BR112020004749A2 - processo de fabricação de polióis - Google Patents
processo de fabricação de polióis Download PDFInfo
- Publication number
- BR112020004749A2 BR112020004749A2 BR112020004749-0A BR112020004749A BR112020004749A2 BR 112020004749 A2 BR112020004749 A2 BR 112020004749A2 BR 112020004749 A BR112020004749 A BR 112020004749A BR 112020004749 A2 BR112020004749 A2 BR 112020004749A2
- Authority
- BR
- Brazil
- Prior art keywords
- phenyl group
- bis
- fluoroalkyl
- catalyst
- phenyl
- Prior art date
Links
- 229920005862 polyol Polymers 0.000 title claims abstract description 98
- 150000003077 polyols Chemical class 0.000 title claims abstract description 97
- 238000004519 manufacturing process Methods 0.000 title claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 93
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 90
- 238000000034 method Methods 0.000 claims abstract description 65
- 229920000570 polyether Polymers 0.000 claims abstract description 64
- 239000004721 Polyphenylene oxide Substances 0.000 claims abstract description 63
- 239000011968 lewis acid catalyst Substances 0.000 claims abstract description 51
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 48
- 239000003999 initiator Substances 0.000 claims abstract description 37
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 36
- 239000011737 fluorine Substances 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 25
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 21
- 125000000524 functional group Chemical group 0.000 claims abstract description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 15
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 229910052796 boron Inorganic materials 0.000 claims abstract description 14
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 8
- 229910052691 Erbium Chemical group 0.000 claims abstract description 6
- 229910052782 aluminium Inorganic materials 0.000 claims abstract description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical group [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052797 bismuth Inorganic materials 0.000 claims abstract description 6
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical group [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims abstract description 6
- UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical group [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052738 indium Inorganic materials 0.000 claims abstract description 6
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims abstract description 6
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 49
- -1 polyol ethylene oxide Chemical class 0.000 claims description 44
- 125000001153 fluoro group Chemical group F* 0.000 claims description 19
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 16
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 229920002635 polyurethane Polymers 0.000 claims description 11
- 239000004814 polyurethane Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 150000002009 diols Chemical class 0.000 claims description 9
- 150000004292 cyclic ethers Chemical group 0.000 claims description 7
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 165
- 238000006116 polymerization reaction Methods 0.000 abstract description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 211
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 165
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 138
- 239000000243 solution Substances 0.000 description 136
- 239000011541 reaction mixture Substances 0.000 description 127
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 100
- 239000007787 solid Substances 0.000 description 87
- 239000003039 volatile agent Substances 0.000 description 87
- 239000000047 product Substances 0.000 description 83
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 64
- 238000006243 chemical reaction Methods 0.000 description 56
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 54
- 238000010926 purge Methods 0.000 description 51
- 229910052757 nitrogen Inorganic materials 0.000 description 50
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 38
- 238000003756 stirring Methods 0.000 description 36
- 238000005227 gel permeation chromatography Methods 0.000 description 33
- 239000013078 crystal Substances 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 30
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 28
- 239000002244 precipitate Substances 0.000 description 28
- 239000007858 starting material Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 229910052744 lithium Inorganic materials 0.000 description 27
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 26
- 230000015572 biosynthetic process Effects 0.000 description 25
- 239000003921 oil Substances 0.000 description 25
- 235000019198 oils Nutrition 0.000 description 25
- 238000005481 NMR spectroscopy Methods 0.000 description 24
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 125000002947 alkylene group Chemical group 0.000 description 23
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
- 229920013701 VORANOL™ Polymers 0.000 description 20
- 239000000178 monomer Substances 0.000 description 19
- 235000011089 carbon dioxide Nutrition 0.000 description 18
- 229920001451 polypropylene glycol Polymers 0.000 description 18
- 230000008569 process Effects 0.000 description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000002841 Lewis acid Substances 0.000 description 15
- 150000007517 lewis acids Chemical class 0.000 description 15
- 238000009423 ventilation Methods 0.000 description 15
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000001994 activation Methods 0.000 description 13
- 230000000052 comparative effect Effects 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 230000004913 activation Effects 0.000 description 12
- 230000004888 barrier function Effects 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- NYULYVMJIOPWDJ-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-propan-2-yloxyborane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(OC(C)C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F NYULYVMJIOPWDJ-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 11
- 238000007086 side reaction Methods 0.000 description 11
- OBAJXDYVZBHCGT-UHFFFAOYSA-N tris(pentafluorophenyl)borane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1B(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F OBAJXDYVZBHCGT-UHFFFAOYSA-N 0.000 description 11
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Chemical group CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 10
- 239000006228 supernatant Substances 0.000 description 10
- 239000006227 byproduct Substances 0.000 description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-MZWXYZOWSA-N benzene-d6 Chemical compound [2H]C1=C([2H])C([2H])=C([2H])C([2H])=C1[2H] UHOVQNZJYSORNB-MZWXYZOWSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- 229910000085 borane Inorganic materials 0.000 description 7
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 7
- 230000003139 buffering effect Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 230000009257 reactivity Effects 0.000 description 7
- 238000004293 19F NMR spectroscopy Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- NHKZNLABLJIOEV-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-di(propan-2-yloxy)borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(OC(C)C)OC(C)C)(F)F NHKZNLABLJIOEV-UHFFFAOYSA-N 0.000 description 6
- 150000001241 acetals Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 5
- OBGNDALXOPFBFN-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C(=C(C(=C1F)F)C(F)(F)F)F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F OBGNDALXOPFBFN-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSVCVIHEBDJTCJ-UHFFFAOYSA-N 1-bromo-3,5-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC(Br)=CC(C(F)(F)F)=C1 CSVCVIHEBDJTCJ-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- GFQNSGHVOFVTLC-UHFFFAOYSA-N 2-bromo-1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(Br)=C1 GFQNSGHVOFVTLC-UHFFFAOYSA-N 0.000 description 4
- 229910015900 BF3 Inorganic materials 0.000 description 4
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- LQAMWKQGTHUPRV-UHFFFAOYSA-N [2,5-bis(trifluoromethyl)phenyl]-bis[3,5-bis(trifluoromethyl)phenyl]borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C=CC(=C1)C(F)(F)F)C(F)(F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F LQAMWKQGTHUPRV-UHFFFAOYSA-N 0.000 description 4
- GYUMNYJZAMSDAX-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-(2,4,6-trifluorophenyl)borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C=C(C=C1F)F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F GYUMNYJZAMSDAX-UHFFFAOYSA-N 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 239000002178 crystalline material Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- 239000010414 supernatant solution Substances 0.000 description 4
