CN111517940A - Method for co-producing m-methylbenzoic acid in production of isophthalic acid - Google Patents
Method for co-producing m-methylbenzoic acid in production of isophthalic acid Download PDFInfo
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- CN111517940A CN111517940A CN202010459284.6A CN202010459284A CN111517940A CN 111517940 A CN111517940 A CN 111517940A CN 202010459284 A CN202010459284 A CN 202010459284A CN 111517940 A CN111517940 A CN 111517940A
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- isophthalic acid
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 title claims abstract description 112
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 title claims abstract description 87
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 40
- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000002994 raw material Substances 0.000 claims abstract description 53
- 239000000463 material Substances 0.000 claims abstract description 41
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 17
- 238000004064 recycling Methods 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 41
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 238000001704 evaporation Methods 0.000 claims description 12
- 230000008020 evaporation Effects 0.000 claims description 8
- 239000002002 slurry Substances 0.000 claims description 8
- 229940011182 cobalt acetate Drugs 0.000 claims description 7
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical group [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 claims description 7
- 229940071125 manganese acetate Drugs 0.000 claims description 7
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 claims description 7
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000004537 pulping Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 239000004615 ingredient Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 239000010409 thin film Substances 0.000 claims description 3
- 159000000021 acetate salts Chemical class 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000002699 waste material Substances 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- 238000005516 engineering process Methods 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000007613 environmental effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000005416 organic matter Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/21—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen
- C07C51/255—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting
- C07C51/265—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with molecular oxygen of compounds containing six-membered aromatic rings without ring-splitting having alkyl side chains which are oxidised to carboxyl groups
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for producing m-methylbenzoic acid in an isophthalic acid factory, which is closely combined with the isophthalic acid factory, all raw materials and auxiliary materials come from raw material and auxiliary material storage units or related units of the isophthalic acid factory, catalytic oxidation reaction is carried out after proportioning, unconsumed raw materials and byproducts can return to an isophthalic acid production device for recycling after reaction, a catalyst returns to related units such as a catalyst recycling unit for recycling, waste environment-friendly treatment is integrated into a related environment-friendly treatment unit of the isophthalic acid factory, public works depend on an internal system of the isophthalic acid factory, and energy is comprehensively utilized while unconsumed materials are recycled. Different from the prior m-toluic acid production technology, the method overcomes the defects of low m-toluic acid production yield, high consumption of raw materials, solvents and catalysts, complicated environmental-protection treatment and the like by closely combining with an m-phthalic acid factory, and provides a novel m-toluic acid production mode.
Description
Technical Field
The invention relates to a production method of m-toluic acid, in particular to a method for co-producing m-toluic acid in the production of m-phthalic acid.
Background
The m-toluic acid is a chemical product with higher value, and the demand of the m-toluic acid is rapidly increased at present. It can be used for organic synthesis intermediates, medical high-efficiency mosquito repellent, agricultural herbicide, perfume, film and chromatographic material. The m-methyl benzoic acid is produced industrially mainly by the air oxidation method of m-xylene. However, the method has the disadvantages of low production yield, high consumption of raw materials, solvents and catalysts, and complicated environmental-friendly treatment.
The production of isophthalic acid is that the isophthalic acid is generated by taking m-xylene as a raw material, taking air as an oxygen source and taking acetic acid as a solvent in an acetate catalyst system. The domestic large-scale isophthalic acid production factory has rich production raw material supply and complete related supporting facilities. How to utilize an isophthalic acid production plant to co-produce other chemical products and fully utilize the advantages of rich raw material and auxiliary material supply, perfect public engineering and convenient environmental protection treatment of the isophthalic acid plant, and the problem to be solved in the field is solved.
Therefore, the invention is especially provided.
Disclosure of Invention
The invention aims to provide a method for co-producing m-methylbenzoic acid in the production of isophthalic acid, which fully utilizes the advantages of rich raw material and auxiliary material supply, perfect public engineering and convenient environmental protection treatment of an isophthalic acid factory, improves the production efficiency of products and reduces the production cost.
