JP2012507478A - ビニル化合物を用いたジアルキルホスフィン酸、−エステル及び−塩の製造方法及びそれらの使用 - Google Patents
ビニル化合物を用いたジアルキルホスフィン酸、−エステル及び−塩の製造方法及びそれらの使用 Download PDFInfo
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- JP2012507478A JP2012507478A JP2011533570A JP2011533570A JP2012507478A JP 2012507478 A JP2012507478 A JP 2012507478A JP 2011533570 A JP2011533570 A JP 2011533570A JP 2011533570 A JP2011533570 A JP 2011533570A JP 2012507478 A JP2012507478 A JP 2012507478A
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- Prior art keywords
- acid
- bis
- ester
- alkyl
- monocarboxy
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- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 39
- 150000003624 transition metals Chemical class 0.000 claims abstract description 36
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 23
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- 229910052725 zinc Inorganic materials 0.000 claims abstract description 21
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- 229910052700 potassium Inorganic materials 0.000 claims abstract description 18
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 5
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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- LFSBSHDDAGNCTM-UHFFFAOYSA-N cobalt(2+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[Ti+4].[Co+2] LFSBSHDDAGNCTM-UHFFFAOYSA-N 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- BSVQJWUUZCXSOL-UHFFFAOYSA-N cyclohexylsulfonyl ethaneperoxoate Chemical compound CC(=O)OOS(=O)(=O)C1CCCCC1 BSVQJWUUZCXSOL-UHFFFAOYSA-N 0.000 description 1
- ICPMUWPXCAVOOQ-UHFFFAOYSA-N cycloocta-1,3,5-triene Chemical compound C1CC=CC=CC=C1 ICPMUWPXCAVOOQ-UHFFFAOYSA-N 0.000 description 1
- LRKNOSLOHGOJSU-UHFFFAOYSA-N cycloocta-1,5-diene;cycloocta-1,3,5-triene;ruthenium Chemical compound [Ru].C1CC=CCCC=C1.C1CC=CC=CC=C1 LRKNOSLOHGOJSU-UHFFFAOYSA-N 0.000 description 1
- AKJCIXVJQZAAGQ-UHFFFAOYSA-N cyclopenta-1,3-diene dicyclopentyl-[[2-(dicyclopentylphosphanylmethyl)cyclopenta-1,3-dien-1-yl]methyl]phosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C(P(C1CCCC1)C1CCCC1)c1ccc[c-]1CP(C1CCCC1)C1CCCC1 AKJCIXVJQZAAGQ-UHFFFAOYSA-N 0.000 description 1
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- 238000000354 decomposition reaction Methods 0.000 description 1
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- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
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- XCZSHKNZWNNEKE-UHFFFAOYSA-N dicyclohexyl(5-dicyclohexylphosphanylpentyl)phosphane Chemical compound C1CCCCC1P(C1CCCCC1)CCCCCP(C1CCCCC1)C1CCCCC1 XCZSHKNZWNNEKE-UHFFFAOYSA-N 0.000 description 1
- BSSFMHHLTVJPGW-UHFFFAOYSA-N dicyclohexyl-[2-(2-dicyclohexylphosphanylphenyl)phenyl]phosphane Chemical group C1CCCCC1P(C=1C(=CC=CC=1)C=1C(=CC=CC=1)P(C1CCCCC1)C1CCCCC1)C1CCCCC1 BSSFMHHLTVJPGW-UHFFFAOYSA-N 0.000 description 1
- GKDLOBHSFWDXEZ-UHFFFAOYSA-N dicyclopentyl-(3-dicyclopentylphosphanylphenyl)phosphane Chemical compound C1CCCC1P(C=1C=C(C=CC=1)P(C1CCCC1)C1CCCC1)C1CCCC1 GKDLOBHSFWDXEZ-UHFFFAOYSA-N 0.000 description 1
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- NUDLYJBPZJQGBY-UHFFFAOYSA-N dihydroxy-methyl-diphenyl-lambda5-phosphane Chemical compound C=1C=CC=CC=1P(O)(O)(C)C1=CC=CC=C1 NUDLYJBPZJQGBY-UHFFFAOYSA-N 0.000 description 1
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- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- LXWJYIBQIPSFSE-UHFFFAOYSA-N dipotassium;nickel(2+);tetracyanide Chemical compound [K+].[K+].[Ni+2].N#[C-].N#[C-].N#[C-].N#[C-] LXWJYIBQIPSFSE-UHFFFAOYSA-N 0.000 description 1
- JZBWUTVDIDNCMW-UHFFFAOYSA-L dipotassium;oxido sulfate Chemical compound [K+].[K+].[O-]OS([O-])(=O)=O JZBWUTVDIDNCMW-UHFFFAOYSA-L 0.000 description 1
- QFTWTIKOKWPUAM-UHFFFAOYSA-N dipotassium;platinum(2+);tetracyanide Chemical compound [K+].[K+].[Pt+2].N#[C-].N#[C-].N#[C-].N#[C-] QFTWTIKOKWPUAM-UHFFFAOYSA-N 0.000 description 1
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- 239000006185 dispersion Substances 0.000 description 1
- CNXMDTWQWLGCPE-UHFFFAOYSA-N ditert-butyl-(2-phenylphenyl)phosphane Chemical compound CC(C)(C)P(C(C)(C)C)C1=CC=CC=C1C1=CC=CC=C1 CNXMDTWQWLGCPE-UHFFFAOYSA-N 0.000 description 1
- ISVIYPMMKCNZPF-UHFFFAOYSA-N ditert-butyl-[[2-(1-phosphatricyclo[3.3.1.13,7]decan-2-ylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=CC=C1CPC1P(C2)CC3CC2CC1C3 ISVIYPMMKCNZPF-UHFFFAOYSA-N 0.000 description 1
- SFCNPIUDAIFHRD-UHFFFAOYSA-N ditert-butyl-[[2-(ditert-butylphosphanylmethyl)phenyl]methyl]phosphane Chemical compound CC(C)(C)P(C(C)(C)C)CC1=CC=CC=C1CP(C(C)(C)C)C(C)(C)C SFCNPIUDAIFHRD-UHFFFAOYSA-N 0.000 description 1
- ZOIVSVWBENBHNT-UHFFFAOYSA-N dizinc;silicate Chemical compound [Zn+2].[Zn+2].[O-][Si]([O-])([O-])[O-] ZOIVSVWBENBHNT-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
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- RZUASTIKPBCXPU-UHFFFAOYSA-N ethene;platinum;triphenylphosphane Chemical compound [Pt].C=C.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RZUASTIKPBCXPU-UHFFFAOYSA-N 0.000 description 1
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- XWUFPNLBTGIAFF-UHFFFAOYSA-N ethenyl(ethyl)phosphinic acid Chemical compound CCP(O)(=O)C=C XWUFPNLBTGIAFF-UHFFFAOYSA-N 0.000 description 1
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- MFGZXPGKKJMZIY-UHFFFAOYSA-N ethyl 5-amino-1-(4-sulfamoylphenyl)pyrazole-4-carboxylate Chemical compound NC1=C(C(=O)OCC)C=NN1C1=CC=C(S(N)(=O)=O)C=C1 MFGZXPGKKJMZIY-UHFFFAOYSA-N 0.000 description 1
