CN1268675C - Technique for preparing plasticizer of dioctyl terephthalate from terephthalic acid and capryl alcohol - Google Patents
Technique for preparing plasticizer of dioctyl terephthalate from terephthalic acid and capryl alcohol Download PDFInfo
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- CN1268675C CN1268675C CN 200410021429 CN200410021429A CN1268675C CN 1268675 C CN1268675 C CN 1268675C CN 200410021429 CN200410021429 CN 200410021429 CN 200410021429 A CN200410021429 A CN 200410021429A CN 1268675 C CN1268675 C CN 1268675C
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- terephthalic acid
- octanol
- water
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- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 title claims abstract description 64
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 title claims abstract description 58
- OEIWPNWSDYFMIL-UHFFFAOYSA-N dioctyl benzene-1,4-dicarboxylate Chemical compound CCCCCCCCOC(=O)C1=CC=C(C(=O)OCCCCCCCC)C=C1 OEIWPNWSDYFMIL-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000004014 plasticizer Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 25
- 238000005406 washing Methods 0.000 claims abstract description 16
- 238000005516 engineering process Methods 0.000 claims abstract description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 8
- 239000004902 Softening Agent Substances 0.000 claims description 17
- 239000000047 product Substances 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- 238000005070 sampling Methods 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 150000007942 carboxylates Chemical class 0.000 claims description 6
- 239000012065 filter cake Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000004458 analytical method Methods 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 4
- 238000005886 esterification reaction Methods 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 235000021050 feed intake Nutrition 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 238000005554 pickling Methods 0.000 claims description 4
- 238000007670 refining Methods 0.000 claims description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 3
- 238000013019 agitation Methods 0.000 claims description 3
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 3
- 239000000498 cooling water Substances 0.000 claims description 3
- 238000007791 dehumidification Methods 0.000 claims description 3
- 238000011010 flushing procedure Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 238000004062 sedimentation Methods 0.000 claims description 3
- 239000002002 slurry Substances 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 230000000007 visual effect Effects 0.000 claims description 3
- 238000010792 warming Methods 0.000 claims description 3
- 239000004246 zinc acetate Substances 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 2
- 238000004945 emulsification Methods 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 238000001914 filtration Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 claims description 2
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract description 32
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract description 32
- 239000003054 catalyst Substances 0.000 abstract description 3
- 230000009471 action Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000006386 neutralization reaction Methods 0.000 abstract description 2
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- 239000002253 acid Substances 0.000 abstract 1
- 230000005611 electricity Effects 0.000 abstract 1
- BJAJDJDODCWPNS-UHFFFAOYSA-N dotp Chemical compound O=C1N2CCOC2=NC2=C1SC=C2 BJAJDJDODCWPNS-UHFFFAOYSA-N 0.000 description 8
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 150000007518 monoprotic acids Chemical class 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention relates to a technology for preparing a plasticizer of dioctyl terephthalate from terephthalic acid and capryl alcohol. The technology is based on the principle that terephthalic acid is washed with water or acid in order to make monoacid and a sodium salt removed and then is dried into a dry agent. The dry agent of the terephthalic acid and capryl alcohol are put in a reaction kettle, are esterified under the action of a catalyst and is prepared into the plasticizer of dioctyl terephthalate by technologies, such as neutralization, water washing, dealcoholization, etc. The plasticizer prepared by the present invention has better physical and mechanical properties than dioctyl phthalate and is superior to dioctyl phthalate on aspects of electricity resistance, heat resistance, low temperature volatility, etc.
Description
Technical field
The present invention relates to prepare the technology of dioctyl terephthalate softening agent with terephthalic acid and octanol.
Background technology
Softening agent of the prior art is with the softening agent product of dioctyl phthalate (DOP) and dibutyl phthalate preparation mostly, is applied in plastics, rubber item, the flooring laminate.Though dioctyl terephthalate DOTP is identical with the molecular weight of dioctyl phthalate (DOP) DOP, the DOTP molecule is linear symmetry, and the DOP molecule is spherical.Heating respectively below 177 ℃ two hours, the residual amount of DOTP is 77%, and DOP is 35%, and as seen the low volatility with DOTP is much better than dioctyl phthalate (DOP) DOP.
