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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| WO2022086946A1 (en) | 2020-10-23 | 2022-04-28 | Dow Global Technologies Llc | Polyurethane composition |
| CN116685594A (zh) | 2020-12-18 | 2023-09-01 | 阿尔迪斯化学有限责任公司 | 三芳基硼烷催化剂和用于使用所述催化剂选择性氢化硅烷化酯和内酯的方法 |
| CN113004510B (zh) * | 2021-03-09 | 2023-07-11 | 万华化学（宁波）容威聚氨酯有限公司 | 胺基聚醚多元醇、制备方法和用其制成的聚氨酯硬质泡沫及其制备方法 |
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| US3278459A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
| GB1063525A (en) | 1963-02-14 | 1967-03-30 | Gen Tire & Rubber Co | Organic cyclic oxide polymers, their preparation and tires prepared therefrom |
| US3427335A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an acyclic aliphatic saturated monoether,an ester and a cyclic ether and methods for making the same |
| US3278458A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
| US3427256A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanide complex compounds |
| US3278457A (en) | 1963-02-14 | 1966-10-11 | Gen Tire & Rubber Co | Method of making a polyether using a double metal cyanide complex compound |
| US3427334A (en) | 1963-02-14 | 1969-02-11 | Gen Tire & Rubber Co | Double metal cyanides complexed with an alcohol aldehyde or ketone to increase catalytic activity |
| US4927954A (en) | 1983-06-28 | 1990-05-22 | Union Carbide Chemicals And Plastics Company, Inc. | Continuous process for producing secondary alcohols and carboxylic acid esters |
| DE590131T1 (de) | 1992-03-24 | 1994-12-22 | Dow Chemical Co | Neues endbehandlungsverfahren für hydroxyfunktionelle polythethern. |
| US5470813A (en) | 1993-11-23 | 1995-11-28 | Arco Chemical Technology, L.P. | Double metal cyanide complex catalysts |
| DE19817676A1 (de) | 1998-04-21 | 1999-10-28 | Bayer Ag | Verfahren zur aufarbeitungsfreien Herstellung langkettiger Polyetherpolyole |
| CN1152905C (zh) * | 1998-07-10 | 2004-06-09 | 三洋化成工业株式会社 | 新颖聚氧化烯多元醇和制备开环聚合物的方法 |
| US6492565B2 (en) | 1998-10-07 | 2002-12-10 | Bayer Aktiengesellschaft | Process for the preparation of polyether polyols |
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2018
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