CN114181028B - Preparation method of phenylacetylene - Google Patents
Preparation method of phenylacetylene Download PDFInfo
- Publication number
- CN114181028B CN114181028B CN202111572771.4A CN202111572771A CN114181028B CN 114181028 B CN114181028 B CN 114181028B CN 202111572771 A CN202111572771 A CN 202111572771A CN 114181028 B CN114181028 B CN 114181028B
- Authority
- CN
- China
- Prior art keywords
- reaction
- bromostyrol
- phenylacetylene
- pressure
- collecting
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 29
- YMOONIIMQBGTDU-VOTSOKGWSA-N [(e)-2-bromoethenyl]benzene Chemical compound Br\C=C\C1=CC=CC=C1 YMOONIIMQBGTDU-VOTSOKGWSA-N 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 10
- 239000003054 catalyst Substances 0.000 claims abstract description 8
- 239000002994 raw material Substances 0.000 claims abstract description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims abstract description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
- 239000000706 filtrate Substances 0.000 claims description 8
- 238000004321 preservation Methods 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 238000007256 debromination reaction Methods 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 238000009413 insulation Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 230000007613 environmental effect Effects 0.000 abstract description 7
- 238000009776 industrial production Methods 0.000 abstract description 5
- 239000002699 waste material Substances 0.000 abstract description 3
- 239000012295 chemical reaction liquid Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000000463 material Substances 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000012065 filter cake Substances 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 238000005086 pumping Methods 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000003477 Sonogashira cross-coupling reaction Methods 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- VWFQXDQOONOJEQ-UHFFFAOYSA-N 1-ethynyl-2,3-dimethoxybenzene Chemical group COC1=CC=CC(C#C)=C1OC VWFQXDQOONOJEQ-UHFFFAOYSA-N 0.000 description 1
- -1 9, 10-diphenyl ethynyl anthracene series compounds Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001502 aryl halides Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000013064 chemical raw material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000005081 chemiluminescent agent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000007269 dehydrobromination reaction Methods 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 230000005298 paramagnetic effect Effects 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/26—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms
- C07C1/30—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from organic compounds containing only halogen atoms as hetero-atoms by splitting-off the elements of hydrogen halide from a single molecule
-
- 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
Abstract
The invention discloses a preparation method of phenylacetylene, which takes bromostyrol as a raw material and also as a reaction solvent, and under the condition of a catalyst, the system is heated for reaction, after the concentration of bromostyrol as a product is detected to be stable, the reaction is stopped, insoluble matters are removed by filtration, the reaction liquid is distilled at normal pressure, a fraction at 140-143 ℃ is collected, namely the product, the residual kettle residue is distilled at reduced pressure, and the fraction at 100-105 ℃ is collected for the next batch of reaction. The method has the advantages of simple operation, mild condition, less three wastes generated in the production process, low environmental protection pressure, low cost, high yield and the like, has wide application prospect, and is suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of biological medicine, in particular to a preparation method of phenylacetylene.
Background
Phenylacetylene is an important electronic chemical raw material and an organic synthesis intermediate, and phenylacetylene derivatives show excellent reaction characteristics in the synthesis and application of medicines, insect pheromone synthesis, electrode materials, chemiluminescent materials, new liquid crystal materials and the like, so that the phenylacetylene derivatives are widely paid attention. For example, dimethoxyphenylacetylene is a synthetic precursor of a natural drug; various substituted phenylacetylene containing fluorine substituent groups are excellent liquid crystal material intermediates; various substituted phenylacetylene can also be used for preparing good chemiluminescent materials.
Phenylacetylene is an intermediate necessary for preparing symmetrical aryne baseline condensed ring chemiluminescent agent, and its polymer polyphenylacetylene has the characteristics of photoconductive, electric conduction, paramagnetic, energy migration and conversion, etc., and is soluble and fusible, and its performance is stable, so that it is a novel conductive high-molecular material. The phenylacetylene of the company is mainly used for preparing 9, 10-diphenyl ethynyl anthracene series compounds, and the series compounds are fluorescent agent molecules most commonly used in POCl systems.
The preparation method of phenylacetylene has been reported, and comprehensive analysis is mainly carried out by the following four routes:
(1): and adding bromine into the styrene and then dehydrobrominating the styrene by using lithium amide. Its advantages are high output rate up to 90%. However, the lithium amide is prepared by the reaction of metal lithium and liquid ammonia, has strict condition requirements, and is difficult to realize industrial production.
(2): the beta-bromostyrene is prepared by melt reaction of beta-bromostyrene and potassium hydroxide solid. The method is a high-temperature reaction under the strong alkali condition, has high requirements on equipment materials, has serious equipment corrosion, high energy consumption and serious pollution, and has poor production operation feasibility. The yield is low and less than 50%.
(3): after brominating styrene, the methanol system is dehydrobrominated by potassium hydroxide at high temperature, and the product is obtained by steam distillation. The route has the advantages of high safety production risk due to severe heat release of dehydrobromination reaction, easy material spraying, high environmental protection pressure due to the fact that a large amount of high-concentration high-salt sewage is produced by steam distillation. The yield is low, the purity of the product is low, and the purity is about 96%.
(4): the catalyst is prepared from aryl halide and derivatives thereof serving as raw materials by using noble metals such as rhodium, platinum, palladium, nickel, ketone and the like as catalysts through a Sonogashira reaction or a modified Sonogashira coupling reaction. The method adopts the difficult pyridine/triethylamine mixed solvent, and the complex processes of decompression solvent removal, water washing, filtration, column chromatography separation, concentration, recrystallization and the like are adopted for post-treatment, so that the method is not beneficial to industrial production and environmental protection requirements. And noble metals such as palladium are used, so that the cost is high, and the industrialization application of the noble metals is severely limited.
Aiming at the defects of high safety and environmental protection pressure, high production cost, high equipment requirement and the like in the production process of the prior art, the preparation method of phenylacetylene disclosed by the invention has the advantages of simplicity in operation, mild conditions, few three wastes generated in the production process, low environmental protection pressure, low cost and the like, is suitable for industrial production, and has wide market prospect.
Disclosure of Invention
The invention aims to overcome the defects of high safety and environmental protection pressure, high production cost, high equipment requirement and the like in the prior art and provide a preparation method of phenylacetylene.
The preparation method of the invention comprises the following steps:
(1) Debromination reaction: the bromostyrol is taken as a raw material and also serves as a reaction solvent, the system is heated to react under the condition of a catalyst, the reaction is stopped after the heat preservation is carried out for more than 2 hours, and insoluble matters are removed by filtration.
Synthesis reaction equation of phenylacetylene
(2) And (3) collecting a finished product: and (3) distilling the filtrate in the step (1) at normal pressure, and collecting the fraction at 140-143 ℃ to obtain the phenylacetylene product, wherein the purity detected by a gas chromatography method is more than 98%.
(3) And (3) solvent sleeve: and (3) distilling the residual kettle residue in the step (2) under reduced pressure, and collecting a fraction at 100-105 ℃ which is bromostyrol, and applying the bromostyrol to the next reaction.
The catalyst in the step (1) is one or more of zinc powder, iron powder, aluminum powder, magnesium powder, tetrabutylammonium bromide, di-n-butylamine, tri-n-butylamine, triethylamine, sodium hydroxide, potassium hydroxide, sodium amide, lithium amide, sodium methoxide and sodium ethoxide, preferably zinc powder and iron powder.
The system in the step (1) is subjected to heat preservation reaction for more than 2 hours, and the reaction time is preferably 4-6 hours.
The reduced pressure distillation described in step (3) requires a pressure of less than-0.08 MP, preferably-0.08 to-0.1 MPa.
Compared with the prior art, the invention has the beneficial effects that:
1. the invention has simple operation, advanced process, less three wastes generated in the production process, small environmental protection pressure and almost clean production.