In order to solve the above problems, an embodiment of the present invention provides a method for co-producing m-toluic acid in the production of isophthalic acid, including the following steps:
(1) mixing the ingredients: raw materials, a catalyst and a solvent required by the production of m-toluic acid are provided by a raw and auxiliary material unit in an isophthalic acid factory, the raw materials, the solvent and the catalyst are sent into a raw material buffer tank according to a certain proportion, the raw materials, the solvent and the catalyst are heated and stirred, and after the mixing is finished, the materials are sent into a reactor; the solvent comprises acetic acid and the catalyst comprises an acetate salt;
(2) and (3) oxidation reaction: in the reactor, the oxidation reaction is carried out under certain pressure and temperature, the tail gas of the oxidation reaction discharged in the reaction process introduces energy into an isophthalic acid feeding unit or other related units utilizing the energy through heat exchange, and acetic acid and m-xylene cooled from the tail gas of the oxidation reaction enter an isophthalic acid factory for recycling;
(3) and (3) evaporation: evaporating the reacted materials to evaporate acetic acid, raw materials, water and the like, introducing energy into an isophthalic acid feeding unit or other related units utilizing the energy through heat exchange of the evaporated gas-phase materials, and feeding the cooled gas-phase materials into an isophthalic acid factory for recycling;
(4) removing the catalyst: adding water into the materials for pulping, wherein at the moment, because the m-methylbenzoic acid has low solubility in water, a large amount of m-methylbenzoic acid is separated out, acetate is dissolved in water, then filtering is carried out, a filter cake is an organic matter such as the m-methylbenzoic acid, a filtrate is an aqueous solution in which the acetate is dissolved, standing and layering are carried out on the filtrate, the layered raw materials and the aqueous solution are respectively returned for treatment, wherein the raw materials are sent to an m-phthalic acid factory for recycling of the raw materials, the aqueous solution in which the acetate is dissolved enters a catalyst recycling unit of the m-phthalic acid factory, and finally the aqueous solution is sent back to an oxidation unit for;
(5) and (3) rectification: after filtering, rectifying the m-toluic acid slurry, wherein light components are removed, introducing the energy into an m-phthalic acid feeding unit or other related units utilizing the energy by utilizing heat exchange, sending the cooled material into an m-phthalic acid factory, and obtaining an m-toluic acid product as a product at the bottom of a rectifying tower;
further, the raw material is m-xylene, the solvent is 60% -100% acetic acid, and the catalyst is cobalt acetate and manganese acetate; the proportion of the m-xylene which is a raw material in the total mass of the solvent and the raw material is 5-60%, the dosage of the cobalt acetate which is a catalyst is 10-10000ppm, and the dosage of the manganese acetate is 10-10000 ppm.
Further, in the step (1), the raw material is heated at 40 to 90 ℃ while being stirred. The raw materials and the catalyst are both dissolved in the solvent, which is beneficial to the transportation of the raw materials and the reaction.
Further, in the step (2), the reaction pressure is controlled to be 0.1-1.8 MPa.G, the reaction temperature is controlled to be 90-180 ℃, and the reaction time is 0.5-10 hours. Under the condition, the method is favorable for obtaining m-methylbenzoic acid with higher purity by reaction.
Further, in the step (3), the evaporation treatment uses a thin film evaporator, and the evaporation temperature is 120-.
Further, in the step (4), the water adding amount of the pulping treatment is 1-60 times of the mass of the materials.
Further, in the step (4), the solid containing the m-toluic acid slurry is separated from residual liquid m-xylene and acetate dissolved in water by using a filter, and then the filtered m-xylene and the aqueous solution dissolved with acetate are subjected to standing layering treatment for 1-5 hours.
Further, in the step (5), the filtered m-methylbenzoic acid slurry is introduced into a rectifying tower, the component temperature of the enriched material at the bottom of the rectifying tower is controlled at 230-290 ℃, the temperature at the top of the rectifying tower is controlled at 180-220 ℃, the reflux ratio is 0-20, so that light components escape from the top of the rectifying tower, the top component directly returns to an isophthalic acid plant, and the m-methylbenzoic acid product is enriched at the bottom of the rectifying tower.
Compared with the prior art, the invention has the following beneficial effects: firstly, the method relies on the production process of an isophthalic acid factory to carry out the coproduction of the m-toluic acid, fully utilizes the advantages of rich raw material and auxiliary material supply, perfect public engineering and convenient environmental protection treatment of the isophthalic acid factory, improves the production efficiency of products, reduces the production cost, and reduces the investment of equipment, matching and the like; secondly, the byproducts, the unconsumed raw materials, the auxiliary materials and the like generated by the method are used as the raw materials of the isophthalic acid reactor for reaction, so that the material waste is avoided, the material consumption of the product production is greatly reduced, and the problem of environmental protection treatment on the partial materials is avoided; finally, the method comprehensively utilizes the energy, and the energy is used by an isophthalic acid factory, so that the energy utilization rate is improved, and unnecessary energy waste is avoided. Different from the prior m-toluic acid production technology, the method overcomes the defects of low m-toluic acid production yield, high consumption of raw materials, solvents and catalysts, complex environmental-friendly treatment and the like by closely combining with an m-phthalic acid factory, and forms a new m-toluic acid production mode.
Drawings
FIG. 1 is a flow chart of a method for co-producing m-toluic acid in the production of isophthalic acid according to an embodiment of the present invention.
Detailed Description
The principles and spirit of the present invention will be described with reference to a number of exemplary embodiments shown in the drawings. It should be understood that these embodiments are described only to enable those skilled in the art to better understand and to implement the present invention, and are not intended to limit the scope of the present invention in any way.
Referring to fig. 1, an embodiment of the present invention provides a method for producing m-toluic acid, which relies on an isophthalic acid production plant to produce m-toluic acid, wherein raw materials and auxiliary materials are supplied by the production plant, m-xylene is used as a raw material, acetic acid is used as a solvent, acetic acid, cobalt acetate and manganese acetate are used as catalysts for oxidation reaction, and then a series of separation and purification treatments are performed to finally produce a product.
As shown in fig. 1, the method comprises the steps of:
(1) mixing the ingredients: the isophthalic acid factory provides a buffer tank for raw materials, solvents and catalysts according to the proportion. Specifically, the raw material, the solvent and the catalyst can be respectively led out from a raw material storage unit or other related units utilizing the energy of an isophthalic acid factory, then the raw material, the solvent and the catalyst are heated and stirred, the heating is carried out at 30-90 ℃, the raw material and the catalyst are completely dissolved in the solvent, the raw material is meta-xylene, the catalyst is cobalt acetate and manganese acetate, and the solvent is acetic acid with the concentration of 60-100%. The raw materials account for 5-60% of the total mass of the solvent and the raw materials, the dosage of the catalyst cobalt acetate is 10-10000ppm, and the dosage of the manganese acetate is 10-10000ppm, and then the mixed materials are sent to a reactor for reaction.
(2) And (3) oxidation reaction: the mixed materials enter a reactor, air is introduced into the reactor, a heat source is introduced from a factory to heat the reactor, the reaction time is controlled to be 0.5-10 hours, the reaction pressure is adjusted to be 0.1-1.8 MPa.G, and the reaction temperature is adjusted to be 90-180 ℃; the energy of the reaction tail gas generated in the reaction process is introduced into an isophthalic acid feeding unit or other relevant units utilizing the energy through heat exchange to achieve the purpose of recycling the energy in the step, and the cooled acetic acid and the cooled meta-xylene enter the isophthalic acid factory feeding unit or a batching unit or a raw material and auxiliary material storage unit and other relevant units for recycling.
