CN111054445B - Method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation, catalyst and application thereof - Google Patents
Method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation, catalyst and application thereof Download PDFInfo
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- CN111054445B CN111054445B CN202010031206.6A CN202010031206A CN111054445B CN 111054445 B CN111054445 B CN 111054445B CN 202010031206 A CN202010031206 A CN 202010031206A CN 111054445 B CN111054445 B CN 111054445B
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- 239000003054 catalyst Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 35
- 238000007112 amidation reaction Methods 0.000 title claims abstract description 23
- 230000009435 amidation Effects 0.000 title claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 47
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 claims abstract description 45
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 28
- 238000010438 heat treatment Methods 0.000 claims abstract description 23
- 239000002041 carbon nanotube Substances 0.000 claims abstract description 22
- 229910021393 carbon nanotube Inorganic materials 0.000 claims abstract description 22
- 230000003197 catalytic effect Effects 0.000 claims abstract description 17
- 239000003377 acid catalyst Substances 0.000 claims abstract description 16
- 238000003756 stirring Methods 0.000 claims abstract description 15
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 12
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000010936 titanium Substances 0.000 claims abstract description 12
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 12
- 229940017219 methyl propionate Drugs 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 239000002048 multi walled nanotube Substances 0.000 claims description 37
- 239000000047 product Substances 0.000 claims description 29
- STQPDNJGBTZGPF-UHFFFAOYSA-N 3-(diethylamino)-n,n-diethylpropanamide Chemical compound CCN(CC)CCC(=O)N(CC)CC STQPDNJGBTZGPF-UHFFFAOYSA-N 0.000 claims description 20
- 238000005406 washing Methods 0.000 claims description 18
- 230000002194 synthesizing effect Effects 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 13
- 238000010992 reflux Methods 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 10
- 238000001291 vacuum drying Methods 0.000 claims description 10
- JYUWLTALTNCMIP-UHFFFAOYSA-N C(CCC)O[Ti](C1C=CC=C1)OCCCC Chemical compound C(CCC)O[Ti](C1C=CC=C1)OCCCC JYUWLTALTNCMIP-UHFFFAOYSA-N 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 9
- QOXHZZQZTIGPEV-UHFFFAOYSA-K cyclopenta-1,3-diene;titanium(4+);trichloride Chemical compound Cl[Ti+](Cl)Cl.C=1C=C[CH-]C=1 QOXHZZQZTIGPEV-UHFFFAOYSA-K 0.000 claims description 9
- 229910017604 nitric acid Inorganic materials 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 9
- WXLJOGGIAUQFRX-UHFFFAOYSA-N 2-butan-2-yl-4,6-dinitronaphthalen-1-ol Chemical compound CCC(C)C1=CC(=C2C=C(C=CC2=C1O)[N+](=O)[O-])[N+](=O)[O-] WXLJOGGIAUQFRX-UHFFFAOYSA-N 0.000 claims description 8
- FRMHSZFRTXVUNP-UHFFFAOYSA-N 2-nonylnaphthalen-1-ol Chemical compound C1=CC=CC2=C(O)C(CCCCCCCCC)=CC=C21 FRMHSZFRTXVUNP-UHFFFAOYSA-N 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 8
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- 239000012153 distilled water Substances 0.000 claims description 5
- 239000002808 molecular sieve Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 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 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- 238000011068 loading method Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000012752 auxiliary agent Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- MGOYBMFCELTAHS-UHFFFAOYSA-N methyl 3-(diethylamino)propanoate Chemical compound CCN(CC)CCC(=O)OC MGOYBMFCELTAHS-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 238000009849 vacuum degassing Methods 0.000 claims description 3
- 238000013329 compounding Methods 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000000746 purification Methods 0.000 claims description 2
- 238000011938 amidation process Methods 0.000 claims 8
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 8
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000000052 comparative effect Effects 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 3
- 238000005520 cutting process Methods 0.000 description 3
- 238000007872 degassing Methods 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- -1 amide compound Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 229940044631 ferric chloride hexahydrate Drugs 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- ZCJKJJQMCWSWGZ-UHFFFAOYSA-N 3-(dimethylamino)-n,n-dimethylpropanamide Chemical compound CN(C)CCC(=O)N(C)C ZCJKJJQMCWSWGZ-UHFFFAOYSA-N 0.000 description 1
- 238000010146 3D printing Methods 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- LPUQAYUQRXPFSQ-DFWYDOINSA-M monosodium L-glutamate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCC(O)=O LPUQAYUQRXPFSQ-DFWYDOINSA-M 0.000 description 1
- 235000013923 monosodium glutamate Nutrition 0.000 description 1
- 239000004223 monosodium glutamate Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0225—Complexes comprising pentahapto-cyclopentadienyl analogues
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/46—Titanium
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Carbon And Carbon Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Abstract
The invention relates to the technical field of 3-diethylamino-N, N-diethyl propionamide, in particular to a method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation, and a catalyst and application thereof. The method comprises the following steps: mixing 3-diethylamino methyl propionate, a carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid catalyst and an organic titanium catalyst promoter, uniformly stirring, adding dried diethylamine, and reacting under a heating condition to obtain the catalyst. The method adopts the carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid to compound the organic titanium catalyst promoter, and has the advantages of small using amount of the catalyst, high catalytic efficiency, stable product performance, high conversion rate (more than 92 percent) and the like; moreover, the reaction process only needs to be carried out at 90-95 ℃ under normal pressure, and compared with the existing method which needs to be carried out at high temperature and high pressure, the method of the invention has obvious technical advantages.
