EP0706534A1 - Procede de preparation de polymeres olefiniques chlores et chlorosulfones - Google Patents
Procede de preparation de polymeres olefiniques chlores et chlorosulfonesInfo
- Publication number
- EP0706534A1 EP0706534A1 EP94922001A EP94922001A EP0706534A1 EP 0706534 A1 EP0706534 A1 EP 0706534A1 EP 94922001 A EP94922001 A EP 94922001A EP 94922001 A EP94922001 A EP 94922001A EP 0706534 A1 EP0706534 A1 EP 0706534A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- monofluorobenzene
- chlorinated
- olefin polymer
- chlorine
- extruder
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims abstract description 50
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 49
- 230000008569 process Effects 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims description 7
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims abstract description 58
- 239000006227 byproduct Substances 0.000 claims abstract description 22
- RJCGZNCCVKIBHO-UHFFFAOYSA-N 1-chloro-4-fluorobenzene Chemical compound FC1=CC=C(Cl)C=C1 RJCGZNCCVKIBHO-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000013557 residual solvent Substances 0.000 claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims description 37
- 239000002904 solvent Substances 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 36
- 229910052801 chlorine Inorganic materials 0.000 claims description 34
- 238000005660 chlorination reaction Methods 0.000 claims description 26
- 239000011953 free-radical catalyst Substances 0.000 claims description 22
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 229910001868 water Inorganic materials 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 19
- 229920001577 copolymer Polymers 0.000 claims description 15
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 14
- 239000012320 chlorinating reagent Substances 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- -1 polyethylene Polymers 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 229920000573 polyethylene Polymers 0.000 claims description 7
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000001991 dicarboxylic acids Chemical class 0.000 claims description 4
- 150000005673 monoalkenes Chemical class 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 235000019398 chlorine dioxide Nutrition 0.000 claims description 3
- OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 claims description 3
- 229920001519 homopolymer Polymers 0.000 claims description 3
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 229940117927 ethylene oxide Drugs 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229920001567 vinyl ester resin Polymers 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- 150000001336 alkenes Chemical class 0.000 claims 1
- 239000000956 alloy Substances 0.000 claims 1
- 229910045601 alloy Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000010276 construction Methods 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 150000003254 radicals Chemical class 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 40
- 238000002955 isolation Methods 0.000 abstract description 13
- 230000015572 biosynthetic process Effects 0.000 abstract description 11
- 239000012429 reaction media Substances 0.000 abstract description 6
- 230000001629 suppression Effects 0.000 abstract description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 26
- 239000000243 solution Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000003849 aromatic solvent Substances 0.000 description 8
- 239000007810 chemical reaction solvent Substances 0.000 description 7
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 231100001261 hazardous Toxicity 0.000 description 3
