CN112979590A - Novel process for preparing 2-acetylfuran by using furan - Google Patents
Novel process for preparing 2-acetylfuran by using furan Download PDFInfo
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- CN112979590A CN112979590A CN202110226154.2A CN202110226154A CN112979590A CN 112979590 A CN112979590 A CN 112979590A CN 202110226154 A CN202110226154 A CN 202110226154A CN 112979590 A CN112979590 A CN 112979590A
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- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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Abstract
The invention discloses a novel process for preparing 2-acetylfuran by utilizing furan, which comprises the following steps: adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction to obtain an esterification reaction liquid; pumping the esterification reaction liquid at the bottom of the esterification reaction kettle into a circulating condenser, and introducing the esterification reaction liquid into the esterification reaction kettle after condensation and temperature reduction; distilling the esterification reaction liquid under reduced pressure, separating out acetic acid, and refining the residual esterification reaction liquid for multiple times to obtain a crude product; and (3) carrying out reduced pressure distillation on the crude product to obtain a 2-acetylfuran finished product, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and further carrying out reduced pressure distillation to obtain the 2-acetylfuran finished product. The method takes furan as a raw material, and obtains the 2-acetylfuran through esterification, reaction liquid circulation and multiple refining.
Description
Technical Field
The invention relates to the technical field of preparation of organic synthesis intermediates and fine chemical intermediates, in particular to a novel process for preparing 2-acetylfuran by utilizing furan.
Background
2-acetylfuran is an important organic synthesis intermediate and food additive, and 2-acetylfuran can be used for synthesizing various medical and chemical products including furan amine salt, and can also be used in the food industry, such as coffee, meat flavor type edible essence, soup, meat, seasoning and baked food as an additive.
At present, the preparation methods of the acetylfuran are various, but the yield and the purity of the product obtained by different production processes are different, and particularly, the selection of the catalyst brings about more side reactions, thereby influencing the generation of the product and reducing the yield and the purity. Therefore, the method has important practical significance for providing a new process of the 2-acetylfuran.
Disclosure of Invention
In order to solve the problems mentioned in the background art, the present invention provides a novel process for preparing 2-acetylfuran using furan.
In order to achieve the purpose, the invention adopts the following technical scheme:
a new process for preparing 2-acetylfuran by using furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction to obtain an esterification reaction liquid;
Step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling by condensation, and then introducing into the esterification reaction kettle for circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid by using a reboiler, after the rectification is finished, carrying out rough distillation on the reaction liquid, removing the acetic acid again, and finally obtaining a crude product of the 2-acetylfuran;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle, using the obtained 2-acetylfuran finished product in the next working section, transferring the kettle bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and further carrying out reduced pressure distillation to finally obtain the 2-acetylfuran finished product.
Preferably, the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the solid catalyst in the step S1 is 1-5: 1-2:5-10: 0.1-1.
Preferably, the esterification reaction in the step S1 has a temperature of 30-60 ℃ and a pressure of +0.05 MPa.
Preferably, the solid catalyst in the step S1 is 10 to 20% of an organic aluminum oxy compound, 10 to 20% of an imide compound, 20 to 30% of a transition metal compound, and 20 to 30% of a porous silica gel, and the balance is water.
Preferably, the preparation method of the solid catalyst comprises the following steps: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 60-80 ℃, slowly adding porous silica gel, stirring for 0.5-4h, and drying to obtain the solid catalyst.
Preferably, the temperature for condensation and temperature reduction in the step S2 is-10 to 30 ℃.
Preferably, the temperature of the rectification in the step S3 is 85-95 ℃, the temperature of the reduced pressure distillation is 90-100 ℃, and the acetic acid obtained by the crude distillation treatment is recycled to the furan acylation step.
Preferably, the reduced pressure distillation temperature of the crude 2-acetylfuran product in the step S4 is 145-155 ℃, and the setting temperature of the flushing kettle is 130-140 ℃.
