TW200406428A - Hydrogenation catalyst for petroleum resin and manufacturing method of hydrogenated petroleum resin - Google Patents
Hydrogenation catalyst for petroleum resin and manufacturing method of hydrogenated petroleum resin Download PDFInfo
- Publication number
- TW200406428A TW200406428A TW092116438A TW92116438A TW200406428A TW 200406428 A TW200406428 A TW 200406428A TW 092116438 A TW092116438 A TW 092116438A TW 92116438 A TW92116438 A TW 92116438A TW 200406428 A TW200406428 A TW 200406428A
- Authority
- TW
- Taiwan
- Prior art keywords
- catalyst
- petroleum resin
- palladium
- platinum
- carrier
- Prior art date
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 100
- 229920005989 resin Polymers 0.000 title claims abstract description 48
- 239000011347 resin Substances 0.000 title claims abstract description 48
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 45
- 239000003208 petroleum Substances 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 58
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 49
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 29
- 229910052697 platinum Inorganic materials 0.000 claims abstract description 24
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000011593 sulfur Substances 0.000 claims abstract description 21
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 ethylene aromatic compound Chemical class 0.000 claims description 12
- 239000005977 Ethylene Substances 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract description 15
- 230000000694 effects Effects 0.000 abstract description 13
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000000034 method Methods 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 229910052759 nickel Inorganic materials 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- 238000011068 loading method Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000010304 firing Methods 0.000 description 3
- 239000010970 precious metal Substances 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- JRTYPQGPARWINR-UHFFFAOYSA-N palladium platinum Chemical compound [Pd].[Pt] JRTYPQGPARWINR-UHFFFAOYSA-N 0.000 description 2
- 229910052703 rhodium Inorganic materials 0.000 description 2
- 239000010948 rhodium Substances 0.000 description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- 239000010457 zeolite Substances 0.000 description 2
- IQSUNBLELDRPEY-UHFFFAOYSA-N 1-ethylcyclopenta-1,3-diene Chemical compound CCC1=CC=CC1 IQSUNBLELDRPEY-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004831 Hot glue Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical group CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 1
