JP6633537B2 - デカリン誘導体の製造方法 - Google Patents
デカリン誘導体の製造方法 Download PDFInfo
- Publication number
- JP6633537B2 JP6633537B2 JP2016555394A JP2016555394A JP6633537B2 JP 6633537 B2 JP6633537 B2 JP 6633537B2 JP 2016555394 A JP2016555394 A JP 2016555394A JP 2016555394 A JP2016555394 A JP 2016555394A JP 6633537 B2 JP6633537 B2 JP 6633537B2
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- JP
- Japan
- Prior art keywords
- decalin
- bis
- allyloxy
- formula
- group
- 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.)
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- 238000004519 manufacturing process Methods 0.000 title claims description 25
- 125000004855 decalinyl group Chemical class C1(CCCC2CCCCC12)* 0.000 title description 10
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical class C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 134
- 125000005336 allyloxy group Chemical group 0.000 claims description 73
- 238000006243 chemical reaction Methods 0.000 claims description 53
- -1 allyl halide Chemical class 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 41
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 claims description 41
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 39
- 239000000126 substance Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- PEENFGPEMPLNSH-UHFFFAOYSA-N 2-[[7-(oxiran-2-ylmethoxy)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-yl]oxymethyl]oxirane Chemical compound C(C1CO1)OC1CC2CC(CCC2CC1)OCC1CO1 PEENFGPEMPLNSH-UHFFFAOYSA-N 0.000 claims description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- QUHXOVKYGFZEGE-UHFFFAOYSA-N 2-(1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yloxymethyl)oxirane Chemical class C(C1CO1)OC1CCCC2CCCCC12 QUHXOVKYGFZEGE-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- NDZOISQLWLWLEW-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-ol Chemical compound C1CCCC2C(O)CCCC21 NDZOISQLWLWLEW-UHFFFAOYSA-N 0.000 claims description 13
- 150000002825 nitriles Chemical class 0.000 claims description 12
- 239000003444 phase transfer catalyst Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical class C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 claims description 4
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical class CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 3
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical class CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 claims description 3
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical class CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 claims description 3
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical class CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 claims description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000003822 epoxy resin Substances 0.000 description 20
- 229920000647 polyepoxide Polymers 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- AWYGUQISGIHJPB-UHFFFAOYSA-N 2-[[8a-(oxiran-2-ylmethoxy)-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-yl]oxymethyl]oxirane Chemical class C(C1CO1)OC12CCCCC2(CCCC1)OCC1CO1 AWYGUQISGIHJPB-UHFFFAOYSA-N 0.000 description 13
- 239000004593 Epoxy Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002994 raw material Substances 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000004821 distillation Methods 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 125000003700 epoxy group Chemical group 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000005210 alkyl ammonium group Chemical group 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000003287 optical effect Effects 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- ALMLVUGGLRJZPE-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-2,7-diol Chemical compound C1CC(O)CC2CC(O)CCC21 ALMLVUGGLRJZPE-UHFFFAOYSA-N 0.000 description 5
