ES2492521T3 - Proceso de disolvente común para la producción de caucho bromado de alto peso molecular - Google Patents
Proceso de disolvente común para la producción de caucho bromado de alto peso molecular Download PDFInfo
- Publication number
- ES2492521T3 ES2492521T3 ES11700540.5T ES11700540T ES2492521T3 ES 2492521 T3 ES2492521 T3 ES 2492521T3 ES 11700540 T ES11700540 T ES 11700540T ES 2492521 T3 ES2492521 T3 ES 2492521T3
- Authority
- ES
- Spain
- Prior art keywords
- weight
- rubber
- process according
- monomer
- medium
- 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.)
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- 238000000034 method Methods 0.000 title claims abstract description 92
- 230000008569 process Effects 0.000 title claims abstract description 86
- 229920001971 elastomer Polymers 0.000 title claims abstract description 83
- 239000005060 rubber Substances 0.000 title claims abstract description 83
- 239000002904 solvent Substances 0.000 title description 31
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000000178 monomer Substances 0.000 claims abstract description 127
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 54
- 229920000642 polymer Polymers 0.000 claims abstract description 32
- 239000000203 mixture Substances 0.000 claims abstract description 29
- 238000009835 boiling Methods 0.000 claims abstract description 27
- 239000007800 oxidant agent Substances 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 24
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000012429 reaction media Substances 0.000 claims abstract description 8
- 230000000379 polymerizing effect Effects 0.000 claims abstract 2
- 238000005893 bromination reaction Methods 0.000 claims description 51
- 230000031709 bromination Effects 0.000 claims description 46
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 40
- 238000006116 polymerization reaction Methods 0.000 claims description 37
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical group OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 35
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 30
- 229920005549 butyl rubber Polymers 0.000 claims description 26
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 20
- -1 cyclic aliphatic hydrocarbon Chemical class 0.000 claims description 17
- 239000007787 solid Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 150000002978 peroxides Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000243 solution Substances 0.000 description 69
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 63
- 229910052794 bromium Inorganic materials 0.000 description 19
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
- 229920005557 bromobutyl Polymers 0.000 description 18
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 15
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 14
- 238000004821 distillation Methods 0.000 description 14
- 238000000926 separation method Methods 0.000 description 12
- 238000000746 purification Methods 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 9
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000026030 halogenation Effects 0.000 description 7
- 238000005658 halogenation reaction Methods 0.000 description 7
- 229940050176 methyl chloride Drugs 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000004568 cement Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- 150000005826 halohydrocarbons Chemical class 0.000 description 6
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000011084 recovery Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000006227 byproduct Substances 0.000 description 5
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000011020 pilot scale process Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000013844 butane Nutrition 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000005086 pumping Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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
- CMAOLVNGLTWICC-UHFFFAOYSA-N 2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC=C(F)C(C#N)=C1 CMAOLVNGLTWICC-UHFFFAOYSA-N 0.000 description 1
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 description 1
- BZSXEZOLBIJVQK-UHFFFAOYSA-N 2-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC=CC=C1C(O)=O BZSXEZOLBIJVQK-UHFFFAOYSA-N 0.000 description 1
- YHQXBTXEYZIYOV-UHFFFAOYSA-N 3-methylbut-1-ene Chemical compound CC(C)C=C YHQXBTXEYZIYOV-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010793 Steam injection (oil industry) Methods 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001513 alkali metal bromide Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001616 alkaline earth metal bromide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- VRLDVERQJMEPIF-UHFFFAOYSA-N dbdmh Chemical compound CC1(C)N(Br)C(=O)N(Br)C1=O VRLDVERQJMEPIF-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010405 reoxidation reaction Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 150000003839 salts Chemical class 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
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- NYCVSSWORUBFET-UHFFFAOYSA-M sodium;bromite Chemical compound [Na+].[O-]Br=O NYCVSSWORUBFET-UHFFFAOYSA-M 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
- C08F8/22—Halogenation by reaction with free halogens
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/12—Incorporating halogen atoms into the molecule
- C08C19/14—Incorporating halogen atoms into the molecule by reaction with halogens
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/04—Polymerisation in solution
- C08F2/06—Organic solvent
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/04—Monomers containing three or four carbon atoms
- C08F210/08—Butenes
- C08F210/10—Isobutene
- C08F210/12—Isobutene with conjugated diolefins, e.g. butyl rubber
-
- 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
- C08F6/00—Post-polymerisation treatments
- C08F6/001—Removal of residual monomers by physical means
- C08F6/003—Removal of residual monomers by physical means from polymer solutions, suspensions, dispersions or emulsions without recovery of the polymer therefrom
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10000515 | 2010-01-20 | ||
| EP10000515 | 2010-01-20 | ||
| PCT/EP2011/050529 WO2011089091A1 (en) | 2010-01-20 | 2011-01-17 | Common solvent process for producing high molecular weight brominated rubber |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2492521T3 true ES2492521T3 (es) | 2014-09-09 |
Family
ID=42173467
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES11700540.5T Active ES2492521T3 (es) | 2010-01-20 | 2011-01-17 | Proceso de disolvente común para la producción de caucho bromado de alto peso molecular |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US9273160B2 (h) |
| EP (1) | EP2526123B1 (h) |
| JP (1) | JP5703311B2 (h) |
| KR (1) | KR101473542B1 (h) |
| CN (1) | CN102770461B (h) |
| CA (1) | CA2787227C (h) |
| ES (1) | ES2492521T3 (h) |
| IN (1) | IN2012DN06386A (h) |
| MY (1) | MY159846A (h) |
| RU (1) | RU2584424C2 (h) |
| SA (1) | SA111320111B1 (h) |
| SG (1) | SG182530A1 (h) |
| TW (1) | TWI513707B (h) |
| WO (1) | WO2011089091A1 (h) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011089092A1 (en) * | 2010-01-20 | 2011-07-28 | Lanxess International Sa | Common solvent process for producing high molecular weight halogenated rubber |
| JP5604582B2 (ja) * | 2010-03-24 | 2014-10-08 | ランクセス・インターナショナル・ソシエテ・アノニム | 水および溶媒を含まないポリマーの製造方法 |
| RU2622648C2 (ru) * | 2011-07-20 | 2017-06-19 | Арланксео Дойчланд Гмбх | Способ получения бромированного бутильного каучука |
| CN103467636B (zh) * | 2013-09-29 | 2015-08-19 | 浙江信汇合成新材料有限公司 | 一种溴化丁基橡胶的生产工艺 |
| SG11201608805YA (en) * | 2014-04-30 | 2016-11-29 | Arlanxeo Singapore Pte Ltd | Butyl rubber with new sequence distribution |
| CN105218719B (zh) * | 2014-06-16 | 2017-06-06 | 中国石油化工股份有限公司 | 制备卤化丁基橡胶的方法及由此得到的卤化丁基橡胶 |
| JP6486461B2 (ja) * | 2014-09-30 | 2019-03-20 | エクソンモービル ケミカル パテンツ インコーポレイテッド | 改良されたムーニー粘度安定性を有する臭素化エラストマーの調製方法 |
| JP7394854B2 (ja) | 2018-12-17 | 2023-12-08 | アランセオ・シンガポール・プライヴェート・リミテッド | ターシャリーエーテルを用いてイソオレフィンポリマーを生成する方法 |
| SG11202105460TA (en) * | 2018-12-21 | 2021-07-29 | Arlanxeo Singapore Pte Ltd | Halogen recovery in a process for halogenating unsaturated isoolefin copolymer |
| SG11202105842XA (en) | 2018-12-27 | 2021-07-29 | Arlanxeo Singapore Pte Ltd | Process for producing chlorinated butyl rubber |
| EP4105244B1 (en) | 2020-09-18 | 2024-09-04 | Lg Chem, Ltd. | Method for halogenating isobutene-isoprene copolymer |
| CN114432721B (zh) * | 2020-11-03 | 2023-09-15 | 北京诺维新材科技有限公司 | 一种聚合物溶液的提浓方法及其应用 |
| US11965053B2 (en) * | 2020-12-11 | 2024-04-23 | Arlanxeo Singapore Pte. Ltd. | Halogen recovery with K+-containing oxidant in a process for halogenating unsaturated isoolefin copolymer |
| TWI881025B (zh) * | 2021-01-25 | 2025-04-21 | 優顯科技股份有限公司 | 電子裝置及其製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3018275A (en) | 1958-12-30 | 1962-01-23 | Exxon Research Engineering Co | Halogenation of low unsaturation rubbery polymers in the presence of oxidizing agen |
| US3257349A (en) | 1963-09-17 | 1966-06-21 | Exxon Research Engineering Co | Purifying recycle streams in integrated process for preparing halogenated butyl rubber and butyl rubber latex |
| US3361725A (en) * | 1965-06-02 | 1968-01-02 | Exxon Research Engineering Co | Process for preparation of solution butyl rubbers using a major amount of air2x and a minor amount of airx2 as catalyst |
| CA1019095A (en) | 1973-06-25 | 1977-10-11 | Lev N. Vladykin | Method for preparing butyl rubber |
| IT1134567B (it) | 1980-12-03 | 1986-08-13 | Ente Giprokautchuk L | Reattore per la polimerizzazione di idrocarburi in soluzione od in sospensione |
| US5021509A (en) | 1989-09-01 | 1991-06-04 | Exxon Chemical Patents Inc. | Butyl rubber compositions having improved adhesion to polyester |
| US5077345A (en) | 1990-03-01 | 1991-12-31 | Exxon Chemical Patents Inc. | Halogenation of polymers with improved neutralization |
| IT1270944B (it) * | 1993-02-10 | 1997-05-26 | Pressindustria A G | Procedimento continuo e impianto di alogenazione di elastomeri. |
| DE4437931A1 (de) | 1994-10-24 | 1996-04-25 | Bayer Ag | Verfahren zur Bromierung von Alkylkautschuken |
| CA2174794C (en) * | 1996-04-23 | 2009-09-22 | Gabor Kaszas | Improved polymer bromination process in solution |
| CA2174795C (en) | 1996-04-23 | 2009-11-03 | Gabor Kaszas | Improved polymer bromination process |
| US5681901A (en) * | 1996-07-24 | 1997-10-28 | Exxon Chemical Patents Inc. | Process for halogenating isomonoolefin copolymers |
| CA2252295C (en) | 1998-10-30 | 2007-07-17 | Bayer Inc. | Improved process for preparation of butyl rubber utilizing activated alkylaluminum halides |
| TWI229089B (en) * | 2000-12-12 | 2005-03-11 | Bayer Ag | Halogenated, high molecular weight, gel-free isobutene copolymers with elevated double bond contents |
| RU2212416C2 (ru) * | 2001-01-17 | 2003-09-20 | Открытое акционерное общество "Нижнекамскнефтехим" | Способ получения бромбутилкаучука |
| CA2604409C (en) * | 2006-12-22 | 2015-04-07 | Lanxess Inc. | Butyl rubber ionomer nanocomposites |
| KR101281343B1 (ko) | 2008-07-15 | 2013-07-02 | 란세스 인터내쇼날 에스에이 | 고분자량 할로부틸 고무를 제조하기 위한 공통 용매 방법 |
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- 2011-01-17 IN IN6386DEN2012 patent/IN2012DN06386A/en unknown
- 2011-01-17 EP EP11700540.5A patent/EP2526123B1/en active Active
- 2011-01-17 KR KR1020127021553A patent/KR101473542B1/ko not_active Expired - Fee Related
- 2011-01-17 JP JP2012549322A patent/JP5703311B2/ja not_active Expired - Fee Related
- 2011-01-17 ES ES11700540.5T patent/ES2492521T3/es active Active
- 2011-01-17 SG SG2012052122A patent/SG182530A1/en unknown
- 2011-01-17 WO PCT/EP2011/050529 patent/WO2011089091A1/en active Application Filing
- 2011-01-17 CN CN201180010797.8A patent/CN102770461B/zh not_active Expired - Fee Related
- 2011-01-17 US US13/522,756 patent/US9273160B2/en not_active Expired - Fee Related
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- 2011-01-17 SA SA111320111A patent/SA111320111B1/ar unknown
- 2011-01-17 CA CA2787227A patent/CA2787227C/en active Active
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| EP2526123B1 (en) | 2014-05-21 |
| IN2012DN06386A (h) | 2015-10-02 |
| CA2787227C (en) | 2018-01-16 |
| WO2011089091A1 (en) | 2011-07-28 |
| US20130131281A1 (en) | 2013-05-23 |
| RU2012135379A (ru) | 2014-02-27 |
| JP2013517361A (ja) | 2013-05-16 |
| MY159846A (en) | 2017-02-15 |
| TWI513707B (zh) | 2015-12-21 |
| KR20120107137A (ko) | 2012-09-28 |
| CN102770461B (zh) | 2014-11-05 |
| TW201139465A (en) | 2011-11-16 |
| EP2526123A1 (en) | 2012-11-28 |
| US9273160B2 (en) | 2016-03-01 |
| SG182530A1 (en) | 2012-08-30 |
| RU2584424C2 (ru) | 2016-05-20 |
| JP5703311B2 (ja) | 2015-04-15 |
| KR101473542B1 (ko) | 2014-12-16 |
| CA2787227A1 (en) | 2011-07-28 |
| SA111320111B1 (ar) | 2014-01-17 |
| CN102770461A (zh) | 2012-11-07 |
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