JPWO2011027618A1 - トリシクロデカンモノメタノールモノカルボン酸及びその誘導体 - Google Patents
トリシクロデカンモノメタノールモノカルボン酸及びその誘導体 Download PDFInfo
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- JPWO2011027618A1 JPWO2011027618A1 JP2011529847A JP2011529847A JPWO2011027618A1 JP WO2011027618 A1 JPWO2011027618 A1 JP WO2011027618A1 JP 2011529847 A JP2011529847 A JP 2011529847A JP 2011529847 A JP2011529847 A JP 2011529847A JP WO2011027618 A1 JPWO2011027618 A1 JP WO2011027618A1
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- Prior art keywords
- compound
- acid
- reaction
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- tricyclodecane
- Prior art date
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- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 title claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 2
- 229920000728 polyester Polymers 0.000 abstract description 20
- 239000002994 raw material Substances 0.000 abstract description 17
- 125000002723 alicyclic group Chemical group 0.000 abstract description 10
- 238000006243 chemical reaction Methods 0.000 description 57
- -1 aromatic dicarboxylic acids Chemical class 0.000 description 55
- 150000003304 ruthenium compounds Chemical class 0.000 description 30
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 18
- 239000003054 catalyst Substances 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 150000001869 cobalt compounds Chemical class 0.000 description 17
- 238000007037 hydroformylation reaction Methods 0.000 description 15
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- 238000000034 method Methods 0.000 description 13
- 230000001737 promoting effect Effects 0.000 description 13
- 239000002253 acid Chemical class 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- 150000001768 cations Chemical class 0.000 description 10
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- 239000003446 ligand Substances 0.000 description 10
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- 239000007789 gas Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
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- 229910052736 halogen Inorganic materials 0.000 description 8
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- 125000000217 alkyl group Chemical group 0.000 description 7
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- 238000004458 analytical method Methods 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
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- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
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- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 229940011182 cobalt acetate Drugs 0.000 description 4
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 4
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 229910001410 inorganic ion Inorganic materials 0.000 description 4
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 4
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- 230000003287 optical effect Effects 0.000 description 4
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- 150000002896 organic halogen compounds Chemical class 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- BOOXKGZZTBKJFE-UHFFFAOYSA-M 1-butyl-1-methylpyrrolidin-1-ium;chloride Chemical compound [Cl-].CCCC[N+]1(C)CCCC1 BOOXKGZZTBKJFE-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229910002091 carbon monoxide Inorganic materials 0.000 description 3
