JPH0495079A - Production of compound containing epoxy group - Google Patents
Production of compound containing epoxy groupInfo
- Publication number
- JPH0495079A JPH0495079A JP2212459A JP21245990A JPH0495079A JP H0495079 A JPH0495079 A JP H0495079A JP 2212459 A JP2212459 A JP 2212459A JP 21245990 A JP21245990 A JP 21245990A JP H0495079 A JPH0495079 A JP H0495079A
- Authority
- JP
- Japan
- Prior art keywords
- group
- containing compound
- epoxy group
- general formula
- nickel
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 36
- 125000003700 epoxy group Chemical group 0.000 title claims description 26
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- -1 aldehyde compound Chemical class 0.000 claims abstract description 31
- 125000003118 aryl group Chemical group 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims abstract description 7
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940078494 nickel acetate Drugs 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 150000002816 nickel compounds Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 27
- FAVBVYLIENPQLG-UHFFFAOYSA-N 2-methyldec-2-ene Chemical compound CCCCCCCC=C(C)C FAVBVYLIENPQLG-UHFFFAOYSA-N 0.000 abstract description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 20
- 239000002904 solvent Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- AFFLGGQVNFXPEV-UHFFFAOYSA-N 1-decene Chemical compound CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- 150000002815 nickel Chemical class 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FTZILAQGHINQQR-UHFFFAOYSA-N 2-Methylpentanal Chemical compound CCCC(C)C=O FTZILAQGHINQQR-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 2
- 229910001882 dioxygen Inorganic materials 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
- 150000001451 organic peroxides Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 150000004965 peroxy acids Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
- ILPBINAXDRFYPL-HWKANZROSA-N (E)-2-octene Chemical compound CCCCC\C=C\C ILPBINAXDRFYPL-HWKANZROSA-N 0.000 description 1
- ILPBINAXDRFYPL-HYXAFXHYSA-N (Z)-2-octene Chemical compound CCCCC\C=C/C ILPBINAXDRFYPL-HYXAFXHYSA-N 0.000 description 1
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 1
- UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- IQVAERDLDAZARL-UHFFFAOYSA-N 2-phenylpropanal Chemical compound O=CC(C)C1=CC=CC=C1 IQVAERDLDAZARL-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- SJPDIYSLQXNOQB-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=C[CH]CC1=CC=CC=C1 SJPDIYSLQXNOQB-UHFFFAOYSA-N 0.000 description 1
- RKDQFNLPHKSPGL-UHFFFAOYSA-N 4-diethoxyphosphorylphenol Chemical compound CCOP(=O)(OCC)C1=CC=C(O)C=C1 RKDQFNLPHKSPGL-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N beta-phenylpropionaldehyde Natural products O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ILPBINAXDRFYPL-UHFFFAOYSA-N cis-octene-2 Natural products CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- BGEHHAVMRVXCGR-UHFFFAOYSA-N methylundecylketone Natural products CCCCCCCCCCCCC=O BGEHHAVMRVXCGR-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- CZPZWMPYEINMCF-UHFFFAOYSA-N propaneperoxoic acid Chemical compound CCC(=O)OO CZPZWMPYEINMCF-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 239000010457 zeolite Substances 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
- Epoxy Compounds (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〈産業上の利用分野〉
本発明はエポキシ基含有化合物の製造方法に関し、特に
ニッケル化合物とアルデヒド化合物の併存下に行なう新
規な反応により、エポキシ基含有化合物を得ることがで
きる方法に関する。[Detailed Description of the Invention] <Industrial Application Field> The present invention relates to a method for producing an epoxy group-containing compound, and particularly to a method for producing an epoxy group-containing compound by a novel reaction conducted in the coexistence of a nickel compound and an aldehyde compound. Regarding how it can be done.
