CN112898250B - Preparation method of 2, 5-furandicarboxylic acid - Google Patents
Preparation method of 2, 5-furandicarboxylic acid Download PDFInfo
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Abstract
The application discloses a preparation method of 2, 5-furandicarboxylic acid, belonging to the technical field of organic chemistry. The method comprises the steps of introducing reaction gas into a reaction system, maintaining the reaction system under a certain pressure, and oxidizing raw materials in the reaction system at a certain temperature to generate the 2, 5-furandicarboxylic acid, wherein the raw materials are 5-hydroxymethylfurfural or 5-hydroxymethylfurfural derivatives, the reaction gas contains carbon dioxide and oxygen in a molar ratio of 1-10, and a solvent in the reaction system is organic acid and halogen and a metal catalyst exist. The method effectively inhibits the combustion of the substrate in the oxidation process by controlling the proportion of carbon dioxide and oxygen in the reaction gas, improves the safety of the reaction, and simultaneously improves the selectivity and the yield of the FDCA (which can reach more than 93 percent).
Description
Technical Field
The application relates to the technical field of organic chemistry, in particular to a preparation method of 2, 5-furandicarboxylic acid.
Background
2, 5-Furanedicarboxylic acid (FDCA) is an important furan derivative, is determined by the U.S. department of energy as one of 12 compounds for establishing a future 'green' chemical industry platform, can be directly used for synthesizing high-performance materials such as polyester, polyurethane and the like due to the similarity of the structure of the FDCA and terephthalic acid, and the polyester synthesized by FDCA is better than PET in barrier property and thermal stability, and meanwhile, FDCA can be applied to the fields of medicines, pesticides and the like, so that the FDCA has a higher market prospect. However, since the first report in 1876, no specific commercially viable method for preparing the product has been available.
The synthesis route of FDCA mainly comprises a 5-Hydroxymethylfurfural (HMF) oxidation route, a hexose diacid dehydration route, a furfural/furoic acid route and a diglycolic acid route, wherein the HMF oxidation route is the most expected method for realizing industrialization. The method for preparing FDCA by oxidizing HMF mainly comprises noble metal catalytic oxidation, metering oxidation and a metal catalyst co-catalytic oxidation method of bromine in organic acid. Wherein, a large amount of waste salt is generated in the preparation process of the noble metal oxidation method, and the cost of the catalyst is higher. The metering oxidation method only needs potassium permanganate oxidation, nitric acid oxidation and peroxide oxidation, so that the equipment is seriously corroded in the preparation process, and a large amount of waste liquid and waste salt are generated. The production process of the organic acid bromine and metal catalyst co-catalytic oxidation method has no waste salt, the organic acid can be recycled, and the catalyst can be recycled, so that the method is an environment-friendly preparation method, and therefore, the method for preparing FDCA by using the organic acid bromine and metal catalyst co-catalytic oxidation method is the most promising way for realizing industrialization.
In US 8791277 B2, HMF is used as a substrate, FDCA is prepared by catalytic oxidation under the conditions of 0-15% of water content and 100-200 ℃, the method improves the yield of FDCA by high Co/Mn (10-400) and Co/Br (0.7-3.5) molar ratio, the yield reaches over 90%, but the combustion of raw materials and solvents is aggravated by the increase of Co, the heating speed is high, and the safety coefficient is low.
US 8865921 B2 oxidizes HMF into FDCA in a Co/Mn/Br acetic acid catalytic system at the temperature higher than 140 ℃, wherein the molar ratio of the catalyst is that Co/Mn is 1/100-10/1; br/(Co + Mn) is 0.001-2; the addition amount of (Co + Mn) is 0.1-10% of the molar amount of the raw materials, in this case the yield of FDCA is 70-80%, and the yield is low.
CN 107848997A is added with Zr and Ce under the condition of catalyst of 59-5900 ppm Co, 55-5500 ppm Mn and 203-20000 ppm Br based on the concentration of substrate to catalyze HMF and the ester oxidation thereof to prepare FDCA, the yield reaches about 80 percent, and the yield is lower.
US 9321744 B1 takes Co/Mn/Br as a main catalyst, adds Zr, ce, cu, ni, zn and Hf as cocatalyst, wherein the addition amount of the catalyst is 0.05-8 wt% of the reaction system, catalyzes HMF and derivatives thereof to prepare FDCA at 100-250 ℃ and 8-60 bar pressure, and the yield of the FDCA can reach about 75%, and is low.
Disclosure of Invention
According to one aspect of the application, a 2, 5-furandicarboxylic acid preparation method is provided, wherein a reaction gas is continuously introduced into a reactor, a mixture in the reactor is subjected to a catalytic oxidation reaction, and 2, 5-furandicarboxylic acid is generated, wherein the mixture comprises a raw material, an organic acid, a halogen and a metal catalyst, the raw material is 5-hydroxymethylfurfural or a 5-hydroxymethylfurfural derivative, and the reaction gas comprises carbon dioxide and oxygen in a molar ratio of 1-10; the method effectively inhibits the combustion of the substrate in the oxidation process by controlling the proportion of carbon dioxide and oxygen in the reaction gas, improves the safety of the reaction, and simultaneously improves the selectivity and the yield of the FDCA (up to more than 93 percent).
Optionally, the catalytic oxidation reaction temperature is 200-250 ℃, and the reaction pressure is 1-10 MPa.
Optionally, the catalytic oxidation reaction temperature is 220-250 ℃, the reaction pressure is 1-5 MPa, and the reaction pressure is more preferably 3-4 MPa.
Alternatively, the molar ratio of carbon dioxide to oxygen in the reaction gas is preferably 1 to 5.
Optionally, the metal catalyst comprises at least a compound of one of the following metal elements: cobalt, manganese, iron, zirconium, cerium, selenium, copper, vanadium, ruthenium or nickel; wherein, the valence of the metal ion in the compound is not limited, and the anion in the compound comprises but not limited to carbonate, acetate, tetrahydrate acetate or halide.
Optionally, the halogen comprises chlorine, bromine, fluorine or iodine; the halogen is preferably added to the mixture in the form of hydrogen halide, sodium halide, ammonium halide or potassium halide.
Optionally, the mass of the metal element in the metal catalyst is 0.01 to 3% of the mass of the raw material.
Optionally, the metal catalyst at least comprises cobalt and/or cerium, when cobalt or cerium is included, the cobalt or cerium accounts for 10-100% of the total mass of the metal elements in the metal catalyst, and when cobalt and cerium are included, the cobalt and cerium accounts for 10-100% of the total mass of the metal elements in the metal catalyst;
in one embodiment, the metal catalyst is formed by mixing a cobalt compound and a compound of at least one of the following metal elements: manganese, iron, zirconium, selenium, copper, vanadium, ruthenium or nickel, wherein the cobalt element accounts for 25-30% of the total mass of all metal elements in the metal catalyst; in another embodiment, the metal catalyst is formed by mixing a cerium compound and a compound of at least one of the following metal elements: cobalt, manganese, iron, zirconium, selenium, copper, vanadium, ruthenium or nickel, wherein cerium accounts for 55-95% of the total mass of all metal elements in the metal catalyst;
alternatively, the molar ratio of the metal element to the halogen in the metal catalyst is 0.1 to 10, preferably 0.5 to 3.
Alternatively, the organic acid is a monocarboxylic acid, including but not limited to an aliphatic monocarboxylic acid such as acetic acid, propionic acid, butyric acid, or valeric acid, preferably acetic acid.
Alternatively, the 5-hydroxymethylfurfural derivative is a 5-hydroxymethylfurfural ether derivative and/or a 5-hydroxymethylfurfural ester derivative, and specifically includes, but is not limited to, 5- (alkoxymethyl) furfural (AMF), 5- (aryloxymethyl) furfural, 5- (cycloalkoxymethyl) furfural, 5- (alkoxycarbonyl) furfural or 5-acetoxymethyl-2-furfural.
Optionally, the amount of the raw materials added is 10 to 50%, preferably 15 to 35% of the total mass of the mixture.
Optionally, the mixture further comprises water, and the mass of the water is 10-25%, preferably 12-20% of the total mass of the mixture.
Alternatively, the reaction gas may be formed by mixing carbon dioxide and oxygen, carbon dioxide and oxygen-enriched air, or carbon dioxide and air.
In a specific embodiment, the preparation method comprises the following steps:
mixing organic acid, halogen and metal catalyst in proportion, and adding the mixture into a reactor;
and introducing reaction gas into the reactor until the reaction pressure is reached, heating to the reaction temperature, adding raw materials into the reactor, and continuously introducing the reaction gas to enable the mixture in the reactor to generate catalytic oxidation reaction. The method can avoid deterioration of raw materials, and further improve yield.
The beneficial effects that this application can produce include:
(1) The application provides a preparation method of 2, 5-furandicarboxylic acid, which is characterized in that the proportion of carbon dioxide and oxygen in reaction gas is controlled, so that a higher carbon dioxide partial pressure is formed in a reactor, the carbon dioxide is used as a main product of a combustion reaction, and the occurrence of a phenomenon of raw material and/or solvent combustion in an oxidation process can be effectively inhibited due to the large amount of carbon dioxide, the phenomenon of too high temperature rise caused by combustion is avoided, and the safety of the reaction is improved; due to the addition of the carbon dioxide, the conversion of the metal catalyst from a low valence state to a high valence state is promoted, the oxidation of HMF to an intermediate product and FDCA is accelerated, the added HMF basically does not stay in the solution in the form of HMF, the self-polymerization of the HMF is prevented, and the selectivity and the yield of the FDCA are improved (more than 93 percent and up to 97.8 percent).
(2) On the basis, the reaction temperature is increased, so that the reaction time can be greatly shortened, the using amount of the catalyst is reduced, the production cost is reduced, and in addition, the substrate concentration is increased due to the increase of the reaction temperature, so that the method is more beneficial to industrial production.
Detailed Description
The present application will be described in detail with reference to examples, but the present application is not limited to these examples.
The raw materials in the examples of the present application were all purchased commercially, unless otherwise specified.
Wherein the HMF was purchased from Wutong perfumery, tenn.
The yields of 2,5-furandicarboxylic acid in the examples and comparative examples of the present application were calculated by the formula (molar amount of 2,5-furandicarboxylic acid)/(molar amount of 5-hydroxymethylfurfural added). Times.100%.
After the reaction of each example and comparative example was completed, quantitative measurement of FDCA was performed in the solid and liquid phases using HPLC, and the total yield of FDCA was calculated using the sum of the two.
Example 1:
weighing 500g of acetic acid, 0.1g of cobalt acetate tetrahydrate, 0.06g of manganese acetate tetrahydrate, 0.3g of hydrogen bromide and 0.1g of cerium acetate tetrahydrate in a 1L oxidation reaction kettle by adopting CO 2 Mixing with air to obtain CO 2 Introducing gas with the molar ratio of oxygen to 1 into a reaction kettle, wherein the reaction pressure is 3MPa, heating to 200 ℃, and pumping HMF (75 g) dissolved in 65g of water by a high-pressure pumpAnd (3) putting the mixture into a reaction kettle, continuously introducing the gas with the proportion for carrying out oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, quantifying the FDCA content in the solid and the solution by using HPLC respectively, and calculating to obtain the total yield of the FDCA of 93.3%.
Example 2:
500g of acetic acid, 2.0g of cobalt acetate tetrahydrate, 2.3g of manganese acetate tetrahydrate, 3.0g of hydrogen bromide and 1.0g of zirconium acetate are weighed into a 1L oxidation reaction kettle by adopting CO 2 Mixing with air to obtain CO 2 And introducing gas with the molar ratio of oxygen to oxygen being 3.
Example 3:
weighing 500g of acetic acid, 2.0g of cobalt acetate tetrahydrate, 4.5g of manganese acetate tetrahydrate, 3.0g of hydrogen bromide and 3.0g of cerium acetate tetrahydrate in a 1L oxidation reaction kettle by adopting CO 2 Mixing with air to obtain CO 2 And introducing gas with the molar ratio of oxygen to oxygen being 5 into a reaction kettle, heating to 250 ℃ under the reaction pressure of 4MPa, pumping HMF (150 g) dissolved in 150g of water into the reaction kettle by using a high-pressure pump, continuously introducing the gas with the ratio for carrying out oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, quantifying the FDCA content in the solid and the solution by using HPLC respectively, and calculating to obtain the total FDCA yield of 97.2%.
Example 4:
500g of acetic acid, 1.0g of cobalt acetate tetrahydrate, 7.5g of cerium acetate tetrahydrate and 1.0g of hydrogen bromide are weighed into a 1L oxidation reaction kettle by adopting CO 2 Mixing with oxygen to obtain CO 2 Introducing gas with the molar ratio of oxygen to 5 into a reaction kettle, heating to 250 ℃ under the reaction pressure of 4MPa, pumping HMF (200 g) dissolved in 200g of water into the reaction kettle by using a high-pressure pump, continuously introducing the gas with the ratio for carrying out oxidation reaction for 0.5h, and cooling to room temperature after the reaction is finishedThe product was obtained by filtration, and the FDCA content in the solid and solution were quantified using HPLC, respectively, and the total yield of FDCA was calculated to be 96.5%.
Example 5:
500g of acetic acid, 2.0g of cobalt acetate tetrahydrate and 1.0g of hydrogen bromide are weighed into a 1L oxidation reaction kettle by adopting CO 2 Mixing with air to obtain CO 2 Introducing gas with the molar ratio of oxygen to 5 into a reaction kettle, heating to 220 ℃ under the reaction pressure of 3MPa, pumping HMF (100 g) dissolved in 200g of water into the reaction kettle by using a high-pressure pump, continuously introducing the gas with the ratio for carrying out oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, quantifying the FDCA content in the solid and the solution by using HPLC respectively, and calculating to obtain the total yield of the FDCA of 94.5%.
Example 6:
500g of acetic acid, 2.3g of cobalt acetate tetrahydrate, 1.5g of zirconium acetate tetrahydrate and 1.0g of hydrogen bromide were weighed into a 1L oxidation reaction kettle by using CO 2 Mixing with air to obtain CO 2 Introducing gas with the molar ratio of oxygen to 5 into a reaction kettle, heating to 220 ℃ under the reaction pressure of 3MPa, pumping HMF (100 g) dissolved in 200g of water into the reaction kettle by using a high-pressure pump, continuously introducing the gas with the ratio for carrying out oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, quantifying the FDCA content in the solid and the solution by using HPLC respectively, and calculating to obtain the total yield of the FDCA of 95.8%.
Example 7:
weighing 500g of acetic acid, 1.0g of cobalt acetate tetrahydrate, 1.0g of zirconium acetate tetrahydrate, 1.0g of cerium acetate tetrahydrate and 1.0g of hydrogen bromide in a 1L oxidation reaction kettle by adopting CO 2 Mixing with air to obtain CO 2 Introducing gas with the molar ratio of oxygen to 5 into a reaction kettle, heating to 220 ℃ under the reaction pressure of 3MPa, pumping HMF (100 g) dissolved in 200g of water into the reaction kettle by using a high-pressure pump, continuously introducing the gas with the ratio for carrying out oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, quantifying the FDCA content in the solid and the solution by using HPLC respectively, and calculating to obtain the total yield of the FDCA of 96.8%.
Example 8
400g of acetic acid, 1.0g of cobalt acetate tetrahydrate, 1.0g of zirconium acetate tetrahydrate, 1.0g of cerium acetate tetrahydrate, 200g of water and 1.0g of hydrogen bromide are weighed into a 1L oxidation reaction kettle by adopting CO 2 Mixing with air to obtain CO 2 Introducing gas with the molar ratio of oxygen to oxygen being 5 into a reaction kettle, heating to 220 ℃ under the reaction pressure being 3MPa, pumping 5-acetoxyl methyl-2-furfural AcHMF (100 g) dissolved in 100g of acetic acid into the reaction kettle by a high-pressure pump, continuously introducing the reaction gas with the ratio for oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, and calculating to obtain the FDCA yield of 97.3%.
Example 9
Weighing 500g of acetic acid, 2.0g of cobalt acetate tetrahydrate, 4.5g of manganese acetate tetrahydrate, 3.0g of hydrogen bromide and 3.0g of cerium acetate tetrahydrate in a 1L oxidation reaction kettle, mixing carbon dioxide gas and air to obtain reaction gas with the molar ratio of carbon dioxide to oxygen being 10, introducing the reaction gas into the reaction kettle, heating the reaction pressure to be 4MPa, pumping HMF (150 g) dissolved in 150g of water into the reaction kettle by using a high-pressure pump, continuously introducing the reaction gas with the ratio to perform oxidation reaction for 0.5h, cooling to room temperature after the reaction is finished, filtering to obtain a product, and calculating to obtain the yield of FDCA to be 94.6%.
Comparative example 1
The preparation method is basically the same as that of example 2, the only difference is that the reaction gas is air, the yield of the obtained FDCA is 85.3 percent by calculation, the obtained FDCA product has poor quality, the color of the product is dark brown, and the product is mainly caused by polymerization of HMF at high temperature.
Comparative example 2
The preparation method was substantially the same as in example 2 except that the reaction temperature was 130 deg.C and the reaction time was 1.5 hours, and the yield of FDCA was calculated to be 67.8%.
Comparative example 3
The preparation method was substantially the same as in example 2, except that the reaction gas was air, the reaction temperature was 180 ℃ and the reaction time was 1 hour, and the yield of FDCA was calculated to be 75.6%.
Although the present invention has been described with reference to a few preferred embodiments, it should be understood that various changes and modifications can be made without departing from the spirit and scope of the invention as defined by the appended claims.
Claims (15)
1. A method for preparing 2, 5-furandicarboxylic acid, comprising:
continuously introducing reaction gas into the reactor to enable the mixture in the reactor to perform catalytic oxidation reaction to generate 2, 5-furandicarboxylic acid;
wherein the mixture comprises a feedstock, an organic acid, a halogen, and a metal catalyst;
the raw material is 5-hydroxymethyl furfural;
the reaction gas contains carbon dioxide and oxygen, or carbon dioxide and air,
the molar ratio of carbon dioxide to oxygen or carbon dioxide to air is 1 to 10;
the temperature of the catalytic oxidation reaction is 220 to 240 ℃;
the metal catalyst comprises at least one compound of the following metal elements:
cobalt, manganese, zirconium, cerium.
2. The method according to claim 1, wherein the pressure of the catalytic oxidation reaction is 1 to 10MPa.
3. The process according to claim 1, wherein the pressure of the catalytic oxidation reaction is from 1 to 5 MPa.
4. The production method according to claim 1, wherein the molar ratio of carbon dioxide to oxygen in the reaction gas is 1 to 5.
5. The production method according to claim 1,
the mass of the metal element in the metal catalyst is 0.01-3% of the mass of the raw material.
6. The preparation method according to claim 5, wherein the metal catalyst comprises at least cobalt and/or cerium, and when the metal catalyst comprises cobalt or cerium, the cobalt or cerium accounts for 10 to 100% of the total mass of the metal elements in the metal catalyst, and when the metal catalyst comprises cobalt and cerium, the sum of the cobalt and cerium accounts for 10 to 100% of the total mass of the metal elements in the metal catalyst.
7. The method of claim 1, wherein the halogen comprises chlorine, bromine, fluorine, or iodine; the halogen is present in the mixture in the form of hydrogen halide, sodium halide, ammonium halide or potassium halide.
8. The production method according to claim 1, wherein a molar ratio of the metal element in the metal catalyst to the halogen is from 0.1 to 10.
9. The production method according to claim 1, wherein a molar ratio of the metal element in the metal catalyst to the halogen is 0.5 to 3.
10. The production method according to claim 1, wherein the organic acid is a monocarboxylic acid; the organic acid is acetic acid, propionic acid, butyric acid or valeric acid.
11. The method according to claim 1, wherein the raw material is added in an amount of 10 to 50% by mass based on the total mass of the mixture.
12. The preparation method according to claim 1, wherein the addition amount of the raw materials is 15 to 35% of the total mass of the mixture.
13. The preparation method according to claim 1, wherein the mixture further comprises water, and the mass of the water is 10 to 25% of the total mass of the mixture.
14. The method according to claim 13, wherein the mass of water is 12 to 20% of the total mass of the mixture.
15. The method according to claim 1, wherein the step of introducing the reaction gas into the reactor to perform a catalytic oxidation reaction on the mixture in the reactor comprises:
mixing organic acid, halogen and metal catalyst in proportion, and adding into a reactor;
and introducing reaction gas into the reactor until the reaction pressure is reached, heating to the reaction temperature, adding the raw material into the reactor, and continuously introducing the reaction gas to enable the mixture in the reactor to generate catalytic oxidation reaction.
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| Title |
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| "Kinetics of Homogeneous 5-Hydroxymethylfurfural Oxidation to 2,5-Furandicarboxylic Acid with Co/Mn/Br Catalyst";Xiaobin Zuo et al.;《AIChE Journal》;20170131;第63卷;第162-171页 * |
| Xiaobin Zuo et al.."Kinetics of Homogeneous 5-Hydroxymethylfurfural Oxidation to 2,5-Furandicarboxylic Acid with Co/Mn/Br Catalyst".《AIChE Journal》.2017,第63卷第162-171页. * |
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