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 3
- 150000003841 chloride salts Chemical class 0.000 description 3
- 230000009477 glass transition Effects 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000002608 ionic liquid Substances 0.000 description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005979 thermal decomposition reaction Methods 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 2
- PXELHGDYRQLRQO-UHFFFAOYSA-N 1-butyl-1-methylpyrrolidin-1-ium Chemical compound CCCC[N+]1(C)CCCC1 PXELHGDYRQLRQO-UHFFFAOYSA-N 0.000 description 2
- XUAXVBUVQVRIIQ-UHFFFAOYSA-N 1-butyl-2,3-dimethylimidazol-3-ium Chemical compound CCCCN1C=C[N+](C)=C1C XUAXVBUVQVRIIQ-UHFFFAOYSA-N 0.000 description 2
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 2
- LDVVBLGHGCHZBJ-UHFFFAOYSA-N 1-decyl-3-methylimidazolium Chemical compound CCCCCCCCCCN1C=C[N+](C)=C1 LDVVBLGHGCHZBJ-UHFFFAOYSA-N 0.000 description 2
- ILQHIGIKULUQFQ-UHFFFAOYSA-N 1-dodecyl-3-methylimidazolium Chemical compound CCCCCCCCCCCCN1C=C[N+](C)=C1 ILQHIGIKULUQFQ-UHFFFAOYSA-N 0.000 description 2
- IRGDPGYNHSIIJJ-UHFFFAOYSA-N 1-ethyl-2,3-dimethylimidazol-3-ium Chemical compound CCN1C=C[N+](C)=C1C IRGDPGYNHSIIJJ-UHFFFAOYSA-N 0.000 description 2
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 2
- FCZZZYZIQDHCIW-UHFFFAOYSA-N 1-heptyl-3-methylimidazol-3-ium Chemical compound CCCCCCC[N+]=1C=CN(C)C=1 FCZZZYZIQDHCIW-UHFFFAOYSA-N 0.000 description 2
- DCLKMMFVIGOXQN-UHFFFAOYSA-N 1-hexadecyl-3-methylimidazol-3-ium Chemical compound CCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 DCLKMMFVIGOXQN-UHFFFAOYSA-N 0.000 description 2
- RVEJOWGVUQQIIZ-UHFFFAOYSA-N 1-hexyl-3-methylimidazolium Chemical compound CCCCCCN1C=C[N+](C)=C1 RVEJOWGVUQQIIZ-UHFFFAOYSA-N 0.000 description 2
- AMKUSFIBHAUBIJ-UHFFFAOYSA-N 1-hexylpyridin-1-ium Chemical compound CCCCCC[N+]1=CC=CC=C1 AMKUSFIBHAUBIJ-UHFFFAOYSA-N 0.000 description 2
- WVDDUSFOSWWJJH-UHFFFAOYSA-N 1-methyl-3-propylimidazol-1-ium Chemical compound CCCN1C=C[N+](C)=C1 WVDDUSFOSWWJJH-UHFFFAOYSA-N 0.000 description 2
- BMKLRPQTYXVGNK-UHFFFAOYSA-N 1-methyl-3-tetradecylimidazol-1-ium Chemical compound CCCCCCCCCCCCCCN1C=C[N+](C)=C1 BMKLRPQTYXVGNK-UHFFFAOYSA-N 0.000 description 2
- WXMVWUBWIHZLMQ-UHFFFAOYSA-N 3-methyl-1-octylimidazolium Chemical compound CCCCCCCCN1C=C[N+](C)=C1 WXMVWUBWIHZLMQ-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- FDYYARQVPPKEAK-UHFFFAOYSA-N 4-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylic acid Chemical compound OC(=O)C1CC2CC1C1C2CC(CO)C1 FDYYARQVPPKEAK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- 239000007848 Bronsted acid Substances 0.000 description 2
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- RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 description 2
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- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 2
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-O Pyrrolidinium ion Chemical compound C1CC[NH2+]C1 RWRDLPDLKQPQOW-UHFFFAOYSA-O 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- QSRFYFHZPSGRQX-UHFFFAOYSA-N benzyl(tributyl)azanium Chemical compound CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 QSRFYFHZPSGRQX-UHFFFAOYSA-N 0.000 description 2
- VBQDSLGFSUGBBE-UHFFFAOYSA-N benzyl(triethyl)azanium Chemical compound CC[N+](CC)(CC)CC1=CC=CC=C1 VBQDSLGFSUGBBE-UHFFFAOYSA-N 0.000 description 2
- YOUGRGFIHBUKRS-UHFFFAOYSA-N benzyl(trimethyl)azanium Chemical compound C[N+](C)(C)CC1=CC=CC=C1 YOUGRGFIHBUKRS-UHFFFAOYSA-N 0.000 description 2
- BNQRPLGZFADFGA-UHFFFAOYSA-N benzyl(triphenyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 BNQRPLGZFADFGA-UHFFFAOYSA-N 0.000 description 2
- 229940006460 bromide ion Drugs 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- NMJJFJNHVMGPGM-UHFFFAOYSA-N butyl formate Chemical compound CCCCOC=O NMJJFJNHVMGPGM-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- TVFDJXOCXUVLDH-UHFFFAOYSA-N caesium atom Chemical compound [Cs] TVFDJXOCXUVLDH-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 229910000152 cobalt phosphate Inorganic materials 0.000 description 2
- GAYAMOAYBXKUII-UHFFFAOYSA-L cobalt(2+);dibenzoate Chemical compound [Co+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 GAYAMOAYBXKUII-UHFFFAOYSA-L 0.000 description 2
- ZBDSFTZNNQNSQM-UHFFFAOYSA-H cobalt(2+);diphosphate Chemical compound [Co+2].[Co+2].[Co+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O ZBDSFTZNNQNSQM-UHFFFAOYSA-H 0.000 description 2
- TZWGXFOSKIHUPW-UHFFFAOYSA-L cobalt(2+);propanoate Chemical compound [Co+2].CCC([O-])=O.CCC([O-])=O TZWGXFOSKIHUPW-UHFFFAOYSA-L 0.000 description 2
- SCNCIXKLOBXDQB-UHFFFAOYSA-K cobalt(3+);2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Co+3].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O SCNCIXKLOBXDQB-UHFFFAOYSA-K 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- KUMNEOGIHFCNQW-UHFFFAOYSA-N diphenyl phosphite Chemical compound C=1C=CC=CC=1OP([O-])OC1=CC=CC=C1 KUMNEOGIHFCNQW-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002484 inorganic compounds Chemical class 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 229940006461 iodide ion Drugs 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- MEEXGIVWQPBKHB-UHFFFAOYSA-N methyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CCC(CO)C2C2CC(C(=O)OC)C1C2 MEEXGIVWQPBKHB-UHFFFAOYSA-N 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229940078552 o-xylene Drugs 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
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- 229920001225 polyester resin Polymers 0.000 description 2
- 239000004645 polyester resin Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 229940070891 pyridium Drugs 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
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- 239000004065 semiconductor Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
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- 239000000126 substance Substances 0.000 description 2
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 2
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- YFZDLRVCXDBOPH-UHFFFAOYSA-N tetraheptylazanium Chemical compound CCCCCCC[N+](CCCCCCC)(CCCCCCC)CCCCCCC YFZDLRVCXDBOPH-UHFFFAOYSA-N 0.000 description 2
- DTIFFPXSSXFQCJ-UHFFFAOYSA-N tetrahexylazanium Chemical compound CCCCCC[N+](CCCCCC)(CCCCCC)CCCCCC DTIFFPXSSXFQCJ-UHFFFAOYSA-N 0.000 description 2
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- CHYBTAZWINMGHA-UHFFFAOYSA-N tetraoctylazanium Chemical compound CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC CHYBTAZWINMGHA-UHFFFAOYSA-N 0.000 description 2
- GJSGYPDDPQRWPK-UHFFFAOYSA-N tetrapentylammonium Chemical compound CCCCC[N+](CCCCC)(CCCCC)CCCCC GJSGYPDDPQRWPK-UHFFFAOYSA-N 0.000 description 2
- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 2
