CN110372504B - Method for producing polybasic acid ester by recovering light components from side product of meta-anhydride - Google Patents
Method for producing polybasic acid ester by recovering light components from side product of meta-anhydride Download PDFInfo
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- CN110372504B CN110372504B CN201910758566.3A CN201910758566A CN110372504B CN 110372504 B CN110372504 B CN 110372504B CN 201910758566 A CN201910758566 A CN 201910758566A CN 110372504 B CN110372504 B CN 110372504B
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- 150000002148 esters Chemical class 0.000 title claims abstract description 28
- 150000007519 polyprotic acids Polymers 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 13
- 239000006227 byproduct Substances 0.000 title claims abstract description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 50
- 238000010438 heat treatment Methods 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 25
- 239000002253 acid Substances 0.000 claims abstract description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000005886 esterification reaction Methods 0.000 claims abstract description 15
- BWDBEAQIHAEVLV-UHFFFAOYSA-N 6-methylheptan-1-ol Chemical compound CC(C)CCCCCO BWDBEAQIHAEVLV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 230000032050 esterification Effects 0.000 claims abstract description 9
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 9
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000008234 soft water Substances 0.000 claims abstract description 9
- 238000001514 detection method Methods 0.000 claims abstract description 8
- 239000012535 impurity Substances 0.000 claims abstract description 7
- 238000002156 mixing Methods 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims description 29
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 22
- 238000005070 sampling Methods 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 17
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- 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 description 16
- 239000000047 product Substances 0.000 claims description 15
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 239000012295 chemical reaction liquid Substances 0.000 claims description 6
- -1 dicarboxylic acid ester Chemical class 0.000 claims description 6
- 230000003472 neutralizing effect Effects 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 239000004014 plasticizer Substances 0.000 abstract description 13
- 238000005259 measurement Methods 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 230000007797 corrosion Effects 0.000 abstract description 2
- 238000005260 corrosion Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 230000035484 reaction time Effects 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 230000002194 synthesizing effect Effects 0.000 abstract description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 4
- 238000012545 processing Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000005591 trimellitate group Chemical group 0.000 description 2
- 239000000654 additive Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 238000003809 water extraction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the technical field of organic compound preparation, and particularly discloses a method for producing polybasic acid ester by recovering light components from a by-product of metanhydride, which comprises the steps of introducing nitrogen into a reaction kettle, mixing crushed metanhydride light component residues and isooctyl alcohol serving as reaction raw materials, and adding activated carbon and soft water; and then carrying out initial heating, reaction, acid measurement, negative pressure dealcoholization, neutralization treatment, negative pressure impurity removal and detection. The method for synthesizing the polybasic acid ester plasticizer comprises the steps of esterification, acid measurement and neutralization, dealcoholization, low-boiling-point substance removal and the like, and the obtained plasticizer has the characteristics of light color and high quality, and is low in acid value and low in water content; meanwhile, the operation process flow is short, simple and feasible, no corrosion is caused to equipment, the reaction time is short, and the method is environment-friendly, safe and easy for industrial production.
Description
Technical Field
The invention belongs to the technical field of organic compound preparation, and particularly relates to a method for producing polybasic acid ester by recovering light components from a side product of meta-anhydride, which is a synthetic route of polybasic acid anhydride in refined residue of the meta-anhydride and relates to a preparation method of mixed polybasic acid ester plasticizer synthesized by esterification of light component residue at the top of a rectifying tower of the meta-anhydride and polyhydric alcohol.
Background
Plasticizers are polymeric additives that are widely used in industry. The plasticizer is used in plastic processing, and can modify or soften the plastic and increase the plasticity, flexibility, stretchability or expansibility and the like of the plastic. At present, the plasticizer industry has been developed into a plasticizer based on petrochemical industry and taking phthalate as a core, which is widely applied to the plastic and paint industries. However, the phthalate-containing plastic products can cause the dissolution of phthalate and have certain harm in the processes of processing, heating, packaging and containing.
The trimellitate plasticizer has a plurality of excellent performances such as compatibility, electrical property, plasticizing performance, low-temperature performance, migration resistance, water extraction resistance, thermal stability and the like, and the plasticizing efficiency and the processing performance are similar to those of phthalate plasticizers. The product is widely used for 105 ℃ and 125 ℃ heat-resistant wire and cable materials, automotive interior materials and other products requiring heat resistance and durability, such as plates, sheets, gaskets and the like.
Therefore, research and development of more trimellitate plasticizers with excellent performance have very important significance in the future plastic manufacturing industry.
Disclosure of Invention
The invention aims to provide a method for producing polybasic acid ester by recycling light components from a by-product of partial anhydride, which is used for producing a mixed polybasic acid ester plasticizer with better performance indexes such as acid value, heating decrement, resistivity and the like, and has simple process flow and low raw material cost.
In order to solve the technical problem, the invention provides a method for producing polybasic acid ester by recovering light components from a side product of meta-anhydride, which comprises the following steps:
s1, a feeding stage: introducing nitrogen into a reaction kettle, mixing the crushed light-component metaanhydride residue and isooctanol serving as reaction raw materials, and adding active carbon and soft water;
s2, an initial heating stage: heating to 120-130 ℃, stirring and refluxing for 1.5h to completely dissolve polybasic acid anhydride in isooctyl alcohol;
s3, reaction stage: heating to 160-180 ℃ within 10-30 minutes, adding tetraisopropyl titanate, stirring at constant temperature for reflux reaction for 1-1.5h, and simultaneously separating out water generated in the esterification process;
s4, sampling and detecting acidity: taking the reaction liquid for acid ester detection, and finishing the esterification reaction when the acid value is less than 0.1 percent;
s5, negative pressure dealcoholization: closing octanol reflux, carrying out negative pressure dealcoholization, continuously heating to 210-215 ℃, keeping the temperature unchanged, and refluxing for 1.5-2.5 h;
s6, cooling and neutralizing treatment: after dealcoholization is finished, introducing nitrogen, cooling to 90 ℃ under normal pressure, adding a sodium carbonate solution, and stirring for 0.5h;
s7, negative pressure impurity removal: after neutralization, stopping introducing nitrogen, vacuumizing, heating to 150-160 ℃, and removing the mixed ester and the dicarboxylic acid ester in the reaction system under negative pressure for 1.5 hours;
s8, sampling and detecting: and then stopping vacuumizing, introducing nitrogen, stopping heating when the system is recovered to the normal pressure state, starting cooling, sampling, and detecting the index of the product.
Furthermore, the activated carbon in the S1 accounts for 0.3-0.8% of the light component, and the soft water accounts for 0.1-0.15% of the light component.
Specifically, the tetraisopropyl titanate in S3 accounts for 0.05-0.15% of the light component.
Further, the reflux amount of octanol in S3 is 8-10m 3 /h。
Furthermore, the sodium carbonate solution in S6 accounts for 0.05-0.1% of the light components.
Furthermore, the indexes of the product in S8 are that the chroma is less than or equal to 40, the acid value (calculated by KOH)/(mg/g) is less than or equal to 0.15, the volume resistivity/(109 omega. M) is more than or equal to 10, and the water content is less than or equal to 0.1 percent.
The beneficial effects of the invention are: the method for synthesizing the polybasic acid ester plasticizer comprises the steps of esterification, acid measurement and neutralization, dealcoholization, low-boiling-point substance removal and the like, and the obtained plasticizer has the characteristics of light color and high quality, and is low in acid value and low in water content; meanwhile, the operation process flow is short, simple and feasible, no corrosion is caused to equipment, the reaction time is short, and the method is environment-friendly, safe and easy for industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
In the embodiment of the invention, the method for producing the polybasic acid ester by recovering the light components by using the side product of the metaanhydride specifically comprises the following steps:
s1, a feeding stage: introducing nitrogen into a reaction kettle, mixing crushed light-component metaanhydride residues and isooctyl alcohol serving as reaction raw materials, wherein the molar ratio is 1:3 to 4.5, simultaneously adding active carbon accounting for 0.3 to 0.8 percent of the light component and soft water accounting for 0.1 to 0.15 percent of the light component;
s2, an initial heating stage: heating to 120-130 ℃, stirring and refluxing for 1.5h to completely dissolve the polybasic acid anhydride in the isooctyl alcohol;
s3, a reaction stage: heating to 160-180 ℃ within 10-30 minutes, adding tetraisopropyl titanate accounting for 0.05-0.15% of the light component, and controlling the reflux of octanol to 8-10m 3 Stirring at constant temperature for reflux reaction for 1-1.5h, and simultaneously separating out water generated in the esterification process;
s4, sampling and detecting acidity: taking the reaction liquid for acid ester detection, and finishing the esterification reaction when the acid value is less than 0.1 percent;
s5, negative pressure dealcoholization: closing octanol reflux, carrying out negative pressure dealcoholization, continuously heating to 210-215 ℃, keeping the temperature unchanged, and refluxing for 1.5-2.5 h;
s6, cooling and neutralizing treatment: after the dealcoholization is finished, introducing nitrogen, reducing the temperature to 90 ℃ under normal pressure, adding 0.05-0.1% of sodium carbonate solution, and stirring for about 0.5h;
s7, negative pressure impurity removal: after neutralization, stopping introducing nitrogen, vacuumizing, heating to 150-160 ℃, and removing the mixed ester and the dicarboxylic acid ester in the reaction system under negative pressure for 1.5 hours;
s8, sampling and detecting: stopping vacuumizing, introducing nitrogen, stopping heating when the system is recovered to the normal pressure state, starting cooling, sampling, and detecting the index of the product, wherein the index of the product is that the chromaticity is less than or equal to 40; the acid value (calculated by KOH)/(mg/g) is less than or equal to 0.15; the volume resistivity/(109 omega. M) is more than or equal to 10; the water content is less than or equal to 0.1 percent.
Example one
(1) A feeding stage: introducing nitrogen into a reaction kettle, taking crushed light-component metaanhydride residues and isooctyl alcohol as reaction raw materials, and reacting according to the weight ratio of 1:3, and simultaneously adding activated carbon accounting for 0.3 percent of the light component and soft water accounting for 0.1 percent of the light component;
(2) An initial heating stage: heating to 120-130 ℃, stirring and refluxing for 1.5h to completely dissolve the polybasic acid anhydride in the isooctyl alcohol;
(3) A reaction stage: heating to 160-180 ℃ within 10-30 minutes, adding tetraisopropyl titanate accounting for 0.05 percent of the light component, and controlling the reflux quantity of octanol to be 8-10m 3 Stirring at constant temperature for reflux reaction for 1-1.5h, and simultaneously separating out water generated in the esterification process;
(4) Sampling and detecting acidity: taking the reaction liquid for acid ester detection, and finishing the esterification reaction when the acid value is less than 0.1 percent;
(5) Negative pressure dealcoholization: closing octanol reflux, carrying out negative pressure dealcoholization, continuously heating to 210-215 ℃, keeping the temperature unchanged, and refluxing for 1.5-2.5 h;
(6) Cooling and neutralizing treatment stage: after dealcoholization is finished, introducing nitrogen, cooling to 90 ℃ under normal pressure, adding 0.05 sodium carbonate solution, and stirring for about 0.5h;
(7) Negative pressure impurity removal: after neutralization, stopping introducing nitrogen, vacuumizing, heating to 150-160 ℃, and removing the mixed ester and the dicarboxylic acid ester in the reaction system under negative pressure for 1.5 hours;
(8) Sampling and detecting: and then stopping vacuumizing, introducing nitrogen, stopping heating when the system is recovered to the normal pressure state, starting cooling, sampling, and detecting the indexes of the product, wherein the indexes of the obtained product are 35% of chroma, 0.08% of acid value, 12.4% of resistivity and 0.034% of moisture.
Example two
(1) A feeding stage: introducing nitrogen into a reaction kettle, taking crushed light-component metaanhydride residues and isooctanol as reaction raw materials, and mixing the raw materials according to the proportion of 1:4, simultaneously adding activated carbon accounting for 0.5 percent of the light component and soft water accounting for 0.12 percent of the light component;
(2) An initial heating stage: heating to 120-130 ℃, stirring and refluxing for 1.5h to completely dissolve the polybasic acid anhydride in the isooctyl alcohol;
(3) A reaction stage: heating to 160-180 ℃ within 10-30 minutes, adding tetraisopropyl titanate accounting for 0.1 percent of the light component, and controlling the reflux quantity of octanol to be 8-10m 3 Stirring at constant temperature for reflux reaction for 1-1.5h, and simultaneously separating out water generated in the esterification process;
(4) Sampling and detecting acidity: taking the reaction liquid for acid ester detection, and completing the esterification reaction when the acid value is less than 0.1%;
(5) Negative pressure dealcoholization: closing octanol reflux, carrying out negative pressure dealcoholization, continuously heating to 210-215 ℃, keeping the temperature unchanged, and refluxing for 1.5-2.5 h;
(6) Cooling and neutralizing treatment stage: after the dealcoholization is finished, introducing nitrogen, cooling to 90 ℃ under normal pressure, adding 0.08% sodium carbonate solution, and stirring for about 0.5h;
(7) Negative pressure impurity removal: after neutralization, stopping introducing nitrogen, vacuumizing, heating to 150-160 ℃, and removing the mixed ester and the dicarboxylic acid ester in the reaction system under negative pressure for 1.5 hours;
(8) Sampling and detecting: and then stopping vacuumizing, introducing nitrogen, stopping heating when the system is recovered to the normal pressure state, starting cooling, sampling, and detecting the indexes of the product, wherein the indexes of the obtained product are 30% of chroma, 0.051 of acid value, 14.6% of resistivity and 0.025% of moisture.
EXAMPLE III
(1) A feeding stage: introducing nitrogen into a reaction kettle, taking crushed light-component metaanhydride residues and isooctyl alcohol as reaction raw materials, and reacting according to the weight ratio of 1:4.5, and simultaneously adding activated carbon accounting for 0.8 percent of the light component and soft water accounting for 0.15 percent of the light component;
(2) An initial heating stage: heating to 120-130 ℃, stirring and refluxing for 1.5h to completely dissolve the polybasic acid anhydride in the isooctyl alcohol;
(3) A reaction stage: heating to 160-180 ℃ within 10-30 minutes, adding tetraisopropyl titanate accounting for 0.15 percent of the light component, and controlling the reflux amount of octanol to 8-10m 3 H, stirring at constant temperatureReflux reaction is carried out for 1-1.5h, and water generated in the esterification process is separated out;
(4) Sampling and detecting acidity: taking the reaction liquid for acid ester detection, and finishing the esterification reaction when the acid value is less than 0.1 percent;
(5) Negative pressure dealcoholization: closing octanol reflux, carrying out negative pressure dealcoholization, continuously heating to 210-215 ℃, keeping the temperature unchanged, and refluxing for 1.5-2.5 h;
(6) Cooling and neutralizing treatment stage: after the dealcoholization is finished, introducing nitrogen, cooling to 90 ℃ under normal pressure, adding 0.1% sodium carbonate solution, and stirring for about 0.5h;
(7) Negative pressure impurity removal: after neutralization, stopping introducing nitrogen, vacuumizing, heating to 150-160 ℃, and removing the mixed ester and the dicarboxylic acid ester in the reaction system under negative pressure for 1.5 hours;
(8) Sampling and detecting: and then stopping vacuumizing, introducing nitrogen, stopping heating when the system is recovered to the normal pressure state, starting cooling, sampling, and detecting the indexes of the product, wherein the indexes of the obtained product are 30% of chroma, 0.03% of acid value, 16.89% of resistivity and 0.02% of moisture.
The above disclosure is only one preferred embodiment of the present invention, and certainly should not be construed as limiting the scope of the invention, which is defined by the claims and their equivalents.
Claims (5)
1. A method for producing polybasic acid ester by using light components recovered from a by-product of partial anhydride is characterized by comprising the following steps:
s1, feeding: introducing nitrogen into a reaction kettle, mixing crushed light-component metaanhydride residue and isooctanol serving as reaction raw materials, and simultaneously adding activated carbon and soft water, wherein the activated carbon accounts for 0.3-0.8% of the light components, and the soft water accounts for 0.1-0.15% of the light components;
s2, an initial heating stage: heating to 120-130 ℃, stirring and refluxing for 1.5h to completely dissolve the polybasic acid anhydride in the isooctyl alcohol;
s3, reaction stage: heating to 160-180 ℃ within 10-30 minutes, adding tetraisopropyl titanate, stirring at constant temperature for reflux reaction for 1-1.5h, and simultaneously separating out water generated in the esterification process;
s4, sampling and detecting acidity stage: taking the reaction liquid for acid ester detection, and completing the esterification reaction when the acid value is less than 0.1%;
s5, a negative pressure dealcoholization stage: closing octanol reflux, carrying out negative pressure dealcoholization, continuously heating to 210-215 ℃, keeping the temperature unchanged, and refluxing for 1.5-2.5 h;
s6, cooling and neutralizing treatment: after dealcoholization is finished, introducing nitrogen, cooling to 90 ℃ under normal pressure, adding a sodium carbonate solution, and stirring for 0.5h;
s7, negative pressure impurity removal stage: after neutralization, stopping introducing nitrogen, vacuumizing, heating to 150-160 ℃, and removing the mixed ester and the dicarboxylic acid ester in the reaction system under negative pressure for 1.5 hours;
s8, sampling detection: and then stopping vacuumizing, introducing nitrogen, stopping heating when the system is recovered to the normal pressure state, starting cooling, sampling, and detecting the index of the product.
2. The method for producing polybasic acid esters from light components recovered as by-products of partial anhydride according to claim 1, wherein the tetraisopropyl titanate in S3 is 0.05 to 0.15% of the light components.
3. The method for producing polybasic acid ester by using light components recovered from by-product of metaanhydride as claimed in claim 1, wherein the reflux amount of isooctanol in S3 is 8-10m 3 /h。
4. The method for producing polybasic acid esters using a light component recovered as a by-product of a partial anhydride according to claim 1, wherein the sodium carbonate solution in S6 is 0.05 to 0.1% of the light component.
5. The method for producing polybasic acid ester by using the light component recovered from the by-product of the partial anhydride as claimed in claim 1, wherein the index chroma of the product in S8 is less than or equal to 40, and the volume resistivity/(10) 9 Omega m) is more than or equal to 10, and the water content is less than or equal to 0.1 percent.
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