- 238000002203 pretreatment Methods 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000806 elastomer Substances 0.000 description 2
- 239000012527 feed solution Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- YBNZVBUWVIIJND-UHFFFAOYSA-N (2z)-1-cyclononyl-2-diazocyclononane Chemical compound [N-]=[N+]=C1CCCCCCCC1C1CCCCCCCC1 YBNZVBUWVIIJND-UHFFFAOYSA-N 0.000 description 1
- RHLWQEFHFQTKNT-UHFFFAOYSA-N (2z)-1-cyclooctyl-2-diazocyclooctane Chemical compound [N-]=[N+]=C1CCCCCCC1C1CCCCCCC1 RHLWQEFHFQTKNT-UHFFFAOYSA-N 0.000 description 1
- PENBTNKXKCPEQS-UHFFFAOYSA-N 1,1,1-trichloro-2,3,3,3-tetrafluoropropane Chemical compound FC(F)(F)C(F)C(Cl)(Cl)Cl PENBTNKXKCPEQS-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- AGBWDHTZUCGTAI-UHFFFAOYSA-N 1-(cycloundecen-1-yl)-3-diazocycloundecene Chemical compound [N-]=[N+]=C1CCCCCCCCC(C=2CCCCCCCCCC=2)=C1 AGBWDHTZUCGTAI-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
- GNKPXNIWNNKLAA-UHFFFAOYSA-N 2-(1-cyanoethyldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)N=NC(C)(C)C#N GNKPXNIWNNKLAA-UHFFFAOYSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- COAUHYBSXMIJDK-UHFFFAOYSA-N 3,3-dichloro-1,1,1,2,2-pentafluoropropane Chemical compound FC(F)(F)C(F)(F)C(Cl)Cl COAUHYBSXMIJDK-UHFFFAOYSA-N 0.000 description 1
- LDTAOIUHUHHCMU-UHFFFAOYSA-N 3-methylpent-1-ene Chemical compound CCC(C)C=C LDTAOIUHUHHCMU-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229910000990 Ni alloy Inorganic materials 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- SPTHWAJJMLCAQF-UHFFFAOYSA-M ctk4f8481 Chemical compound [O-]O.CC(C)C1=CC=CC=C1C(C)C SPTHWAJJMLCAQF-UHFFFAOYSA-M 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 229920005648 ethylene methacrylic acid copolymer Polymers 0.000 description 1
- 229920006225 ethylene-methyl acrylate Polymers 0.000 description 1
- 229920005680 ethylene-methyl methacrylate copolymer Polymers 0.000 description 1
- 235000012438 extruded product Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 229920002681 hypalon Polymers 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 229920005638 polyethylene monopolymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 230000014233 sulfur utilization Effects 0.000 description 1
- 231100000606 suspected carcinogen Toxicity 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 229920006029 tetra-polymer Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/18—Introducing halogen atoms or halogen-containing groups
- C08F8/20—Halogenation
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/34—Introducing sulfur atoms or sulfur-containing groups
- C08F8/38—Sulfohalogenation
Definitions
- olefin polymers are chlorinated or chlorosulfonated in solution or suspension in monofluorobenzene and are isolated substantially in the absence of oxygen by means of a series of extruders to produce chlorinated or chlorosulfonated products having low levels of residual solvent and solvent by-products, in particular less than 0.5 weight percent.
- olefin polymers is meant homopolymers and copolymers of C2-C8 alpha-monoolefins, including graft copolymers.
- the copolyme r s may be dipolymers or higher order copolymers, such as terpolymers or tetrapolymers.
Landscapes
- Chemical & Material Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
Abstract
Procédé de préparation de polymères oléfiniques chlorés et chlorosulfonés contenant de faibles taux de solvant résiduel selon lequel on utilise comme milieu de réaction du monofluorobenzène et on isole le polymère à l'aide d'une série d'extrudeuses ventilées à boucle fermée. Ce procédé permet également de supprimer la formation d'un sous-produit tel que le monochloromonofluorobenzène.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8552793A | 1993-06-30 | 1993-06-30 | |
| US85527 | 1993-06-30 | ||
| US08/260,123 USH1582H (en) | 1993-06-30 | 1994-06-15 | Process for preparation of chlorinated and chlorosulfonated olefin polymers having low levels of residual monofluorobenzene reaction solvent and its chlorinated by-products |
| US260123 | 1994-06-15 | ||
| PCT/US1994/007075 WO1995001380A1 (fr) | 1993-06-30 | 1994-06-29 | Procede de preparation de polymeres olefiniques chlores et chlorosulfones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP0706534A1 true EP0706534A1 (fr) | 1996-04-17 |
Family
ID=26772823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP94922001A Withdrawn EP0706534A1 (fr) | 1993-06-30 | 1994-06-29 | Procede de preparation de polymeres olefiniques chlores et chlorosulfones |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | USH1582H (fr) |
| EP (1) | EP0706534A1 (fr) |
| JP (1) | JPH08512081A (fr) |
| WO (1) | WO1995001380A1 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2650093B1 (fr) | 2006-07-20 | 2015-03-04 | Albemarle Corporation | Technologie de procédé pour la récupération de polymères styréniques bromés à partir de mélanges réactionnels dans lesquels ils sont formés et/ou de conversion de ces mélanges en granulé, pellets ou pastilles |
| US20080249254A1 (en) * | 2007-04-03 | 2008-10-09 | Royce Elton Ennis | Process for chlorosulfonating polyolefins |
| US20090247719A1 (en) * | 2008-03-31 | 2009-10-01 | Dupont Performance Elastomers L.L.C. | Process for chlorosulfonating polyolefins |
| JP2012067258A (ja) * | 2010-09-27 | 2012-04-05 | Tosoh Corp | クロロスルホン化ポリオレフィンの製造方法 |
| WO2012058002A1 (fr) * | 2010-10-29 | 2012-05-03 | Dow Global Technologies Llc | Procédé d'extrusion à dégazage de matériau fondu |
| JP6105596B2 (ja) * | 2011-09-27 | 2017-03-29 | ダウ グローバル テクノロジーズ エルエルシー | 溶融脱揮押出方法 |
| CN115386027B (zh) * | 2022-09-14 | 2024-05-24 | 杭州新元化工技术开发有限公司 | 一种制备氯化聚氯乙烯的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6017401B2 (ja) * | 1980-09-04 | 1985-05-02 | 東ソー株式会社 | クロロスルホン化ポリオレフィンの分離,乾燥法 |
| JPS57123201A (en) * | 1981-01-23 | 1982-07-31 | Denki Kagaku Kogyo Kk | Production of chlorosulfonated polyethylene polymer |
| JPS6050362B2 (ja) * | 1981-04-30 | 1985-11-08 | 東ソー株式会社 | クロロスルホン化ポリエチレンの製法 |
| JPS5933303A (ja) * | 1982-08-18 | 1984-02-23 | Toyo Soda Mfg Co Ltd | クロロスルホン化ポリエチレン製造方法 |
| JPS601206A (ja) * | 1983-06-20 | 1985-01-07 | Toyo Soda Mfg Co Ltd | クロロスルホン化共重合体の製造方法 |
| JPH0618815B2 (ja) * | 1984-01-17 | 1994-03-16 | 東ソー株式会社 | クロロスルホン化ポリエチレンの製造法 |
| JPS60192730A (ja) * | 1984-03-14 | 1985-10-01 | Toyo Soda Mfg Co Ltd | クロロスルホン化ポリオレフインマスタ−バツチの製法 |
| JPS61120809A (ja) * | 1984-11-16 | 1986-06-07 | Denki Kagaku Kogyo Kk | クロルスルホン化ポリオレフインの回収方法 |
| JPS61123604A (ja) * | 1984-11-19 | 1986-06-11 | Denki Kagaku Kogyo Kk | クロロスルホン化重合体溶液から溶剤を脱揮する方法 |
| JPS61130307A (ja) * | 1984-11-30 | 1986-06-18 | Denki Kagaku Kogyo Kk | クロルスルホン化ポリオレフインの回収方法 |
| JPH05140219A (ja) * | 1991-11-21 | 1993-06-08 | Tosoh Corp | クロロスルホン化ポリオレフインの製造法 |
| JPH05140215A (ja) * | 1991-11-22 | 1993-06-08 | Tosoh Corp | 塩素化ポリオレフインの製造法 |
| US5214107A (en) * | 1992-08-03 | 1993-05-25 | E. I. Du Pont De Nemours And Company | Chlorination of olefin polymers in chlorofluorobenzene |
-
1994
- 1994-06-15 US US08/260,123 patent/USH1582H/en not_active Abandoned
- 1994-06-29 JP JP7503555A patent/JPH08512081A/ja active Pending
- 1994-06-29 EP EP94922001A patent/EP0706534A1/fr not_active Withdrawn
- 1994-06-29 WO PCT/US1994/007075 patent/WO1995001380A1/fr not_active Ceased
Non-Patent Citations (1)
| Title |
|---|
| See references of WO9501380A1 * |
Also Published As
| Publication number | Publication date |
|---|---|
| WO1995001380A1 (fr) | 1995-01-12 |
| JPH08512081A (ja) | 1996-12-17 |
| USH1582H (en) | 1996-08-06 |
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