CN1383919A - 用于制备聚醚多元醇的双金属氰化物催化剂 - Google Patents
用于制备聚醚多元醇的双金属氰化物催化剂 Download PDFInfo
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- CN1383919A CN1383919A CN02119030A CN02119030A CN1383919A CN 1383919 A CN1383919 A CN 1383919A CN 02119030 A CN02119030 A CN 02119030A CN 02119030 A CN02119030 A CN 02119030A CN 1383919 A CN1383919 A CN 1383919A
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- Prior art keywords
- acid
- poly
- ester
- altogether
- bile
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- 239000003054 catalyst Substances 0.000 title claims abstract description 113
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 24
- 239000002184 metal Substances 0.000 title claims abstract description 24
- 229920005862 polyol Polymers 0.000 title claims abstract description 14
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 title abstract description 3
- 150000003077 polyols Chemical class 0.000 title abstract description 3
- -1 cyanide compound Chemical class 0.000 claims abstract description 177
- 229920000570 polyether Polymers 0.000 claims abstract description 75
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 64
- 230000000536 complexating effect Effects 0.000 claims abstract description 51
- 238000002360 preparation method Methods 0.000 claims abstract description 48
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 239000003446 ligand Substances 0.000 claims abstract description 28
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 161
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 73
- 150000002148 esters Chemical class 0.000 claims description 61
- 229920000858 Cyclodextrin Polymers 0.000 claims description 47
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 42
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 41
- 239000011701 zinc Substances 0.000 claims description 36
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 35
- 229910052698 phosphorus Inorganic materials 0.000 claims description 35
- 239000011574 phosphorus Substances 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 35
- 229910052725 zinc Inorganic materials 0.000 claims description 35
- 235000013495 cobalt Nutrition 0.000 claims description 34
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 33
- 210000000941 bile Anatomy 0.000 claims description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 30
- 150000001408 amides Chemical class 0.000 claims description 30
- 229930182470 glycoside Natural products 0.000 claims description 30
- 150000002338 glycosides Chemical class 0.000 claims description 29
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- 238000000034 method Methods 0.000 claims description 25
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
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- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 19
- 150000002500 ions Chemical class 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims description 15
- 239000003613 bile acid Substances 0.000 claims description 15
- 150000002825 nitriles Chemical class 0.000 claims description 13
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 12
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- 239000003833 bile salt Substances 0.000 claims description 8
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 7
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- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 7
- 229920001665 Poly-4-vinylphenol Polymers 0.000 claims description 7
- 229930182556 Polyacetal Natural products 0.000 claims description 7
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 7
- 239000007864 aqueous solution Substances 0.000 claims description 7
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 7
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims description 7
- 229920002432 poly(vinyl methyl ether) polymer Polymers 0.000 claims description 7
- 229920002401 polyacrylamide Polymers 0.000 claims description 7
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 7
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- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011976 maleic acid Substances 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims description 2
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- 239000000376 reactant Substances 0.000 claims description 2
- 239000007858 starting material Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 50
- GUXRZQZCNOHHDO-UHFFFAOYSA-N 2-phosphonopropanoic acid Chemical compound OC(=O)C(C)P(O)(O)=O GUXRZQZCNOHHDO-UHFFFAOYSA-N 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 35
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- 239000000843 powder Substances 0.000 description 31
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- 238000004458 analytical method Methods 0.000 description 28
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- 229910017052 cobalt Inorganic materials 0.000 description 28
- 239000010941 cobalt Substances 0.000 description 28
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 28
- 230000035484 reaction time Effects 0.000 description 28
- 125000004386 diacrylate group Chemical group 0.000 description 27
- 125000005907 alkyl ester group Chemical group 0.000 description 26
- 229910052799 carbon Inorganic materials 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 25
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol Substances OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 15
- 229920001451 polypropylene glycol Polymers 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- MAYCICSNZYXLHB-UHFFFAOYSA-N tricaproin Chemical compound CCCCCC(=O)OCC(OC(=O)CCCCC)COC(=O)CCCCC MAYCICSNZYXLHB-UHFFFAOYSA-N 0.000 description 13
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
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- 239000012153 distilled water Substances 0.000 description 10
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 10
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- 150000005690 diesters Chemical class 0.000 description 9
- 238000000605 extraction Methods 0.000 description 9
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 description 9
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- 229910052700 potassium Inorganic materials 0.000 description 8
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- GTTSNKDQDACYLV-UHFFFAOYSA-N Trihydroxybutane Chemical compound CCCC(O)(O)O GTTSNKDQDACYLV-UHFFFAOYSA-N 0.000 description 1
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- 230000004913 activation Effects 0.000 description 1
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- 229910001420 alkaline earth metal ion Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
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- 239000002168 alkylating agent Substances 0.000 description 1
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- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 1
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- BTFJIXJJCSYFAL-UHFFFAOYSA-N arachidyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCO BTFJIXJJCSYFAL-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000005418 aryl aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
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- 238000010923 batch production Methods 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000011575 calcium Substances 0.000 description 1
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- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
- INDBQWVYFLTCFF-UHFFFAOYSA-L cobalt(2+);dithiocyanate Chemical compound [Co+2].[S-]C#N.[S-]C#N INDBQWVYFLTCFF-UHFFFAOYSA-L 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
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- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- HAKMAMKAFTZXOZ-UHFFFAOYSA-N dioctoxyphosphorylbenzene Chemical compound CCCCCCCCOP(=O)(OCCCCCCCC)C1=CC=CC=C1 HAKMAMKAFTZXOZ-UHFFFAOYSA-N 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
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- FPDXMWHJGOCDQJ-HZAMXZRMSA-N ethyl (4r)-4-[(3r,5s,7r,8r,9s,10s,12s,13r,14s,17r)-3,7,12-trihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoate Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CCC(=O)OCC)[C@@]2(C)[C@@H](O)C1 FPDXMWHJGOCDQJ-HZAMXZRMSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 229960005102 foscarnet Drugs 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 150000002327 glycerophospholipids Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000005181 hydroxyalkylaminoalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002461 imidazolidines Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- WLXLKUWDWKQINM-UHFFFAOYSA-N iridium oxalonitrile Chemical compound N#CC#N.[Ir] WLXLKUWDWKQINM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- TZIFFYYBVRIUHF-UHFFFAOYSA-N iron(3+) oxalonitrile Chemical compound N#CC#N.[Fe+3] TZIFFYYBVRIUHF-UHFFFAOYSA-N 0.000 description 1
- RUTXIHLAWFEWGM-UHFFFAOYSA-H iron(3+) sulfate Chemical compound [Fe+3].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RUTXIHLAWFEWGM-UHFFFAOYSA-H 0.000 description 1
- 229910000360 iron(III) sulfate Inorganic materials 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
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- 238000012544 monitoring process Methods 0.000 description 1
- RFDAIACWWDREDC-YUHACDEOSA-N n-cholylglycine Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@H](O)C1 RFDAIACWWDREDC-YUHACDEOSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- YPJKMVATUPSWOH-UHFFFAOYSA-N nitrooxidanyl Chemical compound [O][N+]([O-])=O YPJKMVATUPSWOH-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229950008882 polysorbate Drugs 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 235000019940 salatrim Nutrition 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- FHHPUSMSKHSNKW-SMOYURAASA-M sodium deoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 FHHPUSMSKHSNKW-SMOYURAASA-M 0.000 description 1
- OABYVIYXWMZFFJ-ZUHYDKSRSA-M sodium glycocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 OABYVIYXWMZFFJ-ZUHYDKSRSA-M 0.000 description 1
- VMSNAUAEKXEYGP-YEUHZSMFSA-M sodium glycodeoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 VMSNAUAEKXEYGP-YEUHZSMFSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 description 1
- 229940045946 sodium taurodeoxycholate Drugs 0.000 description 1
- YXHRQQJFKOHLAP-FVCKGWAHSA-M sodium;2-[[(4r)-4-[(3r,5r,8r,9s,10s,12s,13r,14s,17r)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 YXHRQQJFKOHLAP-FVCKGWAHSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 1
- 150000003549 thiazolines Chemical class 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- UAXOELSVPTZZQG-UHFFFAOYSA-N tiglic acid Natural products CC(C)=C(C)C(O)=O UAXOELSVPTZZQG-UHFFFAOYSA-N 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- IVIIAEVMQHEPAY-UHFFFAOYSA-N tridodecyl phosphite Chemical compound CCCCCCCCCCCCOP(OCCCCCCCCCCCC)OCCCCCCCCCCCC IVIIAEVMQHEPAY-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2645—Metals or compounds thereof, e.g. salts
- C08G65/2663—Metal cyanide catalysts, i.e. DMC's
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/24—Nitrogen compounds
- B01J27/26—Cyanides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Catalysts (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyethers (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10122020A DE10122020A1 (de) | 2001-05-07 | 2001-05-07 | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE10122020.0 | 2001-05-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1383919A true CN1383919A (zh) | 2002-12-11 |
Family
ID=32602399
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN02119030A Pending CN1383919A (zh) | 2001-05-07 | 2002-04-30 | 用于制备聚醚多元醇的双金属氰化物催化剂 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6953765B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP1258291A3 (cg-RX-API-DMAC10.html) |
| JP (1) | JP2003034724A (cg-RX-API-DMAC10.html) |
| KR (1) | KR20020085806A (cg-RX-API-DMAC10.html) |
| CN (1) | CN1383919A (cg-RX-API-DMAC10.html) |
| BR (1) | BR0201622A (cg-RX-API-DMAC10.html) |
| CA (1) | CA2384552A1 (cg-RX-API-DMAC10.html) |
| DE (1) | DE10122020A1 (cg-RX-API-DMAC10.html) |
| HU (1) | HUP0201506A3 (cg-RX-API-DMAC10.html) |
| MX (1) | MXPA02004514A (cg-RX-API-DMAC10.html) |
| PL (1) | PL353720A1 (cg-RX-API-DMAC10.html) |
| RU (1) | RU2002111644A (cg-RX-API-DMAC10.html) |
| SG (1) | SG102680A1 (cg-RX-API-DMAC10.html) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308079C (zh) * | 2004-11-29 | 2007-04-04 | 黎明化工研究院 | 一种氰化物络合物催化剂及其制备方法和用途 |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA05004922A (es) * | 2002-11-07 | 2005-08-18 | Dow Global Technologies Inc | Metodo para preparar catalizadores de cianuro de metal utilizando agentes formadores de complejos polimerizables. |
| KR100990062B1 (ko) * | 2003-01-28 | 2010-10-29 | 아사히 가라스 가부시키가이샤 | 폴리에테르폴리올 조성물 및 그 용도 |
| US20050090572A1 (en) * | 2003-10-10 | 2005-04-28 | Beckers Johannes G.J. | Process for the preparation of a polyether polyol |
| US20050209438A1 (en) * | 2004-03-19 | 2005-09-22 | Browne Edward P | Starter feed stream acidification in DMC-catalyzed process |
| JP2008518088A (ja) * | 2004-10-26 | 2008-05-29 | ダウ グローバル テクノロジーズ インコーポレイティド | 活性水素含有化合物をアルコキシル化する改良方法及びそれから調製したアルコキシル化化合物 |
| DE102005057895A1 (de) | 2005-12-02 | 2007-06-06 | Basf Ag | Verfahren zur Herstellung von Multimetallcyanidverbindungen |
| US8217133B2 (en) | 2006-03-08 | 2012-07-10 | Chemtura Corporation | Storage stable one component polyurethane system |
| KR100908351B1 (ko) * | 2007-04-13 | 2009-07-20 | 에스케이씨 주식회사 | 랜덤 폴리올 제조용 복금속 시안계 촉매 |
| DE102007057147A1 (de) | 2007-11-28 | 2009-06-04 | Evonik Goldschmidt Gmbh | Verfahren zur Alkoxylierung mit DMC-Katalysatoren im Schlaufenreaktor mit Strahlsauger |
| KR100941637B1 (ko) * | 2008-05-21 | 2010-02-11 | 에스케이씨 주식회사 | 반응성이 제어된, 폴리올 제조용 복금속 시안계 촉매 및이의 제조방법 |
| US8754184B2 (en) | 2009-11-16 | 2014-06-17 | Chemtura Corporation | Accelerated cure of isocyanate terminated prepolymers |
| RU2596831C2 (ru) | 2011-02-23 | 2016-09-10 | Каунсел Оф Сайнтифик Энд Индастриал Рисерч | Способ получения сверхразветвленных полиэфиров |
| EP2794711B1 (de) | 2011-12-20 | 2020-06-10 | Covestro Deutschland AG | Hydroxy-aminopolymere und verfahren zu deren herstellung |
| TWI717562B (zh) * | 2017-10-19 | 2021-02-01 | 東聯化學股份有限公司 | 高活性雙金屬氰化物觸媒及其製備方法與應用 |
| CN116332532B (zh) * | 2023-03-29 | 2025-06-10 | 泰山玻璃纤维有限公司 | 缠绕纱用水性环氧树脂成膜剂及其制备方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1063525A (en) | 1963-02-14 | 1967-03-30 | Gen Tire & Rubber Co | Organic cyclic oxide polymers, their preparation and tires prepared therefrom |
| US3829505A (en) | 1970-02-24 | 1974-08-13 | Gen Tire & Rubber Co | Polyethers and method for making the same |
| US3941849A (en) | 1972-07-07 | 1976-03-02 | The General Tire & Rubber Company | Polyethers and method for making the same |
| JP2653236B2 (ja) | 1990-10-05 | 1997-09-17 | 旭硝子株式会社 | ポリエーテル化合物の製造方法 |
| US5158922A (en) | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
| US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
| US5482908A (en) | 1994-09-08 | 1996-01-09 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| US5914073A (en) | 1995-08-11 | 1999-06-22 | Konica Corporation | Protective film for polarizing plate |
| US5627120A (en) | 1996-04-19 | 1997-05-06 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| US5693584A (en) * | 1996-08-09 | 1997-12-02 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| US6323375B1 (en) * | 1997-10-13 | 2001-11-27 | Bayer Aktiengesellschaft | Crystalline double metal cyanide catalysts for producing polyether polyols |
| DE19842382A1 (de) | 1998-09-16 | 2000-03-23 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| US6063897A (en) * | 1998-05-05 | 2000-05-16 | Arco Chemical Technology, L.P. | Acid-treated double metal cyanide complex catalysts |
| US6013596A (en) | 1998-05-18 | 2000-01-11 | Arco Chemical Technology, L.P. | Double metal cyanide catalysts containing cyclic, bidentate complexing agents |
| DE19842383A1 (de) * | 1998-09-16 | 2000-03-23 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE19906985A1 (de) * | 1999-02-19 | 2000-08-31 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| CZ20013980A3 (cs) * | 1999-05-05 | 2002-02-13 | Bayer Aktiengesellschaft | Katalyzátory z podvojných kyanidů kovů pro výrobu polyetherpolyolů |
| DE19924672A1 (de) | 1999-05-28 | 2000-11-30 | Bayer Ag | Doppelmetallcyanic-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE19953546A1 (de) * | 1999-11-08 | 2001-05-10 | Bayer Ag | Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
-
2001
- 2001-05-07 DE DE10122020A patent/DE10122020A1/de not_active Withdrawn
-
2002
- 2002-04-25 EP EP02009222A patent/EP1258291A3/de not_active Withdrawn
- 2002-04-26 SG SG200202560A patent/SG102680A1/en unknown
- 2002-04-30 CN CN02119030A patent/CN1383919A/zh active Pending
- 2002-05-02 JP JP2002130444A patent/JP2003034724A/ja active Pending
- 2002-05-02 CA CA002384552A patent/CA2384552A1/en not_active Abandoned
- 2002-05-03 US US10/138,209 patent/US6953765B2/en not_active Expired - Fee Related
- 2002-05-06 MX MXPA02004514A patent/MXPA02004514A/es unknown
- 2002-05-06 KR KR1020020024668A patent/KR20020085806A/ko not_active Withdrawn
- 2002-05-06 RU RU2002111644/04A patent/RU2002111644A/ru not_active Application Discontinuation
- 2002-05-06 PL PL02353720A patent/PL353720A1/xx not_active Application Discontinuation
- 2002-05-07 HU HU0201506A patent/HUP0201506A3/hu unknown
- 2002-05-07 BR BR0201622-2A patent/BR0201622A/pt not_active IP Right Cessation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1308079C (zh) * | 2004-11-29 | 2007-04-04 | 黎明化工研究院 | 一种氰化物络合物催化剂及其制备方法和用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003034724A (ja) | 2003-02-07 |
| BR0201622A (pt) | 2003-03-11 |
| HUP0201506A2 (hu) | 2002-12-28 |
| EP1258291A3 (de) | 2005-08-24 |
| PL353720A1 (en) | 2002-11-18 |
| EP1258291A2 (de) | 2002-11-20 |
| US6953765B2 (en) | 2005-10-11 |
| SG102680A1 (en) | 2004-03-26 |
| RU2002111644A (ru) | 2003-12-10 |
| HU0201506D0 (cg-RX-API-DMAC10.html) | 2002-07-29 |
| HUP0201506A3 (en) | 2006-11-28 |
| KR20020085806A (ko) | 2002-11-16 |
| US20020198099A1 (en) | 2002-12-26 |
| DE10122020A1 (de) | 2002-11-14 |
| MXPA02004514A (es) | 2005-08-16 |
| CA2384552A1 (en) | 2002-11-07 |
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