JP7041925B2 - カーボネート誘導体の製造方法 - Google Patents
カーボネート誘導体の製造方法 Download PDFInfo
- Publication number
- JP7041925B2 JP7041925B2 JP2019519162A JP2019519162A JP7041925B2 JP 7041925 B2 JP7041925 B2 JP 7041925B2 JP 2019519162 A JP2019519162 A JP 2019519162A JP 2019519162 A JP2019519162 A JP 2019519162A JP 7041925 B2 JP7041925 B2 JP 7041925B2
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- JP
- Japan
- Prior art keywords
- group
- bisphenol
- reaction
- carbonate
- containing compound
- 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 36
- 150000004649 carbonic acid derivatives Chemical class 0.000 title claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 140
- 230000000269 nucleophilic effect Effects 0.000 claims description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 50
- 150000008282 halocarbons Chemical class 0.000 claims description 46
- 125000000524 functional group Chemical group 0.000 claims description 43
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 37
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 34
- -1 alkali metal hydrogen carbonate Chemical class 0.000 claims description 33
- 239000002585 base Substances 0.000 claims description 30
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 20
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 20
- 229920000515 polycarbonate Polymers 0.000 claims description 17
- 239000004417 polycarbonate Substances 0.000 claims description 17
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 16
- 150000007529 inorganic bases Chemical class 0.000 claims description 15
- 150000005676 cyclic carbonates Chemical class 0.000 claims description 10
- 150000005678 chain carbonates Chemical class 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000005549 heteroarylene group Chemical group 0.000 claims description 9
- 125000000732 arylene group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 claims description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 125000005915 C6-C14 aryl group Chemical group 0.000 claims description 5
- 230000001678 irradiating effect Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 claims description 3
- FVKFHMNJTHKMRX-UHFFFAOYSA-N 3,4,6,7,8,9-hexahydro-2H-pyrimido[1,2-a]pyrimidine Chemical group C1CCN2CCCNC2=N1 FVKFHMNJTHKMRX-UHFFFAOYSA-N 0.000 claims description 3
- BATCUENAARTUKW-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-diphenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BATCUENAARTUKW-UHFFFAOYSA-N 0.000 claims description 3
- UMPGNGRIGSEMTC-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)-3,3,5-trimethylcyclohexyl]phenol Chemical compound C1C(C)CC(C)(C)CC1(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UMPGNGRIGSEMTC-UHFFFAOYSA-N 0.000 claims description 3
- VOWWYDCFAISREI-UHFFFAOYSA-N Bisphenol AP Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=CC=C1 VOWWYDCFAISREI-UHFFFAOYSA-N 0.000 claims description 3
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 claims description 3
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 132
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- 239000000243 solution Substances 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 30
- 238000003786 synthesis reaction Methods 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- 238000000034 method Methods 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 239000000843 powder Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 18
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 18
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 18
- 229910052753 mercury Inorganic materials 0.000 description 18
- 239000012074 organic phase Substances 0.000 description 17
- 239000002904 solvent Substances 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 15
- 230000005587 bubbling Effects 0.000 description 14
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 12
- 229910001882 dioxygen Inorganic materials 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 230000035484 reaction time Effects 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 9
- 238000002955 isolation Methods 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 8
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- ULSJTMWWIWWXIW-UHFFFAOYSA-N carbonic acid;phenol Chemical compound OC(O)=O.OC1=CC=CC=C1.OC1=CC=CC=C1 ULSJTMWWIWWXIW-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 5
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
- 229910002091 carbon monoxide Inorganic materials 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 4
- 150000004651 carbonic acid esters Chemical class 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 4
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 229950005499 carbon tetrachloride Drugs 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000007530 organic bases Chemical group 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N 1,1,2-trichloroethane Chemical compound ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- JRNVQLOKVMWBFR-UHFFFAOYSA-N 1,2-benzenedithiol Chemical compound SC1=CC=CC=C1S JRNVQLOKVMWBFR-UHFFFAOYSA-N 0.000 description 2
- NZPSDGIEKAQVEZ-UHFFFAOYSA-N 1,3-benzodioxol-2-one Chemical compound C1=CC=CC2=C1OC(=O)O2 NZPSDGIEKAQVEZ-UHFFFAOYSA-N 0.000 description 2
- BGPJLYIFDLICMR-UHFFFAOYSA-N 1,4,2,3-dioxadithiolan-5-one Chemical group O=C1OSSO1 BGPJLYIFDLICMR-UHFFFAOYSA-N 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 2
- JYYNAJVZFGKDEQ-UHFFFAOYSA-N 2,4-Dimethylpyridine Chemical compound CC1=CC=NC(C)=C1 JYYNAJVZFGKDEQ-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 2
- 125000005012 alkyl thioether group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000003125 aqueous solvent Substances 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical class SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 2
- 229920000402 bisphenol A polycarbonate polymer Polymers 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 229950005228 bromoform Drugs 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- FJBFPHVGVWTDIP-UHFFFAOYSA-N dibromomethane Chemical compound BrCBr FJBFPHVGVWTDIP-UHFFFAOYSA-N 0.000 description 2
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
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- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 150000003939 benzylamines Chemical class 0.000 description 1
- AGJBSXZYDVLIEH-UHFFFAOYSA-N bis(phenylsulfanyl)methanone Chemical compound C=1C=CC=CC=1SC(=O)SC1=CC=CC=C1 AGJBSXZYDVLIEH-UHFFFAOYSA-N 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- JOHCVVJGGSABQY-UHFFFAOYSA-N carbon tetraiodide Chemical compound IC(I)(I)I JOHCVVJGGSABQY-UHFFFAOYSA-N 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical class SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 150000003946 cyclohexylamines Chemical class 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- OKQDSOXFNBWWJL-UHFFFAOYSA-N dihexyl carbonate Chemical compound CCCCCCOC(=O)OCCCCCC OKQDSOXFNBWWJL-UHFFFAOYSA-N 0.000 description 1
- 150000005205 dihydroxybenzenes Chemical class 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- HSNQKJVQUFYBBY-UHFFFAOYSA-N dipentyl carbonate Chemical compound CCCCCOC(=O)OCCCCC HSNQKJVQUFYBBY-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 239000008151 electrolyte solution Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- SUWOZRAXYHTFJX-UHFFFAOYSA-N ethane-1,2-dithiol methylsulfanylmethane Chemical compound CSC.C(CS)S.C(CS)S SUWOZRAXYHTFJX-UHFFFAOYSA-N 0.000 description 1
- 125000005677 ethinylene group Polymers [*:2]C#C[*:1] 0.000 description 1
- TUEYHEWXYWCDHA-UHFFFAOYSA-N ethyl 5-methylthiadiazole-4-carboxylate Chemical compound CCOC(=O)C=1N=NSC=1C TUEYHEWXYWCDHA-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Polymers [H]C#C* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 1
- WFSXUTWNNVIIIG-ZPUQHVIOSA-N glutaconaldehyde Chemical compound O\C=C\C=C\C=O WFSXUTWNNVIIIG-ZPUQHVIOSA-N 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- YVWGMAFXEJHFRO-UHFFFAOYSA-N halopropane Chemical compound FC(F)C(F)(F)CBr YVWGMAFXEJHFRO-UHFFFAOYSA-N 0.000 description 1
- 229950000188 halopropane Drugs 0.000 description 1
- VHHHONWQHHHLTI-UHFFFAOYSA-N hexachloroethane Chemical compound ClC(Cl)(Cl)C(Cl)(Cl)Cl VHHHONWQHHHLTI-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- HLTMVWQXGLNLCU-UHFFFAOYSA-N n'-[2-(dimethylamino)ethyl]ethane-1,2-diamine Chemical compound CN(C)CCNCCN HLTMVWQXGLNLCU-UHFFFAOYSA-N 0.000 description 1
- QATBRNFTOCXULG-UHFFFAOYSA-N n'-[2-(methylamino)ethyl]ethane-1,2-diamine Chemical compound CNCCNCCN QATBRNFTOCXULG-UHFFFAOYSA-N 0.000 description 1
- LWJQXXZIHDQCPT-UHFFFAOYSA-N n'-[2-[2-(dimethylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CN(C)CCNCCNCCN LWJQXXZIHDQCPT-UHFFFAOYSA-N 0.000 description 1
- VELRFBWXSQBZEM-UHFFFAOYSA-N n'-[2-[2-(methylamino)ethylamino]ethyl]ethane-1,2-diamine Chemical compound CNCCNCCNCCN VELRFBWXSQBZEM-UHFFFAOYSA-N 0.000 description 1
- BNUHBJSGYGOLSN-UHFFFAOYSA-N n'-[2-[2-[2-(dimethylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound CN(C)CCNCCNCCNCCN BNUHBJSGYGOLSN-UHFFFAOYSA-N 0.000 description 1
- PCEDONPCDMBJPI-UHFFFAOYSA-N n'-[2-[2-[2-(methylamino)ethylamino]ethylamino]ethyl]ethane-1,2-diamine Chemical compound CNCCNCCNCCNCCN PCEDONPCDMBJPI-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- ANORDWOIBSUYBN-UHFFFAOYSA-N n-chloro-1-phenylmethanamine Chemical compound ClNCC1=CC=CC=C1 ANORDWOIBSUYBN-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Description
そこで本発明は、安全かつ効率的にカーボネート誘導体を製造するための方法を提供することを目的とする。
以下、本発明を示す。
塩素原子、臭素原子およびヨウ素原子からなる群から選択される1種以上のハロゲン原子を有するC1-4ハロゲン化炭化水素、求核性官能基含有化合物、および塩基を含む組成物に酸素存在下で光照射し、
前記求核性官能基含有化合物が下式(i)で表される化合物であり且つ前記カーボネート誘導体が下式(I)で表される鎖状カーボネート誘導体であるか、または、
前記求核性官能基含有化合物が下式(ii)で表される化合物であり且つ前記カーボネート誘導体が下式(II-1)で表される単位を含むポリカーボネート誘導体もしくは下式(II-2)で表される環状カーボネート誘導体であり、
前記塩基として、複素環式芳香族アミン、非求核性強塩基、および無機塩基から実質的になる群より選択される1以上の塩基を用いる、カーボネート誘導体の製造方法。
(i) R1-A-H
(ii) H-A-R2-A-H
(I) R1-A-C(=O)-A-R1
(II-1) [-A-R2-A-C(=O)-]
Aは、O、SまたはNR3(R3は、HまたはC1-4アルキル基であるか、またはR1およびNと共に窒素含有ヘテロシクリル基を形成してもよい)であり、
R1は、C6-14アリール基、C4-14ヘテロアリール基またはC2-24アルキルポリオキシアルキレン基であり、
R2は、C2-10アルキレン基、C6-14アリーレン基、C4-14ヘテロアリーレン基またはC2-24ポリオキシアルキレン基である。]
本発明に係る反応においてC1-4ハロゲン化炭化水素は、おそらく照射光と酸素により分解され、ハロゲン化カルボニルまたはハロゲン化カルボニル様の化合物に変換され、水酸基含有化合物と反応してカーボネート誘導体が生成すると考えられる。たとえ有害なハロゲン化カルボニルが生成しても、ハロゲン化カルボニルは反応性が極めて高いために水酸基含有化合物と直ぐに反応し、反応液外へは漏出しないか、或いは漏出してもその漏出量は僅かである。なお、例えばハロゲン化カルボニルであるホスゲンは非常に毒性が高く、その運搬などには厳しい規制が課せられているが、C1-4ハロゲン化炭化水素は勿論それほど危険ではない。但し、後述するように本発明に係る反応は無機塩基水溶液の存在下でも進行することから、本発明に係る反応にはハロゲン化カルボニルまたはハロゲン化カルボニル様の化合物が介在していない可能性もある。
本発明において「求核性官能基含有化合物」とは、求核性の酸素原子、硫黄原子、および/または窒素原子を含む求核性官能基を含む化合物であって、式(i)または式(ii)で表される化合物であり、それぞれ「求核性官能基含有化合物(i)」または「求核性官能基含有化合物(ii)」と略記する場合がある。本発明で用いる求核性官能基含有化合物は、フッ素原子を置換基として有さない。その結果、本発明方法で製造されるカーボネート誘導体もフッ素原子を置換基として有さない。また、本発明では特定の求核性官能基含有化合物を用いることによって、カーボネート誘導体までの反応の進行が可能になる。
(i) R1-A-H
(ii) H-A-R2-A-H
(I) R1-A-C(=O)-A-R1
(II-1) [-A-R2-A-C(=O)-]
Aは、O、SまたはNR3(R3は、HまたはC1-4アルキル基であるか、またはR1およびNと共に窒素含有ヘテロシクリル基を形成してもよい)であり、
R1は、C6-14アリール基、C4-14ヘテロアリール基またはC2-24アルキルポリオキシアルキレン基であり、
R2は、C2-10アルキレン基、C6-14アリーレン基、C4-14ヘテロアリーレン基またはC2-24ポリオキシアルキレン基である。]
(ii-1) H-A-R21-A-H
(ii-2) H-A-R22-R23-R24-A-H
[式中、
Aは上記と同義を示し、
R21は、C2-10アルキレン基、C6-14アリーレン基またはC4-14ヘテロアリーレン基であり、
R22とR24は、それぞれ独立にC6-14アリーレン基またはC4-14ヘテロアリーレン基であり、
R23は、C1-10アルキレン基である。]
本発明方法においては、複素環式芳香族アミン、非求核性強塩基、および無機塩基から実質的になる群より選択される1以上の塩基を用いる。当該塩基により、ポリカーボネート誘導体が生成するまで反応が進行すると考えられる。
本発明方法は、上記C1-4ハロゲン化炭化水素、求核性官能基含有化合物、および塩基を含む組成物に、酸素存在下で光照射する工程を含む。
メタノールの代わりにエタノールを用いた以外は上記比較例1と同様にして、反応を行ったが、3時間の反応後においても、反応の進行は認められなかった。比較例1の結果と合わせて考えれば、本発明方法は一価アルコールには適用し難いことが明らかとなった。
メタノールの代わりにフェノール(0.94g,10mmol)を用い、ピリジンの使用量をフェノールに対して3.5倍モルに調整し、反応時間を2時間にした以外は上記比較例1と同様にして、反応を行った。反応終了後、反応液に水とジクロロメタンを加えて分液し、有機相を無水硫酸ナトリウムで乾燥した後、溶媒を減圧留去した。得られた固体をジクロロメタンとn-ヘキサンから再結晶し、白色固体状の目的化合物である炭酸ジフェノールを得た(単離収率:61%)。
フェノールに対して5倍モルのピリジンを用い、反応時間を1時間にした以外は上記実施例1(1)と同様にして、白色固体状の目的化合物である炭酸ジフェノールを得た(単離収率:99%超)。
ピリジンの代わりに2,6-ルチジンを用い、反応時間を1時間にした以外は上記実施例1(1)と同様にして、目的化合物である炭酸ジフェノールを得た(単離収率:60%)。
クロロホルムの代わりに四塩化炭素(25mL)を用い、フェノールに対して5倍モルのピリジンを用いた以外は上記実施例1(1)と同様にして、反応を行った。反応終了後、反応液に水とジクロロメタンを加えて分液し、有機相を無水硫酸ナトリウムで乾燥した後、溶媒を減圧留去した。得られた固体をジクロロメタンとn-ヘキサンから再結晶し、白色固体状の目的化合物である炭酸ジフェノールを得た(単離収率:69%)。
ピリジンの代わりにトリエチルアミンを用いた以外は上記実施例1(2)と同様にして反応を行った。しかし、単離されたのは少量のタール状の黒色物質であり、目的化合物である炭酸ジフェノールを単離することはできなかった。この様に有機塩基としてトリエチルアミンを用いた場合には炭酸ジフェノールは得られなかった一方で、上記実施例1(2)の通り、有機塩基をトリエチルアミンからピリジンに変更するのみで炭酸ジフェノールが99%超の収率で得られた。
また、得られたポリ炭酸ビスフェノールAを下記の条件のゲル浸透クロマトグラフィー(GPC)で分析し、分子量を求めた。結果を表1に示す。
装置: 高速GPC装置(「HLC-8320GPC」東ソー社製)
カラム: 超高分子用カラム(「TSKgel GMHHR-H×2」東ソー社製)
移動相: クロロホルム 流速: 1.0mL/min
オーブン温度: 40℃ 濃度: 0.3w/v%
注入量: 100μL 分子量標準: ポリスチレン
検出器: RI
1H-NMR(400MHz,CDCl3) δ4.28(t,J=4.8Hz,-CO2CH2-),3.73(t,J=4.8Hz,-CH2-),3.68-3.63(m,-CH2-);
FAB-MS: m/z519,739,958;
IR(KBr): 2955,2891,1740,1459,1396,1354,1271,1100,1029,950,864,791cm-1
上記の通り、無機塩基の水溶液を用いてもカーボネート誘導体を製造することができた。無機塩基の水溶液はホスゲンを分解するために用いられるものであることから、上記の実験結果は全く予想外であり、本発明に係る反応はホスゲンを経由していない可能性もあると考えられた。
なお、最初に得られた沈殿は溶媒に不溶であり、濾液から得られた粉末はDMSOなどに可溶であることから、両粉末は分子量が異なると考えられる。
得られたポリ炭酸ビスフェノールAの分子量を上記実施例5と同様の条件により求めた。結果を表2に示す。
水酸化ナトリウム水溶液の代わりにジアザビシクロウンデセン(60mmol)を用いた以外は上記実施例8と同様にして、20℃で2時間反応を行った。次いで、更に50℃で15分間反応を行った。反応後、水を添加し、一晩静置してから分液した。有機相を無水硫酸ナトリウムで乾燥した後、減圧濃縮した。残渣をヘキサンで洗浄し、70℃で減圧乾燥した。更に、ジクロロメタンとヘキサンで洗浄した後、70℃で減圧乾燥することにより、薄オレンジ色粉末を得た(収率:>99%)。得られた粉末を1H-NMRとIRで分析したところ、目的化合物が生成していることが確認された。
4: 撹拌子, 5: 熱媒または冷媒, 6: 筒状反応容器
Claims (9)
- カーボネート誘導体を製造するための方法であって、
塩素原子、臭素原子およびヨウ素原子からなる群から選択される1種以上のハロゲン原子を有するC1-4ハロゲン化炭化水素、求核性官能基含有化合物、および塩基を含む組成物に酸素存在下で光照射し、
前記求核性官能基含有化合物が下式(i)で表される化合物であり且つ前記カーボネート誘導体が下式(I)で表される鎖状カーボネート誘導体であるか、または、
前記求核性官能基含有化合物が下式(ii)で表される化合物、ビスフェノールA、ビスフェノールAP、ビスフェノールB、ビスフェノールBP、ビスフェノールTMC、もしくはビスフェノールZであり、前記カーボネート誘導体が下式(II-1)で表される単位を含むポリカーボネート誘導体、ビスフェノールA、ビスフェノールAP、ビスフェノールB、ビスフェノールBP、ビスフェノールTMC、もしくはビスフェノールZのポリカーボネートエステル、もしくは下式(II-2)で表される環状カーボネート誘導体であり、
前記塩基として、複素環式芳香族アミン、非求核性強塩基、および無機塩基から実質的になる群より選択される1以上の塩基を用いる、カーボネート誘導体の製造方法。
(i) R1-A-H
(ii) H-A-R2-A-H
(I) R1-A-C(=O)-A-R1
(II-1) [-A-R2-A-C(=O)-]
Aは、O、SまたはNR3(R3は、HまたはC1-4アルキル基であるか、またはR1およびNと共に窒素含有ヘテロシクリル基を形成してもよい)であり、
R1は、C6-14アリール基、C4-14ヘテロアリール基またはC2-24アルキルポリオキシアルキレン基であり、
R2は、C2-10アルキレン基、C6-14アリーレン基、C4-14ヘテロアリーレン基またはC2-24ポリオキシアルキレン基である。] - 前記C1-4ハロゲン化炭化水素がC1-4ポリハロゲン化炭化水素である請求項1に記載の製造方法。
- 前記C1-4ハロゲン化炭化水素がクロロホルムである請求項1に記載の製造方法。
- 前記複素環式芳香族アミンが、ピリジン、ピコリンまたはルチジンである請求項1~3のいずれかに記載の製造方法。
- 前記非求核性強塩基が、1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン、7-メチル-1,5,7-トリアザビシクロ[4.4.0]デカ-5-エン、1,8-ジアザビシクロ[5.4.0]ウンデカ-7-エン、1,5-ジアザビシクロ[4.3.0]ノナ-5-エンまたは1,1,3,3-テトラメチルグアニジンである請求項1~4のいずれかに記載の製造方法。
- 前記無機塩基が、アルカリ金属水酸化物、アルカリ金属炭酸水素塩またはアルカリ金属炭酸塩である請求項1~5のいずれかに記載の製造方法。
- 前記C1-4ハロゲン化炭化水素に対して0.001倍モル以上1倍モル以下の前記求核性官能基含有化合物を用いる請求項1~6のいずれかに記載の製造方法。
- 前記求核性官能基含有化合物に対して1.5倍モル以上10倍モル以下の前記塩基を用いる請求項1~7のいずれかに記載の製造方法。
- 前記組成物に照射する光が180nm以上500nm以下の波長の光である請求項1~8のいずれかに記載の製造方法。
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