JP2010533133A - アルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、それらの製造方法及び使用 - Google Patents
アルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、それらの製造方法及び使用 Download PDFInfo
- Publication number
- JP2010533133A JP2010533133A JP2010515387A JP2010515387A JP2010533133A JP 2010533133 A JP2010533133 A JP 2010533133A JP 2010515387 A JP2010515387 A JP 2010515387A JP 2010515387 A JP2010515387 A JP 2010515387A JP 2010533133 A JP2010533133 A JP 2010533133A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- acid
- salt
- bis
- catalyst
- 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.)
- Granted
Links
- -1 Alkyl phosphonous acid Chemical compound 0.000 title claims abstract description 345
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims description 49
- 230000008569 process Effects 0.000 title claims description 41
- 229910052751 metal Inorganic materials 0.000 claims abstract description 32
- 239000002184 metal Substances 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 30
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 13
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims abstract description 9
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
- 150000002602 lanthanoids Chemical group 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims abstract description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 93
- 239000003054 catalyst Substances 0.000 claims description 76
- 229920000642 polymer Polymers 0.000 claims description 69
- 150000001336 alkenes Chemical class 0.000 claims description 64
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 57
- 239000002253 acid Substances 0.000 claims description 51
- 239000003063 flame retardant Substances 0.000 claims description 45
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 44
- 239000005977 Ethylene Substances 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 39
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 38
- 239000002904 solvent Substances 0.000 claims description 38
- 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 36
- 229920001169 thermoplastic Polymers 0.000 claims description 36
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 35
- 229910052723 transition metal Inorganic materials 0.000 claims description 35
- 150000003624 transition metals Chemical class 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 29
- 239000003446 ligand Substances 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 24
- 150000003623 transition metal compounds Chemical class 0.000 claims description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 21
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229920001187 thermosetting polymer Polymers 0.000 claims description 15
- 239000008139 complexing agent Substances 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- 239000012778 molding material Substances 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 12
- 239000000654 additive Substances 0.000 claims description 12
- 239000004416 thermosoftening plastic Substances 0.000 claims description 12
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 239000004634 thermosetting polymer Substances 0.000 claims description 11
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 10
- 229910052697 platinum Inorganic materials 0.000 claims description 10
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 9
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 8
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 8
- 150000003863 ammonium salts Chemical class 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 238000000465 moulding Methods 0.000 claims description 8
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 claims description 8
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 8
- 229920000728 polyester Polymers 0.000 claims description 8
- 239000004814 polyurethane Substances 0.000 claims description 8