Dioctyl terephthalate DOTP is the novel phthalic acid class softening agent with outstanding high-insulativity, low volatility, cold tolerance that the eighties occurs in China.Dioctyl terephthalate is the pale yellow oily liquid body, zero pour-48 ℃, and 383 ℃ of boiling points, volume specific resistance are 17 times of dioctyl phthalate (DOP) DOP, the volatilization residual quantity is two times of DOP.This product toxicity and DOP are similar, and skin is had no stimulation.
Summary of the invention
The purpose of this invention is to provide a kind of performance index be better than the preparation of dioctyl phthalate (DOP) and dibutyl phthalate softening agent prepare the technology of dioctyl terephthalate softening agent with terephthalic acid and octanol.
Technological principle:
At first terephthalic acid is washed or pickling to remove monoprotic acid and sodium salt, drying becomes dried agent then.
Dried agent of terephthalic acid and octanol (2-Ethylhexyl Alcohol) are dropped in the reactor by a certain percentage, under catalyst action, carry out esterification, become benzene dioctyl dicarboxylic acid elasticizer through technologies such as neutralization, washing, dealcoholysis.
As the plasticising purposes can be saved washing step being used for.
The reaction equation of terephthalic acid and octanol (2-Ethylhexyl Alcohol) is as follows:
Concrete processing method is described below:
1) at first terephthalic acid is washed or pickling, to remove monoprotic acid and metallic impurity, to guarantee the terephthalic acid steady quality.Add service water in the washing still, under agitation drop into terephthalic acid, the volume ratio of service water and terephthalic acid is 2: 1, waits to be uniformly dispersed and measures the suspension pH value, and pH value added 1: 1 sulfuric acid of a small amount of greater than 6 o'clock and regulates pH value less than 5; Open steam valve, make temperature of charge reach 60-70 ℃, time remaining 30 minutes; Open whizzer, open under the washing still ball valve and evenly send into slurry, keep wet cake moisture less than 10%, simultaneously with a small amount of service water washing, formation filter cake toward whizzer.
2) then filter cake is put into dehumidification system and remove free water content, get terephthalic acid and do agent; The hot-wind inlet temperature is 120-130 ℃, and the material outlet temperature is 40-60 ℃, moisture content≤2%.
3) proportioning raw materials (weight ratio):
| Terephthalic acid is done agent | Octanol | Catalyzer 1 | Catalyzer 2 | Gac |
| 1 | 2.0-2.4 | 0.0015 | 0.003 | 0.003 |
The exsiccant terephthalic acid drops in the esterifying kettle to scale, and drops in the esterifying kettle with heat-conducting oil heating to 120 ℃ by the octanol of above-mentioned weight ratio, gac, removes free-water.Add load weighted catalyzer 1[cobaltous acetate and 1: 1 mixture of zinc acetate] continue to be warming up to 170 ℃, there is big water gaging to form, open the reflux exchanger cooling water valve.See from form and to open catalyzer 2[tetrabutyl titanate after sedimentation is arranged] the test tank valve adds catalyzer 2, and in time prevents obstruction with a small amount of octanol flushing pipe.
4) increase the esterifying kettle temperature of charge with aquifer yield and rise gradually, the esterification outlet temperature is controlled at 200-230 ℃, and acidity is surveyed in sampling, and acidity≤0.3 o'clock visual response finishes; From strainer and water cooler the carboxylate temperature is dropped to 90 ℃, make carboxylate be limpid Huang-orange solution.
The softening agent dioctyl terephthalate DOTP that the present invention produces is a kind of softening agent of excellent performance.Neighbour dioctyl phthalate DOP is more good for its physical and mechanical properties, and aspects such as its electric durability, thermotolerance, low temperature volatility all are better than DOP.This product is alternative DOP in PVC plastic cable sheath, also can be used for the production of leatheroid film.In addition, have good consistency, for example be used for the sealed strip of rubber item, do not have the roll banding phenomenon when mixing, its mixing speed is fast, and product surface is smooth, does not have bubble, and tensile property is good, and plays a part to improve goods hardness and deformability.
