CN114409548B - Method for preparing benzylamine compound by photocatalysis - Google Patents
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Abstract
The invention provides a method for preparing a benzylamine compound by photocatalysis. The method comprises the following steps: the aromatic aldehyde compound reacts with ammonia water under the conditions of illumination and inert gas through a photocatalyst to obtain the benzylamine compound. The method for preparing the toluamide compound by photocatalysis can be used for replacing the existing mature organic synthesis process, has mild condition and high selectivity, has universality and is suitable for industrial production.
Description
Technical Field
The invention relates to a preparation method of a compound, in particular to a method for preparing toluamide compounds by photocatalysis, and belongs to the technical field of organic synthesis.
Background
Photocatalytic technology is one of the ideal ways to obtain clean energy from solar energy. In recent years, the photocatalysis organic synthesis technology provides a green and economic technical route for synthesizing various high added value chemicals due to the advantages of mild reaction conditions, no need of using additional redox agents, controllable selectivity and the like.
The benzylamine compound is an industrially important raw material, and has wide application in industries such as fine chemical engineering, biological medicine, material synthesis and the like as an organic synthesis intermediate. Traditional synthesis of benzyl amine is carried out by reductive amination of aldehyde ketone compounds with ammonia and hydrogen. The hydrogen used in the reaction process is very unstable, and the reaction process is dangerous and easy to explode.
The Beller group reports a cobalt-based catalyst for the synthesis of various amines, including primary amines, which uses ammonia for reductive amination, but still requires high pressure hydrogen and ammonia (Gross, t.; seayad, a.m.; ahmad, m.; beller, m. synthesis of Primary Amines: first Homogeneously Catalyzed Reductive Amination with am. Org. Lett.2002,4 (12), 2055-2058.). Besides providing a nitrogen source relative to ammonia, ammonia is a very valuable and industrially promising nitrogen source due to the advantages of safety, easy handling, etc., and has been successfully used for synthesizing benzylamine in catalytic reactions.
The Kempe group reports a nickel-based catalyst for synthesizing benzylamine using ammonia, which avoids the introduction of ammonia gas, but still requires a catalytic reaction process under high pressure hydrogen (1 MPa) and high temperature conditions (700 c) (Hahn, g.; kunnas, p.; de Jonge, n.; kempe, r.general synthesis of primary amines via reductive amination employing a reusable nickel catalyst.nat.catalyst.2019, 2 (1), 71-77.).
Therefore, the research of a novel synthesis method of the high-efficiency, green, safe and high-atom-economy benzyl amine compound and the derivative thereof has very important value.
Disclosure of Invention
In order to solve the technical problems, the invention aims to provide a preparation method of an aniline compound with high efficiency, green, safety and high atom economy.
In order to achieve the above technical object, the present invention provides a method for preparing a benzylamine compound by photocatalysis, the method comprising:
reacting aromatic aldehyde compound with ammonia water under the conditions of light and inert gas by using a photocatalyst to obtain the benzylamine compound shown in the formula,
wherein R is 1, 2, 3, 4 OR 5 substituents attached to the benzene ring, each of said substituents being independently of the others hydrogen, halogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C6-C20 aryl, -OR', -OCF 3 -NHR ', -C (=o) OR ', -NHC (=o) R ' and-C (=o) R ', said R ' being any of H, C-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl and benzyl.
The method for preparing the phenylmethylamine compound by photocatalysis has the following reaction principle:
the method for preparing the benzylamine compound by photocatalysis takes the benzaldehyde compound as a reaction raw material, reduces ammonia and alcohol in ammonia water into benzaldehyde at normal temperature and normal pressure to participate in the photocatalysis reaction, thereby realizing high-efficiency atom utilization rate. In addition, the photocatalysis synthesis has the advantages of no toxicity, safety, high stability, recoverability and the like. The method for synthesizing the benzylamine compound by photocatalysis at normal temperature and normal pressure has very important significance and application prospect.
In one embodiment of the present invention, the aromatic aldehyde compound used has the structure shown below:
wherein R is 1, 2, 3, 4 or 5 substituents attached to the benzene ring,each of the substituents is independently of the others hydrogen, halogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C6-C20 aryl, -OR', -OCF 3 -NHR ', -C (=o) OR ', -NHC (=o) R ' and-C (=o) R ', said R ' being any of H, C-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl and benzyl.
In one embodiment of the invention, the method comprises the steps of:
the aromatic aldehyde compound and the alcohol compound are mixed according to a mole ratio of 1: (1-500), adding ammonia water and a photocatalyst for dispersion to obtain a mixed solution;
the mixed solution is protected by inert atmosphere at the temperature of 0.001-50W/cm 2 Under illumination, controlling the reaction temperature to be-50-200 ℃ and stirring for reaction for 1-48 hours;
the obtained organic phase was dried and concentrated to obtain a benzylamine compound.
In one embodiment of the invention, the photocatalyst is a catalyst-supporting photocatalyst, and comprises a main catalyst and a catalyst auxiliary agent; in a preferred embodiment of the invention, the photocatalyst is a semiconductor material having a bandwidth in the range of 1eV to 4 eV.
In one embodiment of the present invention, the main photocatalyst of the catalyst-supporting photocatalyst is a mixture of one or more of metal oxide semiconductor, metal nitride semiconductor, metal sulfide semiconductor, metal selenide semiconductor, perovskite semiconductor, delafossite semiconductor, carbon-based polymer semiconductor and nitrogen-based polymer semiconductor.
Wherein the metal oxide semiconductor comprises one or a combination of a plurality of Ti, zn, zr, W, V, cu, fe, ce, ta, in or Nb oxide-containing compounds; a metal sulfide semiconductor comprising Cd, zn, cu, W, or a sulfur-containing compound of Bi; a metal selenide semiconductor comprising Cd, zn, cu, W, or a selenium-containing compound of Bi; a metal nitrogen compound semiconductor including a nitrogen-containing compound of C, ti, ga, ge or Ta; a metal oxide semiconductor comprising an oxygen-containing compound of C, ti, ga, ge or Ta.
In a preferred embodiment of the present invention, the metal oxide semiconductor used is titanium dioxide; the adopted metal nitride semiconductor is gallium nitride; the adopted metal sulfide semiconductor is cadmium sulfide; the adopted metal selenide semiconductor is tin selenide; the perovskite semiconductor adopted is tin iodide; the adopted copper iron ore semiconductor is copper aluminum oxide; the carbon-based polymer semiconductor is graphene; the nitrogen-based polymer semiconductor is graphite phase carbon nitride.
In a preferred embodiment of the present invention, the promoter in the promoter-supported photocatalyst employed comprises a combination of one or more of silver, platinum, palladium, copper, nickel, iron, cobalt, gold and their corresponding oxides. More specifically, the loading of the catalyst promoter is 0.05 to 20wt%.
In one embodiment of the invention, the inert gas is He, ar, N 2 、CO 2 CO and H 2 A mixture of one or more of the above components.
In a specific embodiment of the invention, the concentration of the aromatic aldehyde compound in the mixed solution is 1-100mmol/L, the concentration of the photocatalyst is 1-100mg/mL, and the mass fraction of the ammonia water is 1-25wt%.
In one embodiment of the present invention, the alcohol compound is one or more of methanol, ethanol, isopropanol, butanol, pentanol, hexanol, ethylene glycol, cyclohexanol, and glycerin.
The method for preparing the benzylamine compound by photocatalysis realizes the reaction of the aromatic aldehyde compound and the ammonia water to obtain the benzylamine compound by the action of the photocatalyst, can be used for replacing the existing mature organic synthesis process, has mild condition and high selectivity, has universality and is suitable for industrial production.
Drawings
FIG. 1 is a mass spectrum of benzylamine in example 1.
Detailed Description
The invention relates to a method for preparing benzylamine compound by photocatalysis, which comprises the steps of reacting aromatic aldehyde compound with ammonia water under the conditions of illumination and inert gas by a photocatalyst loaded with a catalytic auxiliary agent to obtain the benzylamine compound shown in a formula I,
the aromatic aldehyde compound and ammonia water react to obtain the benzylamine compound through the action of the photocatalyst, can be used for replacing the existing mature organic synthesis process, has mild condition and high selectivity, has universality and is suitable for industrial production. The structural general formula of the aromatic aldehyde compound is shown as a formula II:
in the formula I and the formula II, R is 1, 2, 3, 4 or 5 substituents which are connected on the benzene ring, and each substituent is hydrogen, halogen and C independently 1 -C 10 Alkyl, C 2 -C 10 Alkenyl, C 2 -C 10 Alkynyl, C 6 -C 20 Aryl, -OR', -OCF 3 Any one of-NHR ', -C (=o) OR ', -NHC (=o) R ' and-C (=o) R ', said R ' being H, C 1 -C 6 Alkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Any one of alkynyl, phenyl and benzyl.
The method for preparing the benzylamine compound by photocatalysis specifically comprises the following steps: (a) The aromatic aldehyde compound and the alcohol compound are mixed according to a mole ratio of 1: (1-500), adding ammonia water and a photocatalyst for dispersion to obtain a mixed solution; (b) The mixed solution is protected by inert atmosphere at the temperature of 0.001-50W/cm 2 Stirring for reaction under illumination, and controlling the reaction temperature to be-50-200 ℃; (c) And (c) drying and concentrating the organic phase obtained in the step (b) to obtain the benzylamine compound.
The photocatalyst loaded with the catalyst promoter needs to be a semiconductor material with the bandwidth ranging from 1eV to 4eV so as to ensure the synthesis selectivity. Can be selected from metal oxide semiconductor, metal nitride semiconductor, metal sulfide semiconductor, metal selenide semiconductor, and perovskiteA mixture of one or more of ore semiconductors, delafossite semiconductors, carbon-based polymer semiconductors, and nitrogen-based polymer semiconductors. Namely, the photocatalyst is a metal oxide semiconductor, a metal sulfide (selenide) semiconductor, a metal nitride (oxide) compound semiconductor, a perovskite semiconductor (ABO) 3 ) Delafossite, ABO 2 ) A carbon (nitrogen) based polymer semiconductor material or a combination of any two of the above; a metal oxide semiconductor comprising an oxide of Ti, zn, zr, W, V, cu, fe, ce, ta, in or Nb; a metal sulfur (selenide) semiconductor comprising Cd, zn, cu, W, or a sulfur-containing, selenium compound of Bi; a metal nitrogen (oxygen) compound semiconductor including a nitrogen-containing, oxygen compound of C, ti, ga, ge or Ta. The photocatalyst is also typically loaded with a promoter, which is one or more of Ag, pt, pd, cu, ni, fe, co and Au and their corresponding oxides.
The inert gas is He, ar, N 2 、CO 2 CO or H 2 。
In the step (a), the concentration of the aromatic aldehyde compound in the mixed solution is 1-100mmol/L, and the concentration of the photocatalyst is 1-100 mg/mL. In the step (a), the alcohol is methanol, ethanol, isopropanol, butanol, amyl alcohol, hexanol, glycol, cyclohexanol, or glycerol. The solvent is ammonia water with the mass fraction of 1-25wt%.
The invention will be further illustrated with reference to examples.
Example 1
The present embodiment provides a method for preparing a benzylamine compound by photocatalysis, comprising the steps of:
(a) 50mg of a 1wt% copper/graphene photocatalyst (the synthesis of the copper/graphene photocatalyst is as follows, 400mg of carbon nitride graphene, 53.6mg of cupric chloride dihydrate, 2ml of ethanol and 50ml of water are uniformly mixed, and under the irradiation of an LED lamp simulating sunlight and the protection of nitrogen, stirring for 2-3 hours at room temperature, centrifuging, placing in an oven for drying for 24 hours at 60 ℃, uniformly mixing 80 mu mol of benzaldehyde, 200 mu mol of absolute ethanol and 25wt% ammonia water, and dispersing for 10 minutes by ultrasonic (electric power 80W) to obtain a suspension;
(b) Stirring the dispersed suspension at room temperature under the irradiation of an LED lamp simulating sunlight and the protection of nitrogen for reaction for 6 hours;
(c) Drying and concentrating the organic phase obtained in the step (b) to obtain the benzyl amine
The conversion of benzaldehyde was 99% and the selectivity of benzylamine was 81% as analyzed by gas chromatograph test.
Fig. 1 is a mass spectrum of benzylamine of the present example. By comparison of the standard mass spectrum (fig. 1), it was confirmed that the formation of the xylylenediamine structure was performed.