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical group CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000003822 epoxy resin Substances 0.000 claims description 7
- 125000000524 functional group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 229920000647 polyepoxide Polymers 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001033 ether group Chemical group 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229920005594 polymer fiber Polymers 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 6
- 239000010948 rhodium Substances 0.000 claims description 6
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 6
- 229940124597 therapeutic agent Drugs 0.000 claims description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003172 aldehyde group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000001913 cellulose Substances 0.000 claims description 5
- 229920002678 cellulose Polymers 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 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 5
- 239000000463 material Substances 0.000 claims description 5
- 125000002560 nitrile group Chemical group 0.000 claims description 5
- 229920006254 polymer film Polymers 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 5
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 150000002739 metals Chemical class 0.000 claims description 4
- 239000002480 mineral oil Substances 0.000 claims description 4
- 239000003973 paint Substances 0.000 claims description 4
- 239000012779 reinforcing material Substances 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000005600 alkyl phosphonate group Chemical group 0.000 claims description 3
- 238000005260 corrosion Methods 0.000 claims description 3
- 230000007797 corrosion Effects 0.000 claims description 3
- 239000003599 detergent Substances 0.000 claims description 3
- 239000004744 fabric Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 238000005470 impregnation Methods 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000011814 protection agent Substances 0.000 claims description 3
- 239000003352 sequestering agent Substances 0.000 claims description 3
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims description 2
- 150000004808 allyl alcohols Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000012459 cleaning agent Substances 0.000 claims description 2
- 230000009970 fire resistant effect Effects 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 2
- 235000010446 mineral oil Nutrition 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- 239000002023 wood Substances 0.000 claims description 2
- SHJYPSKHHQXPNG-UHFFFAOYSA-N 2-aminoethylphosphonous acid Chemical group NCCP(O)O SHJYPSKHHQXPNG-UHFFFAOYSA-N 0.000 claims 1
- SOEYCMDWHXVTQC-UHFFFAOYSA-N 3-aminopropylphosphonous acid Chemical compound NCCCP(O)O SOEYCMDWHXVTQC-UHFFFAOYSA-N 0.000 claims 1
- 239000004971 Cross linker Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 66
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
- 239000000047 product Substances 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 33
- 229920001577 copolymer Polymers 0.000 description 32
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 29
- 239000012071 phase Substances 0.000 description 23
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 17
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 16
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000005056 polyisocyanate Substances 0.000 description 12
- 229920001228 polyisocyanate Polymers 0.000 description 12
- 239000004952 Polyamide Substances 0.000 description 11
- 229920002647 polyamide Polymers 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001993 dienes Chemical class 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 239000004417 polycarbonate Substances 0.000 description 9
- 229920005862 polyol Polymers 0.000 description 9
- 150000003077 polyols Chemical class 0.000 description 9
- 239000000377 silicon dioxide Substances 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-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