〈従来の技術〉
従来、エポキシ基含有化合物を製造する方法として、二
重結合を有する化合物を、ベンゼン、クロロホルムある
いは四塩化炭素などの不活性溶媒中で、過安息香酸、過
ギ酸、過フタル酸、過プロピオン酸、過酷酸あるいはト
リフルオロ過酢酸などの有機過酸化物で酸化する方法が
知られている。 特に、工業的には、過酸化物を生じさ
せる物質、例えば氷酢駿と不飽和化合物との混合物に、
強酸触媒を加えて６０〜７０℃に加熱しながら過酸化水
素を加えて過酢酸を生成させ、この過酢酸を利用してエ
ポキシ基含有化合物を製造する方法が行われている。<Prior art> Conventionally, as a method for producing epoxy group-containing compounds, a compound having a double bond is mixed with perbenzoic acid, performic acid, or perphthalic acid in an inert solvent such as benzene, chloroform, or carbon tetrachloride. A method of oxidizing with an organic peroxide such as perpropionic acid, harsh acid or trifluoroperacetic acid is known. In particular, industrially, peroxide-forming substances, such as mixtures of ice vinegar and unsaturated compounds, are
A method of producing an epoxy group-containing compound is carried out by adding a strong acid catalyst and heating to 60 to 70°C, adding hydrogen peroxide to produce peracetic acid, and using this peracetic acid.
〈発明が解決しようとする課題〉
しかしながら、前記方法における反応は、過敏な反応で
あるため、選択的にエポキシ化反応を行うことが困難で
あり、しかもエポキシ基含有化合物の生成に伴って、生
成したエポキシ基含有化合物の一部が重合することがあ
る。 また、この反応は、反応温度が５０℃以上の厳し
い反応条件下で行なわれるため、副反応が生起し易く、
エポキシ基含有化合物を高酸′率で得ることができない
。 また酸化剤として使用する過酸類は高価かつ取扱い
が危険なものであるため、工業的に高コストになるとい
う不利がある。<Problems to be Solved by the Invention> However, since the reaction in the above method is a sensitive reaction, it is difficult to perform the epoxidation reaction selectively, and moreover, as the epoxy group-containing compound is produced, A part of the epoxy group-containing compound may polymerize. In addition, since this reaction is carried out under severe reaction conditions at a reaction temperature of 50°C or higher, side reactions are likely to occur.
It is not possible to obtain an epoxy group-containing compound with a high acid content. In addition, the peracids used as oxidizing agents are expensive and dangerous to handle, so they have the disadvantage of increasing industrial costs.
さらに、有機過酸化物を使用しないエポキシ基含有化合
物の製造方法として、不飽和化合物に次亜ハロゲン酸を
使用してへロヒドリンを生成させ、次いでこのへロヒド
リンをアルカリ処理し、エポキシ基を生成する方法も知
られているが、この方法は、構造の複雑なオレフィン類
には適用できない。Furthermore, as a method for producing an epoxy group-containing compound without using an organic peroxide, hypohalous acid is used for an unsaturated compound to generate herohydrin, and then this herohydrin is treated with an alkali to generate an epoxy group. A method is also known, but this method cannot be applied to structurally complex olefins.
そこで本発明の目的は、従来この種のエポキシ基含有化
合物の製造に用いられてきた反応に比して温和な反応条
件で行なうことができ、過酸類等の高価な酸化剤を使用
しないため工業的に低コストで行なうことができ、また
良好な触媒効率で、エポキシ基含有化合物を得ることが
できる新蜆な方法を提供することにある。Therefore, an object of the present invention is that it can be carried out under milder reaction conditions compared to the reactions conventionally used for producing this type of epoxy group-containing compound, and that it does not require the use of expensive oxidizing agents such as peracids. The object of the present invention is to provide a new method that can be carried out at low cost and can obtain an epoxy group-containing compound with good catalytic efficiency.
