JP5641657B2 - 一官能化ジアルキルホスフィン酸、一官能化ジアルキルホスフィン酸エステル、および一官能化ジアルキルホスフィン酸塩の調製方法、およびそれらの使用 - Google Patents

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Publication number

JP5641657B2

JP5641657B2 JP2011541124A JP2011541124A JP5641657B2 JP 5641657 B2 JP5641657 B2 JP 5641657B2 JP 2011541124 A JP2011541124 A JP 2011541124A JP 2011541124 A JP2011541124 A JP 2011541124A JP 5641657 B2 JP5641657 B2 JP 5641657B2

Authority

JP

Japan

Prior art keywords

acid

bis

complex

salt

ester

Prior art date

2008-12-19

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.)

Expired - Fee Related

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• 239000002253 acid Substances 0.000 title claims description 150
• 150000003839 salts Chemical class 0.000 title claims description 75
• 238000000034 method Methods 0.000 title claims description 70
• 150000002148 esters Chemical class 0.000 title claims description 67
• 230000008569 process Effects 0.000 title claims description 13
• 150000007513 acids Chemical class 0.000 title description 22
• 238000002360 preparation method Methods 0.000 title description 7
• -1 II Chemical compound 0.000 claims description 139
• 229910052751 metal Inorganic materials 0.000 claims description 60
• 239000002184 metal Substances 0.000 claims description 58
• 239000003054 catalyst Substances 0.000 claims description 42
• 150000001875 compounds Chemical class 0.000 claims description 39
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
• 229910052723 transition metal Inorganic materials 0.000 claims description 31
• 150000003624 transition metals Chemical class 0.000 claims description 29
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 27
• 238000006243 chemical reaction Methods 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 23
• 229910052782 aluminium Inorganic materials 0.000 claims description 22
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
• ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 claims description 21
• 229910052708 sodium Inorganic materials 0.000 claims description 20
• 229910052725 zinc Inorganic materials 0.000 claims description 20
• 150000001336 alkenes Chemical class 0.000 claims description 19
• 229910052703 rhodium Inorganic materials 0.000 claims description 19
• 239000010948 rhodium Substances 0.000 claims description 19
• XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 18
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 18
• 229910052719 titanium Inorganic materials 0.000 claims description 18
• 229910052791 calcium Inorganic materials 0.000 claims description 17
• 229910052718 tin Inorganic materials 0.000 claims description 17
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
• 229910052749 magnesium Inorganic materials 0.000 claims description 15
• 239000000463 material Substances 0.000 claims description 15
• 150000003623 transition metal compounds Chemical class 0.000 claims description 15
• 239000003446 ligand Substances 0.000 claims description 14
• 150000002736 metal compounds Chemical class 0.000 claims description 14
• 229910052700 potassium Inorganic materials 0.000 claims description 14
• 229910052726 zirconium Inorganic materials 0.000 claims description 14
• 125000002947 alkylene group Chemical group 0.000 claims description 13
• 229910052742 iron Inorganic materials 0.000 claims description 13
• 229910052759 nickel Inorganic materials 0.000 claims description 13
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 11
• 229910052763 palladium Inorganic materials 0.000 claims description 11
• 229910052684 Cerium Inorganic materials 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 229910052744 lithium Inorganic materials 0.000 claims description 10
• 150000001298 alcohols Chemical class 0.000 claims description 9
• 229910052787 antimony Inorganic materials 0.000 claims description 8
• 150000002739 metals Chemical class 0.000 claims description 8
• 229910052697 platinum Inorganic materials 0.000 claims description 8
• 229910052732 germanium Inorganic materials 0.000 claims description 7
• 229910052748 manganese Inorganic materials 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 229910052712 strontium Inorganic materials 0.000 claims description 7
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
• 150000002829 nitrogen Chemical class 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 4
• 229910017464 nitrogen compound Inorganic materials 0.000 claims description 4
• 150000002830 nitrogen compounds Chemical class 0.000 claims description 4
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
• 239000012295 chemical reaction liquid Substances 0.000 claims description 3
• 229910052802 copper Inorganic materials 0.000 claims description 3
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 3
• 229910052707 ruthenium Inorganic materials 0.000 claims description 3
• 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
• 239000003063 flame retardant Substances 0.000 description 40
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 35
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 34
• 239000002904 solvent Substances 0.000 description 31
• 229920000642 polymer Polymers 0.000 description 30
• 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 description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
• MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 25
• 150000003863 ammonium salts Chemical class 0.000 description 23
• 229920000728 polyester Polymers 0.000 description 22
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 21
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 20
• 239000000203 mixture Substances 0.000 description 20
• OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical group OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 19
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
• 150000003254 radicals Chemical class 0.000 description 18
• 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 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 17
• 239000011734 sodium Substances 0.000 description 17
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
• 239000011701 zinc Substances 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical group OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
• 159000000000 sodium salts Chemical class 0.000 description 15
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
• 239000011575 calcium Substances 0.000 description 14
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 14
• 229910052698 phosphorus Inorganic materials 0.000 description 14
• 239000011135 tin Substances 0.000 description 14
• 239000010936 titanium Substances 0.000 description 14
• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 13
• 239000004952 Polyamide Substances 0.000 description 13
• 239000000654 additive Substances 0.000 description 13
• 239000011777 magnesium Substances 0.000 description 13
• 239000000178 monomer Substances 0.000 description 13
• 229920002647 polyamide Polymers 0.000 description 13
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 12
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• 239000012778 molding material Substances 0.000 description 12
• 239000011574 phosphorus Substances 0.000 description 12
• HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 12
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
• 229910052500 inorganic mineral Inorganic materials 0.000 description 11
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• 239000005977 Ethylene Substances 0.000 description 10
• 239000012071 phase Substances 0.000 description 10
• 238000003756 stirring Methods 0.000 description 10
• LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 9
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
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• XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical class [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 9
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• WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 2
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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
• 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
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• UIUWNILCHFBLEQ-NSCUHMNNSA-N trans-pent-3-enoic acid Chemical compound C\C=C\CC(O)=O UIUWNILCHFBLEQ-NSCUHMNNSA-N 0.000 description 1
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• 239000004711 α-olefin Substances 0.000 description 1