CN116265044A - Method for treating paraxylene liquid phase oxidation residues - Google Patents
Method for treating paraxylene liquid phase oxidation residues Download PDFInfo
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- CN116265044A CN116265044A CN202111540796.6A CN202111540796A CN116265044A CN 116265044 A CN116265044 A CN 116265044A CN 202111540796 A CN202111540796 A CN 202111540796A CN 116265044 A CN116265044 A CN 116265044A
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- 238000000034 method Methods 0.000 title claims abstract description 30
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 230000003647 oxidation Effects 0.000 title claims abstract description 21
- 238000007254 oxidation reaction Methods 0.000 title claims abstract description 21
- 239000007791 liquid phase Substances 0.000 title claims abstract description 11
- 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 34
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 claims abstract description 23
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 239000002253 acid Substances 0.000 claims abstract description 6
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005711 Benzoic acid Substances 0.000 claims abstract description 5
- 235000010233 benzoic acid Nutrition 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 8
- UJMDYLWCYJJYMO-UHFFFAOYSA-N benzene-1,2,3-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1C(O)=O UJMDYLWCYJJYMO-UHFFFAOYSA-N 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims 6
- 238000004064 recycling Methods 0.000 abstract description 2
- 239000002440 industrial waste Substances 0.000 abstract 1
- 239000002910 solid waste Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- -1 terephthalic acid Chemical compound 0.000 description 7
- 238000003756 stirring Methods 0.000 description 6
- 239000012153 distilled water Substances 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 230000001699 photocatalysis Effects 0.000 description 2
- 239000003643 water by type Substances 0.000 description 2
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 238000006385 ozonation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/10—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by subjecting to electric or wave energy or particle or ionizing radiation
- A62D3/17—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by subjecting to electric or wave energy or particle or ionizing radiation to electromagnetic radiation, e.g. emitted by a laser
- A62D3/176—Ultraviolet radiations, i.e. radiation having a wavelength of about 3nm to 400nm
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D3/00—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances
- A62D3/30—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents
- A62D3/38—Processes for making harmful chemical substances harmless or less harmful, by effecting a chemical change in the substances by reacting with chemical agents by oxidation; by combustion
-
- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2101/00—Harmful chemical substances made harmless, or less harmful, by effecting chemical change
- A62D2101/20—Organic substances
- A62D2101/28—Organic substances containing oxygen, sulfur, selenium or tellurium, i.e. chalcogen
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- A—HUMAN NECESSITIES
- A62—LIFE-SAVING; FIRE-FIGHTING
- A62D—CHEMICAL MEANS FOR EXTINGUISHING FIRES OR FOR COMBATING OR PROTECTING AGAINST HARMFUL CHEMICAL AGENTS; CHEMICAL MATERIALS FOR USE IN BREATHING APPARATUS
- A62D2203/00—Aspects of processes for making harmful chemical substances harmless, or less harmful, by effecting chemical change in the substances
- A62D2203/02—Combined processes involving two or more distinct steps covered by groups A62D3/10 - A62D3/40
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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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Business, Economics & Management (AREA)
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Abstract
The application discloses a method for treating paraxylene liquid phase oxidation residues, which comprises the steps of adopting ultraviolet light to catalyze ozone oxidation, and carrying out oxidation treatment on the residues of terephthalic acid to obtain products containing benzoic acid, paradibenzoic acid and trimellitic acid. The method has the characteristics of simple and convenient operation and mild conditions, comprehensively utilizes the paraxylene liquid-phase oxidation residues, greatly reduces the discharge of solid wastes, and realizes the recycling of industrial waste residues.
Description
Technical Field
The application relates to a method for treating paraxylene liquid phase oxidation residues, and belongs to the field of chemistry and chemical engineering.
Background
Terephthalic Acid (PTA) is an important bulk organic chemical raw material, and is mainly obtained by oxidizing Paraxylene (PX) through a Co-Mn-Br three-way catalyst at present. China is one of the largest PTA production processes in the world, and the productivity exceeds 7000 ten thousand tons. In the process of preparing terephthalic acid by liquid-phase oxidation of paraxylene and in the process of preparing refined terephthalic acid by refining crude terephthalic acid, a large amount of residues are generated, and the solid residues have high acidity, so that the treatment methods such as direct landfill and the like cause serious environmental pollution, and the improvement is necessary. The components of the solid residues are complex, the content of each component also greatly varies along with the fluctuation of the oxidation conditions, and the solid residues are difficult to treat by a common method. The solid residues are burnt directly, which is caused by high acid value, compact accumulation and the like, so that the combustion is insufficient, and a large amount of pollution is generated in the burning process.
