotalcite Drugs 0.000 claims description 2
- 229910001701 hydrotalcite Inorganic materials 0.000 claims description 2
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 42
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 239000012535 impurity Substances 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000000047 product Substances 0.000 description 20
- 239000012043 crude product Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 238000001035 drying Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 230000003472 neutralizing effect Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 238000007086 side reaction Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical group [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 238000010189 synthetic method Methods 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 3
- LBVMWHCOFMFPEG-UHFFFAOYSA-N 3-methoxy-n,n-dimethylpropanamide Chemical compound COCCC(=O)N(C)C LBVMWHCOFMFPEG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical group [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 230000008929 regeneration Effects 0.000 description 2
- 238000011069 regeneration method Methods 0.000 description 2
- 238000002791 soaking Methods 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The application relates to the technical field of material preparation, and particularly discloses a method for synthesizing N, N-dialkyl-3-alkoxy propionamide, which comprises the following steps: reacting the compound II with the compound IV to obtain a compound I; the compound IV comprises dialkyl carbonate and dialkyl amine HN (R) 2 ) 2 One of (1); the synthetic route is as follows:
(ii) a Wherein R is 1 Is a C1-C8 hydrocarbon group, or a fluorinated hydrocarbon group; r 2 Is C1-C6 hydrocarbyl, glycidyl or fluoro hydrocarbyl. The preparation process of the whole synthesis route in the application has the advantages of simple operation, short reaction production period and high yield and purity; on the basis of ensuring the product quality, the production cost of the product is favorably reduced. And the product meets the requirements on the purity, the impurity content and the cost of the product in the market, and is suitable for industrial production.
Description
Technical Field
The application relates to the technical field of material preparation, in particular to a method for synthesizing N, N-dialkyl-3-alkoxy propionamide.
Background
The N, N-dialkyl-3-alkoxy propionamide has wide application prospect, in particular to the N, N-dimethyl-3-methoxy propionamide with the CAS number of 53185-52-7, is a colorless transparent solvent and has the characteristics of high solubility, high permeability, high fluidity, low viscosity, low surface tension and the like. The N-methyl pyrrolidone-containing emulsion has no irritation to skin, is low in toxicity, safe and environment-friendly, can well replace the traditional solvent N-methyl pyrrolidone, is widely applied to industries such as electronics, medicines, pesticides, pigments, cleaning agents and insulating materials, and has wide application prospects.
However, the related art for synthesizing N, N-dialkyl-3-alkoxypropionamide is not mature enough and there are few reports on the synthesis, so it is a necessary research topic to design a synthetic route for N, N-dialkyl-3-alkoxypropionamide.
Disclosure of Invention
In order to provide a synthesis method of N, N-dialkyl-3-alkoxy propionamide, which has the advantages of simple operation, low cost, high product yield and high purity, the application provides a synthesis method of N, N-dialkyl-3-alkoxy propionamide, and the following technical scheme is adopted:
a method for synthesizing N, N-dialkyl-3-alkoxy propionamide comprises the following steps: reacting the compound II with the compound IV to obtain a compound I; the compound IV comprises dialkyl carbonate and dialkyl amine HN (R) 2 ) 2 One of (a) and (b);
the synthetic route is as follows:
wherein R is 1 Is a C1-C8 hydrocarbon group, or a fluorinated hydrocarbon group; r is 2 Is C1-C6 hydrocarbyl, glycidyl or fluoro hydrocarbyl.
By adopting the technical scheme, the compound II, namely the 3-alkoxy propionamide and the compound IV are used as initial raw materials, the compound II and the compound IV are directly synthesized to obtain the compound I, the synthesis path is convenient, the operation is simple, the reaction production period is short, the yield and the purity of the synthesized compound I are high, the production cost is favorably reduced, and the industrial scale production is matched.
In a specific embodiment, the molar ratio of compound ii to compound iv is 1: (0.1-100).
