CN113461552B - Preparation method of N, N-dimethyl monoethanolamine - Google Patents
Preparation method of N, N-dimethyl monoethanolamine Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
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- 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
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/10—Separation; Purification; Stabilisation; Use of additives
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
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- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
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Abstract
The invention provides a preparation method of N, N-dimethyl monoethanolamine, which comprises the steps of carrying out addition reaction on N, N-dimethyl formamide and methanol under the action of a supported Pd catalyst, then carrying out reduction reaction in a hydrogen atmosphere to generate the N, N-dimethyl monoethanolamine, and separating to obtain a product. The invention has the main advantages that N, N-dimethyl formamide reacts with methanol to prepare N, N-dimethyl monoethanolamine, thus avoiding the use of ethylene oxide, and the supported Pd catalyst has high activity, is not easy to run off, is simple to operate and has good economic benefit.
Description
Technical Field
The invention relates to a method for preparing N, N-dimethyl monoethanolamine, and belongs to the technical field of chemical industry.
Technical Field
N, N-dimethyl-monoethanolamine, also known as N, N-dimethyl-2-hydroxyethylamine, 2-dimethylaminoethanol. Colorless or yellowish liquid with ammonia smell. Can be used as local anesthetic, emulsifier, textile auxiliary agent, fuel oil additive and ion exchange resin, and can be used as catalyst for aqueous epoxy resin group reaction, curing catalyst of single-component moisture curing polyurethane hot melt adhesive, epoxy resin low-temperature curing accelerator and neutralizer of polyurethane foaming adhesive, aqueous epoxy resin emulsion by temperature inversion method and aqueous polyurethane adhesive.
At present, two synthetic methods exist in the industrialized methods of the published patent, literature and manufacturers, one is that ethylene oxide and dimethylamine are taken as raw materials, the dimethylamine is absorbed by water to be saturated, then ethylene oxide is introduced, crude products can be obtained after the reaction of the two, unreacted dimethylamine is heated, driven out and recycled, and residues are subjected to reduced pressure rectification, so that refined products can be obtained; the other is to take dimethylamine and chloroethanol as raw materials, slowly add chloroethanol after the dimethylamine is absorbed by water, and after the reaction is finished, heat to drive out the dimethylamine for recycling, and then obtain the product by rectification under reduced pressure. Dimethylamine is used in the process of preparing N, N-dimethyl monoethanolamine, and is not friendly to the environment, has large taste and is difficult to treat; the flash point of the ethylene oxide is minus 17.7 ℃, so that great potential safety hazards exist; meanwhile, chlorohydrin is a highly toxic drug. Therefore, the research on a new, efficient and environment-friendly preparation method of N, N-dimethyl monoethanolamine has great significance.
Aiming at the defects existing in the process, a novel method for synthesizing N, N-dimethyl monoethanolamine is urgently needed to be developed, and the problems of troublesome post-treatment, low product selectivity, low safety and the like existing in the existing production are overcome.
Disclosure of Invention
The invention aims to provide a preparation method of N, N-dimethyl monoethanolamine, which can effectively reduce the operation steps of post-reaction treatment, avoid the use of ethylene oxide or chloroethanol and reduce potential safety hazards; the three wastes are reduced, the by-product is reduced, and the cost is reduced. The method uses the supported Pd catalyst, is easy to separate, can effectively reduce the operation steps of post-treatment of the reaction, reduces the energy consumption, is environment-friendly, and avoids the problem of environmental pollution.
In order to achieve the above object, the present invention adopts the following technical scheme:
a method for preparing N, N-dimethyl monoethanolamine, comprising: under the action of a supported Pd catalyst, N, N-dimethylformamide and methanol undergo an addition reaction, then undergo a reduction reaction in a hydrogen atmosphere to generate N, N-dimethylmonoethanolamine, and the N, N-dimethylmonoethanolamine is continuously rectified and separated to obtain a product.
The reaction route of the invention is as follows:
in the preparation method, the dosage of the supported Pd catalyst is 15-20wt% relative to N, N-dimethylformamide.
In the preparation method, the molar ratio of N, N-dimethylformamide to methanol is 1:1.4-1:2, preferably 1:1.5-1:1.8.