- 150000003003 phosphines Chemical class 0.000 description 8
- 229920002857 polybutadiene Polymers 0.000 description 8
- 229920001707 polybutylene terephthalate Polymers 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- 239000005062 Polybutadiene Substances 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 229920006324 polyoxymethylene Polymers 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- 239000007983 Tris buffer Substances 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 229940052303 ethers for general anesthesia Drugs 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 229920001684 low density polyethylene Polymers 0.000 description 6
- 239000004702 low-density polyethylene Substances 0.000 description 6
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 239000004800 polyvinyl chloride Substances 0.000 description 6
- 229920000915 polyvinyl chloride Polymers 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 235000013772 propylene glycol Nutrition 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 5
- 229920002943 EPDM rubber Polymers 0.000 description 5
- 229920002292 Nylon 6 Polymers 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000004132 cross linking Methods 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 5
- 239000011591 potassium Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 229920006055 Durethan® Polymers 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 229920000877 Melamine resin Polymers 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 229910000990 Ni alloy Inorganic materials 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- AQBOUNVXZQRXNP-UHFFFAOYSA-L azane;dichloropalladium Chemical compound N.N.N.N.Cl[Pd]Cl AQBOUNVXZQRXNP-UHFFFAOYSA-L 0.000 description 4
- NOWPEMKUZKNSGG-UHFFFAOYSA-N azane;platinum(2+) Chemical compound N.N.N.N.[Pt+2] NOWPEMKUZKNSGG-UHFFFAOYSA-N 0.000 description 4
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 4
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- NYBDEQVBEYXMHK-UHFFFAOYSA-N methyl prop-2-enoate;5-phenylpenta-2,4-dienenitrile Chemical compound COC(=O)C=C.N#CC=CC=CC1=CC=CC=C1 NYBDEQVBEYXMHK-UHFFFAOYSA-N 0.000 description 1
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- RYOPVFUGUFDYKP-UHFFFAOYSA-L n,n-dimethyl-1-phenylmethanamine;palladium(2+);dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.CN(C)CC1=CC=CC=[C-]1.CN(C)CC1=CC=CC=[C-]1 RYOPVFUGUFDYKP-UHFFFAOYSA-L 0.000 description 1
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- VSWALKINGSNVAR-UHFFFAOYSA-N naphthalen-1-ol;phenol Chemical compound OC1=CC=CC=C1.C1=CC=C2C(O)=CC=CC2=C1 VSWALKINGSNVAR-UHFFFAOYSA-N 0.000 description 1
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- FBMUYWXYWIZLNE-UHFFFAOYSA-N nickel phosphide Chemical compound [Ni]=P#[Ni] FBMUYWXYWIZLNE-UHFFFAOYSA-N 0.000 description 1
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- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BWSZXUOMATYHHI-UHFFFAOYSA-N tert-butyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(C)(C)C BWSZXUOMATYHHI-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- UFDHBDMSHIXOKF-UHFFFAOYSA-N tetrahydrophthalic acid Natural products OC(=O)C1=C(C(O)=O)CCCC1 UFDHBDMSHIXOKF-UHFFFAOYSA-N 0.000 description 1
- KCNSDMPZCKLTQP-UHFFFAOYSA-N tetraphenylen-1-ol Chemical compound C12=CC=CC=C2C2=CC=CC=C2C2=CC=CC=C2C2=C1C=CC=C2O KCNSDMPZCKLTQP-UHFFFAOYSA-N 0.000 description 1
- YNHJECZULSZAQK-UHFFFAOYSA-N tetraphenylporphyrin Chemical compound C1=CC(C(=C2C=CC(N2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3N2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 YNHJECZULSZAQK-UHFFFAOYSA-N 0.000 description 1