The main component of the residue of terephthalic acid is aromatic acid such as terephthalic acid, and products such as p-methylbenzyl alcohol after hydrorefining and polycyclic aromatic acid generated at high temperature are also included. If the pure terephthalic acid can be fully converted into aromatic acid by adopting a proper oxidation method for recycling, the economic benefit of the PTA device can be improved while the environmental protection treatment pressure is reduced. The development of a gentle and efficient oxidation process is therefore critical to this path.
Disclosure of Invention
Aiming at the problems of poor environmental protection and poor economic benefit of the traditional treatment method of oxidation residues generated in the reaction of preparing terephthalic acid by o-xylene liquid phase oxidation, the invention provides a method for treating the p-xylene liquid phase oxidation residues, which utilizes a photocatalytic ozone oxidation method.
In one aspect of the present application, a method for treating a liquid phase oxidation residue of paraxylene is provided, wherein the method comprises the steps of performing ultraviolet light catalytic ozonation, and performing oxidation treatment on the residue of terephthalic acid to obtain a product containing benzoic acid, paradibenzoic acid and trimellitic acid.
Optionally, the method specifically includes: mixing the residue of terephthalic acid with water to form a mixture, introducing air containing ozone, starting ultraviolet light, and reacting to obtain the products containing benzoic acid, paradibenzoic acid and benzene tricarboxylic acid.
As a specific embodiment, the method comprises:
dispersing a certain amount of solid residues in water, stirring to form uniform suspension, introducing ozone air with a certain concentration, starting ultraviolet light, stirring for a certain time, and reacting. After the reaction was completed, the resultant was centrifuged and analyzed.
Optionally, the ultraviolet light ranges from 190 nm to 390nm, and the optical power ranges from 200 mw/cm to 1000mw/cm 2 。
Optionally, the concentration of ozone in the air containing ozone is 10-50 ppm;
alternatively, the upper limit of ozone concentration may be independently selected from 20ppm, 30ppm, 40ppm, 50ppm; the lower limit may be independently selected from 10ppm, 20ppm, 30ppm, 40ppm;
alternatively, the ratio of the flow rate of ozone-containing air to the mixture is 100 to 600ml/min gas flow rate of 1L of mixture.
Optionally, the mass ratio of the residue of terephthalic acid to water is 1:1-10.
Alternatively, the upper mass ratio of the terephthalic acid residue to water can be independently selected from 1:1, 2:3, 1:2, 1:4, 1:6, 1:8; the lower limit may be independently selected from 2:3, 1:2, 1:4, 1:6, 1:8, 1:10;
optionally, the reaction temperature is 25-40 ℃ and the reaction time is 1-8 h.
Alternatively, the upper reaction temperature limit may be independently selected from 30 ℃, 40 ℃; the lower limit can be independently selected from 25deg.C and 30deg.C;
alternatively, the upper reaction time limit may be independently selected from 2h, 5h, 8h, 10h; the lower limit can be independently selected from 1h, 2h, 5h and 8h;
alternatively, the reaction is carried out in a quartz glass reactor.
The beneficial effects that this application can produce include:
the solid residue treated by the method is mostly converted into recyclable aromatic acid products, especially polycyclic aromatic compounds in the reaction process, and the polycyclic aromatic compounds are subjected to ring opening oxidation into aromatic acid under the double actions of photocatalysis and ozone, and finally the yield of the obtained aromatic acid (the yield of liquid chromatography) can reach more than 90%. The method has the advantages of mild conditions, high yield and the like, and can obviously improve the catalytic effect of the reaction.
Drawings
FIG. 1 is a schematic diagram of a reaction apparatus.
FIG. 2 analysis conditions and typical product chromatograms.
Detailed Description
The present application is described in detail below with reference to examples, but the present application is not limited to these examples.
Unless otherwise indicated, all starting materials in the examples of the present application were purchased commercially.
The methods and apparatus employed in the examples of the present application for analysis of the products are as follows:
instrument: liquid phase Waters 2695 detector: refractive index detector Waters 2414
Chromatographic column: shodex Asashipak NH 2P-50E 4E
Mobile phase: acetonitrile: water = 8:2 flow rate: 1mL/min column box temperature: 25 ℃ detector temperature: 35 DEG C
Example 1
Weighing 100g of paraxylene oxidized solid residues, adding 200g of distilled water, stirring and dispersing to obtain a uniform suspension, introducing air containing ozone, wherein the concentration of ozone is 10ppm, the flow rate is 40ml/min, starting an ultraviolet lamp, the wavelength is 255nm, the power is 300w, the reaction temperature is maintained at 30 ℃, the reaction is maintained for 5 hours, centrifuging is performed after the reaction is finished, and an oxidized product is collected. And (5) drying and collecting 90g of oxidized residues. A portion of the extract was analyzed by high performance liquid chromatography. The distribution of the product is as follows:
| benzoic acid | Phthalic acid | Benzene tricarboxylic acid | Benzene tetra-carboxylic acid |
| 15.8％ | 70.1％ | 5.2％ | 3.2％ |
Example 2
200g of ortho-xylene oxidized solid residues are weighed, 300g of distilled water is added, stirring and dispersing are carried out until the mixture is uniform, air containing ozone is introduced, the ozone concentration is 40ppm, the flow rate is 80ml/min, an ultraviolet lamp is started, the wavelength is 365nm, the power is 800w, the reaction temperature is maintained at 40 ℃, the reaction is maintained for 8 hours, and after the reaction is finished, the mixture is centrifuged, and oxidized products are collected. And (5) drying and collecting 172g of oxidized residues. A portion of the extract was analyzed by high performance liquid chromatography. The distribution of the product is as follows:
| benzoic acid | Phthalic acid | Benzene tricarboxylic acid | Benzene tetra-carboxylic acid |
| 20.8％ | 65.1％ | 4.2％ | 1.2％ |
Example 3
Weighing 100g of ortho-xylene oxidized solid residues, adding 400g of distilled water, stirring and dispersing to obtain a uniform suspension, introducing air containing ozone, wherein the ozone concentration is 20ppm, the flow rate is 80ml/min, starting an ultraviolet lamp, the wavelength is 255nm, the power is 900w, the reaction temperature is maintained at 25 ℃, the reaction is maintained for 1h, centrifuging is performed after the reaction is finished, and an oxidized product is collected. And (5) drying and collecting 90g of oxidized residues. A portion of the extract was analyzed by high performance liquid chromatography. The distribution of the product is as follows:
| benzoic acid | Phthalic acid | Benzene tricarboxylic acid | Benzene tetra-carboxylic acid |
| 18.8％ | 66.2％ | 3.2％ | 0.8％ |
Example 4
Weighing 100g of ortho-xylene oxidized solid residues, adding 200g of distilled water, stirring and dispersing to obtain a uniform suspension, introducing air containing ozone, wherein the ozone concentration is 10ppm, the flow rate is 40ml/min, starting an ultraviolet lamp with the wavelength of 356nm and the power of 300w, maintaining the reaction temperature at 40 ℃, maintaining the reaction for 5h, centrifuging after the reaction is finished, and collecting an oxidized product. And (5) drying and collecting 90g of oxidized residues. A portion of the extract was analyzed by high performance liquid chromatography. The distribution of the product is as follows:
| benzoic acid | Phthalic acid | Benzene tricarboxylic acid | Benzene tetra-carboxylic acid |
| 6.8％ | 71.1％ | 9.2％ | 8.2％ |
The foregoing description is only a few examples of the present application and is not intended to limit the present application in any way, and although the present application is disclosed in the preferred examples, it is not intended to limit the present application, and any person skilled in the art may make some changes or modifications to the disclosed technology without departing from the scope of the technical solution of the present application, and the technical solution is equivalent to the equivalent embodiments.
Claims (7)
1. A method for treating paraxylene liquid phase oxidation residue is characterized in that ultraviolet light is adopted to catalyze ozone oxidation, and the residue of terephthalic acid is subjected to oxidation treatment to obtain a product containing benzoic acid, paradibenzoic acid and trimellitic acid.
2. The method of claim 1, wherein the step of determining the position of the substrate comprises,
the method specifically comprises the following steps: mixing the residue of terephthalic acid with water to form a mixture, introducing air containing ozone, starting ultraviolet light to irradiate the air containing ozone, and reacting to obtain the products containing benzoic acid, p-dibenzoic acid and benzene tricarboxylic acid.
3. The method of claim 1, wherein the step of determining the position of the substrate comprises,
the ultraviolet light is 190-390 nm and the light power is 200-ultra1000mw/cm 2 。
4. The method of claim 2, wherein the step of determining the position of the substrate comprises,
in the air containing ozone, the concentration of ozone is 10-50 ppm;
the ratio of the flow rate of the air containing ozone to the mixture is 100-600 ml/min gas flow rate and 1L of mixture.
5. The method of claim 2, wherein the step of determining the position of the substrate comprises,
the mass ratio of the residue of terephthalic acid to water is 1:1-10.
6. The method of claim 2, wherein the step of determining the position of the substrate comprises,
the reaction temperature is 25-40 ℃ and the reaction time is 1-8 h.
7. The method of claim 2, wherein the step of determining the position of the substrate comprises,
the reaction is carried out in a quartz glass reactor.
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