- XEKTVXADUPBFOA-UHFFFAOYSA-N 1-bromo-2,3,4,5,6-pentafluorobenzene Chemical compound FC1=C(F)C(F)=C(Br)C(F)=C1F XEKTVXADUPBFOA-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000002879 Lewis base Substances 0.000 description 3
- 235000019502 Orange oil Nutrition 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- GPHMETBZHAPORX-UHFFFAOYSA-N [2,5-bis(trifluoromethyl)phenyl]-[3,5-bis(trifluoromethyl)phenyl]-propan-2-yloxyborane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(OC(C)C)C1=C(C=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F GPHMETBZHAPORX-UHFFFAOYSA-N 0.000 description 3
- HLVPAFGBZNMLPW-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-(2,3,4,5,6-pentafluorophenyl)-propan-2-yloxyborane Chemical compound FC1=C(C(=C(C(=C1F)F)F)F)B(OC(C)C)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F HLVPAFGBZNMLPW-UHFFFAOYSA-N 0.000 description 3
- WLDCYFKZJMWVGT-UHFFFAOYSA-N [3,5-bis(trifluoromethyl)phenyl]-propan-2-yloxy-(3,4,5-trifluorophenyl)borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(OC(C)C)C1=CC(=C(C(=C1)F)F)F)(F)F WLDCYFKZJMWVGT-UHFFFAOYSA-N 0.000 description 3
- CFZFUDWSRPJSIK-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-(2,6-difluorophenyl)borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C=CC=C1F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F CFZFUDWSRPJSIK-UHFFFAOYSA-N 0.000 description 3
- LDDMQVLVRCIQQZ-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-[2,4-difluoro-3-(trifluoromethyl)phenyl]borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C(=C(C=C1)F)C(F)(F)F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F LDDMQVLVRCIQQZ-UHFFFAOYSA-N 0.000 description 3
- NLVRLBMBWRTHTQ-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-[2-fluoro-3-(trifluoromethyl)phenyl]borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C(=CC=C1)C(F)(F)F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F NLVRLBMBWRTHTQ-UHFFFAOYSA-N 0.000 description 3
- ZAPHUOPKNXYPRZ-UHFFFAOYSA-N bis[3,5-bis(trifluoromethyl)phenyl]-[2-fluoro-4-(trifluoromethyl)phenyl]borane Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)B(C1=C(C=C(C=C1)C(F)(F)F)F)C1=CC(=CC(=C1)C(F)(F)F)C(F)(F)F)(F)F ZAPHUOPKNXYPRZ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000010276 construction Methods 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 3
- 238000009795 derivation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 150000007527 lewis bases Chemical class 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 239000010502 orange oil Substances 0.000 description 3
- 235000011837 pasties Nutrition 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- DONVNRFILRLHJB-UHFFFAOYSA-N 1-bromo-2,3,5,6-tetrafluoro-4-(trifluoromethyl)benzene Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1Br DONVNRFILRLHJB-UHFFFAOYSA-N 0.000 description 2
- SUHKWEINMZXPHI-UHFFFAOYSA-N 1-bromo-2,4-difluoro-3-(trifluoromethyl)benzene Chemical compound FC1=CC=C(Br)C(F)=C1C(F)(F)F SUHKWEINMZXPHI-UHFFFAOYSA-N 0.000 description 2
- VPXCYIIXCVJZKZ-UHFFFAOYSA-N 1-bromo-2-fluoro-3-(trifluoromethyl)benzene Chemical compound FC1=C(Br)C=CC=C1C(F)(F)F VPXCYIIXCVJZKZ-UHFFFAOYSA-N 0.000 description 2
- HRZTZLCMURHWFY-UHFFFAOYSA-N 2-bromo-1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1Br HRZTZLCMURHWFY-UHFFFAOYSA-N 0.000 description 2
- QOFBXVZPBPTCJH-UHFFFAOYSA-N 2-bromo-1-chloro-3,5-difluorobenzene Chemical compound FC1=CC(F)=C(Br)C(Cl)=C1 QOFBXVZPBPTCJH-UHFFFAOYSA-N 0.000 description 2
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- HKJCELUUIFFSIN-UHFFFAOYSA-N 5-bromo-1,2,3-trifluorobenzene Chemical compound FC1=CC(Br)=CC(F)=C1F HKJCELUUIFFSIN-UHFFFAOYSA-N 0.000 description 2
- XTEGARKTQYYJKE-UHFFFAOYSA-M Chlorate Chemical compound [O-]Cl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-M 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QTTOPFDPALZSMK-UHFFFAOYSA-N FC(C=1C=C(C=C(C=1)C(F)(F)F)BC1=C(C(=C(C(=C1F)F)F)F)F)(F)F Chemical compound FC(C=1C=C(C=C(C=1)C(F)(F)F)BC1=C(C(=C(C(=C1F)F)F)F)F)(F)F QTTOPFDPALZSMK-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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Classifications
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| DE590131T1 (de) | 1992-03-24 | 1994-12-22 | Dow Chemical Co | Neues endbehandlungsverfahren für hydroxyfunktionelle polythethern. |
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| DE19817676A1 (de) | 1998-04-21 | 1999-10-28 | Bayer Ag | Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole |
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