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 5
- NEOQYOIJTNVELW-UHFFFAOYSA-N C(C1CO1)OC1CC2CCC(CC2CC1)OCC1CO1 Chemical compound C(C1CO1)OC1CC2CCC(CC2CC1)OCC1CO1 NEOQYOIJTNVELW-UHFFFAOYSA-N 0.000 description 4
- KCMQPNUQQGKNHZ-UHFFFAOYSA-N C(C1CO1)OC1CC2CCCCC2CC1OCC1CO1 Chemical compound C(C1CO1)OC1CC2CCCCC2CC1OCC1CO1 KCMQPNUQQGKNHZ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- PJTGTSGIIFUDBH-UHFFFAOYSA-N C(C1CO1)OC1CC2CCCCC2CC1 Chemical compound C(C1CO1)OC1CC2CCCCC2CC1 PJTGTSGIIFUDBH-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000004065 semiconductor Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- OGRULRAOMCDCBO-UHFFFAOYSA-N 2-[[1-(oxiran-2-ylmethoxy)naphthalen-2-yl]oxymethyl]oxirane Chemical compound C1OC1COC1=CC=C2C=CC=CC2=C1OCC1CO1 OGRULRAOMCDCBO-UHFFFAOYSA-N 0.000 description 2
- NWPNXBQSRGKSJB-UHFFFAOYSA-N 2-methylbenzonitrile Chemical compound CC1=CC=CC=C1C#N NWPNXBQSRGKSJB-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003566 sealing material Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UPMAOXLCTXPPAG-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-2-ol Chemical compound C1CCCC2CC(O)CCC21 UPMAOXLCTXPPAG-UHFFFAOYSA-N 0.000 description 1
- WTIPFYCAMXYLQJ-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-2,3-diol Chemical compound C1CCCC2CC(O)C(O)CC21 WTIPFYCAMXYLQJ-UHFFFAOYSA-N 0.000 description 1
- OIXGILBUABDWRY-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalene-2,6-diol Chemical compound C1C(O)CCC2CC(O)CCC21 OIXGILBUABDWRY-UHFFFAOYSA-N 0.000 description 1
- WHVGOCCZWVVJTC-UHFFFAOYSA-N 1,2,3,4,5,6,7,8-octahydronaphthalene-4a,8a-diol Chemical compound C1CCCC2(O)CCCCC21O WHVGOCCZWVVJTC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- GCFGUKCSBVHPGG-UHFFFAOYSA-N 2-[[5-(oxiran-2-ylmethoxy)-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl]oxymethyl]oxirane Chemical compound C(C1CO1)OC1CCCC2C(CCCC12)OCC1CO1 GCFGUKCSBVHPGG-UHFFFAOYSA-N 0.000 description 1
- AFMPMSCZPVNPEM-UHFFFAOYSA-N 2-bromobenzonitrile Chemical compound BrC1=CC=CC=C1C#N AFMPMSCZPVNPEM-UHFFFAOYSA-N 0.000 description 1
- NHWQMJMIYICNBP-UHFFFAOYSA-N 2-chlorobenzonitrile Chemical compound ClC1=CC=CC=C1C#N NHWQMJMIYICNBP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- STXAVEHFKAXGOX-UHFFFAOYSA-N 3-bromobenzonitrile Chemical compound BrC1=CC=CC(C#N)=C1 STXAVEHFKAXGOX-UHFFFAOYSA-N 0.000 description 1
- WBUOVKBZJOIOAE-UHFFFAOYSA-N 3-chlorobenzonitrile Chemical compound ClC1=CC=CC(C#N)=C1 WBUOVKBZJOIOAE-UHFFFAOYSA-N 0.000 description 1
- BOHCMQZJWOGWTA-UHFFFAOYSA-N 3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1 BOHCMQZJWOGWTA-UHFFFAOYSA-N 0.000 description 1
- HQSCPPCMBMFJJN-UHFFFAOYSA-N 4-bromobenzonitrile Chemical compound BrC1=CC=C(C#N)C=C1 HQSCPPCMBMFJJN-UHFFFAOYSA-N 0.000 description 1
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 1
- VCZNNAKNUVJVGX-UHFFFAOYSA-N 4-methylbenzonitrile Chemical compound CC1=CC=C(C#N)C=C1 VCZNNAKNUVJVGX-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- YGOQAETYWJGRJS-UHFFFAOYSA-N C(C1CO1)OC1CCCC2CC(CCC12)OCC1CO1 Chemical compound C(C1CO1)OC1CCCC2CC(CCC12)OCC1CO1 YGOQAETYWJGRJS-UHFFFAOYSA-N 0.000 description 1
- BDJQSLUWVKEBTQ-UHFFFAOYSA-N C1CC2CCC(CC2C(C1)OCC3CO3)OCC4CO4 Chemical compound C1CC2CCC(CC2C(C1)OCC3CO3)OCC4CO4 BDJQSLUWVKEBTQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000001334 alicyclic compounds Chemical class 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004799 bromophenyl group Chemical group 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- AILKHAQXUAOOFU-UHFFFAOYSA-N hexanenitrile Chemical compound CCCCCC#N AILKHAQXUAOOFU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000001165 hydrophobic group Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 125000000466 oxiranyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- ZNEOHLHCKGUAEB-UHFFFAOYSA-N trimethylphenylammonium Chemical class C[N+](C)(C)C1=CC=CC=C1 ZNEOHLHCKGUAEB-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/18—Ethers having an ether-oxygen atom bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C43/188—Unsaturated ethers
-
- 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
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/28—Ethers with hydroxy compounds containing oxirane rings
- C07D303/30—Ethers of oxirane-containing polyhydroxy compounds in which all hydroxyl radicals are etherified with oxirane-containing hydroxy compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Epoxy Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
但し、デカリン誘導体から2,7−ビス(グリシジルオキシ)デカリンは除かれる。
で表される(アリルオキシ)デカリン誘導体と、過酸化水素と、
式 R1−C≡N
(式中、R1は炭素数1〜6のアルキル基又は置換基を有することのあるフェニル基である)
で表されるニトリル類を、塩基性物質を用いて反応液のpHを9〜11に維持しながら反応させ、式(1-2)
で表される(グリシジルオキシ)デカリン誘導体を製造する。
で表されるヒドロキシデカリンに、相間移動触媒及び塩基性物質の存在下、アリルハライド(又はハロゲン化アリル)を反応させることにより調製してもよい。
式 R1−C≡N
(式中、R1は前記と同じ)
で表されるニトリル類を、塩基性物質を用いて反応液のpHを9〜11に維持しながら反応させ、前記式(1-2)で表される(グリシジルオキシ)デカリン誘導体を製造する。
2,7−ビス(グリシジルオキシ)デカリン
3Lのフラスコに、メタノール389.4g、2,7−ビス(アリルオキシ)デカリン401.2g(純度98.0%、1.57モル)、アセトニトリル387.1g(9.42モル、6当量)を仕込み、0〜15℃に冷却し、35%過酸化水素水610.1g(6.28モル、4当量)を10〜15℃の範囲で5時間以上かけて滴下すると共に8%水酸化ナトリウム水を適宜滴下し、反応液のpHを9.5〜10.5に調整した。その後、20〜30℃に温調し4時間反応させた。
2,7−ビス(グリシジルオキシ)デカリン
3Lのフラスコに、メタノール389.4g、2,7−ビス(アリルオキシ)デカリン401.2g(純度98.0%、1.57モル)、アセトニトリル387.1g(9.42モル、6当量)及び炭酸カリウム43.4g(0.31モル、0.2当量)を仕込み、0〜15℃に冷却し、35%過酸化水素水610.1g(6.28モル、4当量)を10〜15℃の範囲で5時間以上かけ滴下すると共に炭酸カリウムを適宜添加し、反応液のpHを9.5〜10.5に調整した。その後、20〜30℃に温調し4時間反応させた。
実施例1において、反応液のpHをほぼ9に維持する以外は同様に反応及び処理して、2,7−ビス(ジグリシジルオキシ)デカリンを得た(収率:77.5%)。
実施例1において、アセトニトリルに代えてベンゾニトリルを使用する以外は実質的に同様に反応及び処理して、2,7−ビス(ジグリシジルオキシ)デカリンを得た(収率:81.3%)。
2,7−ビス(アリルオキシ)デカリン
3Lのフラスコに、50%水酸化ナトリウム2720.0g(34.0モル、20当量)を仕込み、15〜25℃に温調した後、ベンジル−n−トリブチルアンモニウムクロリド53.0g(0.17モル、0.1当量)、アリルクロライド520.2g(6.8モル、4当量)、2,7−ジヒドロキシデカリン289.5g(1.7モル)をそれぞれ加えた後、15〜25℃の範囲で7時間反応させた。反応後、5L分液ロートへ移送し、トルエン850gを加え室温で30分撹拌、30分静置した後下層の水層を分液し有機層を分取した。その後、有機層をイオン交換水850gにて洗浄・分液を2回行い、減圧濃縮、薄膜蒸留(蒸留条件:熱媒温度150℃、真空度4hPa)によって402.2gの2,7−ビス(アリルオキシ)デカリンを無色透明液で得た。(純度98.0%、全Cl分900ppm以下、収率92.6%)
1H NMR(400MHz,CDCl3)δ: 1.17−2.10(m,14H), 3.20−3.29(m,1H), 3.40−3.49(m,1H), 3.93−4.04(m,4H), 5.11−5.17(m,2H),5.22−5.30(m,2H), 5.85−5.98(m,2H)ppm。
製造例1において、アリルクロライドを2,7−ジヒドロキシデカリンに対して10倍モル使用する以外は同様に反応・処理して、2,7−ビス(アリルオキシ)デカリンを得た(収率:91.0%)。
1−アリルオキシデカリン
1−グリシジルオキシデカリン
2−アリルオキシデカリン
2−グリシジルオキシデカリン
1H NMR(400MHz,CDCl3)δ: 1.19−1.78(m,16H), 2.61−2.63(m,1H), 2.79−2.81(m,1H), 3.12−3.16(m,1H), 3.30−3.32(m,1H), 3.45−3.49(m,1H), 3.69−3.73(m,1H)ppm。
2,3−ビス(アリルオキシ)デカリン
2,3−ビス(グリシジルオキシ)デカリン
2,6−ビス(アリルオキシ)デカリン
2,6−ビス(グリシジルオキシ)デカリン
Claims (6)
- 式(1-1)で表される化合物として2,7−ビス(アリルオキシ)デカリンを用い、2,7−ビス(グリシジルオキシ)デカリンを製造する請求項1記載の方法。
- ニトリル類が、アセトニトリル又はベンゾニトリルである請求項1又は2記載の方法。
- 反応液のpHを9.5〜10.5に調整しながら反応させる請求項1〜3のいずれかに記載の方法。
- 相間移動触媒が、トリオクチルメチルアンモニウム塩、トリラウリルメチルアンモニウム塩、セチルトリメチルアンモニウム塩、ベンジルトリメチルアンモニウム塩、ベンジルトリエチルアンモニウム塩、ベンジルトリ−n−ブチルアンモニウム塩から選択された少なくとも一種である請求項5記載の製造方法。
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US4433179A (en) * | 1980-08-25 | 1984-02-21 | Ciba-Geigy Corporation | Process for the preparation of di- and poly-allyl ethers |
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