- VXIWVFJYLFAWKN-UHFFFAOYSA-J tetrasodium 3-[[2-[2-[bis(3-sulfonatophenyl)phosphanylmethyl]phenyl]phenyl]methyl-(3-sulfonatophenyl)phosphanyl]benzenesulfonate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC(P(CC=2C(=CC=CC=2)C=2C(=CC=CC=2)CP(C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=C(C=CC=2)S([O-])(=O)=O)=C1 VXIWVFJYLFAWKN-UHFFFAOYSA-J 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 150000003556 thioamides Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229940006280 thiosulfate ion Drugs 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- 230000008467 tissue growth 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
- KFUSEUYYWQURPO-OWOJBTEDSA-N trans-1,2-dichloroethene Chemical compound Cl\C=C\Cl KFUSEUYYWQURPO-OWOJBTEDSA-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
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical group N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 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
- MOSFSEPBWRXKJZ-UHFFFAOYSA-N tridecylphosphane Chemical compound CCCCCCCCCCCCCP MOSFSEPBWRXKJZ-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
- FPZZZGJWXOHLDJ-UHFFFAOYSA-N trihexylphosphane Chemical compound CCCCCCP(CCCCCC)CCCCCC FPZZZGJWXOHLDJ-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
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- OUNAJLWMVZKFDK-UHFFFAOYSA-K tripotassium 2-bis(2-sulfonatophenyl)phosphanylbenzenesulfonate Chemical compound [K+].[K+].[K+].[O-]S(=O)(=O)C1=CC=CC=C1P(C=1C(=CC=CC=1)S([O-])(=O)=O)C1=CC=CC=C1S([O-])(=O)=O OUNAJLWMVZKFDK-UHFFFAOYSA-K 0.000 description 1
- PBZIEJBOAYSADZ-UHFFFAOYSA-K tripotassium 5-bis(2,4-dimethyl-5-sulfonatophenyl)phosphanyl-2,4-dimethylbenzenesulfonate Chemical compound [K+].[K+].[K+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1P(C=1C(=CC(C)=C(C=1)S([O-])(=O)=O)C)C1=CC(S([O-])(=O)=O)=C(C)C=C1C PBZIEJBOAYSADZ-UHFFFAOYSA-K 0.000 description 1
- KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-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
- IQKSLJOIKWOGIZ-UHFFFAOYSA-N tris(4-chlorophenyl)phosphane Chemical compound C1=CC(Cl)=CC=C1P(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IQKSLJOIKWOGIZ-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
- RTNPUWLBWXIECX-UHFFFAOYSA-N tris[4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)phenyl]phosphane Chemical compound C1=CC(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)=CC=C1P(C=1C=CC(=CC=1)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C1=CC=C(C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F)C=C1 RTNPUWLBWXIECX-UHFFFAOYSA-N 0.000 description 1
- CTSUHMKFLNRDPS-UHFFFAOYSA-K trisodium;2-bis(2-sulfonatophenyl)phosphanylbenzenesulfonate Chemical compound [Na+].[Na+].[Na+].[O-]S(=O)(=O)C1=CC=CC=C1P(C=1C(=CC=CC=1)S([O-])(=O)=O)C1=CC=CC=C1S([O-])(=O)=O CTSUHMKFLNRDPS-UHFFFAOYSA-K 0.000 description 1
- YVYHEZNITVEWDK-UHFFFAOYSA-K trisodium;5-bis(2,4-dimethyl-5-sulfonatophenyl)phosphanyl-2,4-dimethylbenzenesulfonate Chemical compound [Na+].[Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C=C1P(C=1C(=CC(C)=C(C=1)S([O-])(=O)=O)C)C1=CC(S([O-])(=O)=O)=C(C)C=C1C YVYHEZNITVEWDK-UHFFFAOYSA-K 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
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical group C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- 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
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- 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
- C07F9/4816—Acyclic saturated acids or derivatices which can have further substituents on alkyl
-
- 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
- C07F9/48—Phosphonous acids [RP(OH)2] including [RHP(=O)(OH)]; Thiophosphonous acids including [RP(SH)2], [RHP(=S)(SH)]; Derivatives thereof
- 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
- C07F9/485—Polyphosphonous acids or derivatives
-
- C—CHEMISTRY; METALLURGY
- 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
- C08K5/5393—Phosphonous compounds, e.g. R—P(OR')2
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
A−P(=O)(OX)−H (I)
式中、
Aは、C2−C20−アルキル、C2−C20−アルキレン、C8−C20アルカリールを意味し、これらは場合によっては置換されており、そして
Xは、H、アルキル、アリール、アルキルアリール、アルケニル、置換されたアルキル、アリール、アルカリール、アルケニル、アンモニウム、第一、第二、第三、第四アルキル−及び/またはアリール−アンモニウム、アルカリ金属、アルカリ土類金属、第3主族及び第4主族並びに第2亜族、第4亜族、第8亜族の金属、またはランタノイド族の金属を意味する]
更に本発明は、これらの製造方法及びこれらの化合物の使用にも関する。
Description
A−P(=O)(OX)−H (I)
に相当するアルキル亜ホスホン酸は、これまで知られる従来技術では、その一部のものしか知られていない。なぜならば、従来、これは全く得ることができないかまたは得ることが非常に困難であったからである。これまで理論的に考えられ得るアルキル亜ホスホン酸の多くはなおも製造されていない。
[式中、
Aは、C2−C20−アルキル、C2−C20−アルキレン、C8−C20アルカリールを意味し、これらは場合により置換されており、そして
Xは、H、アルキル、アリール、アルキルアリール、アルケニル、置換されたアルキル、アリール、アルカリール、アルケニル、アンモニウム、第一、第二、第三、第四アルキル−及び/またはアリール−アンモニウム、アルカリ金属、アルカリ土類金属、第3及び第4主族並びに第2、第4、第8亜族の金属、またはランタノイド族の金属を意味する]
a) 触媒の存在下にホスフィン酸源をオレフィンと反応させ、
b) 任意に、溶媒及び/またはオレフィンを分離し、
c) 触媒、触媒系、遷移金属及び/または遷移金属化合物を分離し、
d) 配位子及び/または錯化剤を分離し、
e) 助剤及び/またはオレフィンを分離する、
ことを特徴とする。
a) 触媒の存在下にホスフィン酸源をオレフィンを反応させ、
b) 不溶性の生成物を濾別する、
ことを特徴とする。
a) 触媒の存在下にホスフィン酸源をオレフィンと反応させ、
b) 任意に、触媒を濾別し、
c) 配位子及び/または錯化剤を分離し、
d) 溶媒を除去する、
ことを特徴とする。
a) 触媒の存在下にホスフィン酸源をオレフィンと反応させ、
b) 任意に、触媒を分離し、
c) 配位子及び/または錯化剤を分離し、
d) 溶媒を分離し、
e) 除去した触媒あるいは配位子及び/または錯化剤の少なくとも90%を段階a)に戻す、
ことを特徴とする。
式中、R1〜R4は、同一かまたは異なり、水素、炭素原子数1〜18のアルキル基、及び/または炭素原子数2〜18のアルケニル基、及び/または炭素原子数8〜18のアリール基、及び/または官能基、例えばカルボニル基、アルデヒド基、カルボキシ基、ヒドロキシ基、スルホン酸基、ニトリル基、シアノ基及び/またはエポキシ基; 第一、第二及び/または第三アミノ基、及び/またはエステルまたはエーテル基を表す。
−他の合成のための中間物質としての、
−バインダーとしての、
−エポキシ樹脂、ポリウレタン、不飽和ポリエステル樹脂の硬化の際の架橋剤または促進剤としての、
−ポリマー安定剤としての、
−植物保護剤としての、
−ヒト及び動物のための治療薬としてのまたは治療薬中の助剤としての、
−金属イオン封鎖剤としての、
−鉱油添加剤としての、
−腐食防止剤としての、
−洗剤及び洗浄剤の用途での、
−エレクトロニクスでの用途での、
使用に関する。
式中、R1〜R4は、同一かまたは異なることができ、そして水素、炭素原子数1〜18のアルキル基、炭素原子数2〜18のアルケニル基、及び/または炭素原子数8〜18のアリール基、及び/または官能基、例えばカルボニル基、アルデヒド基、カルボキシ基、ヒドロキシ基、スルホン酸基、ニトリル基、シアノ基及び/またはエポキシ基、第一、第二及び/または第三アミノ基、及び/またはエステル、エーテル基を表す。
ニッケル(II)、モリブデン酸ニッケル(II)、オクタン酸ニッケル(II)、シュウ酸ニッケル(II)、酸化ニッケル(II)、過塩素酸ニッケル(II)、ニッケル(II)フタロシアニン、スルファミン酸ニッケル(II)、硫酸ニッケル(II)、ニッケル−亜鉛−鉄−酸化物、エチオポルフィリンIニッケル、ランタノイド−ニッケル−合金、LaNi4.5Co0.5、ランタノイド−ニッケル−合金、LaNi5、混合金属ニッケル−合金、(Ce、La、Nd、Pr)Ni5、カリウムニッケル(IV)パラペリオデート、ジルコニウム−ニッケル−合金、ビス(エチルシクロペンタジエニル)ニッケル(II)、ビス(エチレンジアミン)ニッケル(II)クロライド、ビス(N,N'−ジイソプロピルアセトアミジナト)ニッケル(II)、トリス(エチレンジアミン)ニッケル(II)クロライド、ビス(N,N−ジメチル−N'−5H−ピリド[2,3−a]フェノチアジン−5−イリデン−1,4−フェニレンジアミン)ニッケル(II)ジパークロレート、ビス(1,3−ジアミノ−2−プロパノール)ニッケル(II)チオシアネート、ビス(N,N−ジエチルエチレンジアミン)ニッケル(II)チオシアネート、トリス(エチレンジアミン)−ニッケル(II)クロライド、トリス(エチレンジアミン)ニッケル(II)スルフェート、2,2'−チオビス(4−tert−オクチルフェノラト)−N−ブチルアミンニッケル(II)、[1,1'−ビス(ジフェニルホスフィノ)フェロセン]ジクロロニッケル(II)、[1,2−ビス(ジフェニルホスフィノ)エタン]ジクロロニッケル(II)、クロロ(エチルシクロペンタジエニル)(トリフェニルホスフィンニッケル(II)、ジリチウムテトラブロモニッケレート(II)、ヘキサアミン-ニッケル(II)ブロマイド、N,N'−ビス(サリチリデン)エチレンジアミノニッケル(II)、カリウムテトラシアノ-ニッケレート(II)、cis−ジアミン白金(II)ジクロライド、cis−ジクロロビス(ジエチルスルフィド)白金(II)、cis−ジクロロビス(ピリジン)白金(II)、cis−ジクロロビス(トリエチルホスフィン)白金(II)、cis−ジクロロビス(トリフェニルホスフィン)白金(II)、ジブロモ(1,5−シクロオクタジエン)白金(II)、ジクロロ(1,10−フェナントロリン)白金(II)、ジクロロ(1,2−ジアミノシクロヘキサン)白金(II)、ジクロロ(1,5−シクロオクタジエン)白金(II)、ジクロロ(エチレンジアミン)白金(II)、ジクロロ−ビス(エチレンジアミン)白金(II)、エチレンビス(トリフェニルホスフィン)白金(0)、(N,N,N'−トリメチルエチレンジアミン)白金(III)クロライド、ポリマー結合型白金、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、白金ブラック、白金(II)アセチルアセトネート、臭化白金(II)、塩化白金(II)、ヨウ化白金(II)、塩化白金(IV)、酸化白金(IV)、活性炭に担持した白金、アルミナに担持した白金、炭に担持した白金、シリカに担持した白金、カリウムヘキサクロロプラチネート(IV)、テトラキス(トリフェニルホスフィン)白金(0)、トランス−ジクロロビス(トリエチルホスフィン)白金(II)、トランス−ジクロロビス(トリフェニルホスフィン)白金(II)、アンモニウムヘキサクロロプラチネート(IV)、アンモニウムテトラクロロプラチネート(II)、シアン化白金(II)、白金−イリジウム合金(70:30)、硫化白金(IV)、白金オクタエチルポルフィリン、白金−パラジウム−金合金、白金−ロジウム合金、ナトリウムヘキサクロロプラチネート(IV)、トランス−白金(II)ジアミンジクロライド、カリウムテトラクロロプラチネート(II)、カリウムテトラシアノプラチネート(II)、クロロ(2,2':6',2''−ターピリジン)白金(II)クロライド、ジクロロ(2,2':6',2''−ターピリジン)白金(II)、オキサリ白金、トランス−ジクロロビス(ジエチルスルフィド)白金(II)、トリメチル(メチルシクロペンタジエニル)白金(IV)、カルボ白金、(+)−トランス−ジクロロ(エチレン)(アルファ−メチルフェネチルアミン)白金(II)、(1,5−シクロオクタジエン)ジメチル白金(II)、(2,2'−ビピリジン)ジクロロ白金(II)、クロロ白金酸、cis−ビス(アセトニトリル)ジクロロ白金(II)、cis−ビス(ベンゾニトリル)ジクロロ白金(II)、cis−ジアンミンテトラクロロ白金(IV)、ジアミンジニトリト白金(II)、カリウムトリクロロ-(エチレン)プラチネート(II)、ナトリウムヘキサヒドロキシプラチネート(IV)、テトラアミン白金(II)クロライド、テトラアミン白金(II)ヒドロキシド、テトラアミン白金(II)ニトレート、テトラアミン白金(II)テトラクロロプラチネート(II)、テトラブチルアンモニウムヘキサクロロプラチネート(IV)、ロジウムアセテートダイマー、塩化ロジウム、臭化ロジウム、ヨウ化ロジウム、ロジウムアセチルアセトネート、アセチルアセトナトビス(エチレン)ロジウム、クロロビス(エチレン)ロジウムダイマー、ジカルボニル(アセチルアセトナト)ロジウム、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、クロロカルボニルビス(トリフェニルホスフィン)、ヒドリドカルボニルトリス(トリフェニルホスフィン)ロジウム、クロロトリス(トリフェニルホスフィン)−ロジウム、ブロモトリス(トリフェニルホスフィン)ロジウム、ヨードトリス(トリフェニルホスフィン)ロジウム、クロロカルボニルビス(トリメチルホスファイト)ロジウム、ブロモトリス(トリフェニルホスフィン)ロジウム、クロロ(1,5−シクロオクタジエニル)(トリフェニルホスフィン)ロジウム、トリクロロトリス(ピリジン)ロジウム及び/またはビス(1,5−シクロオクタジエン)ロジウム(I)テトラフルオロボレートである。
