CN106316868A - Bis(2-dimethylaminoethyl)ether synthesis method - Google Patents
Bis(2-dimethylaminoethyl)ether synthesis method 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
- 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 invention belongs to the technical field of organic macromolecular compounds and relates to a bis(2-dimethylaminoethyl)ether synthesis method. The method includes subjecting dimethylamine and ethylene oxide to reaction in a high-pressure reactor, wherein a mole ratio is 1:2-2.2, a reaction temperature is 60-100 DEG C, reaction time is 2-5 hours, and curing time is 0.5-1 hour; adding a catalyst Cu-Ni/gamma-Al2O3, adopting hydrogen for adjusting an internal pressure of the reactor to 1.5-2.5 MPa, controlling the temperature at 190-220 DEG C, controlling a reaction pressure to be 10-25 MPa, and reacting for 6-13h; after the pressure drops to 1.0 MPa, feeding to the middle of an amine/hydrogen removal tower to discharge the dimethylamine and the hydrogen in the mixture from the top of the amine/hydrogen removal tower, and subjecting a crude product of bis(2-dimethylaminoethyl)ether at the bottom of the amine/hydrogen removal tower to reduced pressure distillation and separation. The bis(2-dimethylaminoethyl)ether synthesis method is applied to polyether preparation and has advantages of high equipment utilization rate, high preparation efficiency and the like.
Description
Technical field
The present invention relates to the synthetic method of a kind of double (2-dimethylaminoethyl) ether, belong to organic high molecular compound technology
Field.
Background technology
Double (2-dimethylaminoethyl) ether, molecular formula C8H20N2O, outward appearance is light yellow transparent liquid, can infinitely be dissolved in water,
Aqueous solution is alkalescence, and double (dimethylaminoethyl) ether, as efficient tertiary amine catalyst, is suitable for almost all foam plastic products
Production, be one of important amines catalyst of polyurethane industries among others.It is mainly used in the production of flexible foam goods, is particularly suitable for height
Resilience and RIM goods.Its structural formula is as follows:
General patent document is reported, mainly uses 2-dimethylethanolamine or derivatives thereof generation etherification reaction and prepares
Double (2-dimethylaminoethyl) ether, is as follows several the preparation methoies about double (2-dimethylaminoethyl) ether:
A. patent US3084675 reports a kind of with toluene as solvent, with 2-dimethylamino ethyl chloride (hereinafter referred to as chlorination
Thing) it is etherified with DMAE sodium, wherein DMAE sodium is with sodium hydroxide and 2-dimethylethanolamine
Preparing in toluene, muriatic hydrochlorate sodium hydroxide is neutralized and is extracted by toluene, and product yield is 67%.The method
Major defect is: neutralize in reaction with the presence of water, chloride can be caused to hydrolyze；The preparation of sodium alkoxide, the response time is long；And use
In sodium hydrate aqueous solution and chloride hydrochloride, wastewater flow rate is big；Toluene not only as solvent but also be extractant, recycling amount
Greatly.
B. patent US417721 discloses a kind of one pot reaction, with DMAE sodium and 2-dimethylethanolamine
For raw material, add chlorosulfonic acid, thionyl chloride and sulfonic acid chloride and react as chlorination reagent, using long chain alkane as solvent, receive
Rate is 54%.The method major defect is: chlorine-containing compound post processing is complicated, and by-product is more.
C. reporting a kind of method with sulfur trioxide vapor catalysis in patent US4474988, yield is 63-68%.Should
Method major defect is: sulfur trioxide feed way is loaded down with trivial details, and sulfur trioxide is unfriendly to environment.
D. patent US6150559 reports a kind of with 2-dimethylethanolamine as raw material, uses solid base zeolite catalyst
The continuous reaction of catalysis, at reaction temperature 400 DEG C, yield is 25%.The method major defect is: reaction temperature is high,
Selecting poor, yield is on the low side.
E. patent CN102452946 reports a kind of reaction with trimethylamine aqueous solution and double (2-chloroethyl) ether and generates double season
Ammonium salt chloride, under nitrogen protection, adds triphenylphosphine, is warmed up to 140-160 DEG C of reaction 6-10h, obtains the double (2-bis-of product
Methylaminoethyl) ether and methyl triphenyl chlorination.The method major defect is: preparation method efficiency is low, and post processing is compared
Complexity, and phosphorus is unfriendly to environment.
F. patent CN102786427 reports three-step approach preparation method, and the first step is sub-with dichloro by 2-dimethylethanolamine
Sulfone reaction generates chloride, and 2-dimethylethanolamine and metallic sodium are reacted and generate sodium alkoxide by second step, and the 3rd step is for quaternary ammonium salt
Under the effect of class catalyst, chloride and sodium alkoxide generation etherification reaction, then carry out rectification under vacuum to product.The method mainly lacks
Point is: chloride post processing is complicated, and by-product is many, pollutes big.
These use double (2-dimethylaminoethyl) ether of 2-dimethylethanolamine or derivatives thereof generation etherification reaction preparation,
All there is more shortcoming and defect, such as: in course of reaction, chloride, sulfide etc. add the difficulty of post processing, the most right
Environment has a great impact.Additionally, 2-dimethylethanolamine or derivatives thereof often has in course of reaction, and sending out of side reaction occurs
Raw, thus cause productivity to reduce, it is the subject matter of method therefor so far.
Based on this, make the application.
Summary of the invention
For solving defect and deficiency present in existing preparation method, spy devise one diverse with existing route
Preparation synthetic route.The route of present invention design is double (2-dimethylaminoethyl) ether of two-step method synthesis, its method particularly includes:
The synthesis of the first step: 2-(2-(dimethylamino) ethyoxyl) ethanol；
Second step: 2-(2-(dimethylamino) ethyoxyl) ethanol and dimethylamine synthesize double (2-under the effect of catalyst
Dimethylaminoethyl) ether.
Wherein the first step can be refined as: a. feeds, b. synthetic reaction, c. post processing；Second step is subdivided into: a. feeds,
B. synthetic reaction, c. takes off amine/hydrogen, d. rectification.
Its reaction equation is as follows:
The first step:
Second step:
The double concrete synthetically prepared step of (2-dimethylaminoethyl) ether of two-step method synthesis is as follows:
The first step, the synthesis of 2-(2-(dimethylamino) ethyoxyl) ethanol:
A. dimethylamine and reacting ethylene oxide dimethylamine and reacting ethylene oxide under conditions of being not added with catalyst, its reaction
Molar ratio is that 1:2-2.5 (considers that from principle ratio should be 1:2, but can remain a certain amount of epoxy second in view of in pipeline
Alkane, so oxirane can somewhat excess in practice), with the air in nitrogen replacement reaction kettle before reaction, replace 3 times, instead
Answering temperature to be 60-100 DEG C, reaction 2-5h, ripening 0.5-1h are (after curing temperature general foundation reaction ripening, when anti-in 5min
The when of answering still pressure almost unchanged, it is considered that reaction terminates, and determines the curing time, generally 30-40min), after reaction
Obtain 2-(2-(dimethylamino) ethyoxyl) ethanol product.
B.2-(2-(dimethylamino) ethyoxyl) ethanol post processing is carried out, 100-120 DEG C of temperature in autoclave
Deaerate under degree 0.5-2h (a small amount of water and the oxirane of traces of unreacted in product is mainly removed in degassing), cooling
To 30-60 DEG C of discharging.
Second step, 2-(2-(dimethylamino) ethyoxyl) ethanol and dimethylamine synthesize double (2-under the effect of catalyst
Dimethylaminoethyl) ether:
A. charging: by catalyst Cu-Ni/ γ-Al2O3Load in autoclave, and by dimethylamine, 2-(2-(dimethyl
Amino) ethyoxyl) ethanol pours in reactor.
B. synthetic reaction: be passed through in reactor by hydrogen, is adjusted to 1.5～2.5MPa with hydrogen by pressure, and temperature controls
190～220 DEG C, reaction pressure controls at 10-25MPa, and the response time is 6-13h, obtains containing double (2-diformazans to reaction end
Base aminoethyl) mixture of ether.
