CN115028550A - Preparation method of 1, 3-diphenyl-1-triazene - Google Patents

Preparation method of 1, 3-diphenyl-1-triazene Download PDF

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CN115028550A
CN115028550A CN202110246782.7A CN202110246782A CN115028550A CN 115028550 A CN115028550 A CN 115028550A CN 202110246782 A CN202110246782 A CN 202110246782A CN 115028550 A CN115028550 A CN 115028550A
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triazene
diphenyl
acid
aniline
catalyst
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车鹏华
徐杰
高进
马红
黄义争
苗虹
聂鑫
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Dalian Institute of Chemical Physics of CAS
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Dalian Institute of Chemical Physics of CAS
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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
    • C07C245/22—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond containing chains of three or more nitrogen atoms with one or more nitrogen-to-nitrogen double bonds
    • C07C245/24—Chains of only three nitrogen atoms, e.g. diazoamines
    • 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
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/24—Chromium, molybdenum or tungsten
    • B01J23/30—Tungsten
    • 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
    • B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
    • B01J27/14—Phosphorus; Compounds thereof
    • B01J27/186—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J27/188—Phosphorus; Compounds thereof with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium with chromium, molybdenum, tungsten or polonium
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
    • B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
    • B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
    • B01J31/0285—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre also containing elements or functional groups covered by B01J31/0201 - B01J31/0274
    • 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
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
    • B01J31/08—Ion-exchange resins
    • B01J31/10—Ion-exchange resins sulfonated
    • 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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Abstract

The invention discloses a preparation method of 1, 3-diphenyl-1-triazene, which comprises the step of contacting a mixed material of aniline and methyl nitrite with a solid acid catalyst in the presence of an alcohol solvent for reaction to obtain the 1, 3-diphenyl-1-triazene. The invention adopts environment-friendly solid acid to replace liquid acid as the catalyst, avoids the corrosion of strong acid to equipment, can recycle the catalyst, and provides a green synthesis method for efficiently preparing 1, 3-diphenyl-1-triazene.

Description

Preparation method of 1, 3-diphenyl-1-triazene
Technical Field
The invention relates to a preparation method of 1, 3-diphenyl-1-triazene, in particular to a method for preparing 1, 3-diphenyl-1-triazene by taking aniline and methyl nitrite as raw materials and catalyzing with solid acid, belonging to the field of chemical preparation.
Background
A triazene compound is a compound containing an-N ═ N-NH-structure in the molecule, and is also referred to as a diazoamino compound. Based on a conjugated system formed by three nitrogen atoms, the compound molecules have unique physicochemical properties, can be used as a foaming agent of rubber and resin, can also be used as a building block, and can be widely applied to the fields of medicines, dyes, food additives, polymers and the like.
Currently, several important diazotizing agents are developed sequentially for the preparation of triazenes. For example, conventional triazene preparations are typically carried out under strongly acidic conditions using sodium nitrite as the diazotizing agent. The preparation method has the disadvantages of large consumption of liquid acid and release of toxic gas NO during reaction 2 And many side reactions. The isoamyl nitrite is used for replacing sodium nitrite to prepare triazene, so that NO in the reaction process is avoided 2 However, after the reaction is finished, the temperature needs to be raised for evaporation and removal because the boiling point of isoamyl nitrite which needs to be excessive in the reaction system is higher (99 ℃) and the solubility of isoamyl nitrite with a solvent is good, but the triazene product has poor stability at higher temperature and is easy to be rearranged and converted into a para-amino azobenzene byproduct. While using low-boiling methyl nitrite (-12 ℃) or ethyl ester (17 ℃) as diazotizing agent in HCl, H 2 SO 4 The aniline can be converted into 1, 3-diphenyl-1-triazene under the action of inorganic acid catalyst. Wherein, the excessive methyl nitrite can be removed by slightly raising the temperature, and the excessive methyl nitrite can be cooled and recycled. Nevertheless, the preparation method still adopts liquid acid as the catalyst, and has the problems of serious corrosion to equipment, generation of a large amount of waste liquid and waste residue, difficulty in recycling the catalyst and the like.
Disclosure of Invention
Aiming at the problems in the prior art, the invention aims to provide a preparation method of a triazene compound, namely 1, 3-diphenyl-1-triazene, the method adopts environment-friendly solid acid to replace liquid acid as a catalyst and methyl nitrite to replace sodium nitrite as a diazotization reagent, avoids corrosion of strong acid to equipment and no nitrogen dioxide toxic gas in the reaction process, reduces the generation of waste liquid and waste residue, can recycle the catalyst, and provides a green synthesis method for efficiently preparing the 1, 3-diphenyl-1-triazene.
In order to realize the purpose, the invention adopts the following technical scheme to realize the purpose:
a preparation method of 1, 3-diphenyl-1-triazene comprises the following steps: the mixed material containing aniline and methyl nitrite is contacted with a solid acid catalyst in the presence of an alcohol solvent to react to obtain the 1, 3-diphenyl-1-triazene.
Optionally, the solid acid catalyst is selected from at least one of strong-acid cation exchange resin, Keggin type heteropoly acid and sulfonic acid functionalized imidazole ionic liquid.
Optionally, the strong acid cation exchange resin is selected from at least one of Amberlyst-15, Amberlyst-35, Nafion-H.
Optionally, the Keggin-type heteropoly acid is selected from phosphotungstic heteropoly acid (H) 3 PW 12 O 40 ) Silicotungstic heteropoly acid (H) 4 SiW 12 O 40 ) At least one of (1).
Optionally, the sulfonic acid functionalized imidazole ionic liquid is selected from at least one of 1- (3-sulfonic acid group) propyl-3-methylimidazole phosphotungstate, 1- (3-sulfonic acid group) butyl-3-methylimidazole phosphotungstate, 1- (3-sulfonic acid group) propyl-3-methylimidazole silicotungstate, and 1- (3-sulfonic acid group) butyl-3-methylimidazole silicotungstate.
Optionally, the mass ratio of the solid acid catalyst to the aniline is 0.01: 1-0.2: 1.
Optionally, the mass ratio of the solid acid catalyst to aniline is independently selected from any of 0.01:1, 0.02:1, 0.03:1, 0.05:1, 0.1:1, 0.15:1, 0.2:1, or a range between any two.
Optionally, the alcohol solvent is selected from at least one of methanol and ethanol.
Optionally, the molar ratio of methyl nitrite to aniline is 1:1 to 7: 1.
Optionally, the molar ratio of methyl nitrite to aniline is independently selected from any of 1:1, 1.5:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1 or a range between any two.
Optionally, the molar ratio of the alcohol solvent to the aniline is 1:1 to 25: 1.
Alternatively, the molar ratio of alcohol solvent to aniline is independently selected from any of 1:1, 2:1, 5:1, 10:1, 15:1, 20:1, 25:1, or a range between any two.
Optionally, the reaction temperature is 20-35 ℃, and the reaction time is 1.5-4 h.
The invention has the beneficial effects that:
the invention adopts environment-friendly solid acid to replace liquid acid as the catalyst, avoids the problem of corrosivity of strong acid, is easy to separate and can be recycled, and provides a green synthesis method for efficiently preparing 1, 3-diphenyl-1-triazene.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
Unless otherwise specified, the raw materials and catalysts in the examples of the present application were all purchased commercially.
The yield of 1, 3-diphenyl-1-triazene (triazene) in the examples of the present application is calculated as molar yield:
triazene yield ═ triazene production mol/aniline input mol × 100%
Example 1
0.93g (0.01mol) of freshly distilled aniline and a phosphotungstic heteropoly acid catalyst H are added into a round-bottom flask with a mechanical stirring device 3 PW 12 O 40 0.10g, 5mL of methanol. Slowly introducing 0.01mol of methyl nitrite for reaction for 2 hours at the temperature of 25 ℃. After the reaction was completed, the system was heated to 50 ℃ and the mixture was stirred for another 30 minutes to remove the excess methyl nitrite. Quantitative analysis is carried out on the target product 1, 3-diphenyl-1-triazene by adopting gas chromatography, the yield of the 1, 3-diphenyl-1-triazene is 92mol percent based on the input amount of aniline and is expressed by mol percent (mol percent)。
Example 2
0.93g (0.01mol) of freshly distilled aniline and a silicotungstic heteropoly acid catalyst H are added into a round-bottom flask with a mechanical stirring device 4 SiW 12 O 40 0.14g, and 8mL of methanol. Slowly introducing 0.05mol of methyl nitrite for reaction for 4 hours at the temperature of 30 ℃. After the reaction was completed, the system was warmed to 50 ℃ and the mixture was stirred for another 30 minutes to remove the excess methyl nitrite. The target product 1, 3-diphenyl-1-triazene was quantitatively analyzed by gas chromatography, and the yield of 1, 3-diphenyl-1-triazene was 93 mol%, expressed in mol% based on the aniline charge.
Example 3
To a round-bottomed flask equipped with a mechanical stirring device were added 0.93g (0.01mol) of freshly distilled aniline, 0.05g of Amberlyst-15 catalyst, and 0.8mL of methanol. Slowly introducing 0.03mol of methyl nitrite for reaction for 1.5h at the temperature of 35 ℃. After the reaction was completed, the system was heated to 50 ℃ and the mixture was stirred for another 30 minutes to remove the excess methyl nitrite. The target product 1, 3-diphenyl-1-triazene was quantitatively analyzed by gas chromatography, and the yield of 1, 3-diphenyl-1-triazene was 91 mol%, in terms of mole percent (mol%), based on the aniline charge.
Example 4
After the reaction described in example 3, the reaction solution was filtered to obtain the solid catalyst Amberlyst-15, the solid catalyst was washed with methanol solvent several times, and after filtration and drying, the solid catalyst was directly used for the next diazotization reaction of aniline and methyl nitrite, the reaction conditions and the analytical method were the same as in example 3, and the yield of 1, 3-diphenyl-1-triazene was 88 mol%.
Example 5
To a round-bottomed flask equipped with a mechanical stirring device were added 0.93g (0.01mol) of freshly distilled aniline, 0.19g of Nafion-H (NR50) catalyst, and 8.7mL of ethanol. Slowly introducing 0.06mol of methyl nitrite for reaction for 4 hours at the temperature of 30 ℃. After the reaction was completed, the system was heated to 50 ℃ and the mixture was stirred for another 30 minutes to remove the excess methyl nitrite. The target product 1, 3-diphenyl-1-triazene was quantitatively analyzed by gas chromatography, and the yield of 1, 3-diphenyl-1-triazene was 93 mol%, expressed in mol% based on the aniline charge.
Example 6
A round-bottomed flask equipped with a mechanical stirring device was charged with 0.93g (0.01mol) of freshly distilled aniline, 0.01g of 1- (3-sulfonic acid group) propyl-3-methylimidazol phosphotungstate catalyst, and 2.0mL of methanol. Slowly introducing 0.02mol of methyl nitrite for reaction for 4 hours at the temperature of 25 ℃. After the reaction was completed, the system was warmed to 50 ℃ and the mixture was stirred for another 30 minutes to remove the excess methyl nitrite. The target product 1, 3-diphenyl-1-triazene was quantitatively analyzed by gas chromatography, and the yield of 1, 3-diphenyl-1-triazene was 91 mol%, expressed in mol% based on the aniline input.
Example 7
To a round-bottomed flask equipped with a mechanical stirring device were added freshly distilled aniline 0.93g (0.01mol), 1- (3-sulfonic acid group) butyl-3-methylimidazol silicotungstate catalyst 0.02g, and methanol 5.0 mL. Slowly introducing 0.04mol of methyl nitrite for reaction for 3 hours at the temperature of 30 ℃. After the reaction was completed, the system was heated to 50 ℃ and the mixture was stirred for another 30 minutes to remove the excess methyl nitrite. The target product 1, 3-diphenyl-1-triazene was quantitatively analyzed by gas chromatography, and the yield of 1, 3-diphenyl-1-triazene was 90 mol%, expressed in mole percent (mol%), based on the aniline charge.
Although the present application has been described with reference to a few embodiments, it should be understood that various changes, substitutions and alterations can be made herein without departing from the spirit and scope of the application as defined by the appended claims.

Claims (10)

1. A preparation method of 1, 3-diphenyl-1-triazene is characterized in that: the mixed material containing aniline and methyl nitrite is contacted with a solid acid catalyst in the presence of an alcohol solvent to react to obtain the 1, 3-diphenyl-1-triazene.
2. The method according to claim 1, wherein the solid acid catalyst is selected from at least one or more of a combination of strong acid cation exchange resin, Keggin type heteropolyacids and sulfonic acid functionalized imidazole ionic liquids.
3. The method of claim 2, wherein: the strong acid cation exchange resin is at least one selected from Amberlyst-15, Amberlyst-35 and Nafion-H.
4. The method of claim 2, wherein: the Keggin type heteropoly acid is at least one of phosphotungstic heteropoly acid and silicotungstic heteropoly acid;
the phosphotungstic heteropoly acid is H 3 PW 12 O 40 ；
The silicotungstic heteropoly acid is H 4 SiW 12 O 40 。
5. The method of claim 2, wherein: the sulfonic acid functionalized imidazole ionic liquid is selected from at least one of 1- (3-sulfonic acid group) propyl-3-methylimidazole phosphotungstate, 1- (3-sulfonic acid group) butyl-3-methylimidazole phosphotungstate, 1- (3-sulfonic acid group) propyl-3-methylimidazole silicotungstate and 1- (3-sulfonic acid group) butyl-3-methylimidazole silicotungstate.
6. The method of claim 1, wherein: the mass ratio of the solid acid catalyst to the aniline is 0.01: 1-0.2: 1.
7. The method of claim 1, wherein: the alcohol solvent is selected from at least one of methanol and ethanol.
8. The method of claim 1, wherein: the molar ratio of the methyl nitrite to the aniline is 1: 1-7: 1.
9. A method according to claim 1, characterized in that: the molar ratio of the alcohol solvent to the aniline is 1: 1-25: 1.
10. The method of claim 1, wherein: the reaction temperature is 20-35 ℃, and the reaction time is 1.5-4 h.
CN202110246782.7A 2021-03-05 2021-03-05 Preparation method of 1, 3-diphenyl-1-triazene Pending CN115028550A (en)

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Application publication date: 20220909