In a word, product of the present invention has advantages such as reduce cost, excellent property, use range are wide, and it is the softening agent of principal constituent that its performance is far superior to dioctyl phthalate (DOP) DOP.
The performance of dioctyl terephthalate DOTP and dioctyl phthalate (DOP) DOP relatively sees the following form:
| Performance | Dioctyl phthalate (DOP) DOP | Dioctyl terephthalate DOTP |
| Relative molecular mass | 390.57 | 390.57 |
| Viscosity/Pa.S (25 ℃) | 56.5 | 63 |
| Flash-point (driving ware)/℃ | 190 | 220 |
| Volume specific resistance in the time of 20 ℃/(Q.cm) | 1.9×10 14 | 4.6×10 14 |
| Volume specific resistance in the time of 70 ℃/(Q.cm) | 1.2×10 12 | 1.7×10 13 |
| Elongation at break/% | 310 | 330 |
| 210 ℃ of heat-stable time/min | ＞90 | ＞140 |
| Weightlessness/% | 4.3 | 2.51 |
Embodiment
Embodiment 1:
Be used for general plasticising purposes, terephthalic acid and octanol prepare the technology of dioctyl terephthalate softening agent, and its concrete processing step is as follows:
1) at first terephthalic acid is washed or pickling; Add service water in the washing still, under agitation drop into terephthalic acid, the volume ratio of service water and terephthalic acid is 2: 1, waits to be uniformly dispersed and measures the suspension pH value, and pH value added 1: 1 sulfuric acid in a small amount greater than 6 o'clock, regulated pH value less than 5; Open steam valve, make temperature of charge reach 60-70 ℃, time remaining 30 minutes; Open whizzer, open under the washing still ball valve and evenly send into slurry, keep wet cake moisture less than 10%, simultaneously with a small amount of service water washing, formation filter cake toward whizzer;
2) then filter cake is put into dehumidification system and remove free water content, get terephthalic acid and do agent; The hot-wind inlet temperature is 120-130 ℃, and the material outlet temperature is 40-60 ℃, moisture content≤2%;
3) the exsiccant terephthalic acid drops in the esterifying kettle to scale, and the octanol, gac that will stipulate ratio drop in the esterifying kettle with heat-conducting oil heating to 120 ℃, remove free-water, add load weighted catalyzer 1 then by cobaltous acetate and 1: 1 weight ratio mixture formation of zinc acetate, continue to be warming up to 170 ℃, there is big water gaging to form, opens the reflux exchanger cooling water valve; From form see sedimentation is arranged after, add catalyzer 2 tetrabutyl titanates, and in time prevent obstruction with a small amount of octanol flushing pipe; The weight part ratio of each composition is for example following:
Terephthalic acid: 1
Octanol: 2.0-2.4
Catalyzer 1:0.0015
Catalyzer 2:0.003
Gac: 0.003.
4) increase the esterifying kettle temperature of charge with aquifer yield and rise gradually, the esterification outlet temperature is controlled at 200-230 ℃, and acidity is surveyed in sampling, and acidity≤0.3 o'clock visual response finishes; From strainer and water cooler the carboxylate temperature is dropped to 90 ℃, make carboxylate be limpid Huang-orange solution.
Embodiment 2:
Be used for process for refining, main purpose is the colourity of removing unreacted octanol, catalyst residue and improving material, to guarantee the stability of material.Its concrete processing step is as follows:
1), 2), 3), 4) step is with embodiment 1.
5) with 2% aqueous sodium carbonate neutralized crude esters, account for the ratio of several weight percent 20%-25% that feed intake in aqueous sodium carbonate, 20 minutes time,, layering is accelerated as make layering slowly can add the 50-100ppm emulsion splitter because of emulsification then with 75-85 ℃ of hot water washing 20 minutes.
6) the thick ester adding in washing back concentration is the hydrogen peroxide of 28-30%, and hydrogen peroxide accounts for the 1-1.5% of several weight percents that feed intake, and evenly adds in 10 minutes, 80-110 ℃ of decolouring 20 minutes.
7) start the refining kettle vacuum system after the decolouring, under vacuum-0.08-0.09Mpa condition, add thermal material and remove unreacted octanol to 175-180 ℃, steam valve carries out wet distillation at the bottom of opening still after 20 minutes, the logical steam time decides on the product flash-point, can stop to add steam when the sampling analysis flash-point reaches 180 ℃.Steam condensate separates the back with octanol and discharges waste water in withdrawing can, reclaim octanol.
8) after the sampling analysis flash-point reached 180 ℃, the temperature that will take off the softening agent of octanol was controlled in 110 ℃, is transported to the filter inner filtration through oil pump then, and the softening agent after having filtered reaches limpid transparent faint yellow can go into the finished product jar.
Claims (2)
1, terephthalic acid and octanol prepare the technology of dioctyl terephthalate softening agent, it is characterized in that its processing step is as follows:
1) at first terephthalic acid is washed or pickling; Add service water in the washing still, under agitation drop into terephthalic acid, the volume ratio of service water and terephthalic acid is 2: 1, waits to be uniformly dispersed and measures the suspension pH value, and pH value added 1: 1 sulfuric acid in a small amount greater than 6 o'clock, regulated pH value less than 5; Open steam valve, make temperature of charge reach 60-70 ℃, time remaining 30 minutes; Open whizzer, open under the washing still ball valve and evenly send into slurry, keep wet cake moisture less than 10%, simultaneously with a small amount of service water washing, formation filter cake toward whizzer;
2) then filter cake is put into dehumidification system and remove free water content, get terephthalic acid and do agent; The hot-wind inlet temperature is 120-130 ℃, and the material outlet temperature is 40-60 ℃, moisture content≤2%;
3) the exsiccant terephthalic acid drops in the esterifying kettle to scale, and the octanol, gac that will stipulate ratio drop in the esterifying kettle with heat-conducting oil heating to 120 ℃, remove free-water, add load weighted catalyzer 1 then by cobaltous acetate and 1: 1 weight ratio mixture formation of zinc acetate, continue to be warming up to 170 ℃, there is big water gaging to form, opens the reflux exchanger cooling water valve; From form see sedimentation is arranged after, add catalyzer 2 tetrabutyl titanates, and in time prevent obstruction with a small amount of octanol flushing pipe; The weight part ratio of each composition is for example following:
Terephthalic acid: 1
Octanol: 2.0-2.4
Catalyzer 1:0.0015
Catalyzer 2:0.003
Gac: 0.003
4) increase the esterifying kettle temperature of charge with aquifer yield and rise gradually, the esterification outlet temperature is controlled at 200-230 ℃, and acidity is surveyed in sampling, and acidity≤0.3 o'clock visual response finishes; From strainer and water cooler the carboxylate temperature is dropped to 90 ℃, make carboxylate be limpid Huang-orange solution.