Description
Technical Field
The invention relates to the technical field of 3-diethylamino-N, N-diethyl propionamide, in particular to a method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation, and a catalyst and application thereof.
Background
The information disclosed in this background of the invention is only for enhancement of understanding of the general background of the invention and is not necessarily to be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person skilled in the art.
3-diethylamino-N, N-diethyl-propionamide is an important amide compound. The cracking product has stable performance, no toxicity, no odor and no corrosiveness, can be mutually soluble with water or most organic solvents, and plays the roles of industrial yeast and industrial monosodium glutamate in the fields of UV ink, 3D printing, cosmetics, photoresist and the like.
The amido bond is one of the most basic chemical structures found in nature, which forms the skeleton of biological peptide and protein, the amido bonds with different structures have various biological activities, and the amide has great importance for biochemistry and organic chemistry, so the synthetic reaction of the amide is the key point of long-term research of organic synthesizers at home and abroad. Metal salt, metal oxide type catalysts are often used for the amidation catalysis of saturated carboxylic acids and amines. In 2008, Terada et al studied the amidation reaction of saturated carboxylic acid and long-chain amine, and used palmitic acid and decylamine as model reaction to examine the catalytic effect of a series of metal salts such as ferric chloride hexahydrate, zinc chloride, nickel chloride hexahydrate and the like at 160 ℃. When the carbon chain length of the acid substrate is 8 to 14, ferric chloride hexahydrate shows a good catalytic effect (see document 1). In 2012, Lundberg et al used titanium tetrachloride and zirconium tetrachloride for the catalytic formylation of phenylacetic acid with amines with conversion rates as high as 99%, but the reaction temperature was high (120 ℃) and the amount of catalyst used was large, 20% of the substrate (see document 2).
The preparation method of 3-diethylamino-N, N-diethyl propionamide or compounds with similar structures has also been studied. In 1948, cyanamide incorporated, USA, used ethyl acrylate and dimethylamine to prepare a mixed solution containing 3-dimethylamino-N, N-dimethylpropionamide by refluxing at 140 ℃ for 96 h. David Charles Priest and the like synthesize amidation products, namely 3-diethylamino-N, N-diethyl propionamide, by taking methyl acrylate and diethylamine as raw materials and phenothiazine and p-methoxynaphthol as polymerization inhibitors, wherein the reaction temperature is 180 ℃ and the reaction pressure is 200 ℃ and 320psig, the reaction time is 20-32h, and the product conversion rate is only 22% (see document 3). Alan s.rothenberg et al have studied the simultaneous addition-amidation of methyl methacrylate and excess N, N-dimethyl-1, 3-propanediamine as starting materials to obtain amidated products; the reaction temperature was 210 ℃ and 215 ℃ and the conversion of amidation product was 67.77% (see document 4).
Documents of the prior art
Document 1 (article), DOI: 10.1055/s-2008-1067168.
Document 2 (article), DOI: 10.1002/adsc.201200436.
Document 3 (patent): david Charles prime, beta-Amino Carbonyl Catalysts for Polyurethane preparation, us3954749, application date: 1975-05-04.
Document 4 (patent): alan S.Rothenberg.preparation of N-substitated acrylic Monomers providing abilities Substitations 67372, filing date: 1981-05-12.
Disclosure of Invention
In view of the defects of the prior art, the invention provides a method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation and a catalyst thereof, wherein the method has the advantages of small using amount of the catalyst, high catalytic efficiency, stable product performance, high conversion rate and the like, high temperature and high pressure are not needed in the reaction process, the amidation reaction is efficient, economic and green, and the obtained 3-diethylamino-N, N-diethyl propionamide is an important intermediate of unsaturated amide compounds.
The invention aims at providing a catalyst for synthesizing 3-diethylamino-N, N-diethyl propionamide and a preparation method thereof.
The second purpose of the invention is to provide a method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation.
The third purpose of the invention is to provide the catalyst and the application of the method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation.
In order to achieve the purpose, the invention adopts the following technical means:
the invention discloses a catalyst for synthesizing 3-diethylamino-N, N-diethyl propionamide, which is prepared by compounding a multi-walled carbon nanotube, 2-amino-5-naphthol-7-sulfonic acid and organic titanium, wherein the 2-amino-5-naphthol-7-sulfonic acid is loaded on the multi-walled carbon nanotube as the catalyst, the surface of the multi-walled carbon nanotube is provided with hydroxyl and carboxyl functional groups formed by oxidation, and the organic titanium is a catalytic assistant.
In the series of embodiments, the mass ratio of the multiwalled carbon nanotube supported 2-amino-5-naphthol-7-sulfonic acid catalyst to the catalytic auxiliary agent is 0.5-1: 0.2-0.3.
In the series of examples, the mass ratio of the multi-walled carbon nanotube to the 2-amino-5-naphthol-7-sulfonic acid is 1: 0.6-0.8.
In the series of embodiments, the titanium catalyst promoter is a combination of cyclopentadienyl titanium trichloride and cyclopentadienyl titanium dibutoxide in any proportion.
The invention further discloses a method for loading the 2-amino-5-naphthol-7-sulfonic acid on the multi-wall carbon nano tube as a catalyst, which comprises the following steps:
(1) adding the multi-walled carbon nano-tube into a mixed solution of concentrated sulfuric acid and concentrated nitric acid, and then ultrasonically dispersing a reaction solution under a heating condition to oxidize the multi-walled carbon nano-tube; after the completion, washing the multi-walled carbon nano-tube, and drying in vacuum to obtain an oxidized multi-walled carbon nano-tube for later use;
(2) adding the prepared solution of the 2-amino-5-naphthol-7-sulfonic acid subjected to dehydration and deoxidation treatment into the oxidized multi-walled carbon nano-tube under the vacuum condition, and condensing and refluxing under the heating condition; and after the reaction is finished, carrying out suction filtration, washing and drying on the product to obtain the carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid catalyst.
In the series of embodiments, in the step (1), the mass ratio of the multi-walled carbon nanotubes to the mixed solution of concentrated sulfuric acid and concentrated nitric acid is 1: 2.5-3. Optionally, the volume ratio of the concentrated sulfuric acid to the concentrated nitric acid is 4: 1.
in the series of embodiments, in the step (1), the length of the multi-wall carbon nanotube is 10-20nm, and the specific surface area is 523m2(g) an inner diameter of 5-8nm and an outer diameter of 12-16nm。
In the series of embodiments, in the step (1), the heating temperature is 40-50 ℃, the ultrasonic dispersion time is 1-1.5h, and the power is 100-500W, preferably 200-500W.
In this series of examples, in step (1), the method for washing and drying the multi-walled carbon nanotubes comprises: washing with distilled water for 5-7 times, and vacuum drying for 12-16 hr.
In this series of examples, in step (2), the conditions of the condensing reflux under the heating condition are as follows: condensing and refluxing for 3-4h at 90-100 ℃.
In the series of embodiments, the step (2) further comprises a step of vacuum degassing the reaction environment before the reflux condensation under heating, wherein the temperature is set to be 100 ℃ and 110 ℃, and the vacuum degassing is carried out for 0.5-1 h.
In this series of examples, step (2) was carried out by heating with an oil bath to provide the energy requirement for the reaction.
In this series of examples, in step (2), the washing and drying methods are as follows: washing with anhydrous ethanol for 2-3 times, and drying in a vacuum drying oven at 80 deg.C.
Thirdly, the invention discloses a method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation, which comprises the following steps: and (2) mixing 3-diethylamino methyl propionate, the carbon nanotube-loaded 2-amino-5-naphthol-7-sulfonic acid catalyst and the organic titanium catalyst promoter, uniformly stirring, adding dried diethylamine, and reacting under a heating condition to obtain the catalyst.
In this series of examples, the diethylamine was dried by molecular sieve dehydration.
In this series of examples, the reaction under heating is: reacting for 10-12h at 90-95 ℃.
In the series of embodiments, the mass ratio of the 3-diethylamino methyl propionate to the carbon nanotube-supported 2-amino-5-naphthol-7-sulfonic acid catalyst to the catalytic assistant is 100:0.5-1: 0.2-0.3.
