CN114195617B - Synthesis method of 4-bromodiphenyl - Google Patents
Synthesis method of 4-bromodiphenyl Download PDFInfo
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- CN114195617B CN114195617B CN202111639293.4A CN202111639293A CN114195617B CN 114195617 B CN114195617 B CN 114195617B CN 202111639293 A CN202111639293 A CN 202111639293A CN 114195617 B CN114195617 B CN 114195617B
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- bromodiphenyl
- biphenyl
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- molar ratio
- bromobiphenyl
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- PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000001308 synthesis method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- 238000004821 distillation Methods 0.000 claims abstract description 21
- 239000000047 product Substances 0.000 claims abstract description 16
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 23
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 20
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 20
- 235000010290 biphenyl Nutrition 0.000 claims description 19
- 239000004305 biphenyl Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- -1 methyl tetrafluoroborate Chemical compound 0.000 claims description 12
- 239000002244 precipitate Substances 0.000 claims description 12
- 238000009423 ventilation Methods 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 11
- 229940102001 zinc bromide Drugs 0.000 claims description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000001301 oxygen Substances 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000002608 ionic liquid Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 230000002194 synthesizing effect Effects 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 238000004321 preservation Methods 0.000 claims description 6
- 125000006267 biphenyl group Chemical group 0.000 claims description 2
- 238000004065 wastewater treatment Methods 0.000 claims description 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 6
- 239000002253 acid Substances 0.000 abstract description 4
- 239000006227 byproduct Substances 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 150000003839 salts Chemical class 0.000 abstract description 3
- 230000009286 beneficial effect Effects 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000010189 synthetic method Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002351 wastewater Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012954 diazonium Substances 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 239000000990 laser dye Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
-
- 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
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of 4-bromodiphenyl, which sequentially comprises the following steps: (1) mixing and preparing; (2) oxidation reaction; (3) separation distillation. The beneficial effects are that: the invention provides a synthetic method of 4-bromodiphenyl, which has mild reaction conditions, no potential safety hazard, and simultaneously does not need to use a large amount of strong acid and strong alkali, thereby avoiding the generation of a large amount of byproduct salt and reducing the economic cost; meanwhile, the yield of the 4-bromodiphenyl oxide product is high, the product purity is high, the quality is good, and the preparation process is simple.
Description
Technical field:
the invention relates to a preparation method of 4-bromodiphenyl, in particular to a synthesis method of 4-bromodiphenyl.
The background technology is as follows:
4-bromodiphenyl is a key intermediate of a plurality of fine chemical products such as laser dye, liquid crystal material, pesticide, medicine and the like.
The existing method for preparing 4-bromodiphenyl mainly comprises the following two steps:
(1) Cooling water, p-bromoaniline and concentrated hydrochloric acid together, keeping the temperature between 0 and 5 ℃, slowly adding sodium nitrite aqueous solution, diazotizing until the starch potassium iodide test paper is blue, and filtering out clarified diazonium solution. Adding benzene into diazonium solution, stirring at 5-10deg.C for half an hour, slowly dripping sodium hydroxide solution, stirring for 3 hr, and stirring at room temperature for 45 hr. Separating benzene layer, washing with water, distilling benzene, distilling under reduced pressure, collecting 170-175 deg.C (1.06 kPa) fraction, recrystallizing with ethanol to obtain final product with melting point of 90deg.C, with a real yield of 86% and purity of 98%; the following problems exist with the above method: diazotization is carried out in excessive strong acid, a large amount of strong acid and strong alkali are needed to be used, a large amount of byproduct salt is generated, and economic loss is caused; meanwhile, the reaction is diazotization reaction, and potential safety hazards exist.
(2) The Chinese patent No. 200810157467.1 (2009.3.4) reports that the preparation process is complex, the reactant hydrochloric acid is treated, the byproducts are more, and the actual yield of the product is only 62 percent.
The invention comprises the following steps:
the invention aims to provide a synthesis method of 4-bromodiphenyl oxide, which has simple process and high product yield.
