JP2012508196A - アクリロニトリル類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
アクリロニトリル類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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- JP2012508196A JP2012508196A JP2011535017A JP2011535017A JP2012508196A JP 2012508196 A JP2012508196 A JP 2012508196A JP 2011535017 A JP2011535017 A JP 2011535017A JP 2011535017 A JP2011535017 A JP 2011535017A JP 2012508196 A JP2012508196 A JP 2012508196A
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- Prior art keywords
- acid
- ester
- catalyst
- alkyl
- salt
- 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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- 239000002253 acid Substances 0.000 title claims abstract description 121
- 238000000034 method Methods 0.000 title claims abstract description 74
- 150000007513 acids Chemical class 0.000 title claims abstract description 28
- 150000008360 acrylonitriles Chemical class 0.000 title description 9
- -1 azo compound Chemical class 0.000 claims abstract description 125
- 150000002148 esters Chemical class 0.000 claims abstract description 72
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 239000003054 catalyst Substances 0.000 claims abstract description 55
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 32
- 150000003624 transition metals Chemical class 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 20
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 19
- 150000003623 transition metal compounds Chemical class 0.000 claims abstract description 19
- 229910052791 calcium Inorganic materials 0.000 claims abstract description 17
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 17
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 17
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 15
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 150000001336 alkenes Chemical class 0.000 claims abstract description 14
- 229910052718 tin Inorganic materials 0.000 claims abstract description 14
- 229910052726 zirconium Inorganic materials 0.000 claims abstract description 14
- 229910052742 iron Inorganic materials 0.000 claims abstract description 13
- 239000003446 ligand Substances 0.000 claims abstract description 13
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 13
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052759 nickel Inorganic materials 0.000 claims abstract description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 229910052712 strontium Inorganic materials 0.000 claims abstract description 7
- 229910052787 antimony Inorganic materials 0.000 claims abstract description 6
- 229910052732 germanium Inorganic materials 0.000 claims abstract description 6
- 229910052748 manganese Inorganic materials 0.000 claims abstract description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 5
- 150000002829 nitrogen Chemical class 0.000 claims abstract description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 229910052802 copper Inorganic materials 0.000 claims abstract description 3
- 150000004678 hydrides Chemical class 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims description 74
- 239000002184 metal Substances 0.000 claims description 74
- 238000006243 chemical reaction Methods 0.000 claims description 70
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 43
- 229920000642 polymer Polymers 0.000 claims description 36
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 34
- 239000003063 flame retardant Substances 0.000 claims description 28
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims description 18
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 17
