JPH11504959A - 芳香族ポリマーの水素化法 - Google Patents
芳香族ポリマーの水素化法Info
- Publication number
- JPH11504959A JPH11504959A JP8533327A JP53332796A JPH11504959A JP H11504959 A JPH11504959 A JP H11504959A JP 8533327 A JP8533327 A JP 8533327A JP 53332796 A JP53332796 A JP 53332796A JP H11504959 A JPH11504959 A JP H11504959A
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- silica
- hydrogenation
- styrene
- aromatic
- 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.)
- Granted
Links
- 229920000642 polymer Polymers 0.000 title claims abstract description 148
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 119
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 102
- 239000011148 porous material Substances 0.000 claims abstract description 249
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 171
- 238000000034 method Methods 0.000 claims abstract description 143
- 239000003054 catalyst Substances 0.000 claims abstract description 136
- 239000000377 silicon dioxide Substances 0.000 claims abstract description 83
- 229910052751 metal Inorganic materials 0.000 claims abstract description 66
- 239000002184 metal Substances 0.000 claims abstract description 66
- 238000009826 distribution Methods 0.000 claims abstract description 41
- 230000008569 process Effects 0.000 claims abstract description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 56
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 52
- 239000003795 chemical substances by application Substances 0.000 claims description 40
- 229920001577 copolymer Polymers 0.000 claims description 40
- 229910052697 platinum Inorganic materials 0.000 claims description 31
- 239000004793 Polystyrene Substances 0.000 claims description 29
- 229920002223 polystyrene Polymers 0.000 claims description 29
- 229910052703 rhodium Inorganic materials 0.000 claims description 27
- 239000010948 rhodium Substances 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 22
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 22
- 229920001971 elastomer Polymers 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- 239000005060 rubber Substances 0.000 claims description 21
- 239000000178 monomer Substances 0.000 claims description 19
- 229920002554 vinyl polymer Polymers 0.000 claims description 19
- -1 ethylene, propylene, maleic anhydride Chemical class 0.000 claims description 15
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 14
- 229920001400 block copolymer Polymers 0.000 claims description 14
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 claims description 13
- 150000002825 nitriles Chemical class 0.000 claims description 13
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 12
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 229910052763 palladium Inorganic materials 0.000 claims description 12
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
- 229910017052 cobalt Inorganic materials 0.000 claims description 11
- 239000010941 cobalt Substances 0.000 claims description 11
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 11
- 229910052759 nickel Inorganic materials 0.000 claims description 11
- 229910052707 ruthenium Inorganic materials 0.000 claims description 11
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical class C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 claims description 10
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical class C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 claims description 10
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 claims description 10
