CH654221A5 - 2-komponenten-katalysator-system und verfahren zur herstellung von mit hydroxyl endenden aethern. - Google Patents
2-komponenten-katalysator-system und verfahren zur herstellung von mit hydroxyl endenden aethern. Download PDFInfo
- Publication number
- CH654221A5 CH654221A5 CH6976/80A CH697680A CH654221A5 CH 654221 A5 CH654221 A5 CH 654221A5 CH 6976/80 A CH6976/80 A CH 6976/80A CH 697680 A CH697680 A CH 697680A CH 654221 A5 CH654221 A5 CH 654221A5
- Authority
- CH
- Switzerland
- Prior art keywords
- carbon atoms
- fluorine
- hydroxyl
- oxygen
- formula
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims description 47
- 238000000034 method Methods 0.000 title claims description 22
- 150000002170 ethers Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical class [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 title 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 57
- 239000000463 material Substances 0.000 claims description 45
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 24
- 125000001931 aliphatic group Chemical group 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 239000011737 fluorine Substances 0.000 claims description 17
- 150000003606 tin compounds Chemical class 0.000 claims description 16
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- MBAKFIZHTUAVJN-UHFFFAOYSA-I hexafluoroantimony(1-);hydron Chemical compound F.F[Sb](F)(F)(F)F MBAKFIZHTUAVJN-UHFFFAOYSA-I 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052796 boron Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 239000011574 phosphorus Chemical group 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 4
- 125000004423 acyloxy group Chemical group 0.000 claims 4
- 229910052787 antimony Chemical group 0.000 claims 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical group [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 4
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 4
- 229910052785 arsenic Inorganic materials 0.000 claims 4
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical group [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 229910017049 AsF5 Inorganic materials 0.000 claims 1
- 229910004039 HBF4 Inorganic materials 0.000 claims 1
- 229910004713 HPF6 Inorganic materials 0.000 claims 1
- 229910021174 PF5 Inorganic materials 0.000 claims 1
- YBGKQGSCGDNZIB-UHFFFAOYSA-N arsenic pentafluoride Chemical compound F[As](F)(F)(F)F YBGKQGSCGDNZIB-UHFFFAOYSA-N 0.000 claims 1
- 229920005862 polyol Polymers 0.000 description 41
- 150000003077 polyols Chemical class 0.000 description 40
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 13
- -1 phosphorus compound Chemical class 0.000 description 13
- 150000001335 aliphatic alkanes Chemical class 0.000 description 9
- 125000002947 alkylene group Chemical group 0.000 description 8
- 229920000570 polyether Polymers 0.000 description 8
- 238000006116 polymerization reaction Methods 0.000 description 7
- 239000004814 polyurethane Substances 0.000 description 7
- 229920002635 polyurethane Polymers 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- DTYWIPLKZHQUMW-UHFFFAOYSA-N dibutyl(diphenyl)stannane Chemical compound C=1C=CC=CC=1[Sn](CCCC)(CCCC)C1=CC=CC=C1 DTYWIPLKZHQUMW-UHFFFAOYSA-N 0.000 description 5
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 239000011368 organic material Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
- XONFSEOHZGSMJG-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4-nonafluoro-4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonylmethylsulfonyl)butane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)CS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F XONFSEOHZGSMJG-UHFFFAOYSA-N 0.000 description 1
- NHKMCDLYQRNJNI-UHFFFAOYSA-N 1,1,1,2,2,3,3-heptafluoro-4-(2,2,3,3,4,4,4-heptafluorobutylsulfonylmethylsulfonyl)butane Chemical compound FC(F)(F)C(F)(F)C(F)(F)CS(=O)(=O)CS(=O)(=O)CC(F)(F)C(F)(F)C(F)(F)F NHKMCDLYQRNJNI-UHFFFAOYSA-N 0.000 description 1
- BFFOGQAVMGLUJF-UHFFFAOYSA-N 1,1,3,3-tetrakis(trifluoromethylsulfonyl)propane Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)CC(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F BFFOGQAVMGLUJF-UHFFFAOYSA-N 0.000 description 1
- WRSVERXVRBGMSE-UHFFFAOYSA-N 1,1-bis(trifluoromethylsulfonyl)octadecane Chemical compound CCCCCCCCCCCCCCCCCC(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F WRSVERXVRBGMSE-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- BZQAOASUJNTSGD-UHFFFAOYSA-N 1-[bis(trifluoromethylsulfonyl)methyl]naphthalene Chemical compound C1=CC=C2C(C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F)=CC=CC2=C1 BZQAOASUJNTSGD-UHFFFAOYSA-N 0.000 description 1
- TVCYRNHTFOGQSM-UHFFFAOYSA-N 2,2-bis(trifluoromethylsulfonyl)ethylbenzene Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)CC1=CC=CC=C1 TVCYRNHTFOGQSM-UHFFFAOYSA-N 0.000 description 1
- UENUNSBHNNOPBF-UHFFFAOYSA-N 2,3-bis(dichloromethyl)oxirane Chemical compound ClC(Cl)C1OC1C(Cl)Cl UENUNSBHNNOPBF-UHFFFAOYSA-N 0.000 description 1
- ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 2,3-dichloropropan-1-ol Chemical compound OCC(Cl)CCl ZXCYIJGIGSDJQQ-UHFFFAOYSA-N 0.000 description 1
- CJTAOJBBFSUSNB-UHFFFAOYSA-N 2-(1,1,2,2-tetrachloroethyl)oxirane Chemical compound ClC(Cl)C(Cl)(Cl)C1CO1 CJTAOJBBFSUSNB-UHFFFAOYSA-N 0.000 description 1
- CWZYYACZLHIHAN-UHFFFAOYSA-N 2-(1,2,2,2-tetrachloroethyl)oxirane Chemical compound ClC(Cl)(Cl)C(Cl)C1CO1 CWZYYACZLHIHAN-UHFFFAOYSA-N 0.000 description 1
- VRZNYSQBNMDONE-UHFFFAOYSA-N 2-(2,2-dichloroethyl)oxirane Chemical compound ClC(Cl)CC1CO1 VRZNYSQBNMDONE-UHFFFAOYSA-N 0.000 description 1
- KLIGCFPMFRTVFR-UHFFFAOYSA-N 2-(bromomethyl)-2-methyloxirane Chemical compound BrCC1(C)CO1 KLIGCFPMFRTVFR-UHFFFAOYSA-N 0.000 description 1
- ZDPITVORDCQGRY-UHFFFAOYSA-N 2-(chloromethyl)-2,3,3-trimethyloxirane Chemical compound CC1(C)OC1(C)CCl ZDPITVORDCQGRY-UHFFFAOYSA-N 0.000 description 1
- VVHFXJOCUKBZFS-UHFFFAOYSA-N 2-(chloromethyl)-2-methyloxirane Chemical compound ClCC1(C)CO1 VVHFXJOCUKBZFS-UHFFFAOYSA-N 0.000 description 1
- CSGMQHXVHFJWST-UHFFFAOYSA-N 2-(dichloromethyl)-2-methyloxirane Chemical compound ClC(Cl)C1(C)CO1 CSGMQHXVHFJWST-UHFFFAOYSA-N 0.000 description 1
- DIYZRTRTCGAIKG-UHFFFAOYSA-N 2-(dichloromethyl)oxirane Chemical compound ClC(Cl)C1CO1 DIYZRTRTCGAIKG-UHFFFAOYSA-N 0.000 description 1
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 1
- VFEXYZINKMLLAK-UHFFFAOYSA-N 2-(trichloromethyl)oxirane Chemical compound ClC(Cl)(Cl)C1CO1 VFEXYZINKMLLAK-UHFFFAOYSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- MDUHTZMPRUWKFF-UHFFFAOYSA-N 2-[chloro(difluoro)methyl]oxirane Chemical compound FC(F)(Cl)C1CO1 MDUHTZMPRUWKFF-UHFFFAOYSA-N 0.000 description 1
- VEVSUNRHFFVJGJ-UHFFFAOYSA-N 2-[dichloro(fluoro)methyl]oxirane Chemical compound FC(Cl)(Cl)C1CO1 VEVSUNRHFFVJGJ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-UHFFFAOYSA-N 0.000 description 1
- NBUAJOLSZMKRIT-UHFFFAOYSA-N 5-methyloctan-3-ol Chemical compound CCCC(C)CC(O)CC NBUAJOLSZMKRIT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910021630 Antimony pentafluoride Inorganic materials 0.000 description 1
- 241000209761 Avena Species 0.000 description 1
- 235000007319 Avena orientalis Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- MZSSNBZQBIYWHE-UHFFFAOYSA-N FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)C(F)(F)S(=O)(=O)C(F)(F)F Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)S(=O)(=O)C(F)(F)S(=O)(=O)C(F)(F)F MZSSNBZQBIYWHE-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 206010068188 Heat illness Diseases 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- FSSUDOSWWOORGF-UHFFFAOYSA-N [chloro(trifluoromethylsulfonyl)methyl]sulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)C(Cl)S(=O)(=O)C(F)(F)F FSSUDOSWWOORGF-UHFFFAOYSA-N 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
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- 230000032683 aging Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- VBVBHWZYQGJZLR-UHFFFAOYSA-I antimony pentafluoride Chemical compound F[Sb](F)(F)(F)F VBVBHWZYQGJZLR-UHFFFAOYSA-I 0.000 description 1
- ZMWKYYJODBYKHO-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylbenzene Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 ZMWKYYJODBYKHO-UHFFFAOYSA-N 0.000 description 1
- MYIAPBDBTMDUDP-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)methylsulfonyl-trifluoromethane Chemical compound FC(F)(F)S(=O)(=O)C(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F MYIAPBDBTMDUDP-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- YOPDMGNERLFFAW-UHFFFAOYSA-N bromo butanoate Chemical compound CCCC(=O)OBr YOPDMGNERLFFAW-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- UQZGDPBXFWNERN-UHFFFAOYSA-N chloro-[[chloro(difluoro)methyl]sulfonylmethylsulfonyl]-difluoromethane Chemical compound FC(F)(Cl)S(=O)(=O)CS(=O)(=O)C(F)(F)Cl UQZGDPBXFWNERN-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
- FFKSUTHTFIDTNU-UHFFFAOYSA-N dibutyl-bis(ethenyl)stannane Chemical compound CCCC[Sn](C=C)(C=C)CCCC FFKSUTHTFIDTNU-UHFFFAOYSA-N 0.000 description 1
- LCGVYMRFNOWPGQ-UHFFFAOYSA-N dibutyl-bis(prop-2-enyl)stannane Chemical compound CCCC[Sn](CC=C)(CC=C)CCCC LCGVYMRFNOWPGQ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- AAMBSBLPYBJZMV-UHFFFAOYSA-N ethyl 4-bromo-6,6-bis(trifluoromethylsulfonyl)hexanoate Chemical compound CCOC(=O)CCC(Br)CC(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F AAMBSBLPYBJZMV-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- WDQNIWFZKXZFAY-UHFFFAOYSA-M fentin acetate Chemical compound CC([O-])=O.C1=CC=CC=C1[Sn+](C=1C=CC=CC=1)C1=CC=CC=C1 WDQNIWFZKXZFAY-UHFFFAOYSA-M 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910021478 group 5 element Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- PNLODLAMSJGBJZ-UHFFFAOYSA-N nitro butanoate Chemical compound CCCC(=O)O[N+]([O-])=O PNLODLAMSJGBJZ-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- DFNPRTKVCGZMMC-UHFFFAOYSA-M tributyl(fluoro)stannane Chemical compound CCCC[Sn](F)(CCCC)CCCC DFNPRTKVCGZMMC-UHFFFAOYSA-M 0.000 description 1
- QBOFWVRRMVGXIG-UHFFFAOYSA-N trifluoro(trifluoromethylsulfonylmethylsulfonyl)methane Chemical compound FC(F)(F)S(=O)(=O)CS(=O)(=O)C(F)(F)F QBOFWVRRMVGXIG-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 230000000007 visual effect Effects 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
- C08G65/269—Mixed catalyst systems, i.e. containing more than one reactive component or catalysts formed in-situ
-
- 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
- B01J27/06—Halogens; 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
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/14—Phosphorus; 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
- 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/122—Metal aryl or alkyl 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
- B01J31/12—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing organo-metallic compounds or metal hydrides
- B01J31/128—Mixtures of organometallic 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
- C08G65/2603—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 the other compounds containing oxygen
- C08G65/2606—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 the other compounds containing oxygen containing hydroxyl groups
-
- 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
- B01J2231/10—Polymerisation reactions involving at least dual use catalysts, e.g. for both oligomerisation and polymerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyethers (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US7655779A | 1979-09-18 | 1979-09-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH654221A5 true CH654221A5 (de) | 1986-02-14 |
Family
ID=22132774
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH6976/80A CH654221A5 (de) | 1979-09-18 | 1980-09-17 | 2-komponenten-katalysator-system und verfahren zur herstellung von mit hydroxyl endenden aethern. |
Country Status (7)
Country | Link |
---|---|
JP (2) | JPS5655330A (fr) |
AU (1) | AU539011B2 (fr) |
CH (1) | CH654221A5 (fr) |
DE (1) | DE3035138A1 (fr) |
FR (1) | FR2465760A2 (fr) |
GB (1) | GB2059428B (fr) |
IT (1) | IT1148270B (fr) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4456697A (en) * | 1982-09-23 | 1984-06-26 | Conoco Inc. | Catalysts for alkoxylation reactions |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2327053A (en) * | 1939-11-18 | 1943-08-17 | Shell Dev | Production of hydroxy ethers |
US3305565A (en) * | 1964-07-08 | 1967-02-21 | Shell Oil Co | Polyepihalohydrin preparation using fluoboric acid catalyst |
DE1793581C3 (de) * | 1965-04-23 | 1974-02-28 | L'oreal, Paris | Polychloräther und Verfahren zu ihrer Herstellung. Ausscheidung aus: 1593217 |
FR94928E (fr) * | 1965-04-23 | 1970-01-23 | Oreal | Nouveaux agents tensio-actifs non ioniques et leur procédé de préparation. |
GB1047557A (en) * | 1965-05-04 | 1966-11-09 | Shell Int Research | Polymers of epoxy-halo-substituted alkanes |
GB1236848A (en) * | 1968-09-12 | 1971-06-23 | Kalk Chemische Fabrik Gmbh | Method of preparing transparent products consisting largely of polyepibromohydrin |
BE747316A (fr) * | 1969-03-14 | 1970-08-17 | Sumitomo Chemical Co | Procede de production de composes epoxydes |
US3632843A (en) * | 1969-03-14 | 1972-01-04 | Minnesota Mining & Mfg | Bis(perfluoroalkylsulfonyl)methanes in cationic polymerization |
US3862090A (en) * | 1971-06-28 | 1975-01-21 | Celanese Corp | Process for producing oxymethylene copolymers |
CA1187107A (fr) * | 1978-05-17 | 1985-05-14 | Loren L. Barber, Jr. | Poly(oxydes de chloroalcoylene) incolores, termines par un groupe hydroxyle |
-
1980
- 1980-09-17 CH CH6976/80A patent/CH654221A5/de not_active IP Right Cessation
- 1980-09-17 IT IT49693/80A patent/IT1148270B/it active
- 1980-09-17 DE DE19803035138 patent/DE3035138A1/de active Granted
- 1980-09-17 GB GB8030077A patent/GB2059428B/en not_active Expired
- 1980-09-17 FR FR8019985A patent/FR2465760A2/fr active Granted
- 1980-09-17 JP JP12903080A patent/JPS5655330A/ja active Pending
- 1980-09-17 AU AU62472/80A patent/AU539011B2/en not_active Ceased
-
1988
- 1988-03-22 JP JP63067996A patent/JPS63270732A/ja active Granted
Also Published As
Publication number | Publication date |
---|---|
IT8049693A0 (it) | 1980-09-17 |
AU6247280A (en) | 1981-04-09 |
JPS63270732A (ja) | 1988-11-08 |
GB2059428A (en) | 1981-04-23 |
DE3035138A1 (de) | 1981-04-02 |
JPH0343296B2 (fr) | 1991-07-02 |
GB2059428B (en) | 1984-03-14 |
AU539011B2 (en) | 1984-09-06 |
JPS5655330A (en) | 1981-05-15 |
DE3035138C2 (fr) | 1992-02-27 |
FR2465760B2 (fr) | 1983-07-18 |
IT1148270B (it) | 1986-11-26 |
FR2465760A2 (fr) | 1981-03-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |