CN111040246A - Improved preparation method of dioctyl adipate - Google Patents
Improved preparation method of dioctyl adipate Download PDFInfo
- Publication number
- CN111040246A CN111040246A CN201911109992.0A CN201911109992A CN111040246A CN 111040246 A CN111040246 A CN 111040246A CN 201911109992 A CN201911109992 A CN 201911109992A CN 111040246 A CN111040246 A CN 111040246A
- Authority
- CN
- China
- Prior art keywords
- parts
- dioctyl adipate
- octanol
- reaction kettle
- catalyst
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 21
- ZFMQKOWCDKKBIF-UHFFFAOYSA-N bis(3,5-difluorophenyl)phosphane Chemical compound FC1=CC(F)=CC(PC=2C=C(F)C=C(F)C=2)=C1 ZFMQKOWCDKKBIF-UHFFFAOYSA-N 0.000 title claims abstract description 19
- KBPLFHHGFOOTCA-UHFFFAOYSA-N caprylic alcohol Natural products CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims abstract description 34
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 30
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims abstract description 30
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 24
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000011037 adipic acid Nutrition 0.000 claims abstract description 15
- 239000001361 adipic acid Substances 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 claims abstract description 15
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000463 material Substances 0.000 claims abstract description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000007788 liquid Substances 0.000 claims abstract description 11
- 238000010438 heat treatment Methods 0.000 claims abstract description 10
- 238000001816 cooling Methods 0.000 claims abstract description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 5
- 230000001502 supplementing effect Effects 0.000 claims abstract 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- 239000000047 product Substances 0.000 claims description 7
- 235000011121 sodium hydroxide Nutrition 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 11
- 239000004014 plasticizer Substances 0.000 abstract description 4
- 239000002585 base Substances 0.000 abstract description 2
- 230000003472 neutralizing effect Effects 0.000 description 4
- 239000003518 caustics Substances 0.000 description 3
- 229920000915 polyvinyl chloride Polymers 0.000 description 3
- 239000004800 polyvinyl chloride Substances 0.000 description 3
- 238000007865 diluting Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/11—Esters; Ether-esters of acyclic polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/10—Esters; Ether-esters
- C08K5/12—Esters; Ether-esters of cyclic polycarboxylic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to an improved preparation method of dioctyl adipate, which comprises the steps of taking 8-12 parts of adipic acid, 8-12 parts of terephthalic acid, 8-12 parts of trimellitic anhydride, 0.5-5.5 parts of catalyst and 64-76 parts of n-octanol, feeding the materials into a reaction kettle, filling nitrogen, heating by using heat conduction oil, adding a proper amount of tetraisopropyl titanate, heating to 180 ℃ and 210 ℃, esterifying for 15-20 hours under normal pressure, cooling by using a condenser, adding a proper amount of liquid alkali diluted by using water IV to one in the reaction kettle, vacuumizing, supplementing water and dealcoholizing for three hours, and pressurizing by using a filter circulating pump until diatomite and activated carbon are filtered and decolored to obtain a finished product. Through adopting the adipic acid that cold resistance is strong, n-octanol, trimellitic anhydride that the heat resistance is strong to take the good terephthalic acid of plastification effect as the base material and stable in structure after the reaction of reaction kettle high temperature, thereby plastification effect, cold-resistant effect, heat-resisting effect have obtained comparatively obvious promotion in PVC hard material, but wide application in plasticizer technical field.
Description
Technical Field
The invention relates to the technical field of plasticizers, in particular to a preparation method of improved dioctyl adipate.
Background
According to the prior art, PVC products are soft and hard, wherein the cold resistance of the products can only be improved by directly adding dioctyl adipate when the hard polyvinyl chloride material needs to be plasticized, the plasticizing effect is poor, the heat resistance is poor, and the ideal effect can be achieved by matching other plasticizers. However, the prior art does not have a material which can meet the requirements.
Therefore, a plasticizer having good plasticizing, cold-resistant and heat-resistant effects is yet to be studied.
Disclosure of Invention
In order to solve the technical problems, the technical scheme provided by the invention is as follows:
an improved dioctyl adipate preparation method comprises the steps of feeding 8-12 parts of adipic acid, 8-12 parts of terephthalic acid, 8-12 parts of trimellitic anhydride and 64-76 parts of n-octanol into a reaction kettle, filling nitrogen, heating to 120 ℃ by using steam, heating to 180 ℃ by using heat conduction oil, adding a proper amount of tetraisopropyl titanate, heating to 180 ℃ and 210 ℃, esterifying for about 15-20 hours under normal pressure, closing the nitrogen, cooling by using a condenser, adding a proper amount of liquid alkali diluted by using water IV to one into the reaction kettle, vacuumizing, replenishing water and dealcoholizing for three hours, cooling to 110 by using a condenser, adding a proper amount of liquid alkali diluted by using water IV to one into the reaction kettle, neutralizing, dehydrating for one hour to obtain an improved dioctyl adipate crude product, and pressurizing by using a filter circulating pump until diatomite and activated carbon are filtered and decolored to obtain a finished product.
Further, the catalyst is tetraisopropyl titanate.
Further, the content of the catalyst is 0.5-5.5 parts.
Further, during specific preparation, 20 parts of adipic acid, 20 parts of terephthalic acid, 10 parts of trimellitic anhydride, 45 parts of n-octanol and 5 parts of a catalyst are selected as main materials.
Further, during specific preparation, 19 parts of adipic acid, 8 parts of terephthalic acid, 8 parts of trimellitic anhydride, 40 parts of n-octanol and 4.5 parts of a catalyst are selected as main materials.
Further, during specific preparation, 22 parts of adipic acid, 22 parts of terephthalic acid, 12 parts of trimellitic anhydride, 46 parts of n-octanol and 3 parts of a catalyst are selected as main materials.
After the components and the preparation method are adopted, the invention has the following advantages:
through adopting the adipic acid that cold resistance is strong, n-octanol, the trimellitic anhydride that the heat resistance is strong to take the good terephthalic acid of plastification effect as the base material through reation kettle high temperature reaction back stable in structure, thereby make plastification effect, cold-resistant effect, heat-resisting effect obtain comparatively obvious promotion in PVC hard material.
Detailed Description
The present invention is described in further detail below.
Example one
An improved dioctyl adipate preparation method comprises the steps of feeding 8 parts of adipic acid, 8 parts of terephthalic acid, 8 parts of trimellitic anhydride, 0.5 part of catalyst and 64 parts of n-octanol into a reaction kettle, filling nitrogen, raising the temperature to 120 ℃ by using steam, raising the temperature to 180 ℃ by using heat conduction oil, adding a proper amount of tetraisopropyl titanate, raising the temperature to 180 ℃, esterifying for 15 hours under normal pressure, closing the nitrogen, cooling by using a condenser, adding a proper amount of liquid caustic soda diluted by using water IV to one into the reaction kettle, vacuumizing, replenishing water and dealcoholizing for three hours, reducing the temperature to 110, adding a proper amount of liquid caustic diluted by using water IV to one into the reaction kettle, neutralizing, dehydrating for one hour to obtain an improved dioctyl adipate crude product, and pressurizing by using a filter circulating pump until diatomite and activated carbon are filtered and decolored to obtain a finished product.
Wherein the catalyst is tetraisopropyl titanate.
The specific operation is as follows: when a certain amount of octanol is put into the reaction kettle, a stirrer in the reaction kettle is opened, the octanol is stirred at a low speed, adipic acid is continuously put into the reaction kettle, and then terephthalic acid and trimellitic anhydride are delivered into the reaction kettle. The liquid alkali selected in the preparation process is sodium hydroxide solution. Because octanol is flammable, smoke and fire are avoided during the production process.
Then, after adding sodium hydroxide and diluting, starting to inject nitrogen into the reaction kettle, introducing steam into the reaction kettle to heat up, when the temperature rises to 120 ℃, heating by using heat conduction oil, and stopping heating when the temperature reaches 180 ℃.
Example two
An improved dioctyl adipate preparation method comprises the steps of feeding 12 parts of adipic acid, 12 parts of terephthalic acid, 12 parts of trimellitic anhydride, 5.5 parts of catalyst and 76 parts of n-octanol into a reaction kettle, filling nitrogen, raising the temperature to 120 ℃ by using steam, raising the temperature to 180 ℃ by using heat conduction oil, adding a proper amount of tetraisopropyl titanate, raising the temperature to 210 ℃, esterifying for 20 hours under normal pressure, closing the nitrogen, cooling by using a condenser, adding a proper amount of liquid caustic soda diluted by using water IV to one into the reaction kettle, vacuumizing, replenishing water and dealcoholizing for three hours, reducing the temperature to 110, adding a proper amount of liquid caustic diluted by using water IV to one into the reaction kettle, neutralizing, dehydrating for one hour to obtain an improved dioctyl adipate crude product, and pressurizing by using a filter circulating pump until diatomite and activated carbon are filtered and decolored to obtain a finished product.
EXAMPLE III
An improved dioctyl adipate preparation method comprises the steps of feeding 10 parts of adipic acid, 10 parts of terephthalic acid, 10 parts of trimellitic anhydride, 5 parts of catalyst and 70 parts of n-octanol into a reaction kettle, filling nitrogen, raising the temperature to 120 ℃ by using steam, raising the temperature to 180 ℃ by using heat conduction oil, adding an appropriate amount of tetraisopropyl titanate, raising the temperature to 200 ℃, esterifying for 18 hours under normal pressure, closing the nitrogen, cooling by using a condenser, adding an appropriate amount of liquid caustic soda diluted by using water IV to one into the reaction kettle, vacuumizing, replenishing water and dealcoholizing for three hours, reducing the temperature to 110, adding an appropriate amount of liquid caustic diluted by using water IV to one into the reaction kettle, neutralizing, dehydrating for one hour to obtain an improved dioctyl adipate crude product, and pressurizing by using a circulating pump until diatomite and activated carbon are filtered and decolored to obtain a finished product.
Claims (5)
1. An improved preparation method of dioctyl adipate is characterized in that, during specific preparation, feeding 8-12 parts of adipic acid, 8-12 parts of terephthalic acid, 8-12 parts of trimellitic anhydride, 0.5-5.5 parts of catalyst and 64-76 parts of n-octanol into a reaction kettle, introducing nitrogen, heating to 120 ℃ by using steam, heating to 180 ℃ by using heat transfer oil, adding a proper amount of tetraisopropyl titanate, heating to 210 ℃ by using 180 ℃, esterifying for 15-20 hours under normal pressure, closing the nitrogen, cooling by using a condenser, adding a proper amount of liquid caustic soda diluted by using water IV to one into the reaction kettle, vacuumizing, supplementing water and dealcoholizing for three hours, after the temperature is reduced to 110 ℃, adding a proper amount of aqueous alkali diluted by four times to one for neutralization, dehydrating for one hour to obtain an improved dioctyl adipate crude product, and pressurizing by using a filter circulating pump until diatomite and active carbon are filtered and decolored to obtain a finished product.
2. The improved dioctyl adipate as recited in claim 1, wherein said catalyst is tetraisopropyl titanate.
3. The improved preparation method of dioctyl adipate as claimed in claim 1, wherein the main materials selected in the concrete preparation process comprise 12 parts of adipic acid, 12 parts of terephthalic acid, 12 parts of trimellitic anhydride, 5.5 parts of catalyst and 76 parts of n-octanol.
4. The improved preparation method of dioctyl adipate as claimed in claim 1, wherein 8 parts of adipic acid, 8 parts of terephthalic acid, 8 parts of trimellitic anhydride, 0.5 part of catalyst and 64 parts of n-octanol are selected as main materials during specific preparation.
5. The improved preparation method of dioctyl adipate as claimed in claim 1, wherein during specific preparation, 10 parts of adipic acid, 10 parts of terephthalic acid, 10 parts of trimellitic anhydride, 5 parts of catalyst and 70 parts of n-octanol are selected as main materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911109992.0A CN111040246A (en) | 2019-11-14 | 2019-11-14 | Improved preparation method of dioctyl adipate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911109992.0A CN111040246A (en) | 2019-11-14 | 2019-11-14 | Improved preparation method of dioctyl adipate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111040246A true CN111040246A (en) | 2020-04-21 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911109992.0A Pending CN111040246A (en) | 2019-11-14 | 2019-11-14 | Improved preparation method of dioctyl adipate |
Country Status (1)
| Country | Link |
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| CN (1) | CN111040246A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1636962A (en) * | 2003-03-26 | 2005-07-13 | 蒋平平 | Production method of multi-variety low-consumption plasticizer |
| CN101993548A (en) * | 2010-09-30 | 2011-03-30 | 浙江嘉澳环保科技股份有限公司 | Environment-friendly composite plasticizer and preparation method |
| EP2810932A1 (en) * | 2013-06-06 | 2014-12-10 | ExxonMobil Chemical Patents Inc. | Improvements in or relating to plasticiser esters |
| CN105504347A (en) * | 2015-12-11 | 2016-04-20 | 安徽律正科技信息服务有限公司 | Light-resistant, heat-resistant and anti-aging plasticizer for plastics |
| CN106795324A (en) * | 2014-10-09 | 2017-05-31 | 巴斯夫欧洲公司 | The plasticizer composition of cycloalkyl ester and terephthalate comprising saturated dicarboxylic acid |
| CN108129316A (en) * | 2017-12-25 | 2018-06-08 | 江苏雷蒙新材料有限公司 | A kind of nylon acid two（2- ethyls）The preparation method of own ester |
-
2019
- 2019-11-14 CN CN201911109992.0A patent/CN111040246A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1636962A (en) * | 2003-03-26 | 2005-07-13 | 蒋平平 | Production method of multi-variety low-consumption plasticizer |
| CN101993548A (en) * | 2010-09-30 | 2011-03-30 | 浙江嘉澳环保科技股份有限公司 | Environment-friendly composite plasticizer and preparation method |
| EP2810932A1 (en) * | 2013-06-06 | 2014-12-10 | ExxonMobil Chemical Patents Inc. | Improvements in or relating to plasticiser esters |
| CN106795324A (en) * | 2014-10-09 | 2017-05-31 | 巴斯夫欧洲公司 | The plasticizer composition of cycloalkyl ester and terephthalate comprising saturated dicarboxylic acid |
| CN105504347A (en) * | 2015-12-11 | 2016-04-20 | 安徽律正科技信息服务有限公司 | Light-resistant, heat-resistant and anti-aging plasticizer for plastics |
| CN108129316A (en) * | 2017-12-25 | 2018-06-08 | 江苏雷蒙新材料有限公司 | A kind of nylon acid two（2- ethyls）The preparation method of own ester |
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| PB01 | Publication | ||
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| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20200421 |
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| RJ01 | Rejection of invention patent application after publication |