In this series of examples, the molar ratio of methyl 3-diethylaminopropionate to diethylamine is 1: 1.5-2. In the present invention, since high temperature and high pressure are not required, the amount of diethylamine used can be greatly reduced.
Further, since the 3-diethylamino-N, N-diethyl propionamide obtained after the reaction is completed is a crude product, it is necessary to perform purification by the following steps: adding polymerization inhibitor into the crude product of 3-diethylamino-N, N-diethyl propionamide, and separating and purifying by falling film evaporator at 20-30Pa and 95-105 deg.C.
In the series of examples, the polymerization inhibitor is a mixture of 4, 6-dinitro-2-sec-butyl naphthol and nonyl naphthol in any ratio; optionally, the mass ratio of the two is 1:1.
In the series of examples, the mass ratio of the 3-diethylamino-N, N-diethyl propionamide crude product to the polymerization inhibitor is 100: 1-2.
Finally, the invention discloses the catalyst for synthesizing 3-diethylamino-N, N-diethyl propionamide and the application of the method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation in the fields of chemical industry, medicine and the like.
Compared with the prior art, the invention has the following beneficial effects:
(1) the method adopts the carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid to compound the organic titanium catalyst promoter, and has the advantages of small using amount of the catalyst, high catalytic efficiency, stable product performance, high conversion rate (more than 92 percent) and the like; moreover, the reaction process only needs to be carried out at 90-95 ℃ under normal pressure, and compared with the existing method which needs to be carried out at high temperature and high pressure, the method of the invention has obvious technical advantages.
(2) The invention adopts the carbon nano tube loaded with 2-amino-5-naphthol-7-sulfonic acid as the main amidation catalyst, and the carbon nano tube has large specific surface area, high thermal stability and unique tube cavity structure, can highly disperse catalytic active components, increases the active area and has higher catalytic activity. Different from impregnation loading, the carbon nanotube loaded 2-amino-5-naphthol-7-sulfonic acid is formed by chemically bonding hydroxyl and carboxyl functional groups formed on the surface of the oxidized carbon nanotube with 2-amino-5-naphthol-7-sulfonic acid, and has the advantage of high loading rate, so that the catalytic efficiency and the conversion rate can be remarkably improved while the using amount of a catalyst is reduced.
(3) The invention utilizes cyclopentadienyl titanium trichloride and cyclopentadienyl titanium dibutoxide as organic titanium cocatalyst, has the advantages of high activity and less dosage, can have better catalytic activity without high temperature, and can effectively reduce amidation reaction temperature by matching with carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid, thereby reducing reaction energy consumption and raw material loss.
(4) The method for preparing the 3-diethylamino-N, N-diethyl propionamide through amidation has the advantages of simple process, convenient operation, easy industrial amplification and the like.
Drawings
The accompanying drawings, which are incorporated in and constitute a part of this specification, are included to provide a further understanding of the invention, and are incorporated in and constitute a part of this specification, illustrate exemplary embodiments of the invention and together with the description serve to explain the invention and not to limit the invention.
FIG. 1 is a graph comparing the effects of products prepared in examples 1-3 of the present invention and comparative example 4.
FIG. 2 is a graph comparing the effects of the products prepared in examples 1-3 of the present invention and comparative example 6.
FIG. 3 is a graph comparing the effects of the products prepared in examples 1-3 of the present invention and comparative example 7.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
It is noted that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of exemplary embodiments according to the invention. As used herein, the singular forms "a", "an" and "the" are intended to include the plural forms as well, and it should be understood that when the terms "comprises" and/or "comprising" are used in this specification, they specify the presence of stated features, steps, operations, devices, components, and/or combinations thereof, unless the context clearly indicates otherwise.
Example 1
A method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation comprises the following steps:
(1) 4.5g of multi-walled carbon nanotubes (length 10-20nm, specific surface area 523 m)2Per gram, the inner diameter is 5-8nm, the outer diameter is 12-16nm), pouring the mixture into a three-neck flask with a condenser tube, adding a mixed solution of 9.0g of concentrated sulfuric acid with the mass concentration of 12.6% and 2.25g of concentrated nitric acid with the mass concentration of 22.3%, heating to 40 ℃, performing ultrasonic dispersion for 1 hour with the power of 200W, washing with distilled water for 7 times after the ultrasonic dispersion is finished, and then performing vacuum drying for 12 hours under the conditions of-0.098 Mpa and 80 ℃ to obtain the oxidized multi-walled carbon nanotube.
