JPS60197664A - エポキシ化合物の製造方法 - Google Patents
エポキシ化合物の製造方法Info
- Publication number
- JPS60197664A JPS60197664A JP59026959A JP2695984A JPS60197664A JP S60197664 A JPS60197664 A JP S60197664A JP 59026959 A JP59026959 A JP 59026959A JP 2695984 A JP2695984 A JP 2695984A JP S60197664 A JPS60197664 A JP S60197664A
- Authority
- JP
- Japan
- Prior art keywords
- polyene
- epoxy compound
- platinum
- methylimidazole
- selectivity
- 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.)
- Granted
Links
- 239000004593 Epoxy Substances 0.000 title claims abstract description 29
- 150000001875 compounds Chemical class 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 50
- 229910052751 metal Inorganic materials 0.000 claims abstract description 29
- 239000002184 metal Substances 0.000 claims abstract description 29
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 25
- 150000004032 porphyrins Chemical class 0.000 claims abstract description 21
- 150000004291 polyenes Chemical class 0.000 claims abstract description 20
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 13
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007791 liquid phase Substances 0.000 claims abstract description 8
- 239000001301 oxygen Substances 0.000 claims abstract description 7
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 230000001590 oxidative effect Effects 0.000 claims abstract description 5
- -1 polyene compound Chemical class 0.000 claims abstract description 5
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 16
- 150000002460 imidazoles Chemical class 0.000 claims description 7
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 11
- 230000009257 reactivity Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000084 colloidal system Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 12
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 10
- 229910001882 dioxygen Inorganic materials 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 8
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000002245 particle Substances 0.000 description 8
- ZGIGZINMAOQWLX-NCZFFCEISA-N 3,7,11-Trimethyl-2,6,10-dodecatrienyl acetate Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\COC(C)=O ZGIGZINMAOQWLX-NCZFFCEISA-N 0.000 description 6
- ZGIGZINMAOQWLX-UHFFFAOYSA-N Farnesyl acetate Natural products CC(C)=CCCC(C)=CCCC(C)=CCOC(C)=O ZGIGZINMAOQWLX-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 229940007703 farnesyl acetate Drugs 0.000 description 6
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 5
- 239000005792 Geraniol Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000004817 gas chromatography Methods 0.000 description 5
- 229940113087 geraniol Drugs 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 3
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229940031439 squalene Drugs 0.000 description 3
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 3
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- ZVAVDTDDBJNPJQ-UHFFFAOYSA-N ethanol;platinum Chemical compound [Pt].CCO ZVAVDTDDBJNPJQ-UHFFFAOYSA-N 0.000 description 2
- JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- KXDDDNKGVUBFQS-UHFFFAOYSA-N (2R,3R)-2,3-epoxy-3,7-dimethyl-6-octenal Natural products CC(C)=CCCC1(C)OC1C=O KXDDDNKGVUBFQS-UHFFFAOYSA-N 0.000 description 1
- SWYACUITMIHYDS-SOFGYWHQSA-N (e)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-en-1-ol Chemical compound OC\C=C(/C)CCC1OC1(C)C SWYACUITMIHYDS-SOFGYWHQSA-N 0.000 description 1
- ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- GLZPCOQZEFWAFX-JXMROGBWSA-N Nerol Natural products CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 102000011759 adducin Human genes 0.000 description 1
- 108010076723 adducin Proteins 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Epoxy Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59026959A JPS60197664A (ja) | 1984-02-17 | 1984-02-17 | エポキシ化合物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59026959A JPS60197664A (ja) | 1984-02-17 | 1984-02-17 | エポキシ化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60197664A true JPS60197664A (ja) | 1985-10-07 |
| JPH0353308B2 JPH0353308B2 (th) | 1991-08-14 |
Family
ID=12207693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59026959A Granted JPS60197664A (ja) | 1984-02-17 | 1984-02-17 | エポキシ化合物の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60197664A (th) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR1001349B (el) * | 1992-08-18 | 1993-10-29 | Athanasios Koutsolelos | Μέ?οδος ανακύκλωσης-μετατροπής πολυμερικών ουσιών (πλαστικών) στα αντίστοιχα εποξείδια & πολυαι?έρες τους με καταλυτική δράση πορφυρινών,παρουσία δοτών οξυγόνου & μετατροπή των πολυεποξειδίων σε πολυαλκοόλες & πολυαι?έρες. |
| CN111135871A (zh) * | 2020-01-07 | 2020-05-12 | 西北大学 | 一种咪唑离子液体功能化的锌卟啉及其应用 |
-
1984
- 1984-02-17 JP JP59026959A patent/JPS60197664A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| J.AMER.CHEM.SOC.,=1981 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR1001349B (el) * | 1992-08-18 | 1993-10-29 | Athanasios Koutsolelos | Μέ?οδος ανακύκλωσης-μετατροπής πολυμερικών ουσιών (πλαστικών) στα αντίστοιχα εποξείδια & πολυαι?έρες τους με καταλυτική δράση πορφυρινών,παρουσία δοτών οξυγόνου & μετατροπή των πολυεποξειδίων σε πολυαλκοόλες & πολυαι?έρες. |
| CN111135871A (zh) * | 2020-01-07 | 2020-05-12 | 西北大学 | 一种咪唑离子液体功能化的锌卟啉及其应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0353308B2 (th) | 1991-08-14 |
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