CN118146116A - Method for preparing imine from nitrobenzene - Google Patents
Method for preparing imine from nitrobenzene Download PDFInfo
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- CN118146116A CN118146116A CN202211587602.2A CN202211587602A CN118146116A CN 118146116 A CN118146116 A CN 118146116A CN 202211587602 A CN202211587602 A CN 202211587602A CN 118146116 A CN118146116 A CN 118146116A
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- nitrobenzene
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 150000002466 imines Chemical class 0.000 title claims abstract description 21
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 title claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical class OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000002994 raw material Substances 0.000 claims abstract description 15
- 150000005181 nitrobenzenes Chemical class 0.000 claims abstract description 13
- 229910002846 Pt–Sn Inorganic materials 0.000 claims abstract description 12
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 9
- 239000002184 metal Substances 0.000 claims abstract description 8
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 3
- 238000002360 preparation method Methods 0.000 claims abstract 2
- 230000035484 reaction time Effects 0.000 claims description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- -1 nitrobenzene compound Chemical class 0.000 claims description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 4
- 229940078552 o-xylene Drugs 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 claims 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- FHMDYDAXYDRBGZ-UHFFFAOYSA-N platinum tin Chemical compound [Sn].[Pt] FHMDYDAXYDRBGZ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000012974 tin catalyst Substances 0.000 abstract description 2
- GTWJETSWSUWSEJ-UHFFFAOYSA-N n-benzylaniline Chemical compound C=1C=CC=CC=1CNC1=CC=CC=C1 GTWJETSWSUWSEJ-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 239000007810 chemical reaction solvent Substances 0.000 description 3
- 239000002608 ionic liquid Substances 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000007126 N-alkylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YALRBUHWXPELQP-UHFFFAOYSA-N 3-fluoro-n-phenylaniline Chemical compound FC1=CC=CC(NC=2C=CC=CC=2)=C1 YALRBUHWXPELQP-UHFFFAOYSA-N 0.000 description 1
- QDHRSLFSDGCJFX-UHFFFAOYSA-N 3-fluorobenzyl alcohol Chemical compound OCC1=CC=CC(F)=C1 QDHRSLFSDGCJFX-UHFFFAOYSA-N 0.000 description 1
- MOOUWXDQAUXZRG-UHFFFAOYSA-N 4-(trifluoromethyl)benzyl alcohol Chemical compound OCC1=CC=C(C(F)(F)F)C=C1 MOOUWXDQAUXZRG-UHFFFAOYSA-N 0.000 description 1
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 description 1
- ZPTVNYMJQHSSEA-UHFFFAOYSA-N 4-nitrotoluene Chemical compound CC1=CC=C([N+]([O-])=O)C=C1 ZPTVNYMJQHSSEA-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007809 chemical reaction catalyst Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000002638 heterogeneous catalyst Substances 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NUZDCRLUAZANAU-UHFFFAOYSA-N n-[[4-(trifluoromethyl)phenyl]methyl]aniline Chemical compound C1=CC(C(F)(F)F)=CC=C1CNC1=CC=CC=C1 NUZDCRLUAZANAU-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- 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
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention provides a preparation method for preparing imine from nitrobenzene. Namely, the imine compound is prepared by taking nitrobenzene compounds and benzyl alcohol compounds as raw materials, taking multiphase bimetal Pt-Sn/gamma-Al 2O3 as a catalyst and taking aromatic hydrocarbon compounds as a solvent, and reacting for 4-48 hours at 100-180 ℃ in a closed reactor under the reaction pressure of 1.0-3.0 MPa. The catalyst is a heterogeneous bimetallic platinum-tin catalyst immobilized on gamma-type alumina, the mass percentage of metal platinum is 0.1-10%, the molar ratio of platinum to tin is 1:1-1:11, and the catalyst can be recycled. The method has the characteristics of readily available raw materials, simple and convenient operation, high catalytic efficiency, convenient post-treatment, environmental friendliness and the like, and has industrial application prospect.
