CN1563159A - 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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- CN1563159A CN1563159A CN 200410021429 CN200410021429A CN1563159A CN 1563159 A CN1563159 A CN 1563159A CN 200410021429 CN200410021429 CN 200410021429 CN 200410021429 A CN200410021429 A CN 200410021429A CN 1563159 A CN1563159 A CN 1563159A
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- octanol
- terephthalic acid
- water
- plasticizer
- temperature
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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 60
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 title claims abstract description 58
- 239000004014 plasticizer Substances 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 15
- 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 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 230000032050 esterification Effects 0.000 claims abstract description 20
- 238000005886 esterification reaction Methods 0.000 claims abstract description 20
- 238000005406 washing Methods 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000000463 material Substances 0.000 claims abstract description 14
- 238000001035 drying Methods 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
- 239000008235 industrial water Substances 0.000 claims description 9
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 239000000203 mixture 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
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000000725 suspension Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000002002 slurry Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 239000002274 desiccant Substances 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 239000002994 raw material Substances 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
- 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 claims description 3
- 229940011182 cobalt acetate Drugs 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
- 239000000706 filtrate Substances 0.000 claims description 3
- 238000011010 flushing procedure Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 239000004246 zinc acetate Substances 0.000 claims description 3
- 238000004042 decolorization Methods 0.000 claims description 2
- 238000007599 discharging Methods 0.000 claims description 2
- 238000005554 pickling Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 238000001256 steam distillation Methods 0.000 claims description 2
- 239000002351 wastewater Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 159000000000 sodium salts Chemical class 0.000 abstract description 2
- SUVXSMROEMQBFJ-UHFFFAOYSA-N C(CCCCCCC)O.C(CCCCCCC)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O Chemical compound C(CCCCCCC)O.C(CCCCCCC)O.C(C=1C(C(=O)O)=CC=CC1)(=O)O SUVXSMROEMQBFJ-UHFFFAOYSA-N 0.000 abstract 1
- 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 description 23
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 description 10
- BJAJDJDODCWPNS-UHFFFAOYSA-N dotp Chemical compound O=C1N2CCOC2=NC2=C1SC=C2 BJAJDJDODCWPNS-UHFFFAOYSA-N 0.000 description 8
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 4
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 4
- 239000002131 composite material Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000002649 leather substitute Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000008029 phthalate plasticizer Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A preparing process includes carrying out wate or acid washing for terephthalic acid to remove out monoacid and sodium salt, drying the washed material to be dried agent, putting dried agent of terephthalic acid and octanol into reactor for esterification under action of catalyst and obtaining plasticizer of phthalic acid dioctanol through process of neutralizing, water washing and dealcoholizing.
Description
Technical Field
The invention relates to a process for preparing dioctyl terephthalate plasticizer from terephthalic acid and octanol.
Background
The plasticizer in the prior art is mostly a plasticizer product prepared from dioctyl phthalate and dibutyl phthalate, and is applied to plastics, rubber products and floor leathers. Although the molecular weights of dioctyl terephthalate DOTP and dioctyl phthalate DOP are the same, DOTP molecules are in linear symmetry, and DOP molecules are spherical. When the mixture is heated below 177 ℃ for two hours, the DOTP residue is 77 percent, the DOP is 35 percent, and the DOTP with low volatility is far better than that of dioctyl phthalate DOP.
Dioctyl terephthalate DOTP is a novel phthalic acid plasticizer with outstanding high insulation, low volatility and cold resistance in China in eighties. The dioctyl terephthalate is light yellow oily liquid, the freezing point is-48 ℃, the boiling point is 383 ℃, the volume resistivity is 17 times that of dioctyl phthalate DOP, and the volatilization residual quantity is twice that of DOP. The product has similar toxicity to DOP, and has no irritation to skin.
Disclosure of Invention
The invention aims to provide a process for preparing dioctyl terephthalate plasticizer from terephthalic acid and octanol, which has better performance indexes than plasticizers prepared from dioctyl phthalate and dibutyl phthalate.