く課題を解決するための手段〉
本発明は、前記課題を解決するために、−船蔵（１）：
［式中、Ｒ１は直鎖または分岐状のアルキル基、アリー
ル基であり、置換基を有していてもよく、Ｒ２およびＲ
３は同一でも異なってもよく、水素原子、置換あるいは
非置換のアルキル基またはアリール基であり、相互に結
合して環を形成し
ていでもよく、またＲ１とＲ３は、相互に結合して環を
形成していてもよく、さらにＲ’ Ｒ”およびＲ３は
、同時に結合して縮合環を形成していてもよい］
で表される二重結合含有化合物を、酢酸ニッケルおよび
／またはニッケル錯体からなる触媒と、下記−船蔵（■
）：
Ｒ７ＣＨＯ（ｎ ）
［ここで、Ｒγは直鎖または分岐状のアルキル基、もし
くはアリール基であり、置換基を有していてもよい］
で表わされるアルデヒド化合物との存在下に、酸素含有
ガスと反応させる工程を含む、−船蔵（■）：
［Ｒ１Ｒ２およびＲ３は前記−船蔵（Ｉ）において定義
したとおりである］
で表されるエポキシ基含有化合物の製造方法提供するも
のである。Means for Solving the Problems> In order to solve the above problems, the present invention provides - Funazura (1): [wherein R1 is a linear or branched alkyl group or aryl group, and a substituent may have R2 and R
3 may be the same or different, and represent a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group, and may be bonded to each other to form a ring, and R1 and R3 may be bonded to each other to form a ring. R'R'' and R3 may be bonded together to form a condensed ring. The catalyst and the following - Funagura (■
): R7CHO(n) [Here, Rγ is a linear or branched alkyl group or an aryl group, and may have a substituent] In the presence of an aldehyde compound represented by Provided is a method for producing an epoxy group-containing compound represented by -Funazo (■): [R1R2 and R3 are as defined in -Funazo (I) above], including a step of reacting with a gas. .
以下、本発明のエポキシ基含有化合物の製造方法につい
て詳細に説明する。Hereinafter, the method for producing the epoxy group-containing compound of the present invention will be explained in detail.
本発明の出発物質である二重結合含有化合物を表わす一
般式（Ｉ）において、Ｒ’は直鎖または分岐状のアルキ
ル基またはアリール基であり、置換基を有していてもよ
い、 Ｒ１の直鎖または分岐状のアルキル基としては、
例えば、エチル基、ｎ−プロピル基、ｎ−ブチル基、５
ｅｃ−ブチル基、ｔｅｒｔ−ブチル基、ｎ−ペンチル基
、ｎ−ヘキシル基、ｎ−へブチル基、ｎ−オクチル基、
ｎ−ノニル基、ｎ−デシル基、ｎ−ウンデシル基、ｎ−
ドデシル基等が挙げられる。 アリール基としては、例
えば、フェニル基、ｐ−メトキシフェニル基、ｐ−クロ
ロフェニル基、ｐ−フルオロフェニル基、ナフチル基等
が挙げられる。In the general formula (I) representing the double bond-containing compound that is the starting material of the present invention, R' is a linear or branched alkyl group or aryl group, and may have a substituent. As a straight chain or branched alkyl group,
For example, ethyl group, n-propyl group, n-butyl group, 5
ec-butyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-hebutyl group, n-octyl group,
n-nonyl group, n-decyl group, n-undecyl group, n-
Examples include dodecyl group. Examples of the aryl group include phenyl group, p-methoxyphenyl group, p-chlorophenyl group, p-fluorophenyl group, and naphthyl group.
Ｒ２およびＲ３は同一でも異なってもよく、水素原子、
置換もしくは非置換のアルキル基またはアリール基であ
る。 この置換もしくは非置換のアルキル基としては、
例えば、メチル基、エチル基、ｎ−プロピル基、フェニ
ルメチル基等が挙げられ、アリール基としては、例えば
、フェニル基、ナフチル基、あるいはｐ−フルオロフェ
ニル基、ｐ−クロロフェニル基、ｐ−メトキシフェニル
基等の置換基を有するアリール基が挙げられ゛る。 ま
た、Ｒ１とＲ３は相互に結合して環を形成していてもよ
（、例えば、相互に結合してシクロペンチル基、シクロ
ヘキシル基、シクロへブチル基、シクロオクチル基等の
環を形成していてもよい。R2 and R3 may be the same or different, and are hydrogen atoms,
It is a substituted or unsubstituted alkyl group or aryl group. This substituted or unsubstituted alkyl group is
Examples include methyl group, ethyl group, n-propyl group, phenylmethyl group, and examples of aryl groups include phenyl group, naphthyl group, p-fluorophenyl group, p-chlorophenyl group, and p-methoxyphenyl group. Examples include aryl groups having substituents such as groups. Furthermore, R1 and R3 may be bonded to each other to form a ring (for example, R1 and R3 may be bonded to each other to form a ring such as a cyclopentyl group, cyclohexyl group, cyclohebutyl group, or cyclooctyl group). Good too.