By adopting the technical scheme, the molar ratio of the compound II to the compound IV is controlled to be 1: (0.1-100) is helpful for improving the reaction rate and the reaction degree and reducing the occurrence of side reactions, and has positive significance for improving the yield and the purity of the product.
In a specific embodiment, the preparation of compound II is as follows: in the presence of a solid base catalyst, acrylamide and an alcohol compound undergo an addition reaction to prepare 3-alkoxy propionamide, namely a compound II.
By adopting the technical scheme, the preparation step of the compound II is further disclosed, and the acrylamide is used as the initial raw material, so that the property of the acrylamide in the conventional state is stable and is easy to obtain.
In a specific possible embodiment, the solid base catalyst is obtained by supporting a basic component on a carrier.
Because the traditional alkaline catalyst can not be recycled and reused, and the post-treatment process is complex, the post-treatment process of the reaction product needs neutralization and washing, which causes the discharge of a large amount of waste water and environmental pollution.
By adopting the technical scheme, the solid base catalyst is obtained by further loading the alkaline component on the carrier, and has the advantages of difficult loss of an alkaline active center, large specific surface area of the catalyst, long service life of the catalyst, high mechanical strength, small corrosion of equipment, cyclic regeneration, repeated utilization, easy separation and recovery of products after reaction, environmental friendliness and the like.
After the reaction, the solid base catalyst can be separated from the reaction system only by filtration and centrifugal operation, thereby greatly simplifying the separation step of the solid base catalyst and being capable of efficiently recovering, and further reducing the production cost.
In a specific possible embodiment, the support comprises at least one of molecular sieves, alumina, zirconia, activated carbon, porous silica, hydrotalcite, montmorillonite, ion exchange resins, polymeric supports; the alkaline component comprises at least one of hydroxides of alkali metals or alkaline earth metals, oxides of alkali metals or alkaline earth metals, carbonates of alkali metals or alkaline earth metals, and tetraalkylammonium hydroxide.
In a specific embodiment, the alcohol compound includes one of aliphatic alcohol with 1-8 carbon atoms and fluoroalcohol compound.
In a specific embodiment, the molar ratio of acrylamide to alcohol compound is 1: (0.1-100).
By adopting the technical scheme, the molar ratio of acrylamide to alcohol compounds is controlled to be 1: (0.1-100) is helpful for improving the reaction rate and the reaction degree and reducing the occurrence of side reactions, and has positive significance for improving the yield and the purity of the product.
In a specific possible embodiment, the weight ratio of the solid base catalyst to acrylamide is (0.001-0.10): 1.
by adopting the technical scheme, the weight ratio of the solid base catalyst to the acrylamide is controlled to be (0.001-0.10): 1, the catalyst is helpful for improving the catalytic effect of the solid base catalyst, and has positive significance for improving the yield and the purity of the product.
In a specific embodiment, the preparation of the compound ii is performed in a reaction solvent, and the reaction solvent is at least one of alcohols, tetrahydrofuran, ethyl acetate, isopropyl ether, acetonitrile, and petroleum ether.
By adopting the technical scheme, the compound II is prepared in the reaction solvent, so that the reaction rate and the reaction balance can be effectively guaranteed, the side reaction can be effectively inhibited, and the method has positive significance for improving the utilization rate of raw materials, and further contributes to improving the yield and the purity of the product.
In summary, the present application has the following beneficial effects:
1. according to the method, the initial raw materials and the preparation process are optimized through a reasonable and convenient synthesis route, the yield and the purity of the synthesized compound I can be effectively improved on the basis of controlling the cost and reducing the operation difficulty, and the synthesis route is short in reaction period and suitable for industrial mass production.
2. The preparation and purification process provided by the application is easy to purify and separate by-products and impurities generated in the reaction process, the impurities in the product can reach the high-purity practical application standard without a complex purification process, the product preparation process is simplified, the product yield is high, the product purity is high, and the yield and quality requirements of large-scale application can be met.