The process principle is as follows:
terephthalic acid is first washed with water or acid to remove monobasic acids and sodium salts and then dried to a dry formulation.
Putting terephthalic acid dry agent and octanol (2-ethylhexanol) into a reaction kettle according to a certain proportion, and carrying out esterification, neutralization, water washing, dealcoholization and other processes under the action of a catalyst to obtain the dioctyl phthalate plasticizer.
The water washing step can be omitted if it is used for general plasticizing purposes.
The reaction equation for terephthalic acid and octanol (2-ethylhexanol) is as follows:
the specific process method is described as follows:
1) firstly, washing terephthalic acid with water or acid to remove monoacid and metal impurities so as to ensure the stable quality of the terephthalic acid. Adding industrial water into a washing kettle, adding terephthalic acid under stirring, wherein the volume ratio of the industrial water to the terephthalic acid is 2: 1, measuring the pH value of the suspension when the suspension is uniformly dispersed, and adding a small amount of 1: 1 sulfuric acid when the pH value is more than 6 to adjust the pH value to be less than 5; opening a steam valve to enable the temperature of the materials to reach 60-70 ℃ and the time to last for 30 minutes; and (3) starting the centrifuge, opening the ball valve below the washing kettle, uniformly feeding slurry into the centrifuge, keeping the moisture to be less than 10%, washing with a small amount of industrial water, and filtering.
2) Then filtering and putting the filtrate into a drying system to remove free moisture to obtain a terephthalic acid drying agent; the inlet temperature of hot air is 120-130 ℃, the outlet temperature of materials is 40-60 ℃, and the moisture content is less than or equal to 2%.
3) The raw materials are proportioned (by weight):
| terephthalic acid drying agent | Octanol (I) | Catalyst 1 | Catalyst 2 | Activated carbon |
| 1 | 2.0-2.4 | 0.0015 | 0.003 | 0.003 |
The dried terephthalic acid is put into an esterification kettle according to a specified proportion, and the octanol and the activated carbon according to the weight ratio are put into the esterification kettle and heated to 120 ℃ by heat conducting oil to remove free water. The weighed catalyst 1[ cobalt acetate and zinc acetate 1: 1 mixture]is added, the temperature is continuously raised to 170 ℃, a large amount of water is formed, and a cooling water valve of a reflux condenser is opened. After the catalyst 2[ tetrabutyl titanate]is settled, a valve of the metering tank of the catalyst 2 is opened to add the catalyst 2, and a small amount of octanol is used for flushing the pipeline in time to prevent blockage.
4) The temperature of the materials in the esterification kettle gradually rises along with the increase of the water yield, the final esterification temperature is controlled at 230 ℃, the acidity is measured by sampling, and the reaction is finished when the acidity is less than or equal to 0.3; the temperature of the esterification product is reduced to about 90 ℃ from a filter and a cooler, so that the esterification product is a clear yellow-orange solution.
The plasticizer dioctyl terephthalate DOTP produced bythe invention is a plasticizer with excellent performance. The physical and mechanical properties of the composite are better than those of dioctyl phthalate DOP, and the electrical resistance, the heat resistance, the low-temperature volatility and the like of the composite are better than those of DOP. The product can replace DOP in a PVC plastic cable sheath, and can also be used for producing artificial leather films. In addition, it has excellent compatibility, such as a weather strip for rubber products, no roll phenomenon at the time of kneading, high kneading speed, smooth surface of the product, no bubbles, good tensile properties, and functions to improve hardness and deformability of the product.
In a word, the product of the invention has the advantages of low cost, excellent performance, wide application range and the like, and the performance of the product is far superior to that of a plasticizer taking dioctyl phthalate DOP as a main component.
