JP7352631B2 - 水素化反応用触媒及びこれの製造方法 - Google Patents
水素化反応用触媒及びこれの製造方法 Download PDFInfo
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- JP7352631B2 JP7352631B2 JP2021531728A JP2021531728A JP7352631B2 JP 7352631 B2 JP7352631 B2 JP 7352631B2 JP 2021531728 A JP2021531728 A JP 2021531728A JP 2021531728 A JP2021531728 A JP 2021531728A JP 7352631 B2 JP7352631 B2 JP 7352631B2
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- catalyst
- hydrogenation reaction
- weight
- nickel
- hydrogenation
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- 239000003054 catalyst Substances 0.000 title claims description 116
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 95
- 238000004519 manufacturing process Methods 0.000 title description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 133
- 229920005989 resin Polymers 0.000 claims description 68
- 239000011347 resin Substances 0.000 claims description 68
- 239000003208 petroleum Substances 0.000 claims description 59
- 229910052759 nickel Inorganic materials 0.000 claims description 55
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 40
- 230000009467 reduction Effects 0.000 claims description 32
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 25
- 239000011593 sulfur Substances 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 239000010949 copper Substances 0.000 claims description 21
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 19
- 229910052802 copper Inorganic materials 0.000 claims description 19
- 239000000377 silicon dioxide Substances 0.000 claims description 19
- 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 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000002245 particle Substances 0.000 claims description 18
- 150000001336 alkenes Chemical class 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 238000004458 analytical method Methods 0.000 claims description 14
- 239000000376 reactant Substances 0.000 claims description 11
- 239000007809 chemical reaction catalyst Substances 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 9
- 239000013032 Hydrocarbon resin Substances 0.000 claims description 7
- 238000009826 distribution Methods 0.000 claims description 7
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- 238000001179 sorption measurement Methods 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 3
- 238000001420 photoelectron spectroscopy Methods 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 2
- 230000000694 effects Effects 0.000 description 24
- 238000000034 method Methods 0.000 description 19
- 239000011148 porous material Substances 0.000 description 14
- 238000001556 precipitation Methods 0.000 description 13
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 8
- 239000002243 precursor Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000010304 firing Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 229910052979 sodium sulfide Inorganic materials 0.000 description 5
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 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 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 230000005180 public health Effects 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- -1 ethylene, propylene, butylene Chemical group 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000003841 chloride salts Chemical class 0.000 description 2
- 229910000365 copper sulfate Inorganic materials 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000000151 deposition Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
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- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
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- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RRKODOZNUZCUBN-CCAGOZQPSA-N (1z,3z)-cycloocta-1,3-diene Chemical compound C1CC\C=C/C=C\C1 RRKODOZNUZCUBN-CCAGOZQPSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000012691 Cu precursor Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229920005601 base polymer Polymers 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012018 catalyst precursor Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001483 mobilizing effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910000652 nickel hydride Inorganic materials 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000002352 steam pyrolysis Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- WWNBZGLDODTKEM-UHFFFAOYSA-N sulfanylidenenickel Chemical compound [Ni]=S WWNBZGLDODTKEM-UHFFFAOYSA-N 0.000 description 1
- 238000004227 thermal cracking Methods 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F32/00—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system
- C08F32/08—Homopolymers and copolymers of cyclic compounds having no unsaturated aliphatic radicals in a side chain, and having one or more carbon-to-carbon double bonds in a carbocyclic ring system having two condensed rings
-
- 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
- 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
- C10G45/06—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 nickel or cobalt metal, or compounds thereof
-
- 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
- C10G47/00—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions
- C10G47/02—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used
- C10G47/10—Cracking of hydrocarbon oils, in the presence of hydrogen or hydrogen- generating compounds, to obtain lower boiling fractions characterised by the catalyst used with catalysts deposited on a carrier
- C10G47/12—Inorganic carriers
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Description
(特許文献2)米国特許公報である第4956328号(1990.4.11)
(特許文献3)日本登録特許公報第4958545号(2012.3.30)
(特許文献4)(非特許文献4)RUSS.CHEM.BULL.,INTERNATIONAL EDITION, VOL.65, NO.12, PP.2841-2844 (2016.11)
300m2/gの表面積と28nmの気孔サイズを持つ多孔性シリカ粉末40g、硫酸ニッケル491g、硫酸銅6g及び蒸留水2000mLを沈殿容器に入れて攪拌しながら80℃に昇温した。80℃ 到達後炭酸ナトリウム262gと硫化ナトリウム19.1gが含まれた溶液1500mLをsyringe pumpを利用して1時間以内全て注入した。沈殿完了後スラリーのpHは7.6であり、これを約15Lの蒸留水で洗浄及び濾過した後乾燥オーブンを利用して100℃で12時間以上乾燥した。これを小分けした後 空気雰囲気で400℃の温度で焼成した。又これを小分けした後水素雰囲気で400℃の温度で還元した。還元後粉末を1%酸素が含まれた窒素混合ガスを利用して不動態化して水素化触媒を製造した。
水添触媒の硫黄/ニッケル重量比4.3%になるように沈殿剤である炭酸ナトリウム262g、硫化ナトリウム17gが含まれた溶液1500mLをsyringe pumpを利用して1時間以内全て注入した。沈殿完了後スラリーのpHは7.7であった。洗浄及び濾過、乾燥等残りの方法は実施例1と同一な方法で製造した。
水添触媒の硫黄/ニッケル重量比3.8%になるように沈殿剤である炭酸ナトリウム262g、硫化ナトリウム15gが含まれた溶液1500mLをsyringe pumpを利用して1時間以内全て注入した。沈殿完了後スラリーのpHは7.5であった。洗浄及び濾過、乾燥等残りの方法は実施例1と同一な方法で製造した。
硫黄を含まない典型的である水添触媒を製造した。実施例1と同一な方法で製造したし、硫化ナトリウムは使用しなかった。
Hollow shaft攪拌機を含めて1600rpmの攪拌速度を持つ300mlオートクレーブを利用した。非水添石油樹脂をExxsolTM D40に30重量%で溶解した溶液75gを230℃、H2 90 barで石油樹脂質量対比1~2%触媒(Catal/DCPD resin)を添加して1時間水素化したし、水添後石油樹脂溶液の色はASTMD1209で測定した。
Claims (9)
- 担体を含む総乾燥重量100重量部に対して、ニッケル40~80重量部、銅0.01~5重量部、硫黄1~10重量部及びシリカ担体10~60重量部を含む水素化反応用触媒であって、 前記水素化反応用触媒はニッケル還元度が90%以上であり、
前記ニッケルの結晶は平均サイズが3~10nmであり、
前記触媒の比表面積は150~300m 2 /gであり、
前記ニッケル還元度はH 2 -TPR(Hydrogen-Temperature ProgramReduction)によって測定され、そして、
前記水素化反応の反応物は石油樹脂(hydrocarbon resin)であることを特徴とする、水素化反応用触媒。 - 触媒粒度分布は平均粒子サイズが3μm~10μmであり、1μm以下サイズの粒子比率が10容量%以下であることを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記触媒は水素-化学吸着(H2-chemisorption)測定によって、試料重量あたりの水素吸着量が0.01~0.3(mmol-H2/g-触媒)であることを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記触媒は、光電子分光器(XPS,X-ray photoelectron Spectroscopy)分析を通じて159~166 eV(結合エネルギー,Bonding energy)の範囲でNi-S結合による電子吸収ピークを持つことを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記水素化反応は芳香族と比較してオレフィンに対する選択度が高いことを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記水素化反応の反応物はジシクロペンタジエン(dicyclopentadiene、DCPD)を含む石油樹脂(hydrocarbon resin)であることを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記水素化反応の反応物はC5留分を含む石油樹脂(hydrocarbon resin)であることを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記水素化反応の反応物はC9留分を含む石油樹脂(hydrocarbon resin)であることを特徴とする、請求項1に記載の水素化反応用触媒。
- 前記触媒は粉末、粒子及び顆粒形態から選択される何れか一つ以上であることを特徴とする、請求項1に記載の水素化反応用触媒。
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JP7292426B2 (ja) * | 2019-06-03 | 2023-06-16 | ハンワ ソリューションズ コーポレイション | 水添石油樹脂の製造方法 |
KR20210001783A (ko) * | 2019-06-28 | 2021-01-06 | 한화솔루션 주식회사 | 수소화반응용 니켈 촉매 및 그 제조방법 |
KR102528310B1 (ko) * | 2019-06-28 | 2023-05-02 | 한화솔루션 주식회사 | 수소화반응용 촉매 및 이의 제조방법 |
KR20210001784A (ko) | 2019-06-28 | 2021-01-06 | 한화솔루션 주식회사 | 수소화반응용 촉매 및 그 제조방법 |
KR20210001781A (ko) * | 2019-06-28 | 2021-01-06 | 한화솔루션 주식회사 | 수소화 반응용 촉매 및 이의 제조방법 |
KR20220082573A (ko) * | 2020-12-10 | 2022-06-17 | 한화솔루션 주식회사 | 수첨 석유수지의 연속적 제조 방법 |
KR102687289B1 (ko) * | 2020-12-10 | 2024-07-19 | 한화솔루션 주식회사 | 수첨 석유수지의 연속적 제조 방법 |
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KR102489090B1 (ko) * | 2021-04-22 | 2023-01-16 | 인천대학교 산학협력단 | 지지체 위 고분자층 형성을 이용한 탄소껍질을 가진 금속 나노입자의 제조방법 |
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