CN110818559A - Method for recycling trimellitic anhydride rectification mother liquor residues - Google Patents
Method for recycling trimellitic anhydride rectification mother liquor residues Download PDFInfo
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- CN110818559A CN110818559A CN201911172010.2A CN201911172010A CN110818559A CN 110818559 A CN110818559 A CN 110818559A CN 201911172010 A CN201911172010 A CN 201911172010A CN 110818559 A CN110818559 A CN 110818559A
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- trimellitic anhydride
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/889—Manganese, technetium or rhenium
- B01J23/8892—Manganese
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/94—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the iron group metals or copper
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/48—Liquid treating or treating in liquid phase, e.g. dissolved or suspended
- B01J38/60—Liquid treating or treating in liquid phase, e.g. dissolved or suspended using acids
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- 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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- 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
- C07C67/58—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
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- Organic Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract
The invention relates to the technical field of environment-friendly solvents, and particularly discloses a method for recycling trimellitic anhydride rectification mother liquor residues, which comprises the following steps: the trimellitic anhydride residue and alcohol are esterified to obtain crude ester, and the crude ester is dissolved in a certain amount of organic solventDissolving and diluting the mixed ester, extracting with a diluted acid aqueous solution in a certain proportion, extracting cobalt and manganese metal ions in the trimellitic anhydride residue into a water phase for recovery, sequentially washing the organic phase with pure water to be neutral, and rectifying the washed organic phase to remove the solvent to obtain the mixed ester. The mixed ester prepared by the invention has the ester content of more than 99 percent and the volume resistivity of more than 109Omega cm, the method is simple to operate and convenient to produce, and the resource utilization rate is improved.
Description
Technical Field
The invention relates to the technical field of environment-friendly solvents, in particular to a method for recycling trimellitic anhydride rectification mother liquor residues.
Background
The mixed ester prepared from the trimellitic anhydride rectification mother liquor residue and alcohol can be used as a plasticizer, has low volatility, excellent heat resistance, small migration, good electrical insulation, durability, low toxicity, water resistance and proper compatibility, is suitable for plastics such as polyvinyl chloride, vinyl chloride copolymer, cellulose nitrate, ethyl cellulose and the like, and can also be used as heat-resistant wire and cable materials, plates, sheets, gaskets and the like.
The method can separate the metal ions of cobalt and manganese in the trimellitic anhydride rectification mother liquor residue, and the trimellitic anhydride and the homologues thereof are prepared into mixed ester, so that the useful components in the solid waste can be fully recycled, and the solid waste output is reduced.
After examining a large number of documents, no invention report about the recovery of useful components in the trimellitic anhydride rectification mother liquor residue exists at home and abroad at present.
Disclosure of Invention
The invention aims to provide a method for recycling trimellitic anhydride rectification mother liquor residues, which comprises the steps of carrying out esterification reaction on the trimellitic anhydride rectification mother liquor residues and alcohol, diluting by using an organic solvent, extracting by using a dilute acid aqueous solution, washing by using pure water to be neutral, and removing the solvent to obtain an aqueous solution and mixed ester containing cobalt and manganese metal ions, wherein the aqueous solution can be used for recycling catalyst cobalt and manganese metal ions.
In order to solve the technical problems, the invention provides a method for recycling trimellitic anhydride rectification mother liquor residues, which comprises the following steps:
s1, sequentially adding alcohol, trimellitic anhydride residues and a catalyst into an esterification kettle, heating the esterification kettle and stirring, extracting water generated in the esterification process and excessive alcohol added before the reaction to ensure that the acid is completely esterified, and rectifying to remove excessive solvent to obtain crude ester after the reaction is finished after the temperature is increased to 180 ℃ and 250 ℃ and the reaction is carried out for 3.5-10 h;
s2, reducing the temperature of the esterification kettle to room temperature, and diluting the crude ester and the organic solvent in a mass ratio of 1:1-6 to obtain an organic phase;
s3, diluting the organic phase and the dilute acid water according to the mass ratio of 1:1-6, stirring and extracting for 5-60min, standing and layering, separating out the upper organic phase, and continuing to mix the upper organic phase and the dilute acid water according to the mass ratio of 1:1-6 dilution, repeating the extraction operation for 2-4 times, and collecting the lower aqueous phase;
s4, stirring and washing the organic phase and the pure water solution for 5-30min according to the mass ratio of 1:1-6, standing for layering, continuously stirring and washing the separated organic phase and the pure water solution according to the mass ratio of 1:1-6, and repeating the washing operation for 2-4 times to wash the organic phase to be neutral;
s5, rectifying the washed organic phase to remove the solvent to obtain the mixed ester.
Specifically, the alcohol in the S1 is n-butanol and isooctanol.
Specifically, the organic solvent in S2 is one or more of benzene, xylene, cyclohexane, butyl acetate, n-propyl acetate, isopropyl acetate, and ethyl acetate.
Specifically, the dilute acid water solution in S3 is one or more of sulfuric acid, hydrochloric acid, acetic acid, and phosphoric acid, and the concentration of the dilute acid water (in mass percent of the water solution) is 0.1-5%.
Specifically, in S3, the metal ions manganese and cobalt in the aqueous phase are collected.
Specifically, the temperature of the pure water solution in the S4 is 25-50 ℃.
The invention has the beneficial effects that: the mixed ester prepared by the invention has the ester content of more than 99 percent and the volume resistivity of more than 109Omega cm, simple method operation, convenient production and improved resource utilization rate.
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.
Example 1:
adding 2000g of isooctanol, 1000g of trimellitic anhydride residue and 2.5g of catalyst tetraisopropyl titanate into an ester exchange kettle in sequence, stirring and heating to 220 ℃, and reacting for 5 hours; opening vacuum, gradually reducing the temperature of the reaction liquid from 7500Pa to 500Pa, reducing the temperature of the reaction liquid from 220 ℃ to 160 ℃, finishing dealcoholization, continuously reducing the temperature of the reaction liquid to room temperature to obtain mixed ester crude ester, adding 6000g of toluene, stirring and diluting for 0.5h, then adding 6000g of 5% dilute sulfuric acid aqueous solution, stirring and extracting for 30min, standing and layering, separating out a lower-layer aqueous phase, continuously and organically repeating the extraction operation for 3 times, collecting the aqueous phase for recovering cobalt and manganese metal ions, and extracting 93% of cobalt and manganese metal ions into the dilute acid aqueous phase by detection. The organic phase was further added with 6000g of pure water, and washing was repeated 3 times to neutrality. And removing the solvent from the organic phase to obtain the mixed ester. The content of the ester in the mixed ester is 99.16 percent through detection, and the volume resistivity of the mixed ester is more than 109Ω·cm。
Example 2:
adding 2000g of isooctanol, 1000g of trimellitic anhydride residue and 2.5g of catalyst tetraisopropyl titanate into an ester exchange kettle in sequence, and stirringHeating to 220 ℃ and reacting for 5 h; opening vacuum, gradually reducing the temperature of the reaction liquid from 7500Pa to 500Pa, reducing the temperature of the reaction liquid from 220 ℃ to 160 ℃, finishing dealcoholization, continuously reducing the temperature of the reaction liquid to room temperature to obtain mixed ester crude ester, adding 6000g of butyl acetate, stirring and diluting for 0.5h, adding 6000g of 1% dilute sulfuric acid aqueous solution, stirring and extracting for 30min, standing and layering, separating out a lower-layer aqueous phase, continuously and organically repeating the extraction operation for 3 times, collecting the aqueous phase for recovering cobalt and manganese metal ions, and extracting more than 99% of the cobalt and manganese metal ions into the dilute acid aqueous phase by detection. The organic phase was further added with 6000g of pure water, and washing was repeated 3 times to neutrality. And removing the solvent from the organic phase to obtain the mixed ester. The detection shows that the ester content in the mixed ester is 99.32 percent, and the volume resistivity of the mixed ester is more than 109Ω·cm。
Example 3:
adding 2000g of isooctanol, 1000g of trimellitic anhydride residue and 2.5g of catalyst tetraisopropyl titanate into an ester exchange kettle in sequence, stirring and heating to 220 ℃, and reacting for 5 hours; opening vacuum, gradually reducing the temperature of the reaction liquid from 7500Pa to 500Pa, reducing the temperature of the reaction liquid from 220 ℃ to 160 ℃, finishing dealcoholization, continuously reducing the temperature of the reaction liquid to room temperature to obtain crude ester, adding 8000g of cyclohexane, stirring and diluting for 0.5h, then adding 6000g of 3% dilute sulfuric acid aqueous solution, stirring and extracting for 30min, standing and layering, separating a lower-layer aqueous phase, organically and continuously repeating the extraction operation for 3 times, collecting the aqueous phase for recovering cobalt and manganese metal ions, and extracting 95% of cobalt and manganese metal ions into the dilute acid aqueous phase by detection. The organic phase was further added with 6000g of pure water, and washing was repeated 3 times to neutrality. Removing the solvent from the organic phase to obtain mixed ester, wherein the content of the ester in the mixed ester is detected to be 99.22%, and the volume resistivity of the mixed ester is larger than 109Ω·cm。
In the above examples, the content of metal ions extracted into the aqueous phase and the content of ester in the mixed ester were different due to the different solubility of the organic solvent and the different concentration of the dilute acid.
The above disclosure is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the scope of the present invention, therefore, the present invention is not limited by the appended claims.
Claims (6)
1. A method for recycling trimellitic anhydride rectification mother liquor residues is characterized by comprising the following steps:
s1, sequentially adding alcohol, trimellitic anhydride residues and a catalyst into an esterification kettle, heating the esterification kettle and stirring, extracting water and excessive alcohol generated in the esterification process, finishing the reaction after the temperature is increased to 180 ℃ and 250 ℃ and the reaction lasts for 3.5-10h, and removing excessive solvent through rectification to obtain crude ester;
s2, reducing the temperature of the esterification kettle to room temperature, and diluting the crude ester and the organic solvent in a mass ratio of 1:1-6 to obtain an organic phase;
s3, diluting the organic phase and the dilute acid water according to the mass ratio of 1:1-6, stirring and extracting for 5-60min, standing and layering, separating out the upper organic phase, and continuing to mix the upper organic phase and the dilute acid water according to the mass ratio of 1:1-6 dilution, repeating the extraction operation for 2-4 times, and collecting the lower aqueous phase;
s4, stirring and washing the extracted organic phase and the pure water solution for 5-30min according to the mass ratio of 1:1-6, standing for layering, continuously stirring and washing the separated organic phase and the pure water solution according to the mass ratio of 1:1-6, and repeating the washing operation for 2-4 times to wash the organic phase to be neutral;
s5, rectifying the washed organic phase to remove the solvent to obtain the mixed ester.
2. The method for recycling trimellitic anhydride rectification mother liquor residues according to claim 1, characterized in that the alcohol in S1 is n-butanol or isooctanol.
3. The method for recycling trimellitic anhydride rectification mother liquor residues according to claim 1, wherein the organic solvent in S2 is one or more of benzene, xylene, cyclohexane, butyl acetate, n-propyl acetate, isopropyl acetate and ethyl acetate.
4. The method for recycling trimellitic anhydride rectification mother liquor residues according to claim 1, characterized in that the dilute acid aqueous solution in S3 is one or more of sulfuric acid, hydrochloric acid, acetic acid and phosphoric acid, and the concentration of the dilute acid aqueous solution is 0.1-5%.
5. The method for recycling trimellitic anhydride rectification mother liquor residues according to claim 1, wherein metal ions manganese and cobalt in an aqueous phase are collected in S3.
6. The method for recycling trimellitic anhydride rectification mother liquor residues according to claim 1, characterized in that the temperature of the pure water solution in S4 is 25-50 ℃.
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111004374A (en) * | 2019-11-26 | 2020-04-14 | 南通百川新材料有限公司 | Method for preparing alkyd resin based on trimellitic anhydride rectification heavy residual liquid |
CN112521827A (en) * | 2020-11-13 | 2021-03-19 | 南通百川新材料有限公司 | Method for recycling waste residues generated in production process of trimellitic anhydride |
CN113151686A (en) * | 2020-12-08 | 2021-07-23 | 南通百川新材料有限公司 | Equipment and method for recovering cobalt-manganese mixture in trimellitic anhydride production residues |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4298759A (en) * | 1980-12-19 | 1981-11-03 | Standard Oil Company (Indiana) | Separation of cobalt and manganese from trimellitic acid process residue by extraction, ion exchanger and magnet |
US4372875A (en) * | 1979-06-12 | 1983-02-08 | Dynamit Nobel Aktiengesellschaft | Method for obtaining and reusing of oxidation catalyst in the Witten DMT process |
US4410449A (en) * | 1979-12-14 | 1983-10-18 | Dynamit Nobel Aktiengesellschaft | Recovery and reuse of heavy-metal oxidation catalyst from the Witten DMT process |
CN1931850A (en) * | 2006-08-31 | 2007-03-21 | 江阴市百川化学工业有限公司 | Continuous production process of high purity trimellitic anhydride with trimellitic acid |
CN105017022A (en) * | 2015-07-20 | 2015-11-04 | 浙江大学 | Method for methyl esterification recovery and recycle of PTA oxidation residue |
CN106008204A (en) * | 2016-05-31 | 2016-10-12 | 百川化工(如皋)有限公司 | Method for synthesizing trimellitic triesters |
CN108586252A (en) * | 2018-06-21 | 2018-09-28 | 江苏正丹化学工业股份有限公司 | A kind of efficient esterification process of trioctyl trimellitate (TOTM) |
CN109081385A (en) * | 2018-08-15 | 2018-12-25 | 南通百川新材料有限公司 | A kind of method that the recycling of cobalt manganese waste slag prepares ternary material |
CN109776315A (en) * | 2019-01-31 | 2019-05-21 | 浙江大学 | A method of environment-friendly plasticizer dibenzoic diglycol laurate is prepared by Action In The Liquid Phase Oxidation of Xylene residue |
CN110372504A (en) * | 2019-08-16 | 2019-10-25 | 南通百川新材料有限公司 | A method of polybasic ester is produced using inclined acid anhydride by-product recycling lighter component |
-
2019
- 2019-11-26 CN CN201911172010.2A patent/CN110818559A/en active Pending
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4372875A (en) * | 1979-06-12 | 1983-02-08 | Dynamit Nobel Aktiengesellschaft | Method for obtaining and reusing of oxidation catalyst in the Witten DMT process |
US4410449A (en) * | 1979-12-14 | 1983-10-18 | Dynamit Nobel Aktiengesellschaft | Recovery and reuse of heavy-metal oxidation catalyst from the Witten DMT process |
US4298759A (en) * | 1980-12-19 | 1981-11-03 | Standard Oil Company (Indiana) | Separation of cobalt and manganese from trimellitic acid process residue by extraction, ion exchanger and magnet |
CN1931850A (en) * | 2006-08-31 | 2007-03-21 | 江阴市百川化学工业有限公司 | Continuous production process of high purity trimellitic anhydride with trimellitic acid |
CN105017022A (en) * | 2015-07-20 | 2015-11-04 | 浙江大学 | Method for methyl esterification recovery and recycle of PTA oxidation residue |
CN106008204A (en) * | 2016-05-31 | 2016-10-12 | 百川化工(如皋)有限公司 | Method for synthesizing trimellitic triesters |
CN108586252A (en) * | 2018-06-21 | 2018-09-28 | 江苏正丹化学工业股份有限公司 | A kind of efficient esterification process of trioctyl trimellitate (TOTM) |
CN109081385A (en) * | 2018-08-15 | 2018-12-25 | 南通百川新材料有限公司 | A kind of method that the recycling of cobalt manganese waste slag prepares ternary material |
CN109776315A (en) * | 2019-01-31 | 2019-05-21 | 浙江大学 | A method of environment-friendly plasticizer dibenzoic diglycol laurate is prepared by Action In The Liquid Phase Oxidation of Xylene residue |
CN110372504A (en) * | 2019-08-16 | 2019-10-25 | 南通百川新材料有限公司 | A method of polybasic ester is produced using inclined acid anhydride by-product recycling lighter component |
Non-Patent Citations (2)
Title |
---|
包秀秀: "混合芳香羧酸的分离与精制方法研究", 《中国优秀博硕士学位论文全文数据库(硕士)工程科技Ⅰ辑》 * |
程健雄: "从Witten法氧化产物中萃取钴锰催化剂", 《聚酯工业》 * |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN111004374A (en) * | 2019-11-26 | 2020-04-14 | 南通百川新材料有限公司 | Method for preparing alkyd resin based on trimellitic anhydride rectification heavy residual liquid |
CN111004374B (en) * | 2019-11-26 | 2021-09-24 | 南通百川新材料有限公司 | Method for preparing alkyd resin based on trimellitic anhydride rectification heavy residual liquid |
CN112521827A (en) * | 2020-11-13 | 2021-03-19 | 南通百川新材料有限公司 | Method for recycling waste residues generated in production process of trimellitic anhydride |
CN113151686A (en) * | 2020-12-08 | 2021-07-23 | 南通百川新材料有限公司 | Equipment and method for recovering cobalt-manganese mixture in trimellitic anhydride production residues |
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