Description
Technical Field
The invention relates to a method for preparing imine from nitrobenzene, in particular to a method for preparing imine compounds with high yield by coupling reaction of nitrobenzene compounds and benzyl alcohol compounds in an organic solvent by taking multiphase bimetal Pt-Sn/gamma-Al 2O3 as a catalyst.
Technical Field
Imine compounds are important organic synthesis intermediates and are widely applied to the fields of medicines, pesticides and the like. There are many methods for preparing imines, and the typical method is to generate corresponding imines by condensing primary amines with aldehydes. The method has simple process, but most of raw aldehyde compounds need to be oxidized from corresponding alcohols, which increases the production cost. In addition, the corresponding imine compound can be produced by condensing an anhydride with a primary amine in an ionic liquid (chinese patent CN 100503557C), but the reaction needs to take place in an ionic liquid, and there are many limitations to the large-scale use of ionic liquids as solvents in industrial production.
In recent years, the N-alkylation reaction of amine based on hydrogen-borrowing strategy can directly prepare the imine compound, which provides a new way for synthesizing imine in green. The method takes alcohol and primary amine as raw materials, and the corresponding imine compound can be generated by dehydration under the action of a transition metal catalyst. The method has simple reaction process and is beneficial to operation. Some work has also been done by our group reporting that a heterogeneous bimetallic Pt-Sn/gamma-Al 2O3 based on a hydrogen-borrowing strategy can efficiently catalyze the N-alkylation of amines to imine compounds in the absence of base (chem. Eur. J.2011,17, 13308-13317) with the catalyst and oxygen as the oxidant. However, the raw material amine compound itself needs to be synthesized from other industrial raw materials in the method, for example, the raw material amine compound is obtained by a method of reducing nitro compounds, nitrile, oxime, amide and other compounds or by a method of ammonolysis of halogenated hydrocarbon, and the like, so that the process route and the cost are correspondingly increased.
Disclosure of Invention
In order to solve the defects in the prior art, the invention takes nitrobenzene compounds and benzyl alcohol compounds as raw materials, and prepares imine compounds under the catalysis of multiphase bimetal Pt-Sn/gamma-Al 2O3. The reaction has the characteristics of easily available raw materials, simple and convenient operation, high catalytic efficiency, convenient post-treatment, environmental friendliness and the like, and the catalyst can be recycled after simple post-treatment, so that the catalyst has industrial application prospect.
In order to achieve the above object, the technical scheme of the present invention is as follows:
A method for preparing imine from nitrobenzene uses nitrobenzene compounds and benzyl alcohol compounds as raw materials, uses multiphase bimetal Pt-Sn/gamma-Al 2O3 as a catalyst, and carries out coupling reaction in a closed reactor under the catalysis of multiphase bimetal Pt-Sn/gamma-Al 2O3 to prepare the imine compounds. And (3) separating the product after the reaction is finished according to a conventional separation and purification method to obtain the imine.
The synthetic route is shown in the following reaction formula:
Based on the above technical scheme, further, the substituent R, R 1 of aryl in the raw material nitrobenzene compound and benzyl alcohol compound can be hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, aryl, halogen, trifluoromethyl and the like, and the number of the substituents is 1-5.
Based on the technical scheme, further, the molar ratio of the nitrobenzene compounds to the benzyl alcohol compounds is 1:1-1:4.
Based on the technical scheme, the reaction catalyst is a heterogeneous bimetallic platinum-tin catalyst immobilized on gamma-type alumina, wherein the mass percentage of the metal platinum is 0.1-10%, the molar ratio of the platinum to the tin is 1:1-1:11, and the molar ratio of the platinum to the nitrobenzene compound is 0.05:100-5:100.
Based on the above technical scheme, the solvent for the reaction of nitrobenzene compounds and benzyl alcohol compounds is an aromatic hydrocarbon solvent, preferably one or more of toluene, ethylbenzene, o-xylene, m-xylene, p-xylene and mesitylene.
Based on the technical scheme, further, the reaction temperature of the nitrobenzene compounds and the benzyl alcohol compounds is 100-180 ℃.
Based on the technical scheme, further, the reaction time of the nitrobenzene compounds and the benzyl alcohol compounds is 4-48h.
Based on the technical scheme, further, the reaction atmosphere is nitrogen or argon, and the reaction pressure is 1.0-3.0MPa.
The invention has the following advantages:
Compared with the traditional method, the method directly takes nitrobenzene compounds and benzyl alcohol compounds as raw materials, shortens the synthetic route of the raw materials, thereby reducing the production cost and ensuring that the raw materials are easy to obtain; the method has the characteristics of safe and controllable reaction process, simple and convenient operation, high catalyst efficiency, high synthesis efficiency, convenient post-treatment, environmental friendliness and the like, and the used heterogeneous catalyst is commercialized, can be recycled for many times after simple treatment, and has industrial application prospect.
Detailed Description
The invention takes nitrobenzene compounds and benzyl alcohol compounds as raw materials and multiphase bimetal Pt-Sn/gamma-Al 2O3 as a catalyst to prepare imine compounds.
The invention will be further described with reference to specific examples, but the scope of the invention is not limited thereto.
Example 1
Into a 25mL sealable reaction tube, nitrobenzene (123 mg,1 mmol), benzyl alcohol (324 mg,3 mmol), catalyst Pt-Sn/gamma-Al 2O3 (98 mg) (wherein the mass percent of Pt is 0.5% and the molar ratio of metal Pt to Sn is 1:3), o-xylene (5 mL) were added, and after the reaction system was replaced with nitrogen, the reaction tube was closed and stirred in an oil bath at 150℃for 24 hours. The conversion rate of nitrobenzene is more than 99% by gas chromatography, the catalyst is removed by centrifuging the reaction mixture, and the recovered catalyst is recycled. Purifying the product by neutral alumina column chromatography, eluting: petroleum ether (60-90 ℃)/ethyl acetate=20:1, giving 178mg of N-benzyl-alkenylaniline in yield 98％.1H NMR(CDCl3,400MHz):δ8.46(s,1H),7.92-7.90(m,2H),7.50-7.46(m,3H),7.41-7.37(m,2H),7.26-7.22(m,3H).
Example 2
The procedure and operation were as in example 1, except that benzyl alcohol (108 mg,1 mmol) was added and the reaction temperature was 140 ℃. 77mg of N-benzyl aniline was obtained in 42% yield.
Example 3
The reaction procedure and operation are as in example 1, except that the catalyst used, pt-Sn/γ -Al 2O3, has a molar ratio of metal Pt to Sn of 1:1, the reaction solvent is ethylbenzene, and the reaction time is 48 hours. 174mg of N-benzyl aniline was obtained in 96% yield.
Example 4
The reaction steps and operations were the same as in example 1, except that the catalyst used in example 1 was 5% by mass of Pt in Pt-Sn/γ -Al 2O3, and the molar ratio of metal Pt to Sn was 1:11, wherein the reaction solvent is mesitylene, and the reaction temperature is 170 ℃. 175mg of N-benzyl aniline was obtained in 97% yield.
Example 5
The reaction steps and operations were the same as in example 1, except that the catalyst used in example 1 was 0.1% by mass of Pt in Pt-Sn/γ -Al 2O3, and the molar ratio of metal Pt to Sn was 1:2, the reaction temperature was 100 ℃. 161mg of N-benzyl aniline was obtained in 89% yield.
Example 6
The reaction procedure and operation were the same as in example 1, except that the catalyst used was used 2 times after recovery, and the reaction time was 24 hours. 173mg of N-benzyl aniline is obtained, and the yield is 95%.
Example 7
The reaction procedure and operation were the same as in example 1, except that the catalyst used was used 5 th time after recovery, and the reaction time was 48 hours. 173mg of N-benzyl aniline is obtained, and the yield is 95%.