(2) And transferring the oxidized multi-walled carbon nanotube into a three-neck flask connected with a condenser tube, a vacuum pump and a separating funnel, and placing the three-neck flask in oil bath heating, wherein 10.8g of toluene solution of 2-amino-5-naphthol-7-sulfonic acid with the mass concentration of 25% is obtained in the separating funnel after dehydration and deoxidation treatment. Setting the oil bath temperature at 100 ℃, degassing under-0.09 Mpa for 0.5h, then cutting off a vacuum valve, keeping the vacuum state of the system, opening a bottom valve of a descending separating funnel, transferring the toluene solution of 2-amino-5-naphthol-7-sulfonic acid into a three-neck flask under the vacuum condition, and carrying out condensation reflux for 3h at 90 ℃; and after the reaction is finished, performing suction filtration on the product, washing the product for 3 times by using absolute ethyl alcohol, and drying the product in a vacuum drying oven at the temperature of 80 ℃ to obtain the carbon nano tube supported 2-amino-5-naphthol-7-sulfonic acid catalyst for later use.
(3) Adding 79.5g of 3-diethylamino methyl propionate into a stainless steel reaction kettle with a stirring device, controlling the temperature of jacket heat-conducting oil at 90 ℃, starting the stirring device, controlling the stirring speed at 290r/min, sequentially adding 0.40g of carbon nanotube-loaded 2-amino-5-naphthol-7-sulfonic acid catalyst, 0.08g of cyclopentadienyl titanium trichloride and 0.08g of cyclopentadienyl titanium dibutoxide into the reaction kettle after the temperature is constant, uniformly stirring, adding 54.8g of diethylamine dehydrated and dried by a molecular sieve, and reacting for 10 hours to obtain the crude product of the 3-diethylamino-N, N-diethyl propionamide.
(4) And (3) adding 0.5g of 4, 6-dinitro-2-sec-butyl naphthol and 0.5g of nonyl naphthol into the crude 3-diethylamino-N, N-diethyl propionamide, and separating and purifying by a falling film evaporator under the conditions of 30Pa and 95 ℃ to obtain the product 3-diethylamino-N, N-diethyl propionamide. The conversion rate was calculated to be 93.0% and the pot residue was calculated to be 0.02 g.
Example 2
A method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation comprises the following steps:
(1) 4.5g of multi-walled carbon nanotubes (length 10-20nm, specific surface area 523 m)2Per gram, the inner diameter is 5-8nm, the outer diameter is 12-16nm), pouring into a three-neck flask with a condenser tube, adding a mixed solution of 10.8g of concentrated sulfuric acid with the mass concentration of 12.6% and 2.7g of concentrated nitric acid with the mass concentration of 22.3%, heating to 45 ℃, performing ultrasonic dispersion for 1.2 hours with the power of 300w, washing with distilled water for 5 times, and performing vacuum drying for 14 hours at-0.098 Mpa and 70 ℃; obtaining the oxidized multi-wall carbon nano-tube.
(2) And transferring the oxidized multi-walled carbon nanotube into a three-neck flask connected with a condenser tube, a vacuum pump and a separating funnel, and placing the three-neck flask in oil bath heating, wherein 12.0g of 2-amino-5-naphthol-7-sulfonic acid toluene solution with the concentration of 25% after dehydration and deoxidation treatment is placed in the separating funnel. Setting the oil bath temperature at 105 ℃, degassing under-0.09 Mpa for 0.8h, then cutting off a vacuum valve, keeping the vacuum state of the system, opening a bottom valve of a descending separating funnel, transferring the toluene solution of 2-amino-5-naphthol-7-sulfonic acid into a three-neck flask under the vacuum condition, and carrying out condensation reflux for 3.5h at 95 ℃; and after the reaction is finished, performing suction filtration on the product, washing the product for 2 times by using absolute ethyl alcohol, and drying the product in a vacuum drying oven at the temperature of 80 ℃ to obtain the carbon nano tube supported 2-amino-5-naphthol-7-sulfonic acid catalyst for later use.
(3) Adding 79.5g of 3-diethylamino methyl propionate into a stainless steel reaction kettle with a stirring device, controlling the temperature of jacket heat-conducting oil at 90 ℃, starting the stirring device, controlling the stirring speed at 300r/min, sequentially adding 0.60g of carbon nanotube-loaded 2-amino-5-naphthol-7-sulfonic acid catalyst, 0.11g of cyclopentadienyl titanium trichloride and 0.09g of cyclopentadienyl titanium dibutoxide into the reaction kettle after the temperature is constant, uniformly stirring, adding 68.5g of diethylamine dehydrated and dried by a molecular sieve, and reacting for 11 hours to obtain the crude product of the 3-diethylamino-N, N-diethyl propionamide.
