JP2022515125A - ポリエーテル重合プロセス - Google Patents
ポリエーテル重合プロセス Download PDFInfo
- Publication number
- JP2022515125A JP2022515125A JP2021535207A JP2021535207A JP2022515125A JP 2022515125 A JP2022515125 A JP 2022515125A JP 2021535207 A JP2021535207 A JP 2021535207A JP 2021535207 A JP2021535207 A JP 2021535207A JP 2022515125 A JP2022515125 A JP 2022515125A
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- JP
- Japan
- Prior art keywords
- metal
- catalyst
- oxide
- zinc
- cobalt
- 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.)
- Pending
Links
- 238000006116 polymerization reaction Methods 0.000 title abstract description 34
- 229920000728 polyester Polymers 0.000 title description 2
- 229910052751 metal Inorganic materials 0.000 claims abstract description 121
- 239000002184 metal Substances 0.000 claims abstract description 121
- 239000003054 catalyst Substances 0.000 claims abstract description 103
- 229910052733 gallium Inorganic materials 0.000 claims abstract description 48
- 239000011701 zinc Substances 0.000 claims abstract description 45
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 41
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 claims abstract description 40
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 35
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 230000003197 catalytic effect Effects 0.000 claims abstract description 35
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 33
- 239000010941 cobalt Substances 0.000 claims abstract description 33
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 29
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 25
- 239000010936 titanium Substances 0.000 claims abstract description 21
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 20
- 229910052735 hafnium Inorganic materials 0.000 claims abstract description 19
- 150000002739 metals Chemical class 0.000 claims abstract description 19
- 229910052738 indium Inorganic materials 0.000 claims abstract description 18
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 18
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 17
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims abstract description 17
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000010703 silicon Substances 0.000 claims abstract description 15
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052742 iron Inorganic materials 0.000 claims abstract description 14
- 239000011777 magnesium Substances 0.000 claims abstract description 14
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 14
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 13
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052750 molybdenum Inorganic materials 0.000 claims abstract description 13
- 239000011733 molybdenum Substances 0.000 claims abstract description 13
- 229910052706 scandium Inorganic materials 0.000 claims abstract description 13
- 239000011135 tin Substances 0.000 claims abstract description 12
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims abstract description 11
- 229910052721 tungsten Inorganic materials 0.000 claims abstract description 11
- 239000010937 tungsten Substances 0.000 claims abstract description 11
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims abstract description 10
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims abstract description 10
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims abstract description 10
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052718 tin Inorganic materials 0.000 claims abstract description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 M 3 ion Chemical class 0.000 claims description 130
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 60
- 239000007858 starting material Substances 0.000 claims description 39
- 229910044991 metal oxide Inorganic materials 0.000 claims description 33
- 125000002947 alkylene group Chemical group 0.000 claims description 22
- 150000004706 metal oxides Chemical class 0.000 claims description 22
- 229920000570 polyether Polymers 0.000 claims description 22
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- 239000011572 manganese Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 19
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 18
- 150000007942 carboxylates Chemical class 0.000 claims description 14
- 229910052752 metalloid Inorganic materials 0.000 claims description 14
- 150000002738 metalloids Chemical class 0.000 claims description 14
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 13
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 12
- 229910019142 PO4 Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000010452 phosphate Substances 0.000 claims description 9
- 239000002243 precursor Substances 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 235000011180 diphosphates Nutrition 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 claims description 6
- 150000004678 hydrides Chemical class 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- 229910021645 metal ion Inorganic materials 0.000 claims description 4
- 230000000379 polymerizing effect Effects 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 125000005374 siloxide group Chemical group 0.000 claims description 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract description 22
- 230000004913 activation Effects 0.000 abstract description 7
- 230000000977 initiatory effect Effects 0.000 abstract description 3
- 239000002685 polymerization catalyst Substances 0.000 abstract description 3
- 238000010586 diagram Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 42
- 150000001875 compounds Chemical class 0.000 description 41
- 229910052736 halogen Inorganic materials 0.000 description 33
- 150000002367 halogens Chemical class 0.000 description 33
- 125000004093 cyano group Chemical group *C#N 0.000 description 31
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 30
- 125000003545 alkoxy group Chemical group 0.000 description 29
- 239000000047 product Substances 0.000 description 27
- 150000001450 anions Chemical class 0.000 description 22
- 150000002736 metal compounds Chemical class 0.000 description 22
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical group OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- 239000002245 particle Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000012071 phase Substances 0.000 description 14
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 235000021317 phosphate Nutrition 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 10
- 150000003077 polyols Chemical class 0.000 description 10
- OGHBATFHNDZKSO-UHFFFAOYSA-N propan-2-olate Chemical compound CC(C)[O-] OGHBATFHNDZKSO-UHFFFAOYSA-N 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- 150000002737 metalloid compounds Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 230000008569 process Effects 0.000 description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 229910052748 manganese Inorganic materials 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 5
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 239000008139 complexing agent Substances 0.000 description 5
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 238000010923 batch production Methods 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- 239000001569 carbon dioxide Substances 0.000 description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 description 4
- 239000006260 foam Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229960005235 piperonyl butoxide Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical compound [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- WRMFBHHNOHZECA-UHFFFAOYSA-N butan-2-olate Chemical compound CCC(C)[O-] WRMFBHHNOHZECA-UHFFFAOYSA-N 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
- 150000002472 indium compounds Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 3
- 239000006069 physical mixture Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
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- 239000002244 precipitate Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical class OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 3
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- AZMMSEASPQHHTC-UHFFFAOYSA-N 2-[1,1-bis(2-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)(C)C1=CC=CC=C1O AZMMSEASPQHHTC-UHFFFAOYSA-N 0.000 description 2
- ZWQBZEFLFSFEOS-UHFFFAOYSA-N 3,5-ditert-butyl-2-hydroxybenzoic acid Chemical class CC(C)(C)C1=CC(C(O)=O)=C(O)C(C(C)(C)C)=C1 ZWQBZEFLFSFEOS-UHFFFAOYSA-N 0.000 description 2
- MGELMVKMRZOKAR-UHFFFAOYSA-J C(C1=CC=CC=C1)(=O)[O-].[W+4].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-] Chemical compound C(C1=CC=CC=C1)(=O)[O-].[W+4].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-].C(C1=CC=CC=C1)(=O)[O-] MGELMVKMRZOKAR-UHFFFAOYSA-J 0.000 description 2
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- WJERKWQDIMQJHV-UHFFFAOYSA-I [V+5].[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1 Chemical compound [V+5].[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1.[O-]C(=O)c1ccccc1 WJERKWQDIMQJHV-UHFFFAOYSA-I 0.000 description 2
- SZAJUELPXBDQDY-UHFFFAOYSA-I [V+5].[O-]c1ccccc1.[O-]c1ccccc1.[O-]c1ccccc1.[O-]c1ccccc1.[O-]c1ccccc1 Chemical compound [V+5].[O-]c1ccccc1.[O-]c1ccccc1.[O-]c1ccccc1.[O-]c1ccccc1.[O-]c1ccccc1 SZAJUELPXBDQDY-UHFFFAOYSA-I 0.000 description 2
- YOJTVGPQAALFSX-UHFFFAOYSA-J [W+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 Chemical compound [W+4].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 YOJTVGPQAALFSX-UHFFFAOYSA-J 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- CSJKPFQJIDMSGF-UHFFFAOYSA-K aluminum;tribenzoate Chemical compound [Al+3].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 CSJKPFQJIDMSGF-UHFFFAOYSA-K 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
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- SQBBHCOIQXKPHL-UHFFFAOYSA-N tributylalumane Chemical compound CCCC[Al](CCCC)CCCC SQBBHCOIQXKPHL-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-M trichloroacetate Chemical compound [O-]C(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-M 0.000 description 1
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 1
- RGGPNXQUMRMPRA-UHFFFAOYSA-N triethylgallium Chemical compound CC[Ga](CC)CC RGGPNXQUMRMPRA-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
- XCZXGTMEAKBVPV-UHFFFAOYSA-N trimethylgallium Chemical compound C[Ga](C)C XCZXGTMEAKBVPV-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- OBROYCQXICMORW-UHFFFAOYSA-N tripropoxyalumane Chemical compound [Al+3].CCC[O-].CCC[O-].CCC[O-] OBROYCQXICMORW-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 150000003682 vanadium compounds Chemical class 0.000 description 1
- 229910001935 vanadium oxide Inorganic materials 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004260 weight control Methods 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- SRWMQSFFRFWREA-UHFFFAOYSA-M zinc formate Chemical compound [Zn+2].[O-]C=O SRWMQSFFRFWREA-UHFFFAOYSA-M 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- HCOFMIWUFBMIPV-UHFFFAOYSA-L zinc;2,4-ditert-butyl-6-carboxyphenolate Chemical compound [Zn+2].CC(C)(C)C1=CC(C(O)=O)=C([O-])C(C(C)(C)C)=C1.CC(C)(C)C1=CC(C(O)=O)=C([O-])C(C(C)(C)C)=C1 HCOFMIWUFBMIPV-UHFFFAOYSA-L 0.000 description 1
- IFNXAMCERSVZCV-UHFFFAOYSA-L zinc;2-ethylhexanoate Chemical compound [Zn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O IFNXAMCERSVZCV-UHFFFAOYSA-L 0.000 description 1
- FQFRBGQLTUGOQQ-UHFFFAOYSA-N zinc;butan-2-olate Chemical compound [Zn+2].CCC(C)[O-].CCC(C)[O-] FQFRBGQLTUGOQQ-UHFFFAOYSA-N 0.000 description 1
- HEPBQSXQJMTVFI-UHFFFAOYSA-N zinc;butane Chemical compound [Zn+2].CCC[CH2-].CCC[CH2-] HEPBQSXQJMTVFI-UHFFFAOYSA-N 0.000 description 1
- DNDQQRKQIMETKZ-UHFFFAOYSA-N zinc;diethylazanide Chemical compound [Zn+2].CC[N-]CC.CC[N-]CC DNDQQRKQIMETKZ-UHFFFAOYSA-N 0.000 description 1
- APBVWJFWFCYXRR-UHFFFAOYSA-N zinc;dimethylazanide Chemical compound [Zn+2].C[N-]C.C[N-]C APBVWJFWFCYXRR-UHFFFAOYSA-N 0.000 description 1
- TXPBKKIHHOGOPS-UHFFFAOYSA-N zinc;diphenylazanide Chemical compound [Zn+2].C=1C=CC=CC=1[N-]C1=CC=CC=C1.C=1C=CC=CC=1[N-]C1=CC=CC=C1 TXPBKKIHHOGOPS-UHFFFAOYSA-N 0.000 description 1
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 description 1
- XDWXRAYGALQIFG-UHFFFAOYSA-L zinc;propanoate Chemical compound [Zn+2].CCC([O-])=O.CCC([O-])=O XDWXRAYGALQIFG-UHFFFAOYSA-L 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
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Abstract
Description
触媒錯体Iが、式:
M1 b[M2(CN)r(X1)t]c[M3(X2)6]d・nM4 xA1 y・pM5 wA2 z・qM6 gA3 hに対応し、
式中、
M1およびM4がそれぞれ、Zn2+、Fe2+、Co+2+、Ni2+、Mo4+、Mo6+、Al+3+、V4+、V5+、Sr2+、W4+、W6+、Mn2+、Sn2+、Sn4+、Pb2+、Cu2+、La3+、およびCr3+から独立して選択された金属イオンを表し、
M2およびM3がそれぞれ、Fe3+、Fe2+、Co3+、Co2+、Cr2+、Cr3+、Mn2+、Mn3+、Ir3+、Ni2+、Rh3+、Ru2+、V4+、V5+、Ni2+、Pd2+、およびPt2+から独立して選択される金属イオンを表し、
M5が、ガリウム、ハフニウム、マンガン、チタン、およびインジウムのうちの1つ以上を表し、
M6が、アルミニウム、マグネシウム、マンガン、スカンジウム、モリブデン、コバルト、タングステン、鉄、バナジウム、スズ、チタン、ケイ素、および亜鉛のうちの1つ以上を表し、M5とは異なり、
X1が、M2イオンと配位するシアン化物以外の基を表し、
X2が、M3イオンと配位するシアン化物以外の基を表し、
A1が、ハロゲン化物、硝酸塩、硫酸塩、炭酸塩、シアン化物、シュウ酸塩、チオシアン酸塩、イソシアネート、過塩素酸塩、イソチオシアン酸塩、アルカンスルホン酸塩、アリーレンスルホン酸塩、トリフルオロメタンスルホン酸塩、またはC1-4カルボキシレートを表し、
A2およびA3がそれぞれ、少なくとも1つのアルコキシド、アリールオキシ、カルボキシレート、アシル、ピロホスフェート、ホスフェート、チオホスフェート、アミド、酸化物、シロキシド、水素化物、カルバメート、ハロゲン化物、または炭化水素アニオンを表し、
b、c、およびdがそれぞれ、bおよびcがそれぞれゼロより大きい場合、静電的に中性の複合体を反映する数値であり、
xおよびyが、金属塩M4 xA1 yの電荷のバランスをとる整数であり、
rが、4~6の整数であり、
tが、0~2の整数であり、
nが、0~20の数であり、
pが、0.001~10の数であり、
qが、0.002~10の数であり、
p÷q=0.025~1.5であり、
wおよびzが、wが1~4である場合、金属塩M5 wA2 zの電荷のバランスをとる数であり、
gおよびhが、wが1~4である場合、金属塩M6 gA3 hの電荷のバランスをとる数であり、
触媒錯体IIが、亜鉛ヘキサシアノコバルテート触媒と、粒子状M5金属酸化物であって、M5が、ガリウム、ハフニウム、マンガン、チタン、またはインジウムのうちの1つ以上から選択される、粒子状M5金属酸化物と、粒子状M6金属または半金属酸化物であって、M6が、アルミニウム、マグネシウム、マンガン、スカンジウム、モリブデン、コバルト、タングステン、鉄、バナジウム、スズ、チタン、ケイ素、および亜鉛のうちの1つ以上から選択され、M5とは異なる、粒子状M6金属または半金属酸化物との混合物であり、M5金属酸化物が、亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.001~10モルのM5金属を提供する量で存在し、M6金属または半金属酸化物が、亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.002~10モルのM6金属または半金属を提供する量で存在し、M5金属と、M6金属または半金属とのモル比が、0.025~1.5である、触媒錯体である。
実施例1を作製するために、2.07gのガリウムトリ(イソプロポキシド)および20mLの無水t-ブタノールを、窒素下40℃で1時間加熱する。20mLの水を添加する。2.07gのアルミニウムトリ(s-ブトキシド)を添加する。次いで、塩化亜鉛(8.00グラム)を添加し、混合物を40℃で30分間撹拌する。次に、水(40mL)と予備混合されたヘキサシアノコバルト酸カリウム(1.728グラム)の溶液を、2.5時間かけて滴下する。次いで、フラスコ内の混合物を約20時間後に白色ゲルが形成されるまで加熱還流する。得られたゲルを水(60mL)およびtert-ブチルアルコール(60mL)に分散し、15分間遠心分離する(5000rpm)。溶媒をデカントし、得られた材料を水(60mL)とtert-ブチルアルコール(60mL)との混合物中に再び分散させる。得られた分散液を55℃で35分間加熱し、次いで15分間遠心分離する(5000rpm)。次いで、得られた材料を、蒸留水およびtert-ブチルアルコールの体積で50/50の混合物で4回洗浄し、tert-ブチルアルコール(120mL)をもう一度使用して洗浄する。洗浄された材料は、一晩60℃の真空下で一定の圧力(10mバール未満)まで乾燥させる。得られた乾燥固体は製粉され、細かく分割された粉末の形態で触媒試料を形成する。
M6半金属としてケイ素、およびM5金属としてガリウム、ハフニウム、インジウム、またはチタンを含有するハイブリッド触媒を、以下の一般的な様式で作製する。M5金属化合物(以下の表3で特定されるように)およびテトラプロピルオルトシリケートを秤量してバイアルに入れて、表3に示されるようなケイ素とM5金属とのモル比率を得る。t-ブタノール(ケイ素とM5金属との合計1モル当たり10モル)、および0.01M HCl溶液(ケイ素とM5金属との合計1モル当たり0.05モル)、および水(t-ブタノールの体積からHCl溶液の体積を引いたものに等しい)を添加し、混合物を混合しながら60℃で30分間加熱する。混合物を30℃に冷却する。t-ブタノールおよび水を1:6の体積比で添加し、続いて溶解可能なK3Co(CN)6を添加する。K3Co(CN)6の量は、表3に示されるように、ケイ素とコバルトとのモル比を提供するのに十分である。塩化亜鉛の50%水溶液を添加し、続いて、少量の分子量4000のポリ(プロピレンオキシド)ジオールを添加する。得られた反応溶液を、室温で少なくとも1時間混合する。
触媒錯体を、実施例2~14と同じ一般的な様式で作製および評価する。アルミニウムは、(アルミニウムトリブトキシドの形態で供給される)M6金属である。M5金属化合物は、チタンテトラ(ブトキシド)またはインジウムイソプロポキシドである。アルミニウムおよびM5金属の量は、表4に示される通りであり、いずれの場合も生成物の収率と同じである。比較サンプル中にチタンは存在しない。
Claims (14)
- 触媒錯体IおよびIIからなる群から選択される触媒錯体であって、
触媒錯体Iが、式:
M1 b[M2(CN)r(X1)t]c[M3(X2)6]d・nM4 xA1 y・pM5 wA2 z・qM6 gA3 hに対応し、
式中、
M1およびM4がそれぞれ、Zn2+、Fe2+、Co+2+、Ni2+、Mo4+、Mo6+、Al+3+、V4+、V5+、Sr2+、W4+、W6+、Mn2+、Sn2+、Sn4+、Pb2+、Cu2+、La3+、およびCr3+から独立して選択された金属イオンを表し、
M2およびM3がそれぞれ、Fe3+、Fe2+、Co3+、Co2+、Cr2+、Cr3+、Mn2+、Mn3+、Ir3+、Ni2+、Rh3+、Ru2+、V4+、V5+、Ni2+、Pd2+、およびPt2+から独立して選択される金属イオンを表し、
M5が、ガリウム、ハフニウム、マンガン、チタン、およびインジウムのうちの1つ以上を表し、
M6が、アルミニウム、マグネシウム、マンガン、スカンジウム、モリブデン、コバルト、タングステン、鉄、バナジウム、スズ、チタン、ケイ素、および亜鉛のうちの1つ以上を表し、M5とは異なり、
X1が、M2イオンと配位するシアン化物以外の基を表し、
X2が、前記M3イオンと配位するシアン化物以外の基を表し、
A1が、ハロゲン化物、硝酸塩、硫酸塩、炭酸塩、シアン化物、シュウ酸塩、チオシアン酸塩、イソシアネート、過塩素酸塩、イソチオシアン酸塩、アルカンスルホン酸塩、アリーレンスルホン酸塩、トリフルオロメタンスルホン酸塩、またはC1-4カルボキシレートを表し、
A2およびA3がそれぞれ、少なくとも1つのアルコキシド、アリールオキシ、カルボキシレート、アシル、ピロホスフェート、ホスフェート、チオホスフェート、アミド、酸化物、シロキシド、水素化物、カルバメート、ハロゲン化物、または炭化水素アニオンを表し、
b、c、およびdがそれぞれ、bおよびcがそれぞれゼロより大きい場合、静電的に中性の複合体を反映する数値であり、
xおよびyが、前記金属塩M4 xA1 yの電荷のバランスをとる整数であり、
rが、4~6の整数であり、
tが、0~2の整数であり、
nが、0~20の数であり、
pが、0.001~10の数であり、
qが、0.002~10の数であり、
p÷q=0.025~1.5であり、
wおよびzが、wが1~4である場合、前記金属塩M5 wA2 zの電荷のバランスをとる数であり、
gおよびhが、wが1~4である場合、前記金属塩M6 gA3 hの電荷のバランスをとる数であり、
および
触媒錯体IIが、亜鉛ヘキサシアノコバルテート触媒と、粒子状M5金属酸化物であって、M5が、ガリウム、ハフニウム、マンガン、チタン、またはインジウムのうちの1つ以上から選択される、粒子状M5金属酸化物と、粒子状M6金属または半金属酸化物であって、M6が、アルミニウム、マグネシウム、マンガン、スカンジウム、モリブデン、コバルト、タングステン、鉄、バナジウム、スズ、チタン、ケイ素、および亜鉛のうちの1つ以上から選択され、M5とは異なる、粒子状M6金属または半金属酸化物と、の混合物であり、前記M5金属酸化物が、前記亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.001~10モルのM5金属を提供する量で存在し、前記M6金属または半金属酸化物が、前記亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.002~10モルのM6金属または半金属を提供する量で存在し、M5金属と、M6金属または半金属とのモル比が、0.025~1.5である、触媒錯体。 - M1が、亜鉛であり、M2が、コバルトであり、M4が、鉄または亜鉛である、請求項1に記載の触媒錯体。
- 前記M6金属または半金属が、Al、Si、またはTiである、請求項1または2に記載の触媒錯体。
- pが、0.0025~1.5であり、qが、0.025~2である、触媒錯体Iである、請求項1~3のいずれか一項に記載の触媒錯体。
- pが、0.0025~0.25であり、qが、0.05~0.5である、触媒錯体Iである、請求項1~3のいずれか一項に記載の触媒錯体。
- p÷qが、0.05~0.5である、触媒錯体Iである、請求項1~5のいずれか一項に記載の触媒錯体。
- 前記M5金属酸化物が、前記亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.0025~1.5モルのM5金属を提供する量で存在し、前記M6金属または半金属酸化物が、前記亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.025~2モルのM6金属または半金属を提供する量で存在する、触媒IIである、請求項1~3のいずれか一項に記載の触媒錯体。
- 前記M5金属酸化物が、前記亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.0025~0.25モルのM5金属を提供する量で存在し、前記M6金属または半金属酸化物が、前記亜鉛ヘキサシアノコバルテート触媒によって提供されるコバルト1モル当たり、0.05~0.5モルのM6金属または半金属を提供する量で存在する、触媒IIである、請求項1~3のいずれか一項に記載の触媒錯体。
- 前記M6金属または半金属が、Alであり、前記M5金属が、GaおよびHfのうちの1つ以上である、請求項1~8のいずれか一項に記載の触媒錯体。
- 前記M6金属または半金属が、Siであり、前記M5金属が、Ga、In、Ti、またはHfのうちの1つ以上である、請求項1~9のいずれか一項に記載の触媒錯体。
- 前記M6金属または半金属が、Tiであり、前記M5金属が、InおよびGaのうちの1つ以上である、請求項1~10いずれか一項に記載の触媒錯体。
- ポリエーテルを生成するための方法であって、ヒドロキシル含有スターター、少なくとも1つのアルキレンオキシド、および請求項1~10のいずれか一項に記載の触媒錯体を含む反応混合物を形成することと、前記アルキレンオキシドを、前記ヒドロキシル含有スターター上で重合して、アルキレンオキシド1モル当たり、0.01モル以下のカーボネート前駆体の存在下で前記ポリエーテルを生成することと、を含む、方法。
- 請求項12に記載の方法によって生成されたポリエーテル。
- 請求項13に記載のポリエーテルを、ポリイソシアネートと反応させることによって作製されたポリウレタン。
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US3278457A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
GB1063525A (en) | 1963-02-14 | 1967-03-30 | Gen Tire & Rubber Co | Organic cyclic oxide polymers, their preparation and tires prepared therefrom |
US3427256A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanide complex compounds |
US3278458A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
US3278459A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
US3427334A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an alcohol aldehyde or ketone to increase catalytic activity |
US3427335A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an acyclic aliphatic saturated monoether,an ester and a cyclic ether and methods for making the same |
US5194613A (en) * | 1990-09-20 | 1993-03-16 | Union Carbide Chemicals & Plastics Technology Corporation | Catalytic processes for the preparation of bridged nitrogen-containing compounds |
JP3068890B2 (ja) * | 1991-05-29 | 2000-07-24 | 旭硝子株式会社 | ポリエーテル類の製造方法 |
US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
DE19709031A1 (de) * | 1997-03-06 | 1998-09-10 | Basf Ag | Verfahren zur Herstellung von Doppelmetallcyanidkatalysatoren |
DE19730467A1 (de) * | 1997-07-16 | 1999-01-21 | Bayer Ag | Neue Zink/Metall-Hexacyanocobaltat-Katalysatoren für die Herstellung von Polyetherpolyolen |
US6077978A (en) | 1997-09-17 | 2000-06-20 | Arco Chemical Technology L.P. | Direct polyoxyalkylation of glycerine with double metal cyanide catalysis |
DE19834572A1 (de) * | 1998-07-31 | 2000-02-03 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
DE19913260C2 (de) * | 1999-03-24 | 2001-07-05 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
DE10235130A1 (de) * | 2002-08-01 | 2004-02-19 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
US6696383B1 (en) * | 2002-09-20 | 2004-02-24 | Bayer Polymers Llc | Double-metal cyanide catalysts which can be used to prepare polyols and the processes related thereto |
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