また、Ｒ’とＲ１は相互に結合して環を形成していても
よく、例えば、相互に結合して、ノルボニル基などの基
を形成していてもよい。Further, R' and R1 may be bonded to each other to form a ring, for example, may be bonded to each other to form a group such as a norbornyl group.
さらに、ＲＩ Ｒ！およびＲ１は、同時に結合して縮
合環を形成していてもよ（、例えば、下記式：
で表わされる縮合環を形成していてもよい。Furthermore, RI R! and R1 may be bonded together to form a condensed ring (for example, may form a condensed ring represented by the following formula:
前記−膜袋（Ｉ）で表わされる二重結合含有化合物の代
表例として、４２−メチル−２−デセン、ｃｉｓ−２−
オクテン、ｔｒａｎｓ −２−オクテン、２−メチル−
１−デセン、１−デセン等のオレフィン類；２−ノルボ
ルネン等の脂環式不飽和炭化水素類：スチレン等の芳香
族不飽和炭化水素、あるいは下記式（Ｉ−Ａ）〜（Ｉ−
■）で表わされるものが挙げられる。Representative examples of the double bond-containing compound represented by the membrane bag (I) include 42-methyl-2-decene, cis-2-
octene, trans-2-octene, 2-methyl-
Olefins such as 1-decene and 1-decene; alicyclic unsaturated hydrocarbons such as 2-norbornene; aromatic unsaturated hydrocarbons such as styrene, or the following formulas (IA) to (I-
■) can be mentioned.
物を選択すればよい。Just choose something.
本発明の方法で用いられる触媒は、酢酸ニッケルおよび
／またはニッケル錯体からなるものである。 触媒とし
て用いられるニッケル錯体の代表例としては、例えば、
下記−膜袋％式％）：
本発明の方法においては、所望の構造を有するエポキシ
基含有化合物が得られるように、前記−膜袋（Ｉ）で表
わされる二重結合金有化合で表わされるニッケル化合物
が挙げられる。The catalyst used in the method of the invention consists of nickel acetate and/or a nickel complex. Typical examples of nickel complexes used as catalysts include:
In the method of the present invention, in order to obtain an epoxy group-containing compound having a desired structure, the following - membrane bag (% formula %): Examples include nickel compounds.
本発明の方法において、酢酸ニッケルまたはニッケ−ル
錯体は、１種単独でも２種以上を組合せて用いてもよい
。In the method of the present invention, nickel acetate or nickel complexes may be used alone or in combination of two or more.
また、このニッケル錯体は、いずれの方法によって得ら
れたものでもよ（、特に限定されない。 また、市販品
を用いてもよい。Further, this nickel complex may be obtained by any method (but is not particularly limited). Also, a commercially available product may be used.
このニッケル錯体は、例えば、所望のニッケル錯体に対
応するジケトン化合物と、Ｎ１５Ｏｎ、Ｎ１Ｃｌ２ｘま
たはＮｉ （ＯＡｃ） ｚとを用いて、脱塩法で製造す
ることができる。 このようにして得られる生成物は、
反応溶媒等を除去した後、乾燥してそのまま使用しても
よい、 さらに有機溶媒で抽出した精製物として使用し
てもよいし、減圧下に、昇華精製して使用してもよく、
またこれらの精製法を組合わせて精製し使用に供しても
よい。This nickel complex can be produced, for example, by a desalting method using a diketone compound corresponding to the desired nickel complex and N15On, N1Cl2x or Ni(OAc)z. The product thus obtained is
After removing the reaction solvent, etc., it may be dried and used as it is, or it may be used as a purified product extracted with an organic solvent, or it may be purified by sublimation under reduced pressure.
