DE19817676A1 - Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole - Google Patents
Verfahren zur aufarbeitungsfreien Herstellung langkettiger PolyetherpolyoleInfo
- Publication number
- DE19817676A1 DE19817676A1 DE19817676A DE19817676A DE19817676A1 DE 19817676 A1 DE19817676 A1 DE 19817676A1 DE 19817676 A DE19817676 A DE 19817676A DE 19817676 A DE19817676 A DE 19817676A DE 19817676 A1 DE19817676 A1 DE 19817676A1
- Authority
- DE
- Germany
- Prior art keywords
- long
- oligomeric
- catalyst
- ppm
- catalysis
- 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.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 28
- 239000003054 catalyst Substances 0.000 claims abstract description 63
- 239000007858 starting material Substances 0.000 claims abstract description 51
- 229910052751 metal Inorganic materials 0.000 claims abstract description 26
- 239000002184 metal Substances 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 14
- 150000002739 metals Chemical class 0.000 claims abstract description 8
- 229920000570 polyether Polymers 0.000 claims description 49
- 229920005862 polyol Polymers 0.000 claims description 45
- 150000003077 polyols Chemical class 0.000 claims description 45
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 41
- 238000006555 catalytic reaction Methods 0.000 claims description 33
- -1 metals sulfonates Chemical class 0.000 claims description 22
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 14
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 12
- 229940113165 trimethylolpropane Drugs 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 8
- 230000000737 periodic effect Effects 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims description 4
- 235000011187 glycerol Nutrition 0.000 claims description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
- 229910052684 Cerium Inorganic materials 0.000 claims description 3
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 3
- 229910052691 Erbium Inorganic materials 0.000 claims description 3
- 229910052693 Europium Inorganic materials 0.000 claims description 3
- 229910052688 Gadolinium Inorganic materials 0.000 claims description 3
- 229910052689 Holmium Inorganic materials 0.000 claims description 3
- 229910052779 Neodymium Inorganic materials 0.000 claims description 3
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 3
- 229910052772 Samarium Inorganic materials 0.000 claims description 3
- 229910052771 Terbium Inorganic materials 0.000 claims description 3
- 229910052775 Thulium Inorganic materials 0.000 claims description 3
- 229910052769 Ytterbium Inorganic materials 0.000 claims description 3
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims description 3
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 3
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims description 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 3
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 3
- KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052746 lanthanum Inorganic materials 0.000 claims description 3
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims description 3
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 3
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 3
- 229910052706 scandium Inorganic materials 0.000 claims description 3
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 claims description 3
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 3
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 claims description 3
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- 229920002472 Starch Polymers 0.000 claims description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 2
- 229930006000 Sucrose Natural products 0.000 claims description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 2
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 claims description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 2
- 238000009419 refurbishment Methods 0.000 claims description 2
- 239000000600 sorbitol Substances 0.000 claims description 2
- 239000008107 starch Substances 0.000 claims description 2
- 235000019698 starch Nutrition 0.000 claims description 2
- 229960004793 sucrose Drugs 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- ADDKUYIIHFYIMV-UHFFFAOYSA-N methanesulfonic acid;trifluoromethanesulfonic acid Chemical compound CS(O)(=O)=O.OS(=O)(=O)C(F)(F)F ADDKUYIIHFYIMV-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 3
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 28
- 230000006698 induction Effects 0.000 description 14
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 12
- 239000003513 alkali Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 230000035484 reaction time Effects 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 5
- 150000002924 oxiranes Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000001681 protective effect Effects 0.000 description 4
- JPJIEXKLJOWQQK-UHFFFAOYSA-K trifluoromethanesulfonate;yttrium(3+) Chemical compound [Y+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F JPJIEXKLJOWQQK-UHFFFAOYSA-K 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 238000010923 batch production Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920002635 polyurethane Polymers 0.000 description 3
- 239000004814 polyurethane Substances 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004904 shortening Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 229910000722 Didymium Inorganic materials 0.000 description 1
- 241000224487 Didymium Species 0.000 description 1
- 229910052765 Lutetium Inorganic materials 0.000 description 1
- 229910052773 Promethium Inorganic materials 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003463 adsorbent Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- RKBAPHPQTADBIK-UHFFFAOYSA-N cobalt;hexacyanide Chemical compound [Co].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-].N#[C-] RKBAPHPQTADBIK-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- VQMWBBYLQSCNPO-UHFFFAOYSA-N promethium atom Chemical compound [Pm] VQMWBBYLQSCNPO-UHFFFAOYSA-N 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 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
-
- 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
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
- B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
-
- 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
-
- 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
- C08G65/266—Metallic elements not covered by group C08G65/2648 - C08G65/2645, or compounds thereof
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/48—Ring-opening reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Polyethers (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19817676A DE19817676A1 (de) | 1998-04-21 | 1998-04-21 | Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole |
| TW088105400A TW446723B (en) | 1998-04-21 | 1999-04-06 | Process for the production of long-chain polyether polyols without working up |
| HK02100643.9A HK1039136B (en) | 1998-04-21 | 1999-04-08 | Method for producing long-chain polyetherpolyols without reprocessing |
| KR1020007011635A KR100567719B1 (ko) | 1998-04-21 | 1999-04-08 | 후처리없이 장쇄 폴리에테르폴리올을 제조하는 방법 |
| CA002328453A CA2328453C (en) | 1998-04-21 | 1999-04-08 | Method for producing long-chain polyetherpolyols without reprocessing |
| PCT/EP1999/002397 WO1999054383A1 (de) | 1998-04-21 | 1999-04-08 | Verfahren zur aufarbeitungsfreien herstellung langkettiger polyetherpolyole |
| AU38139/99A AU3813999A (en) | 1998-04-21 | 1999-04-08 | Method for producing long-chain polyetherpolyols without reprocessing |
| IDW20002156A ID27091A (id) | 1998-04-21 | 1999-04-08 | Proses untuk produksi poliol poliester rantai panjang tanpa ditingkatkan |
| BR9909752-4A BR9909752A (pt) | 1998-04-21 | 1999-04-08 | Processo para preparação de polieterpolióis de cadeia longa livre de reprocessamento |
| DE59904736T DE59904736D1 (de) | 1998-04-21 | 1999-04-08 | Verfahren zur herstellung langkettiger polyetherpolyole |
| ES99920615T ES2193702T3 (es) | 1998-04-21 | 1999-04-08 | Procedimiento para la fabricacion de polioleteres de cadena larga. |
| US09/673,583 US6482993B1 (en) | 1998-04-21 | 1999-04-08 | Method for producing long chain polyether polyols without reprocessing |
| HU0101515A HUP0101515A3 (en) | 1998-04-21 | 1999-04-08 | Method for producing long-chain polyetherpolyols without reprocessing |
| EP99920615A EP1073689B1 (de) | 1998-04-21 | 1999-04-08 | Verfahren zur herstellung langkettiger polyetherpolyole |
| CN99807670A CN1117112C (zh) | 1998-04-21 | 1999-04-08 | 无需后处理的生产长链聚醚多元醇的方法 |
| PT99920615T PT1073689E (pt) | 1998-04-21 | 1999-04-08 | Processos para producao de polieter-poliois de cadeia comprida sem pos-tratamento |
| JP2000544721A JP4361688B2 (ja) | 1998-04-21 | 1999-04-08 | 後処理しない長鎖ポリエーテルポリオールの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19817676A DE19817676A1 (de) | 1998-04-21 | 1998-04-21 | Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19817676A1 true DE19817676A1 (de) | 1999-10-28 |
Family
ID=7865246
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19817676A Withdrawn DE19817676A1 (de) | 1998-04-21 | 1998-04-21 | Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole |
| DE59904736T Expired - Lifetime DE59904736D1 (de) | 1998-04-21 | 1999-04-08 | Verfahren zur herstellung langkettiger polyetherpolyole |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59904736T Expired - Lifetime DE59904736D1 (de) | 1998-04-21 | 1999-04-08 | Verfahren zur herstellung langkettiger polyetherpolyole |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6482993B1 (enExample) |
| EP (1) | EP1073689B1 (enExample) |
| JP (1) | JP4361688B2 (enExample) |
| KR (1) | KR100567719B1 (enExample) |
| CN (1) | CN1117112C (enExample) |
| AU (1) | AU3813999A (enExample) |
| BR (1) | BR9909752A (enExample) |
| CA (1) | CA2328453C (enExample) |
| DE (2) | DE19817676A1 (enExample) |
| ES (1) | ES2193702T3 (enExample) |
| HU (1) | HUP0101515A3 (enExample) |
| ID (1) | ID27091A (enExample) |
| PT (1) | PT1073689E (enExample) |
| TW (1) | TW446723B (enExample) |
| WO (1) | WO1999054383A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000078837A1 (de) | 1999-06-19 | 2000-12-28 | Bayer Aktiengesellschaft | Aus polyetherpolyolen hergestellte polyurethan-weichschäume |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003288142A1 (en) * | 2002-11-22 | 2004-06-18 | Basf Aktiengesellschaft | Enzymatic synthesis of polyol acrylates |
| CA3063465C (en) * | 2009-11-18 | 2023-01-03 | Nektar Therapeutics | Acid salt forms of polymer-drug conjugates and alkoxylation methods |
| US9169185B2 (en) | 2010-12-20 | 2015-10-27 | Bayer Intellectual Property Gmbh | Method for the preparation of polyether polyols |
| KR101404702B1 (ko) | 2011-03-08 | 2014-06-17 | 에스케이이노베이션 주식회사 | 에테르 결합 단위체를 함유한 이산화탄소/에폭사이드 공중합체의 제조 방법 |
| CN103476829B (zh) | 2011-03-31 | 2016-01-20 | 陶氏环球技术有限责任公司 | 利用超酸和双金属氰化物催化剂生产短链多官能聚醚多元醇的方法 |
| SG10201604976RA (en) | 2011-12-20 | 2016-08-30 | Bayer Ip Gmbh | Hydroxy-aminopolymers and method for producing same |
| WO2016064698A1 (en) | 2014-10-22 | 2016-04-28 | Dow Global Technologies Llc | Dual catalyst system for high primary hydroxyl polyols |
| CN107200837B (zh) | 2016-03-18 | 2019-10-18 | 淮安巴德聚氨酯科技有限公司 | 一种利用dmc催化剂循环制备聚醚多元醇的方法 |
| HUE068772T2 (hu) | 2017-09-14 | 2025-01-28 | Univ Northwestern | Eljárás poliolok gyártására |
| KR102603181B1 (ko) | 2017-09-14 | 2023-11-16 | 다우 글로벌 테크놀로지스 엘엘씨 | 폴리올을 제조하는 방법 |
| ES2886249T3 (es) | 2017-09-14 | 2021-12-16 | Dow Global Technologies Llc | Catalizador de polimerización ácido de Lewis |
| US11572440B2 (en) | 2020-02-18 | 2023-02-07 | Covestro Llc | Methods for purifying polyols containing oxyalkylene units to reduce 2-methyl-2-pentenal content |
| FR3111901B1 (fr) * | 2020-06-30 | 2023-02-17 | Arkema France | PROCÉdÉ D’ALCOXYLATION AMÉLIORÉ |
| CN113754877B (zh) * | 2021-09-10 | 2023-09-22 | 山东一诺威新材料有限公司 | 低导热系数聚醚多元醇的制备方法 |
| CN118878813B (zh) * | 2024-07-23 | 2025-04-25 | 上海优铖工逸技术有限公司 | 一种聚醚多元醇的合成方法 |
| CN119019670B (zh) * | 2024-10-30 | 2025-01-24 | 中化东大(淄博)有限公司 | 低粘度、高分子量聚醚多元醇及其制备方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1063525A (en) | 1963-02-14 | 1967-03-30 | Gen Tire & Rubber Co | Organic cyclic oxide polymers, their preparation and tires prepared therefrom |
| US3715402A (en) | 1969-08-08 | 1973-02-06 | Basf Wyandotte Corp | Removal of catalysts from polyols |
| 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 |
| US4137398A (en) | 1978-06-09 | 1979-01-30 | Basf Wyandotte Corporation | Process for the removal of catalyst from polyether polyol |
| DE3229216A1 (de) | 1982-08-05 | 1984-02-09 | Basf Ag, 6700 Ludwigshafen | Verfahren zur reinigung von rohen polyether-polyolen |
| US4430490A (en) | 1982-08-10 | 1984-02-07 | Ppg Industries, Inc. | Polyether polyols and their method of preparation |
| US5158922A (en) | 1992-02-04 | 1992-10-27 | Arco Chemical Technology, L.P. | Process for preparing metal cyanide complex catalyst |
| WO1995002625A2 (en) * | 1993-07-16 | 1995-01-26 | E.I. Du Pont De Nemours And Company | Polymerization/depolymerization catalyst for polyethers |
| US5482908A (en) * | 1994-09-08 | 1996-01-09 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| AU3897195A (en) * | 1994-10-28 | 1996-05-23 | E.I. Du Pont De Nemours And Company | Polymerization of cyclic ethers using selected metal compound catalysts |
| US5545601A (en) | 1995-08-22 | 1996-08-13 | Arco Chemical Technology, L.P. | Polyether-containing double metal cyanide catalysts |
| US5627120A (en) | 1996-04-19 | 1997-05-06 | Arco Chemical Technology, L.P. | Highly active double metal cyanide catalysts |
| DE19702787A1 (de) * | 1997-01-27 | 1998-07-30 | Bayer Ag | Verfahren zur Herstellung von Polyetherpolyolen |
| DE19757574A1 (de) | 1997-12-23 | 1999-06-24 | Bayer Ag | Verbesserte Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE19810269A1 (de) | 1998-03-10 | 2000-05-11 | Bayer Ag | Verbesserte Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
| DE19745120A1 (de) | 1997-10-13 | 1999-04-15 | Bayer Ag | Verbesserte Doppelmetallcyanid-Katalysatoren für die Herstellung von Polyetherpolyolen |
-
1998
- 1998-04-21 DE DE19817676A patent/DE19817676A1/de not_active Withdrawn
-
1999
- 1999-04-06 TW TW088105400A patent/TW446723B/zh not_active IP Right Cessation
- 1999-04-08 CN CN99807670A patent/CN1117112C/zh not_active Expired - Lifetime
- 1999-04-08 EP EP99920615A patent/EP1073689B1/de not_active Expired - Lifetime
- 1999-04-08 WO PCT/EP1999/002397 patent/WO1999054383A1/de not_active Ceased
- 1999-04-08 JP JP2000544721A patent/JP4361688B2/ja not_active Expired - Fee Related
- 1999-04-08 BR BR9909752-4A patent/BR9909752A/pt not_active Application Discontinuation
- 1999-04-08 DE DE59904736T patent/DE59904736D1/de not_active Expired - Lifetime
- 1999-04-08 AU AU38139/99A patent/AU3813999A/en not_active Abandoned
- 1999-04-08 KR KR1020007011635A patent/KR100567719B1/ko not_active Expired - Fee Related
- 1999-04-08 US US09/673,583 patent/US6482993B1/en not_active Expired - Lifetime
- 1999-04-08 ID IDW20002156A patent/ID27091A/id unknown
- 1999-04-08 HU HU0101515A patent/HUP0101515A3/hu unknown
- 1999-04-08 ES ES99920615T patent/ES2193702T3/es not_active Expired - Lifetime
- 1999-04-08 CA CA002328453A patent/CA2328453C/en not_active Expired - Fee Related
- 1999-04-08 PT PT99920615T patent/PT1073689E/pt unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000078837A1 (de) | 1999-06-19 | 2000-12-28 | Bayer Aktiengesellschaft | Aus polyetherpolyolen hergestellte polyurethan-weichschäume |
| US6858655B1 (en) | 1999-06-19 | 2005-02-22 | Bayer Aktiengesellschaft | High-resilient polyurethane foams produced from polyether polyols |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0101515A3 (en) | 2002-10-28 |
| KR100567719B1 (ko) | 2006-04-05 |
| CA2328453A1 (en) | 1999-10-28 |
| EP1073689A1 (de) | 2001-02-07 |
| PT1073689E (pt) | 2003-06-30 |
| CN1117112C (zh) | 2003-08-06 |
| HK1039136A1 (en) | 2002-04-12 |
| US6482993B1 (en) | 2002-11-19 |
| ID27091A (id) | 2001-03-01 |
| JP4361688B2 (ja) | 2009-11-11 |
| CN1306551A (zh) | 2001-08-01 |
| ES2193702T3 (es) | 2003-11-01 |
| HUP0101515A2 (hu) | 2001-09-28 |
| KR20010042862A (ko) | 2001-05-25 |
| CA2328453C (en) | 2008-07-15 |
| BR9909752A (pt) | 2000-12-19 |
| DE59904736D1 (de) | 2003-04-30 |
| WO1999054383A1 (de) | 1999-10-28 |
| AU3813999A (en) | 1999-11-08 |
| TW446723B (en) | 2001-07-21 |
| JP2002512283A (ja) | 2002-04-23 |
| EP1073689B1 (de) | 2003-03-26 |
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