CN116354800B - Production method of 2, 5-dichloro-p-xylylene ether - Google Patents
Production method of 2, 5-dichloro-p-xylylene ether Download PDFInfo
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- -1 2, 5-dichloro-p-xylylene ether Chemical compound 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 107
- 238000005660 chlorination reaction Methods 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 25
- 239000000047 product Substances 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 17
- 239000000460 chlorine Substances 0.000 claims abstract description 16
- 239000002994 raw material Substances 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 238000001816 cooling Methods 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000007787 solid Substances 0.000 claims abstract description 4
- 230000001502 supplementing effect Effects 0.000 claims abstract description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical group CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 12
- 239000012295 chemical reaction liquid Substances 0.000 claims description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 239000007810 chemical reaction solvent Substances 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000007789 gas Substances 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- 239000006227 byproduct Substances 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000007791 liquid phase Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 claims description 2
- 239000012065 filter cake Substances 0.000 claims description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical group Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 2
- 239000012047 saturated solution Substances 0.000 claims 2
- 238000000034 method Methods 0.000 abstract description 13
- 230000008569 process Effects 0.000 abstract description 9
- 238000005516 engineering process Methods 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- YGUFQYGSBVXPMC-UHFFFAOYSA-N 4-chloro-2,5-dimethoxyaniline Chemical compound COC1=CC(Cl)=C(OC)C=C1N YGUFQYGSBVXPMC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013064 chemical raw material Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- RGVBYOCNGAHKMT-UHFFFAOYSA-N 3-oxabicyclo[3.2.2]nona-1(7),5,8-triene Chemical compound C1OCC2=CC=C1C=C2 RGVBYOCNGAHKMT-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 244000046095 Psophocarpus tetragonolobus Species 0.000 description 1
- 235000010580 Psophocarpus tetragonolobus Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000007599 discharging Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
- C07C41/40—Separation; Purification; Stabilisation; Use of additives by change of physical state, e.g. by crystallisation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a production method of 2, 5-dichloro-p-xylylene ether, which comprises the following steps: in the presence of a catalyst, introducing chlorine into a solvent system in which the terephthalyl ether is dissolved, heating to carry out chlorination reaction, cooling and crystallizing after the reaction is completed, collecting the filtered solid as a product, supplementing the terephthalyl ether into the filtrate, and continuing the chlorination reaction as a chlorination raw material. Compared with the prior art, the technology of the invention has the characteristics of simple process, environmental protection and high purity of target products, and effectively solves the problems existing in the prior art.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a production method of 2, 5-dichloro-p-xylylene ether.
Background
The 2, 5-dichloro-terephthalyl ether is white-light red gray solid and is a systemic bactericide. Can be used for preventing and treating seedling diseases of cotton, hyacinth bean and soybean. The preparation has 65% wettable powder. Meanwhile, the product can prepare 4-chloro-2, 5-dimethoxy aniline through ammonolysis reaction. The 4-chloro-2, 5-dimethoxy aniline is an important intermediate of organic pigment and pesticide, the appearance of the intermediate is light gray powder, the melting point is 118-120 ℃, the content is usually more than 98 percent, the intermediate is the main raw material of synthetic phenols AS-IRG and AS-LC, and the two kinds of phenols are mainly used for producing pigment yellow 83, pigment yellow 97 and pigment red 146, are widely used for coloring ink, paint, plastic, rubber and the like, and have good coloring performance. The organic chemical raw material has wide application in daily production and life, and is an organic chemical raw material with the market demand increasing year by year in recent years.
As known from the prior art, no literature report on the single preparation of 2, 5-dichloro-terephthalyl ether by chlorination of terephthalyl ether has been found. Only the literature report that benzyl trimethyl tetrachloroiodic acid amine is adopted to catalyze terephthalyl ether to synthesize 2, 5-dichloro terephthalyl ether is adopted, but the post-treatment process reported by the process is relatively complex, sodium bisulphate, benzene, sodium bicarbonate, column chromatography, vacuum concentration and the like are adopted successively to obtain target products, and although the reported yield is 90%, the melting point of the obtained 2, 5-dichloro terephthalyl ether is 129-130 ℃ and has a certain gap from the current commercial 133-135 ℃.
Disclosure of Invention
The invention provides a method for producing 2, 5-dichloro-p-xylylene ether, in particular to a method for producing 2, 5-dichloro-p-xylylene ether by chloridizing reaction of p-xylylene ether serving as a raw material with Cl 2 under the action of a catalyst FeCl 3. The technology of the invention has the characteristics of simple process, environmental protection and high purity of target products, and effectively solves the problems existing in the prior art.
The following is a specific technical scheme of the invention:
A method for producing 2, 5-dichloro-p-xylylene ether, comprising: in the presence of a catalyst, introducing chlorine into a solvent system in which the terephthalyl ether is dissolved, heating to carry out chlorination reaction, cooling and crystallizing after the reaction is completed, collecting the filtered solid as a product, supplementing the terephthalyl ether into the filtrate, and continuing the chlorination reaction as a chlorination raw material.
Preferably, the chlorination reaction temperature is 30 to 80 ℃. More preferably, the chlorination reaction temperature is 40 to 80 ℃, still more preferably 40 to 70 ℃. As a specific preferable scheme, the chlorination reaction temperature is 40-60 ℃; further the temperature is 45-60 ℃; further, the temperature is controlled to be 45-55 ℃ and further 48-52 ℃. The reaction pressure is generally normal pressure.
Preferably, the reaction time is from 6 to 12 hours. More preferably 8 to 10 hours.
Preferably, the reaction solvent is selected from dichloroethane or dichloromethane. Further preferred is dichloroethane. The mass ratio of the reaction solvent (such as dichloroethane) to the terephthalyl ether is 3-7:1.
Preferably, the temperature is reduced to 30 ℃ below zero to 10 ℃ below zero (namely-30 ℃ to-10 ℃). Further preferably from-25℃to-10 ℃; still more preferably at-20℃to-15 ℃.
Preferably, the catalyst is ferric chloride. The catalyst is preferably added in the following amount: 0.1 to 0.6 percent of paraphthalimide by mass; more preferably 0.2 to 0.5%.
Preferably, the mol ratio of Cl 2 to terephthalyl ether is 1.8-2.2:1; the step is preferably 1.9-2.2:1; still more preferably 2 to 2.2:1.
As a possible embodiment:
a method for producing 2, 5-dichloro-p-xylylene ether comprises the following steps:
1) Chlorination: dissolving terephthalyl ether and a catalyst FeCl 3 in a solvent (such as dichloroethane) or applying mother solution to prepare a solution, and introducing metered Cl 2 into the solution under stirring at an elevated temperature to carry out chlorination reaction;
2) Crystallization separation: the gas containing hydrogen chloride is absorbed by water to prepare by-product hydrochloric acid with the content of 31 percent, after the reaction is finished, the liquid phase is cooled to the temperature of minus 10 ℃ to minus 30 ℃ to crystallize and separate out 2, 5-dichloro terephthalyl ether from the reaction liquid, the product 2, 5-dichloro terephthalyl ether is obtained after filtration and washing with dichloroethane, and the filtrate is used as a chlorination raw material to continue the chlorination reaction after the terephthalyl ether is added.
After the reaction is finished (i.e. after the reaction is carried out for 6 to 12 hours), the content of the 2, 5-dichloro-terephthalyl ether in the chlorination reaction liquid reaches 40 to 60 percent (more preferably, the content of the 2, 5-dichloro-terephthalyl ether in the chlorination reaction liquid is 45 to 55 percent), the terephthalyl ether is basically reacted completely at the moment, and the product is separated out by cooling at the moment, so that the further occurrence of side reaction can be avoided to the greatest extent. In the reaction system, besides the target product, a part of monochloro products (about 15% -30%) and a small part of trichloro and tetrachloro products (about 5% -15%) are generated; the monochloro product can continuously react with chlorine in the subsequent application reaction to form a target product 2, 5-dichloro-p-xylylene ether; a small part of the trichloro and tetrachloro products and the monochloro products are subjected to an equilibrium reaction, so that a part of the target product 2, 5-dichloro-p-xylylene ether is also formed.
The mass ratio of the dichloroethane to the terephthalyl ether in the step 1) is preferably 4.5-5.5:1; the addition amount of FeCl 3 is preferably 0.15 to 0.4% by mass of paraxylylene ether; the mol ratio of Cl 2 to terephthalyl ether is preferably 2-2.1:1; the reaction temperature is preferably 35 to 70 ℃, more preferably 45 to 55 ℃, still more preferably 48 to 52 ℃, and the reaction time is preferably 8 to 10 hours.
The content of 2, 5-dichloro terephthalyl ether in the chlorination reaction liquid in the step 2) is preferably 45-55%; the liquid phase is cooled to a temperature of preferably 15 ℃ below zero to 25 ℃.
Preferably, after cooling crystallization and filtration, a reaction solvent can be adopted to wash a filter cake, and 2, 5-dichloro-terephthalyl ether saturated dichloroethane can also be adopted to wash; by adopting the latter, on one hand, trace impurities mixed in the catalyst can be removed, and meanwhile, the dissolution of extra 2, 5-dichloro-p-xylylene ether product is avoided; meanwhile, the washing liquid can be directly recycled into the reaction system, and the generation of three wastes is further avoided.
One of the key points of the invention is that the 2, 5-dichloro-terephthalyl ether in the chlorination reaction liquid is kept at a lower level by means of cooling crystallization separation, so that the target product is effectively inhibited from continuously carrying out deep chlorination reaction with Cl 2 to generate trichloro and tetrachloro-terephthalyl ether byproducts. The content of the crystal obtained by filtering can reach more than 99.2 percent after the crystal is washed by dichloroethane saturated with 2, 5-dichloro-terephthalyl ether; the filtrate containing dichloroethane, terephthalyl ether, 2-chloro terephthalyl ether, 2, 5-dichloro terephthalyl ether, trichloro and tetrachloroterephthalyl ether and catalyst FeCl 3 is not required to be treated, and can be directly chlorinated after raw materials are supplemented, and the selectivity of 2, 5-dichloro terephthalyl ether can be effectively improved due to the fact that a proper amount of trichloro and tetrachloroterephthalyl ether are contained in the reaction liquid, so that the reaction yield is improved.
The second key point of the invention is that, unlike the conventional chlorination process, the catalyst can be recycled without separate separation, and separation and purification of raw materials and byproducts are not needed, the reaction process has no three wastes, and the subsequent rectification separation is not needed, so that no three wastes are generated, the chlorination process is simplified, and the energy consumption is reduced.
Analysis of the mechanism of the chlorination reaction of terephthalyl ether shows that the chlorination reaction of terephthalyl ether consists of a series of series-connected chlorination processes. The terephthalyl ether firstly reacts with 1 molecule of Cl 2 to generate 2-chloro terephthalyl ether and HCl, the content of the 2-chloro terephthalyl ether in the reaction liquid correspondingly increases along with the extension of the reaction time, then the chlorination is continued to generate 2, 5-dichloro terephthalyl ether, and then when the content of the 2, 5-dichloro terephthalyl ether increases, the deep chlorination generates trichloro and tetrachloroterephthalyl ether. The generated 2, 5-dichloro-p-xylylene ether is removed in time in the reaction process, and the method is an effective method for improving the selectivity of the target product from the aspects of dynamics and thermodynamics.
Compared with the prior art, the method has the advantages that the method takes the terephthalyl ether as the raw material and performs the chlorination reaction with Cl 2 to produce the 2, 5-dichloro terephthalyl ether under the action of the catalyst FeCl 3. The technology of the invention has the characteristics of simple process, environmental protection and high purity of target products, and effectively solves the problems existing in the prior art.
Detailed Description
Examples 1 to 11
Chlorination: the chlorination reaction was carried out in a1 liter glass reactor with stirring device, gas distributor, gas vent and temperature control system. The metered amounts of dichloroethane solvent, paraxylylene ether (216 g in the examples) and catalyst FeCl 3 (the catalyst addition was calculated as a percentage of the paraxylylene ether addition) were added to the reactor, and stirring was started to make the reaction solution a homogeneous solution. And then nitrogen is introduced to replace the reaction system, so that the oxygen content in the reaction kettle is ensured to be qualified. And heating the reaction liquid to a set temperature by using a temperature control system with heating and refrigerating functions, continuously introducing metered Cl 2 for reaction, discharging generated gas HCl through an exhaust port, absorbing with water, preparing byproduct hydrochloric acid with the content of 31%, absorbing tail gas through alkali, and then evacuating.
