CN108084040A - The synthetic method of the double amino-ethyl ethers of N, N, N '-trimethyl-N '-ethoxy - Google Patents

The synthetic method of the double amino-ethyl ethers of N, N, N '-trimethyl-N '-ethoxy Download PDF

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CN108084040A
CN108084040A CN201810008673.XA CN201810008673A CN108084040A CN 108084040 A CN108084040 A CN 108084040A CN 201810008673 A CN201810008673 A CN 201810008673A CN 108084040 A CN108084040 A CN 108084040A
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trimethyl
ethoxys
ethyl ethers
double amino
synthetic method
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CN108084040B (en
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陈新志
魏梦怡
钱超
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Zhejiang University ZJU
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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
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • 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
    • C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention discloses a kind of N, N, the synthetic method of the double amino-ethyl ethers of N' trimethyl N' ethoxys comprises the following steps：In solvent I, using dimethylaminoethoxyethanol as raw material, in 2,2,6,6 tetramethyl piperidine oxides FeCl3Under nitrite tert-butyl catalyst system and catalyzing, through dioxygen oxidation into 2 [2 (dimethylamino) ethyoxyl] acetaldehyde；In solvent II, N methylethanolamines are mixed with 2 [2 (dimethylamino) ethyoxyl] acetaldehyde, using Raney Ni as catalyst, hydroamination is carried out in this, as reaction system, N, N, the double amino-ethyl ethers of N' trimethyl N' ethoxys are made.N, N are synthesized using the above method, the double amino-ethyl ethers of N' trimethyl N' ethoxys have the characteristics that concise in technology, at low cost, high income, pollution are few.

