CN113831259A - Synthetic method of aromatic azo compound - Google Patents
Synthetic method of aromatic azo compound Download PDFInfo
- Publication number
- CN113831259A CN113831259A CN202111308006.1A CN202111308006A CN113831259A CN 113831259 A CN113831259 A CN 113831259A CN 202111308006 A CN202111308006 A CN 202111308006A CN 113831259 A CN113831259 A CN 113831259A
- Authority
- CN
- China
- Prior art keywords
- azo compound
- aromatic
- aromatic azo
- synthesizing
- solution
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2282—Unsaturated compounds used as ligands
- B01J31/2295—Cyclic compounds, e.g. cyclopentadienyls
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F17/00—Metallocenes
- C07F17/02—Metallocenes of metals of Groups 8, 9 or 10 of the Periodic System
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/842—Iron
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention belongs to the technical field of azo compounds, and discloses a synthetic method of an aromatic azo compound. According to the invention, aromatic amine and a catalyst are mixed according to a molar ratio of 1: 0.05-0.06, the mixture is reacted at 95-110 ℃ for 22-25 h, the reaction product is cooled to room temperature after the reaction is finished, and the product is extracted, evaporated under reduced pressure and separated by silica gel column chromatography to obtain the aromatic azo compound. Compared with the existing main method for synthesizing azobenzene compounds, the method does not need a noble metal compound as a catalyst, an organic solvent system, an oxidant, a reducing agent and other reaction assistants, has mild reaction conditions, higher reaction product yield, recoverable aromatic amine raw materials, and no pollution of VOCs to the environment, and accords with the green low-carbon economic development mode.
Description
Technical Field
The invention relates to the technical field of azo compounds, in particular to a synthetic method of an aromatic azo compound.
Background
Azo compounds can be used for coloring fibers, paper, ink, leather, plastics and color photographic materials, certain azo compounds can also be used as acid-base indicators and metal indicators in analytical chemistry, and aromatic azo compounds are used as important compound intermediates and widely applied to a plurality of fields such as organic dyes, biological medicines, food additives, free radical initiators, liquid crystal materials, nonlinear optical materials and the like.
As the synthesis method of the aromatic azo compound, there are mainly diazo coupling method, nitro reduction method, arylhydrazine oxidation method, arylamine oxidation method and the like. However, the synthesis of the aromatic azo compound needs to be carried out in an organic solvent, which is likely to cause VOCs pollution to the environment, and at the same time, expensive noble metal compounds are needed as catalysts, and a plurality of reaction aids are needed, which is not in line with the economic development mode of green and low carbon. For example, in the prior art CN113019449A, the reaction raw materials include polyoxometallate catalyst, additive, organic solvent, aromatic amine compound and oxidant, and the product yield is high, but the organic solvent used in the method is toluene, ether solvent and the like, which easily causes environmental pollution. For another example, CN105218395A in the prior art discloses that the raw materials are reacted in an organic solvent in the presence of a catalyst, an auxiliary, a promoter, and an alkali, wherein the reaction system uses a large amount of additives, and the catalyst further contains a noble metal palladium, which increases the production cost and is not favorable for green development.
Therefore, how to provide a preparation method for preparing the aromatic azo compound by a one-step method, which has a simple preparation method and needs no organic solvent in a reaction system, has important significance for the current green economic development and environmental protection.
Disclosure of Invention
The invention aims to provide a synthetic method of an aromatic azo compound, which solves the problems that the preparation of the azo compound in the prior art needs more organic solvent systems and additives, needs noble metal catalysts, is not beneficial to environmental protection and the like.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a synthetic method of an aromatic azo compound, which comprises the following steps:
mixing aromatic amine and a catalyst, placing the mixture in a closed tube reactor, reacting at 95-110 ℃ for 22-25 h, cooling to room temperature after the reaction is finished, and extracting, decompressing and evaporating a product, and separating by silica gel column chromatography to obtain an aromatic azo compound;
the structural formula of the aromatic amine is as follows:
wherein R is hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, alkoxy or nitro;
the structural formula of the aromatic azo compound is as follows:
wherein R is independently hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, alkoxy or nitro.