The properties of dioctyl terephthalate DOTP and dioctyl phthalate DOP are compared in the following Table:
| performance of | Dioctyl phthalate DOP | DOTP dioctyl terephthalate |
| Relative molecular mass | 390.57 | 390.57 |
| viscosity/Pa.S (25 ℃ C.) | 56.5 | 63 |
| Flash point (open dish)/[ deg. ] C | 190 | 220 |
| Volume resistivity at 20 ℃/(Q.cm) | 1.9×1014 | 4.6×1014 |
| Volume resistivity at 70 deg.C/(Q.cm) | 1.2×1012 | 1.7×1013 |
| Elongation at break/% | 310 | 330 |
| 210 ℃ thermal stabilization time/min | ＞90 | ＞140 |
| Weight loss/% | 4.3 | 2.51 |
Detailed Description
Example 1:
the process for preparing dioctyl terephthalate plasticizer from terephthalic acid and octanol for general plasticizing application comprises the following specific process steps:
1) firstly, washing or pickling terephthalic acid with water; adding industrial water into a washing kettle, adding terephthalic acid under stirring, wherein the volume ratio of the industrial water to the terephthalic acid is 2: 1, measuring the pH value of the suspension when the suspension is uniformly dispersed, adding a small amount of 1: 1 sulfuric acid when the pH value is more than 6, and adjusting the pH value to be less than 5; opening a steam valve to enable the temperature of the materials to reach 60-70 ℃ and the time to last for 30 minutes; opening a centrifugal machine, opening a ball valve below a washing kettle, uniformly feeding slurry into the centrifugal machine, keeping the slurry wet and the water content less than 10%, simultaneously washing with a small amount of industrial water, and filtering;
2) then filtering and putting the filtrate into a drying system to remove free moisture to obtain a terephthalic acid drying agent; the inlet temperature of hot air is 120-130 ℃, the outlet temperature of materials is 40-60 ℃, and the moisture content is less than or equal to 2 percent;
3) putting dried terephthalic acid into an esterification kettle according to a specified proportion, putting octanol and activated carbon of the specified proportion into the esterification kettle, heating the octanol and the activated carbon to 120 ℃ by using heat conduction oil, removing free water, adding a weighed catalyst 1 consisting of a mixture of cobalt acetate and zinc acetate in a weight ratio of 1: 1, continuously heating the mixture to 170 ℃, forming a large amount of water, and opening a cooling water valve of a reflux condenser; after the settlement is seen from a window, adding a catalyst 2 tetrabutyl titanate, and flushing the pipeline with a small amount of octanol in time to prevent blockage; the weight ratio of each component is as follows:
terephthalic acid: 1
Octanol: 2.0-2.4
Catalyst 1: 0.0015
Catalyst 2: 0.003
Activated carbon: 0.003.
4) the temperature of the materials in the esterification kettle gradually rises along with the increase of the water yield, the final esterification temperature is controlled at 230 ℃, the acidity is measured by sampling, and the reaction is finished when the acidity is less than or equal to 0.3; the temperature of the esterification product is reduced to about 90 ℃ from a filter and a cooler, so that the esterification product is a clear yellow-orange solution.
Example 2:
the method is used for a refining process, and mainly aims to remove unreacted octanol and catalyst residues and improve the chromaticity of materials so as to ensure the stability of the materials. The specific process steps are as follows:
1) 2), 3), 4) the procedure of example 1.
5) Neutralizing the crude ester with 2% sodium carbonate aqueous solution at a ratio of 20-25 wt% of sodium carbonate aqueous solution, and washing with 75-85 deg.C hot water for 20 min, or adding 50-100ppm demulsifier to accelerate the demixing process.
6) Adding 28-30% hydrogen peroxide into the washed crude ester, wherein the hydrogen peroxide accounts for 1-1.5% of the weight of the raw materials, uniformly adding the hydrogen peroxide after 10 minutes, and decoloring for 20 minutes at 80-110 ℃.
7) After decolorization, a refining kettle vacuum system is started, the materials are heated to 175-180 ℃ under the vacuum condition of-0.08-0.09 Mpa to remove unreacted octanol, a kettle bottom steam valve is opened for steam distillation after 20 minutes, the steam introducing time depends on the flash point of the product, and the steam addition can be stopped when the flash point reaches 180 ℃ through sampling analysis. And (4) separating the steam condensate water and the octanol in a recovery tank, discharging wastewater, and recovering the octanol.