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 2
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
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- QDIVXRBKUJDKOS-UHFFFAOYSA-N 1-hexyl-2,3-dimethyl-2h-imidazole Chemical compound CCCCCCN1C=CN(C)C1C QDIVXRBKUJDKOS-UHFFFAOYSA-N 0.000 description 1
- MMJMYYUZGLJBST-UHFFFAOYSA-N 1-methyl-3-octadecylimidazol-1-ium Chemical compound CCCCCCCCCCCCCCCCCCN1C=C[N+](C)=C1 MMJMYYUZGLJBST-UHFFFAOYSA-N 0.000 description 1
- LSFWFJFDPRFPBK-UHFFFAOYSA-N 1-methyl-3-pentylimidazol-1-ium Chemical compound CCCCCN1C=C[N+](C)=C1 LSFWFJFDPRFPBK-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- AVMSWPWPYJVYKY-UHFFFAOYSA-N 2-Methylpropyl formate Chemical compound CC(C)COC=O AVMSWPWPYJVYKY-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
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- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 description 1
- UZXIJHSJEKWJHP-UHFFFAOYSA-N 4-(4-carboxycyclohexyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1CCC(C(O)=O)CC1 UZXIJHSJEKWJHP-UHFFFAOYSA-N 0.000 description 1
- NXTDOCORQDMSTJ-UHFFFAOYSA-N 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylic acid Chemical compound C1C2C3C(CO)CCC3C1CC2C(O)=O NXTDOCORQDMSTJ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- RBIKUZKSPHSCKA-UHFFFAOYSA-N C12C=CCC2C2CC(C(=O)OC)C1C2 Chemical compound C12C=CCC2C2CC(C(=O)OC)C1C2 RBIKUZKSPHSCKA-UHFFFAOYSA-N 0.000 description 1
- MDLVWFOLPOBNAX-UHFFFAOYSA-N C12CC(CO)CC2C2CC(C(=O)OC)C1C2 Chemical compound C12CC(CO)CC2C2CC(C(=O)OC)C1C2 MDLVWFOLPOBNAX-UHFFFAOYSA-N 0.000 description 1
- FGHZZZKCTIBZGS-UHFFFAOYSA-N C1CC2C3CCC(C3)(C2C1)C(=O)OCC4=CC=CC=C4 Chemical compound C1CC2C3CCC(C3)(C2C1)C(=O)OCC4=CC=CC=C4 FGHZZZKCTIBZGS-UHFFFAOYSA-N 0.000 description 1
- CDGGVNDFFCZIDT-UHFFFAOYSA-N COC(=O)C1C2C3CCCC3=C(C1)C2 Chemical compound COC(=O)C1C2C3CCCC3=C(C1)C2 CDGGVNDFFCZIDT-UHFFFAOYSA-N 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical class CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 1
- RMOUBSOVHSONPZ-UHFFFAOYSA-N Isopropyl formate Chemical compound CC(C)OC=O RMOUBSOVHSONPZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 1
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 230000006750 UV protection Effects 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HFLXXTFRXRJQJM-UHFFFAOYSA-N benzyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12C(CO)CCC2C2CC1CC2C(=O)OCC1=CC=CC=C1 HFLXXTFRXRJQJM-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- NBXGPDIOBTUSPO-UHFFFAOYSA-N butyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CCC(CO)C2C2CC(C(=O)OCCCC)C1C2 NBXGPDIOBTUSPO-UHFFFAOYSA-N 0.000 description 1
- BMQYZAZEDZWBTO-UHFFFAOYSA-N butyl 4-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CC(CO)CC2C2CC(C(=O)OCCCC)C1C2 BMQYZAZEDZWBTO-UHFFFAOYSA-N 0.000 description 1
- KJCMWAFKVJRRQQ-UHFFFAOYSA-N butyl 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12C(CO)CCC2C2CC(C(=O)OCCCC)C1C2 KJCMWAFKVJRRQQ-UHFFFAOYSA-N 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
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000006473 carboxylation reaction Methods 0.000 description 1
- RLGQACBPNDBWTB-UHFFFAOYSA-N cetyltrimethylammonium ion Chemical compound CCCCCCCCCCCCCCCC[N+](C)(C)C RLGQACBPNDBWTB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 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 1
- GVRWIAHBVAYKIZ-UHFFFAOYSA-N dec-3-ene Chemical group CCCCCCC=CCC GVRWIAHBVAYKIZ-UHFFFAOYSA-N 0.000 description 1
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical group CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- MTWFVFBRPYYKPP-UHFFFAOYSA-N ethenyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C1C2C3C(CO)CCC3C1C(C(=O)OC=C)C2 MTWFVFBRPYYKPP-UHFFFAOYSA-N 0.000 description 1
- SVRUHZVGHOVQLW-UHFFFAOYSA-N ethenyl 4-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C=COC(=O)C1CC2CC1C1C2CC(CO)C1 SVRUHZVGHOVQLW-UHFFFAOYSA-N 0.000 description 1
- KVHYXHUOHIBEOJ-UHFFFAOYSA-N ethenyl 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C1C2C3C(CO)CCC3C1CC2C(=O)OC=C KVHYXHUOHIBEOJ-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- BCWFDMQUXXNNEV-UHFFFAOYSA-N ethyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CCC(CO)C2C2CC(C(=O)OCC)C1C2 BCWFDMQUXXNNEV-UHFFFAOYSA-N 0.000 description 1
- FJADRJISVPJBNE-UHFFFAOYSA-N ethyl 4-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CC(CO)CC2C2CC(C(=O)OCC)C1C2 FJADRJISVPJBNE-UHFFFAOYSA-N 0.000 description 1
- GPFPJDPVTBCSRD-UHFFFAOYSA-N ethyl 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12C(CO)CCC2C2CC(C(=O)OCC)C1C2 GPFPJDPVTBCSRD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- XKYICAQFSCFURC-UHFFFAOYSA-N isoamyl formate Chemical compound CC(C)CCOC=O XKYICAQFSCFURC-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 239000012567 medical material Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- HOHGZFRLTPBMKO-UHFFFAOYSA-N methyl 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12C(CO)CCC2C2CC(C(=O)OC)C1C2 HOHGZFRLTPBMKO-UHFFFAOYSA-N 0.000 description 1
- CAAULPUQFIIOTL-UHFFFAOYSA-L methyl phosphate(2-) Chemical compound COP([O-])([O-])=O CAAULPUQFIIOTL-UHFFFAOYSA-L 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- RKNAUWKZCIAWGJ-UHFFFAOYSA-N pentyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CCC(CO)C2C2CC(C(=O)OCCCCC)C1C2 RKNAUWKZCIAWGJ-UHFFFAOYSA-N 0.000 description 1
- BTWIDEZZKQXBAD-UHFFFAOYSA-N pentyl 4-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CC(CO)CC2C2CC(C(=O)OCCCCC)C1C2 BTWIDEZZKQXBAD-UHFFFAOYSA-N 0.000 description 1
- TXFYBXBWGHVXSI-UHFFFAOYSA-N pentyl 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12C(CO)CCC2C2CC(C(=O)OCCCCC)C1C2 TXFYBXBWGHVXSI-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- XQPUYDDVOXVTEL-UHFFFAOYSA-N propyl 3-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CCC(CO)C2C2CC(C(=O)OCCC)C1C2 XQPUYDDVOXVTEL-UHFFFAOYSA-N 0.000 description 1
- GGKRQXRTZDABEU-UHFFFAOYSA-N propyl 4-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12CC(CO)CC2C2CC(C(=O)OCCC)C1C2 GGKRQXRTZDABEU-UHFFFAOYSA-N 0.000 description 1
- KLRMSDIDWJPGNZ-UHFFFAOYSA-N propyl 5-(hydroxymethyl)tricyclo[5.2.1.02,6]decane-8-carboxylate Chemical compound C12C(CO)CCC2C2CC(C(=O)OCCC)C1C2 KLRMSDIDWJPGNZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
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Abstract
Description
従来から、耐熱に優れる脂環式ポリエステル等の原料が求められていた。
本発明の主題は、特願2009−203753(2009年9月3日出願)に記載されており、参照のために上記の明細書を全体的にここに組み込むものとする。
一般式(I)中、2つの置換基、すなわち−C(O)OR及び−CH2OHの結合位置は特に限定されないが、−C(O)ORはトリシクロデカン基の8位又は9位に、−CH2OHはトリシクロデカン基の3位又は4位に結合することが好ましい。
上記トリシクロデカンモノメタノールモノカルボン酸及びその誘導体の具体例としては、4−ヒドロキシメチル−8−カルボキシ−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−カルボキシ−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−カルボキシ−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−メトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−メトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−メトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−エトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−エトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−エトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−プロポキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−プロポキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−プロポキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−ブトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−ブトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−ブトキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−ペントキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−ペントキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−ペントキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−ビニルオキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−ビニルオキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−ビニルオキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、4−ヒドロキシメチル−8−ベンジルオキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−8−ベンジルオキシカルボニル−トリシクロ〔5.2.1.02,6〕デカン、3−ヒドロキシメチル−9−ベンジルオキシカルボニル−トリシクロ〔5.2.1.02,6〕デカンなどが挙げられる。
かかる上記一般式(II)で表される化合物を得る方法としては、例えば、上記式(III)で表されるジシクロペンタジエンにギ酸化合物(HC(O)OR)を反応させる方法、あるいはジシクロペンタジエンに一酸化炭素とアルコール(ROH)とを反応させる方法が挙げられる。一般式(II)で表される化合物を得る方法に特に制限は無いが、その作業性、安全性及びコスト等を考慮すると、ジシクロペンタジエンにギ酸化合物(HCOOR)を反応させる方法が好ましい。ギ酸化合物として、Rが水素であるギ酸を用いる場合は、カルボキシル化反応が起こりジシクロペンタジエンにカルボキシル基を付加させることができる。Rが炭素数1〜5のアルキル基、ビニル基又はベンジル基であるギ酸エステルを用いる場合はヒドロエステル化反応が起こりジシクロペンタジエンにヒドロエステル基を付加することができる。
ジシクロペンタジエンのヒドロエステル化反応は、特に制限は無く、例えば、遷移金属錯体触媒等を用いてギ酸エステルと反応させる方法が挙げられ、ルテニウム化合物と、コバルト化合物と、ハロゲン化物塩とを含む触媒系の存在下で、ジシクロペンタジエンとギ酸エステルを反応させる方法が好ましい。
一般式(II)で表される化合物のヒドロホルミル化反応は、特に制限は無く、例えば、触媒講座第7巻、触媒学会編、講談社(1985)に記載されている、コバルト、ルテニウム、ロジウム等の遷移金属錯体触媒を用いて、一酸化炭素と水素をと反応させてアルデヒドを付加した後、さらに水素化する方法、特許第3343585号明細書あるいは特許第3702343号明細書等に記載されている、二酸化炭素、水素及びルテニウム化合物触媒を用いてヒドロホルミル化する方法、国際公開第2009/041192号に記載されている、二酸化炭素、水素及びルテニウム化合物とコバルト化合物を組み合わせた触媒系を用いてヒドロホルミル化する方法などを使用することができる。作業性、安全性、反応性等の観点から、二酸化炭素、水素及びルテニウム化合物とコバルト化合物を組み合わせた触媒系を用いてヒドロホルミル化する方法が好ましい。なお、上記の文献を参照のために、全体的にここに組み込むものとする。
本発明のトリシクロデカンモノメタノールモノカルボン酸及びその誘導体は脂環式ポリエステルの原料として有用であり、それを用いたポリエステルは耐熱性および透明性に優れるため、半導体・液晶に用いられる電子部品、光ファイバー、光学レンズ等に代表される光学材料、さらには、ディスプレイ関連材料、医療用材料として使用することができる。
〔トリシクロデカンモノカルボン酸メチルの合成〕
以上のようにして得られた、トリシクロデカンモノメタノールモノカルボン酸メチルを減圧蒸留によって単離し、1H−NMRスペクトルおよびIRスペクトルを測定した。
なお、1H−NMRスペクトルは、試料をジメチルスルホキシド(DMSO−d6)に溶かして溶液とし、φ5mmの試料管に入れて、BRUKER社製、400MHz核磁気共鳴装置「AV400M」を用いて測定した。また、IRスペクトルは、フーリエ変換赤外分光光度計(日本電子製JIR−6500)を用いて測定した。
1H−NMRスペクトルを図1に示す。それぞれのプロトンが下記に示すように帰属された。解析の便宜上、下記式で表される4−ヒドロキシメチル−8−カルボキシ−トリシクロ〔5.2.1.02,6〕デカンを例として示す。
プロトン(2):2.4ppm付近のピーク
プロトン(3):1.2ppm付近及び1.7ppm付近のピーク
プロトン(4):2.3ppm付近のピーク
プロトン(5):1.2ppm付近及び1.8ppm付近のピーク
プロトン(6):2.6ppm付近のピーク
プロトン(7):2.1ppm付近のピーク
プロトン(8):1.9ppm付近のピーク
プロトン(9):0.9ppm付近及び1.7ppm付近のピーク
プロトン(10):1.4〜1.5ppm付近のピーク
プロトン(11):3.2ppm付近のピーク
プロトン(12):4.4ppm付近のピーク
プロトン(13):3.6ppm付近のピーク
攪拌機、窒素導入管及び冷却管を備えた10mlフラスコに、実施例1で得られたトリシクロデカンモノメタノールモノカルボン酸メチル 5g及びチタンテトライソプロポキシド 0.5gを仕込み、130℃のオイルバス中で6時間撹拌し、数平均分子量が30,000のトリシクロデカン骨格を持つポリエステルを得た。
結果を表1に示す。
(1)ガラス転移温度(Tg)
示差走査熱量計((株)リガク製 8230型 DSC)で測定した。
昇温速度 :5℃/min
雰 囲 気:空気
(2)熱分解開始温度(5%重量減少温度、Td5)
示差熱天秤(セイコー電子(株)製 5200型 TG−DTA)で測定した。
昇温速度 :5℃/min
雰 囲 気:空気
Claims (2)
- 下記一般式(I)で表されるトリシクロデカンモノメタノールモノカルボン酸及びその誘導体。
- 下記一般式(II)で表される化合物をヒドロホルミル化することによって得られるトリシクロデカンモノメタノールモノカルボン酸及びその誘導体。
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