CN108424355A - A kind of production method and production system of 2,4 dichloro phenol - Google Patents
A kind of production method and production system of 2,4 dichloro phenol Download PDFInfo
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- CN108424355A CN108424355A CN201710076400.4A CN201710076400A CN108424355A CN 108424355 A CN108424355 A CN 108424355A CN 201710076400 A CN201710076400 A CN 201710076400A CN 108424355 A CN108424355 A CN 108424355A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/685—Processes comprising at least two steps in series
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/68—Purification; separation; Use of additives, e.g. for stabilisation
- C07C37/70—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment
- C07C37/74—Purification; separation; Use of additives, e.g. for stabilisation by physical treatment by distillation
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a kind of production systems of 2,4 chlorophenesic acids, including：Fixed bed reactors, the fixed bed reactors include phenol feed inlet, chlorosulfuric acid feed inlet and discharge port, and load type metal saline catalyst is provided in the fixed bed reactors；Extracting tower, the extracting tower include feed inlet, gas discharge mouth and liquid outlet opening, and the feed inlet of the extracting tower is connected with the discharge port of the fixed bed reactors；Rectifying column, the feed inlet of the rectifying column are connected with the liquid outlet opening of the extracting tower.Compared with prior art, load type metal saline catalyst is fixed in fixed bed reactors by production system provided by the invention, continuous use, make phenol with metallic salt catalyst not in a system, impurity is reduced in reaction solution to make chlorination reaction, it is easily isolated purifying, the substance after final rectifying is also made not have solid residue, reaction route clean environment firendly.
Description
Technical field
The invention belongs to chemical technology fields, more particularly to the production method and production system of one kind 2,4- chlorophenesic acids.
Background technology
2,4- chlorophenesic acids be used as solvent, pesticide and medicine intermediate, for synthesize nitrofen, 2,4-D, she compare phosphorus
(EPBP), malicious gram of scattered, Genit and drug bithionol, the tens thousand of tons of annual requirement.
The production method of 2,4 dichloro phenol mainly has：Phenol direct chlorination method, mixed phenol chloridising, o-chlorphenol selection
Five kinds of chloridising, parachlorophenol chloridising and phenol catalytic chlorination process.
Phenol direct chlorination method is domestic and international traditional processing technology, simple process and low cost, but due to wherein by-product
2,6- chlorophenesic acid physical properties with 2,4- chlorophenesic acids due to very close and being difficult to detach causes product purity low, Wu Fasheng
The higher 2,4 dichloro phenol of output purity.
Selective highest and most easy industrializing implementation includes following method in existing report：
For department of chemistry of Shandong University using the by-product o-chlorphenol during industrially producing parachlorophenol as raw material, use is anhydrous
Alchlor and diphenyl sulfide make catalyst, and chlorinating agent is done with chlorosulfuric acid, and chlorination reaction is carried out in 15 ± 2 DEG C of temperature ranges,
For the content of 2,4- chlorophenesic acids up to 95% or more, remaining is 2,6- chlorophenesic acids in product.
Phenol leads to chlorine under iron catalysis, is made in 80 DEG C~100 DEG C chlorinations, but reaction temperature is excessively high.Reaction equation is such as
Under：
The yield of contraposition can be significantly increased according to the presence of data introduction, the presence of copper, especially compound mantoquita.Qingdao
Research institute of Tianyuan chemical inc has carried out the selection of catalyst and reaction condition according to above-mentioned data, has achieved rank
Section property achievement directly synthesizes purity and has reached 94% or so.
The Chinese patent of Publication No. CN105777499A discloses one kind and adding composite catalyst controlled syntheses with chlorosulfuric acid
2,4- chlorophenesic acids and 2, the method for 4,6- trichlorophenol, 2,4,6,-Ts, mention can chlorination obtain 98% 2,4- chlorophenesic acids, but due to
Using expensive chlorosulfuric acid, while necessarily leading to eutectic site catalyst substance and chlorine using Crystallization Separation is melted below
When change in the material mixing to target product of oxidation stain, cause product appearance poor, and contain certain impurity, influences subsequently to make
With there are certain difficulty when making industrializing implementation.