In the preparation method, firstly, the reaction is carried out for 2 to 4 hours at the temperature of 40 to 50 ℃, then hydrogen is introduced until the reaction pressure is 5 to 9barg, and the reaction is continued for 3 to 7 hours.
In the preparation method, the product rectification can be carried out by adopting a known method, such as a triangular spiral packing, the number of the tower plates is 15-20, the reflux ratio is 1-2, and the pressure is 5-10mmHg.
The second aspect of the invention relates to a supported Pd catalyst used for preparing N, N-dimethylmonoethanolamine.
A supported Pd catalyst expressed as Pd-X/Y, wherein Pd is an active component, X is a ligand, and is selected from one or more of phenol, o-phenylphenol, 2 '-dihydroxybiphenyl, binaphthol, 3, 5-dichlorophenol and propofol, preferably one or more of phenol, 2' -dihydroxybiphenyl, binaphthol and propofol; y is a carrier and is selected from one or more of ordered mesoporous carbon, silicon dioxide, molecular sieve, carbon nanofiber membrane and neutral alumina, preferably one or more of ordered mesoporous carbon, 4A molecular sieve, carbon nanofiber membrane and silicon dioxide.
In the catalyst of the invention, based on the total weight of the catalyst (calculated by the total amount of Pd+X+Y), the mass fraction of Pd is 18-30%, the mass fraction of X is 25-37%, and the mass fraction of Y is 35-56%; preferably, the mass fraction of Pd is 20-25%, the mass fraction of X is 30-35%, and the mass fraction of Y is 40-50%.
The invention also provides a preparation method of the catalyst, which is realized by the following scheme:
in the invention, the preparation method of the supported Pd catalyst comprises the following steps:
(1) Mixing Pd-containing compound and ligand X in water, stirring at 35-65deg.C, and dispersing carrier Y in the above water solution to obtain suspension;
(2) Dropwise adding an alkaline precipitant into the slurry until the pH value of the slurry is 9.5-12.5, and aging to obtain slurry; the temperature is controlled to be 35-45 ℃ in the dropping process;
(3) And (3) carrying out post-treatment on the slurry to obtain the supported Pd catalyst.
In the method for preparing the catalyst, the amount of water used in the step (1) is not particularly limited, and the Pd-containing compound and the X-containing compound to be added may be completely dissolved.
In the preparation method of the catalyst, in the step (1), the Pd-containing compound is selected from one or more of palladium acetate, palladium chloride, palladium nitrate, palladium sulfate and palladium trifluoroacetate, preferably one or more of palladium acetate, palladium chloride, palladium nitrate and palladium trifluoroacetate.
In the preparation method of the catalyst, in the step (2), the alkaline precipitant is one or more selected from sodium hydroxide, lithium hydroxide, potassium carbonate and sodium carbonate, and the alkaline precipitant can be an aqueous solution with the concentration of 15-35 wt%; the aging time is 1.5-4.5h, and the aging temperature is 50-95 ℃.
In the preparation method of the catalyst, in the step (3), the post-treatment specifically includes: filtering and washing the slurry to obtain a filter cake, drying, and roasting, crushing and tabletting the filter cake. Wherein the drying temperature is 106-126 ℃ and the drying time is 9-19h; the roasting temperature is 323-433 ℃, and the roasting time is 6-17h.
The invention has the beneficial effects that:
1. the invention has the advantages of simple process route, simple operation and low raw material cost; avoiding the potential safety hazard caused by using ethylene oxide and chloroethanol.
2. The prepared supported Pd catalyst, the carrier and the organic ligand are introduced to greatly improve the dispersity of metal atoms in the active center of the catalyst; the lone pair electrons on O in the catalyst framework form coordination bonds with Pd, and the concentration of reactants on the surface of the catalyst is increased in the process of catalytic reaction of the catalyst, so that the catalytic efficiency is high.
3. The supported Pd catalyst is environment-friendly and is easy to separate.
4. The invention can produce N, N-dimethyl monoethanolamine at lower operating temperature, the raw material conversion rate reaches over 96%, and the product selectivity is over 95%.
Detailed Description
The present invention will be described in further detail with reference to the following examples, but the scope of the present invention is not limited to these examples.
Gas chromatographic analysis conditions of the product: island jin gas chromatograph, RTX-DB-5 column, 5 ℃/min rise to 100 ℃; raising the temperature to 200 ℃ at 10 ℃/min; 20 ℃/min is raised to 240 ℃ and maintained for 5min.
The instrument sources in the following examples are shown in table 1 below:
TABLE 1
| Instrument and reagent | Source | Specification of specification |
| ICP spectrometer | Agilent | ICP-OES 720 type |
| Gas chromatograph | Shimadzu (Shimadzu) | GC-2014C |
| Nuclear magnetic resonance spectrometer | Bruker | Advance Bruker 400M |
Unless otherwise indicated, the inorganic salts used in the examples below are all commercially available.
Example 1
Mixing 112.26g palladium acetate and 79.82g phenol into 500g distilled water, heating to 35 ℃, stirring and fully mixing, adding 133.03g ordered mesoporous carbon (Nanjing Xianfeng nano material technology Co., ltd.) under stirring, and mixing to obtain a suspension A; dissolving sodium hydroxide in water to prepare 35wt% sodium hydroxide solution which is an alkaline precipitant B, respectively heating the suspension A and the alkaline precipitant B to 35 ℃, slowly dripping the alkaline precipitant B into the suspension A until the pH value of the system is 9.5, and controlling the reaction temperature of the precipitation process to 35 ℃; then aging for 4.5 hours at 50 ℃ to obtain slurry; the slurry is filtered, washed by deionized water, and the filter cake is dried for 19 hours at 106 ℃, and is roasted for 17 hours at 433 ℃, and the catalyst 1 is obtained after crushing and tabletting molding.
ICP analysis shows that in the catalyst 1, the following components account for the total mass of the catalyst 1 (namely, the total mass of Pd+ligand+carrier, the following are the same) according to the mass (if no special mark exists, the crystallization water of the metal salt raw material is not counted, the organic matters and the carrier are not lost, the following are the same): pd 20%, phenol 30% and carrier 50%.
Example 2
177.33g of palladium chloride and 149.96g of 2,2' -dihydroxybiphenyl are mixed in 1000g of distilled water, the temperature is raised to 45 ℃ and the materials are stirred and fully mixed, 227.356 g of 4A molecular sieve (carbofuran) is added under the stirring state and mixed to obtain suspension A; dissolving lithium hydroxide in water to prepare 35wt% lithium hydroxide solution which is an alkaline precipitant B, respectively heating the suspension A and the alkaline precipitant B to 40 ℃, slowly dripping the alkaline precipitant B into the suspension A until the pH value of the system is 10.5, and controlling the reaction temperature in the precipitation process to 40 ℃; then aging for 3.5 hours at 70 ℃ to obtain slurry; the slurry is filtered, washed by deionized water, and the filter cake is dried for 16 hours at 112 ℃, and is baked for 14 hours at 400 ℃, and the catalyst 2 is obtained after crushing and tabletting molding.
The ICP analysis proves that in the catalyst 2, the following components account for the total mass of the catalyst 2 in percentage by mass: pd 22%, 2' -dihydroxybiphenyl 31% and carrier 47%.
Example 3
115.22g of palladium nitrate and 76.34g of binaphthol are mixed in 1000g of distilled water, the temperature is raised to 55 ℃ and the mixture is stirred and fully mixed, 101.79g of carbon nanofiber membrane (Qingdao Polynatto technology Co., ltd.) is added under stirring and mixed to obtain suspension A; dissolving potassium carbonate into water to prepare 35wt% potassium carbonate solution which is an alkaline precipitant B, respectively heating the suspension A and the alkaline precipitant B to 45 ℃, slowly dripping the alkaline precipitant B into the suspension A until the pH value of the system is 11.5, and controlling the reaction temperature in the precipitation process to 45 ℃; then aging for 2 hours at 85 ℃ to obtain slurry; the slurry is filtered, washed by deionized water, and the filter cake is dried for 11 hours at 116 ℃, and baked for 9 hours at 363 ℃, and the catalyst 3 is obtained after crushing and tabletting molding.
The ICP analysis determines that in the catalyst 3, the following components account for the total mass of the catalyst 3 according to mass percent: pd 23%, binaphthol 33% and carrier 44%.
Example 4
166.23g of palladium trifluoroacetate and 74.49g of propofol are mixed in 1000g of distilled water, the temperature is raised to 65 ℃ and the mixture is stirred and fully mixed, 85.14g of silicon dioxide (carbofuran) is added under stirring and mixed to obtain suspension A; dissolving sodium carbonate in water to prepare 35wt% sodium carbonate solution which is an alkaline precipitant B, respectively heating the suspension A and the alkaline precipitant B to 40 ℃, slowly dripping the alkaline precipitant B into the suspension A until the pH value of the system is 12.5, and controlling the reaction temperature in the precipitation process to 40 ℃; then aging for 1.5 hours at 95 ℃ to obtain slurry; the slurry is filtered, washed by deionized water, and the filter cake is dried for 9 hours at 126 ℃, and baked for 17 hours at 323 ℃, and the catalyst 4 is obtained after crushing and tabletting molding.
The ICP analysis determines that in the catalyst 4, the following components account for the total mass of the catalyst 4 in percentage by mass: pd 25%, propofol 35% and carrier 40%.
Example 5
Catalyst 1 (21.93 g,15 wt%) was charged into a reaction vessel equipped with a mechanical stirrer, thermocouple, condenser, N-dimethylformamide (146.18 g,2 mol) and methanol (96.12 g,3 mol) were introduced into the reaction vessel, and then the reaction vessel was warmed to 40℃and reacted for 4 hours. Then hydrogen gas was passed through for 5barg and the reaction was continued for 7 hours. Filtering to remove solid catalyst after the reaction is finished, separating out reaction liquid, rectifying the obtained crude mixture, adopting triangular spiral packing with the tray number of 18 and the reflux ratio of 1.5 and the pressure of 8mmHg to obtain the product N, N-dimethyl monoethanolamine of 134-136 ℃/760mmHg, and confirming that the product is N, N-dimethyl monoethanolamine through nuclear magnetism.
Results of nuclear magnetic analysis of the product:
1 H NMR(CDCl 3 ,400MHz):δ4.16(s,1H),3.42(t,J＝7.1Hz,2H),2.82(s,6H),2.53(t,J＝7.0Hz,2H).
example 6
Catalyst 2 (24.85 g,17 wt%) was charged into a reaction vessel equipped with a mechanical stirrer, thermocouple, condenser, N-dimethylformamide (146.18 g,2 mol) and methanol (102.53 g,3.2 mol) were introduced into the reaction vessel, and then the reaction vessel was warmed to 45℃and reacted for 3 hours. Then hydrogen gas was passed through at 7barg and the reaction was continued for 6 hours. Filtering to remove the solid catalyst after the reaction is finished, separating out the reaction liquid, rectifying the obtained crude mixture, and obtaining the product N, N-dimethyl monoethanolamine with the column plate number of 18, the reflux ratio of 1.5 and the pressure of 8mmHg at 134-136 ℃/760 mmHg.
Example 7
Catalyst 3 (27.77 g,19 wt%) was charged into a reaction vessel equipped with a mechanical stirrer, thermocouple, condenser, N-dimethylformamide (146.18 g,2 mol) and methanol (108.94 g,3.4 mol) were introduced into the reaction vessel, and then the reaction vessel was warmed to 50℃and reacted for 4 hours. Then hydrogen gas was introduced at 8barg and the reaction was continued for 5 hours. Filtering to remove the solid catalyst after the reaction is finished, separating out the reaction liquid, rectifying the obtained crude mixture, and obtaining the product N, N-dimethyl monoethanolamine with the column plate number of 18, the reflux ratio of 1.5 and the pressure of 8mmHg at 134-136 ℃/760 mmHg.
Example 8
Catalyst 4 (29.24 g,20 wt%) was charged into a reaction vessel equipped with a mechanical stirrer, thermocouple, condenser, N-dimethylformamide (146.18 g,2 mol) and methanol (115.34 g,3.6 mol) were introduced into the reaction vessel, and then the reaction vessel was warmed to 50℃and reacted for 2 hours. Then hydrogen gas was passed through at 9barg and the reaction was continued for 3 hours. Filtering to remove the solid catalyst after the reaction is finished, separating out the reaction liquid, rectifying the obtained crude mixture, and obtaining the product N, N-dimethyl monoethanolamine with the column plate number of 18, the reflux ratio of 1.5 and the pressure of 8mmHg at 134-136 ℃/760 mmHg.
The corresponding chromatographic analysis and calculation results for examples 5-8 are shown in Table 2:
TABLE 2
| Catalyst | Conversion of N, N-dimethylformamide% | N, N-dimethylmonoethanolamine selectivity% |
| 1 | 97 | 95 |
| 2 | 98 | 97 |
| 3 | 97 | 96 |
| 4 | 99 | 98 |
Comparative example 1:
68g dimethylamine aqueous solution (0.5 mol) is added into a 250ml autoclave, after the nitrogen in the autoclave is replaced for 3 times, 44g (1 mol) of ethylene oxide is filled into the autoclave, the autoclave is at normal pressure, the temperature is raised to 80 ℃ for reaction, nitrogen is filled into the autoclave during the reaction, the reaction pressure is maintained to be about 1.5MPa, and the reaction time is 2 hours. After the reaction is finished, pumping the reaction kettle to about-0.3 MPa by a vacuum pump, then flushing nitrogen to normal pressure, and replacing for 3 times; meanwhile, the tail gas of the vacuum pump is connected into a 10wt% sodium bicarbonate alkali liquor absorption bottle. Finally, collecting the obtained reaction liquid, distilling the reaction liquid under reduced pressure, and obtaining the product N, N-dimethyl monoethanolamine with the tower plate number of 15, the reflux ratio of 1.5 and the pressure of 8mmHg at 134-136 ℃/760 mmHg. The dimethylamine conversion was 100% and the N, N-dimethylmonoethanolamine selectivity was 82.1%.
Claims (13)
1. The preparation process of N, N-dimethyl monoethanolamine includes the addition reaction of N, N-dimethyl formamide and methanol in the presence of supported Pd catalyst, reduction reaction in hydrogen atmosphere to produce N, N-dimethyl monoethanolamine, and separation to obtain the product; the supported Pd catalyst is expressed as Pd-X/Y, wherein X is a ligand selected from one or more of phenol, o-phenylphenol, 2' -dihydroxybiphenyl, binaphthol, 3, 5-dichlorophenol and propofol;
y is a carrier and is selected from one or more of ordered mesoporous carbon, silicon dioxide, molecular sieve, carbon nanofiber membrane and neutral alumina.
2. The process according to claim 1, wherein the catalyst is used in an amount of 15 to 20% by weight relative to the N, N-dimethylformamide.
3. The method according to claim 1, wherein the molar ratio of N, N-dimethylformamide to methanol is 1:1.4-1:2.
4. A process according to claim 3, wherein the molar ratio of N, N-dimethylformamide to methanol is from 1:1.5 to 1:1.8.
5. The process according to any one of claims 1 to 4, wherein the conditions for the addition reaction are reaction at a reaction temperature of 40 to 50 ℃ for 2 to 4 hours.
6. The process according to any one of claims 1 to 4, wherein the reduction reaction conditions are hydrogen gas to a reaction pressure of 5 to 9barg and the reaction is continued for 3 to 7 hours.
7. The method according to any one of claims 1 to 4, wherein X is a ligand selected from one or more of phenol, 2' -dihydroxybiphenyl, binaphthol, propofol; y is a carrier and is selected from one or more of ordered mesoporous carbon, 4A molecular sieve, carbon nanofiber membrane and silicon dioxide.
8. The method according to claim 1, wherein the mass fraction of Pd is 18-30%, the mass fraction of X is 25-37% and the mass fraction of Y is 35-56%, based on the total weight of the catalyst.
9. The method according to claim 8, wherein the mass fraction of Pd is 20-25%, the mass fraction of X is 30-35%, and the mass fraction of Y is 40-50%, based on the total weight of the catalyst.
10. The method according to claim 1, 8 or 9, wherein the method for preparing the catalyst comprises the steps of:
(1) Mixing Pd-containing compound and ligand X in water, stirring and fully mixing at 35-65deg.C, and dispersing carrier Y in the above water solution to obtain suspension;
(2) Adding an alkaline precipitant into the suspension until the pH value is 9.5-12.5, and aging to obtain slurry;
(3) And (3) carrying out post-treatment on the slurry to obtain the supported Pd catalyst.
11. The method of claim 10, wherein in step (1), the Pd-containing compound is selected from one or more of palladium acetate, palladium chloride, palladium nitrate, palladium sulfate, and palladium trifluoroacetate; and/or the number of the groups of groups,
in the step (2), the alkaline precipitant is one or more selected from sodium hydroxide, lithium hydroxide, potassium carbonate and sodium carbonate.
12. The method of claim 11, wherein in step (1), the Pd-containing compound is selected from one or more of palladium acetate, palladium chloride, palladium nitrate, and palladium trifluoroacetate.
13. The method of claim 10, wherein the aging time is 1.5 to 4.5 hours and the aging temperature is 50 to 95 ℃; and/or the number of the groups of groups,
in step (3), the post-treatment specifically includes: filtering and washing the slurry to obtain a filter cake, drying, and roasting, crushing and tabletting the filter cake; wherein the drying temperature is 106-126 ℃ and the drying time is 9-19h; the roasting temperature is 323-433 ℃, and the roasting time is 6-17h.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09268163A (en) * | 1996-04-04 | 1997-10-14 | Mitsui Toatsu Chem Inc | Production of 2-(dimethylamino)ethanol |
| CN101648880A (en) * | 2009-08-27 | 2010-02-17 | 王宇平 | Preparation method of N, N-dimethylethanolamine |
| WO2012080409A1 (en) * | 2010-12-17 | 2012-06-21 | Basf Se | Process for preparing an n,n-dialkylethanolamine having high colour stability |
| CN102557960A (en) * | 2010-12-28 | 2012-07-11 | 苏州飞翔新材料研究院有限公司 | Method for producing alkyl alcohol amine |
| CN103071534A (en) * | 2012-12-31 | 2013-05-01 | 浙江江山化工股份有限公司 | Catalyst for catalytically synthesizing N-methyl ethanol amine compound and application thereof |
| CN105503616A (en) * | 2015-12-21 | 2016-04-20 | 浙江工业大学 | Catalytic synthesis method of N-substituent ethanolamine compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201904612D0 (en) * | 2019-04-02 | 2019-05-15 | Univ Leuven Kath | Reaction of glycoladehyde |
-
2021
- 2021-07-08 CN CN202110770396.8A patent/CN113461552B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09268163A (en) * | 1996-04-04 | 1997-10-14 | Mitsui Toatsu Chem Inc | Production of 2-(dimethylamino)ethanol |
| CN101648880A (en) * | 2009-08-27 | 2010-02-17 | 王宇平 | Preparation method of N, N-dimethylethanolamine |
| WO2012080409A1 (en) * | 2010-12-17 | 2012-06-21 | Basf Se | Process for preparing an n,n-dialkylethanolamine having high colour stability |
| CN102557960A (en) * | 2010-12-28 | 2012-07-11 | 苏州飞翔新材料研究院有限公司 | Method for producing alkyl alcohol amine |
| CN103071534A (en) * | 2012-12-31 | 2013-05-01 | 浙江江山化工股份有限公司 | Catalyst for catalytically synthesizing N-methyl ethanol amine compound and application thereof |
| CN105503616A (en) * | 2015-12-21 | 2016-04-20 | 浙江工业大学 | Catalytic synthesis method of N-substituent ethanolamine compound |
Non-Patent Citations (3)
| Title |
|---|
| Enhanced Product Selectivity in Continuous N-Methylation of Amino Alcohols over Solid Acid±Base Catalysts with Supercritical Methanol;Tomoharu Oku 等;《Angew. Chem. Int. Ed.》;第41卷(第18期);第3476-3479页 * |
| RANEY® nickel-catalyzed reductive N-methylation of amines with paraformaldehyde: theoretical and experimental study;Xin Ge 等;《RSC Adv.》;第4卷;第43195-43203页 * |
| 二烷基乙醇胺的应用及合成工艺研究进展;王磊 等;《安徽科技学院学报》;第31卷(第5期);第88-94页 * |
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