Preferably, in the above method for synthesizing an aromatic azo compound, the catalyst is ferrocenyl cuprous alkynyl, and the preparation method thereof comprises the following steps:
dissolving cuprous iodide in ammonia water with the mass concentration of 22-25% to obtain a solution A; dissolving ferrocenyl acetylene in absolute ethyl alcohol to obtain a solution B; and dropwise adding the solution B into the solution A, stirring for 20-40 min, filtering the product, sequentially washing with water and absolute ethyl alcohol for 3-5 times, and drying to obtain ferrocenyl cuprous alkynyl.
Preferably, in the synthesis method of the aromatic azo compound, the mass-volume ratio of the cuprous iodide to the ammonia water is 28-32 mg:1 mL; the mass-volume ratio of the ferrocene acetylene to the absolute ethyl alcohol is 8-11 mg:1 mL; the volume ratio of the solution A to the solution B is 7-8: 5-6.
Preferably, in the above method for synthesizing an aromatic azo compound, the molar ratio of the aromatic amine to the catalyst is 1:0.05 to 0.06.
Preferably, in the above method for synthesizing an aromatic azo compound, the extractant used for extraction is dichloromethane.
Preferably, in the above method for synthesizing an aromatic azo compound, the eluent separated by silica gel column chromatography is dichloromethane and petroleum ether at a volume ratio of 1-2: 4-6.
Preferably, in the above method for synthesizing an aromatic azo compound, the aromatic amine is one or more of aniline, 4-methoxyaniline and 3-trifluoromethylaniline.
Through the technical scheme, compared with the prior art, the invention has the following beneficial effects:
the aromatic azo compound can be prepared by taking aromatic amine as a raw material and a ferrocenyl alkynyl cuprous catalyst in a reactor through a one-step method, the aromatic amine is taken as the raw material and also taken as a solvent, and the air in the reactor can play an oxidizing role in the reaction process without adding an oxidant and a protective atmosphere. Compared with the existing main method for synthesizing azobenzene compounds, the method does not need a noble metal compound as a catalyst, an organic solvent system, reaction auxiliaries such as an oxidant and a reducing agent, has mild reaction conditions, high yield of reaction products and recoverable aromatic amine raw materials, does not generate VOCs pollution to the environment, and accords with the green low-carbon economic development mode.
Detailed Description
The invention provides a synthetic method of an aromatic azo compound, which comprises the following steps:
mixing aromatic amine and a catalyst, placing the mixture in a closed tube reactor, reacting for 22-25 h at 95-110 ℃, cooling to room temperature after the reaction is finished, and extracting, decompressing and evaporating the product, and separating by silica gel column chromatography to obtain the aromatic azo compound.
In the present invention, the structural formula of the aromatic amine is preferably:
among them, R is preferably hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, alkoxy, or nitro, more preferably hydrogen, trifluoromethyl, or alkoxy, and even more preferably trifluoromethyl.
In the present invention, the structural formula of the aromatic azo compound is preferably:
among them, R is independently preferably hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, alkoxy, or nitro, more preferably hydrogen, trifluoromethyl, or alkoxy, and even more preferably trifluoromethyl.
In the invention, the catalyst is preferably ferrocenyl alkynyl cuprous, and the preparation method comprises the following steps:
dissolving cuprous iodide in ammonia water with the mass concentration of 22-25% to obtain a solution A; dissolving ferrocenyl acetylene in absolute ethyl alcohol to obtain a solution B; and dropwise adding the solution B into the solution A, stirring for 20-40 min, filtering the product, sequentially washing with water and absolute ethyl alcohol for 3-5 times, and drying to obtain ferrocenyl cuprous alkynyl.
In the invention, the mass-to-volume ratio of cuprous iodide to ammonia water is preferably 28-32 mg:1mL, more preferably 28-30 mg:1mL, and even more preferably 29mg:1 mL; the mass-volume ratio of the ferrocenyl acetylene to the absolute ethyl alcohol is preferably 8-11 mg:1mL, more preferably 8-10 mg:1mL, and even more preferably 9.6mg:1 mL; the volume ratio of the solution A to the solution B is preferably 7-8: 5-6, more preferably 7-8: 6, and even more preferably 7: 6.
In the present invention, the molar ratio of the aromatic amine to the catalyst is preferably 1:0.05 to 0.06, more preferably 1:0.051 to 0.057, and still more preferably 1: 0.053.
In the invention, the reaction temperature is preferably 95-110 ℃, more preferably 99-107 ℃, and more preferably 103 ℃; the reaction time is preferably 22 to 25 hours, more preferably 23 to 25 hours, and still more preferably 23 hours. In the present invention, the reaction temperature is too low to allow the reaction to proceed efficiently; if the reaction temperature is too high, the raw materials may be carbonized and deteriorated.
In the present invention, the extractant for extraction is preferably dichloromethane.
In the invention, the eluent for silica gel column chromatography separation is preferably a mixture of dichloromethane and petroleum ether, and further preferably the mixture of dichloromethane and petroleum ether according to the volume ratio of 1-2: 4-6, more preferably dichloromethane and petroleum ether in a volume ratio of 1: 4, and (4) mixing.
In the present invention, the aromatic amine is preferably one or more of aniline, 4-methoxyaniline, and 3-trifluoromethylaniline, more preferably aniline or 4-methoxyaniline, and even more preferably 4-methoxyaniline.
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
The embodiment provides ferrocenyl alkynyl cuprous provided with the following structural formula:
the preparation method comprises the following steps:
dissolving 1048mg of cuprous iodide in 35mL of 23% ammonia water by mass concentration to obtain a solution A; 288mg of ferroceneacetylene is dissolved in 30mL of absolute ethyl alcohol to obtain a solution B; dropwise adding the solution B into the solution A, stirring for 30min, generating a large amount of orange-red precipitate, filtering the product, sequentially washing with water and absolute ethanol for 3 times, and vacuum drying to obtain 316mg of ferrocenyl alkynyl cuprous (the measured decomposition temperature is 275 ℃) and the yield is 85.1%.
Example 2
And (3) synthesizing azobenzene, wherein the structural formula is as follows:
5.1mL (55.9mmol) of aniline and 727.0mg (2.8mmol) of ferrocenyl cuprous alkynyl (prepared in example 1) are added into a 25mL closed-loop reactor, and the reaction is stirred at 100 ℃ for 24 h; after the reaction is finished, cooling to room temperature, adding 20mL of dichloromethane for extraction, and removing dichloromethane by adopting a rotary evaporator through reduced pressure evaporation to obtain a crude product; the crude product was subjected to silica gel column chromatography (200 mesh silica gel) using dichloromethane and petroleum ether as eluents (dichloromethane: petroleum ether volume ratio: 1: 4) by gradient elution to obtain 4201.8mg of azobenzene as a pale yellow solid with a purity of 99% (melting point measured 60 to 61 ℃) and an isolated yield of 82.6%.
The nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the product are as follows:
nuclear magnetic resonance data:1H NMR(500MHz,CDCl3):δ7.45(m,2H),7.49(m,4H),7.92(m,4H)ppm.
13C NMR(125MHz,CDCl3):δ122.8,129.0,130.9,152.6.
infrared spectrum data IR (KBr) v 690,774,1377,1462,2855,2925cm-1.
Example 3
The synthesis of 4, 4' -bis (methoxy) azobenzene has the following structural formula:
5.0mL (43.0mmol) of 4-methoxyaniline and 559.5mg (2.2mmol) of ferrocenyl alkynyl cuprous oxide (prepared in example 1) are added into a 25mL closed-loop reactor, and the reaction is stirred at 104 ℃ for 23.5 h; after the reaction is finished, cooling to room temperature, adding 20mL of dichloromethane for extraction, and removing dichloromethane by adopting a rotary evaporator through reduced pressure evaporation to obtain a crude product; the crude product was subjected to silica gel column chromatography (300 mesh silica gel) using dichloromethane and petroleum ether as an eluent (dichloromethane: petroleum ether volume ratio: 1: 5) by gradient elution to obtain 4424.5mg of 4, 4' -bismethoxyazobenzene as a red-yellow solid with a purity of 99% (melting point measured 161-162 ℃), and the isolated yield was 85.0%.
The nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the product are as follows:
nuclear magnetic resonance data:1H NMR(500MHz,CDCl3):δ3.89(s,6H),7.00-7.02(d,4H),7.87-7.90(d,4H).
13C NMR(125MHz,CDCl3):δ55.5,114.1,125.3,147.3,162.5.
infrared spectrum data IR (KBr) v 846,1257,1474,1499,1596,2927,2981cm-1.
Example 4
The synthesis of 3, 3' -bis (trifluoromethyl) azobenzene has the following structural formula:
5.0mL (39.8mmol) of 3-trifluoromethylaniline and 494.8mg (1.9mmol) of ferrocenyl alkynyl cuprous oxide (prepared in example 1) were added into a 25mL closed-loop reactor, and the reaction was stirred at 99 ℃ for 25 h; after the reaction is finished, cooling to room temperature, adding 20mL of dichloromethane for extraction, and removing dichloromethane by adopting a rotary evaporator through reduced pressure evaporation to obtain a crude product; the crude product was subjected to silica gel column chromatography (300 mesh silica gel) using dichloromethane and petroleum ether as eluents (dichloromethane: petroleum ether volume ratio: 2: 6) by gradient elution to obtain 4321.5mg of 3, 3' -bistrifluoromethylazobenzene as a red-yellow solid with a purity of 99% (melting point was determined to be 81-82 ℃), and the separation yield was 68.3%.
The nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the product are as follows:
nuclear magnetic resonance data:1H NMR(500MHz,CDCl3):δ7.69(t,2H),7.77(d,2H),8.10(d,2H),8.22(s,2H).
13C NMR(125MHz,CDCl3):δ119.9,126.6,128.0,129.8,152.4.
infrared spectrum data IR (KBr) v 694,811,1124,1189,1331,1440,1604,2924,3083cm-1.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (6)
1. A method for synthesizing an aromatic azo compound, comprising the steps of:
mixing aromatic amine and a catalyst, placing the mixture in a closed tube reactor, reacting at 95-110 ℃ for 22-25 h, cooling to room temperature after the reaction is finished, and extracting, decompressing and evaporating a product, and separating by silica gel column chromatography to obtain an aromatic azo compound;
the structural formula of the aromatic amine is as follows:
wherein R is hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, alkoxy or nitro;
the structural formula of the aromatic azo compound is as follows:
wherein R is independently hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl, alkoxy or nitro.
2. The method for synthesizing an aromatic azo compound according to claim 1, wherein the catalyst is ferrocenyl cuprous alkynyl, and the preparation method comprises the following steps:
dissolving cuprous iodide in ammonia water with the mass concentration of 22-25% to obtain a solution A; dissolving ferrocenyl acetylene in absolute ethyl alcohol to obtain a solution B; dropwise adding the solution B into the solution A, stirring for 20-40 min, filtering the product, sequentially washing with water and absolute ethyl alcohol for 3-5 times, and drying to obtain ferrocenyl cuprous alkynyl;
wherein the mass-volume ratio of the cuprous iodide to the ammonia water is 28-32 mg:1 mL; the mass-volume ratio of the ferrocene acetylene to the absolute ethyl alcohol is 8-11 mg:1 mL; the volume ratio of the solution A to the solution B is 7-8: 5-6.
3. The method for synthesizing an aromatic azo compound according to claim 1 or 2, wherein the molar ratio of the aromatic amine to the catalyst is 1:0.05 to 0.06.
4. The method for synthesizing an aromatic azo compound according to claim 3, wherein the extractant used for extraction is dichloromethane.
5. The method for synthesizing the aromatic azo compound according to claim 2 or 4, wherein the eluent obtained by the silica gel column chromatography is dichloromethane and petroleum ether in a volume ratio of 1-2: 4-6.
