CN106316868B - A kind of synthetic method of bis- (2- dimethylaminoethyl) ethers - Google Patents
A kind of synthetic method of bis- (2- dimethylaminoethyl) ethers Download PDFInfo
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- 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
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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
- C07C213/04—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reaction of ammonia or amines with olefin oxides or halohydrins
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Abstract
The present invention relates to a kind of synthetic methods of bis- (2- dimethylaminoethyl) ethers, belong to organic high molecular compound technical field.In a high pressure reaction kettle, dimethylamine and reacting ethylene oxide molar ratio are 1:2-2.2, and reaction temperature is 60-100 DEG C, react 2-5h, cure 0.5-1h；Add catalyst Cu-Ni/ γ-Al2O3, pressure in kettle is adjusted to 1.5~2.5MPa with hydrogen, temperature is controlled at 190~220 DEG C, and control reaction pressure reacts 6-13h in 10-25MPa；It after pressure is down to 1.0MPa, leads in the middle part of de- amine/hydrogen tower, for the dimethylamine and hydrogen in mixture from de- amine/hydrogen top of tower discharge, bis- (2- dimethylaminoethyl) the ether crude products for taking off amine/hydrogen tower bottom are evaporated under reduced pressure separation.The application is produced applied to polyethers, has many advantages, such as utilization rate of equipment and installations height, high production efficiency.
Description
Technical field
The present invention relates to a kind of synthetic methods of bis- (2- dimethylaminoethyl) ethers, belong to organic high molecular compound technology
Field.
Background technique
Bis- (2- dimethylaminoethyl) ethers, molecular formula C8H20N2O, appearance is light yellow transparent liquid, it can be infinitely dissolved in water,
Aqueous solution is suitable for almost all foam plastic products as efficient tertiary amine catalyst in alkalinity, bis- (dimethylaminoethyl) ethers
Production, be important one of the amines catalyst of polyurethane industries among others.It is mainly used for the production of flexible foam product, is particularly suitable for height
Rebound and RIM product.Its structural formula is as follows:
Mainly using 2- dimethylethanolamine or derivatives thereof etherification reaction preparation occurs for general patent document report
Several preparation methods about bis- (2- dimethylaminoethyl) ethers are as follows in bis- (2- dimethylaminoethyl) ethers:
A. patent US3084675 reports one kind using toluene as solvent, with 2- dimethylamino chloroethanes (hereinafter referred to as chlorination
Object) it is etherified with 2-dimethylaminoethanol sodium, wherein 2-dimethylaminoethanol sodium is with sodium hydroxide and 2- dimethylethanolamine
It is prepared in toluene, the hydrochloride of chloride is neutralized with sodium hydroxide and extracted by toluene, product yield 67%.This method
Major defect is: with the presence of water in neutralization reaction, will cause chloride hydrolysis；The preparation of sodium alkoxide, reaction time are long；And it uses
In sodium hydrate aqueous solution and chloride hydrochloride, wastewater flow rate are big；Toluene had not only been used as solvent but also had been extractant, recovery processing amount
Greatly.
B. patent US417721 discloses a kind of one pot reaction, with 2-dimethylaminoethanol sodium and 2- dimethylethanolamine
For raw material, chlorosulfonic acid, thionyl chloride and sulfonic acid chloride is added and is reacted as chlorination reagent, using long chain alkane as solvent, receives
Rate is 54%.This method major defect is: chlorine-containing compound post-processing is complicated, and by-product is more.
C. a kind of method being catalyzed with sulfur trioxide vapor, yield 63-68% are reported in patent US4474988.It should
Method major defect is: sulfur trioxide feed way is cumbersome, and sulfur trioxide is unfriendly to environment.
D. patent US6150559 reports one kind using 2- dimethylethanolamine as raw material, using solid base zeolite catalyst
The continuous reaction of catalysis, at 400 DEG C of reaction temperature, yield 25%.This method major defect is: reaction temperature is high,
Select poor, yield is relatively low.
E. patent CN102452946 reports a kind of with trimethylamine aqueous solution and bis- (2- chloroethyl) ethers reaction generation double seasons
Ammonium salt chloride is added triphenylphosphine, is warming up to 140-160 DEG C of reaction 6-10h, obtains the bis- (2- bis- of product under nitrogen protection
Methylaminoethyl) ether and methyl triphenyl phosphonium chloride.This method major defect is: preparation method low efficiency, post-processing are compared
Complexity, and phosphorus is unfriendly to environment.
F. patent CN102786427 reports three-step approach preparation method, and the first step is sub- by 2- dimethylethanolamine and dichloro
Sulfone reaction generates chloride, and 2- dimethylethanolamine is reacted generation sodium alkoxide by second step with metallic sodium, and third step is for quaternary ammonium salt
Etherification reaction occurs for chloride and sodium alkoxide under the action of class catalyst, then carries out rectification under vacuum to product.This method mainly lacks
Point is: chloride post-processing is complicated, and by-product is more, and pollution is big.
These occur etherification reaction using 2- dimethylethanolamine or derivatives thereof and prepare bis- (2- dimethylaminoethyl) ethers,
All there is more shortcoming and defect, such as: chloride, sulfide etc. increase the difficulty of post-processing in reaction process, while right
Environment has a great impact.In addition, 2- dimethylethanolamine or derivatives thereof often occurs the hair of side reaction during the reaction
It is raw, it is the main problem of method therefor so far so as to cause yield reduction.
Based on this, the application is made.
Summary of the invention
To solve defect and deficiency present in existing preparation method, specially design one it is entirely different with existing route
Prepare synthetic route.The route that the present invention designs is that two-step method synthesizes bis- (2- dimethylaminoethyl) ethers, method particularly includes:
Step 1: the synthesis of 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol；
Step 2: 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol and dimethylamine synthesize bis- (2- under the effect of the catalyst
Dimethylaminoethyl) ether.
Wherein the first step can refine are as follows: a. charging, b. synthetic reaction, c. post-processing；Second step is subdivided into: a. charging,
B. synthetic reaction, c. take off amine/hydrogen, d. rectifying.
Its reaction equation is as follows:
Step 1:
Step 2:
Two-step method synthesizes bis- (2- dimethylaminoethyl) ethers and is specifically synthetically prepared that steps are as follows:
The first step, the synthesis of 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol:
A. dimethylamine and reacting ethylene oxide dimethylamine and reacting ethylene oxide under conditions of catalyst is not added, reaction
Molar ratio is that 1:2-2.5 (considers that ratio should be 1:2, but in view of that can remain a certain amount of epoxy second in pipeline from principle
Alkane, so ethylene oxide can be slightly excessive in practice), the preceding air in nitrogen replacement reaction kettle of reaction, displacement 3 times, instead
Answering temperature is 60-100 DEG C, reacts 2-5h, curing 0.5-1h is (after curing temperature generally foundation reaction curing, when anti-in 5min
When answering kettle pressure almost unchanged, it is considered that reaction terminates, to determine curing time, generally 30-40min), after reaction
Obtain 2- (2- (dimethylamino) ethyoxyl) ethanol product.
B.2- (2- (dimethylamino) ethyoxyl) ethyl alcohol post-processing carries out in a high pressure reaction kettle, in 100-120 DEG C of temperature
The lower degassing 0.5-2h of degree (degassing, the mainly ethylene oxide of water and traces of unreacted a small amount of in removal reaction product), cooling
It discharges to 30-60 DEG C.
Second step, 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol and dimethylamine synthesize bis- (2- under the effect of the catalyst
Dimethylaminoethyl) ether:
A. it charges: by catalyst Cu-Ni/ γ-Al2O3It is fitted into autoclave, and by dimethylamine, 2- (2- (dimethyl
Amino) ethyoxyl) ethyl alcohol pours into reaction kettle.
B. synthetic reaction: hydrogen is passed through in reaction kettle, pressure is adjusted to 1.5~2.5MPa with hydrogen, temperature control exists
190~220 DEG C, reaction pressure control is in 10-25MPa, reaction time 6-13h, until reaction terminates to obtain containing bis- (2- diformazans
Base aminoethyl) ether mixture.