Compared with the prior art, the invention has the beneficial effects that:
1. the method takes furan as a raw material, and obtains the 2-acetylfuran through esterification, reaction liquid circulation and multiple refining, and the method can recycle the raw material in the process, reduce resource waste and further improve the utilization rate of the raw material;
2. the invention purifies the product through multiple refining methods including rectification, distillation and the like, so that the purity of the product is improved;
3. according to the invention, the solid catalyst is added in the esterification reaction, and the catalytic material is loaded in the porous silica gel, so that the catalytic effect can be further improved due to the large contact area between the porous silica gel and the raw material during the reaction, and in addition, the solid catalyst made of the porous silica gel can slowly release the main components of the catalyst, thereby avoiding other side reactions caused by overhigh catalytic activity and improving the conversion rate of the raw material;
4. The reaction condition of the invention is simple and easy to carry out, and the reaction is carried out under normal temperature and differential pressure, so that the product is simpler and easier to obtain.
In conclusion, the invention overcomes the defects of the prior art, has reasonable design and higher social use value and application prospect.
Drawings
In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, it is obvious that the drawings in the following description are only some embodiments of the present invention, and for those skilled in the art, other drawings can be obtained according to the drawings without creative efforts.
FIG. 1 is a block diagram of the process flow of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A new process for preparing 2-acetylfuran by using furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction at 30 ℃ and under the pressure of +0.05MPa to obtain an esterification reaction liquid, wherein the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the solid catalyst is 1: 1:5: 0.1;
step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling to-10 ℃ by condensation, and then introducing into the esterification reaction kettle for circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid at 85 ℃ by using a reboiler, after the rectification is finished, carrying out crude distillation on the reaction liquid, removing the acetic acid again at 90 ℃ and recycling the acetic acid to the furan acylation step to finally obtain a 2-acetylfuran crude product;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle at the temperature of 145 ℃, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and carrying out further reduced pressure distillation at the temperature of 130 ℃ to finally obtain the 2-acetylfuran finished product.
In step S1, the solid catalyst is 10% of an organoaluminum oxy-compound, 10% of an imide compound, 20% of a transition metal compound, and 20% of a porous silica gel, and the balance is water, and the specific preparation method is as follows: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 60 ℃, slowly adding porous silica gel, stirring for 4 hours, and drying to obtain the solid catalyst.
Example 2
A new process for preparing 2-acetylfuran by using furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction at 45 ℃ and under the pressure of +0.05MPa to obtain an esterification reaction liquid, wherein the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the solid catalyst is 3: 1.5:8: 0.5;
step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling to 10 ℃, then introducing into the esterification reaction kettle, and carrying out circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid at 90 ℃ by using a reboiler, after the rectification is finished, carrying out crude distillation on the reaction liquid, removing the acetic acid again at 95 ℃ and recycling the acetic acid to the furan acylation step to finally obtain a 2-acetylfuran crude product;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle at the temperature of 150 ℃, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and carrying out further reduced pressure distillation at the temperature of 135 ℃ to finally obtain the 2-acetylfuran finished product.
In step S1, the solid catalyst is 15% of an organoaluminum oxy-compound, 15% of an imide compound, 25% of a transition metal compound, 25% of a porous silica gel, and the balance is water, and the specific preparation method is as follows: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 70 ℃, slowly adding porous silica gel, stirring for 2.5h, and drying to obtain the solid catalyst.
Example 3
A new process for preparing 2-acetylfuran by using furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction at 60 ℃ and under the pressure of +0.05MPa to obtain an esterification reaction liquid, wherein the mass ratio of the acetic acid, the furan, the acetic anhydride and the solid catalyst is 5: 2:10: 1;
step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling to 30 ℃, then introducing into the esterification reaction kettle, and carrying out circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid at 95 ℃ by using a reboiler, after the rectification is finished, carrying out crude distillation on the reaction liquid, removing the acetic acid again at 100 ℃ and recycling the acetic acid to the furan acylation step to finally obtain a 2-acetylfuran crude product;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle at the temperature of 155 ℃, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and carrying out further reduced pressure distillation at the temperature of 140 ℃ to finally obtain the 2-acetylfuran finished product.
In step S1, the solid catalyst is 20% of an organoaluminum oxy-compound, 20% of an imide compound, 25% of a transition metal compound, and 30% of a porous silica gel, and the balance is water, and the specific preparation method is as follows: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 80 ℃, slowly adding porous silica gel, stirring for 0.5h, and drying to obtain the solid catalyst.
