CN115770617B - Solution catalyst for recycling polyethylene glycol terephthalate and preparation method thereof - Google Patents
Solution catalyst for recycling polyethylene glycol terephthalate and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a solution type catalyst for recycling polyethylene glycol terephthalate and a preparation method thereof. The solution catalyst is a uniform and stable solution formed by the reaction of metal oxide and methanesulfonic acid in glycol; the preparation method comprises the steps of mixing and stirring metal oxide and methanesulfonic acid uniformly at normal temperature to obtain white turbid liquid, adding ethylene glycol into the turbid liquid under standard atmospheric pressure, and heating and stirring until a uniform and stable solution is obtained to obtain the solution-type catalyst. The preparation method of the invention is simple and convenient, has low cost, and the obtained catalyst has high yield and low price, and has wide application prospect in the field of high-efficiency recovery of polyethylene terephthalate.
Description
Technical Field
The invention relates to a catalyst and a preparation method and application thereof, in particular to a preparation method and application of a solution-type catalyst for recycling polyethylene terephthalate.
Background
Polyethylene terephthalate has been widely used in various fields due to its excellent mechanical properties and chemical resistance. The yield of polyester material increases dramatically, which causes recycling problems for polyester products. The problem that a large amount of waste polyester is accumulated in the nature and cannot be degraded restricts the development of economy, influences the ecological environment, and how to effectively degrade and recycle the polyester material is a urgent need to solve the problem.
The processes that have been applied to degradation recovery of PET plastics today are largely divided into physical recovery and chemical recovery. Physical recovery mainly comprises mechanical recovery and heat recovery, and the method has irreversible performance loss on the recovered PET, so that the quality of the obtained secondary PET product is reduced linearly. The chemical recovery method is mainly realized by four ways, namely hydrolysis, alcoholysis, glycol alcoholysis and aminolysis, and the four methods are different from each other, and aim to add a reaction solvent to convert PET into corresponding monomers by a chemical reaction method. The monomer is polymerized into PET products again to realize the aim of upgrading circulation.
In the chemical recovery method, glycol alcoholysis is attracting attention of many scientific researchers due to its mild and rapid reaction conditions, wherein ethylene glycol is mostly used as a reactive solvent, and efficient degradation of PET (polyethylene terephthalate) into a dihydroxyethyl terephthalate (BHET) monomer is realized under the condition of normal pressure and lower temperature. And in the continuous research in recent years, the continuous production process is gradually realized, so that the degradation of PET becomes more efficient. However, the glycol alcoholysis process has a biggest problem in that the reactivity is low, and thus, it is generally necessary to add a catalyst during the reaction, and the reactivity is improved by changing the activation energy required for the reaction. Therefore, the development of green high activity catalysts becomes a key to sustainable PET recovery.
Disclosure of Invention
In order to overcome the problems in the background art, the invention provides a solution type catalyst applied to polyethylene terephthalate recovery and a preparation method thereof.
In order to achieve the above purpose, the technical scheme adopted by the invention for solving the technical problems is as follows:
1. A solution catalyst for recovering polyethylene terephthalate:
The solution catalyst is a uniform and stable solution mainly formed by the reaction of metal oxide and methanesulfonic acid in ethylene glycol.
The metal oxide is one of zinc oxide, calcium oxide, magnesium oxide, sodium oxide and potassium oxide, preferably zinc oxide.
The metal oxide: methanesulfonic acid: the mol ratio of the glycol is 1:0:4-0:1:4.
2. A method for preparing a solution catalyst for recycling polyethylene terephthalate, comprising the following steps:
step 1) mixing metal oxide and methanesulfonic acid at normal temperature, and uniformly stirring to obtain viscous white turbid liquid;
and 2) adding ethylene glycol into the thick white turbid liquid obtained in the step 1) under standard atmospheric pressure, heating and stirring to obtain a uniform and stable solution, and obtaining the solution catalyst applied to recycling polyethylene terephthalate.
In the step 2), the heating temperature is 80 ℃ and the heating time is 1h.
3. The solution catalyst is applied to the recovery method of polyethylene glycol terephthalate:
The catalyst is added into a solution where polyethylene terephthalate is located, and the polyethylene terephthalate depolymerizes to obtain insoluble substances such as a dihydroxyethyl terephthalate (BHET) monomer, a dimer, other oligomers and the like.
The mass amount of the catalyst is 1-10% of the mass of the polyethylene terephthalate, and is preferably 5%.
The catalyst is added with glycol solvent in the depolymerization reaction, and the dosage of the glycol solvent is 4-6 times of the mass of the polyethylene terephthalate.
The reaction condition of the depolymerization reaction is standard atmospheric pressure, the reaction temperature is 185-195 ℃, and the reaction time is 2-3 h.
The preparation method of the invention is simple and convenient, has low cost, and the obtained catalyst has high yield and low price, and has wide application prospect in the field of high-efficiency recovery of polyethylene terephthalate.
Compared with the background technology, the invention has the beneficial effects that:
According to the invention, the metal oxide is mixed with the methane sulfonic acid, and the solution catalyst prepared by taking ethylene glycol as a solvent is used for catalyzing and degrading PET, so that the BHET monomer is obtained, and compared with the catalyst prepared by taking single oxide or methane sulfonic acid as the catalyst, the catalyst after the mixed reaction has obvious improvement on the depolymerization efficiency and the monomer yield. Under the best experimental conditions, the most effective oxide for the experiment is zinc oxide. The monomer yields for zinc oxide or methanesulfonic acid alone were 45% and 35.2%, respectively, whereas the best efficiency for the use of the solution catalyst was 86.9%.
Compared with other expensive and complex catalysts, the invention realizes the high-efficiency depolymerization of PET and the high yield of monomer on the basis of economy and simple preparation, and is more beneficial to the progress of PET depolymerization to industrial production.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
Embodiments of the invention are as follows:
example 1:
adding 4.05g of zinc oxide and 12.4g of ethylene glycol into a three-neck flask, uniformly stirring, heating at normal pressure and 80 ℃ and mechanically stirring for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution type catalyst A. The specific molar ratios are shown in Table 1.
Example 2
Adding 4.05g of zinc oxide and 4.8g of methanesulfonic acid into a three-neck flask, stirring uniformly in advance, adding 9.3g of ethylene glycol, heating at normal pressure and 80 ℃ and stirring mechanically for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution catalyst B. The specific molar ratios are shown in Table 1.
Example 3
Adding 4.05g of zinc oxide and 7.2g of methanesulfonic acid into a three-neck flask, stirring uniformly in advance, adding 7.75g of ethylene glycol, heating at normal pressure and 80 ℃ and stirring mechanically for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution catalyst C. The specific molar ratios are shown in Table 1. This example is later demonstrated as the preferred embodiment.
Example 4
Adding 4.05g of zinc oxide and 9.6g of methanesulfonic acid into a three-neck flask, stirring uniformly in advance, adding 6.2g of ethylene glycol, heating at normal pressure and 80 ℃ and stirring mechanically for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution catalyst D. The specific molar ratios are shown in Table 1.
Example 5
Adding 4.8g of methanesulfonic acid and 12.4g of ethylene glycol into a three-neck flask, uniformly stirring, heating at normal pressure and 80 ℃ and mechanically stirring for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution catalyst E. The specific molar ratios are shown in Table 1.
Example 6
Adding 2.8g of calcium oxide and 7.2g of methanesulfonic acid into a three-neck flask, stirring uniformly in advance, adding 7.75g of ethylene glycol, heating at normal pressure and 80 ℃ and stirring mechanically for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution catalyst F. The specific molar ratios are shown in Table 1.
Example 7
2.0G of magnesium oxide and 7.2G of methanesulfonic acid are added into a single-neck flask, uniformly stirred in advance, then 7.75G of ethylene glycol is added, the mixture is heated at the normal pressure of 80 ℃ and mechanically stirred for 1h, after the reaction time is over, the mixed solution in the flask is taken out by a rubber head dropper, and the mixed solution is stored in a transparent sample bottle, so that the solution type catalyst G is obtained. The specific molar ratios are shown in Table 1.
Example 8
3.1G of sodium oxide and 7.2g of methanesulfonic acid are added into a three-neck flask, uniformly stirred in advance, then 7.75g of ethylene glycol is added, the mixture is heated at the normal pressure of 80 ℃ and mechanically stirred for 1H, after the reaction time is over, the mixed solution in the flask is taken out by a rubber head dropper, and the mixed solution is stored in a transparent sample bottle, so that the solution type catalyst H is obtained. The specific molar ratios are shown in Table 1.
Example 9
Adding 4.7g of potassium oxide and 7.2g of methanesulfonic acid into a three-neck flask, stirring uniformly in advance, adding 7.75g of ethylene glycol, heating at normal pressure and 80 ℃ and stirring mechanically for 1h, taking out the mixed solution in the flask by using a rubber head dropper after the reaction time is over, and storing in a transparent sample bottle to obtain the solution catalyst I. The specific molar ratios are shown in Table 1.
Example 10
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 1) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 84.0%, and the yield of BHET monomer was 52.5%.
Example 11
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 2) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 92.0%, and the yield of BHET monomer was 73.3%.
Example 12
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 3) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 100.0%, and the yield of BHET monomer was 86.9%. This example was subsequently demonstrated as the optimal depolymerized PET condition.
Example 13
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 4) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 75.0%, and the yield of BHET monomer was 60.3%.
Example 14
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 5) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 65.0%, and the yield of BHET monomer was 41.2%.
Comparative example 1
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 6) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 70.0%, and the yield of BHET monomer was 53.3%.
Comparative example 2
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 7) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 77.0%, and the yield of BHET monomer was 61.8%.
Comparative example 3
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 8) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 75.0%, and the yield of BHET monomer was 61.4%.
Comparative example 4
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 9) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 86.0%, and the yield of BHET monomer was 71.8%.
Comparative example 5
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 3) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 185℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 74.0%, and the yield of BHET monomer was 56.4%.
Comparative example 6
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 3) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at a temperature of 195℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 100.0%, and the yield of BHET monomer was 83.9%.
Comparative example 7
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 3) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 86.0%, and the yield of BHET monomer was 70.2%.
Comparative example 8
10GPET pieces of ethylene glycol (50 g) and 0.5g of catalyst (prepared in example 4) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 3 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 100.0%, and the yield of BHET monomer was 85.5%.
Comparative example 9
10GPET pieces of ethylene glycol (40 g) and 0.5g of catalyst (prepared in example 4) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 100%, and the yield of BHET monomer was 71.8%.
Comparative example 10
10GPET pieces of ethylene glycol (60 g) and 0.5g of catalyst (prepared in example 4) were sequentially added to a three-necked flask, the round-bottomed flask was stirred with a mechanical stirrer, and heated by heating with a heating mantle equipped with a temperature sensor at 190℃under a pressure of 1atm for 2.5 hours under reflux by condensation. And after the reaction is finished, cooling to normal temperature, adding excessive deionized water for dissolution, and then carrying out suction filtration to obtain unreacted PET for drying and bearing. The filtrate was concentrated to 100ml in a rotary evaporator and cooled at 0℃for 12h to give white needle-like crystals. Under this condition, the PET depolymerization rate was 100%, and the yield of BHET monomer was 82.4%.
TABLE 1 depolymerization effects of catalysts in different ratios
TABLE 2 depolymerization Effect of different Oxidation catalysts
As can be seen from the data in table 1, the catalyst prepared in example 3 has the best depolymerization effect. It is also seen from the table that the more the molar ratio of acid, the more detrimental it is to the depolymerization reaction.
As can be seen from the data in table 2, zinc oxide has the best performance with catalysts composed of methanesulfonic acid, ethylene glycol, and therefore zinc oxide is preferred for the catalyst application reaction.
The specific implementation also carries out reaction condition optimization experiments:
Temperature optimization
TABLE 3 Table 3
Time optimization
TABLE 4 Table 4
Solvent optimization
TABLE 5
The results of the comparative experiments in tables 3, 4 and 5 are combined. The best reaction conditions obtained in the experiment are that the mass ratio of PET to glycol is 1:5, the catalyst amount is 5% of the total mass of PET, the reaction temperature is 190 ℃, the pressure is 1atm, the reaction time is 2.5h, the recovery efficiency of PET is 100%, and the yield of BHET monomer reaches 86.9%. Therefore, it can be concluded that the prepared catalyst has a better effect of catalyzing depolymerization of PET.
The above-described embodiments are only intended to illustrate the present invention, not to limit the scope of the present invention. It should be noted that any equivalent changes or modifications made within the spirit of the invention and the scope of the claims are considered to be within the scope of the invention without departing from the principles of the invention.
Claims (7)
1. A solution catalyst for recovering polyethylene terephthalate, characterized in that: the solution type catalyst is a uniform and stable solution mainly formed by the reaction of metal oxide and methanesulfonic acid in ethylene glycol;
the metal oxide is one of zinc oxide, calcium oxide, magnesium oxide, sodium oxide and potassium oxide;
The metal oxide: methanesulfonic acid: the molar ratio of the ethylene glycol is 1:1: 3-1: 2:2.
2. A process for preparing a solution catalyst for recovering polyethylene terephthalate as claimed in claim 1, comprising the steps of:
Step 1) mixing metal oxide and methanesulfonic acid at normal temperature, and uniformly stirring to obtain viscous white turbid liquid;
And 2) adding ethylene glycol into the viscous white turbid liquid obtained in the step 1) under standard atmospheric pressure, heating and stirring to obtain a uniform and stable solution, and obtaining the solution catalyst.
3. The method for preparing the solution catalyst for recycling polyethylene terephthalate according to claim 2, wherein the method comprises the following steps: in the step 2), the heating temperature is 80 ℃ and the heating time is 1h.
4. The use of the solution catalyst of claim 1 or the solution catalyst prepared by the preparation method of any one of claims 2 to 3, characterized in that: the recycling application of the polyethylene terephthalate.
5. A method for recycling polyethylene terephthalate by using the solution catalyst according to claim 1 or the solution catalyst prepared by the preparation method according to any one of claims 2 to 3, characterized in that: the catalyst is added into a solution where polyethylene terephthalate is located, and the polyethylene terephthalate depolymerizes to obtain the main products of the dihydroxyethyl terephthalate monomer, the dimer and other oligomer insoluble matters.
6. The method for recovering polyethylene terephthalate according to claim 5, wherein the step of recovering the polyethylene terephthalate comprises the steps of: the mass dosage of the catalyst is 1-10% of the mass of the polyethylene terephthalate.
7. The method for recovering polyethylene terephthalate according to claim 5, wherein the step of recovering the polyethylene terephthalate comprises the steps of: the reaction condition of the depolymerization reaction is standard atmospheric pressure, the reaction temperature is 185-195 ℃, and the reaction time is 2-3 h.
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| CN103951564A (en) * | 2014-04-23 | 2014-07-30 | 中国科学院过程工程研究所 | Method for carrying out catalytic degradation on polyethylene glycol terephthalate (PET) by utilizing multi-metal oxygen cluster |
| CN109311798A (en) * | 2016-06-27 | 2019-02-05 | 沙特基础工业全球技术有限公司 | For the method by recycling raw material preparation dimethyl terephthalate ester |
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| JP4680266B2 (en) * | 2005-12-09 | 2011-05-11 | 財団法人くまもとテクノ産業財団 | Polyester depolymerization method, and polyester monomer recovery method using the depolymerization method |
| KR102298521B1 (en) * | 2019-11-28 | 2021-09-06 | 금오공과대학교 산학협력단 | Recovery method for direct polyol from polyethylene terephthalate wastes |
| CN113117748B (en) * | 2021-04-25 | 2022-06-07 | 南京大学 | Bicyclic guanidine salt eutectic solvent catalyst and preparation method and application thereof |
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| CN103951564A (en) * | 2014-04-23 | 2014-07-30 | 中国科学院过程工程研究所 | Method for carrying out catalytic degradation on polyethylene glycol terephthalate (PET) by utilizing multi-metal oxygen cluster |
| CN109311798A (en) * | 2016-06-27 | 2019-02-05 | 沙特基础工业全球技术有限公司 | For the method by recycling raw material preparation dimethyl terephthalate ester |
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