C. it takes off amine/hydrogen: pressure is down to by the mixture containing bis- (2- dimethylaminoethyl) ethers by pressure reducing valve
0.8-1.5MPa leads to mixture in the middle part of de- amine/hydrogen tower, and column bottom temperature controls the diformazan in 130-160 DEG C, mixture
Amine and hydrogen by having been preheated with dry gas in 70-90 DEG C of drying tower, then will from de- amine/hydrogen top of tower discharge
Dimethylamine and hydrogen mixed gas are passed through condenser and separate two kinds of gases, and it is stand-by that lower layer's dimethylamine liquid is discharged into recycling can, upper layer
It is stand-by that hydrogen is pumped into hydrogen recycling can.Remaining de- amine/hydrogen tower bottom is exactly bis- (2- dimethylaminoethyl) ether crude products.
D. rectifying: by treated, bis- (2- dimethylaminoethyl) ether crude products loading rectifying columns carry out vacuum distillation separation
(2- dimethylaminoethyl) ether products bis- out.
Meanwhile synthesis 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol and bis- (2- dimethylaminoethyl) ethers in the present invention
Autoclave can carry out in same reaction kettle, to have saved the cost of equipment.
When being carried out in same reaction kettle, preparation step are as follows: first synthesize 2- (2- (dimethyl in a high pressure reaction kettle
Amino) ethyoxyl) ethyl alcohol is cooled to 30-60 DEG C by 100-120 DEG C of degassing 0.5-2h, as synthesizing bis- (2- in next step
Dimethylaminoethyl) ether raw material, following step is according to the charging in second step, synthetic reaction, de- amine/hydrogen, rectifying
Four steps complete the preparation of bis- (2- dimethylaminoethyl) ethers.
The invention has the following advantages:
(1) ether is compared with other preparation methods for two-step method synthesis bis- (2- dimethylaminoethyls), during the reaction without chlorination
The introducing of object, sulfide greatly reduces the difficulty of post-processing, reduces the influence to environment.
(2) addition of catalyst is not needed in the method for preparing 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol, and is produced
Product post-processing can be completed in a kettle, easy to operate.
(3) in entire reaction process hydrogen recycle and the recycling of dimethylamine, improve the benefit of raw material
With the conversion ratio of rate and product.
(4) synthesis 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol and bis- (2- dimethylaminoethyl) ethers can be same
Reaction kettle carries out corresponding reaction, has saved the cost of equipment.
Detailed description of the invention
Fig. 1 is the synthesis flow schematic diagram of 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol in the application；
Fig. 2 is the synthesis flow schematic diagram of bis- (2- dimethylaminoethyl) ethers in the application.
Specific embodiment
Embodiment 1: two-step reaction is in differential responses kettle
The first step, the synthesis of 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol:
A. dimethylamine and reacting ethylene oxide dimethylamine and reacting ethylene oxide under conditions of catalyst is not added, reaction
Molar ratio is 1:2.1, with the air in nitrogen replacement reaction kettle before reacting, is replaced 3 times, and reaction temperature is 90 DEG C, reacts 3h,
0.5h is cured, 2- (2- (dimethylamino) ethyoxyl) ethanol product is obtained after reaction.
B.2- (2- (dimethylamino) ethyoxyl) ethyl alcohol post-processing carries out in a high pressure reaction kettle, at a temperature of 100 DEG C
Deaerate 1h, is cooled to 60 DEG C of dischargings.
Second step, the preparation of bis- (2- dimethylaminoethyl) ethers:
A. it charges: by catalyst Cu-Ni/ γ-Al2O3It is fitted into autoclave, and by dimethylamine, 2- (2- (dimethyl
Amino) ethyoxyl) ethyl alcohol pours into reaction kettle.
B. synthetic reaction: hydrogen is passed through in reaction kettle, pressure is adjusted to 2MPa with hydrogen, temperature is controlled at 210 DEG C, instead
Answering pressure is about 16MPa, reaction time 9h, until reaction terminates to obtain the mixture containing bis- (2- dimethylaminoethyl) ethers.
C. it takes off amine/hydrogen: pressure is down to by the mixture containing bis- (2- dimethylaminoethyl) ethers by pressure reducing valve
1.0MPa leads to mixture in the middle part of de- amine/hydrogen tower, and column bottom temperature controls the dimethylamine and hydrogen at 145 DEG C, in mixture
From the discharge of de- amine/hydrogen top of tower, by having been preheated with dry gas in 80 DEG C of drying tower, then by dimethylamine and hydrogen
Gaseous mixture is passed through condenser and separates two kinds of gases, and it is stand-by that lower layer's dimethylamine liquid is discharged into recycling can, and upper layer hydrogen is pumped into hydrogen
Recycling can is stand-by.Remaining de- amine/hydrogen tower bottom is exactly bis- (2- dimethylaminoethyl) ether crude products.
D. rectifying: will treated that bis- (2- dimethylaminoethyl) ether crude products are fitted into rectifying column be evaporated under reduced pressure and divide
Separate out bis- (2- dimethylaminoethyl) ether products.
Product is light yellow transparent liquid, product purity 99.65%, yield 74.51%.
Embodiment 2: two-step reaction carries out in same reaction kettle
Synthesis 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol can be same anti-with bis- (2- dimethylaminoethyl) ethers
Kettle is answered to carry out corresponding reaction, method is as follows:
When carrying out in same reaction kettle, preparation method and condition are same as Example 1, the first step, in reaction under high pressure
2- (2- (dimethylamino) ethyoxyl) ethyl alcohol is synthesized in kettle, by 110 DEG C of degassing 1h, as conjunction in next step when being cooled to 30 DEG C
The raw material of (2- dimethylaminoethyl) ether in pairs.
Next second step is carried out fully according to the second step in embodiment 1.
Product is light yellow transparent liquid, purity 99.58%, yield 74.46%.Different height are used from embodiment 1
Product made from pressure reaction kettle is compared, and quality and yield have saved the cost of equipment almost without difference.
Embodiment 3-12
The preparation method of embodiment 3-12 is same as Example 1, is different from place and is: to the first step and second step
Key reaction temperature and pressure control point carries out preferably, concrete condition such as table 1- table 3.
Influence of the reaction temperature to product in 1 first step of table
Can be observed how from table 1: reaction temperature has a certain impact to product yield, reaction time in the first step, with
The raising of reaction temperature in the first step, the reaction time in the first step shortens therewith, product yield increases；But when reaction
Temperature be 100 DEG C when, product colour be it is light yellow, yield also starts to reduce, this may be due to reaction temperature raising lead to pair
Caused by reaction occurs, therefore it may determine that and show that reacting optimum temperature in the first step is 90 DEG C, temperature-controllable range is 80-90
℃。
Influence of the reaction temperature to product in 2 second step of table
Can be observed how from table 2: reaction temperature has significantly product yield, reaction pressure and reaction time in second step
It influences, with the raising of the reaction temperature in second step, the reaction pressure in second step is increased, the reaction time contracts therewith
Short, product yield increases；But when temperature is 220 DEG C, pressure 19MPa, product yield is 210 DEG C compared with reaction temperature
Product yield only increase by 0.08%, pressure is but higher by 3MPa, therefore, it is determined that showing that the reaction temperature optimum value in second step is
220℃。
H in 3 second step of table2Influence of the initial pressure to product
It can be observed how from table 3: H in second step2It is equal to product yield, reaction pressure and reaction time to originate reaction pressure
It has a significant impact, with H in second step2The raising of reaction pressure is originated, the reaction pressure of second step increases, the reaction time
Shorten therewith, product yield increases；But it can also be seen that working as H from table 32Originate reaction pressure be 2.0MPa and
When 2.5MPa, the yield difference of product almost very little, but pressure is raised particularly evident, wherein H2Originating reaction pressure is
When 2.5MPa, reaction pressure is up to 21MPa, under the premise of influencing less on product yield, for the sake of production safety, the
H in two steps2Starting reaction pressure optimum value is 2.0MPa.
Two-step method provided herein synthesizes bis- (2- dimethylaminoethyl) ethers and compared with other preparation methods, is reacting
In the process without the introducing of chloride, sulfide, the difficulty of post-processing is greatly reduced, reduces the influence to environment；Meanwhile
The addition that catalyst is not needed in the method for 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol is prepared, and product post-processing is being reacted
It can be completed in kettle, it is easy to operate；And in entire reaction process hydrogen recycle and the recycling of dimethylamine,
Improve the utilization rate of raw material and the conversion ratio of product；Synthesize 2- (2- (dimethylamino) ethyoxyl) ethyl alcohol and bis- (2- diformazans
Base aminoethyl) ether can carry out in two reaction kettles, and corresponding reaction can also be carried out in same reaction kettle, save equipment
Cost, efficiently solve in existing method and technique the problems such as three-protection design is difficult, product yield is low, of poor quality.
The above content is the preferred embodiments of combination the invention to further detailed made by provided technical solution
Describe in detail bright, and it cannot be said that the invention specific implementation is confined to these above-mentioned explanations, technology affiliated for the invention
For the those of ordinary skill in field, without departing from the concept of the premise of the invention, several simple deductions can also be made
Or replacement, it all shall be regarded as belonging to the protection scope of the invention.
Claims (5)
1. a kind of synthetic method of bis- (2- dimethylaminoethyl) ethers, it is characterised in that: be made of following two step:
(1) 2-(2-(dimethylamino) ethyoxyl) ethyl alcohol synthesis: dimethylamine and reacting ethylene oxide obtain 2-(2-(diformazan
Base amino) ethyoxyl) ethanol product；
(2) bis- (2- dimethylaminoethyl) ether synthesis:
A. it charges: 2 O 3 of catalyst Cu-Ni/ γ-Al is fitted into autoclave, and by dimethylamine and step (1)
Synthesized 2-(2-(dimethylamino) ethyoxyl) ethyl alcohol pours into reaction kettle；
B. synthetic reaction: reacting kettle inner pressure is adjusted to 1.5~2.5MPa with hydrogen, temperature controls the control at 190~220 DEG C
Reaction pressure processed reacts 6-13h in 10-25MPa, until reaction terminates to obtain the mixing containing bis- (2- dimethylaminoethyl) ethers
Object；
C. it takes off amine/hydrogen: after the mixture pressure containing bis- (2- dimethylaminoethyl) ethers is down to 0.8-1.5MPa, leading to
In the middle part of de- amine/hydrogen tower, it is surplus to take off amine/hydrogen tower bottom from de- amine/hydrogen top of tower discharge for dimethylamine and hydrogen in mixture
Under be exactly bis- (2- dimethylaminoethyl) ether crude products；
D. rectifying: by step c, treated that bis- (2- dimethylaminoethyl) ether crude products are packed into rectifying columns is evaporated under reduced pressure
Isolate bis- (2- dimethylaminoethyl) ether products；
The dimethylamine and hydrogen after drying, is passed through condenser and separates two kinds of gases, lower layer's dimethylamine liquid is discharged into back
Closed cans is stand-by, and it is stand-by that upper layer hydrogen is pumped into hydrogen recycling can；
The step (1) and step (2) is carried out with kettle, synthesis technology are as follows: in a high pressure reaction kettle, dimethylamine and ethylene oxide
Reaction molar ratio is 1:2-2.2, and reaction temperature is 60-100 DEG C, reacts 2-5h, cures 0.5-1h；Add catalyst
Pressure in kettle is adjusted to 1.5~2.5MPa with hydrogen by 2 O 3 of Cu-Ni/ γ-Al, and temperature controls the control at 190~220 DEG C
Reaction pressure reacts 6-13h in 10-25MPa；It after pressure is down to 1.0MPa, leads in the middle part of de- amine/hydrogen tower, two in mixture
From de- amine/hydrogen top of tower discharge, bis- (2- dimethylaminoethyl) ether crude products of de- amine/hydrogen tower bottom subtract for methylamine and hydrogen
Pressure distillation separation.
2. the synthetic method of bis- (2- dimethylaminoethyl) ethers of one kind as described in claim 1, it is characterised in that: step
(1) in, 2-(2-(dimethylamino) ethyoxyl) ethanol product synthesis condition are as follows: dimethylamine and reacting ethylene oxide molar ratio
Example is 1:2-2.5, and reaction temperature is 60-100 DEG C, reacts 2-5h, cures 0.5-1h.
3. the synthetic method of bis- (2- dimethylaminoethyl) ethers of one kind as described in claim 1, it is characterised in that: step
(1) in, synthesized 2-(2-(dimethylamino) ethyoxyl) ethyl alcohol deaerates at a temperature of 100-120 DEG C after 0.5-2h,
It is cooled to 30-60 DEG C, it is spare.
4. the synthetic method of bis- (2- dimethylaminoethyl) ethers of one kind as described in claim 1, it is characterised in that: described
Drying temperature is 70-90 DEG C.
5. the synthetic method of bis- (2- dimethylaminoethyl) ethers of one kind as described in claim 1, it is characterised in that: step c
In, column bottom temperature is controlled at 130-160 DEG C, makes bis- (2- dimethylaminoethyl) ether crude products and dimethylamine and Hydrogen Separation.
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| 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 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101405256A (en) * | 2006-03-20 | 2009-04-08 | 巴斯夫欧洲公司 | Process for preparing N,N-dimethylaminoethoxyethanol |
| WO2010139521A1 (en) * | 2009-06-02 | 2010-12-09 | Huntsman Corporation Hungary Zrt. | A method for providing a secondary or tertiary amine |
| CN103261130A (en) * | 2010-12-17 | 2013-08-21 | 巴斯夫欧洲公司 | Process for preparing an N,N-ialkylethanolamine having high colour stability |
| CN103450035A (en) * | 2013-07-30 | 2013-12-18 | 苏州环科新材料有限公司 | Preparation method of bis(2-dimethyl aminoethyl) ether |
| CN105837457A (en) * | 2016-03-30 | 2016-08-10 | 河北华茂伟业科技有限公司 | Method for synthesizing bis(dimethylaminoethyl)ether under catalysis of metal catalyst |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3957875A (en) * | 1974-06-10 | 1976-05-18 | Union Carbide Corporation | Synthesis of bis[2-(N,N-dimethylamino)ethyl] ether |
| BE530219A (en) * | 1976-05-14 | |||
| DE3422610A1 (en) * | 1984-06-19 | 1985-12-19 | Basf Ag, 6700 Ludwigshafen | METHOD FOR PRODUCING AMINES |
| DE3724239A1 (en) * | 1987-07-22 | 1989-02-02 | Basf Ag | METHOD FOR PRODUCING ALIPHATIC N, N-DIALKYL SUBSTITUTED AMINO ALCOHOLS |
| HU219183B (en) * | 1997-07-15 | 2001-02-28 | Huntsman Corporation Hungary Vegyipari Termelő-Fejlesztő Részvénytársaság | Process for the preparation of n-methylated compounds by reductive methylation |
| DE19859776B4 (en) * | 1998-12-23 | 2008-06-19 | Basf Se | Process for the preparation of amines |
| US7169268B2 (en) * | 2002-06-26 | 2007-01-30 | Huntsman Petrochemical Corporation | Color stabilization of amines |
| DE102004023529A1 (en) * | 2004-05-13 | 2005-12-08 | Basf Ag | Process for the continuous production of an amine |
| US8791302B2 (en) * | 2010-12-17 | 2014-07-29 | Basf Se | Process for preparing an N,N-dialky-ethanolamine having high color stability |
-
2016
- 2016-08-19 CN CN201610697504.2A patent/CN106316868B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101405256A (en) * | 2006-03-20 | 2009-04-08 | 巴斯夫欧洲公司 | Process for preparing N,N-dimethylaminoethoxyethanol |
| WO2010139521A1 (en) * | 2009-06-02 | 2010-12-09 | Huntsman Corporation Hungary Zrt. | A method for providing a secondary or tertiary amine |
| CN103261130A (en) * | 2010-12-17 | 2013-08-21 | 巴斯夫欧洲公司 | Process for preparing an N,N-ialkylethanolamine having high colour stability |
| CN103450035A (en) * | 2013-07-30 | 2013-12-18 | 苏州环科新材料有限公司 | Preparation method of bis(2-dimethyl aminoethyl) ether |
| CN105837457A (en) * | 2016-03-30 | 2016-08-10 | 河北华茂伟业科技有限公司 | Method for synthesizing bis(dimethylaminoethyl)ether under catalysis of metal catalyst |
Non-Patent Citations (1)
| Title |
|---|
| 一缩乙二醇法合成BDMAEE和DMAEE;王婧祎;《聚氨酯工业》;20051231;第20卷(第1期);第41-42页 |
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