Comparative example 1
A process for preparing 2-acetylfuran from furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction at 45 ℃ and under the pressure of +0.05MPa to obtain an esterification reaction liquid, wherein the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the solid catalyst is 3: 1.5:8: 0.5;
step S2: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, and collecting to finally obtain a 2-acetylfuran crude product;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle at the temperature of 150 ℃, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and carrying out further reduced pressure distillation at the temperature of 135 ℃ to finally obtain the 2-acetylfuran finished product.
In step S1, the solid catalyst is 15% of an organoaluminum oxy-compound, 15% of an imide compound, 25% of a transition metal compound, 25% of a porous silica gel, and the balance is water, and the specific preparation method is as follows: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 70 ℃, slowly adding porous silica gel, stirring for 2.5h, and drying to obtain the solid catalyst.
Comparative example 2
A process for preparing 2-acetylfuran from furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction at 45 ℃ and under the pressure of +0.05MPa to obtain an esterification reaction liquid, wherein the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the catalyst is 3: 1.5:8: 0.5;
Step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling to 10 ℃, then introducing into the esterification reaction kettle, and carrying out circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid at 90 ℃ by using a reboiler, after the rectification is finished, carrying out crude distillation on the reaction liquid, removing the acetic acid again at 95 ℃ and recycling the acetic acid to the furan acylation step to finally obtain a 2-acetylfuran crude product;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle at the temperature of 150 ℃, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and carrying out further reduced pressure distillation at the temperature of 135 ℃ to finally obtain the 2-acetylfuran finished product.
In step S1, the catalyst is 15% of an organic aluminum oxy compound, 15% of an imide compound, 25% of a transition metal compound, and the balance water, and the specific preparation method is as follows: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 70 ℃, stirring for 2.5h, and drying to obtain the catalyst.
Comparative example 3
A process for preparing 2-acetylfuran from furan comprises the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction at 45 ℃ and under the pressure of +0.05MPa to obtain an esterification reaction liquid, wherein the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the catalyst is 3: 1.5:8: 0.5;
step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling to 10 ℃, then introducing into the esterification reaction kettle, and carrying out circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid at 90 ℃ by using a reboiler, after the rectification is finished, carrying out crude distillation on the reaction liquid, removing the acetic acid again at 95 ℃ and recycling the acetic acid to the furan acylation step to finally obtain a 2-acetylfuran crude product;
step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle at the temperature of 150 ℃, using the obtained 2-acetylfuran finished product in the next working section, transferring the bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and carrying out further reduced pressure distillation at the temperature of 135 ℃ to finally obtain the 2-acetylfuran finished product.
The catalyst in step S1 is a zinc salt catalyst.
Experimental part:
the yields and purities of the products 2-acetylfuran of examples 1-3 and comparative examples 1-3 were measured, and the results are shown in the following table 1:
| sample (I) | Yield of 2-acetylfuran (%) | Purity of 2-acetylfuran (%) |
| Example 1 | 98.3 | 99.7 |
| Example 2 | 98.4 | 99.9 |
| Example 3 | 97.9 | 99.6 |
| Comparative example 1 | 81.5 | 92.8 |
| Comparative example 2 | 84.8 | 90.1 |
| Comparative example 3 | 74.6 | 80.3 |
The results in the table above show that: when the reaction liquid is circulated for many times and refining operation is carried out for many times in the process, the formation of the product can be promoted, the yield of the 2-acetylfuran is improved, and the purity of the 2-acetylfuran is also improved; when the solid catalyst is used in the process, the contact area between the raw material and the catalyst can be increased on one hand, and the contact between the raw material and the catalyst can be slowly carried out on the other hand by utilizing the porous performance and the solid state of the porous silica gel, so that the generation of side reactions is reduced, and the yield and the purity of the product are improved; when the solid catalyst prepared from the organic aluminum oxy compound, the imide compound, the transition metal compound and the porous silica gel is used, the yield of the 2-acetylfuran can be effectively improved, and compared with the conventional zinc salt catalyst, the effect is greatly improved.
In the description of the present invention, it is to be understood that the terms "central," "longitudinal," "lateral," "length," "width," "thickness," "upper," "lower," "front," "rear," "left," "right," "vertical," "horizontal," "top," "bottom," "inner," "outer," "clockwise," "counterclockwise," "axial," "radial," "circumferential," and the like are used in the orientations and positional relationships indicated in the drawings for convenience in describing the invention and to simplify the description, and are not intended to indicate or imply that the referenced devices or elements must have a particular orientation, be constructed and operated in a particular orientation, and are therefore not to be considered limiting of the invention.