Further, these purification methods may be used in combination for purification and use.
本発明の方法において、酢酸ニッケルおよび／またはニ
ッケル錯体からなる触媒の使用量は、通常、出発原料で
ある前記一般式（Ｉ）で表される二重結合含有化合物１
モル、に対してｏ、 ｏｏｓ〜１０モル％の割合であり
、特に、エポキシ基含有化合物の収率が高い点で、０．
００９６〜４モル％の割合が一般的である。In the method of the present invention, the amount of the catalyst consisting of nickel acetate and/or nickel complex used is usually determined based on the amount of the double bond-containing compound represented by the general formula (I), which is the starting material.
The ratio is 0.00 to 10% by mole based on the mole, and in particular, the yield of the epoxy group-containing compound is high.
A proportion of 0.0096 to 4 mol% is common.
本発明の方法においては、前記の触媒とともに、前記一
般式（ｎ）で表わされるアルデヒド化合物が用いられる
。 一般式（ｎ）において、Ｒ７は直鎖または分岐状の
アルキル基、もしくはシクロアルキル基またはアリール
基である。 直鎖または分岐状のアルキル基の代表例と
しては、メチル基、エチル基、ｎ−プロピル基、１ｓｏ
−プロピル基、ｎ−ブチル基、５ｅｃ−ブチル基、ｔｅ
ｒｔ−ブチル基、１ｓｏ−ブチル基、ｎ−ペンチル基、
ｎ−ヘキシル基、ｎ−へブチル基、ｎ−オクチル基、ｎ
−ノニル基、ｎ−デシル基、ｎ−ウンデシル基、ｎ−ド
デシル基等が挙げられ、シクロアルキル基の代表例とし
ては、シクロヘキシル基、シクロペンチル基、シクロへ
ブチル基、シクロオクチル基等が挙げられる。 アリー
ル基の代表例としては、フェニル基、ｐ−メトキシフェ
ニル基等が挙げられる。 また、これらの直鎖または分
岐状のアルキル基、もしくはシクロアルキル基またはア
リール基は、置換基を有していてもよく、例えば、塩素
、フッ素等のハロゲン原子、メトキシ基などの置換基を
有していてもよい。In the method of the present invention, the aldehyde compound represented by the general formula (n) is used together with the catalyst. In general formula (n), R7 is a linear or branched alkyl group, a cycloalkyl group, or an aryl group. Typical examples of linear or branched alkyl groups include methyl group, ethyl group, n-propyl group, 1so
-propyl group, n-butyl group, 5ec-butyl group, te
rt-butyl group, 1so-butyl group, n-pentyl group,
n-hexyl group, n-hebutyl group, n-octyl group, n
-Nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, etc., and representative examples of cycloalkyl group include cyclohexyl group, cyclopentyl group, cyclohebutyl group, cyclooctyl group, etc. . Representative examples of the aryl group include phenyl group, p-methoxyphenyl group, and the like. In addition, these linear or branched alkyl groups, cycloalkyl groups, or aryl groups may have a substituent, for example, a halogen atom such as chlorine or fluorine, or a substituent such as a methoxy group. You may do so.
この一般式（ｎ）で表わされるアルデヒド化合物の代表
例として、アセトアルデヒド、プロピオンアルデヒド、
ブチルアルデヒド、バレルアルデヒド、ヘキシルアルデ
ヒド、ヘプチルアルデヒド、オクチルアルデヒド、ノニ
ルアルデヒド、デシルアルデヒド、ウンデシルアルデヒ
ド、ドデシルアルデヒド、イソブチルアルデヒド、２−
メチルバレルアルデヒド、２−エチルブチルアルデヒド
、２−メチルバレルアルデヒド、イソバレルアルデヒド
、ビバルアルデヒド、２−フェニルプロピオンアルデヒ
ド、３−フェニルプロパナール、シクロヘキサンカルバ
ルデヒド等が挙げられる。Representative examples of the aldehyde compound represented by the general formula (n) include acetaldehyde, propionaldehyde,
Butyraldehyde, valeraldehyde, hexylaldehyde, heptylaldehyde, octylaldehyde, nonylaldehyde, decylaldehyde, undecylaldehyde, dodecylaldehyde, isobutyraldehyde, 2-
Examples include methylvaleraldehyde, 2-ethylbutyraldehyde, 2-methylvaleraldehyde, isovaleraldehyde, bivalaldehyde, 2-phenylpropionaldehyde, 3-phenylpropanal, and cyclohexanecarbaldehyde.