- NFWSQSCIDYBUOU-UHFFFAOYSA-N methylcyclopentadiene Chemical compound CC1=CC=CC1 NFWSQSCIDYBUOU-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- DDTIGTPWGISMKL-UHFFFAOYSA-N molybdenum nickel Chemical compound [Ni].[Mo] DDTIGTPWGISMKL-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- GPNDARIEYHPYAY-UHFFFAOYSA-N palladium(ii) nitrate Chemical compound [Pd+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O GPNDARIEYHPYAY-UHFFFAOYSA-N 0.000 description 1
- 239000012169 petroleum derived wax Substances 0.000 description 1
- 235000019381 petroleum wax Nutrition 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- CLSUSRZJUQMOHH-UHFFFAOYSA-L platinum dichloride Chemical compound Cl[Pt]Cl CLSUSRZJUQMOHH-UHFFFAOYSA-L 0.000 description 1
- NWAHZABTSDUXMJ-UHFFFAOYSA-N platinum(2+);dinitrate Chemical compound [Pt+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O NWAHZABTSDUXMJ-UHFFFAOYSA-N 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- DNYWZCXLKNTFFI-UHFFFAOYSA-N uranium Chemical compound [U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U][U] DNYWZCXLKNTFFI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
- B01J29/12—Noble metals
- B01J29/126—Y-type faujasite
-
- 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
- B01J23/44—Palladium
-
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/10—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y containing iron group metals, noble metals or copper
- B01J29/12—Noble metals
-
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G15/00—Cracking of hydrocarbon oils by electric means, electromagnetic or mechanical vibrations, by particle radiation or with gases superheated in electric arcs
- C10G15/10—Cracking of hydrocarbon oils by electric means, electromagnetic or mechanical vibrations, by particle radiation or with gases superheated in electric arcs by particle radiation
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- C10G45/00—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds
- C10G45/02—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing
- C10G45/04—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used
- C10G45/10—Refining of hydrocarbon oils using hydrogen or hydrogen-generating compounds to eliminate hetero atoms without changing the skeleton of the hydrocarbon involved and without cracking into lower boiling hydrocarbons; Hydrofinishing characterised by the catalyst used containing platinum group metals or compounds thereof