3. The solid base catalyst is obtained by loading an alkaline component on a carrier, and has the advantages of simple operation, difficult loss of an alkaline active center, large specific surface area, long service life, high mechanical strength, small equipment corrosivity, cyclic regeneration, repeated utilization for multiple times, easy separation and recovery of products after reaction, environmental friendliness and the like.
4. The method further optimizes the raw material ratio, so that the reaction rate and the reaction degree are improved, side reactions are reduced, and the method has positive significance for further improving the product yield and purity.
5. By adopting the mode of preparing the compound II in the reaction solvent, the method can effectively improve the reaction rate, maintain the reaction balance, reduce the side reaction and contribute to further improving the product yield and purity.
Detailed Description
The pressure values mentioned in the present embodiment are gauge pressures unless otherwise specified, and gauge pressures refer to the total absolute pressure exceeding the ambient atmospheric pressure or the pressure at a point in the liquid higher than the atmospheric pressure.
The reaction temperature in the present embodiment is generally referred to as the oil bath temperature of the reaction unless otherwise specified.
The present application will be described in further detail with reference to the following preparation examples and examples, and all of the starting materials referred to in the present application are commercially available.
Preparation example of solid base catalyst
Preparation example 1
A solid base catalyst is prepared by the following steps:
a1, adding a carrier into a round-bottom flask, wherein the carrier is a 13X-type molecular sieve; adding an alkaline component and a methanol solvent which need to be loaded on a carrier, wherein the alkaline component is sodium hydroxide, the mass ratio of the carrier to the alkaline component is 4:1, dipping in a stirring state, and treating at normal temperature for 12h to obtain a solid alkali catalyst crude product;
and A2, sequentially filtering, drying and drying the crude solid base catalyst to obtain the sodium hydroxide-loaded molecular sieve, namely the finished solid base catalyst.
Preparation example 2
A solid base catalyst is prepared by the following steps:
a1, adding a carrier into a round-bottom flask, wherein the carrier is alumina; adding an alkaline component and an ethanol solvent which need to be loaded on a carrier, wherein the alkaline component is potassium carbonate, the mass ratio of the carrier to the alkaline component is 4:1, soaking the mixture in a stirring state, and heating the mixture to 30 ℃ for treatment for 12 hours under the protection of inert gas to obtain a crude solid alkali catalyst;
and A2, sequentially cooling, filtering, drying and drying the crude solid base catalyst to obtain the alumina loaded with potassium carbonate, namely the finished solid base catalyst.
Preparation example 3
A solid base catalyst is prepared by the following steps:
a1, adding a carrier into a round-bottom flask, wherein the carrier is montmorillonite; adding an alkaline component and an ethanol solvent which need to be loaded on a carrier, wherein the alkaline component is calcium hydroxide, the mass ratio of the carrier to the alkaline component is 4:1, soaking under a stirring state, and heating to 40 ℃ under the protection of inert gas for processing for 12 hours to obtain a crude solid alkali catalyst;
and A2, sequentially cooling, filtering, drying and drying the crude solid base catalyst to obtain the montmorillonite loaded with calcium hydroxide, namely the finished solid base catalyst.
Preparation example 4
A solid base catalyst is prepared by the following steps:
a1, adding a carrier into a round-bottom flask, wherein the carrier is zirconia; adding an alkaline component and water which need to be loaded on a carrier, wherein the alkaline component is tetraalkylammonium hydroxide, the mass ratio of the carrier to the alkaline component is 4:1, dipping in a stirring state, and treating at normal temperature for 12 hours to obtain a crude product of the solid alkali catalyst;
and A2, sequentially filtering, drying and drying the crude solid base catalyst to obtain the zirconium oxide loaded with the tetraalkylammonium hydroxide, namely the finished solid base catalyst.