式中、R5基は、互いに独立して、水素、直鎖状、分枝状もしくは環状C1−C20アルキル、C1−C20アルキルアリール、C2−C20アルケニル、C2−C20アルキニル、C1−C20カルボキシレート、C1−C20アルコキシ、C1−C20アルケニルオキシ、C1−C20アルキニルオキシ、C2−C20アルコキシカルボニル、C1−C20アルキルチオ、C1−C20アルキルスルホニル、C1−C20アルキルスルフィニル、シリル及びこれの誘導体、及び/または少なくとも一つのR6によって置換されたフェニルまたは少なくとも一つのR6によって置換されたナフチルを表す。R6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(R7)M、−CO2M、−PO3M2、−AsO3M2、−SiO2M、−C(CF3)2OM(M=H、Li、Na、K)を表し、この際、R7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、シリル及びこれの誘導体、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/またはビフェニルであることができる。
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。
特に好ましくは、反応は、1:0.01〜1:0.000001のホスフィン酸−触媒のモル比で行われる。
単相系
不均一系として作動する触媒は、懸濁状態でまたは固定相に結合された状態で働く。
多相系
多相系は溶媒系の適当な選択という点に特色があり、生成物及び触媒が異なる相中に存在するかまたは生成物がいずれの相にも溶解しないということを特徴とする。
a) 触媒を溶媒中に仕込み、そしてホスフィン酸源及びオレフィンを順次加えることによって、
b) 触媒を溶媒中に仕込み、そしてオレフィン及びホスフィン酸源を順次加えることによって、
c) 触媒を仕込み、そしてホスフィン酸源及びオレフィンを順次加えることによって、
d) 触媒を仕込み、そしてオレフィン及びホスフィン酸源を順次加えることによって、
e) ホスフィン酸源を溶媒中に仕込み、そして触媒及びオレフィンを順次加えることによって、
f) ホスフィン酸源を溶媒中に仕込み、そしてオレフィン及び触媒を順次加えることによって、
g) ホスフィン酸源を仕込み、そして触媒及びオレフィンを順次加えることによって、
h) ホスフィン酸源を仕込み、そしてオレフィン及び触媒を順次加えることによって、
i) オレフィンを溶媒中に仕込み、そしてホスフィン酸源及び触媒を順次加えることによって、
j) オレフィンを溶媒中に仕込み、そして触媒及びホスフィン酸源を順次加えることによって、
j) オレフィンを仕込み、そしてホスフィン酸源及び触媒を順次加えることによって、
l) オレフィンを仕込み、そして触媒及びホスフィン酸源を順次加えることによって、
行われる。
−バインダー、例えば鋳造用材料及び鋳型砂用バインダーとしての、
−エポキシ樹脂、ポリウレタン、不飽和ポリエステル樹脂の硬化の際の架橋剤または促進剤としての、
−ポリマー安定剤、例えば木綿布、ポリマー繊維、プラスチック用の光保護安定剤及び/または熱安定剤としての、
−植物保護剤、例えば植物生長調節剤、除草剤、殺虫剤、殺菌剤としての、
−ヒト及び動物用の治療薬または治療薬中の添加剤としての、例えば酵素モジュレータとしての、組織成長の刺激のための、
−金属イオン封鎖剤としての、例えば工業的な水道システムにおける沈殿物の管理のための、鉱油の採掘での及び金属処理剤中での、
−鉱油添加剤、例えば酸化防止剤としての及びオクタン価の向上のための、
−腐食防止剤としての、
−洗剤及び洗浄剤用途における、例えば脱色剤としての、
−エレクトロニクス用途、例えばコンデンサー、バッテリー及びアキュムレーターのための高分子電解質における、並びに感光性層中でのラジカル捕捉剤としての、
−アルキルホスホン酸の製造のための前駆体としての、
使用である。
好適な材料温度は、ポリスチレンの場合には200〜250℃、ポリプロピレンの場合には200〜300℃、ポリエチレンテレフタレート(PET)の場合には250〜290℃、ポリブチレンテレフタレート(PBT)の場合には230〜270℃、ポリアミド6(PA6)の場合には260〜290℃、ポリアミド6.6(PA6.6)の場合には260〜290℃、そしてポリカーボネートの場合には280〜320℃である。
重合の際の架橋のための適当な触媒または促進剤は、第三アミン、ベンジルジメチルアミン、N−アルキルピリジン類、イミダゾール、1−メチルイミダゾール、2−メチルイミダゾール、2−エチル−4−メチルイミダゾール、2−エチル−4−メチルイミダゾール、2−フェニルイミダゾール、2−ヘプタデシルイミダゾール、有機酸の金属塩、ルイス酸、及びアミン錯体塩である。
適当な触媒は、強塩基、カルボン酸のアルカリ金属塩、または脂肪族第三アミン類である。好ましいものは、第四水酸化アンモニウム、アルカリ金属水酸化物またはアルコキシド、酢酸ナトリウムもしくは酢酸カリウム、オクタン酸カリウム、安息香酸ナトリウム、1,4−ジアザビシクロ[2.2.2]オクタン、N,N,N’,N’−テトラメチルヘキサメチレンジアミン、N,N,N’,N’−テトラメチルプロピレンジアミン、N,N,N’,N’,N’’−ペンタメチルジエチレントリアミン、N,N’−ジ−(C1〜C2)−アルキルピペラジン、トリメチルアミノエチルピペラジン、N,N−ジメチルシクロヘキシルアミン、N,N−ジメチルベンジルアミン、N−メチルモルホリン、N−エチルモルホリン、トリメチルアミン、トリエチルアミン、トリブチルアミン、トリエチレンジアミン、ビス(ジメチルアミノアルキル)ピペラジン、N,N,N’,N’−テトラメチルエチレンジアミン、N,N−ジエチルベンジルアミン、ビス(N,N−ジエチルアミノエチル)アジペート、N,N,N’,N’−テトラメチル−1,3−ブタンジアミン、N,N−ジエチル−[ベータ]フェニルエチルアミン、1,2−ジメチルイミダゾール、2−メチルイミダゾールなどである。
室温下に、攪拌機及び強力冷却器を備えた三首フラスコ中に5852gのテトラヒドロフランを仕込み、そして攪拌及び10分間窒素を導通しながら“脱気”する。次いで、70.0mgのトリス(ジベンジリデン−アセトン)ジパラジウム及び95.0mg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加え、そして更に15分間、窒素を導通しながら攪拌する。ここで、攪拌しながら、198gの水中の198gのホスフィン酸の添加を行う。更に10分間、窒素をこの反応混合物中に通す。ここで、この反応溶液を、窒素を向流させながら、窒素雰囲気下に置いた2Lのビュッヒ反応器に移し、そしてこの三首フラスコを、少量のテトラヒドロフランで2回、後洗浄する。この反応混合物を攪拌しながら(攪拌機の回転速度:約1400rpm)、この反応器に2.5barのエチレンを入れ、そして反応混合物を80℃(外套温度)に加熱する。56gのエチレンが吸収された後、室温に冷却し、そして遊離のエチレンを燃焼して抜く。
31P−NMR(D2O、カップリング): 多重線の二重線:36.7ppm
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、1.98gのホスフィン酸、3.65gのテトラヒドロフラン、1.98gの水、0.84gのエチレン、13.7gのトリス(ジベンジリデンアセトン)ジパラジウム、19.1g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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4gのトリス(ジベンジリデンアセトン)ジパラジウム、1.9g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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、0.014mgのトリス(ジベンジリデンアセトン)ジパラジウム、0.019mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、563gの水、84gのエチレン、0.6mgの硫酸パラジウム(II)、6.8mg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反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、563gの酢酸、