本発明において、前記一般式（ＩＩ）で表わされるアル
デヒド化合物は、１種単独でも２種以上を組合せても用
いられる。In the present invention, the aldehyde compounds represented by the general formula (II) may be used alone or in combination of two or more.
この一般式（ｎ）で表わされるアルデヒド化合物の使用
量は、出発物質である前記一般式（Ｉ）で表される二重
結合含有化合物１モルに対して、通常、１モル以上、好
ましくは１〜１０モルが一般的である。 また、この反
応は、溶媒を用いて行うこともでき、この場合には、通
常は、上記の触媒１モルに対して、１〜１０モルの上記
アルデヒド化合物を、溶媒で希釈して使用することもで
きる。 用いられる溶媒としては、反応に対して不活性
な溶媒を使用することができ、このような溶媒の具体的
な例としては、ベンゼン、トルエン、ｏ −ｍ−または
ｐ−キシレン、メシチレン等の芳香族炭化水素系溶媒；
クロロホルム、ジクロロメタン、ジクロロエタンのよう
なハロゲン化炭化水素系溶媒：酢酸エチル、酢酸プロピ
ル、酢酸ブチル等のエステル系溶媒；アセトニトリル、
アセトン、ジエチルケトン、ＴＨＦなどを挙げることが
できる。 これらの溶媒は単独であるいは組み合わせて
使用することができる。 特に、ジクロロエタンが、エ
ポキシ基含有化合物の収率が高い点で、好ましい。The amount of the aldehyde compound represented by the general formula (n) to be used is usually 1 mol or more, preferably 1 mol or more, per 1 mol of the double bond-containing compound represented by the general formula (I) as a starting material. ~10 moles are typical. Moreover, this reaction can also be carried out using a solvent, and in this case, usually 1 to 10 moles of the above aldehyde compound are diluted with a solvent and used per 1 mole of the above catalyst. You can also do it. As the solvent used, a solvent inert to the reaction can be used, and specific examples of such solvents include aromatic solvents such as benzene, toluene, o-m- or p-xylene, and mesitylene. Group hydrocarbon solvent;
Halogenated hydrocarbon solvents such as chloroform, dichloromethane, and dichloroethane; Ester solvents such as ethyl acetate, propyl acetate, butyl acetate; acetonitrile,
Examples include acetone, diethyl ketone, and THF. These solvents can be used alone or in combination. In particular, dichloroethane is preferable since it provides a high yield of the epoxy group-containing compound.
本発明の方法で用いられる酸素含有ガスは、酸素ガス（
純酸素）でもよいし、酸素含有窒素ガス（例えば空気）
、酸素含有アルゴンガス等の酸素含有不活性ガスでもよ
い。The oxygen-containing gas used in the method of the present invention is oxygen gas (
pure oxygen) or oxygen-containing nitrogen gas (e.g. air)
, oxygen-containing inert gas such as oxygen-containing argon gas.
酸素含有ガス中の酸素の分圧は、好ましくは０ 、 １
ａｔｍ〜ｌ Ｏｋｇ／ｃｍ”程度、より好ましくは０
．２〜１．０ａｔｍ程度である。 酸素の分圧がこの範
囲内にあると、反応速度が速く、反応収率もよい。The partial pressure of oxygen in the oxygen-containing gas is preferably 0, 1
atm~l Okg/cm”, more preferably 0
．． It is about 2 to 1.0 atm. When the partial pressure of oxygen is within this range, the reaction rate is fast and the reaction yield is good.
