CN117624089A - Method for producing 2, 5-furandimethylamine by means of 5- (azidomethyl) furan-2-carbaldehyde - Google Patents
Method for producing 2, 5-furandimethylamine by means of 5- (azidomethyl) furan-2-carbaldehyde Download PDFInfo
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- CN117624089A CN117624089A CN202311662706.XA CN202311662706A CN117624089A CN 117624089 A CN117624089 A CN 117624089A CN 202311662706 A CN202311662706 A CN 202311662706A CN 117624089 A CN117624089 A CN 117624089A
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- furan
- azidomethyl
- furandimethylamine
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- VKLGKDZCKSMSHG-UHFFFAOYSA-N [5-(aminomethyl)furan-2-yl]methanamine Chemical compound NCC1=CC=C(CN)O1 VKLGKDZCKSMSHG-UHFFFAOYSA-N 0.000 title claims abstract description 25
- WIYJKZWJJKNXAI-UHFFFAOYSA-N 5-(azidomethyl)furan-2-carbaldehyde Chemical compound [N-]=[N+]=NCC1=CC=C(C=O)O1 WIYJKZWJJKNXAI-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- 239000000243 solution Substances 0.000 claims abstract description 22
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 19
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 9
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000011259 mixed solution Substances 0.000 claims abstract description 8
- 239000007868 Raney catalyst Substances 0.000 claims abstract description 7
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910000564 Raney nickel Inorganic materials 0.000 claims abstract description 7
- 239000004305 biphenyl Substances 0.000 claims abstract description 7
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 7
- -1 diphenyl azide phosphate Chemical compound 0.000 claims abstract description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims abstract description 5
- 238000004821 distillation Methods 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000012074 organic phase Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 238000005406 washing Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 3
- 238000005191 phase separation Methods 0.000 claims description 3
- 239000012295 chemical reaction liquid Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000011031 large-scale manufacturing process Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000012263 liquid product Substances 0.000 description 2
- 238000005580 one pot reaction Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- IOERQLKZUCHUSF-UHFFFAOYSA-N 3-(azidomethyl)furan-2-carbaldehyde Chemical compound [N-]=[N+]=NCc1ccoc1C=O IOERQLKZUCHUSF-UHFFFAOYSA-N 0.000 description 1
- QVYAWBLDJPTXHS-UHFFFAOYSA-N 5-Hydroxymethyl-2-furfural Natural products OC1=CC=C(C=O)O1 QVYAWBLDJPTXHS-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- JAMQTHFDMABXGQ-UHFFFAOYSA-N CNC.O1C=CC=C1 Chemical compound CNC.O1C=CC=C1 JAMQTHFDMABXGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000012824 chemical production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- BTVFCJZKQFDRHI-UHFFFAOYSA-N n,n-dimethylfuran-2-amine Chemical compound CN(C)C1=CC=CO1 BTVFCJZKQFDRHI-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
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- Furan Compounds (AREA)
Abstract
The invention discloses a method for preparing 2, 5-furandimethylamine by 5- (azidomethyl) furan-2-formaldehyde, which comprises the following steps: mixing 5-hydroxymethylfurfural, diphenyl azide phosphate and toluene; adding 1, 8-diazabicyclo [5.4.0] undec-7-ene into the mixed solution in batches, and stirring for reaction; post-treatment is carried out to obtain 5- (azidomethyl) furan-2-formaldehyde; placing a methanol solution of 5- (azidomethyl) furan-2-formaldehyde, raney nickel and ammonia in an autoclave, and introducing 0.4-0.8 MPa hydrogen at a temperature of 40-60 ℃ for reacting for 12-20 hours to obtain a reaction solution; concentrating the reaction solution to remove the solvent to obtain a liquid; and carrying out reduced pressure distillation on the obtained liquid to obtain the 2, 5-furandimethylamine. The invention solves the problems of low production yield, high production cost, high reaction danger and incapability of industrialized production of 2, 5-furandimethylamine in the prior art.
Description
Technical Field
The invention relates to the field of preparation of 2, 5-furandimethylamine, in particular to a method for preparing 2, 5-furandimethylamine by using 5- (azidomethyl) furan-2-formaldehyde.
Background
2, 5-furan dimethylamine is an important biomass derived platform compound, has application in the fields of chemical industry, agriculture, medical treatment and the like, and also contains a large amount of amine substances in some medical intermediates and living macromolecules.
In the market at present, most methods for synthesizing 2, 5-furandimethylamine are still obtained by using ammonia and hydrogen for catalytic reaction, the cost is high, the ammonia has strong corrosiveness and is unfavorable for large-scale production, and the method is reduced by using common metals, but the reaction process is still undefined, the yield is extremely low, the reaction danger is extremely complex, and the post-treatment mode is not suitable for large-scale production.
The Chinese patent application with publication number of CN113149937A (202110309620.3) discloses a preparation method of 2, 5-furandimethylamine, and provides a method for preparing 2, 5-furandimethylamine by catalyzing 5-hydroxymethylfurfural through a one-pot two-step method. Taking 5-hydroxymethylfurfural as a reaction substrate, and carrying out catalytic oxidation-amination on 5-hydroxymethylfurfural in methanol or ethanol solution of methylamine by a metal oxide catalyst to obtain an intermediate product; the second step is to catalytically convert the intermediate product obtained in the first step into 2, 5-furandimethylamine in methanol or ethanol solution of ammonia by a supported catalyst, and the two steps of reactions are carried out in a step by step in one pot. The method adopts wide sources of reaction raw materials, has the advantages of reproducibility, simple and efficient reaction process, mild reaction conditions, simple product separation and purification, simple catalyst preparation and recoverable catalyst. The technical scheme is obtained by using the catalytic reaction of ammonia and hydrogen, the cost is high, and the ammonia has strong corrosiveness and is not beneficial to large-scale production.
Disclosure of Invention
The invention aims to provide a method for preparing 2, 5-furandimethylamine by 5- (azidomethyl) furan-2-formaldehyde, which solves the problems of low production yield, high production cost, high reaction danger and incapability of industrial production of 2, 5-furandimethylamine in the prior art.
In order to solve the above problems, the present invention provides a method for preparing 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde, comprising the steps of:
s1, placing 5-hydroxymethylfurfural, diphenyl azide phosphate and toluene in a container to obtain a mixed solution;
s2, adding 1, 8-diazabicyclo [5.4.0] undec-7-ene into the mixed solution obtained in the step S1 in batches, and stirring for reaction;
s3, adding water and ethyl acetate into the solution after the reaction of S2, and stirring;
s4, carrying out two-phase separation on the solution after stirring the S3, washing an organic phase by using a saturated sodium bicarbonate solution, and spin-drying the obtained organic phase to obtain 5- (azidomethyl) furan-2-formaldehyde;
s5, placing the methanol solution of 5- (azidomethyl) furan-2-formaldehyde, raney nickel and ammonia obtained in the step S4 into an autoclave, and introducing 0.4-0.8 MPa hydrogen at the temperature of 40-60 ℃ for reaction for 12-20 hours to obtain a reaction solution;
s6, concentrating the reaction liquid obtained in the step S5 to remove the solvent to obtain liquid;
and S7, carrying out reduced pressure distillation on the liquid obtained in the step S6 to obtain the 2, 5-furandimethylamine.
The molar ratio of the 5-hydroxymethyl furfural to the diphenyl azide phosphate to the 1, 8-diazabicyclo [5.4.0] undec-7-ene is 0.73-0.93: 0.9 to 1.1:0.9 to 1.1, most preferably 0.236mol:0.283mol:0.283mol.
In step S2, 1, 8-diazabicyclo [5.4.0] undec-7-ene is added to the mixed solution obtained in step S1 in portions.
In the step S2, stirring and reacting at 5-15 ℃.
In the step S2, the mass ratio of the 5- (azidomethyl) furan-2-formaldehyde to the Raney nickel is 0.8-1.2: 0.3 to 0.7, most preferably 1:0.5.
in the step S5, hydrogen with the pressure of 0.5-0.7 MPa is introduced to react for 15-18 hours at the temperature of 45-55 ℃, and most preferably, hydrogen with the pressure of 0.6MPa is introduced to react for 16.5 hours at the temperature of 50 ℃.
Further preferred is a process for the preparation of 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde comprising the steps of:
s1, placing 5-hydroxymethylfurfural, diphenyl azide phosphate and toluene in a container, and cooling;
s2, slowly adding 1, 8-diazabicyclo [5.4.0] undec-7-ene into the solution obtained in the step S1 in batches, and stirring at a low temperature for reacting for one hour;
s3, slowly adding water and ethyl acetate into the S2 system solution, and stirring;
s4, carrying out two-phase separation on the mixed solution of the S3 system, washing an organic phase by using a saturated sodium bicarbonate solution, and spin-drying the obtained organic phase to obtain a tan liquid product;
s5, placing the product obtained in the S4, the Raney nickel and ammonia methanol solution into an autoclave, and introducing 0.6MPa hydrogen to react for 16.5 hours at 50 ℃;
s6, concentrating the liquid obtained in the step S5 to remove the solvent to obtain liquid;
and S7, carrying out reduced pressure distillation on the liquid obtained in the step S6 to obtain light yellow liquid, namely the target product furan dimethylamine.
Compared with the prior art, the invention has the following advantages:
the invention prepares the 2, 5-furandimethylamine by the 5- (azidomethyl) furan-2-formaldehyde, avoids the use of a large amount of ammonia gas in one-step hydrogenation, has fewer byproducts in the reaction process, is easy to remove, and the purification method is suitable for large-scale chemical production.
The whole process of the invention has short reaction time and high efficiency. The method has the advantages of low reaction temperature, low energy consumption, low overall reaction risk, low cost, simple purification mode and easy operation, and is suitable for large-scale industrial production.
Drawings
FIG. 1 is a scheme showing the reaction for synthesizing a compound of the present invention;
FIG. 2 is a nuclear magnetic resonance hydrogen spectrum of a compound of the present invention;
FIG. 3 is a gas chromatogram of the synthesis of a compound of the invention.