C. amine/hydrogen is taken off: will be down to by pressure by air relief valve containing the mixture of double (2-dimethylaminoethyl) ethers
0.8-1.5MPa, leads to mixture in the middle part of de-amine/hydrogen tower, and column bottom temperature controls the diformazan at 130-160 DEG C, in mixture
Amine and hydrogen are discharged from de-amine/hydrogen top of tower, be dried gas, then will in having been preheated with the drying tower of 70-90 DEG C
Dimethylamine is passed through condenser and is separated by two kinds of gases with hydrogen mixed gas, and it is stand-by that lower floor's dimethylamine liquid enters recycling can, upper strata
Hydrogen suction hydrogen recycling can is stand-by.De-amine/hydrogen tower bottom is remaining is exactly double (2-dimethylaminoethyl) thick products of ether.
D. rectification: double (2-dimethylaminoethyl) the thick products of ether after processing load rectifying column and carry out the separated that reduces pressure
Go out double (2-dimethylaminoethyl) ether product.
Meanwhile, the present invention synthesizes 2-(2-(dimethylamino) ethyoxyl) ethanol and double (2-dimethylaminoethyl) ethers
Autoclave can be carried out in same reactor, in order to has saved the cost of equipment.
When carrying out in same reactor, its preparation process is: first synthesize 2-(2-(dimethyl in autoclave
Amino) ethyoxyl) ethanol, through the 100-120 DEG C of 0.5-2h that deaerates, it is cooled to 30-60 DEG C, it is as the double (2-of next step synthesis
Dimethylaminoethyl) raw material of ether, following step is according to the charging in second step, synthetic reaction, de-amine/hydrogen, rectification
Four steps complete the preparation of double (2-dimethylaminoethyl) ether.
The method have the advantages that
(1) double (2-dimethylaminoethyl) ether of two-step method synthesis relatively other preparation methoies, do not have chlorination in course of reaction
Thing, the introducing of sulfide, greatly reduce the difficulty of post processing, reduces the impact on environment.
(2) in the method preparing 2-(2-(dimethylamino) ethyoxyl) ethanol, need not the addition of catalyst, and produce
Product post processing can complete in a kettle., simple to operate.
(3) the recycling of hydrogen in whole course of reaction, and the recycling of dimethylamine, improves the profit of raw material
With rate and the conversion ratio of product.
(4) synthesis 2-(2-(dimethylamino) ethyoxyl) ethanol and double (2-dimethylaminoethyl) ethers can be same
Reactor carries out the reaction of correspondence, has saved the cost of equipment.
Accompanying drawing explanation
Fig. 1 is the synthesis flow schematic diagram of 2-in the application (2-(dimethylamino) ethyoxyl) ethanol；
Fig. 2 is the synthesis flow schematic diagram of double (2-dimethylaminoethyl) ethers in the application.
Detailed description of the invention
Embodiment 1: two-step reaction is in differential responses still
The first step, the synthesis of 2-(2-(dimethylamino) ethyoxyl) ethanol:
A. dimethylamine and reacting ethylene oxide dimethylamine and reacting ethylene oxide under conditions of being not added with catalyst, its reaction
Molar ratio is 1:2.1, with the air in nitrogen replacement reaction kettle before reaction, replaces 3 times, and reaction temperature is 90 DEG C, reacts 3h,
Ripening 0.5h, obtains 2-(2-(dimethylamino) ethyoxyl) ethanol product after reaction.
B.2-(2-(dimethylamino) ethyoxyl) ethanol post processing is carried out, in autoclave at a temperature of 100 DEG C
Degassing 1h, is cooled to 60 DEG C of dischargings.
Second step, the preparation of double (2-dimethylaminoethyl) ether:
A. charging: by catalyst Cu-Ni/ γ-Al2O3Load in autoclave, and by dimethylamine, 2-(2-(dimethyl
Amino) ethyoxyl) ethanol pours in reactor.
B. synthetic reaction: be passed through in reactor by hydrogen, is adjusted to 2MPa with hydrogen by pressure, and temperature controls at 210 DEG C, instead
Answering pressure to be about 16MPa, the response time is 9h, obtains the mixture containing double (2-dimethylaminoethyl) ethers to reaction end.
C. amine/hydrogen is taken off: will be down to by pressure by air relief valve containing the mixture of double (2-dimethylaminoethyl) ethers
1.0MPa, leads in the middle part of de-amine/hydrogen tower by mixture, and column bottom temperature controls at 145 DEG C, the dimethylamine in mixture and hydrogen
Discharge from de-amine/hydrogen top of tower, in having been preheated with the drying tower of 80 DEG C, be dried gas, then by dimethylamine and hydrogen
Gaseous mixture is passed through condenser and is separated by two kinds of gases, and it is stand-by that lower floor's dimethylamine liquid enters recycling can, upper strata hydrogen suction hydrogen
Recycling can is stand-by.De-amine/hydrogen tower bottom is remaining is exactly double (2-dimethylaminoethyl) thick products of ether.
D. rectification: carry out decompression distillation point in double (2-dimethylaminoethyl) the ether thick products loading rectifying columns after processing
Separate out double (2-dimethylaminoethyl) ether product.
Product is light yellow transparent liquid, and product purity is 99.65%, and yield is 74.51%.
Embodiment 2: two-step reaction is carried out in same reactor
Synthesis 2-(2-(dimethylamino) ethyoxyl) ethanol and double (2-dimethylaminoethyl) ethers can same instead
Answering still to carry out the reaction of correspondence, its method is as follows:
When carrying out in same reactor, preparation method and condition are same as in Example 1, the first step, in reaction under high pressure
Still synthesizes 2-(2-(dimethylamino) ethyoxyl) ethanol, through 110 DEG C of 1h that deaerate, is cooled to when 30 DEG C close as next step
The raw material of Cheng Shuan (2-dimethylaminoethyl) ether.
Ensuing second step, is carried out fully according to the second step in embodiment 1.
Product is light yellow transparent liquid, and purity is 99.58%, and yield is 74.46%.Different height is used from embodiment 1
The product that pressure reactor prepares is compared, and quality and yield are almost without difference, and have saved the cost of equipment.
Embodiment 3-12
The preparation method of embodiment 3-12 is same as in Example 1, is different from part 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.
The reaction temperature impact on product in table 1 first step
From table 1 it can be observed how: the first step, product yield, response time are had a certain impact by reaction temperature, with
The rising of reaction temperature in the first step, the response time in the first step shortens therewith, product yield increases；But when reaction
When temperature is 100 DEG C, product colour is light yellow, and yield also begins to reduce, and this is likely due to reaction temperature rising and causes pair
Reaction causes, and therefore may determine that and show that reacting optimum temperature in the first step is 90 DEG C, and temperature-controllable scope is 80-90
℃。
The reaction temperature impact on product in table 2 second step
From table 2 it can be observed how: second step, product yield, reaction pressure and response time are all had significantly by reaction temperature
Impact, along with the rising of the reaction temperature in second step, the reaction pressure in second step increases, the response time contracts therewith
Short, product yield increases；But when temperature is 220 DEG C, pressure is 19MPa, and product yield, relatively reaction temperature are 210 DEG C
Product yield only increase by 0.08%, pressure but exceeds 3MPa, therefore, it is determined that the reaction temperature optimum drawn in second step is
220℃。
H in table 3 second step2The initial pressure impact on product
From table 3 it can be observed how: H second step2Initial action pressure is equal to product yield, reaction pressure and response time
Have a significant impact, along with H in second step2The rising of initial action pressure, the reaction pressure of second step increases, the response time
Shorten therewith, product yield increases；But it can also be seen that work as H from table 32Initial action pressure be 2.0MPa and
During 2.5MPa, the yield difference of product is the least, but pressure raise obvious especially, wherein H2Initial action pressure is
During 2.5MPa, reaction pressure is up to 21MPa, on the premise of little on product yield impact, for the sake of production safety, the
H in two steps2Initial action pressure optimum is 2.0MPa.
Double (2-dimethylaminoethyl) ether of two-step method synthesis provided herein is compared with other preparation methoies, in reaction
During there is no the introducing of chloride, sulfide, greatly reduce the difficulty of post processing, reduce the impact on environment；Meanwhile, exist
Prepare the addition that need not catalyst in the method for 2-(2-(dimethylamino) ethyoxyl) ethanol, and product post processing is in reaction
Still can complete, simple to operate；And in whole course of reaction the recycling of hydrogen, and the recycling of dimethylamine,
Improve the utilization rate of raw material and the conversion ratio of product；Synthesis 2-(2-(dimethylamino) ethyoxyl) ethanol and double (2-diformazan
Base aminoethyl) can the carrying out in two reactors of ether, it is possible to carry out the reaction of correspondence at same reactor, save equipment
Cost, efficiently solve in existing method and technique the problems such as three-protection design difficulty, product yield are low, of poor quality.
Above content be the preferred implementation combining the invention provided technical scheme is made further in detail
Describe in detail bright, it is impossible to assert that the invention is embodied as being confined to these explanations above-mentioned, for technology belonging to the invention
For the those of ordinary skill in field, without departing from the concept of the premise of the invention, it is also possible to make some simple deductions
Or replace, all should be considered as belonging to the protection domain of the invention.
Claims (7)
1. the synthetic method of double (2-dimethylaminoethyl) ethers, it is characterised in that: it is made up of following two steps:
(1) synthesis of 2-(2-(dimethylamino) ethyoxyl) ethanol: dimethylamine and reacting ethylene oxide obtain 2-(2-(diformazan
Base amino) ethyoxyl) ethanol product；
(2) double (2-dimethylaminoethyl) ethers synthesis:
A. charging: by catalyst Cu-Ni/ γ-Al2O3Load in autoclave, and by synthesized by dimethylamine and step (1)
2-(2-(dimethylamino) ethyoxyl) ethanol pours in reactor；
B. synthetic reaction: with hydrogen, reacting kettle inner pressure being adjusted to 1.5～2.5MPa, temperature controls at 190～220 DEG C, controls
Reaction pressure reacts 6-13h at 10-25MPa, obtains the mixture containing double (2-dimethylaminoethyl) ethers to reaction end；
C. amine/hydrogen is taken off: after the mixture pressure containing double (2-dimethylaminoethyl) ethers is down to 0.8-1.5MPa, lead to de-
In the middle part of amine/hydrogen tower, dimethylamine and hydrogen in mixture are discharged from de-amine/hydrogen top of tower, and de-amine/hydrogen tower bottom is left
Be exactly double (2-dimethylaminoethyl) thick products of ether；
D. rectification: double (2-dimethylaminoethyl) the thick products of ether after step c being processed load rectifying column and carry out decompression distillation point
Separate out double (2-dimethylaminoethyl) ether product.
2. the synthetic method of a kind of double (2-dimethylaminoethyl) ethers as claimed in claim 1, it is characterised in that step (1)
In, the synthesis condition of 2-(2-(dimethylamino) ethyoxyl) ethanol product is: dimethylamine and reacting ethylene oxide molar ratio
For 1:2-2.5, reaction temperature is 60-100 DEG C, reacts 2-5h, ripening 0.5-1h.
3. the synthetic method of a kind of double (2-dimethylaminoethyl) ethers as claimed in claim 1, it is characterised in that: step (1)
In, synthesized 2-(2-(dimethylamino) ethyoxyl) ethanol deaerates after 0.5-2h at a temperature of 100-120 DEG C, is cooled to
30-60 DEG C, standby.
4. the synthetic method of a kind of double (2-dimethylaminoethyl) ethers as claimed in claim 1, it is characterised in that: described two
Methylamine and hydrogen after drying, are passed through condenser and are separated by two kinds of gases, and it is stand-by that lower floor's dimethylamine liquid enters recycling can, upper strata
Hydrogen suction hydrogen recycling can is stand-by.
5. the synthetic method of a kind of double (2-dimethylaminoethyl) ethers as claimed in claim 4, it is characterised in that: described is dry
Dry temperature is 70-90 DEG C.
6. the synthetic method of a kind of double (2-dimethylaminoethyl) ethers as claimed in claim 1, it is characterised in that: in step c,
Column bottom temperature controls at 130-160 DEG C, makes double (2-dimethylaminoethyl) thick product of ether and dimethylamine and Hydrogen Separation.
7. the synthetic method of a kind of double (2-dimethylaminoethyl) ethers as described in any one of claim 1-6, it is characterised in that
Described step (1) is carried out with still with step (2), and synthesis technique is: in autoclave, dimethylamine and reacting ethylene oxide
Molar ratio is 1:2-2.2, and reaction temperature is 60-100 DEG C, reacts 2-5h, ripening 0.5-1h；Interpolation catalyst Cu-Ni/ γ-
Al2O3, with hydrogen, pressure in still being adjusted to 1.5～2.5MPa, temperature controls at 190～220 DEG C, controls reaction pressure at 10-
25MPa reacts 6-13h；After pressure is down to 1.0MPa, lead in the middle part of de-amine/hydrogen tower, dimethylamine in mixture and hydrogen from
De-amine/hydrogen top of tower is discharged, and double (2-dimethylaminoethyl) ether thick product decompression separated of de-amine/hydrogen tower bottom are i.e.
Can.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511153A (en) * | 2019-04-15 | 2019-11-29 | 绍兴兴欣新材料股份有限公司 | A kind of preparation method of bis- (2- dimethyl amido ethyl) ethers |
| 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 |
Citations (14)
| 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 |
| GB1585480A (en) * | 1976-05-14 | 1981-03-04 | Basf Ag | Production of tertiary amines |
| EP0167872A2 (en) * | 1984-06-19 | 1986-01-15 | BASF Aktiengesellschaft | Process for the production of amines |
| US4922023A (en) * | 1987-07-22 | 1990-05-01 | Basf Aktiengesellschaft | Preparation of aliphatic N,N-dialkyl-substituted amino alcohols |
| US6187957B1 (en) * | 1998-12-23 | 2001-02-13 | Basf Aktiengesellschaft | Preparation of amines |
| 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 |
| US7169268B2 (en) * | 2002-06-26 | 2007-01-30 | Huntsman Petrochemical Corporation | Color stabilization of amines |
| CN1984873A (en) * | 2004-05-13 | 2007-06-20 | 巴斯福股份公司 | Method for the continuous production of an amine |
| 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 |
| US20120157715A1 (en) * | 2010-12-17 | 2012-06-21 | Basf Se | Process for preparing an n,n-dialky-ethanolamine having high color stability |
| 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 |
-
2016
- 2016-08-19 CN CN201610697504.2A patent/CN106316868B/en active Active
Patent Citations (14)
| 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 |
| GB1585480A (en) * | 1976-05-14 | 1981-03-04 | Basf Ag | Production of tertiary amines |
| EP0167872A2 (en) * | 1984-06-19 | 1986-01-15 | BASF Aktiengesellschaft | Process for the production of amines |
| US4922023A (en) * | 1987-07-22 | 1990-05-01 | Basf Aktiengesellschaft | Preparation of 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 |
| US6187957B1 (en) * | 1998-12-23 | 2001-02-13 | Basf Aktiengesellschaft | Preparation of amines |
| US7169268B2 (en) * | 2002-06-26 | 2007-01-30 | Huntsman Petrochemical Corporation | Color stabilization of amines |
| CN1984873A (en) * | 2004-05-13 | 2007-06-20 | 巴斯福股份公司 | Method for the continuous production of an amine |
| 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 |
| US20120157715A1 (en) * | 2010-12-17 | 2012-06-21 | Basf Se | Process for preparing an n,n-dialky-ethanolamine having high color stability |
| 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 (2)
| Title |
|---|
| NATALIA ANDRUSHKO等: "Amination of Aliphatic Alcohols and Diols with an Iridium Pincer Catalyst", 《CHEMCATCHEM》 * |
| 王婧祎: "一缩乙二醇法合成BDMAEE和DMAEE", 《聚氨酯工业》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110511153A (en) * | 2019-04-15 | 2019-11-29 | 绍兴兴欣新材料股份有限公司 | A kind of preparation method of bis- (2- dimethyl amido ethyl) ethers |
| CN110511153B (en) * | 2019-04-15 | 2022-05-06 | 绍兴兴欣新材料股份有限公司 | Preparation method of bis (2-dimethylaminoethyl) ether |
| 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 |
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| Publication number | Publication date |
|---|---|
| CN106316868B (en) | 2019-01-29 |
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