CN114057537A - Catalytic hydrogenation dechlorination method for polychlorinated benzene - Google Patents
Catalytic hydrogenation dechlorination method for polychlorinated benzene Download PDFInfo
- Publication number
- CN114057537A CN114057537A CN202010782933.6A CN202010782933A CN114057537A CN 114057537 A CN114057537 A CN 114057537A CN 202010782933 A CN202010782933 A CN 202010782933A CN 114057537 A CN114057537 A CN 114057537A
- Authority
- CN
- China
- Prior art keywords
- benzene
- polychlorinated
- catalytic
- percent
- toluene
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000006298 dechlorination reaction Methods 0.000 title claims description 12
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims description 8
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 110
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 72
- 239000003054 catalyst Substances 0.000 claims abstract description 35
- 150000001555 benzenes Chemical class 0.000 claims abstract description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 21
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 21
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 239000007789 gas Substances 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 230000003197 catalytic effect Effects 0.000 claims description 16
- 239000007791 liquid phase Substances 0.000 claims description 14
- 150000008422 chlorobenzenes Chemical class 0.000 claims description 2
- 239000002245 particle Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 238000000926 separation method Methods 0.000 abstract description 3
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 13
- GBDZXPJXOMHESU-UHFFFAOYSA-N 1,2,3,4-tetrachlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1Cl GBDZXPJXOMHESU-UHFFFAOYSA-N 0.000 description 11
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 11
- 239000002994 raw material Substances 0.000 description 11
- JHBKHLUZVFWLAG-UHFFFAOYSA-N 1,2,4,5-tetrachlorobenzene Chemical compound ClC1=CC(Cl)=C(Cl)C=C1Cl JHBKHLUZVFWLAG-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- 238000004364 calculation method Methods 0.000 description 10
- 238000005070 sampling Methods 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 8
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- 229940117389 dichlorobenzene Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000003915 air pollution Methods 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a method for comprehensively utilizing mixed polychlorinated benzene, which takes methylbenzene as a solvent, palladium-carbon as a catalyst and a fixed bed as a reactor, and the mixed polychlorinated benzene hydrogenation catalyst is dechlorinated to generate benzene and hydrogen chloride, wherein the conversion rate of the polychlorinated benzene is 100%, the product is single, the separation is easy, and the process flow is simple and easy to operate.
Description
Technical Field
The invention relates to chlorobenzene and a production process of downstream products thereof, belonging to the field of pesticides and fine chemical engineering.
Background
During the production of chlorobenzene or dichlorobenzene by catalytic chlorination of benzene, polychlorinated chlorobenzene byproducts are inevitably generated, wherein trichlorobenzene, tetrachlorobenzene and the like are included, 1,2, 4-trichlorobenzene in the polychlorinated benzene has multiple purposes after purification, and the polychlorinated benzene with other structures has small use and small market demand.
Therefore, the polychlorinated benzene is accumulated more and more in production, not only pollutes the environment, but also occupies the field, and becomes a great burden for the production of chlorobenzene industry.
The current method for treating waste containing chlorine and hydrocarbon is incineration method, which generates a large amount of hydrogen chloride to cause air pollution and generates new harmful substances when the combustion is incomplete.
Therefore, the comprehensive treatment method of polychlorinated benzene is continuously researched and explored.
The polychlorinated benzene can be subjected to hydrogenolysis dechlorination under the action of a hydrogenation catalyst to generate low-chlorine aromatic hydrocarbon, benzene or cyclohexane. That is, the mixed polychlorinated benzene can be chemically treated to obtain a product with use value.
The catalytic hydrodechlorination of polychlorinated benzene published in environmental protection of chemical industry by Liuguang Yong, Guo Hongyu and Liu Xiu Feng is carried out by using Al3O2The experiment result of the catalyst which is a carrier and Pt as an active component and is used for performing the hydrogenation dechlorination reaction of the polychlorinated benzene on a micro-reaction chromatographic device shows that the catalyst is suitable for the dechlorination of the polychlorinated benzene, and the liquid airspeed is 2-3 at the temperature of 300-350 ℃ and the liquid airspeed-1h. Pressure 0.8M Pa, hydrogen molar ratio 2: 1-3: 1, the dechlorination rate of the polychlorobenzene is 50%, the conversion rate is 80%, and the yield of chlorobenzene and dichlorobenzene is more than 40%.
Traditional polychlorinated benzene catalytic hydrogenation is carried out in a kettle type reactor, an acid binding agent needs to be added, a large amount of salt-containing wastewater can be produced in the reaction, in addition, the kettle type reactor is slow in mass and heat transfer, the reaction temperature and the concentration are not uniform, the catalyst needs to be filtered and separated, the loss is large, the yield is low, the quality stability of batch products is poor, and the reaction process is difficult to accurately control.
Disclosure of Invention
The purpose of the invention is as follows: based on the fact that products of benzene, chlorobenzene and dichlorobenzene after traditional hydrodechlorination are required to be separated, the invention develops a more efficient catalytic hydrodechlorination production method, and the polychlorinated benzene is subjected to catalytic hydrodechlorination to directly generate benzene and hydrogen chloride, so that the benzene generated after the polychlorinated benzene is subjected to hydrodechlorination can be reused in chlorobenzene production, and benzene consumption in chlorobenzene production is reduced.
The method takes methylbenzene as a solvent, 5% palladium carbon as a catalyst and a fixed bed as a reactor, the mixed polychlorinated benzene is subjected to hydrogenation catalytic dechlorination to generate benzene and hydrogen chloride, a product and a hydrogen mixture are subjected to gas-liquid separation, gas is dehydrated and eluted to remove hydrogen chloride gas, and the product after the mixed polychlorinated benzene is subjected to catalytic hydrogenation dechlorination is benzene and hydrogen chloride.
The invention content is as follows: the method comprises the steps of taking methylbenzene as a solvent, taking 0.5% palladium carbon as a catalyst, taking a fixed bed as a reactor, and carrying out hydrogenation catalytic dechlorination on mixed polychlorinated benzene to generate benzene and hydrogen chloride. Cooling the other parts after hydrodechlorination to separate toluene and benzene, and washing the gas phase to remove hydrogen chloride gas.
Toluene is used as a solvent, and 0.5% palladium carbon is used as a catalyst.
The molar ratio of the hydrogen to the liquid phase raw material is 6: 1-10: 1.
The addition amount of the toluene is 15-20% of the weight of the polychlorobenzene.
The temperature of the catalyst bed layer of the fixed bed hydrogenation reactor is 230-280 ℃.
The pressure of the catalytic hydrogenation reaction is 0.2 Mpa-0.6 Mpa.
The feeding airspeed of the liquid-phase material is 0.3h-1~0.6h-1。
The 0.5% palladium carbon catalyst has a particle size of 20-40 mesh.
Advantageous effects
The invention realizes the catalytic hydrogenation dechlorination of the mixed polychlorinated benzene by changing a catalyst system and a reactor and optimizing process conditions, the conversion rate of the polychlorinated benzene is 100 percent, the products are benzene and hydrogen chloride, and the recycling of the polychlorinated benzene in the production process of the chlorobenzene is realized.
Detailed Description
The technical solution of the present invention is further illustrated by the following examples.
Example 1
A fixed bed reactor, a 40-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 15 percent (weight percentage), and the feeding airspeed is controlled to be 0.3h-1The molar ratio of hydrogen to liquid phase raw material is 6:1, the temperature of catalyst bed layer is 230 deg.C, pressure is 0.2Mpa, cooling gas-liquid separation is carried out on product and hydrogen mixture to obtain mixture of benzene and tolueneAnd removing water from the gas, eluting and removing hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 2
A fixed bed reactor, a 20-mesh 0.5% palladium carbon catalyst loading of 10mL, and mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 15 percent (weight percentage), and the feeding airspeed is controlled to be 0.5h-1The molar ratio of hydrogen to liquid phase raw material is 10:1, the temperature of catalyst bed is 280 deg.C, pressure is 0.8Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 3
A fixed bed reactor, a 40-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 20 percent (weight percentage), and the feeding airspeed is controlled to be 0.4h-1The molar ratio of hydrogen to liquid phase raw material is 8:1, the temperature of catalyst bed is 260 deg.C, pressure is 0.6Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 4
A fixed bed reactor, a 30-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are evenly mixed, wherein the toluene accounts for 20 percent (weight percentage), and the feeding airspeed is controlled to be 0.6h-1The molar ratio of hydrogen to liquid phase raw material is 10:1, the temperature of catalyst bed is 270 deg.C, pressure is 0.6Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 5
Fixed bed reactorThe loading of a 30-mesh 0.5% palladium-carbon catalyst is 10mL, and the mixed chlorobenzene comprises the following components in percentage by weight: 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 15 percent (weight percentage), and the feeding airspeed is controlled to be 0.4h-1The molar ratio of hydrogen to liquid phase raw material is 9:1, the temperature of catalyst bed is 260 deg.C, pressure is 0.6Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 6
A fixed bed reactor, a 40-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are evenly mixed, wherein the toluene accounts for 18 percent (weight percentage), and the feeding airspeed is controlled to be 0.3h-1The mol ratio of hydrogen to liquid phase raw material is 7:1, the temperature of catalyst bed is 265 deg.C, pressure is 0.5Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 7
A fixed bed reactor, a 40-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 18 percent (weight percentage), and the feeding airspeed is controlled to be 0.4h-1The molar ratio of hydrogen to liquid phase raw material is 7:1, the temperature of catalyst bed is 275 deg.C, pressure is 0.6Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 8
A fixed bed reactor, a 40-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are mixed evenly, whereinToluene accounts for 20 percent (weight percentage), and the feeding airspeed is controlled to be 0.3h-1The molar ratio of hydrogen to liquid phase raw material is 10:1, the temperature of catalyst bed is 280 deg.C, pressure is 0.2Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 9
A fixed bed reactor, a 20-mesh 0.5% palladium carbon catalyst loading of 10mL, and mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 20 percent (weight percentage), and the feeding airspeed is controlled to be 0.3h-1The molar ratio of hydrogen to liquid phase raw material is 10:1, the temperature of catalyst bed is 230 deg.C, pressure is 0.6Mpa, the mixture of product and hydrogen is cooled and gas-liquid separated to obtain the mixture of benzene and toluene, and the gas is dewatered and eluted to remove hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Example 10
A fixed bed reactor, a 30-mesh 0.5% palladium carbon catalyst loading of 10mL, and a mixed chlorobenzene composition (weight percent): 52 percent of 1,2, 3-trichlorobenzene, 15 percent of 1,2,4, 5-tetrachlorobenzene, 33 percent of 1,2,3, 4-tetrachlorobenzene, and toluene and polychlorobenzene are uniformly mixed, wherein the toluene accounts for 20 percent (weight percentage), and the feeding airspeed is controlled to be 0.4h-1The molar ratio of hydrogen to liquid phase raw material is 7:1, the temperature of catalyst bed is 240 ℃, the pressure is 0.3Mpa, the mixture of product and hydrogen is cooled and separated by gas-liquid to obtain the mixture of benzene and toluene, and the gas is dehydrated and eluted to remove the hydrogen chloride gas. Sampling analysis and calculation show that the conversion rate of the polychlorobenzene is 100 percent.
Claims (10)
1. A catalytic hydrogenation dechlorination method for polychlorinated benzene is characterized by comprising the following steps: the method comprises the steps of taking methylbenzene as a solvent, palladium-carbon as a catalyst and a fixed bed as a reactor, and carrying out hydrogenation catalytic dechlorination on mixed polychlorinated benzene to generate benzene and hydrogen chloride.
2. The catalytic hydrodechlorination process of polychlorobenzene as claimed in claim 1 wherein the product is cooled to separate the hydrogen gas mixture into a mixture of benzene and toluene, and the gas is washed with water to remove hydrogen chloride.
3. The catalytic hydrodechlorination process of polychlorinated benzenes according to claim 1, characterized by a polychlorinated chlorobenzene conversion rate of 100%.
4. The catalytic hydrodechlorination process of polychlorinated benzene as claimed in claim 1, wherein toluene is used as solvent and 0.5% palladium on carbon is used as catalyst.
5. The catalytic hydrodechlorination process of polychlorinated benzene as claimed in claim 1, wherein the molar ratio of hydrogen to liquid phase feedstock is 6:1 to 10: 1.
6. The catalytic hydrodechlorination process of polychlorinated benzene as claimed in claim 1, wherein toluene is added in an amount of 18% to 20% by weight of the polychlorinated benzene.
7. The catalytic hydrodechlorination process of polychlorinated benzenes according to claim 1, wherein the fixed bed hydrogenation reactor bed temperature ranges from 230 ℃ to 280 ℃.
8. The catalytic hydrodechlorination process of polychlorobenzene according to claim 1, wherein the pressure of the catalytic hydrogenation reaction is 0.2MPa to 0.6 MPa.
9. The catalytic hydrodechlorination process of polychlorobenzene as claimed in claim 1, wherein the liquid phase feed has a space velocity of 0.6-1~1.0-1。
10. The catalytic hydrodechlorination process of polychlorinated benzene as claimed in claim 2, wherein the particle size of the 0.5% palladium on carbon catalyst is 20-40 mesh.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010782933.6A CN114057537B (en) | 2020-08-06 | 2020-08-06 | Method for catalyzing, hydrogenating and dechlorinating polychlorinated chlorobenzene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010782933.6A CN114057537B (en) | 2020-08-06 | 2020-08-06 | Method for catalyzing, hydrogenating and dechlorinating polychlorinated chlorobenzene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114057537A true CN114057537A (en) | 2022-02-18 |
| CN114057537B CN114057537B (en) | 2024-02-09 |
Family
ID=80232525
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010782933.6A Active CN114057537B (en) | 2020-08-06 | 2020-08-06 | Method for catalyzing, hydrogenating and dechlorinating polychlorinated chlorobenzene |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN114057537B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115646484A (en) * | 2022-08-18 | 2023-01-31 | 扬州博克莱生物医药科技有限公司 | Supported palladium-carbon catalyst for liquid-phase continuous hydrogenolysis dechlorination and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101348420A (en) * | 2008-09-12 | 2009-01-21 | 湖南利洁生物化工有限公司 | Hydrogenation dehalogenation method of halogenated alkyl phenol coumpound |
| CN110204418A (en) * | 2019-06-04 | 2019-09-06 | 江苏扬农化工集团有限公司 | A kind of method of highly effective hydrogenation dechlorination purification trichloro-benzenes |
| CN111187138A (en) * | 2020-01-21 | 2020-05-22 | 江苏扬农化工集团有限公司 | Method for treating dichlorobenzene rectification residue |
| CN111233621A (en) * | 2020-01-21 | 2020-06-05 | 江苏扬农化工集团有限公司 | Dichlorobenzene rectification residue treatment method |
-
2020
- 2020-08-06 CN CN202010782933.6A patent/CN114057537B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101348420A (en) * | 2008-09-12 | 2009-01-21 | 湖南利洁生物化工有限公司 | Hydrogenation dehalogenation method of halogenated alkyl phenol coumpound |
| CN110204418A (en) * | 2019-06-04 | 2019-09-06 | 江苏扬农化工集团有限公司 | A kind of method of highly effective hydrogenation dechlorination purification trichloro-benzenes |
| CN111187138A (en) * | 2020-01-21 | 2020-05-22 | 江苏扬农化工集团有限公司 | Method for treating dichlorobenzene rectification residue |
| CN111233621A (en) * | 2020-01-21 | 2020-06-05 | 江苏扬农化工集团有限公司 | Dichlorobenzene rectification residue treatment method |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115646484A (en) * | 2022-08-18 | 2023-01-31 | 扬州博克莱生物医药科技有限公司 | Supported palladium-carbon catalyst for liquid-phase continuous hydrogenolysis dechlorination and preparation method thereof |
| CN115646484B (en) * | 2022-08-18 | 2024-02-20 | 扬州博克莱生物医药科技有限公司 | Supported palladium-carbon catalyst for liquid phase continuous hydrogenolysis dechlorination and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN114057537B (en) | 2024-02-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113402395B (en) | Method for continuously and efficiently synthesizing m-phenylenediamine based on fixed bed microreactor | |
| CN113429295B (en) | Method for preparing m-phenylenediamine by continuous catalytic hydrogenation based on fixed bed microreactor | |
| CN110105220B (en) | Method for preparing m-phenylenediamine from meta-oil | |
| US7176333B2 (en) | Process for preparing 4-aminodiphenylamine | |
| CN114057537B (en) | Method for catalyzing, hydrogenating and dechlorinating polychlorinated chlorobenzene | |
| CN1680225A (en) | Method and apparatus for preparing isolongifolene from longifolene | |
| CN108584978B (en) | Preparation method of A-type molecular sieve capable of removing pollutants | |
| CN107619375A (en) | A kind of method for continuously synthesizing of high-purity p-phenylenediamine | |
| CN108014806B (en) | Method for preparing wet catalytic oxidation catalyst by using waste catalytic cracking catalyst | |
| US2772313A (en) | Reduction of meta chloro nitrobenzene to meta chloro aniline | |
| CN108114728B (en) | Method for preparing wet catalytic oxidation catalyst by using waste catalytic cracking catalyst | |
| CN111233621B (en) | Dichlorobenzene rectification residue treatment method | |
| CN111187138B (en) | Method for treating dichlorobenzene rectification residue | |
| CN108114726B (en) | Method for preparing wet catalytic oxidation catalyst by using waste catalytic cracking catalyst | |
| CN108218712A (en) | A kind of preparation method of meta nitro aniline | |
| CN113600201A (en) | Preparation method and application of aniline catalyst prepared by nitrobenzene liquid-phase hydrogenation | |
| CN108218659A (en) | Rich advanced alkynes solvent reclamation utilizes method in gas by partial oxidation of natural acetylene technique | |
| CN103240129B (en) | Photocatalyst for synthesizing o-(p-)benzenediol, and synthetic method for o-(p-)benzenediol | |
| CN1462650A (en) | Preparation method of carbon molecular sieve | |
| CN106831318B (en) | Method for catalyzing 2, 5-dichlorotoluene reaction by modified H-type molecular sieve | |
| Sassykova | Catalytic reduction of aromatic nitro compounds: general questions, equipment, enlarged laboratory tests | |
| Luo et al. | Carbon microsphere and NH4Cl recovery from a real pharmaceutical intermediate wastewater through wet oxidation | |
| CN111621318B (en) | Method and device for producing sealing oil | |
| JP2007291039A (en) | Method for producing benzene compound and method for processing plastic material | |
| RU2337904C2 (en) | Low-temperature method for aniline through hydrogenation of nitrobenzene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address | ||
| CP03 | Change of name, title or address |
Address after: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Patentee after: CHINA PETROLEUM & CHEMICAL Corp. Country or region after: China Patentee after: SINOPEC NANJING CHEMICAL RESEARCH INSTITUTE Co.,Ltd. Address before: Liuhe District of Nanjing City, Jiangsu province 210048 geguan Road No. 699 Patentee before: SINOPEC NANJING CHEMICAL RESEARCH INSTITUTE Co.,Ltd. Country or region before: China Patentee before: CHINA PETROLEUM & CHEMICAL Corp. |