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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
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
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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
- 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
- B01J29/00—Catalysts comprising molecular sieves
- B01J29/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites
- B01J29/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- B01J29/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
- B01J29/084—Y-type faujasite
-
- 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
- B01J35/615—100-500 m2/g
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Toxicology (AREA)
- Physics & Mathematics (AREA)
- Electromagnetism (AREA)
- Mechanical Engineering (AREA)
- Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
200406428 (1) 玖、發明說明 【發明所屬之技術領域】 本發明係有關含硫石油樹脂之氫化用觸媒及使用該觸 媒之氫化石油樹脂的製造方法。 【先前技術】 氫化石油樹脂製造所使用之環戊二烯系化合物，乙烯 芳香族系化合物多半使用由石油蠟熱分解等之廢餾份，一 般硫爲含有10〜5 00質量ppm之硫黃者。 此部份硫具有聚合性，因此，環戊二烯系化合物與乙 烯芳香族系化合物之聚合時取入生成石油樹脂，之後之氫 化步驟中，一般所使用之鈀，鉑及鎳等呈氫化觸媒之觸媒 毒，明顯出現觸媒活性之降低。 使用鎳，鎳·鎢及鎳-鉬等鎳系觸媒時，石油樹脂中之 硫或氫化脫硫所生成之硫化氫使鎳金屬呈鎳硫化物，降低氫 化活性。 又，使用鈀，鉑，釕及铑等貴金屬系觸媒時，石油樹 脂中硫或氫化脫硫後所生成之硫化氫吸附於觸媒金屬表面後 ，明顯降低氫化活性。 爲此，一般此等貴金屬系觸媒被認爲耐硫黃性不足者 〇 做爲提高耐硫黃性之氫化觸媒者如：被揭示於特公昭 62-61201號公報中擔載選自鉑及/或铑與鈀，釕及銶金屬之 觸媒，惟，有關各金屬擔載量及金屬比均未詳細記載。 (2) (2)200406428 又，特公昭62-6 1 201號公報被揭示之觸媒（實施例5 ) 爲0.25質量％Pd-1.75質量％Pt/氧化鋁觸媒者，與本發明之觸 媒其組成大爲不同。 本發明鑑於該狀況，而以開發含硫之石油樹脂氫化活 性高，且，觸媒壽命長之觸媒爲課題者。 【發明內容】 本發明者爲解決該課題，進行精密硏討後結果發現， 鈀及鉑所擔載之觸媒，其鈀及鉑之比率及擔載量爲特定觸 媒，含硫石油樹脂之氫化活性高，且，觸媒壽命長之觸媒 者，進而完成本發明。 亦即，本發明係有關 1 .鈀及鉑擔載氧化鋁觸媒者，其鈀/鉑之比率爲含有 2.5〜3.5 (質量比）之硫石油樹脂之氫化觸媒， 2.含有0.3〜3.0質量％之鈀及0.1〜1.0質量％鉑之上記1 含硫石油樹脂氫化觸媒， 3 .石油樹脂爲環戊二烯系化合物與乙烯芳香族系化合 物聚合物之上記1或2所載含硫石油樹脂氫化觸媒， 4. 於上記1或2所載觸媒之存在下，製造氫與含硫石油 樹脂相互接觸之氫化石油樹脂的方法，以及 5. 石油樹脂爲環戊二烯系化合物與乙烯芳香族化合物 聚合物之上記5所載氫化石油樹脂之製造方法者。 【實施方式〕 上'Ό -5- (3) (3)200406428 [發明實施之最佳形態] 本發明鈀-鉑雙金屬觸媒中，其鈀/鉑之擔載質量比以 2.5〜3.5者宜，較佳者爲2.6~3.4者。 呈銷/銷之擔載質量比不足2.5，或超出3 . 5時，均無提昇 觸媒活性之效果。 又，鈀-鉑雙金屬觸媒中鈀之擔載量以0.3〜3.0質量％者 宜’較佳者爲0.3〜1.5質量％。 鉑擔載量以0.1〜1.0質量％者宜，較佳者爲0.1〜0.5質量％ 〇 當銷及鉑之擔載量分別爲不足0.3質量％及不足0.1質量％ 時則無法取得充份之觸媒活性，而分別超出3.0質量％及1.0 質量％時，則使用過量貴金屬造成成本浪費，不實用。 因此，鈀及鉑爲該範圍內時，可控制氫化觸媒活性之 降低，價廉且可安定製造出良好品質之氫化石油樹脂。 做爲載體者如，二氧化矽，氧化鋁，二氧化矽氧化鋁 ’二氧化欽，氧化鋁氧化硼，及沸石類等例，特別又以氧化 銘爲最佳者。 觸媒係準備含有做爲其成份前驅物之化合物類水溶液 (擔載液），將載體浸於擔載液「浸漬法」，噴霧擔載液於 載體「噴塗法」，或準備相當於載體吸水量之擔載液液量， 其總量含於載體「含浸法」等可調製之。 做爲所使用觸媒成份化合物者亦可使用水溶性類之化 合物，如：做爲氯化物之氯化鈀，氯化鉑酸，或做爲硝酸 鹽之硝酸鈀，硝酸鉑，或鈀及鉑之有機化合物類者被使用之 (4) (4)200406428 如：藉由浸漬法調製觸媒時，準備溶解所定量鈀及鉑 化合物之水溶液後，於此溶液中浸漬所定量之氧化鋁載體， 取出之後，進行離液，乾燥燒成後調製觸媒。 氧化銘載體之物性其表面積以5 0 m2 / g以上者宜，較佳者 爲100m2/g以上，乾燥溫度爲1〇〇〜2〇〇°C，燒成爲300〜800°C者 宜，更佳者爲300〜600°C下進行者。 觸媒形狀可使用圓筒狀錠劑，顆粒狀擠出物，或球狀 物均可，惟，由其觸媒活性，壓力損失之觀點視之，又以擴 大觸媒之幾何學表面積之CDS型（Computer Designed Shape )成型品爲最佳者。 當氧化鋁載體表面積爲50m2/g以下時，則觸媒活性將不 足，乾燥溫度爲1 00 °C以下時，則務必長時間乾燥，而不經 濟，又，200 °C以上時，則開始分解所擔載觸媒成份化合物 ，所產生氣體將導致裝置受浸蝕而不理想。 燒成溫度爲300 °C以下時，則所擔載觸媒成份化合物之 分解不足，而，8 00 °C以上則助長觸媒成份之燒結，無法取 得高活性觸媒亦不理想。 本發明觸媒其成份爲鈀，鉑之雙金屬型氧化鋁擔載觸 媒，藉由浸漬法，噴霧法，滲透法等被調製後，對於含硫石 油樹脂之氫化有效者’其成份，含量於本發明所載範圍之 Zugechemi觸媒股份公司製之市販觸媒，T-2657觸媒等亦可 適用於本反應中。 本發明氫化石油樹脂係指於溶媒中聚合環戊二燒系化 -7- (5) (5)200406428 合物與乙烯芳香族系化合物後，更使雙鍵及芳香族核進行部 份或完全氫化之氫化石油樹脂者。 此氫化石油樹脂係做爲粘合於苯乙烯-丁二烯嵌段共聚 物，乙烯-醋酸乙烯酯共聚物等之粘合附與劑所配合做爲熱 熔融型粘合劑被使用者。 做爲環戊二烯系化合物例者如：環戊二烯，甲基環戊 二烯，及乙基環戊二烯之外，此等二量體，共二量體等例者 〇 又，做爲乙烯芳香族系化合物者如：苯乙烯，α -甲基 苯乙烯及乙烯甲苯等例。 做爲聚合溶媒例者如：芳香族系溶媒，萘系溶媒及脂 肪族烴系溶媒等例。 聚合方法可採用連續式及分批式之任意者。 通常，聚合條件以其聚合溫度爲180〜280°C，聚合時間 爲0.5〜10小時者。 反應壓力依其聚合溫度，聚合槽內之原料組成及反應 混合物組成等而變動，一般爲1〜3MPa者。 原料之使用比例通常爲環戊二烯系化合物/乙烯芳香族 系化合物=10 /90〜90/10 (質量比）範圍者。 聚合反應結束後，進行由取得聚合物混合物之溶媒與 低分子量聚合物之分離，回收。 做爲分離低分子量聚合物與溶媒之殘餘聚合物氫化方 法者，可採用連續式及分批式之任意者。 本氫化反應中做爲溶媒者可使用環己烷，乙基環己烷 (6) (6)200406428 ’及一甲基環己烷等脂環式烴基，或未使用溶媒者亦可。 做爲溶媒者以乙基環己烷者宜。 氫化反應溫度通常以1 0 0〜3 0 〇 t者宜，較佳者爲 ]2 0 〜2 8 0 〇C 者。 當溫度太低則無法充份進行氫化反應，反之，溫度太 高則引起石油樹脂之分解，均爲不理想者。 又’氫化反應時間其液空間速度（LHSV )以 〇·1〜lOhf1者宜，較佳者爲0.1〜5hr_]。 氫化反應壓力通常爲1〜lOMPa者宜，較佳者爲2〜8MPa 〇 以下，藉由實施例進行本發明之詳細說明，惟，本發 明未受限於此實施例者。 [觸媒調製I]
進行調製以CDS型氧化鋁做爲載體之雙金屬觸媒A〜C 〇 該方法爲如下所載者。 (觸媒A之調製） 準備表面積]80m2/g，，吸水量〇.6cc/g之CDS型氧化 金呂載體（直徑1 . 6 m m ) 1 0 〇 g者。 另外，做爲載體之觸媒成份擔載液者分別使鈀及鉑含 1.〇°/。，0.34%之氯化鈀與氯化鉑酸調製成20()(^之混合水溶 、)枚。 (7) (7)200406428 將預先準備之lOOgCDS型氧化鋁載體浸漬於此混合水 溶液中，再進行斷液後，於1 1 〇 °C下進行乾燥1整夜。 於電爐中，4 0 (TC下進行燒成乾燥物4小時後，取得觸 媒A 〇 此觸媒之含鈀及鉑之量如表-1所示。 (觸媒B之調製） 觸媒A之調製中分別使成份擔載液之鈀及鉛濃度做成 2.0%，0.68%之外，與觸媒A同法調製觸媒B。 該鈀及鉑之含量如表-1所示。 (觸媒C之調製） 準備表面積1 80m2/g，吸水量〇.6cc/g之CDS型氧化鋁載體 (直徑 1.6mm) 100g。 另外，進行調製做爲載體觸媒成份擔載液之使鈀及鉑 分別含2.0 %，1.0 %之氯化鈀與氯化鉑酸之3 0 c c混合水溶液者 〇 將載體移至噴塗混合器，維持流動狀態，將之前調製 之30cc混合溶液噴塗於載體上。 再於1 1 0 °C下進行乾燥1晚後，電爐中6 0 0 °C下進行燒成4 小時後，調製觸媒C。 其鈀及鉑之含量如表-1所示。 (觸媒調製2 ) -10- (8) (8)200406428 g周製以Y型沸石做爲載體之雙金屬觸媒D。 其方法如以下所載者。 (觸媒D之調整） 準備100g之CDS型Y型沸石載體（直徑].6mm)。 另外’進行調製做爲載體之觸媒成份載體液者使鈀及 銷分別含3.0%，1 ·〇%之氯化鈀與氯化鈾酸之30cc混合水 溶液。 將載體移至噴塗混合器，維持流動狀態，將之前調整 之混合水溶液30cc噴塗於載體上。 再於1 10°C下進行乾燥1晚，於電爐中600 t：下進行燒成4 小時後，取得觸媒D。 該觸媒之fE及舶含量如表-1所示。 [觸媒調製3] 調製以CDS型氧化鋁做爲載體之單—成份觸媒e〜F。 該方法如以下所載者。 (觸媒E之調製） 準備表面積1 80m2/g，吸水量〇.6cc/g之CDS型氧化鋁載體 (直徑 1.6mm ) 100g。 另外調製做爲載體之觸媒成份擔載液，使鈀含1.2%之 氯化鈀之2 0 0 c c混合水溶液者。 將預先準備之]〇 0 g載體浸漬於此水溶液中，再於n 〇 -11 - (9) 200406428 。(：下進行乾燥】晚後’電爐中4 ο 〇 °C下進行燒成4小時後’ 取得觸媒E。 此觸媒之含鈀量如表-1所示。 (觸媒F之調製） 準備1 〇〇g之表面積1 80m2/g，吸水量〇.6cc/g之CDS型氧化 鋁載體（直徑1.6mm )。 另外，調製做爲載體之觸媒成份擔載液，使鈾含2.0 % 之氯化鉑酸3 0 c c混合水溶液。 將載體移至噴塗混合器後，維持流動狀態，將之前調 製之30cc水溶液噴塗於載體。 再於1 1(TC下進行乾燥1晚，電爐中400°C下進行燒成4小 時，取得觸媒F。 該觸媒含鉑量如表-1所示。
表-1 觸媒名 鈀（％ ) 鉛（％ ) A 0.6 0.2 B 1.2 0.4 C 0.6 0.3 D 0.9 0.3 E 0.7 F 一 0.6 -12 - 200406428 do) [實施例u (1 )氫化反應原料之製造（環戊二烯系化合物與乙烯芳香 族系化合物相互之聚合） 局壓鍋中置入1 〇〇質量份之二環戊二烯，1 〇〇質量份之苯乙烯 ’及180質量份之二甲苯，260°C下進行聚合反應6小時。 反應後，藉由脫壓及減壓操作後，去除溶媒之二甲苯及低分 子量聚合物。 針對每100質量份殘留樹脂進行添加3〇〇質量份乙基環己烷溶 解後’更針對樹脂以噻吩做爲硫添加5 〇質量ρρΐΏ後做成氫化 反應用原料。 (2 )氫化石油樹脂之製造 進行該（1 )所調製之氫化反應用原枓的連續氫化。 將觸媒Α塡入外徑1 inch，長度5〇cm之不銹鋼製反應管 後，氫化反應用原料以液空間速度（LHSV ) 411Γ1，針對氫 化反應用原料液之流量以86倍（體積比）氫氣之流量進行流 動，250 °C，4MPa下進行氫化反應後，進行檢測芳香環之氫 化反應率經時變化。 芳香環氫化反應率（％ )=[(原料樹脂中之芳香環含量-氫化樹脂中芳香環含量）/原料樹脂中之芳香環含量]xl 〇〇 (3 )反應成果之評定· 1 g觸媒以5 0g樹脂之份量進行通油，安定狀態下之活 (11) (11)200406428 性芳香環氫化反應率爲3 9 %。 直接持續運轉’觸媒〗g時以]000g份量之樹脂進行通 油後，完全未降低活性。 [實施例2] 除使用觸媒B之外’與實施例1同法進行氫化反應。1 g 觸媒以5 〇g份量樹脂進行通油後，芳香環氫化反應率爲 3 4 %者。 又，1 g觸媒，100 g份量樹脂進行通油後，芳香環氫化 反應率爲3 3 %。 [比較例1 ] 除使用觸媒C之外’與實施例1同法進行氫化反應。 lg觸媒以50 g份量樹脂進行通油後芳香環氫化反應率 爲2 7 %，而，1 g觸媒以1 0 〇 g份量樹脂進行通油後，芳香環 氫化反應率則降至20%。 [比較例2 ] 除使用觸媒D之外，與實施例1同法進行氫化反應。 1 g觸媒以5 0 g份量樹脂進行通油後，芳香環氫化反應 率爲1 2 °/〇，而1 g觸媒以1 0 〇 g份量樹脂進行通油後，芳香環 氫化反應率則降低至9 %。 [比較例3 ] -14、 (12) (12)200406428 除使用觸媒E之外’與實施例1同法進行氫化反應。 ]g觸媒以20g份量樹脂進行通油時之芳香環氫化反應 率爲0 %。 [比較例4] 除使用觸媒F之外，與實施例1同法進行氫化反應。 lg觸媒以50g份量樹脂進行通油後之芳香環氫化反應 率爲1 0 %者。 [產業上可利用率] 本發明觸媒相較於一般所使用之氫化觸媒（鈀，鉑， 隹老及釕等貴金屬單獨觸媒及鎳系觸媒等）其即使於硫黃之 存在下仍具有高度氫化反應活性，因此，可長期安定製造 石油樹脂者。
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Claims (1)
- (1) (1)200406428 拾、申請專利範圍 1 · 一種含硫之石油樹脂的氫化觸媒，其特徵係爲鈀 及銷擔載氧化銘觸媒者，其銷/鉑之比率爲含有2.5〜3 . 5 ( 質量比）之硫。 2. 如申請專利範圍第1項之含硫之石油樹脂的氫化觸 媒’其中該觸媒爲含有〇 . 3〜3 · 〇質量％之鈀，及〇」〜1 . 〇質量％ 之鉑者。 3. 如申請專利範圍第〗項或第2項之含硫之石油樹脂的 氫化樹脂’其中該石油樹脂爲環戊二烯系化合物與乙烯芳香 族系化合物之聚合物者。 4. 一種氫化石油樹脂之製造方法，其特徵係於如申請 專利範圍第1項或第2項之觸媒存在下，使氫與含硫之石油樹 脂相互接觸者。 5 ·如申請專利範圍第4項之氫化石油樹脂之製造方法， 其中該石油樹脂爲環戊二烯系化合物與乙烯芳香族化合物之 聚合物者。
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|---|---|
| TW200406428A true TW200406428A (en) | 2004-05-01 |
| TWI346121B TWI346121B (zh) | 2011-08-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW092116438A TW200406428A (en) | 2002-06-18 | 2003-06-17 | Hydrogenation catalyst for petroleum resin and manufacturing method of hydrogenated petroleum resin |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20050228143A1 (zh) |
| EP (1) | EP1552881B1 (zh) |
| JP (1) | JP4481554B2 (zh) |
| KR (1) | KR20050010940A (zh) |
| CN (1) | CN1662301A (zh) |
| TW (1) | TW200406428A (zh) |
| WO (1) | WO2003106019A1 (zh) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2469789C2 (ru) * | 2007-08-27 | 2012-12-20 | Шелл Интернэшнл Рисерч Маатсхаппий Б.В. | Катализатор гидрирования ароматических углеводородов и способ получения и применения такого катализатора |
| CN103386302B (zh) * | 2013-07-25 | 2015-04-08 | 中国石油化工股份有限公司 | 一种石油树脂加氢催化剂及其制备方法 |
| KR102327050B1 (ko) * | 2017-12-29 | 2021-11-15 | 한화솔루션 주식회사 | 선택적 수소화 방법 |
| KR20200139140A (ko) * | 2018-03-28 | 2020-12-11 | 마루젠 세끼유가가꾸 가부시키가이샤 | 수소 첨가 석유 수지의 제조 방법 |
| EP3978539A4 (en) * | 2019-06-03 | 2023-07-05 | Hanwha Solutions Corporation | PROCESS FOR PRODUCTION OF HYDROGENATED PETROLEUM RESIN |
| KR102424826B1 (ko) * | 2019-06-03 | 2022-07-25 | 한화솔루션 주식회사 | 수첨 석유수지의 제조 방법 |
| KR20210001783A (ko) | 2019-06-28 | 2021-01-06 | 한화솔루션 주식회사 | 수소화반응용 니켈 촉매 및 그 제조방법 |
| KR20210001784A (ko) * | 2019-06-28 | 2021-01-06 | 한화솔루션 주식회사 | 수소화반응용 촉매 및 그 제조방법 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4540480A (en) * | 1982-10-23 | 1985-09-10 | Arakawa Kagaku Kogyo Kabushiki Kaisha | Process for preparing hydrogenated petroleum resin |
| FR2614295B1 (fr) * | 1987-04-22 | 1989-08-04 | Inst Francais Du Petrole | Procede d'isomerisation du butene-1 en butenes-2 dans une coupe d'hydrocarbures en c4 contenant du butadiene et des composes sulfures. |
| JPH0651740B2 (ja) * | 1988-11-07 | 1994-07-06 | 丸善石油化学株式会社 | 粘接着特性の優れた水添石油樹脂の製造方法 |
| US5151172A (en) * | 1991-05-03 | 1992-09-29 | Amoco Corporation | Distillate hydrogenation |
| EP0947248B1 (de) * | 1998-02-06 | 2003-02-12 | KataLeuna GmbH Catalysts | Katalysator zur Hydrierung von Aromaten in schwefelhaltigen Kohlenwasserstofffraktionen |
-
2002
- 2002-06-18 JP JP2002176585A patent/JP4481554B2/ja not_active Expired - Lifetime
-
2003
- 2003-06-16 CN CN038144190A patent/CN1662301A/zh active Pending
- 2003-06-16 EP EP03733439.8A patent/EP1552881B1/en not_active Expired - Lifetime
- 2003-06-16 US US10/516,931 patent/US20050228143A1/en not_active Abandoned
- 2003-06-16 WO PCT/JP2003/007611 patent/WO2003106019A1/ja active Application Filing
- 2003-06-16 KR KR10-2004-7020486A patent/KR20050010940A/ko not_active Application Discontinuation
- 2003-06-17 TW TW092116438A patent/TW200406428A/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1552881A4 (en) | 2009-12-30 |
| TWI346121B (zh) | 2011-08-01 |
| EP1552881B1 (en) | 2014-03-12 |
| EP1552881A1 (en) | 2005-07-13 |
| KR20050010940A (ko) | 2005-01-28 |
| JP2004016946A (ja) | 2004-01-22 |
| US20050228143A1 (en) | 2005-10-13 |
| WO2003106019A1 (ja) | 2003-12-24 |
| CN1662301A (zh) | 2005-08-31 |
| JP4481554B2 (ja) | 2010-06-16 |
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