CN104860886A - Method for preparing 1-(2-ethoxyl)-2-imidazolone by using CO2 as raw material - Google Patents
Method for preparing 1-(2-ethoxyl)-2-imidazolone by using CO2 as raw material Download PDFInfo
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- CN104860886A CN104860886A CN201510274783.7A CN201510274783A CN104860886A CN 104860886 A CN104860886 A CN 104860886A CN 201510274783 A CN201510274783 A CN 201510274783A CN 104860886 A CN104860886 A CN 104860886A
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- imidazolone
- hydroxyethyl
- raw material
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- prepared
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- 239000002994 raw material Substances 0.000 title claims abstract description 30
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- 239000000047 product Substances 0.000 claims abstract description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- VGRRSFLZALJQNT-UHFFFAOYSA-N 3-(2-hydroxyethyl)-1h-imidazol-2-one Chemical compound OCCN1C=CNC1=O VGRRSFLZALJQNT-UHFFFAOYSA-N 0.000 claims description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 23
- KGWDUNBJIMUFAP-KVVVOXFISA-N Ethanolamine Oleate Chemical compound NCCO.CCCCCCCC\C=C/CCCCCCCC(O)=O KGWDUNBJIMUFAP-KVVVOXFISA-N 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 9
- 238000010907 mechanical stirring Methods 0.000 claims description 8
- 239000006227 byproduct Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- BXOAIZOIDUQOFA-UHFFFAOYSA-M 1-butyl-3-methylimidazol-3-ium;hydroxide Chemical compound [OH-].CCCC[N+]=1C=CN(C)C=1 BXOAIZOIDUQOFA-UHFFFAOYSA-M 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 abstract 2
- ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical class OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000012822 chemical development Methods 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- 235000011089 carbon dioxide Nutrition 0.000 description 4
- -1 carbamide compound Chemical class 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- FTJDCTJLENOGMA-UHFFFAOYSA-N 4-(2-hydroxyethyl)imidazol-2-one Chemical compound OCCC1=NC(=O)N=C1 FTJDCTJLENOGMA-UHFFFAOYSA-N 0.000 description 2
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000003156 secondary amide group Chemical group 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention relates to the field of preparation of cyclic urea compounds, particularly to a method for preparing 1-(2-ethoxyl)-2-imidazolone by using CO2 as a raw material. 1-(2-ethoxyl)-2-imidazolone is obtained through a reaction of CO2 and ethanolamine. Compared with a conventional technology for preparing 1-(2-ethoxyl)-2-imidazolone, the method disclosed by the invention has the following advantages: (1) a synthetic method is scientific to design, an execution route is concise and reliable, and the method is suitable for industrial production; (2) required raw materials are low in toxicity, are cheap and are easy to obtain, so that the method conforms to the trend of green chemical development; (3) a catalyst is used in the reaction process, the catalytic activity is high, and the product yield is higher; (4) from the view of resources, the CO2 is a safe non-toxic rich carbon resource, and a reaction product, namely water, does not cause pressure to the environment.
Description
Technical field
The present invention relates to ring carbamide compound preparation field, specifically a kind of with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material.
Background technology
A large amount of discharges of carbonic acid gas bring serious environmental problem and Climatic issues, but carbonic acid gas is also simultaneously the carbon source of a kind of rich reserves, cheapness, nontoxic, reusable edible, is the very potential raw material of organic chemical industry.Utilize carbonic acid gas to carry out concentration that organic synthesis can not only reduce carbonic acid gas in air, but also can be valuable organic chemicals by carbon dioxide fixation.The present invention utilizes amine substance stabilizing carbon dioxide, and successfully synthesizes a kind of ring carbamide compound 1-(2-hydroxyethyl)-2-imidazolone.
No. CAS of 1-(2-hydroxyethyl)-2-imidazolone is 3699-54-5, and structural formula is as follows:
1-(2-hydroxyethyl)-2-imidazolone, as a kind of ring carbamide compound, is widely used in the field such as molecular biology, pharmacology.At present, the route of synthesis of 1-(2-hydroxyethyl)-2-imidazolone is mainly: with urea and 1-(2-hydroxyethyl) quadrol for raw material, high temperature cyclization synthesis 1-(2-hydroxyethyl)-2-imidazolone.But quadrol price is more expensive for the raw material 1-that the method is used (2-hydroxyethyl), and temperature of reaction is too high, because which limit the scale of reaction.
Given this, need a kind of method with low cost, simple and easy to get badly and prepare 1-(2-hydroxyethyl)-2-imidazolone.
Summary of the invention
In order to overcome, reaction raw materials cost in prior art is high, the defect of severe reaction conditions, the object of the present invention is to provide a kind of green, efficient, succinct with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material.
The present invention is achieved by the following technical solutions: with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, 1-(2-hydroxyethyl)-2-imidazolone is by CO
2with thanomin reaction obtain.
In order to be explained in detail the present invention, provide the step of described method:
(1) in autoclave, add the catalyzer of thanomin, solvent and basic cpd successively;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 130 ~ 200 DEG C, regulate CO in autoclave
2pressure to 2 ~ 8MPa, reacts under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out.
The synthetic route of 1-of the present invention (2-hydroxyethyl)-2-imidazolone is:
Solvent in the method for the invention step adopts the solvent of solubilized thanomin, preferred alcohol.During concrete use, the add-on of etoh solvent is be 1:1 with the volume ratio of thanomin.
In addition, the catalyzer that the invention provides described basic cpd is K
3pO
4, Na
3pO
4, Li
3pO
4, K
2cO
3, Na
2cO
3, KOH, NaOH, one in [BMIm] OH.Adopt the catalyzer of above-mentioned any basic cpd during embody rule, its Yield of final product is all more than 15%; But the employing K optimized
3pO
4, the productive rate of end product is more than 60%.
During concrete use, the mol ratio of the catalyzer of thanomin and basic cpd is 1:0.01, and by the research to reaction process, under this mol ratio, reaction raw materials transformation efficiency is high, and namely the productive rate of end product is high.Ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:4 ~ 6, adopt other eluting solvents of this area also can reach the object of product separation in theory, but adopt eluting solvent of the present invention, the separation and purification time is short, and product purity is very high.
In reactions steps of the present invention, the length in mechanical stirring lower reaction times does not affect the acquisition of reacting final product (1-(2-hydroxyethyl)-2-imidazolone), namely the reaction times is too short, reaction raw materials low conversion rate, products collection efficiency are low, and the reaction times is long, reaction raw materials has transformed, length consuming time.Therefore, the reaction times of the employing 6 ~ 10h of optimization, the temperature of reaction of the employing 170 ~ 190 DEG C of the present invention's optimization in addition, the CO of 6 ~ 8MPa
2pressure.
The present invention, compared with the existing technique preparing 1-(2-hydroxyethyl)-2-imidazolone, has superiority as described below:
(1) synthetic method design science, execution path is succinctly reliable, is applicable to industrial production.
(2) desired raw material toxicity is low, is cheaply easy to get, and meets green chemistry trend.
(3) adopt catalyst activity high in reaction process, product yield is higher.
(4) from resource view, CO
2be a kind of safe, nontoxic, abundant carbon resource, and reaction product water also can not to environment build-up of pressure.
Experiment: the preparation method utilizing 1-provided by the invention (2-hydroxyethyl)-2-imidazolone, each parameter is respectively 0.3mol thanomin, 20mL ethanol, 3mmol catalyzer, 170 DEG C of temperature, 6MPa CO
2, mechanic whirl-nett reaction time 6h, be ethanol and the dichloromethane mixture chromatographic column eluting solvent wash-out of 1:6 through volume ratio, obtain end product 1-(2-hydroxyethyl)-2-imidazolone, concrete outcome is as shown in table 1:
The each catalyst formulation of table 1 prepares the Comparative result of 1-(2-hydroxyethyl)-2-imidazolone
Accompanying drawing explanation
Fig. 1 is the infrared spectrogram of 1-(2-the hydroxyethyl)-2-imidazolone that embodiment 1 obtains, 1660cm in figure
-1place is C=O stretching vibration absorption peak, 1496cm
-1place is secondary amide N-H flexural vibration absorption peak, shows thanomin and CO
2there occurs reaction.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of 1-(2-the hydroxyethyl)-2-imidazolone that embodiment 1 obtains, the peak that in figure, chemical shift δ=3.30,3.45ppm place occur is the absorption peak of methylene radical Hydrogen Proton on 1-(2-hydroxyethyl)-2-imidazolone five-ring, shows thanomin and CO
2there occurs reaction, and reaction generates 1-(2-hydroxyethyl)-2-imidazolone.
Fig. 3 is the carbon-13 nmr spectra figure of 1-(2-the hydroxyethyl)-2-imidazolone that embodiment 1 obtains, the peak that in figure, chemical shift δ=37.99,45.15ppm place occur can be attributed to the absorption peak of mesomethylene carbon on 1-(2-hydroxyethyl)-2-imidazolone five-ring, the peak that chemical shift δ=165.02ppm occurs is the absorption peak of 1-(2-hydroxyethyl)-2-imidazolone carbonyl carbon, shows thanomin and CO
2there occurs reaction, and reaction generates 1-(2-hydroxyethyl)-2-imidazolone.
Embodiment
Embodiment 1
With CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, the steps include:
(1) in autoclave, 0.3mol thanomin, 20mL ethanol and 3mmol K is added successively
3pO
4;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 190 DEG C, regulate CO in autoclave
2pressure, to 6MPa, reacts 6h under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out, ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:6.
The productive rate of above-mentioned 1-(2-hydroxyethyl)-2-imidazolone is 66.7%.
Embodiment 2
With CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, the steps include:
(1) in autoclave, 0.3mol thanomin, 20mL ethanol and 3mmol Na is added successively
3pO
4;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 170 DEG C, regulate CO in autoclave
2pressure, to 6MPa, reacts 10h under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out, ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:4.
The productive rate of above-mentioned 1-(2-hydroxyethyl)-2-imidazolone is 58.2%.
Embodiment 3
With CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, the steps include:
(1) in autoclave, 0.3mol thanomin, 20mL ethanol and 3mmol Li is added successively
3pO
4;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 170 DEG C, regulate CO in autoclave
2pressure, to 8MPa, reacts 6h under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out, ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:5.
The productive rate of above-mentioned 1-(2-hydroxyethyl)-2-imidazolone is 28.5%.
Embodiment 4
With CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, the steps include:
(1) in autoclave, 0.3mol thanomin, 20mL ethanol and 3mmol K is added successively
2cO
3;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 130 DEG C, regulate CO in autoclave
2pressure, to 2MPa, reacts 8h under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out, ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:6.
The productive rate of above-mentioned 1-(2-hydroxyethyl)-2-imidazolone is 19.7%.
Embodiment 5
With CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, the steps include:
(1) in autoclave, add 0.3mol thanomin, 20mL ethanol and 3mmol [BMIm] OH successively;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 200 DEG C, regulate CO in autoclave
2pressure, to 4MPa, reacts 6h under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out, ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:4.
The productive rate of above-mentioned 1-(2-hydroxyethyl)-2-imidazolone is 42.9%.
Claims (10)
1. with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, 1-(2-hydroxyethyl)-2-imidazolone is by CO
2with thanomin reaction obtain.
2. according to claim 1 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, the steps include:
(1) in autoclave, add the catalyzer of thanomin, solvent and basic cpd successively;
(2) CO is passed in advance
2, and temperature of reaction is progressively risen to 130 ~ 200 DEG C, regulate CO in autoclave
2pressure to 2 ~ 8MPa, reacts under mechanical stirring;
(3) after having reacted, autoclave is cooled to room temperature, takes out product, and utilize rotary distillation to remove solvent and water byproduct;
(4) end product 1-(2-hydroxyethyl)-2-imidazolone is obtained through chromatographic column wash-out.
3. according to claim 2 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, the catalyzer of described basic cpd is K
3pO
4, Na
3pO
4, Li
3pO
4, K
2cO
3, Na
2cO
3, KOH, NaOH, one in [BMIm] OH.
4. according to claim 3 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, the preferred K of catalyzer of described basic cpd
3pO
4.
5. according to claim 4 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, the mol ratio of the catalyzer of described thanomin and basic cpd is 1:0.01.
6. according to claim 5 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, described solvent preferred alcohol.
7. according to claim 1 to 6 arbitrarily claim with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, ethanol and the dichloromethane mixture of described chromatographic column eluting solvent to be volume ratio be 1:4 ~ 6.
8. according to claim 7 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, described temperature of reaction preferably 170 ~ 190 DEG C.
9. according to claim 7 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, described CO
2pressure is 6 ~ 8MPa preferably.
10. according to claim 7 with CO
2for the method for 1-(2-hydroxyethyl)-2-imidazolone prepared by raw material, it is characterized in that, preferably 6 ~ 10h of described reaction times.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510274783.7A CN104860886B (en) | 2015-05-26 | 2015-05-26 | With CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510274783.7A CN104860886B (en) | 2015-05-26 | 2015-05-26 | With CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material |
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| Publication Number | Publication Date |
|---|---|
| CN104860886A true CN104860886A (en) | 2015-08-26 |
| CN104860886B CN104860886B (en) | 2017-08-25 |
Family
ID=53907121
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510274783.7A Active CN104860886B (en) | 2015-05-26 | 2015-05-26 | With CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110997638A (en) * | 2017-08-11 | 2020-04-10 | 诺力昂化学品国际有限公司 | Process for preparing cyclic urea adducts of ethylene amine compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0496168A1 (en) * | 1991-01-25 | 1992-07-29 | BP Chemicals Limited | Process for the production of N-(2-hydroxyethyl)-2-imidazolidinone |
-
2015
- 2015-05-26 CN CN201510274783.7A patent/CN104860886B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0496168A1 (en) * | 1991-01-25 | 1992-07-29 | BP Chemicals Limited | Process for the production of N-(2-hydroxyethyl)-2-imidazolidinone |
Non-Patent Citations (4)
| Title |
|---|
| ANGELICA ION等: "Synthesis of symmetrical or asymmetrical urea compounds from CO2 via base catalysis", 《GREEN CHEMISTRY》 * |
| BHALCHANDRA M. BHANAGE等: "Synthesis of cyclic ureas and urethanes from alkylene diamines and amino alcohols with pressurized carbon dioxide in the absence of catalysts", 《GREEN CHEMISTRY》 * |
| SHIN-ICHIRO FUJITA等: "Preparation of cyclic urethanes from amino alcohols and carbon dioxide using ionic liquid catalysts with alkali metal promoters", 《INT. J. MOL. SCI.》 * |
| TAO JIANG等: "Solvent-free synthesis of substituted ureas from CO2 and amines with functional ionic liquid as the catalyst", 《GREEN CHEMISTRY》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110997638A (en) * | 2017-08-11 | 2020-04-10 | 诺力昂化学品国际有限公司 | Process for preparing cyclic urea adducts of ethylene amine compounds |
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Effective date of registration: 20231110 Address after: Room 6318, Block B, Building 182, No. 3 Xueyuan Road, Jiancaoping District, Taiyuan City, Shanxi Province 030051 Patentee after: Shanxi Zhongbei New Materials Technology Co.,Ltd. Address before: 030051, Xueyuan Road, Shanxi Province, Taiyuan Province, No. 3 Patentee before: NORTH University OF CHINA |
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