Examples
Example 1
A synthetic method of N, N-dialkyl-3-alkoxy propionamide comprises the following steps:
the specific steps of the synthetic route are as follows:
s1, firstly, adding an alcohol compound and a solid base catalyst into a reactor with a stirrer, and slowly adding a methanol solution of acrylamide under stirring, wherein the reaction temperature is 45 ℃, the reaction pressure is normal pressure, and the reaction time is 6 hours; after the reaction is finished, cooling the temperature to room temperature, neutralizing the reaction solution by using hydrochloric acid until the pH value is 6.5-7.5, filtering the precipitate, and distilling the filtrate under reduced pressure to remove the solvent to obtain a compound II; wherein the mol ratio of the acrylamide to the alcohol compound is 1.25, and the weight ratio of the solid base catalyst to the acrylamide is 0.02:1, wherein the alcohol compound is methanol, and the solid base catalyst is prepared in preparation example 1;
s2, adding the compound II and the compound IV prepared in the step S1 into a high-pressure kettle with a stirrer to react, wherein the reaction temperature is 130 ℃, the reaction time is 6 hours, after the reaction is finished, the temperature is reduced to room temperature, taking out a reaction mixture, and performing reduced pressure distillation and separation to obtain a crude product of the compound I, wherein the yield of the crude product is 70%; wherein the molar ratio of the compound II to the compound IV is 1;
s3, purifying and rectifying the crude product of the compound I in a reactor, and collecting a main fraction at the temperature of 100 ℃/2mmHg to obtain the finished product of the compound I, wherein the purification yield is 85 percent, and the product purity is 99.5 percent.
Example 2
A synthetic method of N, N-dialkyl-3-alkoxy propionamide comprises the following steps:
the specific steps of the synthetic route are as follows:
s1, firstly, adding an alcohol compound and a solid base catalyst into a reactor with a stirrer, and slowly adding a tetrahydrofuran solution of acrylamide under stirring, wherein the reaction temperature is 35 ℃, the reaction pressure is normal pressure, and the reaction time is 5 hours; after the reaction is finished, cooling the temperature to room temperature, neutralizing the reaction product by using hydrochloric acid until the pH value is 6.5-7.5, filtering the precipitate, and distilling the filtrate under reduced pressure to remove the solvent to obtain a compound II; wherein the mol ratio of acrylamide to alcohol compound is 1.5, the weight ratio of solid base catalyst to acrylamide is 0.04:1, wherein the alcohol compound is ethanol, and the solid base catalyst is prepared in preparation example 2;
s2, adding the compound II and the compound IV prepared in the step S1 into a high-pressure kettle with a stirrer to react, wherein the reaction temperature is 140 ℃, the reaction time is 7h, after the reaction is finished, the temperature is reduced to room temperature, taking out a reaction mixture, neutralizing the reaction mixture by using a small amount of hydrochloric acid, and then separating the reaction mixture by reduced pressure distillation to obtain a crude product of the compound I, wherein the yield of the crude product is 62%; wherein the molar ratio of the compound II to the compound IV is 1.1, and the compound IV is diethylamine;
s3, purifying and rectifying the crude product of the compound I in a reactor, and collecting a main fraction at the temperature of 100 ℃/2mmHg to obtain the finished product of the compound I, wherein the purification yield is 70% and the product purity is 98.0%.
Example 3
A synthetic method of N, N-dialkyl-3-alkoxy propionamide comprises the following synthetic route:
the specific steps of the synthetic route are as follows:
s1, firstly, adding an alcohol compound and a solid base catalyst into a reactor with a stirrer, and slowly adding a petroleum ether solution of acrylamide under stirring, wherein the reaction temperature is 50 ℃, the reaction pressure is normal pressure, and the reaction time is 7 hours; after the reaction is finished, cooling the temperature to room temperature, neutralizing the reaction product by using hydrochloric acid until the pH value is 6.5-7.5, filtering the precipitate, and distilling the filtrate under reduced pressure to remove the solvent to obtain a compound II; wherein the mol ratio of acrylamide to alcohol compound is 1.8, the weight ratio of solid base catalyst to acrylamide is 0.03:1, the alcohol compound is propanol, and the solid base catalyst is prepared in preparation example 3;
s2, adding the compound II and the compound IV prepared in the step S1 into a high-pressure kettle with a stirrer to react at the reaction temperature of 150 ℃ for 8 hours, cooling the reaction mixture to room temperature after the reaction is finished, taking out the reaction mixture, and separating by reduced pressure distillation to obtain a crude product of the compound I, wherein the yield of the crude product is 64%; wherein the molar ratio of the compound II to the compound IV is 1;
s3, then purifying and rectifying the crude product of the compound I in a reactor, and collecting a main fraction at the temperature of 100 ℃/2mmHg to obtain the finished product of the compound I with the purification yield of 80% and the purity of 98.5%.
Example 4
A synthetic method of N, N-dialkyl-3-alkoxy propionamide comprises the following steps:
the specific steps of the synthetic route are as follows:
s1, firstly, adding an alcohol compound and a solid base catalyst into a reactor with a stirrer, and slowly adding an isopropyl ether solution of acrylamide under stirring, wherein the reaction temperature is 45 ℃, the reaction pressure is normal pressure, and the reaction time is 5 hours; after the reaction is finished, cooling the temperature to room temperature, neutralizing the reaction solution by using hydrochloric acid until the pH value is 6.5-7.5, filtering the precipitate, and distilling the filtrate under reduced pressure to remove the solvent to obtain a compound II; wherein the mol ratio of the acrylamide to the alcohol compound is 1:2, and the weight ratio of the solid base catalyst to the acrylamide is 0.06:1, the alcohol compound is trifluoroethanol, and the solid base catalyst is prepared in preparation example 4;
s2, adding the compound II and the compound IV prepared in the step S1 into a high-pressure kettle with a stirrer to react at the reaction temperature of 135 ℃ for 6 hours, cooling the reaction mixture to room temperature after the reaction is finished, taking out the reaction mixture, and separating the reaction mixture by reduced pressure distillation to obtain a crude product of the compound I, wherein the yield of the crude product is 68%; wherein the molar ratio of the compound II to the compound IV is 1;
s3, purifying and rectifying the crude product of the compound I in a reactor, and collecting a main fraction at the temperature of 100 ℃/2mmHg to obtain the finished product of the compound I, wherein the purification yield is 80% and the product purity is 99.2%.
The present embodiment is only for explaining the present application, and it is not limited to the present application, and those skilled in the art can make modifications of the present embodiment without inventive contribution as needed after reading the present specification, but all of them are protected by patent law within the scope of the claims of the present application.
Claims (10)
1. A method for synthesizing N, N-dialkyl-3-alkoxy propionamide is characterized by comprising the following steps: reacting a compound II, namely 3-alkoxy propionamide with a compound IV to obtain a compound I; the compound IV comprises dialkyl carbonate and dialkyl amine HN (R) 2 ) 2 One of (1);
the synthetic route is as follows:
wherein R is 1 Is a C1-C8 hydrocarbon group, or a fluorinated hydrocarbon group; r 2 Is C1-C6 hydrocarbyl, glycidyl or fluoro hydrocarbyl.
2. The method for synthesizing the N, N-dialkyl-3-alkoxy propionamide according to claim 1, wherein the molar ratio of the compound II to the compound IV is 1: (0.1-100).
3. The method for synthesizing N, N-dialkyl-3-alkoxy propionamide according to claim 1, wherein the preparation of the compound II comprises the following steps: acrylamide and alcohol compounds are subjected to addition reaction in the presence of a solid base catalyst to prepare 3-alkoxy propionamide, namely a compound II.
4. The method for synthesizing N, N-dialkyl-3-alkoxypropionamide according to claim 3, wherein the solid base catalyst is obtained by supporting a basic component on a carrier.