8) Sampling and analyzing the flash point to 180 ℃, controlling the temperature of the plasticizer after octanol removal within 110 ℃, conveying the plasticizer into a filter through an oil pump for filtering, and enabling the filtered plasticizer to be clear and transparent and light yellow and then to be put into a finished product tank.
Claims (2)
1. The process for preparing dioctyl terephthalate plasticizer from terephthalic acid and octanol is characterized by comprising the following process steps:
1) firstly, washing or pickling terephthalic acid with water; adding industrial water into a washing kettle, adding terephthalic acid under stirring, wherein the volume ratio of the industrial water to the terephthalic acid is 2: 1, measuring the pH value of the suspension when the suspension is uniformly dispersed, adding a small amount of 1: 1 sulfuric acid when the pH value is more than 6, and adjusting the pH value to be less than 5; opening a steam valve to enable the temperature of the materials to reach 60-70 ℃ and the time to last for 30 minutes; opening a centrifugal machine, opening a ball valve below a washing kettle, uniformly feeding slurry into the centrifugal machine, keeping the slurry wet and the water content less than 10%, simultaneously washing with a small amount of industrial water, and filtering;
2) then filtering and putting the filtrate into a drying system to remove free moisture to obtain a terephthalic acid drying agent; the inlet temperature of hot air is 120-130 ℃, the outlet temperature of materials is 40-60 ℃, and the moisture content is less than or equal to 2 percent;
3) putting dried terephthalic acid into an esterification kettle according to a specified proportion, putting octanol and activated carbon of the specified proportion into the esterification kettle, heating the octanol and the activated carbon to 120 ℃ by using heat conduction oil, removing free water, adding a weighed catalyst 1 consisting of a mixture of cobalt acetate and zinc acetate in a weight ratio of 1: 1, continuously heating the mixture to 170 ℃, forming a large amount of water, and opening a cooling water valve of a reflux condenser; after the settlement is seen from a window, adding a catalyst 2 tetrabutyl titanate, and flushing the pipeline with a small amount of octanol in time to prevent blockage; the weight ratio of each component is as follows:
terephthalic acid: 1
Octanol: 2.0-2.4
Catalyst 1: 0.0015
Catalyst 2: 0.003
Activated carbon: 0.003.
4) the temperature of the materials in the esterification kettle gradually rises along with the increase of the water yield, the final esterification temperature is controlled at 230 ℃, the acidity is measured by sampling, and the reaction is finished when the acidity is less than or equal to 0.3; the temperature of the esterification product is reduced to about 90 ℃ from a filter and a cooler, so that the esterification product is a clear yellow-orange solution.
2. The process for preparing dioctyl terephthalate plasticizer according to claim 1, wherein the refining process comprises the following steps in addition to the above four steps:
5) neutralizing the crude ester with 2% sodium carbonate aqueous solution, wherein the sodium carbonate aqueous solution accounts for 20-25% of the weight of the raw materials, and washing with 75-85 deg.C hot water for 20 min, and adding 50-100ppm demulsifier to accelerate the demixing;
6) adding 28-30% hydrogen peroxide into the washed crude ester, wherein the hydrogen peroxide accounts for 1-1.5% of the weight of the raw materials, uniformly adding the hydrogen peroxide after 10 minutes, and decoloring for 20 minutes at 80-110 ℃;
7) starting a refining kettle vacuum system after decolorization, heating the material to 175-0.08-0.09 Mpa in vacuum to 180 ℃ to remove unreacted octanol, opening a kettle bottom steam valve for steam distillation after 20 minutes, stopping adding steam when the flash point reaches 180 ℃ through sampling analysis, separating steam condensate from octanol in a recovery tank, discharging wastewater, and recovering octanol;
8) sampling and analyzing the flash point to 180℃, controlling the temperature of the plasticizer after octanol removal within 110 ℃, conveying the plasticizer into a filter through an oil pump for filtering, and enabling the filtered plasticizer to be clear and transparent and light yellow and then to be put into a finished product tank.
