CN114981482A - 环氧化合物的制造方法 - Google Patents
环氧化合物的制造方法 Download PDFInfo
- Publication number
- CN114981482A CN114981482A CN202080075921.8A CN202080075921A CN114981482A CN 114981482 A CN114981482 A CN 114981482A CN 202080075921 A CN202080075921 A CN 202080075921A CN 114981482 A CN114981482 A CN 114981482A
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- Prior art keywords
- epoxy compound
- ion
- formula
- olefin
- ions
- Prior art date
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- 239000004593 Epoxy Substances 0.000 title claims abstract description 98
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 31
- -1 peracid ion Chemical class 0.000 claims abstract description 74
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 65
- 150000001336 alkenes Chemical class 0.000 claims abstract description 63
- 150000003839 salts Chemical class 0.000 claims abstract description 56
- 239000008346 aqueous phase Substances 0.000 claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 32
- 229910002091 carbon monoxide Inorganic materials 0.000 claims abstract description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims description 35
- 150000004696 coordination complex Chemical class 0.000 claims description 29
- 229910052751 metal Inorganic materials 0.000 claims description 23
- 239000002184 metal Substances 0.000 claims description 23
- 239000012071 phase Substances 0.000 claims description 21
- 230000003647 oxidation Effects 0.000 claims description 20
- 230000001590 oxidative effect Effects 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 11
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 9
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 abstract description 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000002848 electrochemical method Methods 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000003446 ligand Substances 0.000 description 19
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- 229910052801 chlorine Inorganic materials 0.000 description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 13
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- 125000000623 heterocyclic group Chemical group 0.000 description 11
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
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- 125000000217 alkyl group Chemical group 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 230000007797 corrosion Effects 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 125000005647 linker group Chemical group 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 230000001737 promoting effect Effects 0.000 description 3
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- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000002815 homogeneous catalyst Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
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- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
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- 229910052725 zinc Inorganic materials 0.000 description 2
- 125000006661 (C4-C6) heterocyclic group Chemical group 0.000 description 1
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- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 241001590997 Moolgarda engeli Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B1/00—Electrolytic production of inorganic compounds or non-metals
- C25B1/01—Products
- C25B1/28—Per-compounds
- C25B1/30—Peroxides
-
- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/23—Oxidation
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- Materials Engineering (AREA)
- Metallurgy (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Electrolytic Production Of Non-Metals, Compounds, Apparatuses Therefor (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2019-196508 | 2019-10-29 | ||
| JP2019196508A JP7327758B2 (ja) | 2019-10-29 | 2019-10-29 | エポキシ化合物の製造方法 |
| PCT/JP2020/039561 WO2021085268A1 (ja) | 2019-10-29 | 2020-10-21 | エポキシ化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114981482A true CN114981482A (zh) | 2022-08-30 |
| CN114981482B CN114981482B (zh) | 2024-07-26 |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5974285A (ja) * | 1982-10-19 | 1984-04-26 | Asahi Chem Ind Co Ltd | ヘキサフルオロプロピレンのエポキシ化方法 |
| US4490222A (en) * | 1982-04-30 | 1984-12-25 | Imperial Chemical Industries Plc | Preparation of selected epoxides |
| US5329024A (en) * | 1993-03-30 | 1994-07-12 | National Starch And Chemical Investment Holding Corporation | Epoxidation of olefins via certain manganese complexes |
| JPH09249984A (ja) * | 1996-03-13 | 1997-09-22 | Otsuka Chem Co Ltd | 光学活性エポキシド誘導体の製造方法 |
| JP2003340286A (ja) * | 2002-05-23 | 2003-12-02 | Kao Corp | エポキシ化触媒 |
| CN102877086A (zh) * | 2012-09-13 | 2013-01-16 | 华南理工大学 | 以烯烃与二氧化碳为原料电化学法制备环状碳酸酯的方法 |
| CN105745195A (zh) * | 2013-11-15 | 2016-07-06 | 康宁股份有限公司 | 氧化烯合成 |
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4490222A (en) * | 1982-04-30 | 1984-12-25 | Imperial Chemical Industries Plc | Preparation of selected epoxides |
| JPS5974285A (ja) * | 1982-10-19 | 1984-04-26 | Asahi Chem Ind Co Ltd | ヘキサフルオロプロピレンのエポキシ化方法 |
| US5329024A (en) * | 1993-03-30 | 1994-07-12 | National Starch And Chemical Investment Holding Corporation | Epoxidation of olefins via certain manganese complexes |
| JPH09249984A (ja) * | 1996-03-13 | 1997-09-22 | Otsuka Chem Co Ltd | 光学活性エポキシド誘導体の製造方法 |
| JP2003340286A (ja) * | 2002-05-23 | 2003-12-02 | Kao Corp | エポキシ化触媒 |
| CN102877086A (zh) * | 2012-09-13 | 2013-01-16 | 华南理工大学 | 以烯烃与二氧化碳为原料电化学法制备环状碳酸酯的方法 |
| CN105745195A (zh) * | 2013-11-15 | 2016-07-06 | 康宁股份有限公司 | 氧化烯合成 |
Non-Patent Citations (2)
| Title |
|---|
| HIDEO TANAKA ET AL: "Electrochemical asymmetric epoxidation of olefins by using an optically active Mn-salen complex", JOURNAL OF ELECTROANALYTICAL CHEMISTRY, vol. 507, pages 75 * |
| HO KAM PIU: "Some New Approaches to Alkene Epoxidation with Manganese Catalyst", 香港理工大学 博士学位论文, pages 1 - 236 * |
Also Published As
| Publication number | Publication date |
|---|---|
| TW202124402A (zh) | 2021-07-01 |
| WO2021085268A1 (ja) | 2021-05-06 |
| JP2021070835A (ja) | 2021-05-06 |
| JP7327758B2 (ja) | 2023-08-16 |
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