Example 2
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in step (a), the alcohol used is ethylene glycol; the result of the final step (c) was that the conversion of benzaldehyde was 89% and the selectivity of benzylamine was 82% as analyzed by gas chromatograph test.
Example 3
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in step (a), the alcohol used is glycerol; the result of the final step (c) was that the conversion of benzaldehyde was 79% and the selectivity of benzylamine was 81% as analyzed by gas chromatograph test.
Example 4
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in step (a), the alcohol used is 600. Mu. Mol absolute ethanol; the result of the final step (c) was analyzed by a gas chromatograph test, the conversion of benzaldehyde was 80%, and the selectivity of benzylamine was 92%.
Example 5
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in step (a), the alcohol used is 50. Mu. Mol absolute ethanol; the result of the final step (c) was analyzed by a gas chromatograph test, the conversion of benzaldehyde was 77%, and the selectivity of benzylamine was 91%.
Example 6
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in step (a), the reaction concentration of the reactant used is 8. Mu. Mol benzaldehyde; the result of the final step (c) was analyzed by a gas chromatograph test, the conversion of benzaldehyde was 79%, and the selectivity of benzylamine was 88%.
Example 7
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in step (a), the reaction concentration of the reactant used is 100. Mu. Mol benzaldehyde; the result of the final step (c) was that the conversion of benzaldehyde was 88% and the selectivity of benzylamine was 84% as analyzed by gas chromatograph test.
Example 8
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in the step (a), the ammonia water is 5wt percent; the result of the final step (c) was that the conversion of benzaldehyde was 88% and the selectivity of benzylamine was 56% as analyzed by gas chromatograph test.
Example 9
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in the step (a), the mass fraction of the ammonia water used is 15wt%; the result of the final step (c) was that the conversion of benzaldehyde was 89% and the selectivity of benzylamine was 89% as analyzed by gas chromatograph test.
Example 10
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in the step (a), the photocatalyst used is Pt/CdS (400 mg cadmium sulfide, 97.3mg chloroplatinic acid hexahydrate, 2ml ethanol and 50ml water are uniformly mixed, and then stirred for 2-3 hours at room temperature under the irradiation of an LED lamp simulating sunlight and the protection of nitrogen, centrifuged, and then placed in an oven for drying at 60 ℃ for 24 hours); the result of the final step (c) was that the conversion of benzaldehyde was 80% and the selectivity of benzylamine was 81% as analyzed by gas chromatograph test.
Example 11
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: in the step (a), the photocatalyst used is Au/ZnS (400 mg zinc sulfide, 40.0mg tetrachloro-gold acid trihydrate, 2ml ethanol and 50ml water are uniformly mixed, and then stirred for 2-3 hours at room temperature under the irradiation of an LED lamp simulating sunlight and the protection of nitrogen, and after centrifugation, the mixture is placed in an oven and dried for 24 hours at 60 ℃); the result of the final step (c) was that the conversion of benzaldehyde was 50% and the selectivity of benzylamine was 77% as analyzed by gas chromatograph test.
Example 12
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: the raw material used is 80 mu mol of p-chlorobenzaldehyde, and finally the mixture is stirred and reacted for 7 hours at room temperature to obtain 4-chlorobenzenemethylamine
Wherein the conversion of p-chlorobenzaldehyde is 89%, and the selectivity of 4-chlorobenzenemethylamine is 91%.
Example 13
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: the raw material used is 80 mu mol of 2-methylbenzaldehyde, and finally the mixture is stirred and reacted for 5 hours at room temperature to obtain 2-methylbenzylamine, the conversion rate of the 2-methylbenzaldehyde is 91 percent, and the selectivity of the 4-trifluoromethyl benzene azoxy2-methylbenzene is 92 percent
Example 14
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: the raw material used is 80 mu mol of 3-bromobenzaldehyde, and the 3-bromobenzyl amine can be obtained by stirring and reacting for 6h at room temperature
Wherein the conversion rate of 3-bromobenzaldehyde is 90%, and the selectivity of 3-bromobenzyl amine is 93%.
Example 15
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: the raw material used is 80 mu mol of 4-fluorobenzaldehyde, and finally the mixture is stirred and reacted for 6 hours at room temperature to obtain 4-fluorobenzylamine
Wherein the conversion of 4-fluorobenzaldehyde is 90%, and the selectivity of 4-fluorobenzenemethylamine is 93%.
Example 16
This example provides a method for preparing a benzylamine compound by photocatalysis, which is substantially the same as in example 1, except that: the raw material used is 80 mu mol of N, N-dimethylbenzaldehyde, and finally the mixture is stirred and reacted for 5 hours at room temperature to obtain 4- (N, N-dimethyl) benzyl amine
Wherein the conversion of benzaldehyde is 90% and the selectivity of 4- (N, N-dimethyl) benzylamine is 89%.
Comparative example 1
This example is substantially identical to that of example 1, except that: the photocatalyst used was ZrO 2 (bandwidth 5 eV), the result of the final step (c) is that no benzylamine compound can be obtained.
Comparative example 2
This example is substantially identical to that of example 1, except that: the result of the final step (c) is that the benzylamine compound cannot be obtained without using the photocatalyst.
Comparative example 3
This example is substantially identical to that of example 1, except that: as a result of the final step (c) without light irradiation, no benzylamine compound could be obtained.
Comparative example 4
This example is substantially identical to that of example 1, except that: the reaction is carried out under air conditions, and as a result of the final step (c), no benzylamine compound can be obtained.
Comparative example 5
This example is substantially identical to that of example 1, except that: the reaction temperature was carried out at-75℃and, as a result of the final step (c), a benzylamine compound could not be obtained.
The above embodiments are provided to illustrate the technical concept and features of the present invention and are intended to enable those skilled in the art to understand the content of the present invention and implement the same, and are not intended to limit the scope of the present invention. All equivalent changes or modifications made in accordance with the spirit of the present invention should be construed to be included in the scope of the present invention.
Claims (5)
1. A method for preparing a benzylamine compound by photocatalysis, the method comprising:
mixing aromatic aldehyde compound and alcohol compound, reacting with ammonia water under the conditions of light irradiation and inert gas by using photocatalyst to obtain benzylamine compound,
the chemical formula of the aromatic aldehyde compound is
The chemical formula of the benzylamine compound is
，
Wherein the substituent R in the chemical formula of the aromatic aldehyde compound is the same as the substituent R in the chemical formula of the benzylamine compound and is 1, 2, 3, 4 OR 5 substituents attached to the benzene ring, each of the substituents is independently hydrogen, halogen, C1-C10 alkyl, C2-C10 alkenyl, C2-C10 alkynyl, C6-C20 aryl, -OR', -OCF 3 -NHR ', -C (=o) OR ', -NHC (=o) R ' and-C (=o) R ', said R ' being any of H, C-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, phenyl and benzyl;
the photocatalyst comprises a main catalyst and a catalytic auxiliary agent; when the main catalyst is carbon nitride graphene, the catalytic auxiliary agent is copper; when the main catalyst is CdS, the catalytic auxiliary agent is Pt; when the main catalyst is zinc sulfide, the catalytic auxiliary agent is Au; the loading of the catalyst promoter is 0.05-20wt%.
2. The method according to claim 1, wherein the method comprises the steps of:
the aromatic aldehyde compound and the alcohol compound are mixed according to a mole ratio of 1: (1-500), adding ammonia water and a photocatalyst for dispersion to obtain a mixed solution;
the mixed solution is protected by inert atmosphere at a speed of 0.001-50W/cm 2 Controlling the reaction temperature to be-50 to 200 ℃ under illumination o Stirring and reacting for 1 to 48 hours;
the obtained organic phase was dried and concentrated to obtain a benzylamine compound.
3. The method of claim 1, wherein the inert gas is He, ar, and N 2 A mixture of one or more of the above components.
4. The method according to claim 2, wherein the concentration of the aromatic aldehyde compound in the mixed solution is 1-100mmol/L, the concentration of the photocatalyst is 1-100mg/mL, and the mass fraction of the ammonia water is 1-25wt%.
5. The method of claim 1, wherein the alcohol compound is a mixture of one or more of methanol, ethanol, isopropanol, butanol, pentanol, hexanol, ethylene glycol, cyclohexanol, and glycerol.
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