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 |
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| 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 true CN1563159A (en) | 2005-01-12 |
| CN1268675C 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 (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100363328C (en) * | 2005-11-08 | 2008-01-23 | 江南大学 | Trimellitic tri(C8-9 ol)ester preparation method |
| CN101805263A (en) * | 2010-03-22 | 2010-08-18 | 江苏雷蒙化工科技有限公司 | Cleaning production method of phthalic acid di-(2-ethyl) ethyl ester |
| CN101139293B (en) * | 2007-08-17 | 2010-08-25 | 郭立耀 | Method for producing dioctyl terephthalate |
| CN101891620A (en) * | 2010-07-03 | 2010-11-24 | 潍坊市元利化工有限公司 | Continuous esterification production method of di-sec-octyl phthalate |
| CN102010337A (en) * | 2010-11-08 | 2011-04-13 | 天津工业大学 | Method and equipment for decoloring dioctyl terephthalate raw ester |
| CN102329233A (en) * | 2011-07-08 | 2012-01-25 | 华侨大学 | Method for catalytically synthesizing diisooctyl terephthalate under action of ionic liquid |
| 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 |
| TWI510535B (en) * | 2013-06-14 | 2015-12-01 | Lg Chemical Ltd | Method for preparing ester plasticizer and ester plasticizer prepared by the same |
| CN107857896A (en) * | 2017-11-16 | 2018-03-30 | 上海炼升化工股份有限公司 | A kind of ester composition from PTA substandard goods and preparation method thereof |
| CN108779291A (en) * | 2016-11-01 | 2018-11-09 | 株式会社Lg化学 | Process for the preparation of ester compositions |
| 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 |
| CN116323547A (en) * | 2021-07-19 | 2023-06-23 | 株式会社Lg化学 | Monomer composition for synthesizing recycled plastic, process for its preparation, recycled plastic using same, molded article, plasticizer composition |
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- 2004-03-18 CN CN 200410021429 patent/CN1268675C/en not_active Expired - Fee Related
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN101805263A (en) * | 2010-03-22 | 2010-08-18 | 江苏雷蒙化工科技有限公司 | Cleaning production method of phthalic acid di-(2-ethyl) ethyl ester |
| 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 |
| CN101891620A (en) * | 2010-07-03 | 2010-11-24 | 潍坊市元利化工有限公司 | Continuous esterification production method of di-sec-octyl phthalate |
| 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 |
| CN102010337A (en) * | 2010-11-08 | 2011-04-13 | 天津工业大学 | Method and equipment for decoloring dioctyl terephthalate raw ester |
| 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 |
| CN102329233A (en) * | 2011-07-08 | 2012-01-25 | 华侨大学 | Method for catalytically synthesizing diisooctyl terephthalate under action of ionic liquid |
| TWI510535B (en) * | 2013-06-14 | 2015-12-01 | Lg Chemical Ltd | Method for preparing ester plasticizer and ester plasticizer prepared by the same |
| US9200138B2 (en) | 2013-06-14 | 2015-12-01 | Lg Chem, Ltd. | Method for preparing ester plasticizer and ester plasticizer prepared by the same |
| 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 |
| CN108779291A (en) * | 2016-11-01 | 2018-11-09 | 株式会社Lg化学 | Process for the preparation of ester compositions |
| US11286229B2 (en) | 2016-11-01 | 2022-03-29 | Lg Chem, Ltd. | Method of preparing ester-based composition |
| CN107857896A (en) * | 2017-11-16 | 2018-03-30 | 上海炼升化工股份有限公司 | A kind of ester composition from PTA substandard goods and preparation method thereof |
| 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 |
| CN116323547A (en) * | 2021-07-19 | 2023-06-23 | 株式会社Lg化学 | Monomer composition for synthesizing recycled plastic, process for its preparation, recycled plastic using same, molded article, plasticizer composition |
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