6. The method for synthesizing an aromatic azo compound according to claim 3, wherein the aromatic amine is one or more of aniline, 4-methoxyaniline, and 3-trifluoromethylaniline.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111308006.1A CN113831259B (en) | 2021-11-05 | 2021-11-05 | Synthesis method of aromatic azo compound |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111308006.1A CN113831259B (en) | 2021-11-05 | 2021-11-05 | Synthesis method of aromatic azo compound |
Publications (2)
Publication Number | Publication Date |
---|---|
CN113831259A true CN113831259A (en) | 2021-12-24 |
CN113831259B CN113831259B (en) | 2023-07-25 |
Family
ID=78971060
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111308006.1A Active CN113831259B (en) | 2021-11-05 | 2021-11-05 | Synthesis method of aromatic azo compound |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN113831259B (en) |
Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1449721A (en) * | 1973-02-01 | 1976-09-15 | Basf Ag | Process for the manufacture of azo compounds |
US20020123494A1 (en) * | 2000-11-03 | 2002-09-05 | Holger Heitsch | Acylaminoalkyl-substituted benzenesulfonamide derivatives, their preparation, their use and pharmaceutical preparations comprising them |
JP2003040850A (en) * | 2001-07-23 | 2003-02-13 | Dainippon Ink & Chem Inc | Method for diazonium salt production and method for aromatic azo compound production |
JP2009178612A (en) * | 2008-01-29 | 2009-08-13 | Niigata Univ | Catalyst for azide-alkyne cycloaddition reaction and method for producing triazole compound by using the same |
CN101573033A (en) * | 2006-11-02 | 2009-11-04 | 默克公司 | Heterocyclyl-substituted anti-hypercholesterolemic compounds |
CN101734648A (en) * | 2009-10-29 | 2010-06-16 | 太原理工大学 | Method for preparing water soluble L-cysteine carbon microsphere derivative |
CN102718680A (en) * | 2012-06-05 | 2012-10-10 | 清华大学 | Method for preparing aromatic azoic compound by catalyzing aromatic amine with metal nanocrystals |
CN104098611A (en) * | 2014-08-05 | 2014-10-15 | 内蒙古工业大学 | Carbon atom bridged chain type multi-ferrocene compound synthesizing method |
US20150047760A1 (en) * | 2012-08-17 | 2015-02-19 | Diehl Bgt Defence Gmbh & Co. Kg | Active composition for a decoy which radiates spectrally on combustion of the active composition, containing an additive |
CN105017065A (en) * | 2014-04-29 | 2015-11-04 | 中国科学院大连化学物理研究所 | Method for preparing aromatic azobenzene by utilizing aromatic amine oxidation |
CN105085329A (en) * | 2014-05-04 | 2015-11-25 | 中国科学院大连化学物理研究所 | Preparation method for aromatic-azoxybenzene by oxidizing aromatic amine |
CN105418691A (en) * | 2015-12-24 | 2016-03-23 | 内蒙古工业大学 | Method for preparing bis-ferrocenyl pyridine derivative in supercritical carbon dioxide |
CN107253920A (en) * | 2017-07-11 | 2017-10-17 | 苏州大学 | A kind of fragrant azobenzene oxide compound and preparation method thereof |
CN107474077A (en) * | 2017-07-03 | 2017-12-15 | 中国科学技术大学 | A kind of α diimine palladium compound catalyst containing ferrocene group and its preparation method and application |
CN109603874A (en) * | 2018-12-11 | 2019-04-12 | 温州大学 | A kind of carbon material, application and the aromatic amine oxidative coupling of the modification of Copper-cladding Aluminum Bar nitrogen are the reaction method of symmetrical/asymmetric azobenzene |
