CN104860886B - With CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material - Google Patents
With CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material Download PDFInfo
- Publication number
- CN104860886B CN104860886B CN201510274783.7A CN201510274783A CN104860886B CN 104860886 B CN104860886 B CN 104860886B CN 201510274783 A CN201510274783 A CN 201510274783A CN 104860886 B CN104860886 B CN 104860886B
- Authority
- CN
- China
- Prior art keywords
- imidazolones
- ethoxys
- product
- autoclave
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 239000002994 raw material Substances 0.000 title claims abstract description 19
- ADTASGCQQGXYFS-UHFFFAOYSA-N C(C)OC1=NC(N=C1)=O Chemical class C(C)OC1=NC(N=C1)=O ADTASGCQQGXYFS-UHFFFAOYSA-N 0.000 title abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 239000000047 product Substances 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 9
- 239000006227 byproduct Substances 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000013019 agitation Methods 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract description 6
- 239000004202 carbamide Substances 0.000 abstract description 5
- 235000013877 carbamide Nutrition 0.000 abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 4
- -1 carbamide compound Chemical class 0.000 abstract description 4
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 231100000252 nontoxic Toxicity 0.000 abstract description 3
- 230000003000 nontoxic effect Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000010189 synthetic method Methods 0.000 abstract description 2
- 230000001988 toxicity Effects 0.000 abstract description 2
- 231100000419 toxicity Toxicity 0.000 abstract description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 21
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 13
- 239000001569 carbon dioxide Substances 0.000 description 6
- 150000002169 ethanolamines Chemical class 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000010907 mechanical stirring Methods 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 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 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000005457 optimization Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 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
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000005516 engineering process Methods 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
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910001386 lithium phosphate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003334 secondary amides Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- TWQULNDIKKJZPH-UHFFFAOYSA-K trilithium;phosphate Chemical compound [Li+].[Li+].[Li+].[O-]P([O-])([O-])=O TWQULNDIKKJZPH-UHFFFAOYSA-K 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 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 present invention relates to the preparation field of ring carbamide compound, specifically one kind is with CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material, 1 (2 ethoxy) 2 imidazolones are by CO2React what is obtained with monoethanolamine.It is of the invention with it is existing preparation 1 (2 ethoxy) 2 imidazolones technique compared with, with superiority as described below：（1）Synthetic method design science, execution route is succinctly reliable, is adapted to industrial production.（2）Required material toxicity is low, cheap and easily-available, meets green chemistry trend.（3）High using catalyst activity in course of reaction, product yield is higher.（4）From the point of view of resource view, CO2It is a kind of safe and nontoxic, abundant carbon resource, and reaction product water also will not be to environment build-up of pressure.
Description
Technical field
The present invention relates to ring carbamide compound preparation field, specifically one kind is with CO21- (2- ethoxys) -2- is prepared for raw material
The method of imidazolone.
Background technology
A large amount of discharges of carbon dioxide bring serious environmental problem and climatic issues, but carbon dioxide is also a kind of simultaneously
Rich reserves, cheap, nontoxic, reusable edible carbon source, are the very promising raw materials of organic chemical industry.Carried out using carbon dioxide
Organic synthesis can not only reduce the concentration of carbon dioxide in air, but also can have carbon dioxide fixation to be valuable
Chemical machine product.The present invention fixes carbon dioxide using amine substance, and successfully synthesizes a kind of ring carbamide compound 1- (2- hydroxyl second
Base) -2- imidazolones.
No. CAS of 1- (2- ethoxys) -2- imidazolones is 3699-54-5, and structural formula is as follows：
1- (2- ethoxys) -2- imidazolones are widely used in molecular biology, pharmacology as a kind of ring carbamide compound
Deng field.At present, the route of synthesis of 1- (2- ethoxys) -2- imidazolones is mainly：With urea and 1- (2- ethoxys) second two
Amine is raw material, high temperature cyclization synthesis 1- (2- ethoxys) -2- imidazolones.But raw material 1- (2- ethoxys) second used in this method
Diamines is expensive, and reaction temperature is too high, therefore limits the scale of reaction.
In consideration of it, needing a kind of method with low cost, simple and easy to get badly prepares 1- (2- ethoxys) -2- imidazolines
Ketone.
The content of the invention
In order to overcome, reaction raw materials cost in the prior art is high, severe reaction conditions defects, it is an object of the invention to
There is provided a kind of green, efficiently, it is succinct with CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material.
The present invention is achieved by the following technical solutions：With CO21- (2- ethoxys) -2- imidazolones are prepared for raw material
Method, 1- (2- ethoxys) -2- imidazolones are by CO2React what is obtained with monoethanolamine.
In order to which the present invention is explained in detail, there is provided the step of methods described：
(1) catalyst of monoethanolamine, solvent and alkali compounds is sequentially added into autoclave；
(2) CO is passed through in advance2, and reaction temperature is progressively risen to CO in 130~200 DEG C, regulation autoclave2Pressure is to 2
Reacted under~8MPa, mechanical agitation；
(3) autoclave is cooled to room temperature after the completion of reacting, product is taken out, and using rotary distillation remove solvent and
Water byproduct；
(4) end-product 1- (2- ethoxys) -2- imidazolones are afforded by chromatographic column.
The synthetic route of 1- (2- ethoxys) -2- imidazolones of the present invention is：
Solvent in the method for the invention step is using the solvent that can dissolve monoethanolamine, preferred alcohol.Specifically make
Used time, it with the volume ratio of monoethanolamine is 1 that the addition of etoh solvent, which is,:1.
In addition, being K the invention provides the catalyst of the alkali compounds3PO4、Na3PO4、Li3PO4、K2CO3、
Na2CO3, KOH, NaOH, one kind in [BMIm] OH.Using the catalyst of above-mentioned any alkali compounds during concrete application,
Its Yield of final product is more than 15%；But the use K of optimization3PO4, the yield of end-product is more than 60%.
When specifically used, the mol ratio of the catalyst of monoethanolamine and alkali compounds is 1:0.01, by reaction process
Research, the yield of reaction raw materials high conversion rate, i.e. end-product is high under this mol ratio.The chromatographic column eluting solvent is volume
Than for 1:4~6 ethanol and dichloromethane mixture, can also reach product point using other eluting solvents of this area in theory
From purpose, but use eluting solvent of the present invention, it is short to isolate and purify the time, and product purity is very high.
The length in mechanical agitation lower reaction time has no effect on reacting final product (1- (2- hydroxyl second in reactions steps of the present invention
Base) -2- imidazolones) acquisition, i.e., the reaction time is too short, reaction raw materials conversion ratio is low, products collection efficiency is low, reaction time mistake
Long, reaction raw materials convert completion, time-consuming.Therefore, 6~10h of use of optimization reaction time, what the present invention optimized in addition adopts
With 170~190 DEG C of reaction temperature, 6~8MPa CO2Pressure.
It is of the invention compared with the existing technique for preparing 1- (2- ethoxys) -2- imidazolones, with as described below superior
Property：
(1) synthetic method design science, execution route is succinctly reliable, is adapted to industrial production.
(2) material toxicity is low needed for, cheap and easily-available, meets green chemistry trend.
(3) high using catalyst activity in course of reaction, product yield is higher.
(4) from the point of view of resource view, CO2It is a kind of safe and nontoxic, abundant carbon resource, and reaction product water is not yet
Can be to environment build-up of pressure.
Experiment：Using the preparation method of 1- (2- ethoxys) -2- imidazolones of the invention provided, each parameter is respectively
0.3mol monoethanolamines, 20mL ethanol, 3mmol catalyst, 170 DEG C of temperature, 6MPa CO2, mechanic whirl-nett reaction time 6h, process
Volume ratio is 1：6 ethanol and dichloromethane mixture chromatographic column eluting solvent elution, obtains end-product 1- (2- ethoxys) -2-
Imidazolone, concrete outcome is as shown in table 1：
Each catalyst formulation of table 1 prepares the Comparative result of 1- (2- ethoxys) -2- imidazolones
Brief description of the drawings
Fig. 1 is 1660cm in the infrared spectrogram of 1- (2- ethoxys) -2- imidazolones that embodiment 1 is obtained, figure-1Locate be
C=O stretching vibration absworption peaks, 1496cm-1Locate for secondary amide N-H flexural vibrations absworption peaks, to show monoethanolamine and CO2It there occurs anti-
Should.
Fig. 2 is chemical potential in the hydrogen nuclear magnetic resonance spectrogram of 1- (2- ethoxys) -2- imidazolones that embodiment 1 is obtained, figure
The peak occurred at shifting δ=3.30,3.45ppm is the suction of methylene Hydrogen Proton on 1- (2- ethoxys) -2- imidazolone five-membered rings
Peak is received, shows monoethanolamine and CO2Reacted, and reaction generates 1- (2- ethoxys) -2- imidazolones.
Fig. 3 is chemical potential in the carbon-13 nmr spectra figure of 1- (2- ethoxys) -2- imidazolones that embodiment 1 is obtained, figure
The peak occurred at shifting δ=37.99,45.15ppm can be attributed to mesomethylene carbon on 1- (2- ethoxys) -2- imidazolone five-membered rings
Absworption peak, the peak that chemical shift δ=165.02ppm occurs is the absworption peak of 1- (2- ethoxys) -2- imidazolone carbonyl carbons,
Show monoethanolamine and CO2Reacted, and reaction generates 1- (2- ethoxys) -2- imidazolones.
Embodiment
Embodiment 1
With CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material, its step is：
(1) 0.3mol monoethanolamines, 20mL ethanol and 3mmol K are sequentially added into autoclave3PO4；
(2) CO is passed through in advance2, and reaction temperature is progressively risen to CO in 190 DEG C, regulation autoclave2Pressure to 6MPa,
6h is reacted under mechanical stirring；
(3) autoclave is cooled to room temperature after the completion of reacting, product is taken out, and using rotary distillation remove solvent and
Water byproduct；
(4) end-product 1- (2- ethoxys) -2- imidazolones, the chromatographic column eluting solvent are afforded by chromatographic column
It is 1 for volume ratio：6 ethanol and dichloromethane mixture.
The yield of above-mentioned 1- (2- ethoxys) -2- imidazolones is 66.7%.
Embodiment 2
With CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material, its step is：
(1) 0.3mol monoethanolamines, 20mL ethanol and 3mmol Na are sequentially added into autoclave3PO4；
(2) CO is passed through in advance2, and reaction temperature is progressively risen to CO in 170 DEG C, regulation autoclave2Pressure to 6MPa,
10h is reacted under mechanical stirring；
(3) autoclave is cooled to room temperature after the completion of reacting, product is taken out, and using rotary distillation remove solvent and
Water byproduct；
(4) end-product 1- (2- ethoxys) -2- imidazolones, the chromatographic column eluting solvent are afforded by chromatographic column
It is 1 for volume ratio:4 ethanol and dichloromethane mixture.
The yield of above-mentioned 1- (2- ethoxys) -2- imidazolones is 58.2%.
Embodiment 3
With CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material, its step is：
(1) 0.3mol monoethanolamines, 20mL ethanol and 3mmol Li are sequentially added into autoclave3PO4；
(2) CO is passed through in advance2, and reaction temperature is progressively risen to CO in 170 DEG C, regulation autoclave2Pressure to 8MPa,
6h is reacted under mechanical stirring；
(3) autoclave is cooled to room temperature after the completion of reacting, product is taken out, and using rotary distillation remove solvent and
Water byproduct；
(4) end-product 1- (2- ethoxys) -2- imidazolones, the chromatographic column eluting solvent are afforded by chromatographic column
It is 1 for volume ratio:5 ethanol and dichloromethane mixture.
The yield of above-mentioned 1- (2- ethoxys) -2- imidazolones is 28.5%.
Embodiment 4
With CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material, its step is：
(1) 0.3mol monoethanolamines, 20mL ethanol and 3mmol K are sequentially added into autoclave2CO3；
(2) CO is passed through in advance2, and reaction temperature is progressively risen to CO in 130 DEG C, regulation autoclave2Pressure to 2MPa,
8h is reacted under mechanical stirring；
(3) autoclave is cooled to room temperature after the completion of reacting, product is taken out, and using rotary distillation remove solvent and
Water byproduct；
(4) end-product 1- (2- ethoxys) -2- imidazolones, the chromatographic column eluting solvent are afforded by chromatographic column
It is 1 for volume ratio:6 ethanol and dichloromethane mixture.
The yield of above-mentioned 1- (2- ethoxys) -2- imidazolones is 19.7%.
Embodiment 5
With CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material, its step is：
(1) 0.3mol monoethanolamines, 20mL ethanol and 3mmol [BMIm] OH are sequentially added into autoclave；
(2) CO is passed through in advance2, and reaction temperature is progressively risen to CO in 200 DEG C, regulation autoclave2Pressure to 4MPa,
6h is reacted under mechanical stirring；
(3) autoclave is cooled to room temperature after the completion of reacting, product is taken out, and using rotary distillation remove solvent and
Water byproduct；
(4) end-product 1- (2- ethoxys) -2- imidazolones, the chromatographic column eluting solvent are afforded by chromatographic column
It is 1 for volume ratio:4 ethanol and dichloromethane mixture.
The yield of above-mentioned 1- (2- ethoxys) -2- imidazolones is 42.9%.
Claims (1)
1. with CO2The method that 1- (2- ethoxys) -2- imidazolones are prepared for raw material, it is characterised in that
（1）The catalyst K of monoethanolamine, alcohol solvent and alkali compounds is sequentially added into autoclave3PO4；The ethanol
The mol ratio of the catalyst of amine and alkali compounds is 1:0.01；
（2）It is passed through CO in advance2, and reaction temperature is progressively risen to CO in 170~190 DEG C, regulation autoclave2Pressure to 6~
6~10h is reacted under 8MPa, mechanical agitation；
（3）Autoclave is cooled to room temperature after the completion of reaction, product is taken out, and solvent and by-product are removed using rotary distillation
Thing water；
（4）End-product 1- (2- ethoxys) -2- imidazolones are afforded by chromatographic column, the chromatographic column eluting solvent is body
Product is than being 1:4~6 ethanol and dichloromethane mixture.
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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104860886A CN104860886A (en) | 2015-08-26 |
| CN104860886B true CN104860886B (en) | 2017-08-25 |
Family
ID=53907121
Family Applications (1)
| 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 |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104860886B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019030191A1 (en) * | 2017-08-11 | 2019-02-14 | Akzo Nobel Chemicals International B.V. | Process for manufacturing a cyclic urea adduct of an ethyleneamine compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9101690D0 (en) * | 1991-01-25 | 1991-03-06 | Bp Chem Int Ltd | Process |
-
2015
- 2015-05-26 CN CN201510274783.7A patent/CN104860886B/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| CN104860886A (en) | 2015-08-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zhang et al. | A silica gel supported dual acidic ionic liquid: an efficient and recyclable heterogeneous catalyst for the one-pot synthesis of amidoalkyl naphthols | |
| Shi et al. | Application of the polyacrylonitrile fiber as a novel support for polymer-supported copper catalysts in terminal alkyne homocoupling reactions | |
| CN105585501B (en) | Ethylenediamine production method | |
| CN101723771A (en) | Novel method for preparing beta-aminoketone, ester, nitrile and amide derivatives through catalysis of functional ionic liquid | |
| CN105037061A (en) | Method for synthesizing carbamic ester through alkyl boronic acid, amine and carbon dioxide | |
| WO2023109968A3 (en) | Synthesis method for finerenone and intermediate thereof | |
| CN104860886B (en) | With CO2The method that 1 (2 ethoxy) 2 imidazolones are prepared for raw material | |
| CN113444039B (en) | Method for preparing 2,2, 4-trimethyl-1, 2-dihydroquinoline by using ionic liquid | |
| CN100357266C (en) | Process for producing methyl carbamate | |
| CN110240708A (en) | A kind of synthesis in water covalent organic frame material and preparation method thereof | |
| CN101928222B (en) | Synthesis method of N, N, N', N'-tetraisopropyl ethylene diamine | |
| Azizi et al. | Ultrasound mediated efficient ring opening of epoxides by in situ generated dithiocarbamates in green reaction media | |
| CN112745267B (en) | Imidazolyl ionic liquid and application thereof | |
| CN101481330A (en) | Preparation of N-(4-ethoxy carbonyl phenyl)-N'-methyl-N'-phenyl formamidine | |
| CN103896907B (en) | A kind of method being prepared Isosorbide-5-Nitrae-dioxane by 1,3-dioxolane | |
| CN102267913B (en) | Synthetic method of 2,3-dimethyl-2,3-dinitrobutane | |
| CN108623493B (en) | Under mild condition with CO2N-formylation synthesis method for carbon source | |
| CN108484451B (en) | Method for preparing 1, 2-aminoalcohol compound by one-pot method | |
| CN105732694A (en) | Method for adsorbing and purifying 1, 1, 1, 3, 5, 5, 5-heptamethyltrisiloxane | |
| CN105170180A (en) | Application of 4,5-methylene-L-proline as catalyst in direct asymmetric Aldol reaction | |
| CN101456792A (en) | Method for preparing diatomic alcohol compounds by annular carbonic acid esters hydrolysis | |
| CN105111101B (en) | Method for preparing N-cyanoethyl-N-ethoxylaniline by using ionic liquid | |
| CN102267914B (en) | Method for preparing 2,3-dimethyl-2,3-dinitrobutane | |
| CN103772240A (en) | Method for preparation of methylene diphenyl diisocyanate (MDI) | |
| CN108358886A (en) | A method of preparing trimethylene list sulfocarbonate with ionic liquid-catalyzed |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| EXSB | Decision made by sipo to initiate substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
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 |