Detailed Description
As shown in FIG. 1, a scheme of the reaction of the compounds of the present invention is shown.
Example 15 Synthesis of (azidomethyl) furan-2-carbaldehyde
1, 8-diazabicyclo [5.4.0] undec-7-ene (43 g,0.283 mol) was slowly added to a stirred solution of 5-hydroxymethyl-2-furfural (30 g 99%,0.236 mol), diphenyl azide phosphate (77.7 g,0.283 mol) and toluene (150 mL) at 10℃for reaction at 10 ℃; TLC detection shows that no raw material point exists, and the reaction is completed; water (90 mL) was added to the reaction mixture; extracting the aqueous layer with ethyl acetate (3 x 30 ml); washing the organic layer with saturated sodium bicarbonate solution; the organic layer was dried under vacuum to give 31.6g of a dark brown liquid product, 5- (azidomethyl) furan-2-carbaldehyde.
EXAMPLE 2 Synthesis of 2, 5-Furanyldimethylamine
A methanol solution (5 ml) of 5- (azidomethyl) furan-2-formaldehyde (1 g, 0.0070 mol), raney nickel (0.5 g) and ammonia is placed in a 50ml high-pressure reaction kettle at normal temperature of 25 ℃, 0.6MPa hydrogen is introduced, the system solvent is dried by spinning at 50 ℃ for 16.5 hours, the obtained mixed liquid is distilled to obtain 0.6g (yield of 71.86 percent and purity of 98.03 percent) of yellow clear liquid, as shown in a nuclear magnetic hydrogen spectrogram of a yellow liquid in FIG. 2 and a gas-phase chromatogram in FIG. 3, and the obtained product is 2, 5-furandimethylamine through comparison of characterization data of the product, wherein the structural formula is as follows:
Claims (6)
1. a process for the preparation of 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde comprising the steps of:
s1, placing 5-hydroxymethylfurfural, diphenyl azide phosphate and toluene in a container to obtain a mixed solution;
s2, adding 1, 8-diazabicyclo [5.4.0] undec-7-ene into the mixed solution obtained in the step S1 in batches, and stirring for reaction;
s3, adding water and ethyl acetate into the solution after the reaction of S2, and stirring;
s4, carrying out two-phase separation on the solution after stirring the S3, washing an organic phase by using a saturated sodium bicarbonate solution, and spin-drying the obtained organic phase to obtain 5- (azidomethyl) furan-2-formaldehyde;
s5, placing the methanol solution of 5- (azidomethyl) furan-2-formaldehyde, raney nickel and ammonia obtained in the step S4 into an autoclave, and introducing 0.4-0.8 MPa hydrogen at the temperature of 40-60 ℃ for reaction for 12-20 hours to obtain a reaction solution;
s6, concentrating the reaction liquid obtained in the step S5 to remove the solvent to obtain liquid;
and S7, carrying out reduced pressure distillation on the liquid obtained in the step S6 to obtain the 2, 5-furandimethylamine.
2. The method for preparing 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde according to claim 1, characterized in that the molar ratio of 5-hydroxymethylfurfural, diphenyl azide phosphate, 1, 8-diazabicyclo [5.4.0] undec-7-ene is 0.73-0.93: 0.9 to 1.1:0.9 to 1.1.
3. The process for preparing 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde according to claim 1, characterized in that in step S2 1, 8-diazabicyclo [5.4.0] undec-7-ene is added in portions to the mixed solution obtained in step S1.
4. The process for preparing 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde according to claim 1, characterized in that in step S2 the reaction is stirred at 5-35 ℃.
5. The method for preparing 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde according to claim 1, wherein in step S2, the mass ratio of 5- (azidomethyl) furan-2-carbaldehyde to raney nickel is 0.8-1.2: 0.3 to 0.7.
6. The process for preparing 2, 5-furandimethylamine from 5- (azidomethyl) furan-2-carbaldehyde according to claim 1, characterized in that in step S5, hydrogen is introduced at a temperature of 45-55 ℃ under 0.5-0.7 MPa and reacted for 15-18 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311662706.XA CN117624089A (en) | 2023-12-06 | 2023-12-06 | Method for producing 2, 5-furandimethylamine by means of 5- (azidomethyl) furan-2-carbaldehyde |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311662706.XA CN117624089A (en) | 2023-12-06 | 2023-12-06 | Method for producing 2, 5-furandimethylamine by means of 5- (azidomethyl) furan-2-carbaldehyde |
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| Publication Number | Publication Date |
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| CN117624089A true CN117624089A (en) | 2024-03-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202311662706.XA Pending CN117624089A (en) | 2023-12-06 | 2023-12-06 | Method for producing 2, 5-furandimethylamine by means of 5- (azidomethyl) furan-2-carbaldehyde |
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| Country | Link |
|---|---|
| CN (1) | CN117624089A (en) |
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- 2023-12-06 CN CN202311662706.XA patent/CN117624089A/en active Pending
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