And existing chlorination takes batch tank chlorination more, sampling analysis is needed in chlorination process, while taking dropwise addition sulphur
The mode of acyl chlorides is added dropwise interval, causes outlet unstable, and then cause sulfur dioxide reuse control difficulty big, while metal salt
Catalyst recycling is difficult, and expenses of environmental protection is high.
Invention content
In view of this, the technical problem to be solved in the present invention is to provide production method and the life of one kind 2,4- chlorophenesic acids
Production system, the production system can realize the recycling of catalyst.
The present invention provides the production systems of one kind 2,4- chlorophenesic acids, including：
Fixed bed reactors, the fixed bed reactors include phenol feed inlet, chlorosulfuric acid feed inlet and discharge port, described
Load type metal saline catalyst is provided in fixed bed reactors；
Extracting tower, the extracting tower include feed inlet, gas discharge mouth and liquid outlet opening, the feed inlet of the extracting tower
It is connected with the discharge port of the fixed bed reactors；
Rectifying column, the feed inlet of the rectifying column are connected with the liquid outlet opening of the extracting tower.
Preferably, further include chlorosulfuric acid distributor；The chlorosulfuric acid distributor is set in the fixed bed reactors.
Preferably, the fixed bed reactors are made of the tubulation of Multiple Superposition；It is provided with chlorosulfuric acid between the tubulation
Distributor.
Preferably, the side wall of the fixed bed reactors is provided with shell side heat-exchange system.
Preferably, further include chlorosulfuric acid reactor；The chlorosulfuric acid reactor include tail gas feed inlet, chlorine feed mouth with
Discharge port；The tail gas feed inlet of the chlorosulfuric acid reactor is connected with the gas discharge mouth of the extracting tower；The chlorosulfuric acid
The discharge port of reactor is connected with the chlorosulfuric acid feed inlet of the fixed bed reactors.
The present invention also provides the production methods of one kind 2,4- chlorophenesic acids, including：
Using production system described above；
Phenol is mixed with ethers catalyst, obtains mixed liquor；
The mixed liquor and chlorosulfuric acid are passed through in fixed bed reactors, chlorination reaction is carried out, obtains reaction solution；
By the reaction solution after depickling processing and rectification process, 2,4- chlorophenesic acids are obtained.
Preferably, the ethers catalyst is dipropyl sulfide and/or diphenyl sulfide.
Preferably, the load type metal saline catalyst includes carrier and metal salt；The metal salt be ferric trichloride,
Ferric iodide with it is one or more in ferric bromide；The carrier is polyacrylic acid ion exchange resin or silica dioxide granule.
Preferably, the quality of the ethers catalyst is the 0.01%~0.1% of phenol quality.
Preferably, the temperature of the chlorination reaction is 40 DEG C~100 DEG C；The temperature of the depickling processing is 80 DEG C~120
℃。
The present invention provides the production systems of one kind 2,4- chlorophenesic acids, including：Fixed bed reactors, the fixed bed are anti-
It includes phenol feed inlet, chlorosulfuric acid feed inlet and discharge port to answer device, and load type metal salt is provided in the fixed bed reactors
Class catalyst；Extracting tower, the extracting tower include feed inlet, gas discharge mouth and liquid outlet opening, the charging of the extracting tower
Mouth is connected with the discharge port of the fixed bed reactors；Rectifying column, the liquid of the feed inlet of the rectifying column and the extracting tower
Body discharge port is connected.Compared with prior art, production system provided by the invention fixes load type metal saline catalyst
In in fixed bed reactors, continuous use makes phenol with metallic salt catalyst not in a system, to make chlorination reaction
Reaction solution in impurity reduce, be easily isolated purifying, the substance after final rectifying also made not have a solid residue, reaction route cleans
Environmental protection.
The present invention also provides a kind of methods producing 2,4- chlorophenesic acids using above-mentioned production system, including：By phenol
It is mixed with ethers catalyst, obtains mixed liquor；The mixed liquor and chlorosulfuric acid are passed through in fixed bed reactors, it is anti-to carry out chlorination
It answers, obtains reaction solution；By the reaction solution after depickling processing and rectification process, 2,4- chlorophenesic acids are obtained.With the prior art
It compares, the present invention realizes continuous chlorination in fixed bed reactors, and fixed bed reactors heat exchange area is big, is distributed, simultaneously
By ethers catalyst and load type metal catalyst collective effect, chlorination efficiency is made to improve, product quality is stablized, chlorination temperature
It is not harsh, in addition, product is carried out continuously depickling and rectifying, realize whole contact, high degree of automation, operation degree is low, continuously
Obtain the 2,4 dichloro phenol of high-quality.
Description of the drawings
Fig. 1 is the structural schematic diagram of the production system of 2,4 dichloro phenol provided by the invention.
Specific implementation mode
Below in conjunction with the embodiment of the present invention, technical scheme in the embodiment of the invention is clearly and completely described,
Obviously, described embodiments are only a part of the embodiments of the present invention, instead of all the embodiments.Based in the present invention
Embodiment, every other embodiment obtained by those of ordinary skill in the art without making creative efforts, all
Belong to the scope of protection of the invention.
The present invention provides the production systems of one kind 2,4- chlorophenesic acids, including：Fixed bed reactors, the fixed bed are anti-
It includes phenol feed inlet, chlorosulfuric acid feed inlet and discharge port to answer device, and load type metal salt is provided in the fixed bed reactors
Class catalyst；Extracting tower, the extracting tower include feed inlet, gas discharge mouth and liquid outlet opening, the charging of the extracting tower
Mouth is connected with the discharge port of the fixed bed reactors；Rectifying column, the liquid of the feed inlet of the rectifying column and the extracting tower
Body discharge port is connected.
Fig. 1 is the structural schematic diagram of the production system of 2,4- chlorophenesic acids provided by the invention, wherein 1 is distributed for chlorosulfuric acid
Device, 2 be fixed bed reactors, and 3 be extracting tower.
According to the present invention, the fixed bed reactors are fixed bed reactors well known to those skilled in the art, and
Without special limitation, preferably it is made of the tubulation of Multiple Superposition in the present invention；It is preferably provided with sulphur in the fixed bed reactors
Acyl chlorides distributor can make chlorosulfuric acid be evenly distributed；The chlorosulfuric acid distributor is more preferably set between tubulation in the present invention,
Further preferably acyl chlorides distributor is mutually perpendicular to tubulation, is set between tubulation, to realize contiguous segmentation chlorination.
In the present invention, the side wall of the fixed bed reactors is preferably provided with shell side heat-exchange system；Shell side heat exchange system
Recirculated water is passed through in system to control the temperature of fixed bed reactors.
Fixed bed reactors heat exchange area is big, and distribution is good, it can be achieved that flux reacts greatly, and obtained product quality is stablized,
It is easy to operate, environmentally friendly, safe.
The discharge port of the fixed bed reactors is connected with the feed inlet of the extracting tower；The reaction solution of chlorination reaction connects
The continuous extracting tower that enters realizes that continuous depickling obtains depickling tail gas and depickling liquid after depickling processing.
According to the present invention, the production system preferably further includes acyl chloride reaction device；The chlorosulfuric acid reactor includes tail gas
Feed inlet, chlorine feed mouth and discharge port；The gas discharge of the tail gas feed inlet and the extracting tower of the chlorosulfuric acid reactor
Mouth is connected；The discharge port of the chlorosulfuric acid reactor is connected with the chlorosulfuric acid feed inlet of the fixed bed reactors.Depickling
Tail gas is hydrogen chloride and sulfur dioxide mixture, is continuously passed through in chlorosulfuric acid reactor, and chlorosulfuric acid is generated with chlorine successive reaction,
It is used further to phenol chlorination.
The liquid outlet opening of the extracting tower is connected with the feed inlet of rectifying column.
Continuous depickling and continuous rectification, whole continuous, high degree of automation, and product quality is stablized, operating cost is low.
Load type metal saline catalyst is fixed in fixed bed reactors by production system provided by the invention, is continuously made
With making phenol and metallic salt catalyst not in a system, impurity is reduced in the reaction solution to make chlorination reaction, is easy to
It isolates and purifies, the substance after final rectifying is also made not have solid residue, reaction route clean environment firendly.
The present invention also provides a kind of methods that the above-mentioned production system of application produces 2,4- chlorophenesic acids, including：By phenol
It is mixed with ethers catalyst, obtains mixed liquor；The mixed liquor and chlorosulfuric acid are passed through in fixed bed reactors, it is anti-to carry out chlorination
It answers, obtains reaction solution；By the reaction solution after depickling processing and rectification process, 2,4- chlorophenesic acids are obtained.
Wherein, the present invention is not particularly limited the source of all raw materials, is commercially available.
Phenol is mixed with ethers catalyst, obtains mixed liquor；The ethers catalyst is known to those skilled in the art
Ethers catalyst, have no special limitation, preferably dipropyl sulfide and/or diphenyl sulfide in the present invention；The ethers is urged
The quality of agent is preferably the 0.01%~0.1% of phenol quality.
Mixed liquor and chlorosulfuric acid are passed through fixed bed reactors, preferably according to phenol in mixed liquor and chlorosulfuric acid equimolar amounts
It is passed through in fixed bed reactors；The fixed bed reactors are fixed bed reactors well known to those skilled in the art, and
Without special limitation, preferably its draw ratio is (5~20) in the present invention：1；The mobility of the phenol and chlorosulfuric acid is each independently
Preferably 0.1~1m/s；Load type metal saline catalyst is provided in the fixed bed reactors；The load type metal salt
Catalyst includes carrier and metal salt；The metal salt is preferably one or more in ferric trichloride, ferric iodide and ferric bromide；
The carrier is preferably polyacrylic acid ion exchange resin or silica dioxide granule；The load of the load type metal salt catalyst
Amount preferably 1%~10%, more preferably 1%~8%, is further preferably 2%~5%.Load type metal salt catalyst can be solid
It is persistently used in fixed bed reactor.
According to the present invention, the load type metal salt catalyst is preferably prepared according to the following steps：By dissolving metal salts in
It in alcoholic solvent, is then mixed with carrier, after reflux, removes alcoholic solvent, obtain load type metal salt catalyst；The alcoholic solvent is
Alcoholic solvent well known to those skilled in the art has no special limitation, is preferably methanol in the present invention.
Mixed liquor carries out chlorination reaction with chlorosulfuric acid in fixed bed reactors；The temperature of the chlorination reaction is preferably 40
DEG C~100 DEG C.
Chlorination reaction obtains reaction solution through depickling processing and rectification process；The temperature of depickling processing is preferably 80 DEG C~
120℃；Depickling liquid, by aldehydes matter and ethers catalytic separation, obtains 2,4- chlorophenesic acids in rectifying column；The ethers of separation is urged
Agent, which can continue to mix with phenol, carries out chlorination reaction, realizes the recycling of catalyst.
The present invention realizes continuous chlorination in fixed bed reactors, and fixed bed reactors heat exchange area is big, is distributed, together
When by ethers catalyst and load type metal catalyst collective effect, so that chlorination efficiency is improved, product quality stablize, chlorination temperature
Degree is not harsh, in addition, product is carried out continuously depickling and rectifying, realizes whole contact, high degree of automation, operation degree is low, even
It is continuous to obtain the 2,4 dichloro phenol of high-quality.
In order to further illustrate the present invention, with reference to embodiments to a kind of life of 2,4- chlorophenesic acids provided by the invention
Production method and production system are described in detail.
Reagent used in following embodiment is commercially available.
Embodiment 1
Production system shown in FIG. 1 is provided；The draw ratio of fixed bed reactors is 10, and the flow velocity of phenol is 0.2m/s；Sulphur
The flow velocity of acyl chlorides is 0.1m/s.
1kg ferric trichlorides are dissolved in 100kg methanol, are mixed with 50kg polyacrylic acid ion exchange resin, reflux 5 is small
When, it is dried in vacuo after methanol removal, obtains load type metal salt catalyst.
Load type metal salt catalyst is filled out in the tubulation of ceramic dielectric fixed bed reactors, sulphur is provided between tubulation
Acyl chlorides distributor.
100kg phenol is mixed with 0.01kg dipropyl sulfides, obtains mixed liquor；
Mixed liquor and chlorosulfuric acid are passed through according to the ratio of phenol and chlorosulfuric acid equimolar amounts in fixed bed reactors and carried out
Chlorination reaction, fixed bed reactors are by shell side heat exchanger controlled at 80 DEG C.
Chlorination reaction liquid continuously enters extracting tower, realizes that continuous depickling, depickling tail gas are that hydrogen chloride is mixed with sulfur dioxide
Object is continuously passed through in chlorosulfuric acid reactor, is generated chlorosulfuric acid with chlorine successive reaction, is used further to phenol chlorination, depickling temperature is
80℃。
The depickling liquid of depickling qualification is continuously transferred to rectifying column, and phenol is detached with ethers catalyst.Obtain 2,4- dichloros
Phenol 172.8kg, content 99.8%, yield 99.5%.
In ethers catalyst recycling to phenol chlorination.Realize that catalyst circulation uses.
And the catalyst loaded then persistently uses in fixed bed reactors.
Embodiment 2
The production system being continuing in embodiment 1.
100kg phenol is mixed with 0.1kg diphenyl sulfides, obtains mixed liquor；
Mixed liquor and chlorosulfuric acid are passed through according to the ratio of phenol and chlorosulfuric acid equimolar amounts in fixed bed reactors and carried out
Chlorination reaction, fixed bed reactors are by shell side heat exchanger controlled at 60 DEG C.
Chlorination reaction liquid continuously enters extracting tower, realizes that continuous depickling, depickling tail gas are that hydrogen chloride is mixed with sulfur dioxide
Object is continuously passed through in chlorosulfuric acid reactor, is generated chlorosulfuric acid with chlorine successive reaction, is used further to phenol chlorination, depickling temperature is
80℃。
The depickling liquid of depickling qualification is continuously transferred to rectifying column, and phenol is detached with ethers catalyst, is recycled benzene sulphur
Ether catalyst 0.08kg obtains 2,4- chlorophenesic acid 172.5kg, content 99.7%, yield 99.3%.
Embodiment 3
The diphenyl sulfide 0.08kg recycled in Example 2, adds it in 100kg phenol, is sufficiently mixed.Then should
Mixed liquor and chlorosulfuric acid, which are passed through according to the ratio of phenol and chlorosulfuric acid equimolar amounts in embodiment 2, carries out chlorine in fixed bed reactors
Change reaction, fixed bed reactors are by shell side heat exchanger controlled at 60 DEG C.By mixed liquor and chlorosulfuric acid according to phenol and sulphur
The ratio of acyl chlorides equimolar amounts, which is passed through in fixed bed reactors, carries out chlorination reaction, and fixed bed reactors pass through shell side heat exchanger control
Temperature processed is 120 DEG C.The depickling liquid of depickling qualification is continuously transferred to rectifying column, and phenol is detached with ethers catalyst, is returned
Diphenyl sulfide catalyst 0.9kg is received, 2,4- chlorophenesic acid 173.0kg, content 99.6%, yield 99.5% are obtained.
Claims (10)
1. one kind 2, the production system of 4- chlorophenesic acids, which is characterized in that including：
Fixed bed reactors, the fixed bed reactors include phenol feed inlet, chlorosulfuric acid feed inlet and discharge port, the fixation
It is provided with load type metal saline catalyst in bed reactor；
Extracting tower, the extracting tower include feed inlet, gas discharge mouth and liquid outlet opening, the feed inlet of the extracting tower and institute
The discharge port for stating fixed bed reactors is connected；
Rectifying column, the feed inlet of the rectifying column are connected with the liquid outlet opening of the extracting tower.
2. production system according to claim 1, which is characterized in that further include chlorosulfuric acid distributor；The chlorosulfuric acid point
Cloth device is set in the fixed bed reactors.
3. production system according to claim 1, which is characterized in that the fixed bed reactors by Multiple Superposition tubulation
Composition；Chlorosulfuric acid distributor is provided between the tubulation.
4. production system according to claim 1, which is characterized in that the side wall of the fixed bed reactors is provided with shell side
Heat-exchange system.
5. production system according to claim 1, which is characterized in that further include chlorosulfuric acid reactor；The chlorosulfuric acid is anti-
It includes tail gas feed inlet, chlorine feed mouth and discharge port to answer device；The tail gas feed inlet of the chlorosulfuric acid reactor and the depickling
The gas discharge mouth of tower is connected；The discharge port of the chlorosulfuric acid reactor and the chlorosulfuric acid feed inlet of the fixed bed reactors
It is connected.
6. one kind 2, the production method of 4- chlorophenesic acids, which is characterized in that including：
Using the production system described in Claims 1 to 5 any one；
Phenol is mixed with ethers catalyst, obtains mixed liquor；
The mixed liquor and chlorosulfuric acid are passed through in fixed bed reactors, chlorination reaction is carried out, obtains reaction solution；
By the reaction solution after depickling processing and rectification process, 2,4- chlorophenesic acids are obtained.
7. production method according to claim 6, which is characterized in that the ethers catalyst is dipropyl sulfide and/or benzene
Thioether.
8. production method according to claim 6, which is characterized in that the load type metal saline catalyst includes carrier
With metal salt；The metal salt is one or more in ferric trichloride, ferric iodide and ferric bromide；The carrier is polyacrylic acid
Ion exchange resin or silica dioxide granule.
9. production method according to claim 6, which is characterized in that the quality of the ethers catalyst is phenol quality
0.01%~0.1%.
10. production method according to claim 6, which is characterized in that the temperature of the chlorination reaction is 40 DEG C~100
℃；The temperature of the depickling processing is 80 DEG C~120 DEG C.
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| CN201710076400.4A CN108424355A (en) | 2017-02-13 | 2017-02-13 | A kind of production method and production system of 2,4 dichloro phenol |
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| CN201710076400.4A CN108424355A (en) | 2017-02-13 | 2017-02-13 | A kind of production method and production system of 2,4 dichloro phenol |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503331A (en) * | 2019-01-23 | 2019-03-22 | 淮南师范学院 | A method of high-purity hydrogen chloride gas is prepared by 2,4 dichloro phenol by-product |
| CN115385779A (en) * | 2022-08-19 | 2022-11-25 | 湖北泰盛化工有限公司 | 2, 4-dichlorophenol continuous rectification method |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106349025A (en) * | 2016-07-28 | 2017-01-25 | 连云港致诚化工有限公司 | Preparation process of 2,4-dichlorophenol |
-
2017
- 2017-02-13 CN CN201710076400.4A patent/CN108424355A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106349025A (en) * | 2016-07-28 | 2017-01-25 | 连云港致诚化工有限公司 | Preparation process of 2,4-dichlorophenol |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503331A (en) * | 2019-01-23 | 2019-03-22 | 淮南师范学院 | A method of high-purity hydrogen chloride gas is prepared by 2,4 dichloro phenol by-product |
| CN109503331B (en) * | 2019-01-23 | 2021-11-30 | 淮南师范学院 | Method for preparing high-purity hydrogen chloride gas from 2, 4-dichlorophenol byproduct |
| CN115385779A (en) * | 2022-08-19 | 2022-11-25 | 湖北泰盛化工有限公司 | 2, 4-dichlorophenol continuous rectification method |
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