Description

The synthetic method of the double amino-ethyl ethers of N, N, N '-trimethyl-N '-ethoxy
Technical field
The invention belongs to polyurethane industrial, relate generally to a kind of synthesis of catalysts for polyurethanes, i.e. N, N, N'- trimethyls- The synthetic method of the double amino-ethyl ethers of N'- ethoxys.
Background technology
The double amino-ethyl ethers of N, N, N'- trimethyl-N'- ethoxys, belong to low smell kicker, its is main at present Synthetic method has：
1st, patent JP2009215386 and CN101104674 reports one kind with N, N, N'- trimethyls-bis- amino-ethyls ether N, the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys are made for raw material, but N, N, N'- trimethyl-bis- amino-ethyls ether come Source is inconvenient, is unfavorable for the industrialized production of this method.And this method prepares target product with above-mentioned raw materials and acrylonitrile reactor, third Alkene nitrile severe toxicity, environment are unfriendly.
2nd, patent CN105884629 reports one kind using dimethylethanolamine and N methyldiethanol amine as raw material, through chlorine Change and nucleophilic displacement of fluorine is made N, N, the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, this method is needed to consume substantial amounts of alkali, made Large quantity of exhaust gas is generated with thionyl chloride, Atom economy is low, and nucleophilic displacement of fluorine needs the sodium hydroxide of equivalent to be generated as acid binding agent The salt of equivalent, and the salt post processing generated is complicated, it is of high cost；Application value is little in industrial production.
The content of the invention
The technical problem to be solved in the present invention is to provide a kind of concise in technology, at low cost, high income, few N, N are polluted, The synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys.
In order to solve the above technical problem, the present invention provides a kind of N, N, the double amino-ethyls of N'- trimethyl-N'- ethoxys The synthetic method of ether, comprises the following steps：
1), in solvent I, using dimethylaminoethoxyethanol as raw material, in 2,2,6,6- tetramethyl piperidine oxides- FeCl3Under-nitrite tert-butyl catalyst system and catalyzing, through dioxygen oxidation into 2- [2- (dimethylamino) ethyoxyl] acetaldehyde；
The 2,2,6,6- tetramethyl piperidine oxides：Nitrite tert-butyl=1.5~2:1 mass ratio, FeCl3：2, 2,6,6- tetramethyl piperidine oxides=0.9~1.1：1 mass ratio；
2,2,6,6- tetramethyl piperidine oxides account for 7~12% of the dimethylaminoethoxyethanol quality as raw material (preferably 9~10%)；
Oxygen pressure is 0.4~0.8MPa, and oxidizing reaction temperature is 70~90 DEG C, and oxidation time is 5~10h；
2), in solvent II, by N- methylethanolamines and 2- [2- (dimethylamino) ethyoxyl] acetaldehyde according to 1~1.2: The 1 molar ratio molar ratio of aldehyde (amine with) mixes, using Raney Ni (Raney's nickel) as catalyst, in this, as reaction system into N, N, the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys are made in row hydroamination；
The Raney Ni account for the 5~20% of 2- [2- (dimethylamino) ethyoxyl] acetaldehyde weight, Hydrogen Vapor Pressure 1.5 ~2.5MPa, temperature are 100~140 DEG C, and the reaction time is 7~9h (being, for example, 8h).
As the N of the present invention, N, the improvement of the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys：
In the step 2), formic acid is added in above-mentioned reaction system, is hydrogenated with again after adjusting the pH=1 of reaction system Amination.
As the N of the present invention, N, the improvement of the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys：
In the step 2), sodium acid carbonate is added in above-mentioned reaction system, adjust reaction system pH=9~13 (compared with Good is 11~13) after carry out hydroamination again.
As the N of the present invention, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys further changes Into：
In the step 1), solvent I is dichloromethane, dichloroethanes, toluene, n-hexane, Ethyl formate；
In the step 2), solvent II is methanol.
As the N of the present invention, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys further changes Into：
Following post processing is carried out to the gains (kettle liquid) of step 1) oxidation reaction：Gains are cooled to mistake after room temperature Filter, gained filtrate decompression are distilled (remove solvent I), obtain 2- [2- (dimethylamino) ethyoxyl] acetaldehyde (water white transparency liquid Body).
As the N of the present invention, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys further changes Into：
In the step 1), oxygen pressure 0.6MPa, oxidizing reaction temperature is 80 DEG C, reaction time 8h；2,2,6, 6- tetramethyl piperidine oxides account for 9.4% of the dimethylaminoethoxyethanol quality as raw material；
The 2,2,6,6- tetramethyl piperidine oxides：Nitrite tert-butyl=1.515:1 mass ratio；
FeCl3：2,2,6,6- tetramethyl piperidine oxides=1：1 mass ratio.