The purpose of the invention is implemented by the following technical scheme: the synthesis method of the 4-bromodiphenyl comprises the following steps in sequence:
(1) And (2) mixing and preparing: adding a solvent into a reaction kettle, stirring, then adding biphenyl, ionic liquid, zinc bromide and hydrobromic acid in the stirring process, and then introducing nitrogen for 5-10min to replace air in the reaction kettle;
(2) Oxidation reaction: introducing nitric oxide and oxygen into the reaction kettle in the step (1); stopping ventilation for 2-6h, controlling the temperature to be 0-20 ℃ in the ventilation process, and carrying out heat preservation reaction for 1-5 h at the temperature to obtain a reactant after the reaction is finished;
(3) Separating and distilling: standing the reactant in the step (2) for 0.5-1h, layering the reactant up and down, conveying an upper water phase to wastewater treatment, conveying a lower precipitate to a concentration kettle, and carrying out normal pressure distillation until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa, and controlling the distillation temperature to be 120-150 ℃ until the solvent is dried by the evaporated precipitate, thus obtaining the product 4-bromobiphenyl.
Under the catalysis of ionic liquid, zinc bromide and nitric oxide, the chemical formula of the preparation reaction of the 4-bromobiphenyl is as follows:
further, in the step (1), the molar ratio of the biphenyl to the solvent is 1:5-15, preferably 1:7.
Further, the solvent is dichloromethane or acetonitrile.
Further, in the step (1), the molar ratio of the biphenyl to the ionic liquid is 1:0.005-0.01, preferably 1:0.006.
Further, the ionic liquid is at least one of methyl imidazole tetrafluoroborate, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-butyl-3-methylimidazole tetrafluoroborate and 1, 3-dimethylimidazole tetrafluoroborate.
Further, in the step (1), the molar ratio of the biphenyl to the zinc bromide is 1:0.03-0.1, preferably 1:0.05.
Further, in step (1), the molar ratio of the biphenyl to the hydrobromic acid is 1:1.05-1.3, preferably 1:1.1.
Further, in the step (1), the flow rate of the introduced nitrogen is 1-2L/min.
Further, in the step (2), the molar ratio of the biphenyl to the nitric oxide introduced is 1:0.1-0.4, preferably 1:0.2.
Further, in the step (2), the molar ratio of the biphenyl to the oxygen introduced is 1:0.257-0.35, preferably 1:0.28.
The invention has the advantages that:
the invention provides a method for synthesizing 4-bromodiphenyl, which adopts diphenyl, hydrobromic acid and oxygen as reaction raw materials, and ionic liquid, zinc bromide and nitric oxide as catalysts to produce 4-bromodiphenyl by oxidation, has mild reaction conditions, does not have potential safety hazard, does not need to use a large amount of strong acid and strong alkali, avoids generating a large amount of byproduct salt, and reduces economic cost; meanwhile, the yield of the 4-bromodiphenyl oxide product is high, the product purity is high, the quality is good, and the preparation process is simple.
The specific embodiment is as follows:
the present invention will be described in further detail by way of examples.
Example 1: adding 462ml (7 mol) of methylene dichloride into a reaction kettle, adding 154g (1 mol) of biphenyl, 1g (0.006 mol) of methyl imidazole tetrafluoroborate, 11.25g (0.05 mol) of zinc bromide and 186g (1.1 mol) of 48% hydrobromic acid under stirring, after the material addition is finished, introducing nitrogen with the flow rate of 2L/min for 5min to replace air in the reaction kettle, cooling to 0-20 ℃ through a cooling medium, starting to simultaneously introduce 6g (0.2 mol) of nitric oxide and 9g (0.28 mol) of oxygen, stopping after 4h of ventilation, controlling the temperature to 0-20 ℃ in the ventilation process, and keeping the temperature for 3h of reaction at the temperature; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing the wastewater from an upper layer of water phase, conveying a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then, the distillation is carried out under reduced pressure, the vacuum degree is controlled to be more than or equal to 0.08mpa, the distillation temperature is controlled to be 120-150 ℃, until the methylene dichloride is evaporated and the precipitate is dried, 220g of the product 4-bromodiphenyl is obtained, the real yield is 94.42% (molar yield), and the purity is 99%.
The actual yield of the product 4-bromodiphenyl oxide prepared by the embodiment is obviously higher than that disclosed in the application number CN200810157467.1 and the name of the product 4-bromodiphenyl oxide is a preparation method of 4-bromodiphenyl oxide, and the product 4-bromodiphenyl oxide prepared by the embodiment has high purity and good quality.
Example 2: adding 660ml (10 mol) of methylene dichloride into a reaction kettle, adding 154g (1 mol) of biphenyl, 1.3g (0.008 mol) of methyl imidazole tetrafluoroborate, 18g (0.008 mol) of zinc bromide and 203g (1.2 mol) of 48% hydrobromic acid under stirring, after the material addition is finished, introducing nitrogen with the flow of 1L/min for 10min to replace air in the reaction kettle, cooling to 0-20 ℃ through a cooling medium, starting to simultaneously introduce 9g (0.3 mol) of nitric oxide and 11.52g (0.32 mol) of oxygen, stopping after 6h of ventilation, controlling the temperature to 0-20 ℃ in the ventilation process, and preserving the temperature for 5 h; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing the wastewater from an upper layer of water phase, conveying a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then, the distillation is carried out under reduced pressure, the vacuum degree is controlled to be more than or equal to 0.08mpa, the distillation temperature is controlled to be 120-150 ℃, until the methylene dichloride is evaporated and the precipitate is dried, 212g of the product 4-bromodiphenyl is obtained, the actual yield is 91% (molar yield), and the purity is 99%.
Example 3: adding 990ml (15 mol) of dichloromethane into a reaction kettle, adding 154g (1 mol) of biphenyl, 1.7g (0.01 mol) of methyl imidazole tetrafluoroborate, 22.5g (0.1 mol) of zinc bromide and 219.8g (1.3 mol) of 48% hydrobromic acid under stirring, after the addition, introducing nitrogen with the flow of 1.5L/min for 6min to replace the air in the reaction kettle, cooling to 0-20 ℃ through a cooling medium, starting to simultaneously introduce 12g (0.4 mol) of nitric oxide and 12.6g (0.35 mol) of oxygen, stopping after 2h of ventilation, controlling the temperature to 0-20 ℃ in the ventilation process, and preserving the temperature for 1 hour; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing the wastewater from an upper layer of water phase, conveying a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then, the distillation is carried out under reduced pressure, the vacuum degree is controlled to be more than or equal to 0.08mpa, the distillation temperature is controlled to be 120-150 ℃, until the methylene dichloride is evaporated and the precipitate is dried, 209.7g of the product 4-bromodiphenyl is obtained, the actual yield is 90% (molar yield), and the purity is 99%.
Example 4: adding 330ml (5 mol) of methylene dichloride into a reaction kettle, adding 154g (1 mol) of biphenyl, 0.85g (0.005 mol) of methyl imidazole tetrafluoroborate, 6.75g (0.03 mol) of zinc bromide and 177.5g (1.05 mol) of 48% hydrobromic acid under stirring, after the addition is finished, introducing nitrogen with the flow of 1.5L/min for 6min to replace air in the reaction kettle, cooling to 0-20 ℃ through a cooling medium, starting to simultaneously introduce 3g (0.1 mol) of nitric oxide, and stopping introducing 9.25g (0.257 mol) of oxygen after 2h of ventilation, controlling the temperature to be 0-20 ℃ in the ventilation process, and preserving the temperature for 1 hour; after the heat preservation is finished, standing for 1 hour, separating out a lower layer, removing the wastewater from an upper layer of water phase, conveying a lower layer of precipitate to a concentration kettle, and distilling at normal pressure until the distillation temperature reaches 80-120 ℃; then, the distillation is carried out under reduced pressure, the vacuum degree is controlled to be more than or equal to 0.08mpa, the distillation temperature is controlled to be 120-150 ℃, until the methylene dichloride is evaporated and the precipitate is dried, 205g of the product 4-bromodiphenyl is obtained, the actual yield is 88% (molar yield), and the purity is 99%.
The foregoing is a preferred embodiment of the present invention, and it will be apparent to those skilled in the art that modifications and variations can be made without departing from the principles of the present invention, and such modifications and variations are to be regarded as being within the scope of the invention.
Claims (8)
1. The synthesis method of the 4-bromodiphenyl is characterized by comprising the following steps in sequence:
(1) And (2) mixing and preparing: adding a solvent into a reaction kettle, stirring, then adding biphenyl, ionic liquid, zinc bromide and hydrobromic acid in the stirring process, and then introducing nitrogen for 5-10min to replace air in the reaction kettle; wherein the solvent is dichloromethane or acetonitrile; the ionic liquid is at least one of methyl tetrafluoroborate, 1-hexyl-3-methylimidazole tetrafluoroborate, 1-butyl-3-methylimidazole tetrafluoroborate and 1, 3-dimethylimidazole tetrafluoroborate;
(2) Oxidation reaction: introducing nitric oxide and oxygen into the reaction kettle in the step (1); stopping ventilation for 2-6h, controlling the temperature to be 0-20 ℃ in the ventilation process, and carrying out heat preservation reaction for 1-5 h at the temperature to obtain a reactant after the reaction is finished;
(3) Separating and distilling: standing the reactant in the step (2) for 0.5-1h, layering the reactant up and down, conveying an upper water phase to wastewater treatment, conveying a lower precipitate to a concentration kettle, and carrying out normal pressure distillation until the distillation temperature reaches 80-120 ℃; then carrying out reduced pressure distillation, controlling the vacuum degree to be more than or equal to 0.08mpa, and controlling the distillation temperature to be 120-150 ℃ until the solvent is dried by the evaporated precipitate, thus obtaining the product 4-bromobiphenyl.
2. The method for synthesizing 4-bromobiphenyl according to claim 1, wherein in step (1), the molar ratio of biphenyl to solvent is 1:5-15.
3. The method for synthesizing 4-bromobiphenyl according to claim 1, wherein in step (1), the molar ratio of the biphenyl to the ionic liquid is 1:0.005-0.01.
4. The method for synthesizing 4-bromodiphenyl according to claim 1, wherein in the step (1), the molar ratio of the diphenyl to the zinc bromide is 1:0.03-0.1.
5. The method for synthesizing 4-bromobiphenyl according to claim 1, wherein in step (1), the molar ratio of biphenyl to hydrobromic acid is 1:1.05-1.3.
6. The method for synthesizing 4-bromodiphenyl according to claim 1, wherein the flow rate of the nitrogen gas introduced in the step (1) is 1-2L/min.
7. The method for synthesizing 4-bromobiphenyl according to claim 1, wherein in step (2), the molar ratio of the biphenyl to the nitric oxide introduced is 1:0.1-0.4.
8. The method for synthesizing 4-bromobiphenyl according to claim 1, wherein in step (2), the molar ratio of the biphenyl to the oxygen introduced is 1:0.257-0.35.
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| CN202111639293.4A CN114195617B (en) | 2021-12-29 | 2021-12-29 | Synthesis method of 4-bromodiphenyl |
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| CN202111639293.4A CN114195617B (en) | 2021-12-29 | 2021-12-29 | Synthesis method of 4-bromodiphenyl |
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| CN114195617B true CN114195617B (en) | 2023-12-05 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004307461A (en) * | 2003-02-18 | 2004-11-04 | Sumitomo Chem Co Ltd | Method for producing biaryl compound |
| CN101376619A (en) * | 2008-10-08 | 2009-03-04 | 山东海王化工股份有限公司 | Preparation of 4-bromobiphenyl |
| CN112441900A (en) * | 2019-09-05 | 2021-03-05 | 浙江中科创越药业有限公司 | Preparation method of 4-biphenylacetic acid |
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- 2021-12-29 CN CN202111639293.4A patent/CN114195617B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004307461A (en) * | 2003-02-18 | 2004-11-04 | Sumitomo Chem Co Ltd | Method for producing biaryl compound |
| CN101376619A (en) * | 2008-10-08 | 2009-03-04 | 山东海王化工股份有限公司 | Preparation of 4-bromobiphenyl |
| CN112441900A (en) * | 2019-09-05 | 2021-03-05 | 浙江中科创越药业有限公司 | Preparation method of 4-biphenylacetic acid |
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