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのトルエン、198gの水、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、563gのブタノール、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、84gのエチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、252gのヘキセン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、312gのスチレン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例3と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、81gのブタジエン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、216gのアクリル酸、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、258gの酢酸ビニル、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、171gのアリルアミン、1.4mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.7mgのビス(ジベンジリデンアセトン)パラジウム、1.2mgの1,3−ビス(ジフェニルホスフィノ)プロパンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、3.5mgのテトラキス(トリフェニルホスフィン)パラジウム、1.7mgの4,6−ビス(ジフェニルホスフィン)フェノキサジンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、炭上に担持させた3.2mgのパラジウム、1.6mgのトリフェニルホスフィンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、0.6mgの硫酸パラジウム(II)、ポリスチレンに結合させた2.0mgのトリフェニルホスフィンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、0.7mgの酢酸パラジウム(II)、2.1mgの(オキシ−2,1−フェニレン)−ビス(ジフェニルホスフィン)を反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、3.7mgのテトラキス(トリフェニルホスフィン)白金、2.1mgの(R)−(+)−2,2'−ビス(ジフェニルホスフィノ)−1,1'−ビナフタレンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、アルミナ上に担持させた11.7mgの白金、2.4mgの1,2−ビス(ジフェニルホスフィノ)エタンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、0.4mgのニッケルジクロライド、1.7mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸、365gのテトラヒドロフラン、198gの水、84gのエチレン、3.3mgのテトラキス(トリフェニルホスフィン)ニッケル、1.7mgの1,1'−ビス(ジフェニルホスフィノ)フェロセンを反応させる。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸ナトリウム塩、563gの酢酸、84gのエチレン、0.9mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.2mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gのホスフィン酸ブチルエステル、365gのテトラヒドロフラン、198gの水、84gのエチレン、0.7mgのトリス(ジベンジリデンアセトン)ジパラジウム、0.9mg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る。正確な条件及び収量を表1に示す。
例1と同様にして、198gの次亜リン酸アンモニウム、365gのテトラヒドロフラン、198gの水、84gのエチレン、1.1mgのトリス(ジベンジリデンアセトン)ジパラジウム、1.5mg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る。正確な条件及び収量を表1に示す。
Claims (21)
- 次式(1)のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル。
A−P(=O)(OX)−H (I)
[式中、
Aは、C2−C20−アルキル、C2−C20−アルキレン、C8−C20アルカリールを意味し、但しこれらは場合によっては置換されており、そして
Xは、H、アルキル、アリール、アルキルアリール、アルケニル、置換されたアルキル、アリール、アルカリール、アルケニル、アンモニウム、第一、第二、第三、第四アルキル−及び/またはアリール−アンモニウム、アルカリ金属、アルカリ土類金属、第3主族及び第4主族の並びに第2亜族、第4亜族、第8亜族の金属、またはランタノイド族の金属を意味する] - エチル−、n−プロピル−、i−プロピル−、n−ブチル−、i−ブチル−、n−ペンチル−、i−ペンチル、n−ヘキシル−、i−ヘキシル、2−フェニルエチル−、1−フェニルエチル−、3−フェニル−プロピル−、2−フェニルプロピル−、2−ヒドロキシエチル−、3−ヒドロキシプロピル−、2−カルボキシエチル−、3−カルボキシプロピル−、2−アセタトエチル−、3−アセタトプロピル−、2−ブチラトエチル−、3−ブチラトプロピル−、2−エチルオキシエチル−、3−エチルオキシプロピル−、2−プロピルオキシエチル−、3−プロピルオキシプロピル−、2−ブチルオキシエチル−、3−ブチルオキシプロピル−、2−アミノエチル−及び/または3−アミノプロピル亜ホスホン酸、これらの塩、これらのエステル及び/またはこれらの混合物であることを特徴とする、請求項1のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル。
- アルカリ金属塩、アルカリ土類金属塩、第3主族及び第4主族並びに第2亜族、第4亜族、第8亜族の元素の塩、アンモニウム塩、第一、第二、第三、第四アルキル−及び/またはアリール−アンモニウム塩であることを特徴とする、請求項1または2のアルキル亜ホスホン酸塩。
- アルキル−、ヒドロキシアルキル−、アルキルアリール−、アリール−及び/またはアルケニルエステルであることを特徴とする請求項1または2のアルキル亜ホスホン酸エステル。
- メチル−、エチル−、プロピル−、ブチル−、エチレングリコール−、プロピレングリコール−、ベンジル−、フェニル−、ビニル−、及び/またはアリルエステルであることを特徴とする、請求項4のアルキル亜ホスホン酸エステル。
- ホスフィン酸源を、触媒の存在下にオレフィンと反応させ、この際、ホスフィン酸源が、ホスフィン酸(次亜リン酸H3PO2)、ホスフィン酸の塩、ホスフィン酸のエステル、またはこれらの混合物であることを特徴とする、アルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの製造方法。
- a) ホスフィン酸源を触媒の存在下にオレフィンと反応させ、
b) 任意に、溶媒及び/またはオレフィンを分離し、
c) 触媒、触媒系、遷移金属及び/または遷移金属化合物を分離し、
d) 配位子及び/または錯化剤を分離し、
e) 助剤及び/またはオレフィンを分離する、
ことを特徴とする、請求項6のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの製造方法。 - a) ホスフィン酸源を触媒の存在下にオレフィンと反応させ、
b) 不溶性の生成物を濾別する、
ことを特徴とする、請求項6のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの製造方法。 - a) ホスフィン酸源を触媒の存在下にオレフィンと反応させ、
b) 任意に、触媒を濾別し、
c) 配位子及び/または錯化剤を分離し、
d) 溶媒を分離する、
ことを特徴とする、請求項6のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの製造方法。 - a) ホスフィン酸源を触媒の存在下にオレフィンと反応させ、
b) 任意に、触媒を分離し、
c) 配位子及び/または錯化剤を分離し、
d) 溶媒を分離し、
e) 分離された触媒及び/または配位子及び/または錯化剤の少なくとも90%を段階a)に戻す、
ことを特徴とする、請求項6のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの製造方法。 - ホスフィン酸の塩が、アルカリ金属塩、アルカリ土類金属塩、第3主族及び第4主族、第2亜族、第4亜族、第8亜族、及びランタノイド族の元素の塩、アンモニウム塩、第一、第二、第三、第四アルキル−及び/またはアリール−アンモニウム塩であることを特徴とする、請求項6〜10の一つまたはそれ以上の方法。
- オレフィンが以下の一般式(II)に相当するものであることを特徴とする、請求項6〜11の一つまたはそれ以上の方法。
R1R2C=CR3R4 (II)
[式中、R1〜R4は、同一かまたは異なり、水素、炭素原子数1〜18のアルキル基、及び/または炭素原子数2〜18のアルケニル基、及び/または炭素原子数8〜18のアリール基、及び/または官能性基、例えばカルボニル基、アルデヒド基、カルボキシ基、ヒドロキシ基、スルホン酸基、ニトリル基、シアノ基及び/またはエポキシ基; 第一、第二及び/または第三アミノ基、及び/またはエステルもしくはエーテル基を表す] - オレフィンが、エチレン、1−プロピレン、1−ブテン、1−ペンテン、1−ヘキセン、スチレン、アリルアミン、アリルアルコール、アリル−及びビニルアルコールエーテル、アクリル酸、アクリル酸エステル、酢酸ビニル及び/または1,3−ブタジエンである、請求項6〜12の一つまたはそれ以上の方法。
- 触媒が、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/もしくは遷移金属化合物と少なくとも一種の配位子から構成される触媒系であることを特徴とする、請求項6〜13の一つまたはそれ以上の方法。
- 触媒系が、遷移金属及び/または遷移金属化合物と、少なくとも一種の配位子との反応によって形成されることを特徴とする、請求項6〜14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亜族のものであることを特徴とする、請求項6〜15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、及び/または白金であることを特徴とする、請求項6〜16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物質としての、
− バインダーとしての、
− エポキシ樹脂、ポリウレタン、不飽和ポリエステル樹脂の硬化の際の架橋剤または促進剤としての、
− ポリマー安定剤としての、
− 植物保護剤としての、
− ヒト及び動物用の、治療薬、または治療薬中の添加剤としての、
− 金属イオン封鎖剤としての、
− 鉱油添加剤としての、
− 腐食防止剤としての、
− 洗剤及び洗浄剤の用途における、
− エレクトロニクスの用途における、
請求項1〜5の一つまたはそれ以上のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、及び/または請求項6〜17の一つまたはそれ以上に従い製造されたアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの使用。 - 難燃剤、特に透明塗料及び膨張性耐火塗料用の難燃剤としての、木材及び他のセルロース含有材料の難燃剤としての、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を製造するための、難燃性ポリマー成形体の製造のための、及び/または含浸処理によるポリエステル及びセルロース単もしくは混布の難燃化処理のための、請求項1〜5の一つまたはそれ以上のアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステル、及び/または請求項6〜17の一つまたはそれ以上に従い製造されたアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルの使用。
- 請求項1〜5の少なくとも一つのアルキル亜ホスホン酸、アルキル亜ホスホン酸塩またはアルキル亜ホスホン酸エステル、及び/または請求項6〜17の一つまたはそれ以上に従い製造されたアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルを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を0.5〜95重量%、添加剤を0〜55重量%、及びフィラーもしくは強化材を0〜55重量%の割合で含み、この際、これらの成分の合計が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1〜5の少なくとも一つのアルキル亜ホスホン酸、アルキル亜ホスホン酸塩またはアルキル亜ホスホン酸エステル、及び/または請求項6〜17の一つまたはそれ以上に従い製造されたアルキル亜ホスホン酸、アルキル亜ホスホン酸塩及びアルキル亜ホスホン酸エステルを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を0.5〜95重量%、添加剤を0〜55重量%、及びフィラーもしくは強化材を0〜55重量%の割合で含み、この際、これらの成分の合計が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、ポリマーフィラメント及びポリマー繊維。
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JP2015505845A (ja) * | 2011-12-16 | 2015-02-26 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | ジホスフィン酸とアルキルホスホン酸の混和物、その製造方法、およびその使用 |
JP2015509078A (ja) * | 2011-12-16 | 2015-03-26 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | ジホスフィン酸とアルキルホスフィン酸の混和物、その製造方法、およびその使用 |
JP2015509910A (ja) * | 2011-12-16 | 2015-04-02 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | ジホスフィン酸とジアルキルホスフィン酸との混合物、その製造方法、およびその使用 |
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DE102010018682A1 (de) * | 2010-04-29 | 2011-11-03 | Clariant International Ltd. | Verfahren zur Herstellung von Alkylphosphonigsäuresalzen |
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JP2012512194A (ja) * | 2008-12-18 | 2012-05-31 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | エチレンオキシドによるモノヒドロキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩の製造方法ならびにその使用 |
JP2015505845A (ja) * | 2011-12-16 | 2015-02-26 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | ジホスフィン酸とアルキルホスホン酸の混和物、その製造方法、およびその使用 |
JP2015509078A (ja) * | 2011-12-16 | 2015-03-26 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | ジホスフィン酸とアルキルホスフィン酸の混和物、その製造方法、およびその使用 |
JP2015509910A (ja) * | 2011-12-16 | 2015-04-02 | クラリアント・ファイナンス・(ビーブイアイ)・リミテッド | ジホスフィン酸とジアルキルホスフィン酸との混合物、その製造方法、およびその使用 |
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WO2009010188A3 (de) | 2009-11-26 |
EP2178891A2 (de) | 2010-04-28 |
EP2178891B1 (de) | 2013-12-11 |
DE102007032669A1 (de) | 2009-01-15 |
KR20100043221A (ko) | 2010-04-28 |
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