Example 8
The procedure and operation were as in example 1, except that, as the reaction materials, 4-nitrotoluene (137 mg,1 mmol) and 4-methoxybenzyl alcohol (414 mg,3 mmol) were used, ethylbenzene/o-xylene (v/v, 1/1) was used as the reaction solvent, the reaction time was 30 hours, the mass percentage of Pt in the catalyst Pt-Sn/gamma-Al 2O3 was 10%, and the molar ratio of metal Pt to Sn was 1:5. yield 219mg of N- (4-methylphenyl) -N- (4-methoxybenzyl) amine 97％.1H NMR(CDCl3,400MHz):δ8.41(s,1H),7.86(d,2H),7.29-6.96(m,6H),3.88(s,3H),2.38(s,3H).
Example 9
The procedure and operation were the same as in example 1, except that 4-nitrochlorobenzene (158 mg,1 mmol) was used as a starting material under an argon atmosphere, and the reaction time was 36 hours. Yield 201mg of N- (4-chlorophenyl) -N-benzylenamine 93％.1H NMR(CDCl3,400MHz):δ8.42(s,1H),7.90-7.86(m,2H),7.50-7.46(m,3H),7.34(d,2H),7.15(d,2H).
Example 10
The procedure and the operation were the same as in example 1, except that the starting material was 4-trifluoromethyl benzyl alcohol (719 mg,4 mmol), and the reaction time was 30 hours. Yield of 242mg of N- (4-trifluoromethyl benzyl) aniline 97％.1H NMR(CDCl3,400MHz):δ8.53(s,1H),8.04(d,2H),7.75(d,2H),7.49-7.42(m,2H),7.35-7.24(m,3H).
Example 11
The procedure and the operation were the same as in example 1, except that 3-fluorobenzyl alcohol (252 mg,2 mmol) was used as a starting material, and the reaction time was 10 hours. Yield of N- (3-fluorobenzenyl) aniline 179mg 90％.1H NMR(CDCl3,400MHz):δ8.43(s,1H),7.70-7.62(m,2H),7.48-7.37(m,3H),7.29-7.15(m,4H).
Claims (7)
1. A process for the preparation of imines from nitrobenzene, characterized in that: the imine compound is prepared by taking nitrobenzene compounds and benzyl alcohol compounds as raw materials, taking multiphase bimetal Pt-Sn/gamma-Al 2O3 as a catalyst and taking aromatic hydrocarbon compounds as a solvent;
The synthetic route is shown in the following reaction formula:
Wherein R, R 1 is hydrogen, alkyl with 1-4 carbon atoms, alkoxy with 1-4 carbon atoms, aryl, halogen and trifluoromethyl, and the number of substituents is 1-5.
2. The synthesis method according to claim 1, wherein: the molar ratio of the nitrobenzene compounds to the benzyl alcohol compounds is 1:1-1:4.
3. The synthesis method according to claim 1, wherein: the mass percentage of the metal platinum in the catalyst is 0.1-10%, the mol ratio of the platinum to the tin is 1:1-1:11, and the mol ratio of the platinum to the nitrobenzene compound is 0.05:100-5:100.
4. The synthesis method according to claim 1, wherein: the solvent is one or more than two of toluene, ethylbenzene, o-xylene, m-xylene, p-xylene and mesitylene.
5. The synthesis method according to claim 1, wherein: the reaction temperature is 100-180 ℃.
6. The synthesis method according to claim 1, wherein: the reaction time is 4-48h.
7. The synthesis method according to claim 1, wherein: when the nitrobenzene compounds react with the benzyl alcohol compounds, the reaction atmosphere is nitrogen or argon, and the reaction pressure is 1.0-3.0MPa.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211587602.2A CN118146116A (en) | 2022-12-05 | 2022-12-05 | Method for preparing imine from nitrobenzene |
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| CN202211587602.2A CN118146116A (en) | 2022-12-05 | 2022-12-05 | Method for preparing imine from nitrobenzene |
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