Crystallization separation: after the content of 2, 5-dichloro-p-xylylene ether in the reaction liquid was increased to the reaction time shown in Table 1, the temperature of the reaction liquid was lowered to-15℃to conduct low temperature crystallization and filtration. After washing the crystal obtained by filtration with dichloroethane saturated with 2, 5-dichloro-terephthalyl ether, the washing liquid and the filtration mother liquid are returned to the reaction for cyclic use. The operating conditions for each example are shown in Table 1.
TABLE 1
Examples 12 to 14
Example 12 is a mother liquor jacket performed in example 2 under optimal reaction process conditions, and the specific results are shown in table 2; examples 13 and 14 are crystallization post-treatment operations at 5℃and-25℃respectively, under optimal reaction process conditions, with specific results shown in Table 2.
TABLE 2
As is clear from Table 2, the control of crystallization temperature has a certain effect on the product yield, but the purity of the obtained product is high.
Example 15
Performing a number of times experiment according to the conditions of example 2, wherein the ratio of the paraxylylene ether to the chlorine added each time is unchanged, and adding the solvent or the catalyst according to the loss condition in the process of the application; experiments show that after 20 times of circulation, the yield and purity of the product are basically unchanged.
Claims (6)
1. A method for producing 2, 5-dichloro-p-xylylene ether, comprising: introducing chlorine into a solvent system in which the terephthalyl ether is dissolved in the presence of a catalyst, heating to perform chlorination reaction, cooling to crystallize after the reaction is completed, collecting the filtered solid as a product, supplementing the terephthalyl ether into the filtrate, and continuing the chlorination reaction as a chlorination raw material;
The chlorination reaction temperature is 30-80 ℃;
the reaction solvent is selected from dichloroethane or dichloromethane;
the catalyst is ferric chloride;
the temperature is reduced to minus 30 ℃ to minus 10 ℃;
the adding amount of the catalyst is 0.1-0.6% by mass of the terephthalyl ether;
the mol ratio of Cl 2 to terephthalyl ether is 1.8-2.2:1.
2. The method for producing 2, 5-dichloro-p-xylylene ether according to claim 1, wherein the reaction time is 6 to 12 hours.
3. The production method of 2, 5-dichloro-p-xylylene ether according to any one of claims 1 to 2, comprising the steps of:
(1) Chlorination: dissolving terephthalyl ether and a catalyst FeCl 3 in a solvent to prepare a solution, and introducing metered Cl 2 into the solution under stirring at an elevated temperature for chlorination reaction;
(2) Crystallization separation: the gas containing hydrogen chloride in the reaction is absorbed by water to prepare byproduct hydrochloric acid, after the chlorination reaction is completed, the liquid phase is cooled to the temperature of minus 30 ℃ to minus 10 ℃ to crystallize and separate out 2, 5-dichloro-p-phenylene dimethyl ether from the reaction liquid, and the product 2, 5-dichloro-p-phenylene dimethyl ether is obtained after filtration and washing, and the filtrate is directly used as mother liquor for the chlorination reaction.
4. A method for producing 2, 5-dichloro-p-xylylene ether according to claim 3, wherein the filter cake is washed with a saturated solution of 2, 5-dichloro-p-xylylene ether, and the saturated solution is the same as the reaction solvent.
5. The method for producing 2, 5-dichloro-p-xylylene ether according to claim 3, wherein the chlorination reaction temperature is 40-60 ℃; the reaction time is 8-12 h; the reaction solvent is dichloroethane; the temperature is reduced to minus 30 ℃ to minus 10 ℃; the mol ratio of Cl 2 to terephthalyl ether is 2-2.2:1; the mass ratio of the reaction solvent to the terephthalyl ether is 4.5-5.5:1.
6. The method for producing 2, 5-dichloro-p-xylylene ether according to claim 1, wherein the content of 2, 5-dichloro-p-xylylene ether in the chlorination reaction liquid after completion of the reaction is 40% -60%.
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| Title |
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| Pilar Lo´ pez-Alvarado，等.EFFICIENT, MULTIGRAM-SCALE SYNTHESIS OF THREE 2,5-DIHALOBENZOQUINONES.SYNTHETIC COMMUNICATIONS.2002,第32卷(第20期),第3235页Scheme 1.及第3236页第2段. * |
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