2, terephthalic acid according to claim 1 and octanol prepare the technology of dioctyl terephthalate softening agent, it is characterized in that refining step except that comprising above-mentioned four steps, also comprise the steps:
5) with 2% aqueous sodium carbonate neutralized crude esters, account for the ratio of several weight percent 20%-25% that feed intake in aqueous sodium carbonate, 20 minutes time,, layering is accelerated as make layering slowly can add the 50-100ppm emulsion splitter because of emulsification then with 75-85 ℃ of hot water washing 20 minutes;
6) the thick ester adding in washing back concentration is the hydrogen peroxide of 28-30%, and hydrogen peroxide accounts for the 1-1.5% of several weight percents that feed intake, and evenly adds in 10 minutes, 80-110 ℃ of decolouring 20 minutes;
7) start the refining kettle vacuum system after the decolouring, under vacuum-0.08-0.09Mpa condition, add thermal material and remove unreacted octanol to 175-180 ℃, steam valve carries out wet distillation at the bottom of opening still after 20 minutes, the logical steam time decides on the product flash-point, when reaching 180 ℃, the sampling analysis flash-point can stop to add steam, steam condensate separates the back with octanol and discharges waste water in withdrawing can, reclaim octanol;
8) after the sampling analysis flash-point reached 180 ℃, the temperature that will take off the softening agent of octanol was controlled in 110 ℃, is transported to the filter inner filtration through oil pump then, and the softening agent after having filtered reaches limpid transparent faint yellow can go into the finished product jar.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410021429 CN1268675C (en) | 2004-03-18 | 2004-03-18 | Technique for preparing plasticizer of dioctyl terephthalate from terephthalic acid and capryl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200410021429 CN1268675C (en) | 2004-03-18 | 2004-03-18 | Technique for preparing plasticizer of dioctyl terephthalate from terephthalic acid and capryl alcohol |
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| Publication Number | Publication Date |
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| CN1563159A CN1563159A (en) | 2005-01-12 |
| CN1268675C true CN1268675C (en) | 2006-08-09 |
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| CN 200410021429 Expired - Fee Related CN1268675C (en) | 2004-03-18 | 2004-03-18 | Technique for preparing plasticizer of dioctyl terephthalate from terephthalic acid and capryl alcohol |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US12538424B2 (en) | 2013-04-29 | 2026-01-27 | Samsung Display Co., Ltd. | Electronic component, electric device including the same, and bonding method thereof |
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| CN100363328C (en) * | 2005-11-08 | 2008-01-23 | 江南大学 | Trimellitic tri(C8-9 ol)ester preparation method |
| CN101139293B (en) * | 2007-08-17 | 2010-08-25 | 郭立耀 | Method for producing dioctyl terephthalate |
| CN101805263B (en) * | 2010-03-22 | 2012-07-25 | 江苏雷蒙化工科技有限公司 | Cleaning production method of phthalic acid di-(2-ethyl) ethyl ester |
| CN101891620B (en) * | 2010-07-03 | 2013-12-18 | 山东元利科技股份有限公司 | Continuous esterification production method of di-sec-octyl phthalate |
| CN102010337B (en) * | 2010-11-08 | 2013-06-05 | 天津工业大学 | Method and equipment for decoloring dioctyl terephthalate raw ester |
| CN102329233B (en) * | 2011-07-08 | 2013-12-18 | 华侨大学 | Method for catalytically synthesizing diisooctyl terephthalate under action of ionic liquid |
| WO2014200138A1 (en) * | 2013-06-14 | 2014-12-18 | (주) 엘지화학 | Method for producing ester-based plasticizer and ester-based plasticizer produced thereby |
| CN104230714A (en) * | 2013-06-22 | 2014-12-24 | 上海蓓奕化工有限公司 | Process of recycling terephthalic acid to produce DOTP (dioctyl terephthalate) by using polyester alkaline to reduce wastewater |
| KR101742923B1 (en) | 2016-11-01 | 2017-06-01 | 주식회사 엘지화학 | Method of preparing ester-based composition |
| CN107857896B (en) * | 2017-11-16 | 2019-07-09 | 上海炼升化工股份有限公司 | A kind of ester composition and preparation method thereof from PTA substandard goods |
| CN111732510A (en) * | 2020-07-03 | 2020-10-02 | 山东朗晖石油化学股份有限公司 | Continuous production equipment and process for DOTP plasticizer |
| EP4201988A4 (en) * | 2021-07-19 | 2025-04-09 | Lg Chem, Ltd. | MONOMER COMPOSITION FOR SYNTHESIS OF RECYCLED PLASTIC MATERIAL, PREPARATION METHOD THEREOF, AND RECYCLED PLASTIC MATERIAL, MOLDED ARTICLE AND PLASTICIZER COMPOSITION EACH USING SAME |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US12538424B2 (en) | 2013-04-29 | 2026-01-27 | Samsung Display Co., Ltd. | Electronic component, electric device including the same, and bonding method thereof |
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