CN109928898A (en) * | 2019-04-09 | 2019-06-25 | 武汉工程大学 | A kind of method that the derivative magnetic nanoparticle of MOFs prepares azoxy compound as recyclable catalyst green |
CN112812034A (en) * | 2021-01-28 | 2021-05-18 | 安庆师范大学 | Azo compound and synthesis method and application thereof |
CN113019449A (en) * | 2020-06-24 | 2021-06-25 | 上海应用技术大学 | Catalytic preparation method of aromatic azoxy compound |
JP2021134141A (en) * | 2020-02-21 | 2021-09-13 | エヌ・イーケムキャット株式会社 | Method for producing aromatic compound using heterogeneous noble metal catalyst |
CN114262284A (en) * | 2021-12-15 | 2022-04-01 | 温州大学 | Method for preparing aromatic azoxy compound based on aromatic amine oxidation |
-
2021
- 2021-11-05 CN CN202111308006.1A patent/CN113831259B/en active Active
Patent Citations (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1449721A (en) * | 1973-02-01 | 1976-09-15 | Basf Ag | Process for the manufacture of azo compounds |
US20020123494A1 (en) * | 2000-11-03 | 2002-09-05 | Holger Heitsch | Acylaminoalkyl-substituted benzenesulfonamide derivatives, their preparation, their use and pharmaceutical preparations comprising them |
JP2003040850A (en) * | 2001-07-23 | 2003-02-13 | Dainippon Ink & Chem Inc | Method for diazonium salt production and method for aromatic azo compound production |
CN101573033A (en) * | 2006-11-02 | 2009-11-04 | 默克公司 | Heterocyclyl-substituted anti-hypercholesterolemic compounds |
JP2009178612A (en) * | 2008-01-29 | 2009-08-13 | Niigata Univ | Catalyst for azide-alkyne cycloaddition reaction and method for producing triazole compound by using the same |
CN101734648A (en) * | 2009-10-29 | 2010-06-16 | 太原理工大学 | Method for preparing water soluble L-cysteine carbon microsphere derivative |
CN102718680A (en) * | 2012-06-05 | 2012-10-10 | 清华大学 | Method for preparing aromatic azoic compound by catalyzing aromatic amine with metal nanocrystals |
US20150047760A1 (en) * | 2012-08-17 | 2015-02-19 | Diehl Bgt Defence Gmbh & Co. Kg | Active composition for a decoy which radiates spectrally on combustion of the active composition, containing an additive |
CN105017065A (en) * | 2014-04-29 | 2015-11-04 | 中国科学院大连化学物理研究所 | Method for preparing aromatic azobenzene by utilizing aromatic amine oxidation |
CN105085329A (en) * | 2014-05-04 | 2015-11-25 | 中国科学院大连化学物理研究所 | Preparation method for aromatic-azoxybenzene by oxidizing aromatic amine |
CN104098611A (en) * | 2014-08-05 | 2014-10-15 | 内蒙古工业大学 | Carbon atom bridged chain type multi-ferrocene compound synthesizing method |
CN105418691A (en) * | 2015-12-24 | 2016-03-23 | 内蒙古工业大学 | Method for preparing bis-ferrocenyl pyridine derivative in supercritical carbon dioxide |
CN107474077A (en) * | 2017-07-03 | 2017-12-15 | 中国科学技术大学 | A kind of α diimine palladium compound catalyst containing ferrocene group and its preparation method and application |
CN107253920A (en) * | 2017-07-11 | 2017-10-17 | 苏州大学 | A kind of fragrant azobenzene oxide compound and preparation method thereof |
CN109603874A (en) * | 2018-12-11 | 2019-04-12 | 温州大学 | A kind of carbon material, application and the aromatic amine oxidative coupling of the modification of Copper-cladding Aluminum Bar nitrogen are the reaction method of symmetrical/asymmetric azobenzene |
CN109928898A (en) * | 2019-04-09 | 2019-06-25 | 武汉工程大学 | A kind of method that the derivative magnetic nanoparticle of MOFs prepares azoxy compound as recyclable catalyst green |
JP2021134141A (en) * | 2020-02-21 | 2021-09-13 | エヌ・イーケムキャット株式会社 | Method for producing aromatic compound using heterogeneous noble metal catalyst |
CN113019449A (en) * | 2020-06-24 | 2021-06-25 | 上海应用技术大学 | Catalytic preparation method of aromatic azoxy compound |
CN112812034A (en) * | 2021-01-28 | 2021-05-18 | 安庆师范大学 | Azo compound and synthesis method and application thereof |
CN114262284A (en) * | 2021-12-15 | 2022-04-01 | 温州大学 | Method for preparing aromatic azoxy compound based on aromatic amine oxidation |
Non-Patent Citations (6)
Title |
---|
LIGANG YAN,等: "Synthesis and catalytic performance of 2-ferrocenylpyridine palladacycle complexes", JOURNAL OF COORDINATION CHEMISTRY, vol. 72, no. 16, pages 2705 - 2721 * |
张骁勇,等: "炔桥联不对称苯基取代双二茂铁衍生物的设计合成和电化学性质", 无机化学学报, vol. 34, no. 05, pages 864 - 873 * |
楚惠元;李晓杰;高子舒;张文博;: "过渡金属催化炔丙基胺的合成研究", 化工管理, no. 16, pages 73 - 74 * |
秦伟静,等: "铜催化合成2-巯基苯并噻唑类衍生物的方法研究", 中国化学会第29届学术年会摘要集, vol. 07, pages 1 * |
陈国英: "醋酸银的手性二茂铁膦胺配合物催化偶氮甲碱叶立德的不对称[3+2]环加成反应研究", 中国优秀硕士学位论文全文数据库工程科技Ⅰ辑, no. 04, pages 014 - 37 * |
韩业晶;: "Sonogashira偶联合成二茂铁类炔烃化合物", 广东化工, no. 02, pages 10 - 11 * |
Also Published As
Publication number | Publication date |
---|---|
CN113831259B (en) | 2023-07-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN107935812B (en) | Method for preparing polyaryl substituted naphthalene derivative by reaction of alkyl aryl ketone and tolane under catalysis of ruthenium | |
CN114349674B (en) | Thiourea compound and preparation method thereof | |
CN113416150B (en) | Synthetic method of lobaplatin intermediate | |
MXPA98000412A (en) | Preparation of 3-hidroxipirazoles n-substitui | |
CN110041223A (en) | Using hydrazine class compound as the method for raw material oxidative synthesis azo compound | |
JP2007182399A (en) | Method for producing fluorenone | |
CN104098607A (en) | Complex and application of monophosphine monoazacyclo-carben nickel containing tricyclic hexyl phosphine | |
CN115974663B (en) | Preparation method and application of trifluoromethyl ketone compound | |
CN113831259A (en) | Synthetic method of aromatic azo compound | |
CN103553856A (en) | Synthetic method of biphenyl compounds | |
CN108276406B (en) | Synthesis method of polycyclic 2-hydrogen pyrazole compound | |
CN113957461B (en) | Electrochemical synthesis method of 1,1' -binaphthyl compound | |
CN106831280B (en) | Method for preparing biaryl compound under solvent-free condition | |
CN112159312B (en) | Synthetic method of triarylmethane compound | |
CN110183380B (en) | Synthesis method and application of 4-hydroxy-1, 8-naphthalimide derivative | |
CN114149314A (en) | Synthetic method of VK2 | |
CN104311469B (en) | A kind of synthetic method of substituted indole-3-acetic acid | |
CN112225657B (en) | Preparation method of flurbiprofen | |
CN107011250B (en) | Synthetic method and application of 2- (2, 6-dichlorophenoxy) pyridine compound | |
CN117050011B (en) | Method for synthesizing 2-methylquinoline by using vinyl acetate as raw material | |
CN107935882B (en) | Method for preparing trans-aromatic tertiary amine azo compound with high stereoselectivity | |
CN117050010B (en) | Synthesis method of 2,2' -biquinoline and derivatives thereof | |
CN114031577B (en) | 2H-benzothiazole C2-aryl acylation method | |
CN103058803A (en) | Biphenyl compound and synthesis method for same | |
CN113105354B (en) | Method for preparing N- (4-hydroxy-3-methoxybenzyl) nonanamide without catalyst |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |