JPH0353308B2 - - Google Patents

Info

Publication number: JPH0353308B2
Authority: JP; Japan
Prior art keywords: reaction; polyene; platinum; gas; epoxy compound
Prior art date: 1984-02-17
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.): Expired - Lifetime

Application number

JP59026959A

Other languages

English (en)

Japanese (ja)

Other versions

JPS60197664A (ja

Inventor

Iwao Tabuse

Kozo Morimitsu

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1984-02-17

Filing date

1984-02-17

Publication date

1991-08-14

1984-02-17 Application filed by Individual filed Critical Individual

1984-02-17 Priority to JP59026959A priority Critical patent/JPS60197664A/ja

1985-10-07 Publication of JPS60197664A publication Critical patent/JPS60197664A/ja

1991-08-14 Publication of JPH0353308B2 publication Critical patent/JPH0353308B2/ja

Status Granted legal-status Critical Current

Links

BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 40
229910052751 metal Inorganic materials 0.000 claims description 29
239000002184 metal Substances 0.000 claims description 29
150000004032 porphyrins Chemical class 0.000 claims description 22
229910052697 platinum Inorganic materials 0.000 claims description 20
150000001875 compounds Chemical class 0.000 claims description 19
239000004593 Epoxy Substances 0.000 claims description 18
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 17
150000004291 polyenes Chemical class 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 11
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 10
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
239000007791 liquid phase Substances 0.000 claims description 7
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
-1 acetoxyl group Chemical group 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 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
238000006243 chemical reaction Methods 0.000 description 23
239000000084 colloidal system Substances 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 12
239000007789 gas Substances 0.000 description 12
239000003054 catalyst Substances 0.000 description 11
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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
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
239000002245 particle Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 7
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
235000002597 Solanum melongena Nutrition 0.000 description 6
239000000203 mixture Substances 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
150000002460 imidazoles Chemical class 0.000 description 5
238000005481 NMR spectroscopy 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
238000004458 analytical method Methods 0.000 description 3
239000012298 atmosphere Substances 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
ZVAVDTDDBJNPJQ-UHFFFAOYSA-N ethanol;platinum Chemical compound [Pt].CCO ZVAVDTDDBJNPJQ-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
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
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 2
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 2
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
ICJOOVLSDYCSCJ-VQHVLOKHSA-N [(e)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl] acetate Chemical compound CC(=O)OC\C=C(/C)CCC1OC1(C)C ICJOOVLSDYCSCJ-VQHVLOKHSA-N 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
JYJVVHFRSFVEJM-UHFFFAOYSA-N iodosobenzene Chemical compound O=IC1=CC=CC=C1 JYJVVHFRSFVEJM-UHFFFAOYSA-N 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000002994 raw material Substances 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 1,2-dimethoxyethane;hydrate Chemical compound O.COCCOC ZWNCJCPLPUBNCZ-UHFFFAOYSA-N 0.000 description 1
QYIMSPSDBYKPPY-BANQPHDMSA-N 2,3-epoxysqualene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC1OC1(C)C QYIMSPSDBYKPPY-BANQPHDMSA-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
WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000003638 chemical reducing agent Substances 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
230000001590 oxidative effect Effects 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
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)

JP59026959A 1984-02-17 1984-02-17 エポキシ化合物の製造方法 Granted JPS60197664A (ja)

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 JPS60197664A (ja)	1985-10-07
JPH0353308B2 true JPH0353308B2 (da)	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 (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
Title
J.AMER.CHEM.SOC.,=1981 *

Also Published As

Publication number	Publication date
JPS60197664A (ja)	1985-10-07

Publication	Publication Date	Title
Fujita et al.	2004	In situ Formation of Peracetic Acid in Iron‐Catalyzed Epoxidations by Hydrogen Peroxide in the Presence of Acetic Acid
Ishii et al.	1990	A novel oxidation of internal alkynes with hydrogen peroxide catalyzed by peroxotungsten compounds
Hâncu et al.	2002	H2O2 in CO2/H2O biphasic systems: Green synthesis and epoxidation reactions
Barak et al.	1988	Selective oxidation of alcohols by a H2O2-RuCl3 system under phase-transfer conditions
JP2000202291A (ja)	2000-07-25	新規触媒、過酸化水素の製造方法、及び酸化工程での過酸化水素の使用
Blanco-Brieva et al.	2008	New two-step process for propene oxide production (HPPO) based on the direct synthesis of hydrogen peroxide
JPH06321924A (ja)	1994-11-22	マンガン錯体によるオレフィン類のエポキシ化方法
Dell'Anna et al.	1996	Aerobic oxidation of sulfides catalysed by cobalt (II) complexes under homogeneous and heterogeneous conditions
Foglia et al.	1977	Oxidation of alkenes with use of phase transfer catalysis
Santacesaria et al.	2003	Double bond oxidative cleavage of monoenic fatty chains
Brown et al.	1986	Organoboranes for synthesis. 4: Oxidation of organoboranes with pyridinium chlorochromate. A direct synthesis of aldehydes from terminal alkenes via hydroboration
JPS6142725B2 (da)	1986-09-24
JP2001523261A (ja)	2001-11-20	ホスフェート安定化パーオキソタングステート化合物を触媒として用いるエポキシ化方法
JP4083424B2 (ja)	2008-04-30	オレフィンのエポキシ化方法
TW201136907A (en)	2011-11-01	Epoxidation of an olefin
JP3128650B2 (ja)	2001-01-29	水素と酸素による直接的な水酸化芳香族化合物の製造方法
JPH0353308B2 (da)	1991-08-14
RU2542583C2 (ru)	2015-02-20	Получение эпоксиэтилкарбоксилата или глицидилкарбоксилата
Brunet et al.	1978	Activation of reducing agents. Sodium hydride containing complex reducing agents. 9. Ketone and aldehyde reductions
Murphy et al.	2002	Advances in homogeneous and heterogeneous catalytic aerobic oxidation of isophorone to ketoisophorone
CN1176749C (zh)	2004-11-24	氢氧气氛中丙烯环氧化制环氧丙烷催化剂及制备工艺
EP0013797B1 (en)	1982-12-01	Oxidation of alcohols and aldehydes using a ruthenate catalyst
Salles et al.	2000	Comparison of oxoperoxophosphatotungstate phase transfer catalysis with methyltrioxorhenium two-phase catalysis for epoxidation by hydrogen peroxide
JP2008019265A (ja)	2008-01-31	β−ヒドロキシヒドロペルオキシド類の製造法とその触媒
JP2003192680A (ja)	2003-07-09	環状モノオレフィンのエポキシ化方法