CN1128127C - Process for preparing benzylchlorine - Google Patents
Process for preparing benzylchlorine Download PDFInfo
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- CN1128127C CN1128127C CN 01108198 CN01108198A CN1128127C CN 1128127 C CN1128127 C CN 1128127C CN 01108198 CN01108198 CN 01108198 CN 01108198 A CN01108198 A CN 01108198A CN 1128127 C CN1128127 C CN 1128127C
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- CN
- China
- Prior art keywords
- benzyl chloride
- toluene
- chlorine
- chlorination
- tower
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- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 title claims abstract description 64
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 105
- 229940073608 benzyl chloride Drugs 0.000 claims abstract description 62
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- 238000005286 illumination Methods 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000007599 discharging Methods 0.000 claims abstract description 7
- 239000000945 filler Substances 0.000 claims abstract description 7
- 239000012780 transparent material Substances 0.000 claims abstract description 6
- 230000001699 photocatalysis Effects 0.000 claims abstract description 3
- 238000007146 photocatalysis Methods 0.000 claims abstract description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 26
- 239000000460 chlorine Substances 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 239000011521 glass Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000010453 quartz Substances 0.000 claims description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 3
- 239000012535 impurity Substances 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract description 7
- 239000003814 drug Substances 0.000 abstract description 5
- 239000000575 pesticide Substances 0.000 abstract description 4
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract 1
- 238000004043 dyeing Methods 0.000 abstract 1
- 230000000087 stabilizing effect Effects 0.000 abstract 1
- 239000000047 product Substances 0.000 description 17
- 239000007789 gas Substances 0.000 description 9
- CAHQGWAXKLQREW-UHFFFAOYSA-N Benzal chloride Chemical compound ClC(Cl)C1=CC=CC=C1 CAHQGWAXKLQREW-UHFFFAOYSA-N 0.000 description 8
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 230000002194 synthesizing effect Effects 0.000 description 5
- 238000010924 continuous production Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000066 reactive distillation Methods 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- -1 benzyl ester Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- LEZWWPYKPKIXLL-UHFFFAOYSA-N 1-{2-(4-chlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound C1=CC(Cl)=CC=C1COC(C=1C(=CC(Cl)=CC=1)Cl)CN1C=NC=C1 LEZWWPYKPKIXLL-UHFFFAOYSA-N 0.000 description 1
- CIVCELMLGDGMKZ-UHFFFAOYSA-N 2,4-dichloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC(Cl)=C(C(O)=O)C(Cl)=N1 CIVCELMLGDGMKZ-UHFFFAOYSA-N 0.000 description 1
- VGKYEIFFSOPYEW-UHFFFAOYSA-N 2-methyl-4-[(4-phenyldiazenylphenyl)diazenyl]phenol Chemical compound Cc1cc(ccc1O)N=Nc1ccc(cc1)N=Nc1ccccc1 VGKYEIFFSOPYEW-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 229960002233 benzalkonium bromide Drugs 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- KHSLHYAUZSPBIU-UHFFFAOYSA-M benzododecinium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 KHSLHYAUZSPBIU-UHFFFAOYSA-M 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 1
- 229960000525 diphenhydramine hydrochloride Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 229960003913 econazole Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 description 1
- 229960004618 prednisone Drugs 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010977 unit operation Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The present invention provides a method for preparing benzyl chlorine, which relates to fine chemical engineering. Under the condition of photocatalysis for toluene and chlorine gas, the benzyl chloride is produced by a technological process of chlorinating rectification, and raw materials of the toluene and the chlorine gas are continuous fed; products the benzyl chloride are continuous discharged. A main device is a chlorinating rectifying tower composed of a tower kettle, a stripping section and an illumination reaction section, and a toluene feeding pipe is positioned on the upper part of the illumination reaction section; a benzyl chloride discharging pipe is positioned in the tower kettle, and a chlorine gas feeding pipe is positioned in the stripping section; fillers in the chlorinating rectifying tower is transparent materials. The present invention has the advantages of stabilizing production processes, greatly enlarging production scales, reducing production cost by about 15% and improving the purity and the quality of products, and the content of products of the benzyl chloride reaches above 99%; therefore, the present invention is high-purity benzyl chloride which is a product desired by medicine industry, pesticide industry, dyeing industry, etc.
Description
The present invention relates to fine chemical technology, and is especially the production process of benzyl chloride.