また、本発明の方法においては、反応を合成ゼオライト
の存在下に行うと、より高い収率で前記一般式（Ｉ［Ｉ
）で表されるエポキシ基含有化合物を得ることができる
ため、好ましい。Furthermore, in the method of the present invention, when the reaction is carried out in the presence of a synthetic zeolite, a higher yield can be achieved with the general formula (I[I
) is preferable since it is possible to obtain an epoxy group-containing compound represented by:
反応温度は、通常、０〜１００℃程度であり、さらに２
０〜５０℃が、エポキシ基含有化合物の収率が高くなる
点で、好ましい。The reaction temperature is usually about 0 to 100°C, and
A temperature of 0 to 50°C is preferable since the yield of the epoxy group-containing compound is high.
反応圧力は、特に制限されず、常圧で十分である。The reaction pressure is not particularly limited, and normal pressure is sufficient.
本発明の方法における反応は、液相中で連続的に行って
もよいし、回分的に行ってもよい。The reaction in the method of the present invention may be carried out continuously in a liquid phase or may be carried out batchwise.
以上の反応によって得られる反応混合物は、通常、副生
物、未反応の出発原料、触媒等を含有するため、本発明
の目的物であるエポキシ基含有化合物は、この反応混合
物中から分離、精製して得ることができる。 用いられ
る分離方法は、特に制限されず、例えば、蒸留、吸着に
よる方法、抽出、再結晶等公知の分離方法によればよい
。Since the reaction mixture obtained by the above reaction usually contains by-products, unreacted starting materials, catalysts, etc., the epoxy group-containing compound, which is the object of the present invention, must be separated and purified from this reaction mixture. You can get it. The separation method used is not particularly limited, and may be any known separation method such as distillation, adsorption, extraction, recrystallization, etc.
本発明の方法で得られる前記一般式（ＩＩ［）で表わさ
れるエポキシ基含有化合物の代表的なものとしては、下
記式で表されるものが挙げられる。Representative examples of the epoxy group-containing compound represented by the general formula (II[) obtained by the method of the present invention include those represented by the following formula.
本発明の方法によって得られるエポキシ基含有化合物は
、例えば、合成中間体、ポリマー原料等の用途に有用で
ある。The epoxy group-containing compound obtained by the method of the present invention is useful, for example, as a synthetic intermediate, a polymer raw material, and the like.
〈実施例〉
以下、実施例および比較例により本発明を具体的に説明
するが、本発明は、これらの実施例に限定されるもので
はない。<Examples> The present invention will be specifically described below with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
（実施例１〜４）
各側において、反応容器に、２−メチル−２−デセン３
．Ｏｍｍｏρ、イソブチルアルデヒド６、 Ｏｍｍｏ
Ａおよびジクロロエタン２ｍｎ、並びに触媒として表１
に示すニッケル化合物０．０６ ■ｌｌ１ｏβを仕込ん
だ。 次いで、反応容器内に、１ ａｔｍの酸素ガスを
充填し、室温で１３時間反応させた。(Examples 1-4) On each side, 2-methyl-2-decene 3
．． Ommoρ, isobutyraldehyde 6, Ommo
A and 2 mn of dichloroethane, and Table 1 as catalyst
A nickel compound of 0.06 1ll1oβ shown in the figure was charged. Next, the reaction vessel was filled with 1 atm of oxygen gas and reacted at room temperature for 13 hours.
反応終了後、得られた反応混合物をガスクロマトグラフ
ィーにかけて分析し、出発原料である２−メチル−２−
デセンの転化率、および生成物であるエポキシド（２，
２−ジメチル−３−へブチルオキシラン）の収率を求め
た。 結果を表１に示す。After the reaction was completed, the resulting reaction mixture was analyzed by gas chromatography, and the starting material 2-methyl-2-
The conversion rate of decene and the product epoxide (2,
The yield of 2-dimethyl-3-hebutyloxirane was determined. The results are shown in Table 1.