(4) And (3) adding 0.6g of 4, 6-dinitro-2-sec-butyl naphthol and 0.6g of nonyl naphthol into the crude 3-diethylamino-N, N-diethyl propionamide, and separating and purifying by a falling film evaporator under the conditions of 20Pa and 105 ℃ to obtain the product 3-diethylamino-N, N-diethyl propionamide. The conversion was calculated to be 92.1% and the pot residue was 0.04 g.
Example 3
A method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation comprises the following steps:
(1) 4.5g of multi-walled carbon nanotubes (length 10-20nm, specific surface area 523 m)2Per gram, the inner diameter is 5-8nm, the outer diameter is 12-16nm), pouring into a three-neck flask with a condenser tube, adding a mixed solution of 9.6g of concentrated sulfuric acid with the mass concentration of 12.6% and 2.4g of concentrated nitric acid with the mass concentration of 22.3%, heating to 50 ℃, performing ultrasonic dispersion for 1.5 hours with the power of 500w, washing with distilled water for 6 times, and performing vacuum drying for 16 hours at the temperature of-0.098 Mpa and 90 ℃; obtaining the oxidized multi-wall carbon nano-tube.
(2) And transferring the dried multi-walled carbon nano-tube to a three-neck flask connected with a condenser tube, a vacuum pump and a separating funnel, and placing the three-neck flask in oil bath heating, wherein 14.4g of toluene solution of 2-amino-5-naphthol-7-sulfonic acid with the concentration of 25% after dehydration and deoxidation treatment is arranged in the separating funnel. Setting the oil bath temperature at 110 ℃, degassing for 1h under-0.09 Mpa, then cutting off a vacuum valve, keeping the vacuum state of the system, opening a bottom valve of a descending separating funnel, transferring the toluene solution of 2-amino-5-naphthol-7-sulfonic acid into a three-neck flask under the vacuum condition, and carrying out condensation reflux for 4h at 100 ℃; and after the reaction is finished, performing suction filtration on the product, washing the product for 2 times by using absolute ethyl alcohol, and drying the product in a vacuum drying oven at the temperature of 80 ℃ to obtain the carbon nano tube supported 2-amino-5-naphthol-7-sulfonic acid catalyst for later use.
(3) Adding 79.5g of 3-diethylamino methyl propionate into a stainless steel reaction kettle with a stirring device, controlling the temperature of jacket heat-conducting oil at 95 ℃, starting the stirring device, controlling the stirring speed at 300r/min, sequentially adding 0.80g of carbon nanotube-loaded 2-amino-5-naphthol-7-sulfonic acid catalyst, 0.11g of cyclopentadienyl titanium trichloride and 0.12g of cyclopentadienyl titanium dibutoxide into the reaction kettle after the temperature is constant, uniformly stirring, adding 73.0g of diethylamine dehydrated and dried by a molecular sieve, and reacting for 12 hours to obtain the crude product of the 3-diethylamino-N, N-diethyl propionamide.
(4) Adding 1.2g of 4, 6-dinitro-2-sec-butyl naphthol and 1.2g of nonyl naphthol into the crude product of the 3-diethylamino-N, N-diethyl propionamide, and separating and purifying by a falling film evaporator under the conditions of 23Pa and 102 ℃ to obtain the product of the 3-diethylamino-N, N-diethyl propionamide. The conversion was calculated to be 92.8% and the residue was 0.03 g.
Comparative example 1
The procedure of example 1 was repeated except that the carbon nanotube-supported 2-amino-5-naphthol-7-sulfonic acid catalyst was not used.
Comparative example 2
The procedure of example 1 was repeated except that the organic titanium promoter was not used.
Comparative example 3
The procedure of example 1 was repeated except that 2-amino-5-naphthol-7-sulfonic acid was used instead of carbon nanotube-supported 2-amino-5-naphthol-7-sulfonic acid.
Comparative example 4
The procedure of example 1 was repeated except that sodium methoxide was used as a catalyst to replace the carbon nanotube-supported 2-amino-5-naphthol-7-sulfonic acid, cyclopentadienyl titanium trichloride, and cyclopentadienyl titanium dibutoxide.
Comparative example 5
The same procedure as in example 1 was repeated, except that p-toluenesulfonic acid was used as a catalyst in place of carbon nanotube-supported 2-amino-5-naphthol-7-sulfonic acid, cyclopentadienyl titanium trichloride, and cyclopentadienyl titanium dibutoxide.
Comparative example 6
Example 1 was repeated except that 4, 6-dinitro-2-sec-butylnaphthol was not used.
Comparative example 7
The procedure is as in example 1 except that nonylnaphthol is not used.
Performance testing
The conversion, pot residue, etc. of the products prepared in examples 1 to 3 and comparative examples 1 to 7 were calculated, and the results are shown in Table 1. It can be seen that: when only the carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid catalyst is not used, the conversion rate is obviously reduced, and the kettle residue is increased to some extent, as shown in a comparative example 1. When only the organotitanium promoter was not used, the conversion rate was lowered but was slightly higher than that of comparative example 1, see comparative example 2. When 2-amino-5-naphthol-7-sulfonic acid is used for replacing the carbon nano tube to load the 2-amino-5-naphthol-7-sulfonic acid, the conversion rate is reduced to 84.4 percent, the kettle residue is increased to 0.06g, the carrier effect of the carbon nano tube is obvious, and the result is shown in a comparative example 3. When sodium methoxide is used as a catalyst to replace the carbon nano tube loaded with 2-amino-5-naphthol-7-sulfonic acid, cyclopentadienyl titanium trichloride and cyclopentadienyl titanium dibutoxide, the catalytic activity of the sodium methoxide can be reflected at a higher temperature, so that the conversion rate is obviously reduced, and the color of the product is light yellow, as shown in a comparative example 4. The principle is the same as in comparative example 4, when only p-toluenesulfonic acid is used as the catalyst. When the mixture is separated and purified by a falling film evaporator, the polymerization inhibiting effect is better due to the compound use of the 4, 6-dinitro-2-sec-butyl naphthol and the nonyl naphthol, and when only one of the two components is used, the polymerization inhibiting effect is reduced, so that the conversion rate and kettle residue are influenced, the color of the product is greatly influenced, and the product is changed from colorless to dark yellow, which is shown in a comparative example 6 and a comparative example 7. In addition, the change of the color from colorless to light yellow and dark yellow can be seen through the figures 1-3.
TABLE 1
| Conversion rate% | Residue of autoclave, g | Appearance of the product | |
| Example 1 | 93.0 | 0.02 | Colorless and colorless |
| Example 2 | 92.1 | 0.04 | Colorless and colorless |
| Example 3 | 92.8 | 0.03 | Colorless and colorless |
| Comparative example 1 | 84.3 | 0.05 | Colorless and colorless |
| Comparative example 2 | 88.6 | 0.06 | Colorless and colorless |
| Comparative example 3 | 84.4 | 0.06 | Colorless and colorless |
| Comparative example 4 | 76.6 | 0.08 | Light yellow |
| Comparative example 5 | 78.9 | 0.07 | Light yellow |
| Comparative example 6 | 78.0 | 0.08 | Deep yellow |
| Comparative example 7 | 76.1 | 0.12 | Deep yellow |
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (22)
1. The catalyst for synthesizing 3-diethylamino-N, N-diethyl propionamide is characterized by being prepared by compounding a multi-walled carbon nanotube, 2-amino-5-naphthol-7-sulfonic acid and organic titanium, wherein the 2-amino-5-naphthol-7-sulfonic acid is used as a catalyst and loaded on the multi-walled carbon nanotube, the surface of the multi-walled carbon nanotube is provided with hydroxyl and carboxyl functional groups formed by oxidation, and the organic titanium is used as a catalytic auxiliary agent;
the organic titanium catalytic promoter is the combination of cyclopentadienyl titanium trichloride and cyclopentadienyl titanium dibutoxide in any proportion;
the mass ratio of the multi-walled carbon nanotube to the 2-amino-5-naphthol-7-sulfonic acid is 1: 0.6-0.8;
the mass ratio of the multiwalled carbon nanotube-loaded 2-amino-5-naphthol-7-sulfonic acid catalyst to the catalytic auxiliary agent is 0.5-1: 0.2-0.3;
the method for loading the 2-amino-5-naphthol-7-sulfonic acid on the multi-wall carbon nano tube as the catalyst comprises the following steps:
(1) adding the multi-walled carbon nano-tube into a mixed solution of concentrated sulfuric acid and concentrated nitric acid, and then ultrasonically dispersing a reaction solution under a heating condition to oxidize the multi-walled carbon nano-tube; after the completion, washing the multi-walled carbon nano-tube, and drying in vacuum to obtain an oxidized multi-walled carbon nano-tube for later use;
(2) adding the prepared solution of the 2-amino-5-naphthol-7-sulfonic acid subjected to dehydration and deoxidation treatment into the oxidized multi-walled carbon nano-tube under the vacuum condition, and condensing and refluxing under the heating condition; and after the reaction is finished, carrying out suction filtration, washing and drying on the product to obtain the carbon nano tube loaded 2-amino-5-naphthol-7-sulfonic acid catalyst.
2. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 1, wherein in step (1), the mass ratio of the multi-walled carbon nanotubes to the mixed solution of concentrated sulfuric acid and concentrated nitric acid is 1: 2.5-3.
3. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 2, wherein the volume ratio of the concentrated sulfuric acid to the concentrated nitric acid is 4: 1.
4. the catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 1, wherein in step (1), the multi-walled carbon nanotube has a length of 10 to 20nm and a specific surface area of 523m2(ii)/g, the inner diameter is 5-8nm, and the outer diameter is 12-16 nm.
5. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide as claimed in claim 1, wherein in step (1), the heating temperature is 40 to 50 ℃, the ultrasonic dispersion time is 1 to 1.5h, and the power is 100-500W.
6. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide as claimed in claim 5, wherein the power is 200-500W.
7. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 1, wherein in the step (1), the method for washing and drying the multi-walled carbon nanotubes comprises the following steps: washing with distilled water for 5-7 times, and vacuum drying for 12-16 hr.
8. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 1, wherein in the step (2), the conditions of the condensing reflux under heating are as follows: condensing and refluxing for 3-4h at 90-100 ℃.
9. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide as claimed in claim 1, wherein the step (2) further comprises a step of vacuum degassing the reaction environment before the reflux condensation under heating at a temperature of 100 ℃ for 0.5 to 1 hour.
10. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 1, wherein in step (2), the energy requirement for the reaction is provided by means of oil bath heating.
11. The catalyst for synthesizing 3-diethylamino-N, N-diethylpropionamide according to claim 1, wherein in the step (2), the washing and drying methods are as follows: washing with anhydrous ethanol for 2-3 times, and drying in a vacuum drying oven at 80 deg.C.
12. A method for preparing 3-diethylamino-N, N-diethyl propionamide through amidation is characterized by comprising the following steps: mixing 3-diethylamino methyl propionate and the catalyst of any one of claims 1 to 6, stirring uniformly, adding dried diethylamine, and reacting under heating.
13. Amidation process of claim 12 to prepare 3-diethylamino-N, N-diethylpropionamide, wherein the diethylamine is dried by dehydration with molecular sieves.
14. Amidation process of claim 12 to prepare 3-diethylamino-N, N-diethylpropionamide, wherein the reaction under heating is: reacting for 10-12h at 90-95 ℃.
15. The amidation method of claim 12 to prepare 3-diethylamino-N, N-diethyl-propionamide, wherein the mass ratio of methyl 3-diethylaminopropionate, 2-amino-5-naphthol-7-sulfonic acid catalyst supported on carbon nanotubes, and catalyst promoter is 100:0.5-1: 0.2-0.3.
16. Amidation process of claim 12 to prepare 3-diethylamino-N, N-diethylpropionamide, wherein the molar ratio of methyl 3-diethylaminopropionate to diethylamine is 1: 1.5-2.
17. Amidation process of claim 12 to prepare 3-diethylamino-N, N-diethylpropionamide, which further comprises the step of purifying the 3-diethylamino-N, N-diethylpropionamide obtained.
18. Amidation process of claim 17 to prepare 3-diethylamino-N, N-diethylpropionamide, wherein the purification step is: adding polymerization inhibitor into the crude product of 3-diethylamino-N, N-diethyl propionamide, and separating and purifying by falling film evaporator at 20-30Pa and 95-105 deg.C.
19. The amidation process of claim 18 to produce 3-diethylamino-N, N-diethylpropionamide, wherein said polymerization inhibitor is a mixture of 4, 6-dinitro-2-sec-butylnaphthol and nonylnaphthol in any ratio.
20. Amidation process of claim 19 to prepare 3-diethylamino-N, N-diethylpropionamide, wherein the mass ratio of 4, 6-dinitro-2-sec-butylnaphthol to nonylnaphthol is 1:1.
21. The amidation process of claim 18 to prepare 3-diethylamino-N, N-diethyl propionamide, wherein the mass ratio of the crude 3-diethylamino-N, N-diethyl propionamide to the polymerization inhibitor is 100: 1-2.
22. Use of the catalyst for the synthesis of 3-diethylamino-N, N-diethyl propanamide according to any one of claims 1 to 11 and/or the process for the preparation of 3-diethylamino-N, N-diethyl propanamide according to any one of claims 12 to 21 in the chemical and medical fields.
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