2. The method has mild reaction conditions, low equipment requirements and low production cost, and is suitable for industrial production.
3. The product yield is more than 80%, even more than 90%, and the GC purity is more than 98%.
Detailed Description
The advantages of the present invention will now be further described by the following examples, which are to be understood as being for illustrative purposes only and not limiting the scope of the present invention, as obvious variations and modifications thereof by persons skilled in the art are intended to be included within the scope of the present invention.
Embodiment one:
in a 250ml three-neck flask, 183g (1 mol) of bromostyrol, 39g (0.6 mol) of zinc powder, nitrogen protection, stirring uniformly, heating to 100 ℃ for reaction for 6 hours, stopping the reaction, filtering, pumping out a filter cake, distilling the filtrate at normal pressure, and collecting 88.2g of distillate at 140-143 ℃ to obtain phenylacetylene with 86.5% yield and 98.8% GC purity. The residual kettle residue is distilled under reduced pressure, the pressure is-0.095 MP, 17.3g of fraction at 100-105 ℃ is collected, and bromostyrol is used for the next experiment.
Embodiment two:
in a 250ml three-neck flask, 183g (1 mol) of bromostyrol, 33.6g (0.6 mol) of iron powder, nitrogen protection, stirring uniformly, heating to 100 ℃ for reaction for 6 hours under the heat preservation, stopping the reaction, filtering, draining a filter cake, distilling the filtrate at normal pressure, and collecting 82.1g of fraction at 140-143 ℃ to obtain phenylacetylene with the yield of 80.5% and the GC purity of 98.1%. The residual kettle residue is distilled under reduced pressure, the pressure is-0.095 MP, and 19.5g of fraction at 100-105 ℃ is collected, namely bromostyrol, and the bromostyrol is used for the next experiment.
Embodiment III:
in a 250ml three-neck flask, 183g (1 mol) of bromostyrol, 39g (0.6 mol) of zinc powder, nitrogen protection, stirring uniformly, heating to 120 ℃ for reaction for 6 hours under heat preservation, stopping the reaction, filtering, pumping out a filter cake, distilling the filtrate at normal pressure, and collecting 90.3g of distillate at 140-143 ℃ to obtain phenylacetylene with the yield of 88.5% and the GC purity of 98.9%. Distilling the residual kettle residue under reduced pressure, wherein the pressure is-0.095 MP, collecting 16.8g of fraction at 100-105 ℃ to obtain bromostyrol, and applying the bromostyrol to the next experiment.
Embodiment four:
in a 250ml three-neck flask, 183g (1 mol) of bromostyrol, 39g (0.6 mol) of zinc powder, nitrogen protection, stirring uniformly, heating to 120 ℃ for reaction for 8 hours under heat preservation, stopping the reaction, filtering, pumping out a filter cake, distilling the filtrate at normal pressure, and collecting 92.0g of fraction at 140-143 ℃ to obtain phenylacetylene with the yield of 90.2% and the GC purity of 99.1%. The residual kettle residue is distilled under reduced pressure, the pressure is-0.095 MP, and 13.1g of fraction at 100-105 ℃ is collected, namely bromostyrol, and the bromostyrol is used for the next experiment.
Fifth embodiment:
in a 250ml three-neck flask, 183g (1 mol) of bromostyrol, 80g (2.1 mol) of sodium amide, nitrogen protection, stirring uniformly, heating to 120 ℃ for reaction for 4 hours under the heat preservation, stopping the reaction, filtering, draining a filter cake, distilling the filtrate at normal pressure, and collecting 88.3g of distillate at 140-143 ℃ to obtain phenylacetylene with the yield of 86.6% and the GC purity of 98.9%. The residual kettle residue is distilled under reduced pressure, the pressure is-0.095 MP, and 18.8g of fraction at 100-105 ℃ is collected, namely bromostyrol, and the bromostyrol is used for the next experiment.
Example six:
in a 250ml three-neck flask, 183g (1 mol) of bromostyrol, 39g (0.6 mol) of zinc powder, 28g (0.5 mol) of potassium hydroxide, nitrogen protection, uniform stirring, heating to 120 ℃ for reaction for 6 hours, stopping the reaction, filtering, draining a filter cake, distilling the filtrate at normal pressure, and collecting 92.6g of distillate at 140-143 ℃ to obtain phenylacetylene with the yield of 90.8% and the GC purity of 99.5%. Distilling the residual kettle residue under reduced pressure, wherein the pressure is-0.095 MP, collecting 12.6g of fraction at 100-105 ℃ to obtain bromostyrol, and applying the bromostyrol to the next experiment.
It should be apparent that the above experimental examples are given for clarity of illustration only and are not limiting of the embodiments. Other variations or modifications of the above teachings will be apparent to those of ordinary skill in the art. It is not necessary here nor is it exhaustive of all embodiments. While still being apparent from variations or modifications that may be made by those skilled in the art are within the scope of the invention.
Claims (5)
1. A method for preparing phenylacetylene, comprising the following steps:
(1) Debromination reaction: bromostyrol is taken as a raw material and also serves as a reaction solvent, the system is heated to react under the condition of a catalyst, the reaction is stopped after the heat preservation is carried out for more than 2 hours, and insoluble substances are removed by filtration; the catalyst is one or more of zinc powder, iron powder, aluminum powder and magnesium powder; the system is heated for reaction, and the temperature range is 50-250 ℃;
(2) And (3) collecting a finished product: distilling the filtrate in the step (1) at normal pressure, and collecting fractions at 140-143 ℃ to obtain phenylacetylene;
(3) And (3) solvent sleeve: distilling the residual kettle residue in the step (2) under reduced pressure, and collecting a fraction at 100-105 ℃ which is bromostyrol, and applying the bromostyrol to the next reaction; the pressure is lower than-0.08 MP.
2. The preparation method of claim 1, wherein the catalyst is zinc powder or iron powder.
3. The method according to claim 1, wherein the system in step (1) is heated to 120-140 ℃.
4. The preparation method of claim 1, wherein the system in the step (1) is subjected to thermal insulation reaction for 4-6 hours.
5. The method according to claim 1, wherein the reduced pressure distillation in the step (3) is carried out at a pressure of-0.08 to-0.1 MP.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111572771.4A CN114181028B (en) | 2021-12-21 | 2021-12-21 | Preparation method of phenylacetylene |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202111572771.4A CN114181028B (en) | 2021-12-21 | 2021-12-21 | Preparation method of phenylacetylene |
Publications (2)
Publication Number | Publication Date |
---|---|
CN114181028A CN114181028A (en) | 2022-03-15 |
CN114181028B true CN114181028B (en) | 2023-10-24 |
Family
ID=80605772
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202111572771.4A Active CN114181028B (en) | 2021-12-21 | 2021-12-21 | Preparation method of phenylacetylene |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN114181028B (en) |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56133227A (en) * | 1980-03-24 | 1981-10-19 | Sanyo Chem Ind Ltd | Preparation of phenylacetylene |
JPS62145030A (en) * | 1985-12-18 | 1987-06-29 | Denki Kagaku Kogyo Kk | Production of phenylacetylene compound |
CN112457148A (en) * | 2020-12-03 | 2021-03-09 | 珠海固瑞泰复合材料有限公司 | Method for synthesizing high-purity MDPES (methyl diphenylsulfone) raw material phenyl acetylene in one step |
CN112608209A (en) * | 2020-12-03 | 2021-04-06 | 珠海固瑞泰复合材料有限公司 | Green method for synthesizing MDPES raw material phenylacetylene without solvent |
-
2021
- 2021-12-21 CN CN202111572771.4A patent/CN114181028B/en active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56133227A (en) * | 1980-03-24 | 1981-10-19 | Sanyo Chem Ind Ltd | Preparation of phenylacetylene |
JPS62145030A (en) * | 1985-12-18 | 1987-06-29 | Denki Kagaku Kogyo Kk | Production of phenylacetylene compound |
CN112457148A (en) * | 2020-12-03 | 2021-03-09 | 珠海固瑞泰复合材料有限公司 | Method for synthesizing high-purity MDPES (methyl diphenylsulfone) raw material phenyl acetylene in one step |
CN112608209A (en) * | 2020-12-03 | 2021-04-06 | 珠海固瑞泰复合材料有限公司 | Green method for synthesizing MDPES raw material phenylacetylene without solvent |
Non-Patent Citations (4)
Title |
---|
Belletire,John L.等.Sodium Amide.e-EROS Encyclopedia of Reagents for Organic Synthesis.2001,第1-4页. * |
Direct Formation of Organocopper Compounds by Oxidative Addition of Zerovalent Copper to Organic Halides;Greg W. Ebert等;J. Org. Chem.;第49卷(第26期);第5280-5282页 * |
Sodium Diisopropylamide-Mediated Dehydrohalogenations: Influence of Primary- and Secondary-Shell Solvation;Yun Ma等;J. Org. Chem.;第84卷;第10860-10869页 * |
中国商品大辞典编辑委员会.《中国商品大辞典:化学试剂分册》.中国商业出版社,1994,(第1版),第1304页. * |
Also Published As
Publication number | Publication date |
---|---|
CN114181028A (en) | 2022-03-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN102093209A (en) | Method for preparing aromatic dimethyl chloride | |
CN109535109A (en) | A kind of method that the liquefaction of wood fibre orientation prepares 5 hydroxymethyl furfural | |
Fang et al. | Preparation of fluorinated biaryls through direct palladium-catalyzed coupling of polyfluoroarenes with aryltrifluoroborates | |
CN114181028B (en) | Preparation method of phenylacetylene | |
CN105037138A (en) | Preparation method for 2,9-dibutyl sebacate | |
CN105198707B (en) | The synthetic method of 4 biphenylmethanols | |
CN103333143B (en) | Preparation method of high-purity benzbromarone | |
CN102633768B (en) | Method for transforming cisconfiguration of oxane compounds to transconfiguration | |
CN101492351A (en) | Process for producing asarin | |
CN112608209A (en) | Green method for synthesizing MDPES raw material phenylacetylene without solvent | |
CN112457148A (en) | Method for synthesizing high-purity MDPES (methyl diphenylsulfone) raw material phenyl acetylene in one step | |
CN103193660B (en) | Synthetic method of 4-alkoxy phenylamine compound | |
CN110437069B (en) | Continuous synthesis method of 2-fluoro-malonic diester compound | |
CN114293210A (en) | Method for continuously electrosynthesis of benzopyran-4-ketone by using micro-reaction device | |
CN104262081A (en) | Method utilizing gas-phase hexachloro-1,3-butadiene to prepare hexachloroethane | |
CN111099955B (en) | Method and device for producing deuterated aromatic ring compound safely, environmentally and cheaply | |
CN103086898A (en) | Preparation method of diphenylamine or ring-substituted derivative thereof | |
CN107382640B (en) | β -aryl phenylpropanone compound synthesis method | |
Chakravarthy et al. | A highly efficient synthesis of 1-trimethylsilyl-2-arylcyclopentenes using two consecutive stages of aqueous and anhydrous reactions | |
CN109422634A (en) | A kind of synthetic method of 3- carbonyl indanone compounds | |
CN112225657B (en) | Preparation method of flurbiprofen | |
CN116120161B (en) | Process for treating rectification residues of 2-ethyl anthraquinone and recovering 2-ethyl anthraquinone | |
CN103449974A (en) | Preparation method of 4-trans-(4'-bromine-biphenylyl-4-yl)-cyclohexanol | |
CN102464626A (en) | Method for preparing 5-(4-(N,N-diphenyl-amino) phenmethylene)-3-(2-phenethyl)-2,4-oxazolidinedione | |
CN115142077B (en) | Application of electrochemical microchannel reaction device in 1, 2-alkynyl migration reaction |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |