CN108484392A - The method that choline eutectic ionic liquid catalyzed alcoholysis polyethylene terephthalate prepares Di-2-ethylhexyl terephthalate - Google Patents
The method that choline eutectic ionic liquid catalyzed alcoholysis polyethylene terephthalate prepares Di-2-ethylhexyl terephthalate Download PDFInfo
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Abstract
The present invention relates to the methods that one kind preparing Di-2-ethylhexyl terephthalate (DOTP) with new catalyst catalyzed alcoholysis polyethylene terephthalate (PET), its feature is the catalyst using choline eutectic ionic liquid as alcoholysis, using choline chloride as hydrogen bond donor when catalyst synthesizes, metal salt is hydrogen bond receptor.Solvent is made with isooctanol in reaction process, is 1 in raw material and solvent molar ratio:2.5~1:8, reaction temperature is 145 DEG C~185 DEG C, normal pressure, and the reaction time is 30min~180min, and catalyst amount carries out alcoholysis PET under conditions of being the 0.5%~10% of material quality.This method has many advantages, such as that catalyst preparation is simple, at low cost, reaction condition is mild, the reaction time is short, efficient, PET high conversion rates, target product selectivity are high and reaction process is environmentally protective.
Description
Technical field
The invention belongs to green, clean catalysis technical fields, are related to a kind of new catalyst catalytic alcohol depolymerization terephthaldehyde
The method that sour glycol ester (PET) prepares Di-2-ethylhexyl terephthalate.
Background technology
Di-2-ethylhexyl terephthalate (DOTP) also known as terephthalic acid (TPA) two (2- ethyl hexyls), are to grow up in recent years
New plasticizer, be applied to a kind of primary plasticizer of function admirable in polyvinyl chloride (PVC) plastics, application is very extensive.
DOTP is low as the toxicity that plasticizer uses, safe, is acknowledged as nontoxic plasticizer always, can use medical
In PVC product and plastic toy.
Up to the present, industrially the method for synthesis DOTP mainly has 3 kinds：First, terephthalic acid (TPA) and the direct ester of isooctanol
Change method；Second is that dimethyl terephthalate (DMT) ester-interchange method；Third, polyethylene terephthalate waste material alcoholysis method (PET methods).
In addition in addition to this 3 kinds of methods, there is paraphthaloyl chloride method on theoretic.To raw material when preparing DOTP using first two method
It is more demanding, and reaction process is complex, and reaction cost is high, so polyethylene terephthalate waste material the preparation method
(PET methods) is a kind of method of current most study, because will produce many waste materials in polyester industrial production, recycles these
Waste material, which prepares plasticizer, to turn waste into wealth Waste Polyester, and new profit growth point can be more brought to enterprise, increase enterprise
The benefit of industry.The catalyst of this technique routine is the concentrated sulfuric acid, zinc chloride, butyl titanate, sodium hydroxide and solid acid etc..But
These catalyst there is catalyst unstable, etching apparatus, activation of catalyst overlong time cause reaction slowly and reaction
A series of problems, such as required temperature is higher.
Because ionic liquid has apparent Green Chemistry property, ionic liquid is applied to certain catalysis reactions
In, those conventional toxics, seriously polluted non-environmental protection catalyst can be replaced.With the continuous depth studied ionic liquid
Enter, researcher has found, when certain SOLID ORGANIC molecules and specific ionic compound are mixed in a certain ratio, room can be obtained
The lower eutectic mixture in liquid condition of temperature also contained a certain number of organic molecules wherein both having contained ion component.It is this kind of
Eutectic ionic liquid does not show only physicochemical properties similar with conventional ion liquid, also has and is easy preparation, price
It is cheap, convenient for advantages such as storage and atom utilizations very.The advantage having by itself, eutectic ionic liquid
Growing interest is caused in many research fields, about eutectic ionic liquid as cheap and safety solvent
Or research of the catalyst for many catalytic process is also more and more.
In the reaction that choline chloride and the eutectic catalyst of metal salt synthesis are prepared to DOTP for the PET that degrades, catalysis
Agent shows very high activity, and the reaction time can reduce 5 to 8 times compared with traditional catalyst, and reaction required temperature also has obviously
Decline.It is combined with the effect of the ligand complex of hydrogen bond or metal between two kinds of raw materials, the high activity of catalyst is primarily due to
The synergistic effect that choline and metal ion are formed, carbonyl that can simultaneously on the hydroxyl and PET long-chains on attack alcohol accelerate long-chain disconnected
It opens and is connected with octanol and synthesize DOTP.The reaction process has mild condition, reaction rate fast, green compared with traditional reaction process
Colour circle protect the advantages that, for recycle waste PET prepare environment-friendly plasticizer DOTP provide it is a kind of efficiently feasible new method.
Invention content
Present invention research using eutectic ionic liquid as catalyst, using isooctanol as solvent, under mild reaction conditions,
Realize that green energy conservation, high efficiency, high conversion and highly selective catalyzed alcoholysis PET prepare Di-2-ethylhexyl terephthalate
(DOTP) process.
The present invention reaction formula be：
Using choline chloride and metal salt as the eutectic ionic liquid catalyst alcoholysis poly terephthalic acid second of Material synthesis
The method that diol ester prepares Di-2-ethylhexyl terephthalate, it is characterised in that using isooctanol as solvent, with choline chloride and acetic acid
A kind of eutectic ionic liquid catalyst of metal salt synthesis in zinc, zinc chloride, zinc nitrate, zinc sulfate, manganese acetate, copper nitrate
Alcoholysis polyethylene terephthalate prepares Di-2-ethylhexyl terephthalate.
The polyethylene terephthalate raw material sources degraded are in mineral water bottle, carbonated drink bottle and tea beverage bottle
One or more of mixtures or polyethylene terephthalate particle.
It is described low as Material synthesis using choline chloride with zinc acetate, zinc chloride, zinc nitrate, zinc sulfate, manganese acetate, copper nitrate
When congruent melting ionic liquid, the molar ratio of choline chloride and metal salt is 1:0.1~1:2.
It is described low as Material synthesis using choline chloride with zinc acetate, zinc chloride, zinc nitrate, zinc sulfate, manganese acetate, copper nitrate
When congruent melting ionic liquid, reaction temperature is 50 DEG C~120 DEG C, and the reaction time is 30min~240min.
The catalyst amount is the 0.5%~10% of polyethylene terephthalate quality.
It is described that the preparation of catalyst degradation polyethylene terephthalate is made to benzene two with choline eutectic ionic liquid
The raw material of formic acid di-isooctyl is 1 with solvent molar ratio:2.5~1:8.
It is described that the preparation of catalyst degradation polyethylene terephthalate is made to benzene two with choline eutectic ionic liquid
The reaction temperature of formic acid di-isooctyl is 145 DEG C~185 DEG C.
It is described that the preparation of catalyst degradation polyethylene terephthalate is made to benzene two with choline eutectic ionic liquid
The reaction time of formic acid di-isooctyl is 30min~180min.
After reaction, the selectivity of the degradation rate of PET and product is pressed formula (1) (2) and is calculated respectively：
Wherein, A indicates that the initial mass for the PET being added, B indicate the quality of undegraded PET after reaction.
Specific embodiment
The present invention is illustrated with following embodiment, but the present invention is not limited in following embodiments, front and back not departing from
Under the range of affiliated objective, change is included in the technical scope of the present invention.
Embodiment 1
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:2, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 175 DEG C, normal pressure, after condensing reflux reacts 60min
It is cooled to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
78.2%.
Embodiment 2
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1.5, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, and normal pressure, condensing reflux reacts 60min
Postcooling is to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
82.5%.
Embodiment 3
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:0.25, synthesis condition is 50 DEG C, 240min.Controlling reaction temperature is 185 DEG C, and normal pressure, condensing reflux reacts 60min
Postcooling is to room temperature.With this condition, the degradation rate of PET is 99.2%, the selectivity of Di-2-ethylhexyl terephthalate (DOTP)
It is 79.4%.
Embodiment 4
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:2, synthesis condition is 90 DEG C, 180min.Controlling reaction temperature is 175 DEG C, normal pressure, cold after condensing reflux reaction 60min
But to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
78.4%.
Embodiment 5
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:0.25, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 175 DEG C, and normal pressure, condensing reflux reacts 120min
Postcooling is to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
75.3%.
Embodiment 6
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:0.1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 175 DEG C, and normal pressure, condensing reflux reacts 120min
Postcooling is to room temperature.With this condition, the degradation rate of PET is 98.7%, the selectivity of Di-2-ethylhexyl terephthalate (DOTP)
It is 79.4%.
Embodiment 7
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 85 DEG C, 120min.Controlling reaction temperature is 155 DEG C, normal pressure, after condensing reflux reacts 120min
It is cooled to room temperature.With this condition, the degradation rate of PET is 88.3%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
93.4%.
Embodiment 8
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 100 DEG C, 90min.Controlling reaction temperature is 145 DEG C, normal pressure, after condensing reflux reacts 180min
It is cooled to room temperature.With this condition, the degradation rate of PET is 83.9%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
94.6%.
Embodiment 9
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 80 DEG C, 120min.Controlling reaction temperature is 185 DEG C, normal pressure, after condensing reflux reacts 180min
It is cooled to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
84.5%.
Embodiment 10
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 120 DEG C, 60min.Controlling reaction temperature is 145 DEG C, normal pressure, after condensing reflux reacts 180min
It is cooled to room temperature.With this condition, the degradation rate of PET is 93.9%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
94.6%.
Embodiment 11
Using PET particles as raw material, 5.0gPET raw materials, 27.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 120 DEG C, 30min.Controlling reaction temperature is 155 DEG C, normal pressure, after condensing reflux reacts 180min
It is cooled to room temperature.With this condition, the degradation rate of PET is 95.9%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
95.7%.
Embodiment 12
Using PET particles as raw material, 5.0gPET raw materials, 12.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:2, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 145 DEG C, normal pressure, after condensing reflux reacts 180min
It is cooled to room temperature.With this condition, the degradation rate of PET is 97.9%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
94.4%.
Embodiment 13
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and copper nitrate, the two mole
Than being 1:1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, normal pressure, after condensing reflux reacts 120min
It is cooled to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
78.4%.
Embodiment 14
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and manganese acetate, the two mole
Than being 1:1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, normal pressure, after condensing reflux reacts 120min
It is cooled to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
79.2%.
Embodiment 15
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc sulfate, the two mole
Than being 1:1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, normal pressure, after condensing reflux reacts 120min
It is cooled to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
78.9%.
Embodiment 16
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.5g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 60 DEG C, 180min.Controlling reaction temperature is 175 DEG C, normal pressure, cold after condensing reflux reaction 30min
But to room temperature.With this condition, the degradation rate of PET is 97.5%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
84.7%.
Embodiment 17
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc chloride, the two mole
Than being 1:1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, normal pressure, after condensing reflux reacts 120min
It is cooled to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
82.8%.
Embodiment 18
For the Sprite bottle piece of 0.5cm × 0.5cm it is PET raw materials with the length of side, is sequentially added in 50ml three neck round bottom flask
The raw material of 5.0gPET raw materials, 17.0g isooctanol and 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is chlorine
Change choline and zinc chloride, the two molar ratio is 1:1, synthesis condition is 80 DEG C, 120min.Controlling reaction temperature is 185 DEG C, often
Pressure, condensing reflux react 120min postcoolings to room temperature.With this condition, the degradation rate of PET is 100%, terephthalic acid (TPA) two
The selectivity of different monooctyl ester (DOTP) is 80.6%.
Embodiment 19
Mineral water bottle piece with the length of side for 0.5cm × 0.5cm is PET raw materials, is added successively in 50ml three neck round bottom flask
Entering 5.0gPET raw materials, 17.0g isooctanol and 0.25g choline eutectic ionic liquid catalyst, the raw material of synthetic catalyst is
Choline chloride and zinc nitrate, the two molar ratio are 1:1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, often
Pressure, condensing reflux react 120min postcoolings to room temperature.With this condition, the degradation rate of PET is 100%, terephthalic acid (TPA) two
The selectivity of different monooctyl ester (DOTP) is 79.4%.
Embodiment 20
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.5g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two mole
Than being 1:1, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, normal pressure, cold after condensing reflux reaction 60min
But to room temperature.With this condition, the degradation rate of PET is 100%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
83.5%.
Embodiment 21
Using PET particles as raw material, sequentially added in 50ml three neck round bottom flask 5.0gPET raw materials, 8.5g isooctanol and
The raw material of 0.25g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, the two molar ratio
It is 1:2, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, and normal pressure, condensing reflux reacts 60min postcoolings
To room temperature.With this condition, the degradation rate of PET is 97.5%, and the selectivity of Di-2-ethylhexyl terephthalate (DOTP) is
74.4%.
Embodiment 22
Using PET particles as raw material, 5.0gPET raw materials, 17.0g isooctanol are sequentially added in 50ml three neck round bottom flask
Raw material with 0.025g choline eutectic ionic liquid catalyst, synthetic catalyst is choline chloride and zinc acetate, and the two is rubbed
You are than being 1:2, synthesis condition is 70 DEG C, 120min.Controlling reaction temperature is 185 DEG C, and normal pressure, condensing reflux reacts 120min
Postcooling is to room temperature.With this condition, the degradation rate of PET is 99.5%, the selectivity of Di-2-ethylhexyl terephthalate (DOTP)
It is 77.6%.
Claims (7)
1. using choline chloride and metal salt as the eutectic ionic liquid catalyst alcoholysis poly terephthalic acid second two of Material synthesis
The method that alcohol ester (PET) prepares Di-2-ethylhexyl terephthalate (DOTP) makees solvent, catalyst and poly- terephthaldehyde with isooctanol
Sour glycol ester hybrid reaction degradation.With choline chloride and metal salt when its feature is to prepare the catalyst：Zinc acetate, chlorine
It is raw material to change zinc, zinc nitrate, zinc sulfate, manganese acetate, copper nitrate.
2. catalyst according to claim 1, feature are choline chloride and metal salt：Zinc acetate, zinc chloride, nitric acid
Zinc, zinc sulfate, manganese acetate, copper nitrate molar ratio be 1:0.1~1:2.
3. the method for preparing catalyst described in claim 1, when feature is to prepare catalyst reaction temperature be 50 DEG C~
120 DEG C, the reaction time is 30min~240min.
4. according to the method described in claim 1, its feature is that catalyst amount is polyethylene terephthalate raw material
The 0.5%~10% of quality.
5. according to the method described in claim 1, its feature is that reaction temperature is 145 DEG C~185 DEG C.
6. according to the method described in claim 1, its feature is that raw material and solvent molar ratio are 1:2.5~1:8.
7. according to the method described in claim 1, its feature is that the reaction time is 30min~180min.
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| CN110433856A (en) * | 2019-08-13 | 2019-11-12 | 中国科学院过程工程研究所 | A kind of method of the preparation of glycine eutectic solvent and its efficient catalytic degradation polyester fiber |
| CN111217700A (en) * | 2020-02-19 | 2020-06-02 | 中国科学院过程工程研究所 | Method for catalyzing alcoholysis of polyethylene terephthalate by using non-metal choline ionic liquid |
| CN113117748A (en) * | 2021-04-25 | 2021-07-16 | 南京大学 | Bicyclic guanidine salt eutectic solvent catalyst and preparation method and application thereof |
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| KR20230158163A (en) | 2022-05-10 | 2023-11-20 | 주식회사 엘지화학 | Novel catalyst, method for preparing thereof and method for preparing ester based monomer using the same |
| KR20230172186A (en) | 2022-06-15 | 2023-12-22 | 주식회사 엘지화학 | Method for preparing ester based monomer |
| KR20240006123A (en) | 2022-07-05 | 2024-01-15 | 주식회사 엘지화학 | Novel catalyst, method for preparing thereof and method for preparing ester based monomer using the same |
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| CN109529939A (en) * | 2019-01-03 | 2019-03-29 | 中国科学院过程工程研究所 | A kind of eutectic solvent catalyst of alcoholysis PET and preparation method thereof |
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| CN110433856B (en) * | 2019-08-13 | 2020-10-02 | 中国科学院过程工程研究所 | Preparation of glycine eutectic solvent and method for efficiently catalyzing and degrading polyester fibers by using glycine eutectic solvent |
| CN111217700A (en) * | 2020-02-19 | 2020-06-02 | 中国科学院过程工程研究所 | Method for catalyzing alcoholysis of polyethylene terephthalate by using non-metal choline ionic liquid |
| CN113117748A (en) * | 2021-04-25 | 2021-07-16 | 南京大学 | Bicyclic guanidine salt eutectic solvent catalyst and preparation method and application thereof |
| CN113117748B (en) * | 2021-04-25 | 2022-06-07 | 南京大学 | Bicyclic guanidine salt eutectic solvent catalyst and preparation method and application thereof |
| WO2023175524A1 (en) * | 2022-03-16 | 2023-09-21 | Formula - Centro Di Ricerca E Sviluppo Deep Tech S.R.L. | Pet depolymerization process |
| KR20230157789A (en) | 2022-05-10 | 2023-11-17 | 주식회사 엘지화학 | Method for preparing ester based monomer |
| KR20230158163A (en) | 2022-05-10 | 2023-11-20 | 주식회사 엘지화학 | Novel catalyst, method for preparing thereof and method for preparing ester based monomer using the same |
| KR20230172186A (en) | 2022-06-15 | 2023-12-22 | 주식회사 엘지화학 | Method for preparing ester based monomer |
| KR20240006123A (en) | 2022-07-05 | 2024-01-15 | 주식회사 엘지화학 | Novel catalyst, method for preparing thereof and method for preparing ester based monomer using the same |
| KR20240016065A (en) | 2022-07-28 | 2024-02-06 | 주식회사 엘지화학 | Method for preparing terephthalic acid |
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