- HJOXDQXNLHULDM-UHFFFAOYSA-N ethyl(2-hydroxyethoxy)phosphinous acid Chemical compound CCP(O)OCCO HJOXDQXNLHULDM-UHFFFAOYSA-N 0.000 description 1
- BEIATBRTFTWWGI-UHFFFAOYSA-N ethyl-[3-(4-hydroxybutoxy)-3-oxopropyl]phosphinic acid Chemical compound CCP(O)(=O)CCC(=O)OCCCCO BEIATBRTFTWWGI-UHFFFAOYSA-N 0.000 description 1
- SFNALCNOMXIBKG-UHFFFAOYSA-N ethylene glycol monododecyl ether Chemical compound CCCCCCCCCCCCOCCO SFNALCNOMXIBKG-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000004079 fireproofing Methods 0.000 description 1
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- 238000007306 functionalization reaction Methods 0.000 description 1
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- 150000002332 glycine derivatives Chemical class 0.000 description 1
- MSNOMDLPLDYDME-UHFFFAOYSA-N gold nickel Chemical compound [Ni].[Au] MSNOMDLPLDYDME-UHFFFAOYSA-N 0.000 description 1
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- CBMIPXHVOVTTTL-UHFFFAOYSA-N gold(3+) Chemical compound [Au+3] CBMIPXHVOVTTTL-UHFFFAOYSA-N 0.000 description 1
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- 239000011984 grubbs catalyst Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
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- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- YYWGABLTRMRUIT-HWWQOWPSSA-N huperzine b Chemical compound N1CCC[C@@H]2[C@H]3C=C(C)C[C@]21C(C=CC(=O)N1)=C1C3 YYWGABLTRMRUIT-HWWQOWPSSA-N 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- UTSOXZIZVGUTCF-UHFFFAOYSA-N hydrate;hydroiodide Chemical compound O.I UTSOXZIZVGUTCF-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
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- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- DLINORNFHVEIFE-UHFFFAOYSA-N hydrogen peroxide;zinc Chemical compound [Zn].OO DLINORNFHVEIFE-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- GQZXNSPRSGFJLY-UHFFFAOYSA-N hydroxyphosphanone Chemical compound OP=O GQZXNSPRSGFJLY-UHFFFAOYSA-N 0.000 description 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Chemical compound Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 description 1
- 229940005631 hypophosphite ion Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- 229940006461 iodide ion Drugs 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
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- 150000002576 ketones Chemical class 0.000 description 1
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- 150000002596 lactones Chemical class 0.000 description 1
- 238000010330 laser marking Methods 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- BFZPBUKRYWOWDV-UHFFFAOYSA-N lithium;oxido(oxo)cobalt Chemical compound [Li+].[O-][Co]=O BFZPBUKRYWOWDV-UHFFFAOYSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
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- 239000006224 matting agent Substances 0.000 description 1
- ZQKXQUJXLSSJCH-UHFFFAOYSA-N melamine cyanurate Chemical compound NC1=NC(N)=NC(N)=N1.O=C1NC(=O)NC(=O)N1 ZQKXQUJXLSSJCH-UHFFFAOYSA-N 0.000 description 1
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- 150000001247 metal acetylides Chemical class 0.000 description 1
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- 125000005394 methallyl group Chemical group 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- MAQCMFOLVVSLLK-UHFFFAOYSA-N methyl 4-(bromomethyl)pyridine-2-carboxylate Chemical compound COC(=O)C1=CC(CBr)=CC=N1 MAQCMFOLVVSLLK-UHFFFAOYSA-N 0.000 description 1
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- NYCZNDFWFCCTPA-UHFFFAOYSA-N methyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC)OC1=CC=CC=C1 NYCZNDFWFCCTPA-UHFFFAOYSA-N 0.000 description 1
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- VXYADVIJALMOEQ-UHFFFAOYSA-K tris(lactato)aluminium Chemical compound CC(O)C(=O)O[Al](OC(=O)C(C)O)OC(=O)C(C)O VXYADVIJALMOEQ-UHFFFAOYSA-K 0.000 description 1
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- 235000019801 trisodium phosphate Nutrition 0.000 description 1
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
- WGIWBXUNRXCYRA-UHFFFAOYSA-H trizinc;2-hydroxypropane-1,2,3-tricarboxylate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O WGIWBXUNRXCYRA-UHFFFAOYSA-H 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- 239000011667 zinc carbonate Substances 0.000 description 1
- 235000004416 zinc carbonate Nutrition 0.000 description 1
- 229910000010 zinc carbonate Inorganic materials 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011746 zinc citrate Substances 0.000 description 1
- 235000006076 zinc citrate Nutrition 0.000 description 1
- 229940068475 zinc citrate Drugs 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical class [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- 229910021511 zinc hydroxide Inorganic materials 0.000 description 1
- 229940007718 zinc hydroxide Drugs 0.000 description 1
- 239000011576 zinc lactate Substances 0.000 description 1
- 235000000193 zinc lactate Nutrition 0.000 description 1
- 229940050168 zinc lactate Drugs 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
- 229940048462 zinc phosphide Drugs 0.000 description 1
- OMSYGYSPFZQFFP-UHFFFAOYSA-J zinc pyrophosphate Chemical compound [Zn+2].[Zn+2].[O-]P([O-])(=O)OP([O-])([O-])=O OMSYGYSPFZQFFP-UHFFFAOYSA-J 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Substances [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- ZMLPZCGHASSGEA-UHFFFAOYSA-M zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F ZMLPZCGHASSGEA-UHFFFAOYSA-M 0.000 description 1
- 229940006174 zinc valerate Drugs 0.000 description 1
- VRGNUPCISFMPEM-ZVGUSBNCSA-L zinc;(2r,3r)-2,3-dihydroxybutanedioate Chemical compound [Zn+2].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O VRGNUPCISFMPEM-ZVGUSBNCSA-L 0.000 description 1
- LPEBYPDZMWMCLZ-CVBJKYQLSA-L zinc;(z)-octadec-9-enoate Chemical compound [Zn+2].CCCCCCCC\C=C/CCCCCCCC([O-])=O.CCCCCCCC\C=C/CCCCCCCC([O-])=O LPEBYPDZMWMCLZ-CVBJKYQLSA-L 0.000 description 1
- VCQWRGCXUWPSGY-UHFFFAOYSA-L zinc;2,2,2-trifluoroacetate Chemical compound [Zn+2].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F VCQWRGCXUWPSGY-UHFFFAOYSA-L 0.000 description 1
- ZNVKGUVDRSSWHV-UHFFFAOYSA-L zinc;4-hydroxybenzenesulfonate Chemical compound [Zn+2].OC1=CC=C(S([O-])(=O)=O)C=C1.OC1=CC=C(S([O-])(=O)=O)C=C1 ZNVKGUVDRSSWHV-UHFFFAOYSA-L 0.000 description 1
- AGFGXVAAIXIOFZ-UHFFFAOYSA-L zinc;butanedioate Chemical compound [Zn+2].[O-]C(=O)CCC([O-])=O AGFGXVAAIXIOFZ-UHFFFAOYSA-L 0.000 description 1
- WDHVIZKSFZNHJB-UHFFFAOYSA-L zinc;butanoate Chemical compound [Zn+2].CCCC([O-])=O.CCCC([O-])=O WDHVIZKSFZNHJB-UHFFFAOYSA-L 0.000 description 1
- MQWLIFWNJWLDCI-UHFFFAOYSA-L zinc;carbonate;hydrate Chemical compound O.[Zn+2].[O-]C([O-])=O MQWLIFWNJWLDCI-UHFFFAOYSA-L 0.000 description 1
- JQOAZIZLIIOXEW-UHFFFAOYSA-N zinc;chromium(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Cr+3].[Cr+3].[Zn+2] JQOAZIZLIIOXEW-UHFFFAOYSA-N 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
- WOAQZEHJXZOJCS-UHFFFAOYSA-N zinc;diisocyanate Chemical compound [Zn+2].[N-]=C=O.[N-]=C=O WOAQZEHJXZOJCS-UHFFFAOYSA-N 0.000 description 1
- HHIMNFJHTNVXBJ-UHFFFAOYSA-L zinc;dinitrite Chemical compound [Zn+2].[O-]N=O.[O-]N=O HHIMNFJHTNVXBJ-UHFFFAOYSA-L 0.000 description 1
- RXBXBWBHKPGHIB-UHFFFAOYSA-L zinc;diperchlorate Chemical compound [Zn+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O RXBXBWBHKPGHIB-UHFFFAOYSA-L 0.000 description 1
- YMTQMTSQMKJKPX-UHFFFAOYSA-L zinc;diphenoxide Chemical compound [Zn+2].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 YMTQMTSQMKJKPX-UHFFFAOYSA-L 0.000 description 1
- MLVWCBYTEFCFSG-UHFFFAOYSA-L zinc;dithiocyanate Chemical compound [Zn+2].[S-]C#N.[S-]C#N MLVWCBYTEFCFSG-UHFFFAOYSA-L 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
- ZPEJZWGMHAKWNL-UHFFFAOYSA-L zinc;oxalate Chemical compound [Zn+2].[O-]C(=O)C([O-])=O ZPEJZWGMHAKWNL-UHFFFAOYSA-L 0.000 description 1
- RNWHGQJWIACOKP-UHFFFAOYSA-N zinc;oxygen(2-) Chemical class [O-2].[Zn+2] RNWHGQJWIACOKP-UHFFFAOYSA-N 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- BUDAIZWUWHWZPQ-UHFFFAOYSA-L zinc;pentanoate Chemical compound [Zn+2].CCCCC([O-])=O.CCCCC([O-])=O BUDAIZWUWHWZPQ-UHFFFAOYSA-L 0.000 description 1
- XKMZOFXGLBYJLS-UHFFFAOYSA-L zinc;prop-2-enoate Chemical compound [Zn+2].[O-]C(=O)C=C.[O-]C(=O)C=C XKMZOFXGLBYJLS-UHFFFAOYSA-L 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- 229910052845 zircon Inorganic materials 0.000 description 1
- 150000003754 zirconium Chemical class 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
- GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
Classifications
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Abstract
a)ホスフィン酸源(I)を触媒Aの存在下にオレフィン(IV)と反応させて、アルキル亜ホスホン酸、それの塩またはエステル(II)とし、
b)こうして生じたアルキル亜ホスホン酸、それの塩またはエステル(II)を、触媒Bの存在下にアセチレン系化合物(V)と反応させて、単官能化ジアルキルホスフィン酸誘導体(VI)とし、及び
c)こうして生じた単官能化ジアルキルホスフィン酸誘導体(VI)を触媒Cの存在下に一酸化炭素と反応させて、次式
【化1】
のモノカルボキシ官能化ジアルキルホスフィン酸誘導体(III)とし、ここで、R1、R2、R3、R4、R5、R6は、同一かもしくは異なり、そして互いに独立して、中でも、H、C1−C18−アルキル、C6−C18−アリール、C6−C18−アラルキル、C6−C18−アルキルアリールを意味し、X及びYは、同一かまたは異なり、そして互いに独立して、H、C1−C18−アルキル、C6−C18−アリール、C6−C18−アラルキル、C6−C18−アルキルアリール、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K及び/またはプロトン化された窒素塩基を表し、そして触媒A、B、C及びDは、遷移金属、及び/または遷移金属化合物、及び/または遷移金属及び/または遷移金属化合物と少なくとも一つの配位子から構成される触媒系であることを特徴とする、前記方法に関する。
Description
a)次式
b)こうして生じたアルキル亜ホスホン酸、それの塩またはエステル(II)を、次式
c)こうして生じた単官能化ジアルキルホスフィン酸誘導体(VI)を、一酸化炭素と触媒Cの存在下に、あるいは水またはアルコールM−OH及び/もしくはM’−OHと反応させて、次式
アリルニッケル(II)塩化物ダイマー、アンモニウムニッケル(II)硫酸塩、ビス(1,5−シクロオクタジエン)ニッケル(0)、ビス(トリフェニルホスフィン)ジカルボニルニッケル(0)、テトラキス(トリフェニルホスフィン)ニッケル(0)、テトラキス(トリフェニルホスフィット)ニッケル(0)、カリウムヘキサフルオロニッケル酸塩(IV)、カリウムテトラシアノニッケル酸塩(II)、カリウムニッケル(IV)パラ過ヨウ素酸塩、ジリチウムテトラブロモニッケル酸塩(II)、カリウムテトラシアノニッケル酸塩(II);
白金(IV)塩化物、−酸化物、−硫化物、カリウム−、ナトリウム−、アンモニウムヘキサクロロ白金酸塩(IV)、カリウム−、アンモニウムテトラクロロ白金酸塩(II)、カリウムテトラシアノ白金酸塩(II)、トリメチル(メチルシクロペンタジエニル)白金(IV)、シス−ジアンミンテトラクロロ白金(IV)、カリウムトリクロロ(エチレン)白金酸塩(II)、ナトリウムヘキサヒドロキシ白金酸塩(IV)、テトラアミン白金(II)テトラクロロ白金酸塩(II)、テトラブチルアンモニウムヘキサクロロ白金酸塩(IV)、エチレンビス(トリフェニルホスフィン)白金(0)、白金(0)−1,3−ジビニル−1,1,3,3−テトラメチル−ジシロキサン、白金(0)−2,4,6,8−テトラメチル−2,4,6,8−テトラビニルシクロテトラシロキサン、テトラキス−(トリフェニルホスフィン)白金(0)、白金オクタエチルポルフィリン、クロロ白金酸、カルボ白金;
クロロビス(エチレン)ロジウムダイマー、ヘキサロジウムヘキサデカカルボニル、クロロ(1,5−シクロオクタジエン)ロジウムダイマー、クロロ(ノルボマジエン)−ロジウムダイマー、クロロ(1,5−ヘキサジエン)ロジウムダイマーである。
式中、R8基は、互いに独立して、水素、直鎖状、分枝状もしくは環状C1−C20−アルキル、C1−C20−アルキルアリール、C2−C20−アルケニル、C2−C20−アルキニル、C1−C20−カルボキシレート、C1−C20−アルコキシ、C1−C20−アルケニルオキシ、C1−C20−アルキニルオキシ、C2−C20−アルコキシ−カルボニル、C1−C20−アルキルチオ、C1−C20−アルキルスルホニル、C1−C20−アルキルスルフィニル、シリル及び/またはそれらの誘導体及び/または少なくとも一つのR9によって置換されたフェニル−または少なくとも一つのR9によって置換されたナフチルを表す。R9は、互いに独立して、水素、フッ素、塩素、臭素、ヨウ素、NH2、ニトロ、ヒドロキシ、シアノ、ホルミル、直鎖状、分枝状もしくは環状C1−C20−アルキル、C1−C20−アルコキシ、HN(C1−C20−アルキル)、N(C1−C20−アルキル)2、−CO2−(C1−C20−アルキル)、−CON(C1−C20−アルキル)2、−OCO(C1−C20−アルキル)、NHCO(C1−C20−アルキル)、C1−C20−アシル、−SO3M、−SO2N(R10)M、−CO2M、−PO3M2、−AsO3M2、−SiO2M、−C(CF3)2OM(M=H、Li、NaまたはK)を表し、ここでR10は、水素、フッ素、塩素、臭素、ヨウ素、直鎖状、分枝状もしくは環状C1−C20−アルキル、C2−C20−アルケニル、C2−C20−アルキニル、C1−C20−カルボキシレート、C1−C20−アルコキシ、C1−C20−アルケニルオキシ、C1−C20−アルキニルオキシ、C2−C20−アルコキシカルボニル、C1−C20−アルキルチオ、C1−C20−アルキルスルホニル、C1−C20−アルキルスルフィニル、シリル及び/またはこれらの誘導体、アリール、C1−C20−アリールアルキル、C1−C20−アルキルアリール、フェニル及び/またはビフェニルを意味する。好ましくは、R8基の全てが同一である。
前記式中、M’’は互いに独立してN、P、AsまたはSbを表す。好ましくは、両方のM’’は同一であり、特に好ましくはM’’はリン原子を表す。
コバルト、コバルト(I)−及び/またはコバルト(II)−及び/またはコバルト(III)−及び/またはコバルト(IV)塩化物、−臭化物、−ヨウ化物、−フッ化物、−酸化物、−水酸化物、−シアン化物、−硫化物、−テルル化物、−ホウ化物、−硫酸塩、−硝酸塩、−プロピオン酸塩、−酢酸塩、−安息香酸塩、−アセチルアセトネート、−ベンゾイルアセトネート、−ヘキサフルオロアセチル−アセトネート、−2−エチルヘキサン酸塩、−炭酸塩、−メトキシド、−酒石酸塩、−シクロヘキサン酪酸塩、−D−グルコン酸塩、−ギ酸塩、−モリブデン酸塩、−フタロシアニン、−2,3−ナフタロシアニン、−シュウ酸塩、−過塩素酸塩、−リン酸塩、−セレン化物、−ピロリン酸塩、−シクロペンタジエニル、−メチルシクロペンタジエニル、−エチルシクロペンタジエニル、−ペンタメチルシクロペンタジエニル、−リン化物、−ナフテン酸塩、−2−メトキシエトキシド、−トリス(2,2,6,6−テトラメチル−3,5−ヘプタン二酸塩、−2,2,6,6−テトラメチル−3,5−ヘプタン二酸塩、−ヘキサフルオロ−2,4−ペンタジエン酸塩、−イソプロポキシド、−ステアリン酸、−スルファミン酸、−クエン酸塩、−シクロヘキサン酪酸塩、N,N’−ジイソプロピルアセトアミジネート、−チオフェン−2−カルボン酸塩、−チオシアン酸塩、−チオフェノレート、−トリフルオロメタンスルホン酸塩、−ヘキサフルオロリン酸塩、−テトラフルオロホウ酸塩、−トリフルオロメタンスルホン酸塩、−1−ブタンチオール酸塩、−チオ硫酸塩、−トリフルオロ酢酸塩、−過塩素酸塩、−2,3,7,8,12,13,17,18−オクタエチル−21H,23H−ポルフィン、−5,10,15,20−テトラフェニル−21H,23H−ポルフィン、−5,10,15,20−テトラキス−(ペンタフルオロフェニル)−21H,23H−ポルフィン及びそれの1,4−ビス(ジフェニルホスフィン)ブタン−、1,3−ビス(ジフェニルホスフィノ)プロパン−、2−(2’−ジ−tert−ブチルホスフィン)ビフェニル、ジノルボルニル−ホスフィン−、ビス(ジフェニルホスフィノ)ブタン−、(N−スクシンイミジル)ビス(トリフェニルホスフィン)−、ジメチルフェニルホスフィン−、メチルジフェニルホスフィン−、1,5−シクロオクタジエン−、N,N,N’,N’−テトラメチルエチレンジアミン−、トリフェニルホスフィン−、トリ−o−トリルホスフィン−、トリシクロヘキシル−ホスフィン−、トリエチルホスフィン−、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル−、1,3−ビス(2,6−ジイソプロピルフェニル)イミダゾール−2−イリデン−、1,3−ビス(メシチル)イミダゾール−2−イリデン−、1,1’−ビス(ジフェニルホスフィノ)フェロセン−、1,2−ビス(ジフェニルホスフィノ)エタン−、2,2’−ジピリジン−、トリメチルホスフィット−、エチレンジアミン−、カルボニル−、アミン−錯体、コバルト−アルミニウム酸化物、サマリウム−コバルト、ビスマス−コバルト−亜鉛酸化物、ニッケル−コバルト酸化物、Raney(登録商標)−コバルト、アルミニウム−ニッケル−コバルト、コバルト−チタン酸化物、コバルト−鉄酸化物、リチウム−コバルト(III)酸化物、アルミニウム−コバルトイソプロポキシド、カリウムヘキサシアノコバルテート(II)フェレート(II)、カリウムヘキサシアノコバルテート(II)、コバルトカルボニル、オクタカルボニルジコバルト、ドデカカルボニルテトラコバルト。
ジフェニル−p−、−m−もしくは−o−トリルホスフィット、ジ−p−、−m−もしくは−o−トリルフェニルホスフィット、m−トリル−o−トリル−p−トリルホスフィット、o−トリル−p−もしくは−m−トリルフェニルホスフィット、ジ−p−トリル−m−もしくは−o−トリル−ホスフィット、ジ−m−トリル−p−もしくは−o−トリルホスフィット、トリ−m−、−p−もしくは−o−トリルホスフィット、ジ−o−トリル−m−もしくは−p−トリルホスフィット; トリス(2−エチルヘキシル)−、トリベンジル−、トリラウリル−、トリ−n−ブチル−、トリエチル−、トリ−ネオ−ペンチル−、トリ−i−プロピル−、トリス(2,4−ジ−t−ブチルフェニル)−、トリス(2,4−ジ−tert−ブチルフェニル)−、ジエチルトリメチル−シリル−、ジイソデシルフェニル−、ジメチルトリメチルシリル−、トリイソデシル−、トリス(tert−ブチルジメチルシリル)−、トリス(2−クロロエチル−、トリス(1,1,1,3,3,3−ヘキサフルオロ−2−プロピル)−、トリス(ノニル−フェニル)−、トリス(2,2,2−トリフルオロエチル)−、トリス(トリメチルシリル)−、2,2−ジメチルトリメチレン−フェニル−、トリオクタデシル−、トリメチロールプロパン−、ベンジルジエチル−、(R)−ビナフチルイソブチル−、(R)−ビナフチルシクロペンチル−、(R)−ビナフチルイソプロピル−、トリス(2−トリル)−、トリス(ノニルフェニル)−及びメチルジフェニルホスフィット; (11aR)−(+)−10,11,12,13−テトラヒドロ−ジインデノ[7,1−de:1’,7’−fg][1,3,2]ジオキサアホスホシン(dioxaaphosphocin)−5−フェノキシ、4−エチル−2,6,7−トリオキサ−1−ホスファビシクロ[2.2.2]−オクタン、(11bR,11’bR)−4,4’−(9,9−ジメチル−9H−キサンテン−4,5−ジイル)ビス−ジナフト[2,1−d:1’,2’−f][1,3,2]ジオキサホスフェピン、(11bR,11’bR)−4,4’−(オキシジ−2,1−フェニレン)ビス−ジナフト[2,1−d:,1’,2’−f][1,3,2]ジオキサホスフェピン、(11bS,11’bS)−4,4’−(9,9−ジメチル−9H−キサンテン−4,5−ジイル)ビス−ジナフト[2,1−d:1’,2’−f][1,3,2]ジオキサホスフェピン、(11bS,11’bS)−4,4’−(オキシジ−2,1−フェニレン)ビス−ジナフト[2,1−d:1’,2’−f][1,3,2]ジオキサホスフェピン、1,1’ビス[(11bR)−及び1,1’ビス[(11bS)−ジナフト[2,1−d:1’,2’−f][1,3,2]ジオキサホスフェピン−4−イル]フェロセン; ジメチルフェニル−、ジエチルメチルフェニル−及びジエチルフェニル−及びジイソプロピルフェニルホスホニット; ジメチルフェニル−、ジイソプロピルフェニル−、エチルジフェニル−及びメチルジフェニルホスホニット。
1,2−ビス(ジアダマンチルホスフィノメチル)ベンゼン、1,2−ビス(ジ−3,5−ジメチルアダマンチル−ホスフィノメチル)ベンゼン、1,2−ビス(ジ−5−tert−ブチルアダマンチルホスフィノ−メチル)ベンゼン、1,2−ビス(1−アダマンチルtert−ブチル−ホスフィノメチル)ベンゼン、1−(ジ−tertブチルホスフィノ−メチル)−2−(ホスファアダマンチルホスフィノメチル)ベンゼン、1−(ジアダマンチルホスフィノ−メチル)−2−(ホスファアダマンチルホスフィノメチル)ベンゼン、1−(tert−ブチルアダマンチル)−2−(ジアダマンチル)−(ホスフィノメチル)ベンゼン、1,2−ビス(ジ−tert−ブチルホスフィノメチル)−フェロセン、1,2−ビス(ジ−tertブチルホスフィノメチル)フェロセン、1,2−ビス(ジシクロヘキシルホスフィノメチル)−フェロセン、1,2−ビス(ジ−イソブチルホスフィノ−メチル)フェロセン、1,2−ビス(ジシクロペンチル−ホスフィノ−メチル)フェロセン、1,2−ビス−(ジエチルホスフィノメチル)−フェロセン、1,2−ビス(ジイソプロピルホスフィノメチル)フェロセン、1,2−ビス(ジメチルホスフィノメチル)フェロセン、9,9−ジメチル−4,5−ビス(ジフェノキシホスフィン)キサンテン、9,9−ジメチル−4,5−ビス(ジ−p−メチルフェノキシホスフィン)−キサンテン、9,9−ジメチル−4,5−ビス(ジ−o−メチルフェノキシホスフィン)キサンテン、9,9−ジメチル−4,5−ビス(ジ−1,3,5−トリメチルフェノキシ−ホスフィン)キサンテン、9,9−ジメチル−4,5−ビス(ジフェノキシホスフィン)−2,7−ジ−tert.−ブチル−キサンテン、9,9−ジメチル−4,5−ビス(ジ−o−メチルフェノキシホスフィン)−2,7−ジ−tert.−ブチル−キサンテン、9,9−ジメチル−4,5−ビス(ジ−p−メチルフェノキシホスフィン)−2,7−ジ−tert.−ブチル−キサンテン、9,9−ジメチル−4,5−ビス(ジ−1,3,5−トリメチルフェノキシホスフィン)−2,7−ジ−tert.−ブチル−キサンテン、1,1’−ビス(ジフェノキシホスフィン)フェロセン、1,1’−ビス(ジ−o−メチルフェノキシ−)フェロセン、1,1’−ビス(ジ−p−メチルフェノキシホスフィン)フェロセン、1,1’−ビス(ジ−1,3,5−トリメチル−フェノキシホスフィン)フェロセン、2,2’−ビス(ジフェノキシホスフィン)−1,1’−ビナフチル、2,2’−ビス(ジ−o−メチルフェノキシホスフィン)−1,1’−ビナフチル、2,2’−ビス(ジ−p−メチルフェノキシ−ホスフィン)−1,1’−ビナフチル、2,2’−ビス(ジ−1,3,5−トリメチルフェノキシホスフィン)−1,1’−ビナフチル、(オキシジ−2,1−フェニレン)ビス(ジフェノキシホスフィン)、(オキシジ−2,1−フェニレン)ビス(ジ−o−メチルフェノキシホスフィン)、(オキシジ−2,1−フェニレン)ビス(ジ−p−メチルフェノキシホスフィン)、(オキシジ−2,1−フェニレン)ビス−(ジ−1,3,5−トリメチルフェノキシホスフィン)、2,2’−ビス(ジフェノキシ−ホスフィン)−1,1’−ビフェニル、2,2’−ビス(ジ−o−メチルフェノキシホスフィン)−1,1’−ビフェニル、2,2’−ビス(ジ−p−メチルフェノキシ−ホスフィン)−1,1’−ビフェニル、2,2’−ビス(ジ−1,3,5−トリメチルフェノキシホスフィン)−1,1’−ビフェニル、1,2−ビス(ジ−(1,3,5,7−テトラメチル−6,9,10−トリオキサ−2−ホスファアダマンチルメチル)フェロセン、1−(tert−ブトキシカルボニル)−(2S,4S)−2−[(ジフェニルホスフィノ)メチル]−4−(ジベンゾホスホリル)−ピロリジン、1−(tert−ブトキシ−カルボニル)−(2S,4S)−2−[(ジベンゾホスホリル)メチル]−4−(ジフェニル−ホスフィノ)ピロリジン、1−(tert−ブトキシカルボニル)−(2S,4S)−4−(ジベンゾホスホリル)−2−[(ジベンゾホスホリル)メチル]−ピロリジン、ビナホス(BINAPHOS)、ケリフィット(Kelliphit)、キラフィット(Chiraphit)、ビス−3,4−ジアゾホスホラン、ビス(ホスホラン)配位子、例えばビス(2,5−トランスジアルキルホスホラン)、ビス(2,4−trans−ジアルキルホスフェタン)、1,2−ビス(フェノキシホスフィン)エタン、1,2−ビス(3−メチル−フェノキシ−ホスフィン)エタン、1,2−ビス(2−メチルフェノキシホスフィン)エタン、1,2−ビス(1−メチル−フェノキシホスフィン)エタン、1,2−ビス(1,3,5−トリメチルフェノキシホスフィン)エタン、1,3−ビス(フェノキシホスフィン)プロパン、1,3−ビス(3−メチルフェノキシホスフィン)プロパン、1,3−ビス(2−メチル−フェノキシホスフィン)プロパン、1,3−ビス(1−メチルフェノキシホスフィン)プロパン、1,3−ビス(1,3,5−トリメチルフェノキシホスフィン)プロパン,1,4−ビス(フェノキシホスフィン)ブタン、1,4−ビス(3−メチル−フェノキシホスフィン)ブタン、1,4−ビス(2−メチルフェノキシホスフィン)ブタン、1,4−ビス(1−メチル−フェノキシホスフィン)ブタン、1,4−ビス(1,3,5−トリメチルフェノキシホスフィン)ブタン。
金、コロイド金、ルテニウム、活性炭上に、炭素上に、アルミナ上に担持させたルテニウム、白金−パラジウム−金合金、金−ニッケル合金、金−ゲルマニウム合金、金−白金合金、金−パラジウム合金、金−ベリリウム合金、白金−ルテニウム合金、パラジウム−ルテニウム合金、金(I)−及び/または金(III)−、ルテニウム(II)−及び/またはルテニウム(III)−及び/またはルテニウム(IV)塩化物、−臭化物、−ヨウ化物、−酸化物、−シアニド、−カリウムシアニド、−ナトリウムシアニド −硫化物、−硫酸塩、−水素化物、−ニトロシル塩化物、−ニトロシル硝酸塩、−バトフェナントロリンジスルホネートナトリウム塩、−チオ硫酸塩、−過塩素酸塩、−シクロペンタジエニル、−エチルシクロペンタジエニル、−ペンタメチルシクロペンタジエニル、−インデニル、−2−メチルアリル、−プロピオン酸塩、−酢酸塩、−アセチルアセトネート、−ヘキサフルオロアセチルアセトネート、−テトラフルオロホウ酸塩、−カリウムチオシアン酸塩、−ナトリウムチオシアン酸塩、−トリフルオロ酢酸塩、−ビス(トリフルオロメタンスルホニル)イミド酸塩、−ヘキサフルオロアンチモン酸塩、−2−ピリジンカルボン酸塩、及びそれらの1,4−ビス(ジフェニルホスフィン)−ブタン−、1,3−ビス(ジフェニルホスフィノ)プロパン−、2−(2’−ジ−tert−ブチルホスフィン)ビフェニル−、アセトニトリル−、ベンゾニトリル−、ジノルボルニルホスフィン−、1,4−ビス(ジフェニルホスフィノ)ブタン−、ジメチルフェニルホスフィン−、メチルジフェニルホスフィン−、トリフェニルホスフィン−、トリ−o−トリルホスフィン−、トリシクロヘキシルホスフィン−、トリブチルホスフィン−、トリ−tert−ブチルホスフィン−、トリメチルホスフィン−、トリエチルホスフィン−、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル−、1,3−ビス(メシチル)イミダゾール−2−イリデン−、1,1’−ビス(ジフェニル−ホスフィノ)フェロセン−、(1,1’−ビフェニル−2−イル)ジ−tert−ブチルホスフィン−、1,3−ビス(2,6−ジイソ−プロピル−フェニル)イミダゾール−2−イリデン−、2−ジシクロヘキシル(2’,4’,6’−トリイソプロピルビフェニル)−ホスフィン−、ジメチルスルフィド−、トリス(2,4−ジ−tert−ブチルフェニル)ホスフィット−、トリス(パラ−トリフルオロメチルフェニル)ホスフィン−、ビス(ジフェニル−ホスフィノ)メタン−、1,2−ビス(ジフェニルホスフィノ)エタン−、N−メチルイミダゾール−、1,10−フェナントロリン−、4,7−ジフェニル−1,10−フェナントロリン−、1,5−シクロオクタジエン−、1,3,5−シクロオクタトリエン−、ナフタレン−、p−サイメン−、3−メチル−2−ブテニリデン−、ベンジリデン−、ピリジン−、2,3,7,8,12,13,17,18−オクタエチル−21H,23H−ポルフィン−、5,10,15,20−テトラフェニル−21H,23H−ポルフィン−、N,N,N’,N’−テトラメチルエチレンジアミン−、トリ−o−トリルホスフィン−、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフチル−、1,1’−ビス(ジフェニル−ホスフィノ)フェロセン−、2,2’−ビピリジン−、(ビシクロ[2.2.1]ヘプタ−2,5−ジエン)−、ビス(ジ−tert−ブチル(4−ジメチルアミノフェニル)ホスフィン)−、2−(ジ−tert−ブチルホスフィノ)エチルアミン−、(2−(ジフェニル−ホスフィノ)エチルアミン−、1,3−ビス(2,4,6−トリメチルフェニル)−2−イミダゾリジニリデン−、1,2−ジ−アミノシクロヘキサン−、ピリジン−、カルボニル−、エチレンジアミン−、アミン−錯体; カリウムジシアノアウラート(I)、ナトリウムテトラクロロアウラート(III)、カリウム金(III)塩化物、ナトリウムアウロチオマレート、トリス(トリフェニルホスフィン金)オキソニウムテトラフルオロホウ酸塩、水素テトラブロモアウレート(III); アンモニウムヘキサクロロルテネート(IV)、カリウムアクアペンタクロロルテネート(III)、(1,5−シクロオクタジエン)−(1,3,5−シクロオクタトリエン)ルテニウム、トリルテニウムドデカカルボニル、グラブス触媒。
難燃性ポリマー成形材料及び難燃性ポリマー成形体の製造、加工及び試験
難燃剤成分を、ポリマーペレット、場合によっては及び添加剤と混合し、そして二軸スクリュー押出機(型Leistritz LSM(登録商標)30/34)で230〜260℃の温度(ガラス繊維強化PBT)または260〜280℃の温度(ガラス繊維強化PA66)で配合する。均一化されたポリマーストランドを引き抜き、水浴中で冷却し、次いでペレット化した。
UL94では、以下の防火クラスが結果として生ずる:
V−0: 10秒より長い後有炎燃焼無し、10回接炎した時の後有炎燃焼時間の合計が50秒以下、燃焼滴下物無し、試料の完全な焼失無し、接炎終了後に30秒を超える試料の後無炎燃焼無し。
V−1: 接炎終了後に30秒を超える後有炎燃焼無し、10回接炎した時に後有炎燃焼時間の合計が250秒以下、接炎終了後に60秒を超える試料の後無炎燃焼無し、他はV−0と同じ規準。
V−2: 燃焼滴下物による綿の点火、他はV−1と同じ規準。
クラス分け不能(nkl): 防火クラスV−2を満たさない。
LOI 23 可燃性
LOI 24〜28 限られた可燃性
LOI 29〜35 難燃性
LOI >36 格別に難燃性
使用した化学品及び略称
VE水 完全に脱塩した水
AIBN アゾ−ビス−(イソブチロニトリル)(WAKO Chemicals GmbH製)
WakoV65 2,2’−アゾビス(2,4−ジメチル−バレロニトリル)(WAKO Chemicals GmbH製)
Deloxan(登録商標)THPII 金属捕捉剤(Evonik Industries AG製)
室温で、攪拌機及び強力冷却器を備えた三つ首フラスコ中に188gの水を仕込み、そして攪拌及び窒素導通下に脱気する。次いで、窒素雰囲気下に、0.2mgの硫酸パラジウム(II)及び2.3mgのトリス(3−スルホフェニル)−ホスフィン三ナトリウム塩を加えそして攪拌し、次いで66gの水中の66gのホスフィン酸を加える。この反応溶液を2Lのビュッヒ反応器に移し替え、そして攪拌及び加圧下にエチレンを装入し、そしてこの反応混合物を80℃に加熱する。28gのエチレンが吸収された後、冷却し、そして遊離のエチレンを排出する。この反応混合物からロータリーエバポレーターで溶剤を除去する。残渣を100gのVE水と混合し、そして室温で窒素雰囲気下に攪拌し、次いで濾過し、そして濾液をトルエンで抽出し、その後、ロータリーエバポレーターで溶剤を除去し、そして得られたエチル亜ホスホン酸(92g、理論値の98%)を集める。
例1と同様にして、99gのホスフィン酸、396gのブタノール、42gのエチレン、6.9mgのトリス(ジベンジリデンアセトン)二パラジウム、9.5mgの4,5−ビス(ジフェニルホスフィノ)−9,9−ジメチルキサンテンを反応させ、次いで精製するためにDeloxan(登録商標)THPIIを装入したカラムに通し、その後もう一度n−ブタノールを加える。80〜110℃の反応温度において、生成した水を共沸蒸留によって除去する。生成物を低められた圧力下に蒸留によって精製する。収量: 189g(理論値の84%)のエチル亜ホスホン酸ブチルエステル。
例1と同様にして、198gのホスフィン酸、198gの水、84gのエチレン、6.1mgの硫酸パラジウム(II)、25.8mgの9,9−ジメチル−4,5−ビス(ジフェニルホスフィノ)−2,7−スルホナト−キサンテン二ナトリウム塩を反応させ、次いで精製するために、Deloxan(登録商標)THPIIを装入したカラムに通し、その後n−ブタノールを加える。80〜110℃の反応温度において、生成した水を共沸蒸留によって除去する。生成物を低められた圧力下に蒸留によって精製する。こうして374g(理論値の83%)のエチル亜ホスホン酸ブチルエステルが得られる。
ガス導入管、温度計、強力攪拌機、及びガス焼却付きの還流冷却器を備えた500ml五つ首フラスコ中に、94g(1モル)のエチル亜ホスホン酸(例1に記載のように製造したもの)を仕込む。室温下に、エチレンオキシドを導入する。冷却しながら、70℃の反応温度を調節し、そして80℃で更に1時間、後反応させる。エチレンオキシド吸収量は65.7gに達する。生成物の酸価は1mgKOH/g未満である。129g(理論値の94%)(エチル亜ホスホン酸−2−ヒドロキシエチルエステル)が無色透明の生成物として得られる。
室温下に、攪拌機及び強力冷却器を備えた三首フラスコ中に400gのTHFを仕込み、そして攪拌及び窒素の導通下に脱気する。次いで、窒素雰囲気下に、1.35g(6ミリモル)の酢酸パラジウム及び4.72g(18ミリモル)のトリフェニルホスフィンを加えそして攪拌し、次いで30g(0.2モル)のエチル亜ホスホン酸ブチルエステル(例2に記載ように製造したもの)及び1.96g(9ミリモル)のジフェニルホスフィン酸を加え、そしてこの反応混合物を80℃に加熱し、そしてアセチレンを、5L/hの体積流量で反応溶液中に通す。5時間の反応時間後、アセチレンを窒素を用いて装置から追い出す。精製するために、反応溶液を、Deloxan(登録商標)THPIIを装入したカラムに通し、そしてTHFを真空下に除去する。生成物を低められた圧力下に蒸留することによって精製する。32.7g(理論値の93%)のエチルビニルホスフィン酸ブチルエステルが無色の油状物として得られる。
室温下に、攪拌機及び強力冷却器を備えた三首フラスコ中に400gの酢酸を仕込み、そして攪拌及び窒素導通下に脱気する。次いで、窒素雰囲気下に、1.35g(6ミリモル)の酢酸パラジウム及び3.47g(6ミリモル)のキサントホス(Xantphos)を加えそして攪拌し、次いで19g(0.2モル)のエチル亜ホスホン酸(例1に記載のように製造したもの)を加え、そしてこの反応混合物を80℃に加熱し、そしてアセチレンを、5L/hの体積流量で反応溶液中に導通する。5時間の反応時間の後、アセチレンを、窒素を用いて装置から追い出す。精製するために、反応溶液を、Deloxan(登録商標)THP IIを装入したカラムに通し、そして酢酸を真空下に除去する。生成物(エチルビニルホスフィン酸)をクロマトグラフィにより精製する。20.9g(理論値の87%)のエチルビニルホスフィン酸が無色の油状物として得られる。
室温下に、攪拌機及び強力冷却器を備えた三首フラスコ中に400gのトルエンを仕込み、そして攪拌及び窒素導通下に脱気する。窒素雰囲気下に、5.55g(6ミリモル)のRhCl(PPh3)3を加えそして攪拌し、次いで30g(0.2モル)のエチル亜ホスホン酸ブチルエステル(例3に記載のように製造したもの)及び20.4g(0.2モル)のフェニル−アセチレンを加え、そしてこの反応混合物を80℃に加熱する。5時間の反応時間の後、反応溶液を、Deloxan(登録商標)THPIIを装入したカラムに通し、そしてトルエンを真空下に除去する。37.6g(理論値の96%)のエチル−(1−フェニル−ビニル)ホスフィン酸ブチルエステルが無色の油状物として得られる。
室温下に、攪拌機及び強力冷却器を備えた三首フラスコ中に400gのTHFを仕込み、そして攪拌及び窒素導通下に脱気する。次いで、窒素雰囲気下に、2.75g(10ミリモル)のビス(シクロオクタジエン)ニッケル(0)及び8g(40ミリモル)のメチルジフェニルホスフィンを加えそして攪拌し、次いで30g(0.2モル)のエチル亜ホスホン酸ブチルエステル(例2に記載のように製造したもの)を加え、そしてこの際、室温で、アセチレンを5L/hの体積流量で反応溶液中に導通する。5時間の反応時間の後、アセチレンを、窒素を用いて装置から追い出す。精製するために、反応溶液を、Deloxan(登録商標)THPIIを装入したカラム中に通し、そしてブタノールを真空中で除去する。33.4g(理論値の95%)のエチルビニルホスフィン酸ブチルエステルが無色の油状物として得られる。
360g(3モル)の得られたエチルビニルホスフィン酸(例6に記載のように製造したもの)を85℃で400mlのトルエン中に溶解し、そして888g(12モル)のブタノールと混合する。約100℃の反応温度で、生成水を共沸蒸留によって除去する。生成物であるエチルビニルホスフィン酸ブチルエステルを低められた圧力下に蒸留して精製する。
360g(3.0モル)のエチルビニルホスフィン酸(例6に記載のように製造したもの)を80℃で400mlのトルエン中に溶解し、そして315g(3.5モル)の1,4−ブタンジオールと混合し、そして水分離器付きの蒸留装置中で、約100℃で4時間の間エステル化する。エステル下の終了後、トルエンを真空下に分離する。518g(理論値の90%)のエチルビニルホスフィン酸−4−ヒドロキシブチルエステルが無色の油状物として得られる。
360g(3.0モル)のエチルビニルホスフィン酸(例6に記載のように製造したもの)を85℃で400mlのトルエン中に溶解し、そして248g(4モル)のエチレングリコールと混合し、そして水分離器付きの蒸留装置中で約100℃で4時間の間エステル化する。エステル化の終了後、トルエン及び過剰のエチルグリコールを真空下に分離する。462g(理論値の94%)のエチルビニルホスフィン酸−2−ヒドロキシエチルエステルが無色の油状物として得られる。
ガラスオートクレーブ中で、2.75g(10ミリモル)のビス(シクロオクタジエン)ニッケル(0)及び8g(40ミリモル)のメチルジフェニルホスフィン、12.0g(0.1モル)のエチルビニルホスフィン酸(例6に記載のように製造したもの)、9.0g(0.15モル)の酢酸、4.5g(0.25モル)の水及び100mlのジクロロメタンを、100℃で、20barの一酸化炭素と反応させた。5時間の反応時間の後、このオートクレーブを解圧した。精製するために、反応溶液を、Deloxan(登録商標)THPIIを装入したカラムに通し、そしてブタノールを真空下に除去し、そして生成物をクロマトグラフィにより精製する。13.4g(理論値の83%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸が無色の油状物として得られる。
ガラスオートクレーブ中で、1.12g(5ミリモル)の酢酸パラジウム、3.95g(10ミリモル)の1,2−ビス[ジ(tert−ブチル)ホスフィノメチル]ベンゼン、17.6g(0.1モル)のエチルビニルホスフィン酸ブチルエステル(例8に記載のように製造したもの)及び100mlのブタノールを、100℃で、20barの一酸化炭素と反応させた。4時間の反応時間後、オートクレーブを解圧した。精製するために、反応溶液を、Deloxan(登録商標)THPIIを装入したカラム中に通し、そしてブタノールを真空下に除去し、そして生成物をクロマトグラフィにより精製する。24.7g(理論値の89%)の3−(エチルブトキシ−ホスフィニル)−プロピオン酸ブチルエステルが無色の油状物として得られる。
ガラスオートクレーブ中で、26mg(0.1ミリモル)のロジウムビスカルボニルアセチルアセトネート、105mg(1.0ミリモル)のトリフェニルホスフィン、25.2g(0.1モル)のエチル−(1−フェニル−ビニル)ホスフィン酸ブチルエステル(例7に記載のように製造したもの)及び100mlのテキサノールを、100℃で、10barの合成ガス混合物CO/H2(1:1)と反応させた。4時間の反応時間の後、オートクレーブを解圧し、溶剤を真空下に除去し、そして生成物をクロマトグラフィにより精製した。25.4g(理論値の91%)のエチル−(1−フェニル−2−ホルミルエチル)−ホスフィン酸ブチルエステルが無色の油状物として得られる。
500mlのアセトン中の28.2g(0.1モル)のエチル−(1−フェニル−2−ホルミルエチル)−ホスフィン酸ブチルエステル(例14に記載のように製造したもの)を、0.11モルのジョーンズ試薬(36.7mlの水及び11.0mlの濃硫酸中の12.7gの三酸化クロム)と0℃で滴下混合した。この反応混合物を、更に、氷冷却下に3×1/2時間、そして室温下に1時間更に攪拌した。12mlのイソプロパノールを添加した後、氷/水上に注ぎ入れる。次いで、易揮発性成分を真空下に留去する。その残留物をテトラヒドロフラン中に取り入れて抽出した。不溶性の塩を濾別した。その濾液の溶剤を真空下に分離し、そしてその残渣をアセトンから再結晶化した。23.2g(理論値の78%)の3−(エチル−ブトキシホスフィニル)−1−フェニル−プロピオン酸が無色の固形物として得られた。
20.6g(0.1モル)のエチル−(2−ホルミルエチル)−ホスフィン酸ブチルエステル(例14に類似して製造したもの)を150mlの水中に溶解し、そして2NのNaOH溶液を用いてpHを9にする。次いで、5%のPt及び1%のBiを含む0.45gの活性炭を加え、この懸濁液を70℃に加温し、そして空気(10L/h)をこの懸濁液中に導通する。この際、懸濁液のpHを、2NのNaOH溶液の添加によりpH=9に維持する。反応の終了後、反応溶液から触媒を濾別し、洗浄しそして水を真空下に留去する。19.5g(理論値の93%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸ナトリウム塩が無色の固形物として得られる。
20.6g(0.1モル)のエチル−(2−ホルミルエチル)−ホスフィン酸ブチルエステル(例14に類似して製造したもの)を150mlの水中に溶解し、そして2NのNaOH溶液を用いてpHを9にする。引き続き、5%のPd及び1%のBiを含む0.25gの活性炭を添加し、この懸濁液を70℃に加温し、そして30%濃度の過酸化水素溶液を、1時間当たり1モル当量の流速で懸濁液中に通す。この際、懸濁液のpHは、2NのNaOH溶液の添加によりpH=9に維持する。反応の終了後に、反応溶液から触媒を濾別し、洗浄しそして水を真空下に留去する。19.3g(理論値の92%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸ナトリウム塩が無色の固形物として得られる。
420g(2モル)の3−(エチルヒドロキシホスフィニル)−プロピオン酸 ナトリウム塩(例16に記載のように製造したもの)の水溶液を、約196gの濃硫酸を用いて酸性にし、そして水を真空下に留去する。その残留物をテトラヒドロフラン中に取り込みそして抽出した。不溶性の塩を濾別した。その濾液の溶剤を真空中で分離し、そしてその残渣をアセトンから再結晶化した。325g(理論値の98%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸が無色の固形物として得られた。
596g(2モル)の3−(エチル−ブトキシホスフィニル)−1−フェニル−プロピオン酸(例15に記載のように製造したもの)を、温度計、還流冷却器、強力攪拌機及び滴下漏斗を備えた1Lの五つ首フラスコ中に仕込む。160℃で、4時間の間に500mlの水を計量添加し、そしてブタノール−水混合物を留去する。固形の残留物をアセトンから再結晶化する。450g(理論値の93%)の3−(エチルヒドロキシホスフィニル)−1−フェニル−プロピオン酸が無色の固形物として得られる。
498g(3モル)の3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)を85℃で400mlのトルエン中に溶解し、そして888g(12モル)のブタノールと混合する。約100℃の反応温度下に、生成した水を共沸蒸留によって除去する。生成物である3−(エチルブトキシホスフィニル)−プロピオン酸ブチルエステルを低められた圧力下に蒸留することによって精製する。
498g(3.0モル)の3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)を80℃で400mlのトルエン中に溶解し、そして594g(6.6モル)の1,4−ブタンジオールと混合し、そして水分離器付きの蒸留装置中で、約100℃で、4時間の間エステル化する。エステル化の終了後、トルエンを真空下に分離する。856g(理論値の92%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸−(4−ヒドロキシブチル)−エステルが無色の油状物として得られる。
276g(2モル)の3−(エチルブトキシホスフィニル)−プロピオン酸ブチルエステル(例20に記載のように製造したもの)に、155g(2.5モル)のエチレングリコール及び0.4gのシュウ酸チタニルカリウムを加え、そして2時間、200℃で攪拌する。ゆっくりと排気することによって、易揮発性成分を留去する。244g(理論値の98%)の3−(エチル−2−ヒドロキシ−エトキシホスフィニル)−プロピオン酸−2−ヒドロキシエチルエステルが得られる。
498g(3.0モル)の得られた3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)を85℃で400mlのトルエン中に溶解し、そして409g(6.6モル)のエチレングリコールと混合し、そして水分離器付きの蒸留装置中で、約100℃で、4時間エステル化する。エステル化の終了後、トルエン及び過剰のエチルグリコールを真空下に分離する。693g(理論値の91%)の3−(エチル−2−ヒドロキシエチルホスフィニル)−プロピオン酸−2−ヒドロキシエチルエステルが無色の油状物として得られる。
996g(6モル)の3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)を860gの水中に溶解し、そして温度計、還流冷却器、強力攪拌機及び滴下漏斗を備えた5Lの五つ首フラスコ中に仕込み、そして約960g(12モル)の50%濃度水酸化ナトリウム溶液を用いて中和する。85℃で、Al2(SO4)3・14H2Oの46%濃度水溶液2583gの混合物を加える。引き続いて、得られた固形物を濾別し、熱水で洗浄し、そして130℃で真空下に乾燥する。収量:無色の塩としての1026g(理論値の94%)の3−(エチルヒドロキシ−ホスフィニル)−プロピオン酸アルミニウム(III)塩。
222g(1モル)の3−(エチルブトキシホスフィニル)−プロピオン酸(例15に類似して製造したもの)及び85gのテトラ酪酸チタンを、500mlのトルエン中で、還流下に40時間加熱する。この際生ずるブタノールを、トルエンの一部と一緒に時々留去する。次いで、生じた溶液から溶剤を除去する。227gの3−(エチル−ブトキシホスフィニル)−プロピオン酸チタン塩が得られる。
25.4gの3−(エチル−2−ヒドロキシエトキシホスフィニル)−プロピオン酸−2−ヒドロキシエチルエステル(例23に記載のように製造したもの)に、290gのテレフタル酸、188gのエチレングリコール、0.34gの酢酸亜鉛を加え、そして2時間200℃に加熱する。次いで、0.29gのリン酸三ナトリウム無水物及び0.14gの酸化アンチモン(III)を加え、280℃に加熱し、その後排気する。得られた溶融物(357g、リン含有率0.9%)から、ISO4589−2準拠の酸素指数(LOI)の測定に、並びに防火試験UL94(Underwriter Laboratories)の測定のために、厚さ1.6mmの試料片を射出する。
こうして製造された試料片は42%O2のLOIを与え、UL94のV−0の防火クラスを満たす。3−(エチル−2−ヒドロキシエトキシ−ホスフィニル)−プロピオン酸−2−ヒドロキシエチルエステルを含まない対応する試料片は、僅か31%O2のLOIを与え、そしてUL94のV−2の防火クラスしか満たさない。それ故、この3−(エチル−2−ヒドロキシエトキシホスフィニル)−プロピオン酸−2−ヒドロキシエチルエステルを含むポリエステル成形体は、明白な難燃性を示す。
14.0gの3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)に、12.9gの1,3−プロピレングリコールを加え、そして160℃で、エステル化の際に生じた水を蒸留する。次いで、378gのジメチルテレフタレート、152gの1,3−プロパンジオール、0.22gのチタン酸テトラブチル及び0.05gの酢酸リチウムを加え、そしてこの混合物を先ず2時間攪拌しながら130〜180℃に加熱し、その後、減圧下に270℃に加熱する。このポリマー(438g)は0.6%のリンを含み、LOIは34である。
14.0gの3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)に、367gのジメチルテレフタレート、170gの1,4−ブタンジオール、0.22gのチタン酸テトラブチル及び0.05gの酢酸リチウムを加え、そしてこの混合物を先ず2時間攪拌しながら130〜180℃に加熱し、その後、減圧下に270℃に加熱する。このポリマー(427g)は0.6%のリンを含み、LOIは34であり、未処理のポリブチレンテレフタレートのLOIは23である。
還流冷却器、攪拌機、温度計及び窒素入口を備えた250mlの五つ首フラスコ中で、0.55モル/100gのエポキシド価を有するビスフェノール−A−ビスグリシドエーテル(Beckopox EP 140、Solutia社)100g及び3−(エチルヒドロキシホスフィニル)−プロピオン酸(例18に記載のように製造したもの)21.6g(0.13モル)を攪拌下に最大150℃に加熱する。30分後に、透明な溶融物が生ずる。150℃で更に1時間攪拌した後、溶融物を冷却しそして細かく砕く。リン含有率が3.3重量%の白色の粉末が118.5g得られる。
攪拌機、水分離器、温度計、還流冷却器及び窒素入口を備えた2Lフラスコ中で、29.4gの無水フタル酸、19.6gの無水マレイン酸、24.8gのプロピレングリコール、18.7gの3−(エチル−2−ヒドロキシエチルホスフィニル)−プロピオン酸−2−ヒドロキシエチルエステル(例23に記載のように製造したもの)、20gのキシレン及び50mgのヒドロキノンを、攪拌及び窒素の導通下に、100℃に加熱する。発熱性の反応が始まったら加熱を止める。反応の終息後、更に約190℃で攪拌する。14gの水が分離された後、キシレンを留去し、そしてポリマー溶融物を冷却する。リン含有率が2.3重量%の白色の粉末91.5gが得られる。
50重量%のポリブチレンテレフタレート、20重量%の3−(エチルヒドロキシ−ホスフィニル)−プロピオン酸アルミニウム(III)塩(例24のように製造されたもの)及び30重量%のガラス繊維からなる混合物を、二軸スクリュー押出機(型Leistritz LSM 30/34)で230〜260℃の温度でコンパウンドしてポリマー成形材料とする。均一化されたポリマーストランドを引き抜き、水浴中で冷却し、次いでペレット化した。乾燥後、この成形材料を射出成形機(型Aarburg Allrounder)で240〜270℃で加工しポリマー成形体とする。V−0のUL−94クラスが達成される。
53重量%のポリアミド6.6、30重量%のガラス繊維、17重量%の3−3−(エチル−ブトキシホスフィニル)−プロピオン酸チタン塩(例25に記載のように製造したもの)からなる混合物を、二軸スクリュー押出機(型Leistritz LSM 30/34)でコンパンドしてポリマー成形材料とする。均一化されたポリマーストランドを引き抜き、水浴中で冷却し、次いでペレット化した。乾燥後、この成形材料を射出成形機(型Aarburg Allrounder)で260〜290℃で加工してポリマー成形体とする。V−0のUL−94クラスが得られる。
Claims (16)
- モノカルボキシ官能化ジアルキルホスフィン酸、−エステル及び−塩の製造方法であって、
a)次式
b)こうして生じたアルキル亜ホスホン酸、それの塩またはエステル(II)を、次式
c)こうして生じた単官能化ジアルキルホスフィン酸誘導体(VI)を、触媒Cの存在下に一酸化炭素と、及び水またはアルコールM−OH及び/またはM’−OHと反応させて、次式
- 段階c)の後に得られるモノカルボキシ官能化ジアルキルホスフィン酸、それの塩またはエステル(III)を、次いで段階d)において、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、Kの金属化合物及び/またはプロトン化された窒素塩基と反応させて、これらの金属及び/または窒素化合物の対応するモノカルボキシ官能化ジアルキルホスフィン酸塩(III)とすることを特徴とする、請求項1または2の方法。
- 段階a)の後に得られるアルキル亜ホスホン酸、それの塩またはエステル(II)、及び/または段階b)の後に得られる単官能化ジアルキルホスフィン酸、それの塩またはエステル(VI)、及び/または段階c)の後に得られる単官能化ジアルキルホスフィン酸、それの塩またはエステル(VII)及び/または(VII’)、及び/またはモノカルボキシ官能化ジアルキルホスフィン酸、それの塩またはエステル(III)、及び/またはそれぞれの生ずる反応溶液を、アルキレンオキシドあるいはアルコールM−OH及び/またはM’−OHでエステル化し、そしてそれぞれ生ずるアルキル亜ホスホン酸エステル(II)、単官能化ジアルキルホスフィン酸エステル(VI)、単官能化ジアルキルホスフィン酸エステル(VII)及び/または(VII’)、及び/またはモノカルボキシ官能化ジアルキルホスフィン酸エステル(III)を、次の反応段階b)、c)またはd)に付すことを特徴とする、請求項1または2の方法。
- C6−C18−アリール、C6−C18−アラルキル及びC6−C18−アルキル−アリール基が、SO3X2、−C(O)CH3、OH、CH2OH、CH3SO3X2、PO3X2、NH2、NO2、OCH3、SH及び/またはOC(O)CH3で置換されていることを特徴とする、請求項1〜4の一つまたはそれ以上の方法。
- R1、R2、R3、R4、R5、R6が、同一かまたは異なり、互いに独立して、H、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert.−ブチル及び/またはフェニルを意味することを特徴とする、請求項1〜5の一つまたはそれ以上の方法。
- X及びYが、同一かまたは異なり、それぞれH、Ca、Mg、Al、Zn、Ti、Fe、Ce、メチル、エチル、n−プロピル、イソプロピル、n−ブチル、イソブチル、tert.−ブチル、フェニル、エチレングリコール、プロピルグリコール、ブチルグリコール、ペンチルグリコール、ヘキシルグリコール、アリル及び/またはグリセリンを意味することを特徴とする、請求項1〜6の一つまたはそれ以上の方法。
- 遷移金属及び/または遷移金属化合物が、第1、第7及び第8亜族からのものであることを特徴とする、請求項1〜7の一つまたはそれ以上の方法。
- 遷移金属及び/または遷移金属化合物が、ロジウム、ニッケル、パラジウム、白金、ルテニウム、コバルト及び/または金であることを特徴とする、請求項1〜8の一つまたはそれ以上の方法。
- 酸化剤が、過マンガン酸カリウム、軟マンガン鉱、三酸化クロム、二クロム酸カリウム、二クロム酸ピリジン、クロロクロム酸ピリジン、コリンズ試薬、ジョーンズ試薬、コレイ−ギルマン−ガネム試薬、(デス−マルチン−)ペルヨージナン、o−ヨードキシ−安息香酸、四酸化ルテニウム、二酸化ルテニウム、過ルテニウム酸テトラ−n−プロピル、三塩化ルテニウム/過ヨウ素酸ナトリウム、二酸化ルテニウム/過ヨウ素酸ナトリウム、塩素、次亜塩素酸塩、及びパーオキソ化合物であることを特徴とする、請求項1〜9の方法。
- アセチレン系化合物(V)が、アセチレン、メチルアセチレン、1−ブチン、1−ヘキシン、2−ヘキシン、1−オクチン、4−オクチン、1−ブチン−4−オール、2−ブチン−1−オール、3−ブチン−1−オール、5−ヘキシン−1−オール、1−オクチン−3−オール、1−ペンチン、フェニルアセチレン、トリメチルシリル−アセチレンであることを特徴とする、請求項1〜10の一つまたはそれ以上の方法。
- 一般式M−OHのアルコールが、C1〜C18の炭素鎖長を有する線状もしくは分枝状で飽和もしくは不飽和の一価有機アルコールであり、一般式M’−OHのアルコールが、C1〜C18の炭素鎖長を有する線状もしくは分枝状で飽和もしくは不飽和の多価有機アルコールであることを特徴とする、請求項1〜11の一つまたはそれ以上の方法。
- 更に別の合成のための中間生成物としての、バインダーとしての、エポキシ樹脂、ポリウレタン及び不飽和ポリエステル樹脂の硬化の際の架橋剤もしくは促進剤としての、ポリマー安定化剤としての、植物保護剤としての、ヒト及び動物のための治療における治療薬または治療薬中の添加剤としての、金属イオン封鎖剤としての、鉱油添加剤としての、腐食保護剤としての、洗濯洗剤及び洗浄剤の用途における及びエレクトロニックの用途における、請求項1〜12の一つまたはそれ以上に従い製造されたモノカルボキシ官能化ジアルキルホスフィン酸、−エステル及び−塩の使用。
- 難燃剤、特に透明塗料及び膨張性発泡塗料のための難燃剤としての、木材及び他のセルロース含有材料のための難燃剤、ポリマー用の反応性及び/または非反応性難燃剤としての、難燃性ポリマー成形材料の製造のための、難燃性ポリマー成形体の製造のための及び/または含浸によるポリエステル及びセルロース単布及び混布の防火処理のための、請求項1〜12の一つまたはそれ以上に従い製造されたモノカルボキシ官能化ジアルキルホスフィン酸、−塩及び−エステルの使用。
- 請求項1〜12の一つまたはそれ以上に従い製造されたモノカルボキシ官能化ジアルキルホスフィン酸、−塩もしくは−エステル0.5〜45重量%、熱可塑性もしくは熱硬化性ポリマーまたはこれらの混合物0.5〜95重量%、添加剤0〜55重量%及びフィラーもしくは強化材0〜55重量%を含み、この際、これらの成分の合計は100重量%である、難燃性熱可塑性もしくは熱硬化性ポリマー成形材料。
- 請求項1〜12の一つまたはそれ以上に従い製造されたモノカルボキシ官能化ジアルキルホスフィン酸、−塩もしくは−エステル0.5〜45重量%、熱可塑性もしくは熱硬化性ポリマーまたはこれらの混合物0.5〜95重量%、添加剤0〜55重量%及びフィラーもしくは強化材0〜55重量%を含み、この際、これらの成分の合計は100重量%である、難燃性熱可塑性もしくは熱硬化性ポリマー成形体、ポリマーフィルム、ポリマー糸及びポリマー繊維。
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011162503A (ja) * | 2010-02-12 | 2011-08-25 | National Institute Of Advanced Industrial Science & Technology | 含パラジウム化合物、その製造方法及びこれを用いる有機化合物の製造法 |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102008055916A1 (de) * | 2008-11-05 | 2010-05-06 | Clariant International Limited | Verfahren zur Herstellung von mono-hydroxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Allylalkoholen und ihre Verwendung |
DE102008055914A1 (de) * | 2008-11-05 | 2010-05-06 | Clariant International Limited | Verfahren zur Herstellung von mono-hydroxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Acroleinen und ihre Verwendung |
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DE102008056339A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von mono-aminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
EP2352740B1 (de) * | 2008-11-07 | 2014-09-24 | Clariant Finance (BVI) Limited | Verfahren zur herstellung von dialkylphosphinsäuren, -estern und -salzen mittels acrylsäurederivaten und ihre verwendung |
DE102008056341A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von monoaminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Acrylnitrilen und ihre Verwendung |
DE102008056342A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von Dialkylphosphinsäuren, -estern und -salzen mittels Acrylnitrilen und ihre Verwendung |
EP2367835B1 (de) * | 2008-11-11 | 2013-12-11 | Clariant Finance (BVI) Limited | Verfahren zur herstellung von mono-allylfunktionalisierten dialkylphosphinsäuren, deren salze und ester mit allylischen verbindungen und ihre verwendung |
DE102008060035A1 (de) * | 2008-12-02 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-hydroxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylester einer Carbonsäure und ihre Verwendung |
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DE102008063668A1 (de) | 2008-12-18 | 2010-07-01 | Clariant International Limited | Verfahren zur Herstellung von Alkylphosponsäuren, -estern und -salzen mittels Oxidation von Alkylphosphonigsäuren und ihre Verwendung |
ES2446666T3 (es) | 2008-12-18 | 2014-03-10 | Clariant Finance (Bvi) Limited | Procedimiento para la preparación de ácidos etilen-dialquil-fosfínicos, o de sus ésteres y sales, mediante acetileno, y su utilización |
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DE102008064012A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Limited | Halogenfreie Addukte von Alkylphosphonigsäurederivaten und diesterbildenden Olefinen, halogenfreie Verfahren zu deren Herstellung und ihre Verwendung |
EP2821426A1 (en) * | 2013-07-03 | 2015-01-07 | Universita' Degli Studi Di Milano | Polymers with complex macromolecular architecture having flame-retardant properties |
EP3560936A1 (en) * | 2018-04-24 | 2019-10-30 | Henkel AG & Co. KGaA | Method for the synthesis of alkenyl-phosphorous compounds |
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CN113181966B (zh) * | 2021-04-25 | 2022-08-30 | 中国科学院兰州化学物理研究所 | 一种用于烯烃氢甲酰化反应的碳负载氮配位钴铁双金属催化剂的制备及应用 |
CN114478627B (zh) * | 2022-02-23 | 2023-06-20 | 湖北大学 | 一种烯丙基化单膦配体及其制备方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56133034A (en) * | 1979-12-12 | 1981-10-17 | Huels Chemische Werke Ag | Hydrogenating treating method for catalyst containing cobalt used for hydrocarboxylation |
JPH02212496A (ja) * | 1989-02-10 | 1990-08-23 | Agency Of Ind Science & Technol | ホスフイニルアルデヒド誘導体の製造法 |
JPH05502447A (ja) * | 1989-11-27 | 1993-04-28 | ヘキスト・アクチェンゲゼルシャフト | 2―ヒドロキシ―エチルホスホン酸ジアルキルエステルの酸化法 |
JP2001518905A (ja) * | 1997-04-15 | 2001-10-16 | ビーエーエスエフ アクチェンゲゼルシャフト | ビニルホスホン酸化合物の製造方法 |
JP2002332290A (ja) * | 2001-03-08 | 2002-11-22 | Japan Science & Technology Corp | アルケニルホスフィン酸エステル類の製造方法 |
JP2004075650A (ja) * | 2002-08-22 | 2004-03-11 | National Institute Of Advanced Industrial & Technology | アルケニルリン化合物及びその製造方法 |
JP2007238617A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシ官能化ジアルキルホスフィン酸塩から組成される混合物、それの使用及び製造方法 |
JP2007238940A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシ官能化ジアルキルホスフィン酸から組成される混合物、それの使用及び製造方法 |
JP2007238616A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシル官能化ジアルキルホスフィン酸エステルおよび他の成分よりなる混合物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6384022B1 (en) * | 1996-06-17 | 2002-05-07 | Guilford Pharmaceuticals Inc. | Prodrugs of NAALAdase inhibitors |
WO2002064604A1 (fr) * | 2001-02-14 | 2002-08-22 | Japan Science And Technology Corporation | Procede de preparation d'oxydes d'alcenylphosphine ou d'esters alcenylphosphiniques |
DE10153780C1 (de) | 2001-11-02 | 2002-11-28 | Clariant Gmbh | Verfahren zur Herstellung von Carboxyethylmethylphosphinsäureglykolester und ihre Verwendung |
CN102177164B (zh) * | 2008-11-05 | 2015-02-11 | 科莱恩金融(Bvi)有限公司 | 利用烯丙醇/丙烯醛制备二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐的方法,以及它们的用途 |
-
2008
- 2008-11-06 DE DE102008056227A patent/DE102008056227A1/de not_active Withdrawn
-
2009
- 2009-10-06 US US13/125,361 patent/US20110237720A1/en not_active Abandoned
- 2009-10-06 CN CN2009801401478A patent/CN102177168A/zh active Pending
- 2009-10-06 JP JP2011533570A patent/JP2012507478A/ja active Pending
- 2009-10-06 EP EP09778830A patent/EP2352737A1/de not_active Withdrawn
- 2009-10-06 WO PCT/EP2009/007127 patent/WO2010051887A1/de active Application Filing
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS56133034A (en) * | 1979-12-12 | 1981-10-17 | Huels Chemische Werke Ag | Hydrogenating treating method for catalyst containing cobalt used for hydrocarboxylation |
JPH02212496A (ja) * | 1989-02-10 | 1990-08-23 | Agency Of Ind Science & Technol | ホスフイニルアルデヒド誘導体の製造法 |
JPH05502447A (ja) * | 1989-11-27 | 1993-04-28 | ヘキスト・アクチェンゲゼルシャフト | 2―ヒドロキシ―エチルホスホン酸ジアルキルエステルの酸化法 |
JP2001518905A (ja) * | 1997-04-15 | 2001-10-16 | ビーエーエスエフ アクチェンゲゼルシャフト | ビニルホスホン酸化合物の製造方法 |
JP2002332290A (ja) * | 2001-03-08 | 2002-11-22 | Japan Science & Technology Corp | アルケニルホスフィン酸エステル類の製造方法 |
JP2004075650A (ja) * | 2002-08-22 | 2004-03-11 | National Institute Of Advanced Industrial & Technology | アルケニルリン化合物及びその製造方法 |
JP2007238617A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシ官能化ジアルキルホスフィン酸塩から組成される混合物、それの使用及び製造方法 |
JP2007238940A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシ官能化ジアルキルホスフィン酸から組成される混合物、それの使用及び製造方法 |
JP2007238616A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシル官能化ジアルキルホスフィン酸エステルおよび他の成分よりなる混合物 |
Non-Patent Citations (2)
Title |
---|
JPN5012001695; SYLVINE DEPRELE: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY V124 N32, 20020101, P9387 * |
JPN5012004744; MONTCHAMP J L: JOURNAL OF ORGANOMETALLIC CHEMISTRY V690 N10, 20050516, P2388-2406 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2011162503A (ja) * | 2010-02-12 | 2011-08-25 | National Institute Of Advanced Industrial Science & Technology | 含パラジウム化合物、その製造方法及びこれを用いる有機化合物の製造法 |
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