In the present invention, unless otherwise expressly stated or limited, the terms "disposed," "mounted," "connected," "secured," and the like are to be construed broadly and can, for example, be fixedly connected, detachably connected, or integrally formed; they may be mechanically coupled, directly coupled, or indirectly coupled through intervening agents, both internally and/or in any other manner known to those skilled in the art. The specific meanings of the above terms in the present invention can be understood by those skilled in the art according to specific situations.
The above description is only for the preferred embodiment of the present invention, but the scope of the present invention is not limited thereto, and any person skilled in the art should be considered to be within the technical scope of the present invention, and the technical solutions and the inventive concepts thereof according to the present invention should be equivalent or changed within the scope of the present invention.
Claims (8)
1. A new process for preparing 2-acetylfuran by using furan is characterized by comprising the following steps:
step S1: furan esterification
Adding acetic acid, furan, acetic anhydride and water into an esterification reaction kettle according to a certain proportion, uniformly mixing, adding a solid catalyst, and carrying out esterification reaction to obtain an esterification reaction liquid;
step S2: circulation of esterification reaction liquid
Pumping the esterification reaction liquid at the bottom of the esterification reaction kettle obtained in the step S1 into a circulating condenser, cooling by condensation, and then introducing into the esterification reaction kettle for circulating reaction;
step S3: purification of esterification reaction liquid
After the esterification reaction is finished, carrying out reduced pressure distillation on the esterification reaction liquid, separating out acetic acid, condensing the acetic acid, collecting the acetic acid, circularly rectifying the rest esterification reaction liquid by using a reboiler, after the rectification is finished, carrying out rough distillation on the reaction liquid, removing the acetic acid again, and finally obtaining a crude product of the 2-acetylfuran;
Step S4: refining of 2-acetylfuran crude product
And (4) carrying out reduced pressure distillation on the 2-acetylfuran crude product obtained in the step (S3) in a reduced pressure distillation kettle, using the obtained 2-acetylfuran finished product in the next working section, transferring the kettle bottom liquid of the reduced pressure distillation kettle into a flushing distillation kettle, and further carrying out reduced pressure distillation to finally obtain the 2-acetylfuran finished product.
2. The novel process of claim 1 for the preparation of 2-acetylfuran from furan, wherein: in the step S1, the adding mass ratio of the acetic acid, the furan, the acetic anhydride and the solid catalyst is 1-5: 1-2:5-10: 0.1-1.
3. The novel process of claim 1 for the preparation of 2-acetylfuran from furan, wherein: the esterification reaction in the step S1 is carried out at the temperature of 30-60 ℃ and the pressure of +0.05 MPa.
4. The novel process of claim 1 for the preparation of 2-acetylfuran from furan, wherein: the solid catalyst in the step S1 is 10-20% of organic aluminum oxy compound, 10-20% of imide compound, 20-30% of transition metal compound and 20-30% of porous silica gel, and the balance is water.
5. The novel process for preparing 2-acetylfuran from furan according to claim 4, wherein the preparation method of the solid catalyst comprises: dissolving an organic aluminum oxy compound, an imide compound and a transition metal compound in water in sequence, raising the temperature to 60-80 ℃, slowly adding porous silica gel, stirring for 0.5-4h, and drying to obtain the solid catalyst.
6. The novel process of claim 1 for the preparation of 2-acetylfuran from furan, wherein: the temperature for condensation and temperature reduction in the step S2 is-10-30 ℃.
7. The novel process of claim 1 for the preparation of 2-acetylfuran from furan, wherein: the temperature of the rectification in the step S3 is 85-95 ℃, the temperature of the reduced pressure distillation is 90-100 ℃, and the acetic acid obtained by the crude distillation treatment is recycled to the furan acylation step.
8. The novel process of claim 1 for the preparation of 2-acetylfuran from furan, wherein: the reduced pressure distillation temperature of the crude 2-acetylfuran product in the step S4 is 145-155 ℃, and the setting temperature of the flushing kettle is 130-140 ℃.
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