Benzyl chloride (formula C)6H5CH2Cl) is an intermediate required by medicines, dyes, pesticides and organic synthesis, is used for synthesizing phenylacetic acid in medicine and finally synthesizing penicillin, and can also be used for synthesizing diphenhydramine hydrochloride, benzalkonium bromide, econazole, prednisone, phentermine, phenylacetamide and other medicines with large consumption; the pesticide is used for producing the rice blast, and the dye is used for producing products such as a dispersant CNF, a dissolved salt B, a disperse yellow S-RFL, a high-temperature leveling agent A-10 and the like; the synthesis of other organic products such as surfactant benzalkonium chloride and the production of benzyl ester plasticizer all need benzyl chloride as raw material intermediate. However, the benzyl chloride is produced by using toluene and chlorine as raw materials, generating a mixture containing the benzyl chloride and other reaction products under a catalytic condition, and then performing rectification separation, wherein the production process is batch production or semi-continuous production. Due to the backward production technology, a large amount of mixture consisting of dichlorobenzyl, trichlorobenzyl and tar is generated in the process of producing benzyl chloride, which brings difficulty to the separation of the benzyl chloride, and leads the production process to be complex, the unit consumption of raw materials to be high, and the content of the benzyl chloride to be low, which is generally only 97 percent. The production scale is small, and the production cost is high.
The invention aims to provide a method for producing benzyl chloride, which has the advantages of continuous production process, high benzyl chloride content and low production cost.
The technical scheme for achieving the aim of the invention is that toluene and chlorine are subjected to chlorination reaction in a light irradiation reaction section under a photocatalysis condition, benzyl chloride is produced by a chlorination rectification process of rectification and purification in a stripping section, the toluene and chlorine as raw materials are continuously fed, the benzyl chloride as a product is continuously discharged, and the volume ratio of the feeding amount of the toluene and the chlorine to the discharging amount of the benzyl chloride is 1: 200-220: 1.02-1.23.
The main device for realizing the purpose of the invention is a chlorination and rectification tower consisting of a tower kettle, a stripping section and a light reaction section, wherein a toluene inlet pipe is positioned at the upper part of the light reaction section, a benzyl chloride outlet pipe is positioned at the tower kettle, a chlorine gas inlet pipe is positioned at the stripping section, and a filler in the chlorination and rectification tower is made of transparent materials.
The reaction principle of the present invention is as follows;
the reaction equation for toluene and chlorine is:
in the above-mentioned series of chlorination reactions, there are three reactions, and only the benzyl chloride, which is the reaction product of the first-stage reaction (1), is the desired product of the present invention. Therefore, if the reaction process is not controlled, the reaction of toluene and chlorine continues to generate the reaction product benzyl dichloride of the second-stage reaction (2) and the reaction product benzyl trichloride of the third-stage reaction (3) to form a complex mixture containing various components such as toluene, benzyl chloride, benzyl dichloride, benzyl trichloride and the like, which brings great difficulty for subsequent separation and purification of benzyl chloride. The existing industrial technology is a process combining batch chlorination reaction and batch rectification separation, when the reaction of toluene and chlorine is stopped until the conversion rate reaches about 60%, the reaction mixture is rectified for many times, and benzyl chloride is separated out. However, when the conversion rate reaches 60%, the content of benzyl dichloride and benzyl trichloride is high, and the content of benzyl chloride in the rectified benzyl chloride product is also high, so that the content of benzyl chloride in the product can only reach about 97%, and if further purification is carried out, equipment needs to be added, the operation cost and the raw material consumption are increased, and the product cost is greatly increased. If the conversion rate is controlled to be lower, the generation of benzyl dichloride and benzyl trichloride can be controlled, but the load of rectifying and separating benzyl chloride is increased, so that the production capacity is influenced, and the production cost is greatly improved. In order to improve the purity of the product and reduce the production cost, the invention adopts the modern reactive distillation technology to be applied to the production of benzyl chloride, namely, benzyl chloride is produced by a chlorination distillation synthesis method, the second-stage reaction and the third-stage reaction in the reaction of toluene and chlorine are strictly controlled, the concentration of the product benzyl chloride of the first-stage reaction is controlled, the higher the concentration of the benzyl chloride is, the higher the concentrations of the second-stage reaction product benzyl dichloride and the third-stage reaction product benzyl trichloride are, and the lower the concentration of the benzyl chloride is, the lower the concentrations of the benzyl dichloride and the benzyl trichloride are, and in order to ensure that the content of the benzyl chloride in a tower kettle is more than 99 percent, through calculation and specific practice of reaction kinetics, the result shows that the content of the benzyl chloride in a light irradiation reaction section is required to be controlled to be less than. Inthe process of technological operation, the volume ratio of the feeding amount of the toluene and the chlorine to the discharging amount of the benzyl chloride is kept to be 1: 200-220: 1.02-1.23, and meanwhile, the total content of impurity iron in the fed toluene and chlorine is less than 0.01%. Because the chlorination and rectification tower is adopted to synthesize the benzyl chloride, continuous feeding and discharging can be carried out, and continuous production in the whole process is realized, and the continuous production process is convenient to adopt automatic control, so that the production process is stable, the production scale can be greatly improved, the production cost is reduced by about 15 percent, and the purity and the quality of the product are improved.
Different from the common reactive distillation technology applied to the processes of esterification reaction, etherification reaction and the like, in the process of synthesizing benzyl chloride by the chlorination distillation synthesis method, the product is a component which is difficult to volatilize, and the product benzyl chloride can only be discharged from a tower kettle, which brings more difficulty to the design and process control of the reactive distillation tower. The chlorination and rectification tower as the main apparatus for chlorination and rectification combines two unit operations of chlorination reaction and rectification together and consists of tower kettle, stripping section, illumination reaction section, etc. benzyl chloride is discharged from the tower kettle, chlorine gas is fed to the stripping section below the illumination reaction section, and toluene is fed to the upper part of the illumination reaction section.
As the chlorination reaction of the toluene and the chlorine is a gas-liquid heterogeneous reaction, in order to obtain a better gas phase distribution effect and a larger gas-liquid contact area and promotethe reaction, a packed reaction rectifying tower is adopted, and in order to obtain better illumination depth and uniformity of a reaction area, a packing is made of transparent materials, such as glass, transparent plastic, quartz and the like. In order to effectively control the reaction process of chlorination rectification, the position of a reaction section in the tower can be controlled by adjusting the position of a light source and the position of a chlorine gas feeding pipe, and the number of the chlorine gas feeding pipes is 1-6.
The high-purity benzyl chloride with the benzyl chloride content of more than 99 percent is an urgent product in the industries of medicine, pesticide, dye and the like, and lays a foundation for reducing import and providing export.
The invention is further illustrated by the following examples and figures.
FIG. 1 is a schematic diagram of a chlorination rectification column.
FIG. 2 is a schematic diagram of a process flow for synthesizing benzyl chloride by chlorination and rectification.
Referring to fig. 1-2, a chlorination rectification tower 2 is provided with a tower kettle 7, a heater 9 is arranged in the tower kettle 7, an oil furnace heater is adopted here, a stripping section 5 is connected above the tower kettle 7, an illumination reaction section 3 is arranged above the stripping section 5, a light source 13 is arranged on the periphery of the illumination reaction section 3, the light source adopts a mercury lamp or other light sources, the stripping section 5 and the illumination reaction section 3 are filled with a filler 6, the filler 6 is a transparent material, and the filler adopts glass or transparent plastic or quartz.
The production operation process comprises the following steps: firstly, crude distillation is carried out on raw material toluene and a certain amount of benzyl chloride are put into a tower kettle 7 of a chlorination rectification tower 2, a heater 9 is started to heat, cooling water in a condenser 11 is started, the toluene in the tower kettle is evaporated into gas, the gas flows out from a gas discharge pipe 1 at the top of the tower, enters the condenser 11 through a condenser inlet pipe 10 to be condensed into liquid, flows out from a condenser outlet pipe 12, enters an illumination reaction section 3 in the chlorination rectification tower 2 through a toluene feed pipe 14, and when the toluene content in the illumination reaction section 3 reaches over 85.5 percent and the benzyl chloride content in the tower kettle 7 reaches over 99 percent, continuous addition of toluene and chlorine is started. Toluene after crude distillation enters a condenser 11 through a condenser inlet pipe 10 to be condensed into liquid, flows out of a condenser outlet pipe 12, enters an illumination reaction section 3 in a chlorination rectification tower 2 through a toluene inlet pipe 14, chlorine enters a stripping section 5 from a chlorine inlet pipe 4, rises to the illumination reaction section 3, reacts with the toluene under the catalytic action of light to generate benzyl chloride, hydrogen chloride and trace benzyl dichloride, the benzyl chloride and the trace benzyl dichloride flow downwards to enter the stripping section 5 for rectification separation, the temperature of a tower kettle 7 is controlled to be between 175 and 185 ℃, the volume ratio of the feeding amount of the toluene and the chlorine to the discharging amount of the benzyl chloride is controlled to be between 1: chlorine and benzyl chloride and 1: 200-220: 1.02-1.23, the content of the benzyl chloride in the illumination reaction section 3 is controlled to be less than 14.5 percent, and the generated hydrogen chloride gas and unreacted toluene gas flow out from a gas outlet pipe 1 at the top of the tower, enters a condenser 11 through a condenser inlet pipe 10 for condensation, the toluene is condensed into liquid, enters the illumination reaction section 3 from a condenser outlet pipe 12 through a toluene inlet pipe 14, and the toluene at the tower top is totally refluxed. The hydrogen chloride gas is discharged out of the reaction system from an outlet pipe 12 of the condenser, a byproduct of 30% hydrochloric acid is obtained through a tail gas absorption device, the content of benzyl chloride in the product reaches 99.1-99.5%, and the result of the product is 99.3% after the product is inspected by a product quality supervision and inspection center of Jiangsu province.
Claims (6)
1. A production method of benzyl chloride is characterized in that: the method comprises the steps of carrying out chlorination reaction on toluene and chlorine through an illumination reaction section (3) under a photocatalysis condition, and then producing benzyl chloride through a chlorination rectification process of rectification and purification of a stripping section (5), wherein the toluene and chlorine are continuously fed as raw materials, the benzyl chloride is continuously discharged, and the volume ratio of the feeding amount of the toluene and the chlorine to the discharging amount of the benzyl chloride is 1: 200-220: 1.02-1.23.
2. The process for the production of benzyl chloride according to claim 1, characterized in that: the total content of impurity iron in the fed toluene and chlorine is less than 0.01 percent.
3. The process for the production of benzyl chloride according to claim 1, characterized in that: controlling the content of benzyl chloride in the illumination reaction section (3) to be less than 14.5 percent.
4. A chlorination rectification column [ 2]for producing benzyl chloride, characterized in that: it mainly comprises a tower kettle (7), a stripping section (5) and a light reaction section (3); a toluene feeding pipe (14) is positioned at the upper part of the illumination reaction section (3), a benzyl chloride discharging pipe (8) is positioned at the tower bottom (7), and a chlorine feeding pipe (4) is positioned at the stripping section (5); the filler (6) in the chlorination rectification tower (2) is made of transparent materials.
5. The chlorination rectification column [ 2]for producing benzyl chloride according to claim 5, characterized in that: the number of the feed pipes (4) for chlorine is 1-6.
6. The chlorination rectification column [ 2]for producing benzyl chloride according to claim 5, characterized in that: the transparent material of the filler (6) is glass, transparent plastic or quartz.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01108198 CN1128127C (en) | 2001-04-09 | 2001-04-09 | Process for preparing benzylchlorine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01108198 CN1128127C (en) | 2001-04-09 | 2001-04-09 | Process for preparing benzylchlorine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1316409A CN1316409A (en) | 2001-10-10 |
| CN1128127C true CN1128127C (en) | 2003-11-19 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01108198 Expired - Fee Related CN1128127C (en) | 2001-04-09 | 2001-04-09 | Process for preparing benzylchlorine |
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| Country | Link |
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Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113041636A (en) * | 2019-12-27 | 2021-06-29 | 浙江省化工研究院有限公司 | Continuous bromination addition reaction rectification process and device |
| CN115850015A (en) * | 2022-09-13 | 2023-03-28 | 河北三川化工有限公司 | Production process and application of benzyl chloride |
| CN115850016A (en) * | 2022-09-14 | 2023-03-28 | 河北三川化工有限公司 | Production method and application of o-chloro-series products |
| CN117362148A (en) * | 2023-10-07 | 2024-01-09 | 湖北可赛化工有限公司 | Novel method for synthesizing trichlorobenzyl by photochlorination |
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| Publication number | Publication date |
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| CN1316409A (en) | 2001-10-10 |
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