5. The method for synthesizing N, N-dialkyl-3-alkoxypropionamide according to claim 4, wherein the carrier comprises at least one of molecular sieve, alumina, zirconia, activated carbon, porous silica, hydrotalcite, montmorillonite, ion exchange resin and polymer carrier; the alkaline component comprises at least one of hydroxides of alkali metals or alkaline earth metals, oxides of alkali metals or alkaline earth metals, carbonates of alkali metals or alkaline earth metals, and tetraalkylammonium hydroxide.
6. The method for synthesizing N, N-dialkyl-3-alkoxypropionamide according to claim 3, wherein the alcohol compound comprises one of aliphatic alcohol and fluoroalcohol compound with 1-8 carbon atoms.
7. The method for synthesizing N, N-dialkyl-3-alkoxypropionamide according to claim 3, wherein the molar ratio of acrylamide to alcohol compound is 1: (0.1-100).
8. The method for synthesizing N, N-dialkyl-3-alkoxypropionamide according to claim 3, wherein the weight ratio of the solid base catalyst to the acrylamide is (0.001-0.10): 1.
9. the method for synthesizing N, N-dialkyl-3-alkoxypropionamide according to claim 3, wherein the preparation of the compound II is performed in a reaction solvent, and the reaction solvent is at least one of alcohols, tetrahydrofuran, ethyl acetate, isopropyl ether, acetonitrile and petroleum ether.
10. An N, N-dialkyl-3-alkoxypropionamide synthesized according to the method of any one of claims 1 to 9.
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|---|---|---|---|---|
| US3712926A (en) * | 1969-04-25 | 1973-01-23 | Basf Ag | Production of n-polyalkoxymethylamides |
| JPS63303960A (en) * | 1987-06-04 | 1988-12-12 | Tokuyama Soda Co Ltd | Production of oxyalkylamide |
| JP2004250353A (en) * | 2003-02-19 | 2004-09-09 | Idemitsu Petrochem Co Ltd | METHOD FOR PRODUCING beta-ALKOXYPROPIONAMIDE COMPOUNDS |
| JP2005047885A (en) * | 2003-07-17 | 2005-02-24 | Idemitsu Kosan Co Ltd | Beta-alkoxypropionamide compound, solvent, detergent and liquid chemical composition and method for producing beta-alkoxypropionamide compound |
| JP2009185079A (en) * | 2009-05-27 | 2009-08-20 | Idemitsu Kosan Co Ltd | METHOD FOR PRODUCING beta-ALKOXYPROPIONAMIDES |
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2022
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3712926A (en) * | 1969-04-25 | 1973-01-23 | Basf Ag | Production of n-polyalkoxymethylamides |
| JPS63303960A (en) * | 1987-06-04 | 1988-12-12 | Tokuyama Soda Co Ltd | Production of oxyalkylamide |
| JP2004250353A (en) * | 2003-02-19 | 2004-09-09 | Idemitsu Petrochem Co Ltd | METHOD FOR PRODUCING beta-ALKOXYPROPIONAMIDE COMPOUNDS |
| JP2005047885A (en) * | 2003-07-17 | 2005-02-24 | Idemitsu Kosan Co Ltd | Beta-alkoxypropionamide compound, solvent, detergent and liquid chemical composition and method for producing beta-alkoxypropionamide compound |
| JP2009185079A (en) * | 2009-05-27 | 2009-08-20 | Idemitsu Kosan Co Ltd | METHOD FOR PRODUCING beta-ALKOXYPROPIONAMIDES |
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| Title |
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| MASAZUMI TAMURA等: "Formation of a New, Strongly Basic Nitrogen Anion by Metal OxideModification", 《J.AM.CHEM.SOC.》, vol. 139, pages 11857 * |
| 田伟生，彭逸华译: "《有机合成中的副反应 成功合成设计指南》", 31 March 2006, 上海：华东理工大学出版社, pages: 243 * |
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