CN113999428B - Environment-friendly catalytic degradation method for high polymer material containing amide bond/ester bond - Google Patents
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Abstract
The invention discloses a green catalytic degradation method of a polymer material containing an amide bond/ester bond. According to the method, a degradation reaction system is prepared by adopting a green catalyst and a cheap and easily available conventional solvent, the high-efficiency degradation is carried out on the high-molecular material containing the amide bond or the ester bond under the mild condition, and after the reaction is finished, the degradation product and the reaction solution are easier to separate, recycle and recycle, so that the high-efficiency and low-cost recycling of the high-molecular material containing the amide bond or the ester bond can be realized, and the requirements of green low carbon and recycling economy are met.
Description
Technical Field
The invention relates to the technical field of solid waste treatment, in particular to a green catalytic degradation method of a polymer material containing amide bonds/ester bonds.
Background
The high polymer material containing the amide bond or the ester bond is a high polymer material with low price, simple synthesis process and special mechanical property, and is widely applied to various fields of rail transit, light-weight engineering, aerospace, biological medicine and the like. However, with the mass production and application of these materials, a large amount of solid waste is inevitably generated. Because these wastes have good chemical stability, it takes a long time to be completely degraded, which poses a serious threat to the surrounding environment. Meanwhile, the organic polymer materials are potential high-value secondary resources, and if the organic polymer materials are not recycled, huge waste of resources is caused. How to recycle the high-value organic solid waste in a high-efficiency green way is a problem to be solved in the current society.
The chemical recovery method is a very promising method for recovering the waste high polymer material, and hopefully realizes the closed-loop cyclic utilization of the high polymer material containing amide bonds or ester bonds. The existing chemical degradation methods mainly comprise a pyrolysis method, a hydrolysis method, an alcohol method, an alkali method, an amine method, an acid method and the like. However, most of the chemical recovery methods adopted at present are harsh in required reaction conditions, high in corrosiveness of additives or catalysts, difficult to separate by mutual dissolution of degradation products and reaction solutions, complex in degradation process operation, high in technical cost and unfavorable for industrial production. Therefore, the method for realizing the efficient green degradation of the high polymer material containing the amide bond or the ester bond is provided, and has great significance for popularization of recycling of the high polymer material.
Disclosure of Invention
The invention aims to provide a green catalytic degradation method of an amide bond/ester bond-containing polymer material, which adopts a green catalyst heteropolyacid as a degradation catalyst, is low in cost and easy to obtain, and realizes efficient catalytic degradation of the amide bond/ester bond-containing polymer material under milder conditions by using a conventional organic acid solvent and water as reaction solvents. After the reaction is finished, the degradation products and the reaction solution can be separated spontaneously or easily, and the high-efficiency recovery and recycling of the degradation products and the reaction solution can be realized.
The invention is realized by the following technical scheme:
the green catalytic degradation method of the high polymer material containing the amide bond/ester bond is characterized by comprising the following steps of: preparing a reaction solution, wherein the reaction solution is formed by adding a certain amount of heteropolyacid catalyst into a reaction solvent consisting of organic acid and water; placing the polymer material containing the amide bond or the ester bond in a reaction solution for standing treatment; heating the reaction solution added with the polymer material containing the amide bond or the ester bond to carry out degradation reaction; and separating the reaction solution from the degradation products after the reaction is completed.
The green catalytic degradation method of the polymer material containing the amide bond/ester bond is characterized in that the polymer material containing the amide bond or the ester bond is mixed with the reaction solution according to the mass ratio of 1:1-100.
The green catalytic degradation method of the high polymer material containing the amide bond/ester bond is characterized in that the mass concentration of the catalyst in the reaction solution is 0.1-50%. Preferably, the heteropolyacid catalyst comprises at least one of heteropolyacids of Keggin structure, anderson structure, waugh structure, silverton structure and Dawson structure types.
The green catalytic degradation method of the high polymer material containing the amide bond/ester bond is characterized in that the reaction solvent is a mixed solvent of organic acid and water, and the organic acid comprises monoacid, diacid, triacid and tetrabasic acid. Preferably, the mass ratio of the organic acid to the water in the mixed solvent of the organic acid and the water is 1:0-0.8.
The green catalytic degradation method of the polymer material containing the amide bond/ester bond is characterized in that the heating temperature of the degradation reaction is 40-200 ℃, and the degradation reaction time is 0.5-240h.
The green catalytic degradation method of the polymer material containing the amide bond/ester bond is characterized in that the reaction solution and the degradation product are separated after the reaction is finished, and the separation of the degradation product and the reaction solution or the separation by adopting a conventional means is included after the reaction is finished.
The green catalytic degradation method of the polymer material containing the amide bond/ester bond is characterized in that the separated reaction solution is recycled as the reaction solution after being recovered, and the separated degradation product is used as a chemical raw material.
The green catalytic degradation method of the polymer material containing the amide bond/ester bond is characterized in that the polymer material containing the amide bond or the ester bond preferably contains the main chain structureThermoplastic amide bond or ester bond containing polymeric materials of structure, wherein x= C, O, N, y= O, N.
The green catalytic degradation method of the high polymer material containing the amide bond/ester bond is characterized in that the heating mode used by the method comprises conventional heating and microwave heating.
Compared with the prior art, the invention has the following advantages:
the heteropolyacid-organic acid/water degradation reaction system adopted by the invention is environment-friendly, low in cost and easy to obtain, and the degradation reaction condition is mild. The organic acid-water coupling solvent is cooperated with the heteropolyacid to realize the rapid degradation of the high polymer material containing amide bond or ester bond, and the simple separation and recycling of degradation products and reaction solution can be realized after the reaction is finished. The method has low material energy consumption and low degradation recovery cost, and meets the requirements of green low carbon and circular economy.
Detailed Description
The following examples are given to illustrate the present invention in detail, and it is necessary to note that the following examples are given solely for the purpose of further illustration and are not to be construed as limiting the scope of the invention, as many insubstantial modifications and variations of the invention will be apparent to those skilled in the art in light of the disclosure herein. Any simple modification and equivalent variation of the following embodiments according to the technical idea of the present invention falls within the protection scope of the present invention.
Example 1
2g of silicotungstic acid was added to the reaction apparatus, 10g of formic acid and 0.5g of water were further added to prepare a reaction solution, 1g of a polyamide material was added, and the mixture was allowed to stand at room temperature for 72 hours. Then the mixture is heated to 160 ℃ from room temperature under the conventional heating condition, and the mixture is reacted for 12 hours at constant temperature. Cooling and standing after the reaction is finished, and separating to obtain degradation products and reaction solution, wherein the degradation rate of the polyamide material is 100%.
Example 2
0.1g of silicotungstic acid was added to the reaction apparatus, 99g of propionic acid and 0.9g of water were further added to prepare a reaction solution, 1g of polylactic acid material was added, and the mixture was allowed to stand at 50℃for 24 hours. Then heating from room temperature to 160 ℃ under the microwave heating condition, and reacting for 8 hours at constant temperature. After the reaction is finished, cooling and standing are carried out, and degradation products and reaction solution are obtained through separation, wherein the degradation rate of polylactic acid is 57%.
Example 3
10g of silicotungstic acid was added to the reaction apparatus, 5.56g of formic acid and 4.45g of water were further added to prepare a reaction solution, 1g of polycaprolactone material was added, and the mixture was allowed to stand at 50℃for 72 hours. Then heating from room temperature to 160 ℃ under the microwave heating condition, and reacting for 12 hours at constant temperature. After the reaction is finished, cooling and standing are carried out, and degradation products and reaction solution are obtained through separation, wherein the degradation rate of polycaprolactone is 100%.
Example 4
2g of phosphomolybdic acid was added to the reaction apparatus, 10g of oxalic acid and 0.2g of water were further added to prepare a reaction solution, 1g of polycarbonate material was added, and the reaction solution was allowed to stand at 60℃for 5 hours. Then heating from room temperature to 150 ℃ under the microwave heating condition, and reacting for 12 hours at constant temperature. After the reaction is finished, cooling and standing are carried out, and degradation products and reaction solution are obtained through separation, wherein the degradation rate of the polycarbonate is 100%.
Example 5
3g of phosphomolybdic acid was added to the reaction apparatus, 8g of formic acid and 0.5mL of water were further added to prepare a reaction solution, 11.5g of polylactic acid material was added, and the mixture was allowed to stand at 60℃for 72 hours. Then heating from room temperature to 180 ℃ under the microwave heating condition, and reacting for 36h at constant temperature. Cooling and standing after the reaction is finished, and separating to obtain degradation products and a reaction solution, wherein the degradation rate of the polylactic acid material is 36%.
Example 6
1.5g of silicotungstic acid is added into a reaction device, 10g of acetic acid, 2g of ethylene diamine tetraacetic acid and 0.5g of water are added to prepare a reaction solution, 1g of waste polyamide material is added, and the reaction solution is kept stand for 150 hours at 50 ℃. Then heating from room temperature to 140 ℃ under the microwave heating condition, and reacting for 12 hours at constant temperature. Cooling and standing after the reaction is finished, and separating to obtain degradation products and reaction solution, wherein the degradation rate of the polyamide material is 87%.
Example 7
1g of phosphomolybdic acid and 1g of phosphotungstic acid were added to the reaction apparatus, 10g of glycolic acid and 0.5g of water were further added to prepare a reaction solution, 1g of a polyamide material was added, and the mixture was allowed to stand at 60℃for 72 hours. Then heating from room temperature to 200 ℃ under the microwave heating condition, and reacting for 0.5h at constant temperature. Cooling and standing after the reaction is finished, and separating to obtain degradation products and reaction solution, wherein the degradation rate of the polyamide material is 48%.
Example 8
1.5g of silicotungstic acid was added to the reaction apparatus, 10g of propionic acid and 0.01g of water were further added to prepare a reaction solution, 1g of the polyamide carbon fiber composite material was added, and the mixture was allowed to stand at 50℃for 72 hours. Then heating from room temperature to 160 ℃ under the microwave heating condition, and reacting for 12 hours at constant temperature. Cooling and standing after the reaction is finished, separating to obtain degradation products, carbon fibers and a reaction solution, wherein the degradation rate of the polyamide material is 100%, and separating and recovering the degradation products to prepare the polyamide material.
Example 9
1g of silicotungstic acid was added to the reaction apparatus, 10g of propionic acid and 0.0001g of water were further added to prepare a reaction solution, 1g of polyurethane glass fiber composite material was added, and the mixture was allowed to stand at room temperature for 36 hours. Then heating from room temperature to 80 ℃ under the microwave heating condition, and reacting for 6 hours at constant temperature. Cooling and standing after the reaction is finished, separating to obtain degradation products, glass fibers and a reaction solution, wherein the degradation rate of the polyurethane material is 100%, and separating and recovering the degradation products to prepare the polyurethane adhesive.
Example 10
1g of silicotungstic acid was added to the reaction apparatus, 10g of propionic acid, 2g of succinic acid and 0.1g of water were further added to prepare a reaction solution, 1g of polyethylene terephthalate material was added, and the mixture was allowed to stand at 45℃for 72 hours. Then heating from room temperature to 160 ℃ under the microwave heating condition, and reacting for 12 hours at constant temperature. After the reaction is finished, cooling and standing are carried out, degradation products and reaction solution are obtained through separation, and the degradation rate of the polyethylene terephthalate is 100%.
Example 11
2g of phosphotungstic acid was added to the reaction apparatus, 8g of acetic acid, 2g of citric acid and 0.2mL of water were further added to prepare a reaction solution, 1g of polylactic acid material was added, and the reaction solution was allowed to stand at 30℃for 240 hours. Then heating from room temperature to 40 ℃ under the microwave heating condition, and reacting for 240 hours at constant temperature. Cooling and standing after the reaction is finished, and separating to obtain degradation products and a reaction solution, wherein the degradation rate of the polylactic acid material is 26%.
The foregoing description is only a preferred embodiment of the present invention, and is not intended to limit the present invention in any way, and any simple modification, equivalent variation, etc. of the above embodiment according to the technical matter of the present invention fall within the scope of the present invention.
Claims (3)
1. A green catalytic degradation method of a polymer material containing an amide bond/ester bond comprises the step of preparing a reaction solution; placing the polymer material containing the amide bond or the ester bond in a reaction solution for standing treatment; heating a reaction solution added with a polymer material containing an amide bond or an ester bond to perform degradation reaction, wherein the polymer material containing the amide bond/the ester bond is mixed with the reaction solution in a mass ratio of 1:1-100; a step of separating the reaction solution from the degradation products after the reaction is completed; the method is characterized in that:
the step of preparing the reaction solution is to add a certain amount of heteropolyacid catalyst into the reaction solvent composed of organic acid and water to form the reaction solution; the organic acid comprises any one of monobasic acid, dibasic acid, tribasic acid and tetrabasic acid; the mass ratio of the organic acid to the water in the reaction solvent is 1:0-0.8;
the polymer material containing amide bond or ester bond is contained in the main chain structureThermoplastic amide or ester bond containing polymeric materials of structure wherein x= C, O, N, y= O, N
The mass concentration of the heteropoly acid catalyst in the reaction solution is 0.1-50%;
the heteropoly acid catalyst comprises at least one of heteropoly acids of Keggin structure, anderson structure, waugh structure, silverton structure and Dawson structure type.
2. The method for green catalytic degradation of an amide bond/ester bond-containing polymer material according to claim 1, wherein the degradation reaction is carried out at a heating temperature of 40-200 ℃ and a degradation reaction time of 0.5-240h.
3. The method for green catalytic degradation of an amide bond/ester bond-containing polymer material according to claim 1, wherein the separated reaction solution is recovered and reused as a reaction solution, and the separated degradation product is used as a chemical raw material.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2409837A1 (en) * | 2000-06-08 | 2001-12-13 | Dupont Canada Inc. | Solvent-based recovery and recycle of polyamide material |
| CN107365429A (en) * | 2017-08-31 | 2017-11-21 | 江苏中信世纪新材料有限公司 | The application of heteropoly acid and lewis acid in thermosetting resin of degrading as catalyst |
| CN108093634A (en) * | 2015-07-09 | 2018-05-29 | 循环产业公司 | The depolymerization of polyethylene terephthalate |
| CN110157038A (en) * | 2019-04-11 | 2019-08-23 | 四川大学 | A method of the low temperature fast degradation of the macromolecule resin containing ester bond and separation |
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| CN108993134B (en) * | 2018-07-16 | 2021-05-25 | 天津大学 | Method for degrading ester VOCs (volatile organic compounds) by using low-temperature microwave-enhanced cerium oxide-loaded palladium monatomic catalyst |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2409837A1 (en) * | 2000-06-08 | 2001-12-13 | Dupont Canada Inc. | Solvent-based recovery and recycle of polyamide material |
| CN108093634A (en) * | 2015-07-09 | 2018-05-29 | 循环产业公司 | The depolymerization of polyethylene terephthalate |
| CN107365429A (en) * | 2017-08-31 | 2017-11-21 | 江苏中信世纪新材料有限公司 | The application of heteropoly acid and lewis acid in thermosetting resin of degrading as catalyst |
| CN110157038A (en) * | 2019-04-11 | 2019-08-23 | 四川大学 | A method of the low temperature fast degradation of the macromolecule resin containing ester bond and separation |
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