DE69813882T2 - Verfahren zur hydrierung von makromolekularen organischen substraten - Google Patents
Verfahren zur hydrierung von makromolekularen organischen substratenInfo
- Publication number
- DE69813882T2 DE69813882T2 DE69813882T DE69813882T DE69813882T2 DE 69813882 T2 DE69813882 T2 DE 69813882T2 DE 69813882 T DE69813882 T DE 69813882T DE 69813882 T DE69813882 T DE 69813882T DE 69813882 T2 DE69813882 T2 DE 69813882T2
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- process according
- metal
- hydrogenation
- range
- 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.)
- Revoked
Links
- 238000000034 method Methods 0.000 title claims description 49
- 239000000758 substrate Substances 0.000 title claims description 43
- 229910052751 metal Inorganic materials 0.000 claims description 53
- 239000002184 metal Substances 0.000 claims description 53
- 239000003054 catalyst Substances 0.000 claims description 46
- 238000005984 hydrogenation reaction Methods 0.000 claims description 37
- 230000008569 process Effects 0.000 claims description 33
- 239000006260 foam Substances 0.000 claims description 30
- 229920000642 polymer Polymers 0.000 claims description 22
- 239000011148 porous material Substances 0.000 claims description 18
- 239000000463 material Substances 0.000 claims description 12
- 150000002739 metals Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 230000000737 periodic effect Effects 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 7
- 229910044991 metal oxide Inorganic materials 0.000 claims description 7
- 150000004706 metal oxides Chemical class 0.000 claims description 7
- 150000001993 dienes Chemical class 0.000 claims description 6
- 229920001470 polyketone Polymers 0.000 claims description 6
- 239000002243 precursor Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 239000011248 coating agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 239000007787 solid Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001247 metal acetylides Chemical class 0.000 claims description 2
- 150000004767 nitrides Chemical class 0.000 claims description 2
- 229920000515 polycarbonate Polymers 0.000 claims description 2
- 239000004417 polycarbonate Substances 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 33
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 18
- 238000005470 impregnation Methods 0.000 description 13
- 239000000047 product Substances 0.000 description 12
- 229910052759 nickel Inorganic materials 0.000 description 10
- 229920002521 macromolecule Polymers 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical group C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 7
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- 239000005062 Polybutadiene Substances 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- FACXGONDLDSNOE-UHFFFAOYSA-N buta-1,3-diene;styrene Chemical compound C=CC=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 FACXGONDLDSNOE-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229920002857 polybutadiene Polymers 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 6
- 239000000919 ceramic Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- -1 Alkenyl aromatic hydrocarbons Chemical class 0.000 description 4
- 241000264877 Hippospongia communis Species 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 4
- VXAUWWUXCIMFIM-UHFFFAOYSA-M aluminum;oxygen(2-);hydroxide Chemical compound [OH-].[O-2].[Al+3] VXAUWWUXCIMFIM-UHFFFAOYSA-M 0.000 description 4
- 238000001354 calcination Methods 0.000 description 4
- 239000002638 heterogeneous catalyst Substances 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 238000011109 contamination Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical group C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 238000010923 batch production Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000004568 cement Substances 0.000 description 2
- 239000011651 chromium Substances 0.000 description 2
- 208000012839 conversion disease Diseases 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011414 polymer cement Substances 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052707 ruthenium Inorganic materials 0.000 description 2
- 150000003440 styrenes Chemical group 0.000 description 2
- 239000011800 void material Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical group C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- QTTAWIGVQMSWMV-UHFFFAOYSA-N 3,4-dimethylhexa-1,3-diene Chemical compound CCC(C)=C(C)C=C QTTAWIGVQMSWMV-UHFFFAOYSA-N 0.000 description 1
- OCTVDLUSQOJZEK-UHFFFAOYSA-N 4,5-diethylocta-1,3-diene Chemical compound CCCC(CC)C(CC)=CC=C OCTVDLUSQOJZEK-UHFFFAOYSA-N 0.000 description 1
- CJSBUWDGPXGFGA-UHFFFAOYSA-N 4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C CJSBUWDGPXGFGA-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 229920002633 Kraton (polymer) Polymers 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 229910019029 PtCl4 Inorganic materials 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229920005603 alternating copolymer Polymers 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical class [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 239000002815 homogeneous catalyst Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 238000012667 polymer degradation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000037452 priming Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- 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
- C08C19/02—Hydrogenation
-
- 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
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F236/10—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated with vinyl-aromatic monomers
-
- 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G85/00—General processes for preparing compounds provided for in this subclass
- C08G85/004—Modification of polymers by chemical after-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97310322 | 1997-12-19 | ||
| PCT/EP1998/008546 WO1999032529A1 (en) | 1997-12-19 | 1998-12-18 | Process for hydrogenation of macromolecular organic substrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69813882D1 DE69813882D1 (de) | 2003-05-28 |
| DE69813882T2 true DE69813882T2 (de) | 2003-12-11 |
Family
ID=8229677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69813882T Revoked DE69813882T2 (de) | 1997-12-19 | 1998-12-18 | Verfahren zur hydrierung von makromolekularen organischen substraten |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6087455A (https=) |
| EP (1) | EP1040137B1 (https=) |
| JP (1) | JP2002503730A (https=) |
| KR (1) | KR20010033298A (https=) |
| CN (1) | CN1118485C (https=) |
| AU (1) | AU2614699A (https=) |
| BR (1) | BR9813673A (https=) |
| CA (1) | CA2315021A1 (https=) |
| DE (1) | DE69813882T2 (https=) |
| ES (1) | ES2196652T3 (https=) |
| WO (1) | WO1999032529A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187873B1 (en) * | 1997-08-07 | 2001-02-13 | Shell Oil Company | Increased throughput in the manufacture of block copolymers by reduction in polymer cement viscosity through the addition of polar solvents |
| US6790417B2 (en) * | 2000-12-21 | 2004-09-14 | Corning Incorporated | Monolith loop reactors |
| US6762276B2 (en) | 2002-02-27 | 2004-07-13 | Eastman Chemical Company | Hydrogenation of polyester oligomers containing terephthalic acid residues |
| AU2003267270A1 (en) * | 2002-09-25 | 2004-04-19 | Dow Global Technologies Inc. | Improved process for hydrogenating unsaturated polymers |
| JP2009525356A (ja) * | 2006-01-30 | 2009-07-09 | ビーエーエスエフ ソシエタス・ヨーロピア | ポリマーの水素化方法及びそのために好適な水素化触媒 |
| JP2010285468A (ja) * | 2009-06-09 | 2010-12-24 | Bridgestone Corp | 水素化重合体の製造方法、光硬化性樹脂の製造方法、光硬化性樹脂、シール材 |
| ES2613859T3 (es) * | 2012-10-08 | 2017-05-26 | Shell Internationale Research Maatschappij B.V. | Proceso para la licuación de un material celulósico |
| CN116943731B (zh) * | 2022-04-14 | 2025-12-23 | 浙江芳原馨生物医药有限公司 | 一种用于间甲酚连续烷基化的催化剂、其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE389656C (de) * | 1921-04-05 | 1924-02-05 | Siemens & Halske Akt Ges | Verfahren zum Hydrieren von kuenstlichen und natuerlichen Kautschukarten |
| US2152533A (en) * | 1936-08-06 | 1939-03-28 | Neville Co | Hydrogenation of resins |
| US4358566A (en) * | 1976-09-24 | 1982-11-09 | Exxon Research & Engineering Co. | Method for controlling the functionality distribution of liquid copolymers |
| GB2011911B (en) * | 1977-10-20 | 1982-09-15 | Johnson Matthey Co Ltd | Production of stable polymers |
| GB2087403B (en) * | 1977-10-20 | 1983-01-19 | Johnson Matthey Co Ltd | Hydrogenation of polymers |
| JPS5682803A (en) * | 1979-12-08 | 1981-07-06 | Nippon Zeon Co Ltd | Preparation of hydrogenated conjugated polymer |
| NL191511C (nl) * | 1983-01-20 | 1995-08-21 | Unilever Nv | Werkwijze voor de bereiding van een nikkel-bevattende katalysator. |
| EP0233642A3 (en) * | 1986-02-18 | 1989-09-06 | W.R. Grace & Co.-Conn. | Process for hydrogenation of organic compounds |
| US5110779A (en) * | 1989-01-09 | 1992-05-05 | The Dow Chemical Company | Polymer hydrogenation catalysts |
| US5028665A (en) * | 1989-01-09 | 1991-07-02 | The Dow Chemical Company | Polymer hydrogenation catalysts |
| US5206307A (en) * | 1991-09-09 | 1993-04-27 | Shell Oil Company | Process for selective hydrogenation of conjugated diolefin polymers |
| US5378767A (en) * | 1993-06-18 | 1995-01-03 | Shell Oil Company | Fixed bed hydrogenation of low molecular weight polydiene polymers |
| FI962021A7 (fi) * | 1993-11-19 | 1996-07-12 | Parke Davis & Co | 5,6-dihydropyronijohdannaiset proteaasi-inhibiittoreina ja antiviraali sina aineina |
| JPH08277238A (ja) * | 1995-04-04 | 1996-10-22 | Kuraray Co Ltd | シトロネラ−ルの製造方法 |
-
1998
- 1998-12-17 US US09/213,785 patent/US6087455A/en not_active Expired - Fee Related
- 1998-12-18 DE DE69813882T patent/DE69813882T2/de not_active Revoked
- 1998-12-18 ES ES98966920T patent/ES2196652T3/es not_active Expired - Lifetime
- 1998-12-18 KR KR1020007006740A patent/KR20010033298A/ko not_active Ceased
- 1998-12-18 CA CA002315021A patent/CA2315021A1/en not_active Abandoned
- 1998-12-18 CN CN98812433A patent/CN1118485C/zh not_active Expired - Fee Related
- 1998-12-18 BR BR9813673-9A patent/BR9813673A/pt not_active Application Discontinuation
- 1998-12-18 JP JP2000525464A patent/JP2002503730A/ja active Pending
- 1998-12-18 WO PCT/EP1998/008546 patent/WO1999032529A1/en not_active Ceased
- 1998-12-18 AU AU26146/99A patent/AU2614699A/en not_active Abandoned
- 1998-12-18 EP EP98966920A patent/EP1040137B1/en not_active Revoked
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999032529A1 (en) | 1999-07-01 |
| KR20010033298A (ko) | 2001-04-25 |
| BR9813673A (pt) | 2000-10-17 |
| EP1040137B1 (en) | 2003-04-23 |
| AU2614699A (en) | 1999-07-12 |
| CN1118485C (zh) | 2003-08-20 |
| JP2002503730A (ja) | 2002-02-05 |
| US6087455A (en) | 2000-07-11 |
| DE69813882D1 (de) | 2003-05-28 |
| CN1282341A (zh) | 2001-01-31 |
| EP1040137A1 (en) | 2000-10-04 |
| ES2196652T3 (es) | 2003-12-16 |
| CA2315021A1 (en) | 1999-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8363 | Opposition against the patent | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: DERZEIT KEIN VERTRETER BESTELLT |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: STOLMAR SCHEELE & PARTNER, 80331 MUENCHEN |
|
| 8331 | Complete revocation |