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 17
- 229920000728 polyester Polymers 0.000 claims description 17
- 239000000654 additive Substances 0.000 claims description 16
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 15
- 239000012778 molding material Substances 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 150000002739 metals Chemical class 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 11
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 11
- 150000001298 alcohols Chemical class 0.000 claims description 11
- 239000002585 base Substances 0.000 claims description 11
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Chemical group [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 11
- 229910052684 Cerium Inorganic materials 0.000 claims description 10
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 10
- 150000002736 metal compounds Chemical class 0.000 claims description 10
- 239000011591 potassium Chemical group 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 238000000465 moulding Methods 0.000 claims description 9
- 229920001187 thermosetting polymer Polymers 0.000 claims description 9
- 239000004634 thermosetting polymer Substances 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 239000000945 filler Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 229920001169 thermoplastic Polymers 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical group [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 7
- 239000011707 mineral Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 239000004416 thermosoftening plastic Substances 0.000 claims description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000001913 cellulose Substances 0.000 claims description 6
- 229920002678 cellulose Polymers 0.000 claims description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 claims description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 5
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 5
- 229910000103 lithium hydride Inorganic materials 0.000 claims description 5
- 229910052987 metal hydride Inorganic materials 0.000 claims description 5
- 150000004681 metal hydrides Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical group [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 claims description 5
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 5
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- HPGPEWYJWRWDTP-UHFFFAOYSA-N lithium peroxide Chemical group [Li+].[Li+].[O-][O-] HPGPEWYJWRWDTP-UHFFFAOYSA-N 0.000 claims description 4
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 claims description 4
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical group [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 4
- 230000002787 reinforcement Effects 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 4
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical group [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical group NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 3
- 239000003431 cross linking reagent Substances 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 3
- 150000004692 metal hydroxides Chemical class 0.000 claims description 3
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 3
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims description 3
- JRKICGRDRMAZLK-UHFFFAOYSA-N peroxydisulfuric acid Chemical compound OS(=O)(=O)OOS(O)(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-N 0.000 claims description 3
- 229920000647 polyepoxide Polymers 0.000 claims description 3
- 229920002635 polyurethane Polymers 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 239000003352 sequestering agent Substances 0.000 claims description 3
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 3
- IHXNSHZBFXGOJM-HWKANZROSA-N (e)-2-methylbut-2-enenitrile Chemical compound C\C=C(/C)C#N IHXNSHZBFXGOJM-HWKANZROSA-N 0.000 claims description 2
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- LXEKPEMOWBOYRF-UHFFFAOYSA-N [2-[(1-azaniumyl-1-imino-2-methylpropan-2-yl)diazenyl]-2-methylpropanimidoyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C(C)(C)N=NC(C)(C)C(N)=N LXEKPEMOWBOYRF-UHFFFAOYSA-N 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 2
- 238000005470 impregnation Methods 0.000 claims description 2
- 239000002480 mineral oil Substances 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- YEYKMVJDLWJFOA-UHFFFAOYSA-N 2-propoxyethanol Chemical compound CCCOCCO YEYKMVJDLWJFOA-UHFFFAOYSA-N 0.000 claims 1
- VKEQBMCRQDSRET-UHFFFAOYSA-N Methylone Chemical compound CNC(C)C(=O)C1=CC=C2OCOC2=C1 VKEQBMCRQDSRET-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 229910000095 alkaline earth hydride Inorganic materials 0.000 claims 1
- 239000012459 cleaning agent Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 claims 1
- 229920005594 polymer fiber Polymers 0.000 claims 1
- 229920006254 polymer film Polymers 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000002904 solvent Substances 0.000 description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 33
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 32
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000243 solution Substances 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 239000004952 Polyamide Substances 0.000 description 20
- 229920002647 polyamide Polymers 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 16
- 229910052698 phosphorus Inorganic materials 0.000 description 16
- 239000011701 zinc Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 14
- 239000011574 phosphorus Substances 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 239000011575 calcium Substances 0.000 description 13
- 239000010936 titanium Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 239000011135 tin Substances 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 10
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 8
- NTECLNXJUWYYGM-UHFFFAOYSA-N 3-[ethyl(hydroxy)phosphoryl]propanoic acid Chemical compound CCP(O)(=O)CCC(O)=O NTECLNXJUWYYGM-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 230000032050 esterification Effects 0.000 description 8
- 238000005886 esterification reaction Methods 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
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- SZQABOJVTZVBHE-UHFFFAOYSA-N carbon monoxide;rhodium Chemical group [Rh].[Rh].[Rh].[Rh].[Rh].[Rh].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] SZQABOJVTZVBHE-UHFFFAOYSA-N 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
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- 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
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 1
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- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 1
- 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
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- LDMNYTKHBHFXNG-UHFFFAOYSA-H disodium;platinum(4+);hexahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Pt+4] LDMNYTKHBHFXNG-UHFFFAOYSA-H 0.000 description 1
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- GBBAWZSGWFBMBT-UHFFFAOYSA-N ethoxy(ethyl)phosphinous acid Chemical compound CCOP(O)CC GBBAWZSGWFBMBT-UHFFFAOYSA-N 0.000 description 1
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- 125000003916 ethylene diamine group Chemical group 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
- 239000012467 final product Substances 0.000 description 1
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- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 description 1
- QWVBGCWRHHXMRM-UHFFFAOYSA-N hexadecoxycarbonyloxy hexadecyl carbonate Chemical compound CCCCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCCCC QWVBGCWRHHXMRM-UHFFFAOYSA-N 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
- MYAJTCUQMQREFZ-UHFFFAOYSA-K tppts Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 MYAJTCUQMQREFZ-UHFFFAOYSA-K 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical class OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- JDUSEMYGYCYQSK-UHFFFAOYSA-L trimagnesium;dioxido(oxidooxy)borane Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]OB([O-])[O-].[O-]OB([O-])[O-] JDUSEMYGYCYQSK-UHFFFAOYSA-L 0.000 description 1
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
- HYWCXWRMUZYRPH-UHFFFAOYSA-N trimethyl(prop-2-enyl)silane Chemical compound C[Si](C)(C)CC=C HYWCXWRMUZYRPH-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CENHPXAQKISCGD-UHFFFAOYSA-N trioxathietane 4,4-dioxide Chemical compound O=S1(=O)OOO1 CENHPXAQKISCGD-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229910000406 trisodium phosphate Inorganic materials 0.000 description 1
- 235000019801 trisodium phosphate Nutrition 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
- 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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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
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- C07—ORGANIC CHEMISTRY
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- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
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- C07F9/4808—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the acid moiety containing a substituent or structure which is considered as characteristic
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- C07F9/4866—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof the ester moiety containing a substituent or structure which is considered as characteristic
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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の存在下に式(V)の化合物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)こうして得られ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、この際、R1、R2、R3、R4、R5、R6、R7は、同一かまたは異なり、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、そして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り、そして触媒Bは、過酸化物形成化合物、及び/またはパーオキソ化合物、及び/またはアゾ化合物、及び/またはアルカリ−及び/またはアルカリ土類金属、−水素化物及び/または−アルコレートであり、そして触媒Cは酸または塩基である、前記方法に関する。
Description
a) 次式
c) この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、基R9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R10によって置換されたフェニル−または少なくとも一つのR10によって置換されたナフチルを表す。R10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(R11)M、−CO2M、−PO3M2、−AsO3M2、−SiO2M、−C(CF3)2OM(M=H、Li、NaまたはK)を表し、ここでR11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、R9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。
a) 反応混合物を循環させるように構成された、それ自体は密閉されかつ冷却設備及び排水口を備えた反応器中に、反応器体積に相当する体積量の製造するべき単官能化ジアルキルホスフィン酸エステル(VI)を、場合により、金属アルコレートに相当する溶剤としてのアルコールとの混合物として、仕込み、そして循環すること、及び
b)前記反応器中に、アルキル亜ホスホン酸エステル(II)、アクリロニトリル類(V)、及び金属アルコレートのアルコール性溶液を、循環された反応器の内容物を冷却しながら導入し、そして約5〜120分の期間、約0〜80℃の温度で反応させ、この際、アルキル亜ホスホン酸エステル(II)とアクリロニトリル類(V)とのモル比は約1:0.9〜2とし、そして金属アルコレートの量は、アルキル亜ホスホン酸エステル(II)を基準として約0.1〜5モル%とし、及び
c)反応器の排出口を介して、プロセス生成物を含む混合物を抜き取り、そしてこの混合物から、単官能化ジアルキルホスフィン酸エステル(V)を蒸留によって分離する、
ことを特徴とする前記方法である。
a)アルキル亜ホスホン酸エステル(II)、アクリロニトリル類(V)、及び金属アルコレートのアルコール性溶液を、別々に反応器に導入する、
b)アルキル亜ホスホン酸エステル(II)とアクリロニトリル類(V)との混合物を、金属アルコレートのアルコール溶液とは別に、反応器中に導入する、または
c)アルキル亜ホスホン酸エステル(II)と金属アルコレートのアルコール性溶液との混合物を、アクリロニトリル類(V)とは別に、反応器中に導入する、
ことによって行うことができる。
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。残留物を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、そして生成物を集める。こうして92g(理論値の98%)のエチル亜ホスホン酸が得られる。
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。収量: 374g(理論値の83%)のエチル亜ホスホン酸ブチルエステル。
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。収量: 129g(理論値の94%)の無色透明の生成物としての(エチル亜ホスホン酸−2−ヒドロキシエチルエステル)。
564g(6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む。この反応混合物を100℃に加熱した後、常圧下に1時間かけて、371g(7モル)のアクリロニトリル及び500gの5%濃度パーオキソ二硫酸ナトリウム溶液(アクリロニトリルに対して1.5モル%)を滴下する。引き続いて、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、そして抽出する。不溶性の塩を濾別する。その濾液の溶剤を真空下に分離し、その残留物をアセトンから再結晶化する。732g(理論値の83%)のエチル−(2−シアノエチル)−ホスフィン酸が油状物として得られる。
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)及び67g(1モル)のメタクリロニトリルを、攪拌機、還流冷却器、温度計及び窒素入口を備えた四つ首丸底フラスコに満たしそして加温する。1時間かけて、約100℃で、エタノール中のAIBNの5%濃度溶液98.4gを滴下する。その後、溶剤を真空下に留去する。137gのエチル−(2−シアノ−2−メチルエチル)−ホスフィン酸が得られる。
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、447g(3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159g(3モル)のアクリロニトリルを仕込んだ。攪拌下に、15mlの酪酸ナトリウム(ブタノール中30%濃度)を、最大120℃の反応温度が調節されるような速度で滴下する。こうして得られた粗製生成物を真空下に蒸留する。554g(理論値の91%)のエチル−(2−シアノエチル)−ホスフィン酸ブチルエステルが無色の液体として得られた。
1Lの内容積を有するループ型反応器に、914g(4.5モル)のエチル−(2−シアノエチル)−ホスフィン酸ブチルエステル(例7のように製造したもの)及び62g(1.35モル)のエタノールからなる混合物を充填する。ポンプの始動後に、726g(6.00モル)のエチル亜ホスホン酸エチルエステル及び318g(6.00モル)のアクリロニトリルからなる混合物、並びに193g(2.61モル)のブタノール中の22.4g(0.20モル)の酪酸カリウムの溶液を1時間毎に計量添加し、この際、冷水循環を用いて約40℃の温度を維持した。あふれた粗製生成物を30時間集め、そして反応器から排出された生成物と合わせて37.1kgの総量を与えた。水ジェット真空下に蒸留によって低沸点物を分離しそして濾過した後に、生成物を薄膜蒸発器で真空下に蒸留し、そして29.1kg(143.5モル)のエチル−(2−シアノエチル)−ホスフィン酸ブチルエステルが得られた。これは、反応器に仕込んだ量を差し引くと、約970g/L*hの工率で93.0%のP収率に相当する。この例が示す通り、モノシアノ官能化ジアルキルホスフィン酸エステルの連続式の製造が良好な空間時間収量で可能である。
217gのトルエン中の150g(1モル)のエチル亜ホスホン酸ブチルエステル(例2のように製造したもの)及び80g(1.2モル)のメタクリロニトリルを約100℃に加温する。攪拌下に、トルエン中のWakoV65の10%濃度溶液124gを計量添加する。溶剤を真空下に留去する。182g(理論値の84%)のエチル−(2−シアノ−2−メチルエチル)−ホスフィン酸ブチルエステルが得られる。
441g(3モル)の得られたエチル−(2−シアノエチル)−ホスフィン酸(例5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、生じた水を共沸蒸留によって除去する。生成物であるエチル−(2−シアノエチル)−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することによって精製する。
540g(3.0モル)のエチル−(2−シアノ−2−メチルエチル)−ホスフィン酸(例6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。エステル化の終了後、トルエンを真空下に分離する。643g(理論値の92%)のエチル−(2−シアノ−2−メチルエチル)−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。
441g(3.0モル)のエチル−(2−シアノエチル)−ホスフィン酸(例5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。510g(理論値の89%)のエチル−(2−シアノエチル)−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。
攪拌装置中で、147g(1モル)のエチル−(2−シアノエチル)−ホスフィン酸(例5のように製造したもの)を200ml(2モル)の濃塩酸中に溶解する。この混合物を十分な攪拌下に約90℃に加温し、そしてこの温度で約6時間反応させた。反応溶液の冷却後、生じたアンモニウムヒドロクロライドを濾過する。反応溶液を濃縮すると、アンモニウムヒドロクロライドが更に析出し、これをこの熱い反応溶液の濾過によって分離する。次いで、水を真空下に完全に留去する。その残留物を酢酸中に取り入れそして抽出する。不溶性の塩を濾別する。その濾液の溶剤を真空下に分離し、そしてその残留物をアセトンから再結晶化する。161g(理論値の97%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸が固形物として得られる。
攪拌装置中で、217g(1モル)のエチル−(2−メチル−2−シアノエチル)ホスフィン酸ブチルエステル(例9のように製造したもの)を200ml(2モル)の濃塩酸中に溶解する。この混合物を十分な攪拌下に約90℃に加温し、そしてこの温度で約8時間反応させた。冷却後、生じたアンモニウムヒドロクロライドを反応溶液から濾過する。反応溶液を濃縮すると、アンモニウムヒドロクロライドが更に析出し、これを、この熱い反応溶液の濾過によって分離する。次いで、水を真空下に完全に留去する。その残留物を酢酸中に取り入れそして抽出する。不溶性の塩を濾別する。その濾液の溶剤を真空下に分離し、そしてその残留物をアセトンから再結晶化する。169g(理論値の94%)の3−(エチルヒドロキシホスフィニル)−2−メチルプロピオン酸が固形物として得られる。
攪拌装置中に、150gのブタノール、65gの水、150g(3.75モル)の水酸化ナトリウム及び183g(1.25モル)のエチル−(2−シアノエチル)−ホスフィン酸(例5のように製造したもの)を仕込む。この混合物を、十分な攪拌下に約120℃に加温し、そしてこの温度で約6時間反応させた。次いで、250mlの水を加え、そしてブタノールを蒸留によって反応混合物から除去した。更に500mlの水を加えた後、混合物を、約184g(1.88モル)の濃硫酸の添加によって中和した。次いで、水を真空下に留去した。その残留物をテトラヒドロフラン中に取り入れそして抽出する。不溶性の塩を濾別する。その濾液の溶剤を真空下に分離しそしてその残留物をアセトンから再結晶化する。203g(理論値の98%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸が固形物として得られる。
攪拌装置中に、150gのエタノール、65gの水、150g(3.75モル)の水酸化ナトリウム及び183g(1.25モル)のエチル−(2−シアノエチル)−ホスフィン酸(例5のように製造したもの)を仕込む。この混合物を還流下に加温し、そしてその温度下に約10時間反応させた。次いで、水及びブタノールを蒸留によって反応混合物から除去した。更に500mlの水を加えた後、この混合物を、約61g(0.63モル)の濃硫酸の添加によって中和した。次いで、水を真空下に留去する。その残留物をエタノール中に取り込みそして不溶性の塩を濾別する。その濾液の溶剤を真空下に分離する。234g(理論値の89%)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固形物として得られる。
攪拌装置中に、150gのブタノール、65gの水、150g(3.75モル)の水酸化ナトリウム及び271g(1.25モル)のエチル−(2−シアノ−2−メチルエチル)−ホスフィン酸ブチルエステル(例9のように製造したもの)を仕込む。この混合物を、十分な攪拌下に約120℃に加温し、そしてこの温度下に約8時間反応させた。次いで、250mlの水を加え、そしてブタノールを蒸留によって反応混合物から除去した。更に500mlの水を加えた後、この混合物を、約184g(1.88モル)の濃硫酸の添加によって中和した。次いで、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する。不溶性の塩を濾別する。その濾液の溶剤を真空下に分離し、そしてその残留物をアセトンから再結晶化させる。216g(理論値の96%)の3−(エチルヒドロキシホスフィニル)−2−メチルプロピオン酸が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15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480g(6モル)の50%濃度水酸化ナトリウム溶液で中和する。次いで、水を真空下に留去する。624g(理論値の99%)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固形物として得られる。
630g(3モル)の3−(エチルヒドロキシホスフィニル)−プロピオン酸ナトリウム塩(例16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147g(1.5モル)の濃硫酸の添加によって中和する。次いで、水を真空下に留去する。その残留物をエタノール中に取り込みそして不溶性の塩を濾別する。その濾液の溶剤を真空下に分離する。488g(理論値の98%)の3−(エチルヒドロキシホスフィニル)−プロピオン酸が固形物として得られる。
498g(3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15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、生じ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によって精製する。
540g(3.0モル)の3−(エチルヒドロキシホスフィニル)−2−メチルプロピオン酸(例17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。894g(理論値の92%)の3−(エチル−4−ヒドロキシブトキシ−ホスフィニル)−2−メチルプロピオン酸−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、易揮発性の成分を留去する。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。
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15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(12mol)の50%濃度水酸化ナトリウム溶液で中和する。85℃で、Al2(SO4)3・14H2Oの46%濃度水溶液2583gの混合物を加える。次いで、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。
180g(1モル)の3−(エチルヒドロキシホスフィニル)−2−メチルプロピオン酸(例17のように製造したもの)及び170gの四酪酸チタンを500mlのトルエン中で40時間還流下に加熱する。この際生じたブタノールを、トルエンの一部と一緒に時折留去する。生じた溶液から次いで溶剤を除去する。184g(理論値の91%)の3−(エチルヒドロキシホスフィニル)−2−メチ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22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。
15.2gの3−(エチルヒドロキシホスフィニル)−2−メチルプロピオン酸(例17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のテトラブチルチタネート及び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。ポリマー(438g)は0.6%のリンを含み、LOIは34である。
14gの3−(エチルヒドロキシホスフィニル)−プロピオン酸(例13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のテトラブチルチタネート及び0.05gの酢酸リチウムを加え、そしてこの混合物を先ず2時間攪拌下に130〜180℃に加熱し、その後、減圧下に270℃に加熱する。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、温度計及び窒素導入口を備えた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)−2−メチルプロピオン酸(例17のように製造したもの)24.1g(0.13モル)を攪拌しながら最大150℃に加熱する。30分後、透明な溶融物が生ずる。150℃で更に1時間攪拌した後、この溶融物を冷却しそして粉砕する。3.3重量%のリン含有率を有する118.5gの白色の粉末が得られる。
攪拌機、水分離器、温度計、還流冷却器及び窒素導入口を備えた2Lのフラスコ中で、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22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、約190℃で更に攪拌する。14gの水を分離した後に、キシレンを留去し、そしてポリマー溶融物を冷却する。2.3重量%のリン含有率を有する91.5gの白色の粉末が得られる。
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23のように製造したもの)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。
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−(エチルヒドロキシホスフィニル)−2−メチルプロピオン酸チタン塩(例24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℃でポリマー成形体に加工する。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) 単官能化ジアルキルホスフィン酸誘導体(VI)を触媒Cの存在下に反応させて、次式
ことを特徴とする、上記方法。 - 段階c)の後に得られた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、そして各々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)、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)またはc)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1〜3の一つまたはそれ以上の方法。
- R1、R2、R3、R4、R5、R6、R7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1〜4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1〜5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7亜族及び第8亜族からのものであることを特徴とする、請求項1〜6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、ロジウム、ニッケル、パラジウム、白金、及び/またはルテニウム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。
- 触媒Bが、過酸化水素、過酸化ナトリウム、過酸化リチウム、過硫酸カリウム、過硫酸ナトリウム、過硫酸アンモニウム、パーオキソ二硫酸ナトリウム、パーオキソホウ酸カリウム、過酢酸、過酸化ベンゾイル、過酸化ジ−t−ブチル及び/またはパーオキソ二硫酸であるか、及び/またはアゾジイソブチロニトリル、2,2’−アゾビス(2−アミジノプロパン)−ジヒドロクロライド及び/または2,2’−アゾビス(N,N’−ジメチレン−イソブチルアミジン)−ジヒドロクロライドであるか、及び/またはリチウム、水素化リチウム、水素化アルミニウムリチウム、メチルリチウム、ブチルリチウム、t−ブチルリチウム、リチウムジイソプロピルアミド、ナトリウム、水素化ナトリウム、水素化ホウ素ナトリウム、ナトリウムメタノレート、ナトリウムエタノレートまたは酪酸ナトリウム、カリウムメタノレート、カリウムエタノレート及び/または酪酸カリウム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。
- 触媒Cが、金属、金属水素化物、金属水酸化物及び金属アルコレート及び鉱酸であることを特徴とする、請求項1〜9の一つまたはそれ以上の方法。
- アクリロニトリル類(V)がアクリロニトリル、メタクリロニトリル、エチル−2−シアノアクリレート、3−フェニルアクリロニトリル、2−メチル−2−ブテンニトリル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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EP (1) | EP2367833B1 (ja) |
JP (1) | JP5570517B2 (ja) |
CN (1) | CN102186865B (ja) |
DE (1) | DE102008056342A1 (ja) |
ES (1) | ES2432382T3 (ja) |
WO (1) | WO2010051891A1 (ja) |
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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 |
WO2010051883A1 (de) * | 2008-11-05 | 2010-05-14 | Clariant International Ltd | Verfahren zur herstellung von dialkylphosphinsäuren, -estern und -salzen mittels allylalkoholen/acroleinen und ihre verwendung |
DE102008056339A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von mono-aminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen 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 |
WO2010051893A1 (de) * | 2008-11-07 | 2010-05-14 | Clariant International Ltd | Verfahren zur herstellung von dialkylphosphinsäuren, -estern und -salzen mittels acrylsäurederivaten 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 |
DE102008060036A1 (de) * | 2008-12-02 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylester einer Carbonsäure und ihre Verwendung |
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-
2008
- 2008-11-07 DE DE102008056342A patent/DE102008056342A1/de not_active Withdrawn
-
2009
- 2009-10-06 JP JP2011535017A patent/JP5570517B2/ja not_active Expired - Fee Related
- 2009-10-06 EP EP09736137.2A patent/EP2367833B1/de not_active Not-in-force
- 2009-10-06 WO PCT/EP2009/007131 patent/WO2010051891A1/de active Application Filing
- 2009-10-06 CN CN200980140668.3A patent/CN102186865B/zh not_active Expired - Fee Related
- 2009-10-06 US US13/127,069 patent/US8735477B2/en not_active Expired - Fee Related
- 2009-10-06 ES ES09736137T patent/ES2432382T3/es active Active
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Publication number | Publication date |
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US8735477B2 (en) | 2014-05-27 |
CN102186865B (zh) | 2015-10-14 |
DE102008056342A1 (de) | 2010-05-12 |
JP5570517B2 (ja) | 2014-08-13 |
CN102186865A (zh) | 2011-09-14 |
ES2432382T3 (es) | 2013-12-03 |
EP2367833A1 (de) | 2011-09-28 |
EP2367833B1 (de) | 2013-08-28 |
WO2010051891A1 (de) | 2010-05-14 |
US20110213060A1 (en) | 2011-09-01 |
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