(3) And (3) evaporation: the method comprises the steps of adopting a thin film evaporator, utilizing a heat source provided by a factory to evaporate reacted materials, wherein the evaporation temperature is 130-220 ℃, evaporating water, acetic acid, low-boiling-point byproducts, organic matters and the like in the materials after reaction, evaporating the acetic acid, the water and the low-boiling-point organic matters in the materials after reaction, introducing the evaporated materials into an isophthalic acid feeding unit or other units related to the energy utilization through heat exchange, and conveying the cooled materials to the isophthalic acid factory feeding unit or a batching unit or a raw and auxiliary material storage unit and other related units for recycling.
(4) Removing the catalyst: adding water into the evaporated material for pulping, wherein a large amount of m-methylbenzoic acid is separated out due to low solubility, acetate is dissolved in a liquid phase for filtration, a filter cake is an organic matter such as m-methylbenzoic acid, a filtrate is an aqueous solution in which the acetate is dissolved, and then standing and layering are carried out on the filtrate for 1-5 h. And respectively returning the layered raw materials and the aqueous solution to treatment, wherein the raw materials are sent to an isophthalic acid factory for recycling of the raw materials, the aqueous solution in which acetate is dissolved enters a catalyst recycling unit of the isophthalic acid factory, and finally the aqueous solution is sent back to an oxidation unit for use, so that the catalyst is recycled.
(6) And (3) rectification: introducing the filtered m-toluic acid slurry into a rectifying tower, controlling the reflux ratio to be 0-20, controlling the temperature at the bottom of the tower to be 230-290 ℃, controlling the temperature at the top of the tower to be 180-220 ℃, introducing the energy of the filtered m-toluic acid slurry into an m-phthalic acid feeding unit or other related units utilizing the energy by utilizing heat exchange to realize the utilization of the energy not consumed in the step, directly returning the cooled top light component to related units (a feeding unit or a batching unit or a residue processing unit and other related units) of an m-toluic acid production device to realize the recovery and reutilization of the rectified light component, wherein the bottom of the rectifying tower is an m-toluic acid product.
The inventive concept is explained in detail herein using specific examples, which are given only to aid in understanding the core concepts of the invention. It should be understood that any obvious modifications, equivalents and other improvements made by those skilled in the art without departing from the spirit of the present invention are included in the scope of the present invention.
Claims (8)
1. The method for coproducing m-methylbenzoic acid in the production of isophthalic acid is characterized by comprising the following steps:
(1) mixing the ingredients: raw materials, a catalyst and a solvent required by the production of m-toluic acid are provided by a raw and auxiliary material unit in an isophthalic acid factory, the raw materials, the solvent and the catalyst are sent to a raw material buffer tank, the raw materials, the solvent and the catalyst are heated and stirred, and the mixed materials are sent to a reactor; the solvent comprises acetic acid and the catalyst comprises an acetate salt;
(2) and (3) oxidation reaction: the material is oxidized in the reactor, the tail gas of the oxidation reaction discharged in the reaction process introduces energy into an isophthalic acid feeding unit or other relevant units utilizing the energy through heat exchange, and acetic acid and m-xylene cooled from the tail gas of the oxidation reaction enter an isophthalic acid factory for recycling;
(3) and (3) evaporation: evaporating the reacted materials, introducing energy into an isophthalic acid feeding unit or other units related to the energy utilization by the evaporated gas-phase materials through heat exchange, and feeding the cooled gas-phase materials into an isophthalic acid factory for recycling;
(4) removing the catalyst: adding water into the materials for pulping, separating out the m-toluic acid at the moment, dissolving acetate in water, filtering, standing and layering the filtrate, and respectively returning the layered raw materials and the aqueous solution to the treatment, wherein the raw materials are sent to an isophthalic acid factory for recycling of the raw materials, the aqueous solution dissolved with the acetate enters a catalyst recycling unit of the isophthalic acid factory, and is finally sent back to an oxidation unit for use, so that the catalyst is recycled;
(5) and (3) rectification: after filtering, rectifying the m-methylbenzoic acid slurry, wherein light components are separated out, introducing the energy into an m-phthalic acid feeding unit or other related units utilizing the energy by utilizing heat exchange, sending the cooled material into an m-phthalic acid factory, and obtaining an m-methylbenzoic acid product as a product at the bottom of a rectifying tower.
2. The method for coproducing m-methylbenzoic acid in the production of isophthalic acid as claimed in claim 1, wherein the raw material is m-xylene, the solvent is 60% -100% acetic acid, and the catalyst is cobalt acetate and manganese acetate; the proportion of the m-xylene which is a raw material in the total mass of the solvent and the raw material is 5-60%, the dosage of the cobalt acetate which is a catalyst is 10-10000ppm, and the dosage of the manganese acetate is 10-10000 ppm.
3. The method for co-producing m-toluic acid in the production of isophthalic acid according to claim 1, characterized in that in step (1), the raw material is heated at 40-90 ℃ while being stirred; the raw materials and the catalyst are both dissolved in the solvent.
4. The method for co-producing m-toluic acid in the production of isophthalic acid according to claim 1, characterized in that in step (2), the reaction pressure is controlled to be 0.1-1.8 MPa-G, the reaction temperature is controlled to be 90-180 ℃, and the reaction time is 0.5-10 hours.
5. The method for coproducing m-toluic acid in the production of isophthalic acid as recited in claim 1, wherein in step (3), the evaporation treatment uses a thin film evaporator, and the evaporation temperature is 120-200 ℃.
6. The method for coproducing m-toluic acid in the production of isophthalic acid according to claim 1, wherein in the step (4), the amount of water added for pulping is 1-60 times of the mass of the material.
7. The method for co-producing m-toluic acid in the production of isophthalic acid according to claim 1, characterized in that in step (4), the solid containing the m-toluic acid slurry is separated from residual liquid m-xylene and acetate dissolved in water by using a filter, and then the filtered m-xylene and the aqueous solution dissolved with acetate are subjected to standing and layering treatment for 1-5 hours.
8. The method for coproducing m-toluic acid in the production of isophthalic acid as recited in claim 1, wherein in step (5), the filtered m-toluic acid slurry is introduced into a rectification column, the component temperature of the enriched material at the bottom of the rectification column is controlled to 230-290 ℃, the temperature at the top of the rectification column is controlled to 180-220 ℃, the reflux ratio is 0-20, so that the light component escapes from the top of the rectification column, the top component directly returns to the m-toluic acid plant, and the m-toluic acid product is enriched at the bottom of the rectification column.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101177393A (en) * | 2006-11-08 | 2008-05-14 | 扬州市刘氏化工有限公司 | Process for producing methyl benzoic acid by paraxylene |
| CN101318890A (en) * | 2008-07-15 | 2008-12-10 | 中国石油化工股份有限公司 | Method for preparation of mixed benzol dimethanoic acid and benzene acetic acid |
| CN103693772A (en) * | 2013-01-11 | 2014-04-02 | 绍兴汉青环保科技有限公司 | Method for resource comprehensive utilization of PTA refining waste water |
| CN106831393A (en) * | 2015-12-07 | 2017-06-13 | 扬州杰迪生物科技有限公司 | A kind of m-methyl benzoic acid production technology |
-
2020
- 2020-05-27 CN CN202010459284.6A patent/CN111517940A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101177393A (en) * | 2006-11-08 | 2008-05-14 | 扬州市刘氏化工有限公司 | Process for producing methyl benzoic acid by paraxylene |
| CN101318890A (en) * | 2008-07-15 | 2008-12-10 | 中国石油化工股份有限公司 | Method for preparation of mixed benzol dimethanoic acid and benzene acetic acid |
| CN103693772A (en) * | 2013-01-11 | 2014-04-02 | 绍兴汉青环保科技有限公司 | Method for resource comprehensive utilization of PTA refining waste water |
| CN106831393A (en) * | 2015-12-07 | 2017-06-13 | 扬州杰迪生物科技有限公司 | A kind of m-methyl benzoic acid production technology |
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