CN102171226B - 利用烯丙基化合物制备单烯丙基官能化的二烷基次膦酸、其盐或酯的方法以及它们的用途 - Google Patents
利用烯丙基化合物制备单烯丙基官能化的二烷基次膦酸、其盐或酯的方法以及它们的用途 Download PDFInfo
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- CN102171226B CN102171226B CN200980138622.8A CN200980138622A CN102171226B CN 102171226 B CN102171226 B CN 102171226B CN 200980138622 A CN200980138622 A CN 200980138622A CN 102171226 B CN102171226 B CN 102171226B
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
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- 239000003444 phase transfer catalyst Substances 0.000 description 1
- REGPDRSDSZELCD-UHFFFAOYSA-N phenol;zinc Chemical compound [Zn].OC1=CC=CC=C1 REGPDRSDSZELCD-UHFFFAOYSA-N 0.000 description 1
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- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- NUSQOFAKCBLANB-UHFFFAOYSA-N phthalocyanine tetrasulfonic acid Chemical compound C12=CC(S(=O)(=O)O)=CC=C2C(N=C2NC(C3=CC=C(C=C32)S(O)(=O)=O)=N2)=NC1=NC([C]1C=CC(=CC1=1)S(O)(=O)=O)=NC=1N=C1[C]3C=CC(S(O)(=O)=O)=CC3=C2N1 NUSQOFAKCBLANB-UHFFFAOYSA-N 0.000 description 1
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- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- PXXKQOPKNFECSZ-UHFFFAOYSA-N platinum rhodium Chemical compound [Rh].[Pt] PXXKQOPKNFECSZ-UHFFFAOYSA-N 0.000 description 1
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- 150000003141 primary amines Chemical class 0.000 description 1
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- WXKCRCGKCOKJEF-UHFFFAOYSA-N prop-2-enyl 2-cyanoacetate Chemical compound C=CCOC(=O)CC#N WXKCRCGKCOKJEF-UHFFFAOYSA-N 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- AXLMPTNTPOWPLT-UHFFFAOYSA-N prop-2-enyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCC=C AXLMPTNTPOWPLT-UHFFFAOYSA-N 0.000 description 1
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- IKNCGYCHMGNBCP-UHFFFAOYSA-N propan-1-olate Chemical compound CCC[O-] IKNCGYCHMGNBCP-UHFFFAOYSA-N 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
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- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- GJPYYNMJTJNYTO-UHFFFAOYSA-J sodium aluminium sulfate Chemical compound [Na+].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O GJPYYNMJTJNYTO-UHFFFAOYSA-J 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
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- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
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- 239000010959 steel Substances 0.000 description 1
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- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
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- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
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- 229910000349 titanium oxysulfate Inorganic materials 0.000 description 1
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- 230000007704 transition Effects 0.000 description 1
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- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- NGOCMUBXJDDBLB-UHFFFAOYSA-N trifluoromethanesulfonic acid;zinc Chemical compound [Zn].OS(=O)(=O)C(F)(F)F NGOCMUBXJDDBLB-UHFFFAOYSA-N 0.000 description 1
- IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 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
- ZBZHVBPVQIHFJN-UHFFFAOYSA-N trimethylalumane Chemical compound C[Al](C)C.C[Al](C)C ZBZHVBPVQIHFJN-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-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
- DAGQYUCAQQEEJD-UHFFFAOYSA-N tris(2-methylpropyl)phosphane Chemical compound CC(C)CP(CC(C)C)CC(C)C DAGQYUCAQQEEJD-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
- 229960004418 trolamine Drugs 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
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate 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
- 239000011592 zinc chloride Substances 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
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 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
- 229960001296 zinc oxide Drugs 0.000 description 1
- 229940105296 zinc peroxide Drugs 0.000 description 1
- LRXTYHSAJDENHV-UHFFFAOYSA-H zinc phosphate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O LRXTYHSAJDENHV-UHFFFAOYSA-H 0.000 description 1
- 229910000165 zinc phosphate Inorganic materials 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
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
- 235000019352 zinc silicate Nutrition 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
- HJSYJHHRQVHHMQ-ODZAUARKSA-L zinc;(z)-but-2-enedioate Chemical compound [Zn+2].[O-]C(=O)\C=C/C([O-])=O HJSYJHHRQVHHMQ-ODZAUARKSA-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
- 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
- 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
- MFMKGXZULQONRI-UHFFFAOYSA-L zinc;diiodate Chemical compound [Zn+2].[O-]I(=O)=O.[O-]I(=O)=O MFMKGXZULQONRI-UHFFFAOYSA-L 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
- 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
- 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
- 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
- VXEZTJBNLUVPGK-UHFFFAOYSA-N zirconium(4+) hydrate Chemical compound O.[Zr+4] VXEZTJBNLUVPGK-UHFFFAOYSA-N 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
- IPCAPQRVQMIMAN-UHFFFAOYSA-L zirconyl chloride Chemical compound Cl[Zr](Cl)=O IPCAPQRVQMIMAN-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- 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)]
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Abstract
本发明涉及一种用烯丙基化合物制备单烯丙基官能化的二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐的方法,其特征在于,a)使次膦酸源(I)与烯烃(IV)在催化剂A的存在下反应成烷基亚膦酸、其盐或酯(II),b)使如此获得的烷基亚膦酸、其盐或酯(II)与式(V)的烯丙基化合物在催化剂B和碱的存在下反应成单烯丙基官能化的二烷基次膦酸衍生物(III),其中R1、R2、R3、R4、R5、R6、R7、R8、R9相同或不同,且彼此独立地表示H、C1-C18-烷基、C6-C18-芳基、C6-C18芳烷基、C6-C18-烷基芳基等,和X表示H、C1-C18-烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基、Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K和/或质子化的氮碱,催化剂A和B是过渡金属和/或过渡金属化合物和/或催化剂体系,所述催化剂体系由过渡金属和/或过渡金属化合物和至少一种配体构成。
Description
本发明涉及一种利用烯丙基化合物制备单烯丙基官能化的二烷基次膦酸、其盐或酯的方法以及它们的用途。
迄今为止还没有经济上和工业上可行的、且尤其能够获得高空/时产率的制备单烯丙基官能化的二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐的方法。也没有这样的方法,其在没有干扰性卤素化合物作为反应物的情况下是充分有效的;并且没有这样的方法,在该方法中最终产物能够轻易获得或分离,或者可以在特定的反应条件下(例如酯交换)以有针对性地且令人期望地制得。
该问题通过一种制备单烯丙基官能化的二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐的方法得以解决,其特征在于,
a)使次膦酸源(I)
与烯烃(IV)
在催化剂A的存在下反应成烷基亚膦酸、其盐或酯(II)
b)使如此获得的烷基亚膦酸、其盐或酯II与式(V)的烯丙基化合物
在催化剂B和碱的存在下反应成单烯丙基官能化的二烷基次膦酸衍生物(III)
其中,R1、R2、R3、R4、R5、R6、R7、R8、R9相同或不同,且彼此独立地表示H、C1-C18-烷基、C6-C18-芳基、C6-C18芳烷基、C6-C18-烷基芳基、CN、CHO、OC(O)CH2CN、CH(OH)C2H5、CH2CH(OH)CH3、9-蒽、2-吡咯烷酮、(CH2)mOH、(CH2)mNH2、(CH2)mNCS、(CH2)mNC(S)NH2、(CH2)mSH、(CH2)mS-2-噻唑啉、(CH2)mSiMe3、C(O)R10、(CH2)mC(O)R10、CH=CHR10和/或CH=CH-C(O)R10,并且其中R10表示C1-C8-烷基或C6-C18-芳基,且m为0到10的整数;和X表示H、C1-C18-烷基、C6-C18-芳基、C6-C18-芳烷基、C6-C18-烷基芳基、(CH2)kOH、CH2-CHOH-CH2OH、(CH2)kO(CH2)kH、(CH2)k-CH(OH)-(CH2)kH、(CH2-CH2O)kH、(CH2-C[CH3]HO)kH、(CH2-C[CH3]HO)k(CH2-CH2O)kH、(CH2-CH2O)k(CH2-C[CH3]HO)H、(CH2-CH2O)k-烷基、(CH2-C[CH3]HO)k-烷基、(CH2-C[CH3]HO)k(CH2-CH2O)k-烷基、(CH2-CH2O)k(CH2-C[CH3]HO)O-烷基、(CH2)k-CH=CH(CH2)kH、(CH2)kNH2和/或(CH2)kN[(CH2)kH]2,其中k为0到100的整数,和/或X表示Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Cu、Ni、Li、Na、K、H和/或质子化的氮碱;和Y表示卤素或乙酸酯;和催化剂A和B是过渡金属和/或过渡金属化合物和/或催化剂体系,所述催化剂体系由过渡金属和/或过渡金属化合物和至少一种配体构成。
优选地,将步骤b)之后获得的单烯丙基官能化的二烷基次膦酸、其盐或酯(III)随后在步骤c)中与Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K的金属化合物和/或质子化的氮碱反应生成这些金属和/或含氮化合物相应的单烯丙基官能化的二烷基次膦酸盐(III)。
优选地,将步骤a)之后获得的烷基亚膦酸、其盐或酯(II)和/或步骤b)之后获得的单烯丙基官能化的二烷基次膦酸、其盐或酯(III)和/或分别由此产生的反应溶液,与氧化烯烃或醇M-OH和/或M’-OH发生酯化,并且使分别得到的烷基亚膦酸酯(II)和/或单烯丙基官能化的二烷基次膦酸酯(III)经历另外的反应步骤b)或c)。
优选地,基团C6-C18芳基、C6-C18芳烷基和C6-C18烷基芳基被SO3X2、-C(O)CH3、OH、CH2OH、CH3SO3X2、PO3X2、NH2、NO2、OCH3、SH和/或OC(O)CH3取代。
优选地,R1、R2、R3、R4、R5、R6、R7、R8、R9相同或不同,并且彼此独立地表示H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和/或苯基。
优选地,X表示Ca、Al、Zn、Ti、Mg、Ce、Fe、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、苯基、乙二醇、丙基乙二醇、丁基乙二醇、戊基乙二醇、己基乙二醇、烯丙基和/或甘油。
优选地,m=1至10和k=2至10。
优选地,催化剂体系A和B各自通过一种过渡金属和/或一种过渡金属化合物与至少一种配体反应形成。
优选地,过渡金属和/或过渡金属化合物是源自第七和第八副族的那些。
优选地,过渡金属和/或过渡金属化合物是铑、钌、镍、钯、铂。
优选地,烯丙基化合物(V)是3-氯-1-丙烯、3-氯-2-甲基-1-丙烯、3-氯-1-苯基-1-丙烯、1-氯-2-丁烯、1-氯-3-甲基-2-丁烯、3-溴-1-丙烯、3-溴-2-甲基-1-丙烯、3-溴-1-苯基-1-丙烯、1-溴-2-丁烯、1-溴-3-甲基-2-丁烯、乙酸烯丙酯、乙酸2-甲基烯丙酯。
优选地,碱是碱金属和/或碱土金属,碱金属和/或碱土金属氢化物,碱金属和/或碱土金属醇化物,碱金属和/或碱土金属氢氧化物;胺和/或二胺,和/或有机锂化合物。
优选地,通式M-OH的醇是具有C1-C18的碳链长度的、直链的或支链的、饱和的和不饱和的一元有机醇,和通式M′-OH的醇是具有C1-C18的碳链长度的、直链的或支链的、饱和的和不饱和的多元有机醇。
此外,本发明涉及根据权利要求1至11中的一项或多项制备的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸盐和二烷基次膦酸酯作为用于进一步合成的中间产物,作为粘结剂,作为在环氧树脂、聚氨酯、不饱和聚酯树脂的固化中的交联剂或者促进剂,作为聚合物稳定剂,作为植物保护剂,作为用于人类和动物的治疗剂或治疗剂中的添加剂,作为螯合剂,作为矿物油添加剂,作为抗蚀剂,在洗涤剂和清洁剂应用中,在电子应用中的用途。
本发明同样涉及根据权利要求1至11中的一项或多项制备的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸盐和二烷基次膦酸酯(III)作为阻燃剂,尤其是用于透明漆和发泡型防火涂料的阻燃剂、用于木材和其它含纤维素产品的阻燃剂;作为用于聚合物的反应性和/或非反应性阻燃剂;用于制备阻燃聚合物模塑材料;用于制备阻燃聚合物成型体和/或用于通过浸渍为聚酯和纤维素纯织物和混纺织物进行阻燃性整理的用途。
本发明还涉及阻燃热塑性或热固性聚合物模塑材料,其含有0.5至45重量%的根据权利要求1至11中一项或多项所制备的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸盐或二烷基次膦酸酯(III),0.5至95重量%的热塑性或热固性聚合物或它们的混合物,0至55重量%的添加剂和0至55重量%的填料或增强材料,其中,各组分之和为100重量%。
最后,本发明还涉及阻燃热塑性或热固性聚合物成型体、聚合物膜、聚合物丝和聚合物纤维,其含有0.5至45重量%的根据权利要求1至11中一项或多项所制备的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸盐或二烷基次膦酸酯(III),0.5至95重量%的热塑性或热固性聚合物或它们的混合物,0至55重量%的添加剂和0至55重量%的填料或增强材料,其中,各组分之和为100重量%。
所有上述反应也可以分步进行;同样,在不同的方法步骤中,也可以使用各自产生的反应溶液。
如果步骤b)之后的单烯丙基官能化的二烷基次膦酸(III)是酯,那么优选地可以进行酸或碱水解,以获得游离的单烯丙基官能化的二烷基次膦酸或其盐。
优选地,制备的目标化合物,即单烯丙基官能化的二烷基次膦酸是乙基丙烯基次膦酸、丙基丙烯基次膦酸、异丙基丙烯基次膦酸、丁基丙烯基次膦酸、仲丁基丙烯基次膦酸、异丁基丙烯基次膦酸、2-苯基乙基丙烯基次膦酸、乙基-(2-甲基丙烯基)次膦酸、丙基-(2-甲基丙烯基)次膦酸,异丙基-(2-甲基丙烯基)次膦酸、丁基-(2-甲基丙烯基)次膦酸、仲丁基-(2-甲基丙烯基)次膦酸、异丁基-(2-甲基丙烯基)次膦酸、2-苯基乙基-(2-甲基丙烯基)次膦酸、乙基-(2-丁烯基)次膦酸、丙基-(2-丁烯基)次膦酸、异丁基-(2-丁烯基)次膦酸、丁基-(2-丁烯基)次膦酸、仲丁基-(2-丁烯基)次膦酸、异丁基-(2-丁烯基)次膦酸、2-苯基乙基-(2-丁烯基)次膦酸、乙基-(3-甲基-2-丁烯基)次膦酸、丙基-(3-甲基-2-丁烯基)次膦酸、异丙基-(3-甲基-2-丁烯基)次膦酸、丁基-(3-甲基-2-丁烯基)次膦酸、仲丁基-(3-甲基-2-丁烯基)次膦酸、异丁基-(3-甲基-2-丁烯基)次膦酸、2-苯基乙基-(3-甲基-2-丁烯基)次膦酸;对于酯,是上述单烯丙基官能化的二烷基次膦酸的甲酯、乙酯、异丙酯、丁酯、苯酯、2-羟乙酯、2-羟丙酯、3-羟丙酯、4-羟丁酯、和/或2,3-二羟基丙基酯;和对于盐是上述单烯丙基官能化的二烷基次膦酸的铝(III)盐、钙(II)盐、镁(II)盐、铈(III)盐、Ti(IV)盐和/或锌(II)盐。
优选地,用于催化剂A的过渡金属是第七和第八副族(根据新命名法的第7、8、9或10族的金属)的元素,例如铼、钌、钴、铑、铱、镍、钯、铂。
优选地,作为过渡金属和过渡金属化合物来源,使用其金属盐。合适的盐是无机酸的那些,其含有氟化物、氯化物、溴化物、碘化物、氟酸盐、氯酸盐、溴酸盐、碘酸盐、亚氟酸盐、亚氯酸盐、亚溴酸盐、亚碘酸盐、次氟酸盐、次氯酸盐、次溴酸盐、次碘酸盐、高氟酸盐、高氯酸盐、高溴酸盐、高碘酸盐、氰化物、氰酸盐、硝酸盐、氮化物、亚硝酸盐、氧化物、氢氧化物、硼酸盐、硫酸盐、亚硫酸盐、硫化物、过硫酸盐、硫代硫酸盐、氨基磺酸盐、磷酸盐、亚磷酸盐、次磷酸盐、磷化物、碳酸盐和磺酸盐(例如甲磺酸盐、氯磺酸盐、氟磺酸盐、三氟甲磺酸盐、苯磺酸盐、萘磺酸盐、甲苯磺酸盐、叔丁基磺酸盐、2-羟基丙磺酸盐和磺化离子交换树脂)的阴离子;和/或其含有有机盐,例如乙酰丙酮盐和具有最多20个碳原子的羧酸盐,例如甲酸盐、乙酸盐、丙酸盐、丁酸盐、草酸盐、硬脂酸盐和柠檬酸盐,包括具有最多20个碳原子的卤代羧酸盐,例如三氟乙酸盐、三氯乙酸盐的阴离子。
过渡金属和过渡金属化合物的另一来源是过渡金属与四苯基硼酸阴离子和卤代的四苯基硼酸阴离子的盐,例如全氟苯基硼酸盐。
合适的盐同样包括复盐和络盐,其由一种或多种过渡金属离子,和彼此独立的一种或多种碱金属离子、碱土金属离子、铵离子、有机铵离子、鏻离子和有机鏻离子,和彼此独立的一种或多种上述阴离子构成。合适的复盐是例如六氯钯酸铵和四氯钯酸铵。合适的复盐例如是六氯钯酸铵和四氯钯酸铵。
优选地,过渡金属的来源是元素态的过渡金属和/或在其零价状态的过渡金属化合物。
优选地,将过渡金属以金属态使用或者以与其它的金属的合金使用,在此,优选是硼、锆、钽、钨、铼、钴、铱、镍、钯、铂和/或金。此时,在使用的合金中的过渡金属含量优选是45-99.95重量%。
优选地,以微分散形式(0.1mm-100μm的粒径)使用过渡金属。
优选地,以负载在金属氧化物(例如氧化铝、二氧化硅、二氧化钛、二氧化锆、氧化锌、氧化镍、氧化钒、氧化铬、氧化镁、硅藻土)上,负载在金属碳酸盐(例如碳酸钡、碳酸钙、碳酸锶)上,负载在金属硫酸盐(例如硫酸钡、硫酸钙、硫酸锶)上,负载在金属磷酸盐(例如磷酸铝、磷酸钒)上,负载在金属碳化物(例如碳化硅)上,负载在金属铝酸盐(例如铝酸钙)上,负载在金属硅酸盐(例如硅酸铝、白垩、沸石、膨润土、蒙脱石、锂蒙脱土)上,负载在官能化硅酸盐、官能化硅胶(例如QuadraSilTM)上,负载在官能化聚硅氧烷(例如)上,负载在金属氮化物上,负载在炭、活性炭、莫来石、铝土矿、辉锑矿、白钨矿、钙钛矿、水滑石、杂多阴离子上,负载在官能化和未官能化的纤维素、壳聚糖、角蛋白、杂多阴离子上,负载在离子交换剂(例如AmberliteTM、AmberjetTM、AmbersepTM、 )上,负载在官能化聚合物(例如QuadraPureTM、)上,负载在聚合物键合的磷烷、磷烷氧化物、次膦酸盐、膦酸盐、磷酸盐、胺、铵盐、酰胺、硫代酰胺、脲、硫脲、三嗪、咪唑、吡唑、吡啶、嘧啶、吡嗪、硫醇、硫醚、硫醇酯、醇、烷氧化物、醚、酯、羧酸、乙酸酯、缩醛、肽、杂芳烯、聚乙烯亚胺/二氧化硅和/或树状大分子上的形式使用过渡金属。
合适的金属盐和/或过渡金属的来源同样优选是其络合物。金属盐和/或过渡金属的络合物由金属盐或者过渡金属和一种或多种络合剂构成。合适的络合剂例如是烯烃、二烯烃、腈、二腈、一氧化碳、膦、二膦、亚磷酸酯、二亚磷酸酯、二亚苄基丙酮、环戊二烯、茚或苯乙烯。可以将合适的金属盐和/或过渡金属的络合物负载在上述载体材料上。
优选地,上述负载的过渡金属的含量是0.01至20重量%,更优选0.1至10重量%,尤其是0.2至5重量%,基于载体材料的总质量计。
合适的过渡金属和过渡金属化合物的来源例如是钯、铂、镍、铑;负载在氧化铝、氧化硅、碳酸钡、硫酸钡、碳酸钙、碳酸锶、炭、活性炭上的钯、铂、镍、铑;铂-钯-金合金、铝-镍合金、铁-镍合金、镧系-镍合金、锆-镍合金、铂-铱合金、铂-铑合金;镍、镍-锌-铁氧化物;钯(II)、镍(II)、铂(II)、铑的氯化物、溴化物、碘化物、氟化物、氢化物、氧化物、过氧化物、氰化物、硫酸盐、硝酸盐、磷化物、硼化物、铬氧化物、钴氧化物、碱式碳酸盐、环己烷丁酸盐、氢氧化物、钼酸盐、辛酸盐、草酸盐、高氯酸盐、酞菁化物、5,9,14,18,23,27,32,36-八丁氧基-2,3-萘酞菁化物、磺酸盐、高氯酸盐、硫氰酸盐、双(2,2,6,6-四甲基-3,5-庚二酮酸盐)、丙酸盐、乙酸盐、硬脂酸盐、2-乙基己酸盐、乙酰丙酮化物、六氟乙酰丙酮化物、四氟硼酸盐、硫代硫酸盐、三氟乙酸盐、酞菁四磺酸四钠盐、甲基化物、环戊二烯化物、甲基环戊二烯化物、乙基环戊二烯化物、五甲基环戊二烯化物、2,3,7,8,12,13,17,18-八乙基-21H,23H-卟吩化物、5,10,15,20-四苯基-21H,23H-卟吩化物、双(5-[[4-(二甲氨基)苯基]亚氨基]-8(5H)-喹啉酮)化物、2,11,20,29-四叔丁基-2,3-萘酞菁化物、2,9,16,23-四苯氧基-29H,31H-酞菁化物、5,10,15,20-四(五氟苯基)-21H,23H-卟吩化物,和它们的1,4-双(二苯基膦)丁烷络合物、1,3-双(二苯基膦)丙烷络合物、2-(2′-二叔丁基膦)联苯络合物、乙腈络合物、苯甲腈络合物、乙二胺络合物、氯仿络合物、1,2-双(苯亚磺酰)乙烷络合物、(1,3-双(2,6-二异丙基苯基)咪唑啉)(3-氯吡啶)络合物、2′-(二甲氨基)-2-联苯络合物、二降冰片基膦络合物、2-(二甲氨基甲基)二茂铁络合物、烯丙基络合物、双(二苯基膦)丁烷络合物、(N-琥珀酰亚胺基)双(三苯基膦)络合物、二甲基苯基膦络合物、甲基二苯基膦络合物、1,10-菲咯啉络合物、1,5-环辛二烯络合物、N,N,N′,N′-四甲基乙二胺络合物、三苯基膦络合物、三邻甲苯基膦络合物、三环己基膦络合物、三丁基膦络合物、三乙基膦络合物、2,2′-双(二苯基膦)-1,1′-联萘络合物、1,3-双(2,6-二异丙基苯基)咪唑-2-亚基络合物、1,3-双(均三甲苯基)咪唑-2-亚基络合物、1,1′-双(二苯基膦)二茂铁络合物、1,2-双(二苯基膦)乙烷络合物、N-甲基咪唑络合物、2,2′-联吡啶络合物、(双环[2.2.1]-庚-2,5-二烯)络合物、双(二叔丁基(4-二甲氨基苯基)膦)络合物、双(叔丁基异氰酸酯)络合物、2-甲氧基乙醚醚络合物、乙二醇二甲醚络合物、1,2-二甲氧基乙烷络合物、双(1,3-二氨基-2-丙醇)络合物、双(N,N-二乙基乙二胺)络合物、1,2-二氨基环己烷络合物、吡啶络合物、2,2′:6′,2″-三联吡啶络合物、乙硫醚络合物、乙烯络合物、胺络合物;六氯钯(IV)酸钾、六氯钯(IV)酸钠、六氯钯(IV)酸铵、四氯钯(II)酸钾、四氯钯(II)酸钠、四氯钯(II)酸铵、三叔丁基膦溴化钯(I)二聚体、(2-甲基烯丙基)氯化钯(II)二聚体、双(二亚苄基丙酮)钯(0)、三(二亚苄基丙酮)二钯(0)、四(三苯基膦)钯(0)、四(三环己基膦)钯(0)、双[1,2-双(二苯基膦)乙烷]钯(0)、双(3,5,3′,5′-二甲氧基二亚苄基丙酮)钯(0)、双(三叔丁基膦)钯(0)、内消旋四苯基四苯并卟吩钯、四(甲基二苯基膦)钯(0)、三(3,3′,3″-次膦基-三(苯磺酸)钯(0)九钠盐、1,3-双(2,4,6-三甲基苯基)-咪唑-2-亚基(1,4-萘醌)钯(0)、1,3-双(2,6-二异丙基苯基)-咪唑-2-亚基(1,4-萘醌)钯(0)、和它们的氯仿络合物;
烯丙基氯化镍(II)二聚体、硫酸镍(II)铵、双(1,5-环辛二烯)镍(0)、双(三苯基膦)二羰基镍(0)、四(三苯基膦)镍(0)、四(三苯基亚磷酸)镍(0)、六氟镍(IV)酸钾、四氰基镍(II)酸钾、仲高碘酸镍(IV)钾、四溴镍(II)酸二锂,四氰基镍(II)酸钾;
氯化铂(IV)、氧化铂(IV)、硫化铂(IV)、六氯合铂(IV)酸钾、六氯合铂(IV)酸钠、六氯合铂(IV)酸铵、四氯合铂(II)酸钾、四氯合铂(II)酸铵、四氰基铂(II)酸钾、三甲基(甲基环戊二烯基)铂(IV)、顺式-二胺四氯合铂(IV)、三氯(乙烯基)铂(I I)酸钾、六羟基铂(IV)酸钠、四氨基铂(II)合四氯化铂(II)、六氯合铂(IV)酸四丁基铵、乙烯双(三苯基膦)铂(0)、铂(0)-1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷、铂(0)-2,4,6,8-四甲基-2,4,6,8-四乙烯基环四硅氧烷、四(三苯基膦)铂(0)、八乙基卟吩铂、氯铂酸、羰基铂;氯代双(乙烯)铑二聚体、六癸酰六铑、(1,5-环辛二烯)氯铑二聚体、(降冰片二烯)氯铑二聚体、(1,5-己二烯)氯铑二聚体。
配体优选是式(VI)的膦
PR11 3 (VI)
其中,基团R11彼此独立地表示氢,直链、支链或环状的C1-C20烷基,C1-C20烷基芳基,C2-C20烯基,C2-C20炔基,C1-C20羧酸酯基,C1-C20烷氧基,C1-C20烯基氧基,C1-C20炔基氧基,C2-C20烷氧羰基,C1-C20烷硫基,C1-C20烷基磺酰基,C1-C20烷基亚磺酰基,甲硅烷基和/或其衍生物,和/或被至少一个R12取代的苯基或被至少一个R12取代的萘基。R12彼此独立地表示氢,氟,氯,溴,碘,NH2,硝基,羟基,氰基,甲酰基,直链、支链或环状的C1-C20烷基,C1-C20烷氧基,HN(C1-C20烷基),N(C1-C20烷基)2,-CO2-(C1-C20烷基),-CON(C1-C20烷基)2,-OCO(C1-C20烷基),NHCO(C1-C20烷基),C1-C20酰基,-SO3M,-SO2N(R13)M,-CO2M,-PO3M2,-AsO3M2,-SiO2M,-C(CF3)2OM(M=H、Li、Na或K),其中R13表示氢,氟,氯,溴,碘,直链、支链或环状的C1-C20烷基,C2-C20烯基,C2-C20炔基,C1-C20羧酸酯基,C1-C20烷氧基,C1-C20烯基氧基,C1-C20炔基氧基,C2-C20烷氧羰基,C1-C20烷硫基,C1-C20烷基磺酰基,C1-C20烷基亚磺酰基,甲硅烷基和/或其衍生物,芳基,C1-C20芳烷基,C1-C20烷基芳基,苯基和/或联苯基。优选所有R11基团是相同的。
合适的膦(VI)例如是三甲基膦、三乙基膦、三丙基膦、三异丙基膦、三丁基膦、三异丁基膦、三异戊基膦、三己基膦、三环己基膦、三辛基膦、三癸基膦、三苯基膦、二苯基甲基膦、苯基二甲基膦、三(邻甲苯基)膦、三(对甲苯基)膦、乙基二苯基膦、二环己基苯基膦、2-吡啶基二苯基膦、双(6-甲基-2-吡啶基)苯基膦、三(对氯苯基)膦、三(对甲氧基苯基)膦、二苯基(2-磺酸基苯基)膦;二苯基(3-磺酸基苯基)膦的钾、钠、铵盐,双(4,6-二甲基-3-磺酸基苯基)(2,4-二甲基苯基)膦的钾、钠、铵盐,双(3-磺酸基苯基)苯基膦的钾、钠、铵盐,三(4,6-二甲基-3-磺酸基苯基)膦的钾、钠、铵盐,三(2-磺酸基苯基)膦的钾、钠、铵盐,三(3-磺酸基苯基)膦的钾、钠、铵盐;2-双(二苯基膦基乙基)三甲基碘化铵,2′-二环己基膦基-2,6-二甲氧基-3-磺酸基-1,1′-联苯钠盐,亚磷酸三甲酯和/或亚磷酸三苯酯。
特别优选地,配体是如下通式的双齿配体
R11 2M″-Z-M″R11 2 (VII)。
在该式中,M″彼此独立地代表N、P、As或Sb。优选地,两个M″相同,且特别优选M″表示磷原子。
每个R11基团彼此独立地代表式(VI)所描述的基团。优选所有R11基团是相同的。
Z优选是二价的桥联基团,其含有至少1个桥原子,其中优选含有2至6个桥原子。
桥原子可以选自C原子、N原子、O原子、Si原子和S原子。优选地,Z是含有至少一个碳原子的有机桥联基团。优选地,Z是含有1至6个桥原子的有机桥联基团,其中至少两个是碳原子,所述碳原子可以是未取代的或取代的。
优选的基团Z是-CH2-、-CH2-CH2-、-CH2-CH2-CH2-、-CH2-CH(CH3)-CH2-、-CH2-C(CH3)2-CH2-、-CH2-C(C2H5)-CH2-、-CH2-Si(CH3)2-CH2-、-CH2-O-CH2-、-CH2-CH2-CH2-CH2-、-CH2-CH(C2H5)-CH2-、-CH2-CH(n-Pr)-CH和-CH2-CH(n-Bu)-CH2-,未取代或取代的1,2-苯基、1,2-环己基、1,1′-二茂铁基或1,2-二茂铁基、2,2′-(1,1′-联苯基)、4,5-呫吨基和/或氧二-2,1-亚苯基。
合适的双齿膦配体(VII)例如是1,2-双(二甲基膦基)乙烷、1,2-双(二乙基膦基)乙烷、1,2-双(二丙基膦基)乙烷、1,2-双(二异丙基膦基)乙烷、1,2-双(二丁基膦基)乙烷、1,2-双(二叔丁基膦基)乙烷、1,2-双(二环己基膦基)乙烷和1,2-双(二苯基膦基)乙烷;1,3-双(二环己基膦基)丙烷、1,3-双(二异丙基膦基)丙烷、1,3-双(二叔丁基膦基)丙烷和1,3-双(二苯基膦基)丙烷;1,4-双(二异丙基膦基)丁烷和1,4-双(二苯基膦基)丁烷;1,5-双(二环己基膦基)戊烷;1,2-双(二叔丁基膦基)苯、1,2-双(二苯基膦基)苯、1,2-双(二环己基膦基)苯、1,2-双(二环戊基膦基)苯、1,3-双(二叔丁基膦基)苯、1,3-双(二苯基膦基)苯、1,3-双(二环己基膦基)苯和1,3-双(二环戊基膦基)苯;9,9-二甲基-4,5-双(二苯基膦基)呫吨、9,9-二甲基-4,5-双(二苯基膦基)-2,7-二叔丁基呫吨、9,9-二甲基-4,5-双(二叔丁基膦基)呫吨、1,1′-双(二苯基膦基)二茂铁、2,2′-双(二苯基膦基)-1,1′-联萘、2,2′-双(二对甲苯基膦基)-1,1′-联萘、(氧二-2,1-亚苯基)双(二苯基膦)、2,5-(二异丙基磷杂环戊烷基)苯、2,3-O-异丙叉基-2,3-二羟基-1,4-双(二苯基膦基)丁烷、2,2′-双(二叔丁基膦基)-1,1′-联苯、2,2′-双(二环己基膦基)-1,1′-联苯、2,2′-双(二苯基膦基)-1,1′-联苯、2-(二叔丁基膦基)-2′-(N,N-二甲氨基)联苯、2-(二环己基膦基)-2′-(N,N-二甲氨基)联苯、2-(二苯基膦基)-2′-(N,N-二甲氨基)联苯、2-(二苯基膦基)乙胺、2-[2-(二苯基膦基)乙基]吡啶;1,2-双(二-4-磺酸基苯基膦基)苯的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-4,4′,7,7′-四磺酸基-1,1′-联萘的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-5,5′-四磺酸基-1,1′-联苯的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-1,1′-联萘的钾、钠、铵盐,(2,2′-双[[双(3-磺酸基苯基)膦基]甲基]-1,1′-联苯的钾、钠、铵盐,9,9-二甲基-4,5-双(二苯基膦基)-2,7-磺酸基呫吨的钾、钠、铵盐,9,9-二甲基-4,5-双(二叔丁基膦基)-2,7-磺酸基呫吨的钾、钠、铵盐,1,2-双(二-4-磺酸基苯基膦基)苯的钾、钠、铵盐,内消旋-四(4-磺酸基苯基)卟吩的钾、钠、铵盐,内消旋-四(2,6-二氯-3-磺酸基苯基)卟吩的钾、钠、铵盐,内消旋-四(3-磺酸基均三甲苯基)卟吩的钾、钠、铵盐,四(4-羧基苯基)卟吩的钾、钠、铵盐和5,11,17,23-磺酸基-25,26,27,28-四羟基杯[4]芳烃的钾、钠、铵盐。
此外,式(VI)和(VII)的配体可以通过基团R11和/或桥联基团键合至合适的聚合物或无机基底。
催化剂体系具有1∶0.01至1∶100,优选1∶0.05至1∶10,且尤其是1∶1至1∶4的过渡金属-配体摩尔比。
优选地,方法步骤a)、b)和c)中的反应可选地在气氛中进行,所述气氛含有另外的气体成分,例如氮气、氧气、氩气、二氧化碳;温度为-20至340℃,尤其是20至180℃,且总压力为1至100巴。
在方法步骤a)、b)和c)之后,产物和/或组分和/或过渡金属和/或过渡金属化合物和/或催化剂体系和/或配体和/或反应物的分离可选地通过蒸馏或精馏、结晶或沉淀、过滤或离心、吸附或色谱法或者其它已知的方法来进行。
根据本发明,溶剂、助剂和任选的其它挥发性成分通过例如蒸馏、过滤和/或萃取而除去。
优选地,方法步骤a)、b)和c)中的反应可选地在吸收塔、喷塔、泡柱、搅拌釜、喷淋床发生器、流管、环管反应器和/或捏合机中进行。
合适的混合设备例如是锚式、桨式、MIG、螺旋桨、叶轮、涡轮、十字搅拌器,分散盘,空化(气化)搅拌器,转子-定子混合器,静态混合器,文丘里喷嘴和/或气密电动泵。
优选地,反应溶液/混合物经历这样的混合强度,其相当于旋转雷诺数为1至1,000,000,优选100至100,000。
优选地,各反应物料的强效搅拌在供能为0.080至10kW/m3,优选0.30至1.65kW/m3的条件下进行。
优选地,在反应期间,各催化剂A或B均相地和/或非均相地发挥作用。因此,各非均相作用的催化剂在反应期间以悬浮形式起作用或者键合至固相。
优选地,各催化剂A或B在反应之前和/或反应开始时和/或在反应期间原位生成。
优选地,各反应于溶剂中以单相体系在均相或非均相混合物中和/或在气相中进行。
如果使用多相体系,可以额外使用相转移催化剂。
根据本发明的反应可以在液相、气相或者超临界相中进行。在此,各催化剂A或B处于液体状态时优选以均相形式或作为悬浮液使用,而处于气相或超临界操作时,固定床设备是有利的。
合适的溶剂是水;醇,例如甲醇、乙醇、异丙醇、正丙醇、正丁醇、异丁醇、叔丁醇、正戊醇、异戊醇、叔戊醇、正己醇、正辛醇、异辛醇、正十三烷醇、苯甲醇等。进一步优选是二醇,例如乙二醇、1,2-丙二醇、1,3-丙二醇、1,3-丁二醇、1,4-丁二醇、二乙二醇等;脂肪烃,例如戊烷、己烷、庚烷、辛烷和石油醚、石脑油、石油、煤油、石蜡油等;芳香烃,例如苯、甲苯、二甲苯、均三甲苯、乙苯、二乙基苯等;卤代烃,例如二氯甲烷、氯仿、1,2-二氯乙烷、氯苯、四氯化碳、四溴乙烯等;脂环烃,例如环戊烷、环己烷和甲基环己烷等;醚,例如茴香醚(甲基苯基醚)、叔丁基甲基醚、二苄醚、乙醚、二氧六环、二苯醚、甲基乙烯基醚、四氢呋喃、三异丙基醚等;二醇醚,例如二乙二醇二乙醚、二乙二醇二甲醚(二甘醇二甲醚)、二乙二醇单丁醚、二乙二醇单甲醚、1,2-二甲氧基乙烷(DME,单甘醇二甲醚)、乙二醇单丁醚、三乙二醇二甲醚(三甘醇二甲醚)、三乙二醇单甲醚等;酮,例如丙酮、二异丁酮、甲基正丙基酮、甲基乙基酮、甲基异丁基酮等;酯,例如甲酸甲酯、乙酸甲酯、乙酸乙酯、乙酸正丙酯和乙酸正丁酯等;羧酸,例如甲酸、乙酸、丙酸、丁酸等;单独或混合使用。
合适的溶剂还有所使用的烯烃和次膦酸源。这提供高空-时产率形式的优点。
优选地,反应在烯烃和/或溶剂自身的蒸汽压下进行。
优选地,烯烃(IV)的R1、R2、R3、R4相同或不同,且彼此独立地表示H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和/或苯基。
优选地,也使用官能化的烯烃,诸如异硫氰酸烯丙酯、甲基丙烯酸烯丙酯、2-烯丙基苯酚、N-烯丙基硫脲、2-(烯丙基硫基)-2-噻唑啉、烯丙基三甲基硅烷、乙酸烯丙酯、乙酰乙酸烯丙酯、烯丙醇、烯丙胺、烯丙基苯、烯丙基腈、氰乙酸烯丙酯、烯丙基茴香醚、反式-2-戊烯醛、顺式-2-戊烯腈、1-戊烯-3-醇、4-戊烯-1-醇、4-戊烯-2-醇、反式-2-己烯醛、反式-2-己烯-1-醇、顺式-3-己烯-1-醇、5-己烯-1-醇、苯乙烯、-甲基苯乙烯、4-甲基苯乙烯、乙酸乙烯酯、9-乙烯基蒽、2-乙烯基吡啶、4-乙烯基吡啶和/或1-乙烯基-2-吡咯烷酮。
优选地,反应在0.01-100巴的烯烃分压下,特别优选在0.1-10巴的烯烃分压下进行。
优选地,以1∶10,000至1∶0.001的次膦酸-烯烃摩尔比进行反应,特别优选以1∶30至1∶0.01的比例进行。
优选地,以1∶1至1∶0.00000001的次膦酸-催化剂摩尔比进行反应,特别优选1∶0.01至1∶0.000001的次膦酸-催化剂摩尔比进行。
优选地,以1∶10,000至1∶0的次膦酸-溶剂摩尔比进行反应,特别优选以1∶50至1∶1的次膦酸-溶剂摩尔比进行。
一种根据本发明的用于制备式(II)化合物的方法的特征在于,将次膦酸源与烯烃在催化剂存在下反应并将产物(II)(烷基亚膦酸或烷基亚膦酸盐、烷基亚膦酸酯)从催化剂、过渡金属或过渡金属化合物、配体、络合剂、盐和副产物中分离。
根据本发明,催化剂、催化剂体系、过渡金属和/或过渡金属化合物通过加入助剂1分离,并通过萃取和/或过滤除去催化剂、催化剂体系、过渡金属和/或过渡金属化合物。
根据本发明,配体和/或络合剂通过用根据本发明的助剂2萃取和/或用根据本发明的助剂2蒸馏而分离。
助剂1优选是水和/或至少一个金属捕捉剂(金属清除剂)家族的成员。优选的金属捕捉剂是金属氧化物,诸如氧化铝、二氧化硅、二氧化钛、二氧化锆、氧化锌、氧化镍、氧化钒、氧化铬、氧化镁、硅藻土;金属碳酸盐,诸如碳酸钡、碳酸钙、碳酸锶;金属硫酸盐,诸如硫酸钡、硫酸钙、硫酸锶;金属磷酸盐,诸如磷酸铝、磷酸钒;金属碳化物,诸如碳化硅;金属铝酸盐,诸如铝酸钙;金属硅酸盐,诸如硅酸铝、白垩、沸石、膨润土、蒙脱石、锂蒙脱石;官能化的硅酸盐、官能化的硅胶,诸如QuadraSilTM;官能化的聚硅氧烷,诸如金属氮化物;炭;活性炭;莫来石;铝矾土;辉锑矿;白钨矿;钙钛矿;水滑石;官能化和未官能化的纤维素、壳聚糖、角蛋白、杂多阴离子;离子交换剂,诸如AmberliteTM、AmberjetTM、AmbersepTM、官能化的聚合物,诸如QuadraPureTM、聚合物键合的磷烷、磷烷氧化物、次膦酸盐、膦酸盐、磷酸盐、胺、铵盐、酰胺、硫代酰胺、脲、硫脲、三嗪、咪唑、吡唑、吡啶、嘧啶、吡嗪、硫醇、硫醚、硫醇酯、醇、烷氧化物、醚、酯、羧酸、乙酸酯、缩醛、肽、杂芳烯、聚乙烯亚胺/二氧化硅和/或树状大分子。
优选地,以相当于在助剂1上0.1~40重量%浓度的金属负载量添加助剂1。
优选地,在20-90℃的温度使用助剂1。
优选地,助剂1的停留时间是0.5-360分钟。
助剂2优选是上述的根据本发明的溶剂。
将单烯丙基官能化的二烷基次膦酸衍生物(III)或者烷基亚膦酸衍生物(II)以及次膦酸源(I)酯化成相应的酯可以例如通过与高沸点的醇经共沸蒸馏除去形成的水的条件下反应而实现,或者通过与环氧化物(氧化烯烃)反应而实现。
优选地,本文中在步骤a)之后,用通式为M-OH和/或M′-OH的醇,或者通过与氧化烯烃反应来将烷基亚膦酸(II)直接酯化,如下文所述。
优选地,M-OH是具有C1-C18的碳链长度的伯、仲或叔醇。特别优选是甲醇、乙醇、丙醇、异丙醇、正丁醇、2-丁醇、叔丁醇、戊醇和/或己醇。
优选地,M′-OH是乙二醇、1,2-丙二醇、1,3-丙二醇、1,4-丁二醇、2,2-二甲基-1,3-丙二醇、新戊二醇、1,6-己二醇、1,4-环己烷二甲醇、甘油、三羟甲基乙烷、三羟甲基丙烷、季戊四醇、山梨醇、甘露醇、α-萘酚、聚乙二醇、聚丙二醇和/或EO-PO嵌段聚合物。
作为M-OH和M′-OH,合适的还有一元或多元的、具有C1-C18的碳链长度的不饱和醇,如2-正丁烯-1-醇、1,4-丁烯二醇和烯丙醇。
作为M-OH和M′-OH,合适的还有一元醇与一个或多个氧化烯烃分子(优选与环氧乙烷和1,2-环氧丙烯)的反应产物。优选是2-甲氧基乙醇、2-乙氧基乙醇、2-正丁氧基乙醇、2-(2′-乙基-己氧基)-乙醇、2-正十二烷氧基乙醇、甲基二乙二醇、乙基二乙二醇、异丙基二乙二醇、脂肪醇聚乙二醇醚和芳基聚乙二醇醚。
优选地,M-OH和M′-OH还有多元醇与一个或多个氧化烯烃分子的反应产物,尤其是二乙二醇和三乙二醇,以及1至6分子环氧乙烷或环氧丙烷在甘油、三羟甲基丙烷或季戊四醇上的加合物。
作为M-OH和M′-OH,还可以使用水与一个或多个氧化烯烃分子的反应产物。优选是不同分子尺寸的具有100-1000g/mol,特别优选150-350g/mol的平均摩尔重量的聚乙二醇和聚-1,2-丙二醇。
作为M-OH和M′-OH,还优选是环氧乙烷与聚-1,2-丙二醇或脂肪醇丙二醇的反应产物;还有1,2-环氧丙烷与聚乙二醇或脂肪醇乙氧基化物的反应产物。优选是那些具有100-1000g/mol,特别优选150-450g/mol的平均摩尔重量的反应产物。
可用作M-OH和M′-OH的还有氧化烯烃与氨、伯胺或仲胺、硫化氢、硫醇、磷的含氧酸和C2-C6-二羧酸的反应产物。合适的环氧乙烷与含氮化合物的反应产物是三乙醇胺、甲基二乙醇胺、正丁基二乙醇胺、正十二烷基二乙醇胺、二甲基乙醇胺、正丁基甲基乙醇胺、二正丁基乙醇胺、正十二烷基甲基乙醇胺、四羟乙基乙二胺或五羟乙基二亚乙基三胺。
优选的氧化烯烃是环氧乙烷、1,2-环氧丙烷、1,2-环氧丁烷、1,2-环氧乙基苯、(2,3-环氧丙基)苯、2,3-环氧-1-丙醇和3,4-环氧-1-丁烯。
合适的溶剂是在方法步骤a)中提到的溶剂,且也可以是所使用的醇M-OH和M′-OH和氧化烯烃。这提供高空-时产率形式的优点。
优选地,反应在所使用的醇(M-OH和M′-OH)和氧化烯烃和/或溶剂的自身蒸汽压下进行。
优选地,反应在0.01-100巴的所使用的醇(M-OH和M′-OH)和氧化烯烃的分压下进行,特别优选在0.1-10巴的醇分压下进行。
优选地,反应在-20至340℃的温度下进行,特别优选在20至180℃的温度下进行。
优选地,反应在1至100巴的总压力下进行。
优选地,反应在醇成分或者氧化烯烃成分相对次膦酸源(I)或者烷基亚膦酸(II)或者单烯丙基官能化的二烷基次膦酸(III)的摩尔比为10,000∶1至0.001∶1的条件下进行,特别优选以1000∶1至0.01∶1的比例进行。
优选地,反应在次膦酸源(I)或者烷基亚膦酸(II)或者单烯丙基官能化的二烷基次膦酸(III)相对溶剂的摩尔比为1∶10,000至1∶0的条件下进行,特别优选以1∶50至1∶1的次膦酸-溶剂摩尔比进行。
用于方法步骤b)将烷基亚膦酸、其盐或酯(II)与烯丙基化合物(V)和碱反应成单烯丙基官能化的二烷基次膦酸、其盐或酯(III)的催化剂B可以优选是催化剂A。
优选地,碱是碱金属和/或碱土金属、碱金属和/或碱土金属氢化物、和/或碱金属和/或碱土金属醇化物、和/或碱金属和/或碱土金属氢氧化物,胺和/或二胺,和/或有机锂化合物。
优选的碱金属化合物和/或碱土金属化合物是锂、氢氧化锂、氢化锂、氢化锂铝、甲基锂、丁基锂、叔丁基锂、二异丙基氨基锂、钠、氢氧化钠、氢化钠、硼氢化钠、甲醇钠、乙醇钠或丁醇钠、氢氧化钾、甲醇钾、乙醇钾和/或丁醇钾。
优选的胺是氨、一元胺、二胺。
优选的一元胺是例如式R′-NH2的胺,其中R′表示直链或支链的C1-C20烷基。优选的是甲胺、乙胺、丙胺、异丙胺、丁胺、异丁胺、戊胺和2-乙基己胺、苯胺。
优选的二胺是例如式H2N-R″-NH2的胺,其中R″表示直链或支链的C1-C20烷基。优选的是乙二胺、丙二胺、二氨基丁烷、戊二胺和己二胺。
优选的碱还有作为质子海绵体已知的化合物,例如1,8-二氮杂双环[5.4.0]十一-7-烯、1,5,7-三氮杂双环[4.4.0]癸-5-烯、1,1,3,3-四甲基胍。
优选地,作为烯丙基化合物,使用3-氯-1-丙烯、3-氯-2-甲基-1-丙烯、3-氯-1-苯基-1-丙烯、1-氯-2-丁烯、1-氯-3-甲基-2-丁烯、3-溴-1-丙烯、3-溴-2-甲基-1-丙烯、3-溴-1-苯基-1-丙烯、1-溴-2-丁烯、1-溴-3-甲基-2-丁烯、乙酸烯丙酯、乙酸2-甲基烯丙酯。
优选地,基于所使用的烯丙基化合物(V),碱的份额为0.01至110mol-%。
优选地,反应在20至120℃的温度,特别优选在30至80℃的温度进行。
优选地,反应时间为0.1至20小时。
优选地,反应在烯丙基化合物(V)和/或溶剂自身的蒸汽压下进行。
用于方法步骤b)的合适的溶剂是上述在方法步骤a)中使用的那些。
优选地,反应在0.01-100巴,特别优选在0.1-10巴的烯丙基化合物(V)的分压下进行。
优选地,烯丙基化合物(V)相对烷基亚膦酸(II)的比例为2∶1至1∶1,特别优选1.1∶1至1∶1。
优选地,反应在1∶1至1∶0.00000001的烷基亚膦酸-催化剂摩尔比,特别优选以1∶0.25至1∶0.000001的烷基亚膦酸-催化剂摩尔比进行。
优选地,反应以1∶10,000至1∶0的烷基亚膦酸-溶剂摩尔比,特别优选以1∶50至1∶1的烷基亚膦酸-溶剂摩尔比进行。
单烯丙基官能化的二烷基次膦酸或其盐(III)可以随后反应成另外的金属盐。
优选地,方法步骤c)所使用的金属化合物是金属Mg、Ca、Al、Sb、Sn、Ge、Ti、Fe、Zr、Zn、Ce、Bi、Sr、Mn、Li、Na、K的化合物,特别优选的是Mg、Ca、Al、Ti、Zn、Sn、Ce、Fe的化合物。
用于方法步骤c)的合适的溶剂是上述在方法步骤a)中使用的那些。
优选地,方法步骤c)中的反应在水性介质中进行。
优选地,在方法步骤c)中,将根据方法步骤b)获得的单烯丙基官能化的二烷基次膦酸、其酯和/或碱金属盐(III)与Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物反应成这些金属的单烯丙基官能化的二烷基次膦酸盐(III)。
在此,以单烯丙基官能化的二烷基次膦酸/二烷基次膦酸酯/二烷基次膦酸盐(III)比金属的摩尔比为8比1至1比3(对于四价金属离子或具有稳定的四价氧化态的金属),6比1至1比3(对于三价金属离子或具有稳定的三价氧化态的金属),4比1至1比3(对于二价金属离子或具有稳定的二价氧化态的金属)和3比1至1比4(对于一价金属离子或具有稳定的一价氧化态的金属)进行反应。
优选地,将在方法步骤b)中获得的单烯丙基官能化的二烷基次膦酸酯/二烷基次膦酸盐(III)反应成相应的二烷基次膦酸,并在方法步骤c)中将其与Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物反应成这些金属的单烯丙基官能化的二烷基次膦酸盐(III)。
优选地,将在方法步骤b)中获得的单烯丙基官能化的二烷基次膦酸/二烷基次膦酸酯转化为二烷基次膦酸碱金属盐,并在步骤c)中将其与Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物反应成这些金属的单烯丙基官能化的二烷基次膦酸盐(III)。
优选地,用于方法步骤c)的Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的金属化合物是金属、金属氧化物、金属氢氧化物、氢氧化金属氧化物、金属硼酸盐、金属碳酸盐、金属碱式碳酸盐、金属碱式碳酸盐水合物、金属碱式碳酸混盐、金属碱式碳酸混盐水合物、金属磷酸盐、金属硫酸盐、金属硫酸盐水合物、金属碱式硫酸盐水合物、金属碱式硫酸混盐水合物、金属硫酸氧盐、金属乙酸盐、金属硝酸盐、金属氟化物、金属氟化物水合物、金属氯化物、金属氯化物水合物、金属氯氧化物、金属溴化物、金属碘化物、金属碘化物水合物、金属羧酸衍生物和/或金属烷氧化物。
优选地,金属化合物是氯化铝、氢氧化铝、硝酸铝、硫酸铝、硫酸氧钛、硝酸锌、氧化锌、氢氧化锌和/或硫酸锌。
合适的还有金属铝、氟化铝、羟铝基氯化物、溴化铝、碘化铝、硫化铝、硒化铝;磷化铝、次磷酸铝、锑化铝、氮化铝;碳化铝、六氟硅酸铝;氢化铝、氢化铝钙、硼氢化铝;氯酸铝;硫酸铝钠、硫酸铝钾、硫酸铝铵、硝酸铝、偏磷酸铝、磷酸铝、硅酸铝、硅酸镁铝、碳酸铝、铝水滑石、碳酸铝钠、硼酸铝;硫氰酸铝;氧化铝、铝酸,其相应的水合物和/或聚氢氧化铝化合物,其优选具有9至40重量%的铝含量。
合适的还有单、二、寡聚、多聚羧酸的铝盐,例如二乙酸铝、乙酰酒石酸铝、甲酸铝、乳酸铝、草酸铝、酒石酸铝、油酸铝、棕榈酸铝、硬脂酸铝、三氟甲磺酸铝、苯甲酸铝、水杨酸铝、8-氧代喹啉铝。
合适的还有元素锌、金属锌以及锌盐,例如卤化锌(氟化锌、氯化锌、溴化锌、碘化锌)。
合适的还有硼酸锌、碳酸锌、碱式碳酸锌、硅酸锌、六氟硅酸锌、锡酸锌、碱式锡酸锌、碱式碳酸铝镁锌;硝酸锌、亚硝酸锌、磷酸锌、焦磷酸锌;硫酸锌、磷化锌、硒化锌、碲化锌和第七主族的含氧酸的锌盐;(次卤酸盐;亚卤酸盐;卤酸盐,例如碘酸锌;高卤酸盐,例如高氯酸锌);拟卤素的锌盐(硫氰酸锌、氰酸锌、氰化锌);氧化锌、过氧化锌、氢氧化锌或混合的氢氧化锌氧化物。
优选的是过渡金属的含氧酸的锌盐(例如氢氧化铬(VI)酸锌、亚铬酸锌、钼酸锌、高锰酸锌、钼酸锌)。
合适的还有单、二、寡聚、多聚羧酸的锌盐,例如甲酸锌、乙酸锌、三氟乙酸锌、丙酸锌、丁酸锌、戊酸锌、辛酸锌、油酸锌、硬脂酸锌、草酸锌、酒石酸锌、柠檬酸锌、苯甲酸锌、水杨酸锌、乳酸锌、丙烯酸锌、马来酸锌、丁二酸锌,氨基酸(甘氨酸)的盐、酸性的羟基官能化盐(苯酚锌等),对苯酚磺酸锌、乙酰丙酮酸锌、锡酸锌、二甲基氨荒酸锌、三氟甲磺酸锌。
在钛化合物方面是金属钛以及钛(III)和/或(IV)的氯化物、硝酸盐、硫酸盐、甲酸盐、乙酸盐、溴化物、氟化物、氯氧化物、硫酸氧化物、氧化物、正丙氧化物、正丁氧化物、异丙氧化物、乙氧化物、2-乙基己氧化物。
合适的还有金属锡以及锡盐(氯化亚锡(II)和/或氯化锡(IV));氧化锡和烷氧化锡,诸如叔丁氧基锡(IV)。
合适的还有氟化铈(III)、氯化铈(III)、硝酸铈(III)。
在锆化合物方面,优选的是金属锆以及锆盐(诸如氯化锆、硫酸锆、乙酸氧锆、氯化氧锆)。进一步优选是氧化锆以及叔丁氧锆(IV)。
优选地,反应在0.1至70重量%,优选5至40重量%的单烯丙基官能化的二烷基次膦酸盐(III)固含量下进行。
优选地,方法步骤c)中的反应在20至250℃的温度,特别优选在80至120℃的温度进行。
优选地,方法步骤d)中的反应在介于0.01和1000巴的压力下,特别优选在0.1至100巴的压力下进行。
优选地,方法步骤d)中的反应在1×10-7至1×102h的反应时间内进行。
优选地,在方法步骤d)之后,将通过过滤和/或离心从反应混合物中分离单烯丙基官能化的二烷基次膦酸盐(III)进行干燥。
优选地,在方法步骤b)之后获得的产物混合物不经进一步纯化而与金属化合物反应。
优选的溶剂是在方法步骤a)中提到的溶剂。
优选地,方法步骤b)和/或c)的反应在通过步骤a)和/或b)提及的溶剂体系中进行。
优选地,方法步骤c)中的反应在改性的所提及的溶剂体系中。优选地,通过添加酸性成分、增溶剂、抑泡剂等对溶剂体系进行改性。
在所述方法的另一实施方式中,对在方法步骤a)和/或b)之后获得的产物混合物进行后处理。
在所述方法的另一实施方式中,对在方法步骤b)之后获得的产物混合物进行后处理,并随后将方法步骤b)之后获得的单烯丙基官能化的二烷基次膦酸和/或其盐或酯(III)在方法步骤c)中与金属化合物反应。
优选地,对在方法步骤b)之后的产物混合物进行后处理,其中分离单烯丙基官能化的二烷基次膦酸和/或其盐或酯(III)。在此,分离步骤通过除去溶剂体系进行,例如通过蒸发。
优选地,金属Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的单烯丙基官能化的二烷基次膦酸盐(III)可选地具有0.01至10重量%的残余水分,优选0.1至1重量%;0.1至2000μm的平均粒径,优选10至500μm;80至800g/l的容积密度,优选200至700g/L;根据Pfrengle的流动能力在0.5至10,优选1至5。
特别优选地,成型体、膜、丝和纤维含有5至30重量%的根据权利要求1至11中一项或多项所制备的单烯丙基官能化的二烷基次膦酸/二烷基次膦酸酯/二烷基次膦酸盐,5至90重量%的聚合物或它们的混合物,5至40重量%的添加剂和5至40重量%的填料,其中,各成分之和始终为100重量%。
优选的是阻燃剂,其包含0.1至90重量%的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐(III)以及0.1至50重量%的另外的添加剂。
优选地,添加剂是抗氧化剂、抗静电剂、发泡剂、另外的阻燃剂、热稳定剂、抗冲击改性剂、加工助剂、润滑剂、光稳定剂、抗滴落剂、增容剂、补强剂、填料、晶核形成剂、成核剂、用于激光标记的添加剂、水解稳定剂、链增长剂、涂料颜料、增塑剂和/或塑化剂。
本发明尤其涉及根据本发明的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐(III)作为阻燃剂的用途或者作为制备用于热塑性聚合物(如聚酯、聚苯乙烯或聚酰胺)和用于热固性聚合物(如不饱和聚酯树脂、环氧树脂、聚氨酯或丙烯酸酯)的阻燃剂的中间体的用途。
合适的聚酯衍生自二羧酸及其酯与二醇和/或衍生自羟基羧酸或相应的内酯。特别优选使用对苯二甲酸和乙二醇、1,3-丙二醇和1,3-丁二醇。
优选地,在聚酯制备时除了常用的催化剂外,还可以加入常规的添加剂(交联剂、消光剂和稳定剂、成核剂、染料和填料等)。
优选将根据本发明制备的阻燃聚酯模塑材料用于阻燃聚酯成型体中。
优选的聚合物成型体是丝、纤维、薄膜和成型体。
优选地,在由阻燃性聚合物制备的丝和纤维中最终的含磷量为0.1-18重量%,优选0.5-15重量%,在薄膜的情况下是0.2-15重量%,优选0.9-12重量%。
合适的聚酯衍生自二羧酸及其酯与二醇和/或源自羟基羧酸或相应的内酯。特别优选使用对苯二甲酸和乙二醇、1,3-丙二醇和1,3-丁二醇。
此外,合适的聚酯是聚对苯二甲酸乙二酯;聚对苯二甲酸丁二酯(Celanese公司的2500、2002;BASF公司的);聚-1,4-二羟甲基环己烷-对苯二甲酸酯;聚羟基苯甲酸酯;以及嵌段聚醚酯,其衍生自具有羟基端基的聚醚;此外还有用聚碳酸酯或MBS改性的聚酯。
合适的聚烯烃是例如单烯烃和二烯烃(例如乙烯、丙烯、异丁烯、丁烯、4-甲基戊烯、异戊二烯、丁二烯、苯乙烯)的聚合物,诸如聚丙烯;聚异丁烯;聚丁-1-烯;聚-4-甲基戊-1-烯;聚苯乙烯;聚对甲基苯乙烯和/或聚-α-甲基苯乙烯;聚异戊二烯或聚丁二烯;和聚乙烯(任选交联的),例如高密度聚乙烯(HDPE)、高分子量高密度聚乙烯(HDPE-HMW)、超高分子量高密度聚乙烯(HDPE-UHMW)、中密度聚乙烯(HMDPE)、低密度聚乙烯(LDPE)、线性低密度聚乙烯(LLDPE)、极低密度聚乙烯(VLDPE)、低密度支化聚乙烯(BLDPE);还有环烯烃的聚合物,例如环戊烯的或降冰片烯的聚合物。
上述聚烯烃,尤其是聚乙烯和聚丙烯,优选根据现有技术来制备,例如通过自由基聚合反应(通常在高压和高温下)或者通过过渡金属催化剂的催化聚合反应。
此外,优选的聚合物是上述聚烯烃的共混物(Blends),例如聚丙烯和聚异丁烯、聚乙烯和聚异丁烯、聚丙烯和聚乙烯(例如PP/HDPE/LDPE)和不同类型的聚乙烯的共混物(例如LDPE/HDPE)。
此外,优选的聚合物是单烯烃与二烯烃彼此之间的共聚物,和单烯烃和二烯烃与其他烯丙基单体的共聚物,例如乙烯-丙烯共聚物;LLDPE、VLDPE以及它们与LDPE的共混物;丙烯-丁-1-烯共聚物、丙烯-异丁烯共聚物、乙烯-丁-1-烯共聚物、乙基-己烯共聚物、乙烯-甲基戊烯共聚物、乙烯-庚烯共聚物、乙烯-辛烯共聚物、丙烯-丁二烯共聚物、异丁烯-异戊二烯共聚物、乙烯-丙烯酸烷基酯共聚物、乙烯-甲基丙烯酸烷基酯共聚物、乙烯-乙酸乙烯酯共聚物;苯乙烯或α-甲基苯乙烯与二烯或丙烯酸衍生物的共聚物,例如苯乙烯-丁二烯、苯乙烯-丙烯腈、苯乙烯-甲基丙烯酸烷基酯、苯乙烯-丁二烯-丙烯酸烷基酯和苯乙烯-丁二烯-甲基丙烯酸烷基酯、苯乙烯-马来酸酐、苯乙烯-丙烯腈-丙烯酸甲酯;由苯乙烯共聚物和另一种聚合物(例如聚丙烯酸酯、二烯聚合物或乙烯-丙烯-二烯三元共聚物)构成的高冲击韧性的共混物;以及苯乙烯类的嵌段共聚物,例如苯乙烯-丁二烯-苯乙烯、苯乙烯-异戊二烯-苯乙烯、苯乙烯-乙烯/丁烯-苯乙烯或苯乙烯-乙烯/丙烯-苯乙烯;还有苯乙烯或α-甲基苯乙烯的接枝共聚物,例如苯乙烯接枝到聚丁二烯上,苯乙烯接枝到聚丁二烯-苯乙烯共聚物或聚丁二烯-丙烯腈共聚物上,苯乙烯和丙烯腈(或甲基丙烯腈)接枝到聚丁二烯上;苯乙烯、丙烯腈和甲基丙烯酸甲酯接枝到聚丁二烯上;苯乙烯和马来酸酐接枝到聚丁二烯上;苯乙烯、丙烯腈和马来酸酐或马来酰亚胺接枝到聚丁二烯上;苯乙烯和马来酰亚胺接枝到聚丁二烯上、苯乙烯和丙烯酸烷基酯或甲基丙烯酸烷基酯接枝到聚丁二烯上;苯乙烯和丙烯腈接枝到乙烯-丙烯-二烯烃三元共聚物上,苯乙烯和丙烯腈接枝到聚丙烯酸烷基酯或聚甲基丙烯酸烷基酯上,苯乙烯和丙烯腈接枝到丙烯酸酯-丁二烯共聚物上,以及它们的共混物,例如作为所谓的ABS-、MBS-、ASA-或AES-聚合物已知的那些;还有它们与一氧化碳的共聚物或者乙烯-丙烯酸共聚物和它们的盐(离聚物),以及乙烯与丙烯和一种二烯(例如己二烯、二环戊二烯、亚乙基降冰片烯)的三元共聚物;和这样的共聚物彼此之间的共混物和/或上文提及的聚合物,例如聚丙烯-乙烯-丙烯共聚物,LDPE-乙烯-乙酸乙烯酯、LDPE-乙烯-丙烯酸共聚物、LLDPE-乙烯-乙酸乙烯酯共聚物、LLDPE-乙烯-丙烯酸共聚物,和交替的或无规的聚烯烃-一氧化碳共聚物的共混物以及它们与其他聚合物,例如聚酰胺的共混物。
优选地,聚合物是聚酰胺和共聚酰胺,其衍生自二胺与二羧酸和/或衍生自氨基羧酸或相应的内酰胺,诸如尼龙2.12,尼龙4,尼龙4.6,尼龙6,尼龙6.6,尼龙6.9,尼龙6.10,尼龙6.12,尼龙6.66,尼龙7.7,尼龙8.8,尼龙9.9,尼龙10.9,尼龙10.10,尼龙11,尼龙12,等等。这些聚酰胺例如以以下商品名是已知的:DuPont公司的BASF公司的DSM公司的K122、DuPont公司的7301、Bayer公司的B29和Ems Chemie公司的
合适的还有从间二甲苯、二胺和己二酸出发制备的芳香聚酰胺;由六亚甲基二胺和间苯二甲酸和/或对苯二甲酸和任选的作为改性剂的一种弹性体制备的聚酰胺,例如聚-2,4,4-三甲基六亚甲基-对苯二甲酰胺或聚-间亚苯基间苯二甲酰胺,上文提到的聚酰胺与聚烯烃、烯烃共聚物、离子聚合物或化学键合或接枝的弹性体,或者与聚醚(例如与聚乙二醇、聚丙二醇或聚丁二醇)形成的嵌段共聚物。此外还有经EPDM或ABS改性的聚酰胺或共聚酰胺;以及在处理过程中缩合的聚酰胺(“RIM聚酰胺体系”)。
根据权利要求1至11中一项或多项制备的单烯丙基官能化的二烷基次膦酸/二烷基次膦酸酯/二烷基次膦酸盐优选以模塑材料的形式使用,其进一步用于生产聚合物成型体。
特别优选地,所述阻燃性模塑材料含有5至30重量%的如权利要求1至11中一项或多项所制备的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸盐或二烷基次膦酸酯,5至90重量%的聚合物或它们的共混物,5至40重量%的添加剂和5至40重量%的填料,其中,各组分之和始终为100重量%。
本发明还涉及阻燃剂,其含有根据权利要求1至11中一项或多项制备的单烯丙基官能化的二烷基次膦酸、二烷基次膦酸盐或二烷基次膦酸酯。
此外,本发明涉及聚合物模塑材料及聚合物成型体、聚合物膜、聚合物丝和聚合物纤维,其含有根据本发明制备的金属Mg、Ca、Al、Zn、Ti、Sn、Zr、Ce或Fe的单烯丙基官能化的二烷基次膦酸盐。
本发明尤其涉及根据本发明制备的单烯丙基官能化的二烷基次膦酸盐作为阻燃剂用于热塑性聚合物(如聚酯、聚苯乙烯或聚酰胺)的用途和用于热固性聚合物(如不饱和聚酯树脂、环氧树脂、聚氨酯或丙烯酸酯)的阻燃剂的用途。
本发明尤其涉及根据本发明制备的单烯丙基官能化的二烷基次膦酸盐作为制备用于热塑性聚合物(如聚酯、聚苯乙烯或聚酰胺)和用于热固性聚合物(如不饱和聚酯树脂、环氧树脂、聚氨酯或丙烯酸酯)的阻燃剂的中间体的用途。
通过以下实施例阐释本发明。
阻燃性聚合物模塑材料和阻燃性聚合物成型体的制备、加工和测试
将阻燃成分与聚合物粒料及任选的添加剂混合,并在双螺杆挤出机上(型号Leistritz30/34)于230至260℃(PBT-GV)或260至280℃(PA66-GV)的温度加工。将均质化的聚合物束拔出,在水浴中冷却并随后造粒。
充分干燥后,将模塑材料在注塑机(型号Aarburg Allrounder)上于240至270℃(PBT-GV)或260至290℃(PA66-GV)的物料温度加工成试验样品。该试验样品根据UL94-测试法(UnderwriterLaboratories)针对抗火性(阻燃)进行测试并分级。
对由每一种混合物构成的测试样品测定消防等级UL 94(Underwriter Laboratories),在厚度1.5mm的测试样品上。
根据UL 94得到以下消防等级:
V-0:续燃时间不超过10秒,10次点火的总续燃时间不多于50秒,没有燃烧滴落,试样没有完全燃尽,点火结束后大于30秒无试样残炽;
V-1:点燃结束后续燃时间不超过30秒,10次点火的总续燃时间不超过250秒,点火结束后大于60秒无试样残炽,其余标准同V-0的情况;
V-2:通过燃烧滴落引燃棉絮,其余标准同V-1的情况;
不可分级的(nkl):不满足消防等级V-2。
此外,对一些被测试样品进行LOI值测量。LOI值(极限氧指数)根据ISO4589来确定。根据ISO4589,LOI对应于在氧气和氮气的混合物中恰能维持塑料燃烧的最低氧浓度的体积百分数。LOI值越高,被测材料越难燃。
LOI 23 可燃
LOI 24-28 有条件的可燃
LOI 29-35 阻燃
LOI>36 特别阻燃
所使用的化学试剂和缩略语
VE-水 完全去离子水
AIBN 偶氮二异丁腈,(Fa.WAKO Chemicals GmbH)
THF 四氢呋喃
WakoV65 2,2′-偶氮双(2,4-二甲基戊腈),(Fa.WAKO
Chemicals GmbH)
II 金属捕捉剂(Fa.Evonik Industries AG)
A 400-01 不饱和聚酯树脂(Fa.BASF)
Butanox M 50 甲基乙基酮过氧化物(Fa.Akzo Chemie GmbH)
NL-49 P 钴促进剂(Fa.Akzo Chemie GmbH)
实施例1
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置188g水并且在搅拌下通氮气脱气。然后在氮气氛下加入0.2mg硫酸钯(II)和2.3mg三(3-磺酸基苯基)膦三钠盐并搅拌,随后加入溶于66g水的66g次膦酸。将反应溶液转移到2L的Büchi反应器中并在搅拌和加压下输送乙烯,并将反应混合物升温至80℃。吸收28g乙烯后冷却并释放游离的乙烯。将反应混合物在旋转蒸发仪上脱除溶剂。向残余物中混入100g去离子水并于室温在氮气气氛中搅拌,然后过滤并用甲苯萃取滤液,之后在旋转蒸发仪上除去溶剂,并收集获得的乙基亚膦酸。如此获得92g(理论量的98%)乙基亚膦酸。
实施例2
如实施例1将99g次膦酸,396g丁醇,42g乙烯,6.9mg三(二亚苄基丙酮)二钯,9.5mg 4,5-双(二苯基膦基)-9,9-二甲基呫吨进行反应,然后通过用THP II装填的柱纯化并随后再次添加正丁醇。在80-110℃的反应温度通过共沸蒸馏除去形成的水。通过在减压下蒸馏纯化产物。产量:189g(理论量的84%)乙基亚膦酸丁酯。
实施例3
如实施例1将198g次膦酸,198g水,84g乙烯,6.1mg硫酸钯(II)和25.8mg 9,9-二甲基-4,5-双(二苯基膦基)-2,7-二磺酸基呫吨二钠盐进行反应,然后通过用THP II装填的柱纯化并随后添加正丁醇。在80-110℃的反应温度通过共沸蒸馏除去形成的水。通过在减压下蒸馏纯化产物。如此获得374g(理论量的83%)乙基亚膦酸丁酯。
实施例4
向装有气体导入管、温度计、强力搅拌器和具有气体焚烧装置的回流冷凝管的500ml五颈烧瓶中预置94g(1mol)乙基亚膦酸(如实施例1所制备)。于室温通入环氧乙烷。冷却下将反应温度调节至70℃并再在80℃继续反应一小时。环氧乙烷吸收量为65.7g。产物的酸值小于1mg KOH/g。产量:129g(理论量的94%)无色水样透明的产物(乙基亚膦酸2-羟乙酯)。
实施例5
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置400g乙醇,并且在搅拌下通氮气脱气。然后在氮气下加入1.35g(6mmol)乙酸钯和4.72g(18mmol)三苯基膦并搅拌,然后添加30g(0.2mol)乙基亚膦酸丁酯(如实施例2中制备)和26.3g(0.26mol)三乙胺并将反应混合物加热至80℃。随后滴加26.0g(0.26mol)乙酸烯丙酯。在5小时的反应时间之后,通过用THP II装填的柱纯化反应溶液并在真空中除去溶剂。通过柱色谱法纯化产物(乙基丙烯基次膦酸丁酯)。获得21.3g(理论量的56%)无色油状的乙基丙烯基次膦酸丁酯。
实施例6
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置400g甲苯,并且在搅拌下通氮气脱气。然后在氮气下加入30g(0.2mol)乙基亚膦酸丁酯(如实施例2中制备)和36.5g(0.24mol)1,8-二氮杂双环[5.4.0]十一碳-7-烯,并滴加29.0g(0.24mol)烯丙基溴。在5小时的反应时间之后,通过用THP II装填的柱纯化反应溶液并在真空中除去溶剂。通过柱色谱法纯化产物(乙基丙烯基次膦酸丁酯)。获得4.9g(理论量的13%)无色油状的乙基丙烯基次膦酸丁酯。
实施例7
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置400g甲苯,并且在搅拌下通氮气脱气。然后在氮气下加入3.27g(5mmol)双(三苯基膦)氯化镍和30g(0.2mol)乙基亚膦酸丁酯(如实施例3中制备)和36.5g(0.24mol)1,8-二氮杂双环[5.4.0]十一碳-7-烯并滴加29.0g(0.24mol)烯丙基溴。在5小时的反应时间之后,通过用THPII装填的柱纯化反应溶液并在真空中除去溶剂。通过柱色谱法纯化产物(乙基丙烯基次膦酸丁酯)。获得34.3g(理论量的90%)无色油状的乙基丙烯基次膦酸丁酯。
实施例8
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置400g乙醇,并且在搅拌下通氮气脱气。然后在氮气下加入30g(0.2mol)乙基亚膦酸丁酯(如实施例3中制备),并首先滴加在乙醇中的14.5g(0.25mol)甲醇钠,且随后滴加19.1g(0.25mol)烯丙基氯。在5小时的反应时间之后,通过用THP II装填的柱纯化反应溶液并在真空中除去溶剂。通过柱色谱法纯化产物(乙基丙烯基次膦酸丁酯)。获得9.9g(理论量的26%)无色油状的乙基丙烯基次膦酸丁酯。
实施例9
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置400g乙醇,并且在搅拌下通氮气脱气。然后在氮气下加入3.27g(5mmol)双(三苯基膦)氯化镍和30g(0.2mol)乙基亚膦酸丁酯(如实施例2中制备)并首先滴加在乙醇中的14.5g(0.25mol)甲醇钠,且随后滴加19.1g(0.25mol)烯丙基氯。在5小时的反应时间之后,通过用THPII装填的柱纯化反应溶液并在真空中除去溶剂。通过柱色谱法纯化产物。获得25.1g(理论量的66%)无色油状的乙基丙烯基次膦酸丁酯。
实施例10
在室温下,向配有搅拌器和强效冷凝器的三颈烧瓶中预置400g甲苯,并且在搅拌下通氮气脱气。然后在氮气下加入6.65g(6mmol)四(三苯基膦)合镍和30g(0.2mol)乙基亚膦酸丁酯(如实施例2中制备)和30.4g(0.2mol)1,8-二氮杂双环[5.4.0]十一碳-7-烯,并滴加20.9g(0.2mol)1-氯-3-甲基-2-丁烯。在5小时的反应时间之后,通过用THP II装填的柱纯化反应溶液并在真空中除去溶剂。通过柱色谱法纯化产物。获得33.1g(理论量的76%)无色油状的乙基(3-甲基-2丁烯基)次膦酸丁酯。
实施例11
向570g(3.0mol)乙基丙烯基次膦酸丁酯(如实施例6中制备)中加入248g(4mol)乙二醇和0.4g草酸钛钾并在100℃搅拌2h。通过缓慢地抽真空蒸出挥发性组分获得506g(理论量的98%)乙基丙烯基次膦酸2-羟乙酯。
实施例12
在搅拌反应器中预置150g丁醇,65g水,150g(3.75mol)氢氧化钠和237.5g(1.25mol)乙基丙烯基次膦酸丁酯(如实施例5中制备)。将该混合物在充分搅拌下加热至约80℃并在该温度下反应8小时。随后加入250ml水,并通过蒸馏将丁醇从反应混合物中除去。在添加另外的500ml水之后,通过添加大约184g(1.88mol)浓硫酸中和混合物。随后在真空中蒸馏出水。将残余物混入四氢呋喃中并萃取。真空中除去溶剂。获得266g(理论量的99%)油状乙基丙烯基次膦酸。
实施例13
将804g(6mol)乙基丙烯基次膦酸(如实施例12中制备)溶于860g水,并预置于装有温度计、回流冷凝管、强效搅拌器和滴液漏斗的5l五颈烧瓶中,并用约480g(6mol)50%浓度的氢氧化钠溶液中和。于85℃加入1291g的46%浓度的Al2(SO4)3·14H2O水溶液混合物。随后滤出获得的固体,用热水洗涤并在真空中于130℃干燥。产量:801g(理论量的94%)无色盐状乙基丙烯基次膦酸铝(III)盐。
实施例14
将134g(1mol)乙基丙烯基次膦酸(如实施例12中制备)和85g钛酸四丁酯在500ml甲苯中加热回流40小时。与此同时将产生的丁醇与部分甲苯不时地蒸出。随后将产生的溶液除去溶剂。获得133g(理论量的92%)乙基丙烯基次膦酸钛盐。
实施例15
将0.5份NL-49P与55份乙基丙烯基次膦酸丁酯(如实施例9中制备)混合,并在均质化之后通过添加2份Butanox M-50开始固化。获得磷含量为15.6重量%的聚合物。
实施例16
将35份苯乙烯与0.5份NL-49P混合,添加55份乙基乙烯基次膦酸丁酯(如实施例7中制备),并在均质化之后通过添加2份Butanox M-50开始固化。获得磷含量为9.7重量%的聚合物。LOI为35,未处理的苯乙烯为19。
实施例17
将100份不饱和聚酯树脂A 400-01与0.5份NL-49 P混合,加入55份乙基丙烯基次膦酸丁酯(如实施例5中制备)并在均质化之后通过添加2份Butanox M-50开始固化。
在加热的压力机中,在分隔薄膜和钢制框架上放入单位面积重量为450g/m2的两层连续纺织玻璃毡。随后,将约一半的树脂均匀分散。在添加另一层玻璃毡之后分散剩余的树脂,用分隔薄膜覆盖该层压材料,并在50℃的温度下于一小时内在10巴的挤压压力制成4mm厚的压紧的板。
获得磷含量为5.7重量%的层压材料。测定UL-94等级为V-0。LOI为34,未处理的层压材料为21。
实施例18
将50重量%的聚对苯二甲酸丁二酯、20重量%的乙基丙烯基次膦酸铝(III)盐(如实施例13中制备)和30重量%的玻璃纤维的混合物在双螺杆挤出机上(型号为Leistritz LSM 30/34)于230至260℃的温度混合成聚合物模塑材料。将均质化的聚合物束拔出,在水浴中冷却并随后造粒。
干燥后将模塑材料在注塑机上(型号:Aarburg Allrounder)于240至270℃加工成聚合物模制品并测定UL-94等级为V-0。
实施例19
将53重量%的尼龙6.6、30重量%的玻璃纤维、17重量%的乙基丙烯基次膦酸钛盐(如实施例14中制备)组成的混合物在双螺杆挤出机上(型号为Leistritz LSM 30/34)混合成聚合物模塑材料。将均质化的聚合物束拔出,在水浴中冷却并随后造粒。
干燥后将模塑材料在注塑机上(型号:Aarburg Allrounder)于260至290℃加工成聚合物模制品,并得出UL-94等级为V-0。
Claims (4)
1.利用烯丙基化合物制备单烯丙基官能化的二烷基次膦酸、二烷基次膦酸酯和二烷基次膦酸盐的方法,其特征在于,
a)使次膦酸源(I)
与烯烃(IV)
在催化剂A的存在下反应成烷基亚膦酸、其盐或酯(II)
b)使如此获得的烷基亚膦酸、其盐或酯(II)与式(V)的烯丙基化合物
在催化剂B和碱的存在下反应成单烯丙基官能化的二烷基次膦酸衍生物(III)
其中,R1、R2、R3、R4、R5、R6、R7、R8、R9相同或不同,且彼此独立地表示H、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基和/或苯基;和X表示H、Ca、Mg、Al、Zn、Ti、Fe、Ce、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、苯基、乙二醇、丙基乙二醇、丁基乙二醇、戊基乙二醇、己基乙二醇、烯丙基和/或甘油;和Y表示卤素或乙酸酯;和催化剂A和B是包含铑、镍、钯、铂和/或钌的过渡金属和/或过渡金属化合物。
2.根据权利要求1的方法,其特征在于,将步骤b)之后获得的单烯丙基官能化的二烷基次膦酸、其盐或酯(III)随后在步骤c)中与Mg、Ca、Al、Ti、Fe、Zn、Ce的金属化合物反应生成这些金属相应的单烯丙基官能化的二烷基次膦酸盐。
3.根据权利要求1或2的方法,其特征在于,烯丙基化合物是3-氯-1-丙烯、3-氯-2-甲基-1-丙烯、3-氯-1-苯基-1-丙烯、1-氯-2-丁烯、1-氯-3-甲基-2-丁烯、3-溴-1-丙烯、3-溴-2-甲基-1-丙烯、3-溴-1-苯基-1-丙烯、1-溴-2-丁烯、1-溴-3-甲基-2-丁烯、乙酸烯丙酯、乙酸2-甲基烯丙酯。
4.根据权利要求1或2的方法,其特征在于,碱是碱金属和/或碱土金属,碱金属和/或碱土金属氢化物,和/或碱金属和/或碱土金属醇化物,和/或碱金属和/或碱土金属氢氧化物,胺和/或二胺,和/或有机锂化合物。
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US (1) | US8772519B2 (zh) |
EP (1) | EP2367835B1 (zh) |
JP (1) | JP5743219B2 (zh) |
CN (1) | CN102171226B (zh) |
ES (1) | ES2446305T3 (zh) |
WO (1) | WO2010054722A1 (zh) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9139714B2 (en) * | 2008-11-05 | 2015-09-22 | Clariant Finance (Bvi) Limited | Method for producing dialkylphosphinic acids and esters and salts thereof by means of allyl alcohols-acroleins and use thereof |
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 |
DE102008056339A1 (de) * | 2008-11-07 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von mono-aminofunktionalisierten Dialkylphosphinsäuren, -estern und -salzen 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 |
CN102186864A (zh) * | 2008-11-07 | 2011-09-14 | 科莱恩金融(Bvi)有限公司 | 利用丙烯酸衍生物制备二烷基次膦酸、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 |
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 |
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 |
DE102008060535A1 (de) | 2008-12-04 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylether und ihre Verwendung |
CN103724372B (zh) | 2008-12-18 | 2017-03-01 | 科莱恩金融(Bvi)有限公司 | 亚乙基二烷基次膦酸、亚乙基二烷基次膦酸酯和亚乙基二烷基次膦酸盐的用途 |
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 |
DE102008063642A1 (de) | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monocarboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Alkylenoxiden und ihre Verwendung |
DE102008063627A1 (de) | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monohydroxyfunktionalisierten Dialkylphosphinsäuren,-estern und -salzen mittels Ethylenoxid und ihre Verwendung |
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 |
DE102008064003A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von mono-funktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
CN103172668A (zh) * | 2013-03-04 | 2013-06-26 | 广州金凯新材料有限公司 | 一种单烷基/二烷基次膦酸盐及其制备方法 |
CN104949967B (zh) * | 2015-06-09 | 2016-08-24 | 杭州欣叶生物科技有限公司 | 检测人体尿液中酪氨酸类酚代谢物的试剂盒 |
DE102015223432A1 (de) * | 2015-11-26 | 2017-06-01 | Clariant International Ltd | Polymere Flammschutzmittelmischungen |
US11420196B2 (en) * | 2018-09-27 | 2022-08-23 | Chevron Phillips Chemical Company Lp | Processes for producing fluorided solid oxides and uses thereof in metallocene-based catalyst systems |
Family Cites Families (85)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL292604A (zh) | 1962-05-12 | |||
US3345432A (en) | 1963-08-19 | 1967-10-03 | American Cyanamid Co | Flame-retardant compositions containing organophosphonic acids |
US3784638A (en) | 1969-12-24 | 1974-01-08 | Polaroid Corp | Preparation of tertiary organo-phosphine oxides |
DE2236037C3 (de) | 1972-07-22 | 1975-04-17 | Farbwerke Hoechst Ag Vormals Meister Lucius & Bruening, 6000 Frankfurt | Schwer entflammbare Fäden und Fasern aus Polyester |
DE2236036C3 (de) | 1972-07-22 | 1982-02-04 | Hoechst Ag, 6000 Frankfurt | Diphosphinsäureester |
DE2242002C3 (de) | 1972-08-26 | 1978-08-24 | Hoechst Ag, 6000 Frankfurt | Flammwidrige synthetische lineare Polyester sowie deren Verwendung |
DE2302523C3 (de) | 1973-01-19 | 1982-04-08 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Äthan-1,2-diphosphinsäurediestern |
US4001352A (en) | 1973-01-19 | 1977-01-04 | Hoechst Aktiengesellschaft | Process for the preparation of ethane-1,2-diphosphinic acid diesters |
DE2313581A1 (de) | 1973-03-19 | 1974-09-26 | Hoechst Ag | Verfahren zur herstellung von aethan1,2-diphosphinsaeurediestern |
DE2344332C3 (de) | 1973-09-03 | 1981-11-26 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von Vinylphosphinsäuren |
DE2346787C3 (de) | 1973-09-17 | 1980-05-08 | Hoechst Ag, 6000 Frankfurt | Schwer entflammbare lineare Polyester, Verfahren zu deren Herstellung und deren Verwendung |
DE2441878B2 (de) | 1974-08-31 | 1976-07-01 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von phosphon- und phosphinsaeuren |
DE2441783B2 (de) | 1974-08-31 | 1976-09-09 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von phosphon- und phosphinsaeuren |
GB1491608A (en) | 1975-05-28 | 1977-11-09 | Ici Ltd | Metal complex formazan dyestuffs and processes for their preparation |
US4235991A (en) | 1978-12-04 | 1980-11-25 | Occidental Research Corporation | Layered sulfonate end terminated organophosphorus inorganic polymers |
US4168267A (en) | 1978-10-23 | 1979-09-18 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl prolines |
US4337201A (en) | 1980-12-04 | 1982-06-29 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted prolines |
US4374131A (en) | 1981-04-27 | 1983-02-15 | E. R. Squibb & Sons, Inc. | Amino and substituted amino phosphinyl-alkanoyl compounds |
US4381297A (en) | 1981-05-04 | 1983-04-26 | E. R. Squibb & Sons, Inc. | Substituted carbonyl phosphinyl-alkanoyl compounds |
US4555506A (en) | 1981-12-24 | 1985-11-26 | E. R. Squibb & Sons, Inc. | Phosphorus containing compounds and use as hypotensives |
US4427665A (en) | 1982-05-19 | 1984-01-24 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted imino acids and their use in hypotensive compositions |
US4602092A (en) | 1983-09-19 | 1986-07-22 | E. R. Squibb & Sons, Inc. | Method for making phosphinic acid intermediates |
US4594199A (en) | 1983-09-19 | 1986-06-10 | E. R. Squibb & Sons, Inc. | Method for making phosphinic acid intermediates |
US4634689A (en) | 1985-10-31 | 1987-01-06 | Schering Corporation | Phosphinylalkanoyl imino acids |
GB8728483D0 (en) | 1987-12-04 | 1988-01-13 | Ciba Geigy Ag | Chemical compounds |
US5190934A (en) | 1989-06-03 | 1993-03-02 | Ciba-Geigy Corporation | P-subsituted propane-phosphinic acid compounds |
JPH03275742A (ja) * | 1990-03-23 | 1991-12-06 | Sekisui Chem Co Ltd | 自己消火性ポリオレフィン系連続気泡発泡体の製造方法 |
JPH03275743A (ja) * | 1990-03-23 | 1991-12-06 | Sekisui Chem Co Ltd | 自己消火性ポリオレフィン系連続気泡発泡体の製造方法 |
IL98502A (en) | 1990-06-22 | 1998-04-05 | Ciba Geigy Ag | History of Aminoalkene Phosphine Acid, Process for Their Preparation and Pharmaceutical Preparations Containing Them |
US5153347A (en) | 1991-01-31 | 1992-10-06 | E. R. Squibb & Sons, Inc. | Phosphonate, phosphinate derivatives useful as antihypertensive agents |
JP3109228B2 (ja) | 1992-02-25 | 2000-11-13 | 東洋紡績株式会社 | ホスフィニルカルボン酸又はその誘導体の製造方法 |
US5391743A (en) | 1992-05-29 | 1995-02-21 | Procter & Gamble Pharmaceuticals, Inc. | Quaternary nitrogen-containing phosphonate compounds, pharmaceutical compositions, and methods of treating abnormal calcium and phosphate metabolism and methods of treating and preventing dental calculus and plaque |
ZA938019B (en) | 1992-11-13 | 1995-04-28 | Upjohn Co | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses |
IT1270260B (it) | 1994-06-21 | 1997-04-29 | Zambon Spa | Derivati dell'acido fosfonico ad attivita' inibitrice delle metallopeptidasi |
DE4430932A1 (de) | 1994-08-31 | 1996-03-07 | Hoechst Ag | Flammgeschützte Polyesterformmasse |
US6384022B1 (en) | 1996-06-17 | 2002-05-07 | Guilford Pharmaceuticals Inc. | Prodrugs of NAALAdase inhibitors |
ES2177991T3 (es) | 1996-07-03 | 2002-12-16 | Baxter Int | Procedimiento para el ensamblado de un elemento cilindrico entre elementos planares. |
WO1999006062A1 (en) | 1997-08-04 | 1999-02-11 | Eli Lilly And Company | Cyclic peptide antifungal agents |
ES2209246T3 (es) * | 1997-11-28 | 2004-06-16 | Clariant Gmbh | Procedimiento para la fabricacion de sales de acidos dialquilfosfinicos. |
DE19851768C2 (de) * | 1997-11-28 | 2000-03-23 | Clariant Gmbh | Verfahren zur Herstellung von Dialkylphosphinsäuresalzen |
JP4224209B2 (ja) * | 1997-11-28 | 2009-02-12 | クラリアント・プロドゥクテ・(ドイチュラント)・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | 元素状燐のアルキル化法 |
AU2266899A (en) * | 1997-11-28 | 1999-06-16 | Clariant Gmbh | Method for producing dialkylphosphinic acids |
US6214812B1 (en) | 1998-04-02 | 2001-04-10 | Mbc Research, Inc. | Bisphosphonate conjugates and methods of making and using the same |
DE19828863C1 (de) | 1998-06-29 | 1999-09-02 | Clariant Gmbh | Verfahren zur Herstellung von Phosphinsäureestern und deren Verwendung |
DE19912920C2 (de) | 1999-03-22 | 2001-06-21 | Clariant Gmbh | Polymere Phosphinsäuren und deren Salze |
SE9904508D0 (sv) | 1999-12-09 | 1999-12-09 | Astra Ab | New compounds |
JP4666422B2 (ja) * | 2000-05-19 | 2011-04-06 | 三光株式会社 | 有機リン化合物の製造方法 |
US7135583B2 (en) | 2001-02-14 | 2006-11-14 | Japan Science And Technology Corporation | Process for preparation of alkenylphosphine oxides or alkenylphosphinic esters |
US20020187977A1 (en) * | 2001-03-15 | 2002-12-12 | Rodney Pearlman | Methods for restoring cognitive function following systemic stress |
DE10153780C1 (de) | 2001-11-02 | 2002-11-28 | Clariant Gmbh | Verfahren zur Herstellung von Carboxyethylmethylphosphinsäureglykolester und ihre Verwendung |
DE10333042B4 (de) | 2003-07-21 | 2005-09-29 | Clariant Gmbh | Verfahren zur Herstellung von cyclischen Phosphonsäureanhydriden und deren Verwendung |
US20070194479A1 (en) | 2003-12-09 | 2007-08-23 | Maki Sato | Thermoplastic Resin Composition For Masterbatches, Method Of Producing Molding Material Thereof, And Thermoplastic Resin Composition Using Them And Method Of Production Thereof |
US20050187196A1 (en) | 2004-02-23 | 2005-08-25 | Saegis Pharmaceuticals, Inc. | Treatment of attention disorders |
DE102004023085A1 (de) | 2004-05-11 | 2005-12-15 | Clariant Gmbh | Dialkylphosphinsäure-Salze, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
JP4517235B2 (ja) * | 2004-12-06 | 2010-08-04 | ナガセケムテックス株式会社 | β,γ−不飽和ホスフィン酸エステルの製造方法 |
US8030350B2 (en) | 2005-02-24 | 2011-10-04 | Diffusion Pharmaceuticals Llc | Trans carotenoids, their synthesis, formulation and uses |
DE102006010352A1 (de) | 2006-03-07 | 2007-09-13 | Clariant International Limited | Mischungen aus Mono-Carboxylfunktionalisierten Dialkylphosphinsäure-Salzen und weiteren Komponenten, ein Verfahren zu ihrer Herstellung und Verwendung |
DE102006010361A1 (de) | 2006-03-07 | 2007-09-13 | Clariant International Limited | Mischungen aus Mono-Carboxylfunktionalisierten Dialkylphosphinsäureestern und weiteren Komponenten |
DE102006010362A1 (de) | 2006-03-07 | 2007-09-13 | Clariant International Limited | Mischungen aus Mono-Carboxylfunktionalisierten Dialkylphosphinsäuren, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
WO2008033572A1 (en) | 2006-09-15 | 2008-03-20 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs, methods of synthesis and use |
DE102006045814A1 (de) | 2006-09-28 | 2008-04-03 | Clariant International Limited | Unsymmetrisch substituierte Phosphinsäuren |
DE102006048698A1 (de) | 2006-10-14 | 2008-04-17 | Clariant International Limited | Ethylendiphosphinsäuren |
DE102008039704A1 (de) | 2008-08-26 | 2010-03-04 | Tyco Electronics Amp Gmbh | Kontaktanordnung mit gebogener Litze, Relais mit Kontaktanordnung und Verfahren zur Montage eines Relais |
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 |
US9139714B2 (en) | 2008-11-05 | 2015-09-22 | Clariant Finance (Bvi) Limited | Method for producing dialkylphosphinic acids and esters and salts thereof by means of allyl alcohols-acroleins and use thereof |
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 |
DE102008056234A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Ltd. | Verfahren zur Herstellung von momo-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylen/Nitrilen und ihre Verwendung |
US20110213062A1 (en) * | 2008-11-06 | 2011-09-01 | Clariant Finance (Bvi) Limited | Method for Producing Mono-Hydroxyfunctionalized Dialkyphosphinic Acids and Esters and Salts Thereof and Use Thereof |
DE102008056235A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von monovinylfunktionalisierten Dialkylphosphinsäuren, deren Salze und Ester und ihre Verwendung |
DE102008056228A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von monoaminofunktionalisierten Dialkylphosphinsäuren, deren Salze und Ester und ihre Verwendung |
DE102008056227A1 (de) * | 2008-11-06 | 2010-05-12 | Clariant International Limited | Verfahren zur Herstellung von Dialkylphosphinsäuren, -estern und -salzen mittels Vinylverbindungen 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 |
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 |
CN102186864A (zh) * | 2008-11-07 | 2011-09-14 | 科莱恩金融(Bvi)有限公司 | 利用丙烯酸衍生物制备二烷基次膦酸、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 |
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 |
DE102008060535A1 (de) * | 2008-12-04 | 2010-06-10 | Clariant International Limited | Verfahren zur Herstellung von mono-carboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Vinylether und ihre Verwendung |
CN103724372B (zh) | 2008-12-18 | 2017-03-01 | 科莱恩金融(Bvi)有限公司 | 亚乙基二烷基次膦酸、亚乙基二烷基次膦酸酯和亚乙基二烷基次膦酸盐的用途 |
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 |
DE102008063642A1 (de) | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monocarboxyfunktionalisierten Dialkylphosphinsäuren, -estern und -salzen mittels Alkylenoxiden und ihre Verwendung |
DE102008063627A1 (de) * | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von monohydroxyfunktionalisierten Dialkylphosphinsäuren,-estern und -salzen mittels Ethylenoxid und ihre Verwendung |
DE102008063640A1 (de) | 2008-12-18 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von gemischtsubstituierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
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 |
DE102008064003A1 (de) | 2008-12-19 | 2010-06-24 | Clariant International Limited | Verfahren zur Herstellung von mono-funktionalisierten Dialkylphosphinsäuren, -estern und -salzen und ihre Verwendung |
-
2009
- 2009-10-06 CN CN200980138622.8A patent/CN102171226B/zh not_active Expired - Fee Related
- 2009-10-06 US US13/127,110 patent/US8772519B2/en not_active Expired - Fee Related
- 2009-10-06 ES ES09736567.0T patent/ES2446305T3/es active Active
- 2009-10-06 EP EP09736567.0A patent/EP2367835B1/de not_active Not-in-force
- 2009-10-06 JP JP2011535021A patent/JP5743219B2/ja not_active Expired - Fee Related
- 2009-10-06 WO PCT/EP2009/007135 patent/WO2010054722A1/de active Application Filing
Non-Patent Citations (6)
Title |
---|
A novel approach to phosphonic acids from hypophosphorous acids;Karla Bravo-Altamirano et al.;《Tetrahedron Lett.》;20070623;第48卷(第33期);5755-5759 * |
Environmentally Benign Synthesis of H-Phosphinic Acids Using a Water-Tolerant,Recyclable Polymer-Supported Catalyst;Sylvine Deprèle et al.;《Org.Lett.》;20040918;第6卷(第21期);3805-3808 * |
Palladium-Catalyzed Hydrophosphinylation of Alkenes and Alkynes;Sylvine Deprèle et al.;《J.Am.Chem.Soc.》;20020719;第124卷(第32期);9386-9387 * |
Palladium-Catalyzed Reactions of Hypophosphorous Compounds with Allenes,Dienes,and Allylic Electrophiles: Methodology for the Synthesis of Allylic H-Phosphinates;Karla Bravo-Altamirano,et al.;《J.Org.Chem.》;20080215;第73卷(第6期);2292-2301 * |
Phosphinic Acid Pseudopeptides Analogous to Glutamyl-γ-glutamate: Synthesis and Coupling to Pteroyl Azides Leads to Potent Inhibitors of Folylpoly-γ-glutamate Synthetase;Nadya Valiaeva,et al.;《J.Org.Chem.》;20010627;第66卷(第15期);5146-5154 * |
Recent adveances in phosphorus-carbon bond formation: synthesis of H-phosphinic acid derivatives from hypophosphorous compounds;Jean-Luc Montchamp;《Journal of Organometallic Chemistry》;20041111;第690卷(第10期);2388-2406 * |
Also Published As
Publication number | Publication date |
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EP2367835B1 (de) | 2013-12-11 |
JP2012508200A (ja) | 2012-04-05 |
US8772519B2 (en) | 2014-07-08 |
EP2367835A1 (de) | 2011-09-28 |
CN102171226A (zh) | 2011-08-31 |
JP5743219B2 (ja) | 2015-07-01 |
ES2446305T3 (es) | 2014-03-07 |
WO2010054722A1 (de) | 2010-05-20 |
US20110213080A1 (en) | 2011-09-01 |
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