- 230000009477 glass transition Effects 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 6
- 229920001519 homopolymer Polymers 0.000 claims description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 239000012279 sodium borohydride Substances 0.000 claims description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 90
- 238000002459 porosimetry Methods 0.000 description 66
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 63
- 229910052753 mercury Inorganic materials 0.000 description 63
- 229910052757 nitrogen Inorganic materials 0.000 description 45
- 238000003795 desorption Methods 0.000 description 35
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 10
- 229920003048 styrene butadiene rubber Polymers 0.000 description 10
- 239000002174 Styrene-butadiene Substances 0.000 description 9
- 239000011115 styrene butadiene Substances 0.000 description 9
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 8
- 229920000428 triblock copolymer Polymers 0.000 description 8
- 238000002835 absorbance Methods 0.000 description 7
- 239000003349 gelling agent Substances 0.000 description 7
- 238000001354 calcination Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- 239000004111 Potassium silicate Substances 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- NNHHDJVEYQHLHG-UHFFFAOYSA-N potassium silicate Chemical compound [K+].[K+].[O-][Si]([O-])=O NNHHDJVEYQHLHG-UHFFFAOYSA-N 0.000 description 5
- 229910052913 potassium silicate Inorganic materials 0.000 description 5
- 235000019353 potassium silicate Nutrition 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- HIBWGGKDGCBPTA-UHFFFAOYSA-N C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 Chemical compound C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 HIBWGGKDGCBPTA-UHFFFAOYSA-N 0.000 description 4
- 241000255925 Diptera Species 0.000 description 4
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 4
- 240000001812 Hyssopus officinalis Species 0.000 description 4
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000001186 cumulative effect Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 239000010931 gold Substances 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- 238000005470 impregnation Methods 0.000 description 4
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 230000000379 polymerizing effect Effects 0.000 description 4
- ZAKVZVDDGSFVRG-UHFFFAOYSA-N prop-1-en-2-ylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CC(=C)C1=CC=CC=C1 ZAKVZVDDGSFVRG-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 229910052709 silver Inorganic materials 0.000 description 4
- 239000004332 silver Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000012937 correction Methods 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000012667 polymer degradation Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000005245 sintering Methods 0.000 description 3
- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000004847 absorption spectroscopy Methods 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000004570 mortar (masonry) Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000001374 small-angle light scattering Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000391 vinyl group Chemical class [H]C([*])=C([H])[H] 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MLRVZFYXUZQSRU-UHFFFAOYSA-N 1-chlorohexane Chemical compound CCCCCCCl MLRVZFYXUZQSRU-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- 239000004809 Teflon Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- MOOAHMCRPCTRLV-UHFFFAOYSA-N boron sodium Chemical compound [B].