CN112457237A - Preparation method and application of N-ethyl carbazole - Google Patents
Preparation method and application of N-ethyl carbazole Download PDFInfo
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- CN112457237A CN112457237A CN202011474132.XA CN202011474132A CN112457237A CN 112457237 A CN112457237 A CN 112457237A CN 202011474132 A CN202011474132 A CN 202011474132A CN 112457237 A CN112457237 A CN 112457237A
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- Prior art keywords
- carbazole
- preparation
- reaction kettle
- reaction
- bromoethane
- 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.)
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- PLAZXGNBGZYJSA-UHFFFAOYSA-N 9-ethylcarbazole Chemical compound C1=CC=C2N(CC)C3=CC=CC=C3C2=C1 PLAZXGNBGZYJSA-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims abstract description 66
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 57
- 238000006243 chemical reaction Methods 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 23
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 claims abstract description 21
- 235000011121 sodium hydroxide Nutrition 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000004321 preservation Methods 0.000 claims abstract description 6
- 238000007789 sealing Methods 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 238000005070 sampling Methods 0.000 claims abstract description 5
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 5
- CHQVQXZFZHACQQ-UHFFFAOYSA-M benzyl(triethyl)azanium;bromide Chemical compound [Br-].CC[N+](CC)(CC)CC1=CC=CC=C1 CHQVQXZFZHACQQ-UHFFFAOYSA-M 0.000 claims description 5
- 239000000049 pigment Substances 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 3
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 claims description 3
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 18
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 7
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
Abstract
The invention belongs to the technical field of compound preparation, and particularly relates to a preparation method and application of N-ethyl carbazole. A preparation method of N-ethyl carbazole comprises the following steps: s1: adding liquid caustic soda, carbazole, a catalyst and a solvent into a reaction kettle, sealing the reaction kettle, replacing the reaction kettle with nitrogen for 3-5 times, vacuumizing to the vacuum degree of-0.07 MPa-0.2MPa, and reacting; s2: controlling the reaction temperature to be 30-40 ℃, dropwise adding bromoethane into the reaction kettle, heating to 75-90 ℃ after dropwise adding, and carrying out heat preservation reaction for 1-2 hours; s3: and (4) sampling from the step S2 to analyze the carbazole content, when the carbazole content is lower than 0.02%, heating to 120-130 ℃, distilling, standing for 30-90 minutes, and separating out a lower layer solution to obtain the N-ethyl carbazole. According to the method, the o-dichlorobenzene is adopted, so that the use of pure benzene is avoided, the existence of harmful substances is reduced, and the national environment-friendly production requirement is met; on the other hand, the secondary solvent can be directly used for the next experiment reaction, so that the waste of raw materials is reduced, and the cost is saved.
Description
Technical Field
The invention belongs to the technical field of compound preparation, and particularly relates to a preparation method and application of N-ethyl carbazole.
Background
N-Ethylcarbazole, white needle-like crystals, dissolved in hot ethanol, diethyl ether, acetone, chlorobenzene and pentane. Is insoluble in water. And (5) sealing and storing. Can be used as dye intermediate, agricultural chemicals, and reagent. Is used in dye industry to produce permanent violet RL.
However, in the traditional preparation of N-ethyl carbazole, carbazole is dissolved by pure benzene, potassium hydroxide and polyethylene glycol, and then the N-ethyl carbazole is prepared by performing alkylation reaction on diethyl sulfate at 107 ℃. Because pure benzene is used as a solvent in the preparation process, when N-ethyl carbazole is used as a raw material to be applied to food packaging or textiles, toluene residue may cause harm to human bodies.
Therefore, optimizing and improving the preparation process and the preparation raw materials of the N-ethyl carbazole become important researches for expanding the N-ethyl carbazole.
Disclosure of Invention
In order to solve the above technical problems, a first aspect of the present invention provides a method for preparing N-ethylcarbazole, comprising the steps of:
s1: adding liquid caustic soda, carbazole, a catalyst and a solvent into a reaction kettle, sealing the reaction kettle, replacing the reaction kettle with nitrogen for 3-5 times, vacuumizing to the vacuum degree of-0.07 MPa-0.2MPa, and reacting;
s2: controlling the reaction temperature to be 30-40 ℃, dropwise adding bromoethane into the reaction kettle, heating to 75-90 ℃ after dropwise adding, and carrying out heat preservation reaction for 1-2 hours;
s3: and (4) sampling from the step S2 to analyze the carbazole content, when the carbazole content is lower than 0.02%, heating to 120-130 ℃, distilling, standing for 30-90 minutes, and separating out a lower layer solution to obtain the N-ethyl carbazole.
