CN113831259B - Synthesis method of aromatic azo compound - Google Patents

Synthesis method of aromatic azo compound Download PDF

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CN113831259B
CN113831259B CN202111308006.1A CN202111308006A CN113831259B CN 113831259 B CN113831259 B CN 113831259B CN 202111308006 A CN202111308006 A CN 202111308006A CN 113831259 B CN113831259 B CN 113831259B
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azo compound
aromatic
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aromatic azo
aromatic amine
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CN113831259A (en
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胡宇强
韩利民
苏鹏康
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Inner Mongolia University of Technology
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    • 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 Table
    • 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

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  • 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. The aromatic amine and the catalyst are mixed according to the molar ratio of 1:0.05-0.06, react for 22-25 h at 95-110 ℃, cool to room temperature after the reaction is finished, extract the product, decompress and evaporate, and separate by silica gel column chromatography to obtain the aromatic azo compound. Compared with the prior main method for synthesizing the azobenzene compound, the method does not need noble metal compounds as catalysts or organic solvent systems, does not need reaction assistants such as oxidants, reducing agents and the like, has mild reaction conditions and higher reaction product yield, can recycle aromatic amine raw materials, does not pollute the environment, and accords with the environment-friendly low-carbon economic development mode.

Description

Synthesis method of aromatic azo compound
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 are used for coloring fibers, papers, inks, leather, plastics, color photographic materials, some azo compounds are also used as acid-base indicators and metal indicators in analytical chemistry, and aromatic azo compounds are widely used as an important compound intermediate in a variety of fields such as organic dyes, biological medicines, food additives, radical inducers, liquid crystal materials, nonlinear optical materials, and the like.
The synthetic method of the aromatic azo compound mainly includes a diazo coupling method, a nitro reduction method, an arylhydrazine oxidation method, an arylamine oxidation method, and the like. However, the synthesis of the aromatic azo compound needs to be performed in an organic solvent, so that VOCs pollution is easy to generate to the environment, meanwhile, expensive noble metal compounds are required to be used as catalysts, and various reaction auxiliary agents are also required, so that the method does not accord with a green low-carbon economic development mode. For example, in the prior art CN113019449a, a polyoxometalate catalyst, an additive, an organic solvent, an aromatic amine compound and an oxidizing agent are used as reaction raw materials, and the product yield is high, but the organic solvent used is toluene, an ether solvent and the like, which is easy to cause environmental pollution. As another example, prior art CN105218395a discloses that raw materials are reacted in an organic solvent in the presence of a catalyst, an auxiliary agent, an accelerator and a base, more additives are used in a reaction system, and the catalyst further contains noble metal palladium, so that the production cost is increased, and green development is not facilitated.
Therefore, how to provide a preparation method for preparing the aromatic azo compound by a one-step method, which has simple preparation method and does not need an organic solvent in a reaction system, has great significance on the current green economic development and environmental protection.
Disclosure of Invention
The invention aims to provide a synthesis method of an aromatic azo compound, which solves the problems that an organic solvent system is needed for preparing the azo compound, more additives are needed, a noble metal catalyst is needed, the environment is not protected and the like in the prior art.
In order to achieve the above object, the present invention provides the following technical solutions:
the invention provides a synthesis method of an aromatic azo compound, which comprises the following steps:
mixing aromatic amine and a catalyst, placing the mixture in a tube-sealing reactor, reacting for 22-25 hours at 95-110 ℃, cooling to room temperature after the reaction is finished, extracting the product, decompressing and evaporating the 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 copper ferrocenyl alkynyl, and the preparation method comprises the following steps:
dissolving cuprous iodide in ammonia water with the mass concentration of 22-25% to obtain solution A; dissolving ferrocene 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 respectively, and drying to obtain the ferrocenyl alkynyl cuprous.
Preferably, in the above synthetic method of an aromatic azo compound, the mass volume ratio of the cuprous iodide to the ammonia water is 28-32 mg:1mL; the mass volume ratio of ferrocene acetylene to 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 1:0.05-0.06.
Preferably, in the above method for synthesizing an aromatic azo compound, the extracting agent 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 according to a volume ratio of 1-2: 4 to 6.
Preferably, in the above synthetic method of an aromatic azo compound, the aromatic amine is one or more of aniline, 4-methoxyaniline and 3-trifluoromethylaniline.
Compared with the prior art, the invention has the following beneficial effects:
according to the method, the aromatic azo compound can be prepared by taking the aromatic amine as a raw material and a ferrocene 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 air in the reactor can play an oxidation role in the reaction process without adding an oxidant and a protective atmosphere. Compared with the prior main method for synthesizing the azobenzene compound, the method does not need noble metal compounds as catalysts or organic solvent systems, does not need reaction assistants such as oxidants, reducing agents and the like, has mild reaction conditions and higher reaction product yield, can recycle aromatic amine raw materials, does not pollute the environment, and accords with the environment-friendly low-carbon economic development mode.
Detailed Description
The invention provides a synthesis method of an aromatic azo compound, which comprises the following steps:
mixing aromatic amine and catalyst, placing the mixture in a tube-sealing reactor, reacting at 95-110 ℃ for 22-25 h, cooling to room temperature after the reaction is finished, extracting the product, 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, still 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 still 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 solution A; dissolving ferrocene 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 respectively, and drying to obtain the ferrocenyl alkynyl cuprous.
In the present invention, the mass to volume ratio of the cuprous iodide to the aqueous ammonia is preferably 28 to 32 mg/1 mL, more preferably 28 to 30 mg/1 mL, still more preferably 29 mg/1 mL; the mass volume ratio of ferrocene acetylene to absolute ethanol is preferably 8-11 mg/1 mL, more preferably 8-10 mg/1 mL, and even more preferably 9.6 mg/1 mL; the volume ratio of the solution A to the solution B is preferably 7 to 8:5 to 6, more preferably 7 to 8:6, and still 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 present invention, the temperature of the reaction is preferably 95 to 110 ℃, more preferably 99 to 107 ℃, still 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 effectively; too high a reaction temperature may cause carbonization and deterioration of the raw materials.
In the present invention, the extractant for extraction is preferably methylene chloride.
In the invention, the eluent of the silica gel column chromatography separation is preferably a mixture of dichloromethane and petroleum ether, and more preferably the volume ratio of dichloromethane to petroleum ether is 1-2: 4-6, more preferably dichloromethane and petroleum ether according to the volume ratio of 1: 4.
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 still more preferably 4-methoxyaniline.
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The embodiment provides ferrocenyl alkynyl cuprous, the structural formula is as follows:
the preparation method comprises the following steps:
1048mg of cuprous iodide is dissolved in 35mL of ammonia water with mass concentration of 23% to obtain solution A; 288mg ferrocene acetylene is dissolved in 30mL absolute ethanol to obtain solution B; dropwise adding the solution B into the solution A, stirring for 30min, generating a large amount of orange-red precipitate, filtering, sequentially washing with water and absolute ethyl alcohol for 3 times, and vacuum drying to obtain 316mg of ferrocenyl cuprous (the measured decomposition temperature is 275 ℃), with a yield of 85.1%.
Example 2
The structural formula of the synthesis of azobenzene is as follows:
5.1mL (55.9 mmol) of aniline and 727.0mg (2.8 mmol) of ferrocenyl cuprous (prepared in example 1) are introduced into a 25mL tube-sealed reactor and reacted at 100℃for 24h with stirring; cooling to room temperature after the reaction is finished, adding 20mL of dichloromethane for extraction, and removing the dichloromethane by decompression evaporation by adopting a rotary evaporator to obtain a crude product; the crude product was eluted with dichloromethane and petroleum ether (dichloromethane: petroleum ether in 1:4 by volume) and subjected to column chromatography on silica gel (200 mesh silica gel) using gradient elution to give azobenzene 4201.8mg (melting point 60-61 ℃ C.) as a pale yellow solid with 99% purity in 82.6% isolated yield.
The nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the product are as follows:
nuclear magnetic resonance data: 1 H NMR(500MHz,CDCl 3 ):δ7.45(m,2H),7.49(m,4H),7.92(m,4H)ppm.
13 C NMR(125MHz,CDCl 3 ):δ122.8,129.0,130.9,152.6.
IR (KBr) v data 690,774,1377,1462,2855,2925cm -1 .
Example 3
The synthesis of 4,4' -dimethoxy azobenzene has the following structural formula:
5.0mL (43.0 mmol) of 4-methoxyaniline and 559.5mg (2.2 mmol) of ferrocenyl cuprous (prepared in example 1) were charged into a 25mL tube-sealed reactor and reacted at 104℃for 23.5h with stirring; cooling to room temperature after the reaction is finished, adding 20mL of dichloromethane for extraction, and removing the dichloromethane by decompression evaporation by adopting a rotary evaporator to obtain a crude product; the crude product was eluted with dichloromethane and petroleum ether (dichloromethane: petroleum ether in 1:5 by volume) and subjected to column chromatography on silica gel (300 mesh silica gel) to give 4,4' -dimethoxyazobenzene 4424.5mg (melting point 161-162 ℃ C.) as a 99% pure red-yellow solid in 85.0% isolation yield.
The nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the product are as follows:
nuclear magnetic resonance data: 1 H NMR(500MHz,CDCl 3 ):δ3.89(s,6H),7.00-7.02(d,4H),7.87-7.90(d,4H).
13 C NMR(125MHz,CDCl 3 ):δ55.5,114.1,125.3,147.3,162.5.
IR (KBr) v data 846,1257,1474,1499,1596,2927,2981cm -1 .
Example 4
The 3,3' -bis (trifluoromethyl) azobenzene is synthesized, and the structural formula is as follows:
5.0mL (39.8 mmol) of 3-trifluoromethylaniline and 494.8mg (1.9 mmol) of ferrocene alkynyl cuprous (prepared in example 1) were charged into a 25mL closed-tube reactor and reacted at 99℃for 25h with stirring; cooling to room temperature after the reaction is finished, adding 20mL of dichloromethane for extraction, and removing the dichloromethane by decompression evaporation by adopting a rotary evaporator to obtain a crude product; the crude product was eluted with dichloromethane and petroleum ether (dichloromethane: petroleum ether in 2:6 by volume) and subjected to column chromatography on silica gel (300 mesh silica gel) to give 3,3' -bistrifluoromethyl azobenzene 4321.5mg (melting point 81-82 ℃ C.) as a 99% pure red-yellow solid in a separation yield of 68.3%).
The nuclear magnetic resonance hydrogen spectrum and carbon spectrum data of the product are as follows:
nuclear magnetic resonance data: 1 H NMR(500MHz,CDCl 3 ):δ7.69(t,2H),7.77(d,2H),8.10(d,2H),8.22(s,2H).
13 C NMR(125MHz,CDCl 3 ):δ119.9,126.6,128.0,129.8,152.4.
infrared spectroscopic data IR (KBr) v: 694,811,1124,1189,1331,1440,1604,2924,3083cm -1 .
The foregoing is merely a preferred embodiment of the present invention and it should be noted that modifications and adaptations to those skilled in the art may be made without departing from the principles of the present invention, which are intended to be comprehended within the scope of the present invention.

Claims (4)

1. A method for synthesizing an aromatic azo compound, comprising the steps of:
mixing aromatic amine and a catalyst, placing the mixture in a tube-sealing reactor, reacting for 22-25 hours at 95-110 ℃, cooling to room temperature after the reaction is finished, extracting the product, decompressing and evaporating the product, and separating by silica gel column chromatography to obtain an aromatic azo compound;
the molar ratio of the aromatic amine to the catalyst is 1:0.05-0.06;
the structural formula of the aromatic amine is as follows:
wherein R is hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl or alkoxy;
the structural formula of the aromatic azo compound is as follows:
wherein R is independently hydrogen, trifluoromethyl, trichloromethyl, tribromomethyl, triiodomethyl or alkoxy;
the catalyst is 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 solution A; dissolving ferrocene 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 respectively, and drying to obtain ferrocenyl alkynyl cuprous;
wherein the mass volume ratio of the cuprous iodide to the ammonia water is 28-32 mg/1 mL; the mass volume ratio of ferrocene acetylene to 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.
2. The method for synthesizing an aromatic azo compound according to claim 1, wherein the extracting agent for extraction is methylene chloride.
3. The method for synthesizing an aromatic azo compound according to claim 1 or 2, wherein the eluent separated by silica gel column chromatography is dichloromethane and petroleum ether in a volume ratio of 1-2: 4 to 6.
4. The method for synthesizing an aromatic azo compound according to claim 1, wherein the aromatic amine is one or more of aniline, 4-methoxyaniline and 3-trifluoromethylaniline.
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