[Na] MOOAHMCRPCTRLV-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- AFABGHUZZDYHJO-UHFFFAOYSA-N dimethyl butane Natural products CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- BXOUVIIITJXIKB-UHFFFAOYSA-N ethene;styrene Chemical group C=C.C=CC1=CC=CC=C1 BXOUVIIITJXIKB-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000007210 heterogeneous catalysis Methods 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 238000002356 laser light scattering Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910001510 metal chloride Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RLQWHDODQVOVKU-UHFFFAOYSA-N tetrapotassium;silicate Chemical compound [K+].[K+].[K+].[K+].[O-][Si]([O-])([O-])[O-] RLQWHDODQVOVKU-UHFFFAOYSA-N 0.000 description 1
Classifications
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/06—Silicon, titanium, zirconium or hafnium; Oxides or hydroxides thereof
- B01J21/08—Silica
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/42—Platinum
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
- B01J23/464—Rhodium
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
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- 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
- C08F8/04—Reduction, e.g. hydrogenation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/75—Cobalt
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
- B01J23/755—Nickel
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J35/00—Catalysts, in general, characterised by their form or physical properties
- B01J35/60—Catalysts, in general, characterised by their form or physical properties characterised by their surface properties or porosity
- B01J35/61—Surface area
- B01J35/613—10-100 m2/g
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- B—PERFORMING OPERATIONS; TRANSPORTING
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Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.芳香族ポリマーを水素化する方法であって、該芳香族ポリマーをシリカ担 持金属水素化触媒の存在下で、少なくとも80%の芳香族水素化を達成するよう に、水素化剤と接触させることを含む芳香族ポリマーの水素化法において、該シ リカが、少なくとも10m2/gの表面積、および該細孔容積の少なくとも98 %が600オングストロームを上回る直径を有する細孔によって形成されるよう な細孔サイズ分布を有することを特徴とする方法。 2.該水素化剤が水素、ヒドラジン、および水素化ホウ素ナトリウムから選ば れる請求項1記載の方法。 3.該水素化剤が水素である請求項2記載の方法。 4.該金属がコバルト、ニッケル、ルテニウム、ロジウム、パラジウム、白金 またはこれらの混合物である請求項1記載の方法。 5.該金属が白金またはロジウムである請求項1記載の方法。 6.該細孔が3000ないし5000オングストロームの平均直径を有する請 求項1記載の方法。 7.該表面積が10ないし50m2/gである請求項6記載の方法。 8.触媒対ポリマーの該重量比が0.5以下である請求項1記載の方法。 9.芳香族ポリマー5,000ないし200,000重量部当たり1重量部の 触媒を存在させる請求項8記載の方法。 10.該芳香族ポリマーがポリスチレンである請求項1記載の方法。 11.該芳香族ポリマーの該Mwが100,000ないし3,000,000 である請求項1記載の方法。 12.該水素化反応が50ないし250℃の温度で行われる請求項1記載の方 法。 13.ポリアルファメチルスチレン、スチレンアルファメチルスチレンコポリ マーならびにビニル芳香族モノマーとニトリル、アクリレート、酸、エチレン、 プロピレン、無水マレイン酸、マレイミド、酢酸ビニルおよび塩化ビニルよりな る群から選ばれるモノマーとのコポリマーから選ばれる芳香族ポリマーの水素化 法であって、シリカ担持金属水素化触媒の存在下で該芳香族ポリマーを水素化剤 と接触させる方法において、該シリカが、少なくとも10m2/gの表面積、お よび該細孔容積の少なくとも98%が600オングストロームを上回る直径を有 する細孔によって形成されるような細孔サイズ分布を有することを特徴とする方 法。 14.シリカ担持金属触媒であって、該シリカが、少なくとも10m2/gの 表面積、および該細孔サイズの少なくとも98%が600オングストロームを上 回る直径を有する細孔によって形成されるような細孔サイズ分布を有することを 特徴とする触媒。 15.該表面積が10ないし50m2/gである請求項14記載の触媒。 16.該金属がコバルト、ニッケル、ルテニウム、ロジウム、パラジウム、白 金またはこれらの混合物である請求項14記載の触媒。 17.該金属が白金またはロジウムである請求項16記載の触媒。 18.該細孔が3000ないし5000オングストロームの平均直径を有する 請求項14記載の触媒。 19.請求項1記載の方法によって調製した水素化ポリスチレンポリマー。 20.ガラス転移点(DSCにより3℃/分の加熱速度で測定)が少なくとも 141℃である水素化ポリスチレンポリマー。 21.請求項1記載の方法によって調製した水素化スチレンアルファメチルス チレンコポリマー。 22.請求項1記載の方法によって調製した水素化スチレンブタジエンまたは スチレンイソプレンブロックコポリマー。 23.請求項1の方法によって調製した水素化スチレンブタジエンスチレンま たはスチレンイソプレンスチレントリブロックコポリマー。 24.請求項1記載の方法によって調製した耐衝撃性改良グラフトゴム含有水 素化芳香族ポリマー。 25.ビニル芳香族モノマーと、ニトリル、アクリレート、酸、エチレン、プ ロピレン、無水マレイン酸、マレイミド、酢酸ビニルおよび塩化ビニルよりなる 群から選ばれるコモノマーとの水素化コポリマー。 26.ビニル芳香族ポリマーとアクリロニトリルとの水素化コポリマー。 27.アルファメチルスチレンの水素化ホモポリマー。 28.少なくとも10%の芳香族水素化を有する水素化芳香族スターブロック コポリマー。 29.該コポリマーがスチレンとブタジエンとのコポリマーである請求項28 記載のスターブロックコポリマー。 30.少なくとも10%の芳香族水素化が得られる請求項1記載の水素化芳香 族スターブロックコポリマー。 31.少なくとも25%の水素化が得られる請求項30記載の水素化スターブ ロックコポリマー。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US08/434,636 US5612422A (en) | 1995-05-04 | 1995-05-04 | Process for hydrogenating aromatic polymers |
US08/434,636 | 1995-05-04 | ||
PCT/US1996/005240 WO1996034896A1 (en) | 1995-05-04 | 1996-04-16 | A process for hydrogenating aromatic polymers |
Publications (2)
Publication Number | Publication Date |
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JPH11504959A true JPH11504959A (ja) | 1999-05-11 |
JP4111540B2 JP4111540B2 (ja) | 2008-07-02 |
Family
ID=23725021
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP53332796A Expired - Lifetime JP4111540B2 (ja) | 1995-05-04 | 1996-04-16 | 芳香族ポリマーの水素化法 |
Country Status (14)
Country | Link |
---|---|
US (3) | US5612422A (ja) |
EP (2) | EP0842698B1 (ja) |
JP (1) | JP4111540B2 (ja) |
CN (2) | CN1117103C (ja) |
AU (1) | AU703098B2 (ja) |
BR (1) | BR9608697A (ja) |
CA (1) | CA2217207A1 (ja) |
CO (1) | CO4560454A1 (ja) |
DE (2) | DE69602743T2 (ja) |
ES (1) | ES2132918T3 (ja) |
HK (1) | HK1008229A1 (ja) |
MX (1) | MX9708469A (ja) |
TW (1) | TW419488B (ja) |
WO (1) | WO1996034896A1 (ja) |
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JP2003502470A (ja) * | 1999-06-11 | 2003-01-21 | ザ ダウ ケミカル カンパニー | 水素添加ブロック共重合体からなる組成物及びその最終用途への利用 |
JP2003506513A (ja) * | 1999-07-28 | 2003-02-18 | ザ ダウ ケミカル カンパニー | 弾性を有する水素添加ブロック重合体およびそれから得られる物品 |
JP2003516437A (ja) * | 1999-12-08 | 2003-05-13 | ダウ グローバル テクノロジーズ インコーポレーテッド | 不飽和ポリマー特に芳香族ポリマーを水素化する方法 |
JP2003516438A (ja) * | 1999-12-08 | 2003-05-13 | ダウ グローバル テクノロジーズ インコーポレーテッド | 不飽和ポリマーを水素化する方法 |
JP2003528182A (ja) * | 2000-03-23 | 2003-09-24 | ダウ グローバル テクノロジーズ インコーポレーテッド | 水素化モノビニリデン芳香族ポリマー組成物 |
US7488782B2 (en) | 2006-02-27 | 2009-02-10 | Mitsubishi Gas Chemical Company, Inc. | Process for producing hydrogenated polymers |
WO2009020096A1 (ja) | 2007-08-06 | 2009-02-12 | Mitsubishi Gas Chemical Company, Inc. | 核水素化された芳香族ビニル化合物/(メタ)アクリレート系共重合体の製造方法 |
US8575277B2 (en) | 2007-08-06 | 2013-11-05 | Mitsubishi Gas Chemical Company, Inc. | Process for production of nucleus-hydrogenated aromatic vinyl/(meth)acrylate copolymers |
Also Published As
Publication number | Publication date |
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BR9608697A (pt) | 1999-07-06 |
AU5548796A (en) | 1996-11-21 |
AU703098B2 (en) | 1999-03-18 |
TW419488B (en) | 2001-01-21 |
CN1117103C (zh) | 2003-08-06 |
ES2132918T3 (es) | 1999-08-16 |
CN1403490A (zh) | 2003-03-19 |
EP0842698A2 (en) | 1998-05-20 |
EP0823916A1 (en) | 1998-02-18 |
HK1008229A1 (en) | 1999-05-07 |
DE69628304D1 (de) | 2003-06-26 |
CN1177866C (zh) | 2004-12-01 |
CO4560454A1 (es) | 1998-02-10 |
EP0823916B1 (en) | 1999-06-02 |
US5700878A (en) | 1997-12-23 |
CN1183787A (zh) | 1998-06-03 |
CA2217207A1 (en) | 1996-11-07 |
EP0842698A3 (en) | 2001-01-17 |
DE69628304T2 (de) | 2004-04-01 |
WO1996034896A1 (en) | 1996-11-07 |
DE69602743D1 (de) | 1999-07-08 |
US5612422A (en) | 1997-03-18 |
EP0842698B1 (en) | 2003-05-21 |
MX9708469A (es) | 1998-02-28 |
JP4111540B2 (ja) | 2008-07-02 |
DE69602743T2 (de) | 1999-10-07 |
US5654253A (en) | 1997-08-05 |
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