As a preferable technical solution, the weight ratio of the liquid alkali and the carbazole in the step S1 is 1: 0.8-2.
As a preferable technical scheme, the liquid caustic soda in the step S1 is liquid caustic soda with a mass concentration of 30-45%.
As a preferable technical solution, the weight ratio of bromoethane to carbazole in the step S2 is 1: 1-3.
As a preferred technical scheme, the weight ratio of bromoethane to carbazole is 1: 1-2.
As a preferred technical scheme, the weight of the catalyst in the S1 step is 0.7-1.2 wt% of the weight of carbazole.
As a preferred technical scheme, the catalyst is selected from at least one of benzyl trimethyl ammonium chloride, benzyl trimethyl ammonium bromide, benzyl triethyl ammonium chloride and benzyl triethyl ammonium bromide.
As a preferable technical proposal, the vacuum degree in the step S1 is-0.07 MPa.
As a preferred technical scheme, the heat preservation reaction time of the step S2 is 1 hour.
In a second aspect of the invention, the invention provides an application of a preparation method of N-ethyl carbazole in pigment preparation.
Has the advantages that:
1. the preparation method of N-ethyl carbazole developed by the invention eliminates the use of pure benzene, reduces the existence of harmful substances, and meets the national environmental protection production requirement;
2. the preparation method of the N-ethyl carbazole, which is developed by the invention, adopts a method of dripping the bromoethane at a low temperature, so that the volatilization of the bromoethane is reduced, the safety of experimenters is ensured, and the environmental pollution risk and the safety risk in the production process are avoided;
3. the preparation method of the N-ethyl carbazole developed by the application avoids a complex post-treatment process, can be directly used for the next experimental reaction, reduces the waste of raw materials and saves the cost.
Detailed Description
The invention will be further understood by reference to the following detailed description of preferred embodiments of the invention and the examples included therein. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application belongs. To the extent that a definition of a particular term disclosed in the prior art is inconsistent with any definitions provided herein, the definition of the term provided herein controls.
As used herein, a feature that does not define a singular or plural form is also intended to include a plural form of the feature unless the context clearly indicates otherwise. It will be further understood that the term "prepared from …," as used herein, is synonymous with "comprising," including, "comprising," "having," "including," and/or "containing," when used in this specification means that the recited composition, step, method, article, or device is present, but does not preclude the presence or addition of one or more other compositions, steps, methods, articles, or devices. Furthermore, the use of "preferred," "preferably," "more preferred," etc., when describing embodiments of the present application, is meant to refer to embodiments of the invention that may provide certain benefits, under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. In addition, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
In order to solve the above technical problems, a first aspect of the present invention provides a method for preparing N-ethylcarbazole, comprising the steps of:
s1: adding liquid caustic soda, carbazole, a catalyst and a solvent into a reaction kettle, sealing the reaction kettle, replacing the reaction kettle with nitrogen for 3-5 times, vacuumizing to the vacuum degree of-0.07 MPa-0.2MPa, and reacting;
s2: controlling the reaction temperature to be 30-40 ℃, dropwise adding bromoethane into the reaction kettle, heating to 75-90 ℃ after dropwise adding, and carrying out heat preservation reaction for 1-2 hours;
s3: and (4) sampling from the step S2 to analyze the carbazole content, when the carbazole content is lower than 0.02%, heating to 120-130 ℃, distilling, standing for 30-90 minutes, and separating out a lower layer solution to obtain the N-ethyl carbazole.
The preparation process of the N-ethyl carbazole is represented by a chemical reaction formula as follows:
in some preferred embodiments, the solvent described in step S1 is selected from ortho-dichlorobenzene.
In some preferred embodiments, the raw materials for preparing the N-ethyl carbazole comprise the following components in parts by weight: 200 parts of o-dichlorobenzene, 30-80 parts of carbazole, 15-80 parts of liquid alkali, 20-54 parts of bromoethane and 0.1-1 part of catalyst.
In some preferred embodiments, the weight ratio of the liquid base and the carbazole in the step S1 is 1: 0.8-2.
In some preferred embodiments, the weight ratio of the liquid base and the carbazole in the step S1 is 1: 1.
in some preferred embodiments, the liquid caustic soda in the step of S1 is liquid caustic soda with a mass concentration of 30-45%.
In some preferred embodiments, the liquid caustic soda in the step of S1 is 45% by mass.
In some preferred embodiments, the method for preparing the liquid caustic soda with the mass concentration of 45% comprises the following steps:
weighing liquid caustic soda with the mass concentration of 30%, adding caustic soda flakes, and adjusting the mass concentration of the caustic soda flakes to 45%.
In some preferred embodiments, the weight ratio of bromoethane to carbazole in step S2 is 1: 1-3.
In some preferred embodiments, the weight ratio of bromoethane to carbazole is 1: 1-2.
In some preferred embodiments, the weight ratio of bromoethane to carbazole in step S2 is 1: 1.5.
in some preferred embodiments, the weight of the catalyst in step S1 is 0.7 to 1.2 wt% of the weight of carbazole.
In some preferred embodiments, the catalyst is selected from at least one of benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, and benzyltriethylammonium bromide.
In some preferred embodiments, the catalyst is selected from benzyltriethylammonium bromide.
In some preferred embodiments, the vacuum level in step S1 is-0.07 MPa.
In some preferred embodiments, the incubation reaction time in step S2 is 1 hour.
In the experimental process, the applicant finds that the bromoethane can be dropwise added at low temperature by adopting the preparation method of the bromoethane developed by the application, so that volatilization of the bromoethane is avoided, pollution to the environment is avoided, harm to the body of an experimenter is also avoided, and the preparation method is safe. Meanwhile, the application adopts o-dichlorobenzene, so that the use of pure benzene is avoided, the existence of harmful substances is reduced, and the national environment-friendly production requirement is met; on the other hand, the secondary solvent can be directly used for the next experiment reaction, so that the waste of raw materials is reduced, and the cost is saved.
In a second aspect of the invention, the invention provides an application of a preparation method of N-ethyl carbazole in pigment preparation.
The present invention will be specifically described below by way of examples. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and that the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above disclosure are still within the scope of the present invention.
In addition, the starting materials used are all commercially available, unless otherwise specified.
Examples
Example 1
A preparation method of N-ethyl carbazole comprises the following steps:
s1: adding liquid caustic soda, carbazole, a catalyst and a solvent into a reaction kettle, sealing the reaction kettle, replacing the reaction kettle with nitrogen for 3 times, vacuumizing to the vacuum degree of-0.07 MPa, and reacting;
s2: controlling the reaction temperature to be 35 ℃, dropwise adding bromoethane into the reaction kettle, heating to 80 ℃ after dropwise adding, and carrying out heat preservation reaction for 1 hour;
s3: and (4) sampling from the step S2 to analyze the carbazole content, heating to 120 ℃ when the carbazole content is lower than 0.02%, distilling, standing for 60 minutes, and separating out a lower layer solution to obtain the N-ethyl carbazole.
The solvent in the step S1 is selected from ortho-dichlorobenzene;
the preparation raw materials of the N-ethyl carbazole comprise the following components in parts by weight: 100 parts of o-dichlorobenzene, 60 parts of carbazole, 60 parts of liquid alkali, 40 parts of bromoethane and 0.6 part of catalyst.
The catalyst is benzyl triethyl ammonium bromide, and is purchased from Hubei Xin Rundg chemical Co., Ltd.
The preparation method of the liquid caustic soda with the mass concentration of 45% comprises the following steps:
weighing liquid caustic soda with the mass concentration of 30%, adding caustic soda flakes, and adjusting the mass concentration of the caustic soda flakes to 45%.
Liquid caustic soda, cat 1192, purchased from Kyobo chemical Co., Ltd; carbazole, available from mclin chemical reagent net.
A preparation method of N-ethyl carbazole is used for preparing permanent violet RL pigment.
Example 2
The specific implementation mode of the preparation method of N-ethyl carbazole is the same as that of example 1, and the difference of the preparation method from example 1 is that the weight part of liquid alkali is 10 parts.
Example 3
The preparation process of N-ethyl carbazole is the same as that in example 1, except that the amount of bromoethane in example 1 is 20 weight portions.
Example 4
The specific implementation mode of the preparation method of N-ethyl carbazole is the same as that of example 1, and the difference from example 1 is that pure benzene is adopted as the solvent.
Example 5
The specific implementation mode of the preparation method of N-ethyl carbazole is the same as that of example 1, and bromoethane is added all at once in the step of S2 which is different from that of example 1.
Example 6
The specific implementation mode of the preparation method of N-ethyl carbazole is the same as that of example 1, and the reaction is carried out for 0.5 hour under the condition of keeping the temperature in the S2 step which is different from that of example 1.
Example 7
The specific implementation mode of the preparation method of N-ethyl carbazole is the same as that of example 1, and the reaction is carried out for 3 hours in the S2 step which is different from that of example 1.
And (3) performance testing:
the yields of N-ethylcarbazole prepared in examples 1-7 are reported in table 1 below.
Table 1:
finally, it should be understood that the above description is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and any modification, equivalent replacement, or improvement made within the protection principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A preparation method of N-ethyl carbazole is characterized by comprising the following steps:
s1: adding liquid caustic soda, carbazole, a catalyst and a solvent into a reaction kettle, sealing the reaction kettle, replacing the reaction kettle with nitrogen for 3-5 times, vacuumizing to the vacuum degree of-0.07 MPa-0.2MPa, and reacting;
s2: controlling the reaction temperature to be 30-40 ℃, dropwise adding bromoethane into the reaction kettle, heating to 75-90 ℃ after dropwise adding, and carrying out heat preservation reaction for 1-2 hours;
s3: and (4) sampling from the step S2 to analyze the carbazole content, when the carbazole content is lower than 0.02%, heating to 120-130 ℃, distilling, standing for 30-90 minutes, and separating out a lower layer solution to obtain the N-ethyl carbazole.
2. The method for preparing N-ethylcarbazole according to claim 1, wherein the weight ratio of said liquid base and said carbazole in step S1 is 1: 0.8-2.
3. The method according to claim 1, wherein the liquid alkali used in the step S1 is 30 to 45 mass%.
4. The method for preparing N-ethylcarbazole according to claim 2, wherein the weight ratio of bromoethane to carbazole in the step of S2 is 1: 1-3.
5. The method of claim 4, wherein the weight ratio of bromoethane to carbazole is 1: 1-2.
6. The method of claim 1, wherein the weight of the catalyst in step S1 is 0.7-1.2 wt% of the carbazole.
7. The method of claim 6, wherein the catalyst is at least one selected from the group consisting of benzyltrimethylammonium chloride, benzyltrimethylammonium bromide, benzyltriethylammonium chloride, and benzyltriethylammonium bromide.
8. The method according to claim 1, wherein the degree of vacuum in the step of S1 is-0.07 MPa.
9. The method according to claim 1, wherein the reaction time in the step of S2 is 1 hour.
10. Use of a process for the preparation of an N-ethylcarbazole according to any one of claims 1 to 9 in the preparation of pigments.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011474132.XA CN112457237A (en) | 2020-12-14 | 2020-12-14 | Preparation method and application of N-ethyl carbazole |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202011474132.XA CN112457237A (en) | 2020-12-14 | 2020-12-14 | Preparation method and application of N-ethyl carbazole |
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| CN112457237A true CN112457237A (en) | 2021-03-09 |
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| CN202011474132.XA Pending CN112457237A (en) | 2020-12-14 | 2020-12-14 | Preparation method and application of N-ethyl carbazole |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101328145A (en) * | 2007-06-22 | 2008-12-24 | 宝山钢铁股份有限公司 | Method for producing N- ethyl carbazole |
| CN102115457A (en) * | 2011-03-05 | 2011-07-06 | 太原理工大学 | Preparation method of N-ethylcarbazole |
| CN102898351A (en) * | 2011-07-26 | 2013-01-30 | 南通海迪化工有限公司 | Method for synthesizing N-alkylcarbazole compound |
-
2020
- 2020-12-14 CN CN202011474132.XA patent/CN112457237A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101328145A (en) * | 2007-06-22 | 2008-12-24 | 宝山钢铁股份有限公司 | Method for producing N- ethyl carbazole |
| CN102115457A (en) * | 2011-03-05 | 2011-07-06 | 太原理工大学 | Preparation method of N-ethylcarbazole |
| CN102898351A (en) * | 2011-07-26 | 2013-01-30 | 南通海迪化工有限公司 | Method for synthesizing N-alkylcarbazole compound |
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Application publication date: 20210309 |