〈発明の効果〉
本発明の方法によれば、特定の構造のニッケル化合物を
触媒として用いる新規な反応により、エポキシ基含有化
合物を得ることができる。 この反応は、従来のこの種
のエポキシ基含有化合物の製造に適用されてきた反応に
比して、反応温度および反応圧力等において穏やかな反
応条件で行なうことができ、また、使用するニッケル化
合物も少量でよく、工業的に有利である。<Effects of the Invention> According to the method of the present invention, an epoxy group-containing compound can be obtained by a novel reaction using a nickel compound with a specific structure as a catalyst. This reaction can be carried out under mild reaction conditions such as reaction temperature and reaction pressure, compared to the reaction conventionally applied to the production of this type of epoxy group-containing compound, and also the nickel compound used can be Only a small amount is required and it is industrially advantageous.
Claims (2)
ール基であり、置換基を有していてもよく、Ｒ＾２およ
びＲ＾３は同一でも異なってもよく、水素原子、置換あ
るいは非置換のアルキル基またはアリール基であり、相
互に結合して環を形成していてもよく、またＲ＾１とＲ
＾２は、相互に結合して環を形成していてもよく、さら
にＲ＾１、Ｒ＾２およびＲ＾３は、同時に結合して縮合
環を形成していてもよい］ で表される二重結合含有化合物を、酢酸ニッケルおよび
／またはニッケル錯体からなる触媒と、下記一般式（I
I）： Ｒ＾７ＣＨＯ（II） ［ここで、Ｒ＾７は直鎖または分岐状のアルキル基、も
しくはアリール基であり、置換基を有していてもよい］ で表わされるアルデヒド化合物との存在下に、酸素含有
ガスと反応させる工程を含む、 一般式（III）： ▲数式、化学式、表等があります▼（III） ［Ｒ＾１、Ｒ＾２およびＲ＾３は前記一般式（ I ）に
おいて定義したとおりである］ で表されるエポキシ基含有化合物の製造方 法。(1) General formula (I): ▲Mathematical formulas, chemical formulas, tables, etc.▼(I) [In the formula, R^1 is a linear or branched alkyl group or aryl group, and has a substituent. R^2 and R^3 may be the same or different, and are a hydrogen atom, a substituted or unsubstituted alkyl group, or an aryl group, and may be bonded to each other to form a ring, or R^1 and R
^2 may be bonded to each other to form a ring, and R^1, R^2, and R^3 may be bonded to each other to form a condensed ring] A double bond-containing compound is combined with a catalyst consisting of nickel acetate and/or a nickel complex and the following general formula (I
I): Presence of an aldehyde compound represented by R^7CHO(II) [Here, R^7 is a linear or branched alkyl group or an aryl group, and may have a substituent] General formula (III), which includes the step of reacting with oxygen-containing gas: ▲Mathematical formulas, chemical formulas, tables, etc.▼(III) [R^1, R^2 and R^3 are the general formula (I )] A method for producing an epoxy group-containing compound.
種である請求項１に記載のエポキシ基含有化合物の製造
方法。(2) The nickel complex has the following formula: ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IVA) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IVB) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (IVC) At least one selected from the nickel compounds represented by
The method for producing an epoxy group-containing compound according to claim 1, which is a seed.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2212459A JP2911192B2 (en) | 1990-08-09 | 1990-08-09 | Method for producing epoxy group-containing compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2212459A JP2911192B2 (en) | 1990-08-09 | 1990-08-09 | Method for producing epoxy group-containing compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0495079A true JPH0495079A (en) | 1992-03-27 |
| JP2911192B2 JP2911192B2 (en) | 1999-06-23 |
Family
ID=16622984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2212459A Expired - Fee Related JP2911192B2 (en) | 1990-08-09 | 1990-08-09 | Method for producing epoxy group-containing compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2911192B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5367087A (en) * | 1991-10-30 | 1994-11-22 | Sumitomo Chemical Company, Limited | Process for producing epoxide |
-
1990
- 1990-08-09 JP JP2212459A patent/JP2911192B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5367087A (en) * | 1991-10-30 | 1994-11-22 | Sumitomo Chemical Company, Limited | Process for producing epoxide |
| US5466838A (en) * | 1991-10-30 | 1995-11-14 | Sumitomo Chemical Company, Limited | Process for producing epoxide |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2911192B2 (en) | 1999-06-23 |
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