As the N of the present invention, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys further changes Into：
Hydroamination is cooled to room temperature after reaction, filtering；Filtrate decompression rectifying obtains N, N, N'- trimethyl-N'- hydroxyls The double amino-ethyl ethers of ethyl；
Filter cake input, which (is put into) immediately in strong caustic (mass concentration >=40%, until saturation), impregnates at least 30 Minute, then it is 8 ± 0.2 to be washed with clear water to cleaning solution pH, obtains Raney Ni (can be recycled).
Method used in the present invention is that the raw material dimethylaminoethoxyethanol being easy to get first is oxidized to aldehyde, the oxidation process Oxygen is oxidant, and Atom economy is high, and pollution is small；It aoxidizes products therefrom and carries out hydroamination in N- methylethanolamines, it is acyclic Border is polluted, and Atom economy is high.
Specifically, N of the invention, N, the preparation method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, are wrapped successively Include following two steps：
1), using dimethylaminoethoxyethanol as raw material, intermediate product 2- [2- (dimethylamino) second is made in catalysis oxidation Oxygroup] acetaldehyde.
Catalytic oxidation technique process is：Dimethylaminoethoxyethanol, 2,2,6,6- tetramethyl piperazines are put into autoclave Pyridine oxide, nitrite tert-butyl, FeCl3With solvent (dichloromethane etc.).Certain oxygen pressure, is heated in holding system It is stirred to react.
2), N, N is made in 2- [2- (dimethylamino) ethyoxyl] acetaldehyde and N- methylethanolamine hydroaminations obtained, The double amino-ethyl ethers of N'- trimethyl-N'- ethoxys.
Being catalyzed reduction amination process is：2- [2- (dimethylamino) ethyoxyl] acetaldehyde, N- methyl are put into autoclave Ethanolamine, Raney Ni and methanol (as solvent)；Hydrogen pressure is kept in kettle, is heated to being stirred to react.
The synthetic method of the present invention has following technical advantage：
1st, 2,2,6,6- tetramethyl piperidine oxides-FeCl3- nitrite tert-butyl catalyst system and catalyzing cacodyl oxide amino ethoxy Base ethyl alcohol, compared with traditional Jones reagent oxidation and the oxidation of crome metal reagent, the system is nontoxic and pollution-free, meets greenization It learns.
2nd, catalyst Raney Ni can be recycled, and environmental pollution is small, and atom utilization is high.
3rd, raw material, oxidant cost are low, and toxicity is low；
4th, two-step reaction atom high income, economy is high, does not generate the three wastes, environmentally protective.
5th, the hydroamination reaction of aldehyde and N- methylethanolamines with sodium acid carbonate adjust pH, can improve feed stock conversion and Product yield.
Specific embodiment
With reference to specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in This.
The synthetic method of embodiment 1, a kind of 2- [2- (dimethylamino) ethyoxyl] acetaldehyde, with Dimethylaminoethoxy second Alcohol is raw material, 2,2,6,6- tetramethyl piperidine oxides-FeCl3- nitrite tert-butyl is catalyzed：
13.3g dimethylaminoethoxyethanols, 1.248g2,2,6,6- tetramethyl piperidine oxygen are put into 100ml autoclaves Compound, 0.824g nitrite tert-butyls, 1.248gFeCl3With 15ml dichloromethane.
It is oxygenated into kettle to 0.6MPa at room temperature, is heated to 80 DEG C and is stirred to react 8h.Room temperature is down to after reaction, this When kettle in pressure be 0.2MPa (20 DEG C).Then kettle liquid is post-processed as follows：Filtering, the distillation of gained filtrate decompression (pressure of 25Torr collects 75~80 DEG C of fraction) obtains 2- [2- (dimethylamino) ethyoxyl] second of 8.02g water white transparencies Aldehyde.It is 95.0% to the conversion ratio that raw material is obtained after kettle liquid progress gas chromatographic analysis after reaction, product yield is 61.2%.
Embodiment 1-1~embodiment 1-9
Change the following reaction condition in embodiment 1：Change reaction temperature, the reaction pressure in embodiment 1, catalyst ratio Example (changes the mass ratio of 2,2,6,6- tetramethyl piperidine oxides and nitrite tert-butyl, the oxidation of 2,2,6,6- tetramethyl piperidines The dosage of object remains unchanged), the species of solvent；Remaining is equal to 1 (FeCl of embodiment3Amount ratio remain unchanged)；So as to To embodiment 1-1~1-9, gained total recovery is shown in Table 1.
Table 1
Following reaction condition in embodiment 1-10~1-17, change embodiment 1：Change embodiment 1 in reaction time, 2,2,6,6- tetramethyl piperidine oxides of catalyst account for the dimethylaminoethoxyethanol mass ratio as raw material, remaining is equal to (that is, 2, the mass ratio of 2,6,6- tetramethyl piperidine oxides and nitrite tert-butyl remains unchanged embodiment 1, FeCl3With 2,2, The mass ratio of 6,6- tetramethyl piperidine oxides remains unchanged)；So as to obtain embodiment 1-10~1-17, gained total recovery is shown in Table 2。
Table 2
Embodiment 2,2- [2- (dimethylamino) ethyoxyl] acetaldehyde and methylethanolamine hydroamination prepare N, N, N'- tri- The double amino-ethyl ethers of methyl-N'- ethoxys：
13.1g (0.1mol) 2- [2- (dimethylamino) ethyoxyl] acetaldehyde, 8.3g are put into 100ml autoclaves (0.1mol) N- methylethanolamines, 1.3gRaney Ni and 15ml methanol.(about 20 DEG C) are flushed with hydrogen gas into kettle extremely at room temperature 2.0MPa is heated to 120 DEG C and is stirred to react 8h, and pressure (being adjusted by hydrogen) is in 2.0~2.2MPa in holding kettle.
Room temperature is down to after reaction, is filtered.Gained filter cake puts into strong caustic (mass concentration 40% immediately Sodium hydrate aqueous solution) in impregnate at least 30 minutes, then with clear water wash repeatedly (to cleaning solution pH be 8 or so), gained Raney Ni can be recycled.Filtrate gas chromatographic analysis, feed stock conversion is 73.7% at this time.Filtrate is depressurized Obtained after rectifying (pressure of 25Torr collects 110~115 DEG C of fraction) 11.63g colourless transparent liquids N, N, N'- trimethyl- The double amino-ethyl ethers of N'- ethoxys, calculate, and the product yield for obtaining step reaction is 61.2%.
Embodiment 3, acid condition hydroamination
Change the charging content in embodiment 2, i.e., 13.1g2- [2- (dimethylamino) second is put into 100ml autoclaves Oxygroup] acetaldehyde, 8.3gN- methylethanolamines, the pH=of 1.3gRaney Ni, 15ml methanol and 0.3g formic acid, at this time reaction system 1, remaining is the same as embodiment 2.It is 76.3% to obtain feed stock conversion after reaction, product yield 63.6%.
Embodiment 4, alkaline condition hydroamination
Change the charging content in embodiment 2, i.e., 13.1g2- [2- (dimethylamino) second is put into 100ml autoclaves Oxygroup] acetaldehyde, 8.3gN- methylethanolamines, 1.3gRaney Ni (as catalyst) and 15ml methanol and add in sodium acid carbonate The pH=11 of (about 0.8g), at this time reaction system, remaining is the same as embodiment 2.Reaction terminate feed stock conversion be 93.3%, product Yield is 90.6%.
Embodiment 4-1~embodiment 4-7
Change the reaction condition in embodiment 4, that is, change reaction temperature, the reaction pressure in embodiment 4, raw material amine ratio (change the molar ratio of N- methylethanolamines and 2- [2- (dimethylamino) ethyoxyl] acetaldehyde, 2- [2- (dimethylamino) ethoxies Base] dosage of acetaldehyde remains unchanged), catalyst amount (presses the percentage of 2- [2- (dimethylamino) ethyoxyl] acetaldehyde quality It calculates)；Remaining is equal to embodiment 4 (that is, the pH=11 for controlling reaction system), so as to obtain embodiment 4-1~embodiment 4-7, Gained total recovery is shown in Table 3.
Table 3
Remarks explanation：2- [2- (dimethylamino) ethyoxyl] acetaldehyde is prepared according to 1 the method for embodiment, so as to obtain Total recovery described in table 3.
Embodiment 5-1, sodium acid carbonate dosage in embodiment 5 is increased, until adjusting the pH=13 of reaction system；Remaining is equivalent In embodiment 5.Product yield is 88.3%.
Embodiment 5-2, sodium acid carbonate dosage in embodiment 4 is reduced, until adjusting the pH=9 of reaction system；Remaining is equivalent In embodiment 4.Product yield is 78.9%.
The recycling of embodiment 6, catalyst Raney Ni：
1.3gRaney Ni separating obtained in embodiment 4 are substituted to original 1.3gRaney Ni, remaining is equal to reality Apply example 4.
Above-mentioned repetitive cycling use is repeated 4 times；The result of gained is described in table 4 below.
Table 4
1.248gFeCl in comparative example 1-1, cancellation embodiment 13Use, remaining is the same as embodiment 1.Product yield is 12.0%.
Comparative example 1-2, by the FeCl in embodiment 13Make the green vitriol of same molar into, remaining is the same as implementation Example 1.The conversion ratio of raw material is 30.7%, product yield 8.8%.
Comparative example 1-3, cancel embodiment 1 in " 0.824g nitrite tert-butyls " use, remaining is the same as embodiment 1.It is former The conversion ratio of material is 39.9%, product yield 11.5%.
Comparative example 1-4, the sodium nitrite that the nitrite tert-butyl in embodiment 1 is made into same molar, remaining is the same as real Apply example 1.The conversion ratio of raw material is 50.7%, product yield 28.8%.
0.8g sodium acid carbonates in embodiment 4 are made into saleratus by comparative example 2, and the dosage of saleratus is anti-to adjust Answer the pH=11 of system (with embodiment 4)；Remaining is equal to embodiment 4.
Feed stock conversion is 88.9%, product yield 60.8%.
Finally, it should also be noted that exemplified as above is only several specific embodiments of the invention.Obviously, the present invention not It is limited to above example, also very many deformations.Those of ordinary skill in the art can directly lead from present disclosure All deformations for going out or associating, are considered as protection scope of the present invention.

Claims (7)

  1. The synthetic method of the double amino-ethyl ethers of 1.N, N, N'- trimethyl-N'- ethoxys, it is characterized in that comprising the following steps：
    1), in solvent I, using dimethylaminoethoxyethanol as raw material, in 2,2,6,6- tetramethyl piperidine oxides-FeCl3- Under nitrite tert-butyl catalyst system and catalyzing, through dioxygen oxidation into 2- [2- (dimethylamino) ethyoxyl] acetaldehyde；
    The 2,2,6,6- tetramethyl piperidine oxides：Nitrite tert-butyl=1.5~2:1 mass ratio, FeCl3：2,2,6,6- Tetramethyl piperidine oxides=0.9~1.1：1 mass ratio；
    2,2,6,6- tetramethyl piperidine oxides account for 7~12% of the dimethylaminoethoxyethanol quality as raw material；
    Oxygen pressure is 0.4~0.8MPa, and oxidizing reaction temperature is 70~90 DEG C, and oxidation time is 5~10h；
    2), in solvent II, by N- methylethanolamines and 2- [2- (dimethylamino) ethyoxyl] acetaldehyde according to 1~1.2:1 Mixed in molar ratio using Raney Ni as catalyst, carries out hydroamination in this, as reaction system, N, N, N'- front threes is made The double amino-ethyl ethers of base-N'- ethoxys；
    The Raney Ni account for the 5~20% of 2- [2- (dimethylamino) ethyoxyl] acetaldehyde weight, Hydrogen Vapor Pressure for 1.5~ 2.5MPa, temperature are 100~140 DEG C, and the reaction time is 7~9h.
  2. 2. N according to claim 1, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, feature It is：
    In the step 2), formic acid is added in above-mentioned reaction system, hydrogenation amine is carried out again after adjusting the pH=1 of reaction system Change.
  3. 3. N according to claim 1, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, feature It is：
    In the step 2), sodium acid carbonate is added in above-mentioned reaction system, is carried out again after adjusting pH=9~13 of reaction system Hydroamination.
  4. 4. according to any N of claims 1 to 3, N, the synthesis side of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys Method, it is characterized in that：
    In the step 1), solvent I is dichloromethane, dichloroethanes, toluene, n-hexane, Ethyl formate；
    In the step 2), solvent II is methanol.
  5. 5. N according to claim 4, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, feature It is：
    Following post processing is carried out to the gains of step 1) oxidation reaction：It is filtered after gains are cooled to room temperature, gained filter Liquid is evaporated under reduced pressure, and obtains 2- [2- (dimethylamino) ethyoxyl] acetaldehyde.
  6. 6. N according to claim 5, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, feature It is：
    In the step 1), oxygen pressure 0.6MPa, oxidizing reaction temperature is 80 DEG C, reaction time 8h；2,2,6,6- tetra- Methyl piperidine oxide accounts for 9.4% of the dimethylaminoethoxyethanol quality as raw material；
    The 2,2,6,6- tetramethyl piperidine oxides：Nitrite tert-butyl=1.515:1 mass ratio；
    FeCl3：2,2,6,6- tetramethyl piperidine oxides=1：1 mass ratio.
  7. 7. N according to claim 5, N, the synthetic method of the double amino-ethyl ethers of N'- trimethyl-N'- ethoxys, feature It is：
    Hydroamination is cooled to room temperature after reaction, filtering；Filtrate decompression rectifying obtains N, N, N'- trimethyl-N'- ethoxys Double amino-ethyl ethers；
    It is impregnated at least 30 minutes in filter cake input strong caustic, then it is 8 ± 0.2 to be washed with clear water to cleaning solution pH, is obtained Raney Ni。
CN201810008673.XA 2018-01-04 2018-01-04 Synthesis method of N, N, N '-trimethyl-N' -hydroxyethyl bisaminoethylether Expired - Fee Related CN108084040B (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116283616A (en) * 2023-02-17 2023-06-23 恒光新材料(江苏)股份有限公司 Method for co-producing ZF-10 and BDMAEE
CN117065103A (en) * 2023-08-18 2023-11-17 河南省健琪医疗器械有限公司 Nanometer antibacterial material for tracheal cannula and preparation method thereof

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Publication number Priority date Publication date Assignee Title
HU204764B (en) * 1989-10-11 1992-02-28 Nitroil Vegyipari Termeloe Fej Process for n-alkylation of aliphatic amines or aminoalcohols
CN104341313A (en) * 2013-08-02 2015-02-11 史小鸣 Synthesis of N,N,N'-trimethyl-N'-hydroxyethyl diethyl ether
CN105348353A (en) * 2015-10-01 2016-02-24 浙江大学 Method for preparing 24-keto steroid

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
HU204764B (en) * 1989-10-11 1992-02-28 Nitroil Vegyipari Termeloe Fej Process for n-alkylation of aliphatic amines or aminoalcohols
CN104341313A (en) * 2013-08-02 2015-02-11 史小鸣 Synthesis of N,N,N'-trimethyl-N'-hydroxyethyl diethyl ether
CN105348353A (en) * 2015-10-01 2016-02-24 浙江大学 Method for preparing 24-keto steroid

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116283616A (en) * 2023-02-17 2023-06-23 恒光新材料(江苏)股份有限公司 Method for co-producing ZF-10 and BDMAEE
CN116283616B (en) * 2023-02-17 2024-03-22 恒光新材料(江苏)股份有限公司 Method for co-producing ZF-10 and BDMAEE
CN117065103A (en) * 2023-08-18 2023-11-17 河南省健琪医疗器械有限公司 Nanometer antibacterial material for tracheal cannula and preparation method thereof
CN117065103B (en) * 2023-08-18 2024-04-02 河南省健琪医疗器械有限公司 Nanometer antibacterial material for tracheal cannula and preparation method thereof

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