JP3002756B2 - 反応器への装入前に有機化合物が組込まれている担持金属をベースとする触媒の存在下における、蒸気クラッキングガソリン中のジオレフィンの選択的水素化方法 - Google Patents
反応器への装入前に有機化合物が組込まれている担持金属をベースとする触媒の存在下における、蒸気クラッキングガソリン中のジオレフィンの選択的水素化方法Info
- Publication number
- JP3002756B2 JP3002756B2 JP3172332A JP17233291A JP3002756B2 JP 3002756 B2 JP3002756 B2 JP 3002756B2 JP 3172332 A JP3172332 A JP 3172332A JP 17233291 A JP17233291 A JP 17233291A JP 3002756 B2 JP3002756 B2 JP 3002756B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- sulfur
- organic
- reactor
- formula
- 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.)
- Expired - Lifetime
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 75
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 18
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 5
- 239000002184 metal Substances 0.000 title claims description 7
- 229910052751 metal Inorganic materials 0.000 title claims description 7
- 150000001993 dienes Chemical class 0.000 title abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 31
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 239000011593 sulfur Substances 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 230000004913 activation Effects 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 7
- 125000000962 organic group Chemical group 0.000 claims description 7
- 238000004230 steam cracking Methods 0.000 claims description 6
- 150000003568 thioethers Chemical class 0.000 claims description 5
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 1
- 150000008116 organic polysulfides Chemical class 0.000 claims 1
- 150000003573 thiols Chemical group 0.000 claims 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 21
- -1 olefin compounds Chemical class 0.000 description 14
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- UBJVUCKUDDKUJF-UHFFFAOYSA-N Diallyl sulfide Chemical compound C=CCSCC=C UBJVUCKUDDKUJF-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- BZYUMXXOAYSFOW-UHFFFAOYSA-N 2,3-dimethylthiophene Chemical compound CC=1C=CSC=1C BZYUMXXOAYSFOW-UHFFFAOYSA-N 0.000 description 3
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 3
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000005077 polysulfide Substances 0.000 description 3
- 229920001021 polysulfide Polymers 0.000 description 3
- 150000008117 polysulfides Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 description 2
- XJIRSLHMKBUGMR-UHFFFAOYSA-N 1-ethylsulfanylbutane Chemical compound CCCCSCC XJIRSLHMKBUGMR-UHFFFAOYSA-N 0.000 description 2
- JCCCMAAJYSNBPR-UHFFFAOYSA-N 2-ethylthiophene Chemical compound CCC1=CC=CS1 JCCCMAAJYSNBPR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- KCOYHFNCTWXETP-UHFFFAOYSA-N (carbamothioylamino)thiourea Chemical compound NC(=S)NNC(N)=S KCOYHFNCTWXETP-UHFFFAOYSA-N 0.000 description 1
- YGKHJWTVMIMEPQ-UHFFFAOYSA-N 1,2-propanedithiol Chemical compound CC(S)CS YGKHJWTVMIMEPQ-UHFFFAOYSA-N 0.000 description 1
- JBYHSSAVUBIJMK-UHFFFAOYSA-N 1,4-oxathiane Chemical compound C1CSCCO1 JBYHSSAVUBIJMK-UHFFFAOYSA-N 0.000 description 1
- ZOASGOXWEHUTKZ-UHFFFAOYSA-N 1-(Methylthio)-propane Chemical compound CCCSC ZOASGOXWEHUTKZ-UHFFFAOYSA-N 0.000 description 1
- UPYPTOCXMIWHSG-UHFFFAOYSA-N 1-dodecylsulfanyldodecane Chemical group CCCCCCCCCCCCSCCCCCCCCCCCC UPYPTOCXMIWHSG-UHFFFAOYSA-N 0.000 description 1
- NXCKJENHTITELM-UHFFFAOYSA-N 1-nitro-2-[(2-nitrophenyl)disulfanyl]benzene Chemical compound [O-][N+](=O)C1=CC=CC=C1SSC1=CC=CC=C1[N+]([O-])=O NXCKJENHTITELM-UHFFFAOYSA-N 0.000 description 1
- OIWIYLWZIIJNHU-UHFFFAOYSA-N 1-sulfanylpyrazole Chemical compound SN1C=CC=N1 OIWIYLWZIIJNHU-UHFFFAOYSA-N 0.000 description 1
- KYNFOMQIXZUKRK-UHFFFAOYSA-N 2,2'-dithiodiethanol Chemical compound OCCSSCCO KYNFOMQIXZUKRK-UHFFFAOYSA-N 0.000 description 1
- XVSJTVAPLGSCSK-UHFFFAOYSA-N 2,3,6-trimethylbenzenethiol Chemical compound CC1=CC=C(C)C(S)=C1C XVSJTVAPLGSCSK-UHFFFAOYSA-N 0.000 description 1
- QCLJODDRBGKIRW-UHFFFAOYSA-N 2,6-dimethylbenzenethiol Chemical compound CC1=CC=CC(C)=C1S QCLJODDRBGKIRW-UHFFFAOYSA-N 0.000 description 1
- DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- JVKRKMWZYMKVTQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-N-(2-oxo-3H-1,3-benzoxazol-6-yl)acetamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)NC1=CC2=C(NC(O2)=O)C=C1 JVKRKMWZYMKVTQ-UHFFFAOYSA-N 0.000 description 1
- AHAIUNAIAHSWPG-UHFFFAOYSA-N 2-methylsulfanylpyrimidine-4,6-diamine Chemical compound CSC1=NC(N)=CC(N)=N1 AHAIUNAIAHSWPG-UHFFFAOYSA-N 0.000 description 1
- UECUPGFJVNJNQA-UHFFFAOYSA-N 2-phenylbenzenethiol Chemical compound SC1=CC=CC=C1C1=CC=CC=C1 UECUPGFJVNJNQA-UHFFFAOYSA-N 0.000 description 1
- KGBXHAVIEYXXRU-UHFFFAOYSA-N 2h-thiopyran 1-oxide Chemical compound O=S1CC=CC=C1 KGBXHAVIEYXXRU-UHFFFAOYSA-N 0.000 description 1
- CESBAYSBPMVAEI-UHFFFAOYSA-N 3,5-dimethylbenzenethiol Chemical compound CC1=CC(C)=CC(S)=C1 CESBAYSBPMVAEI-UHFFFAOYSA-N 0.000 description 1
- NDVLTZFQVDXFAN-UHFFFAOYSA-N 3-(2-cyanoethylsulfanyl)propanenitrile Chemical compound N#CCCSCCC#N NDVLTZFQVDXFAN-UHFFFAOYSA-N 0.000 description 1
- QMVAZEHZOPDGHA-UHFFFAOYSA-N 3-methoxybenzenethiol Chemical compound COC1=CC=CC(S)=C1 QMVAZEHZOPDGHA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical compound CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical group SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical group 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
- 230000001174 ascending effect Effects 0.000 description 1
- ZWOASCVFHSYHOB-UHFFFAOYSA-N benzene-1,3-dithiol Chemical group SC1=CC=CC(S)=C1 ZWOASCVFHSYHOB-UHFFFAOYSA-N 0.000 description 1
- UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical compound C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009529 body temperature measurement Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 150000004294 cyclic thioethers Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- KAGHZKBYRWUWBE-UHFFFAOYSA-N ethanethiol;ethanol Chemical compound CCO.CCS KAGHZKBYRWUWBE-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- PVBRSNZAOAJRKO-UHFFFAOYSA-N ethyl 2-sulfanylacetate Chemical compound CCOC(=O)CS PVBRSNZAOAJRKO-UHFFFAOYSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- MKIJJIMOAABWGF-UHFFFAOYSA-N methyl 2-sulfanylacetate Chemical compound COC(=O)CS MKIJJIMOAABWGF-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000008427 organic disulfides Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 229940117953 phenylisothiocyanate Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000003822 preparative gas chromatography Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 102200118166 rs16951438 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-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
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/20—Sulfiding
-
- 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
-
- 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
- C10G45/32—Selective hydrogenation of the diolefin or acetylene compounds
- C10G45/34—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used
- C10G45/36—Selective hydrogenation of the diolefin or acetylene compounds characterised by the catalyst used containing nickel or cobalt metal, or compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- General Chemical & Material Sciences (AREA)
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9009079 | 1990-07-13 | ||
| FR9009079A FR2664610A1 (fr) | 1990-07-13 | 1990-07-13 | Hydrogenation selective des essences de vapocraquage sur des catalyseurs a base d'un metal supporte dans lesquels un compose organique a ete incorpore avant chargement dans le reacteur. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04226592A JPH04226592A (ja) | 1992-08-17 |
| JP3002756B2 true JP3002756B2 (ja) | 2000-01-24 |
Family
ID=9398791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3172332A Expired - Lifetime JP3002756B2 (ja) | 1990-07-13 | 1991-07-12 | 反応器への装入前に有機化合物が組込まれている担持金属をベースとする触媒の存在下における、蒸気クラッキングガソリン中のジオレフィンの選択的水素化方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US5417844A (enExample) |
| EP (1) | EP0466567B1 (enExample) |
| JP (1) | JP3002756B2 (enExample) |
| AT (1) | ATE99354T1 (enExample) |
| DE (1) | DE69100881T2 (enExample) |
| FR (1) | FR2664610A1 (enExample) |
Families Citing this family (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2729968B1 (fr) * | 1995-01-27 | 1997-04-11 | Inst Francais Du Petrole | Procede d'hydrogenation des diolefines et eventuellement des olefines de coupes hydrocarbures riches en composes aromatiques sur des catalyseurs metalliques impregenes de composes organiques soufres |
| FR2730728B1 (fr) * | 1995-02-21 | 1997-05-23 | Inst Francais Du Petrole | Procede de separation du p-xylene comportant un pretraitement par hydrogenation selective et par de la terre activee |
| FR2743512B1 (fr) * | 1996-01-17 | 1998-03-13 | Eurecat Europ Retrait Catalys | Procede d'incorporation de soufre dans la porosite d'un catalyseur de traitement d'hydrocarbures |
| DE19608241A1 (de) * | 1996-03-04 | 1997-09-18 | Basf Ag | Verfahren zur selektiven Hydrierung von Dienen |
| CN1045099C (zh) * | 1996-09-11 | 1999-09-15 | 中国石油化工总公司 | 一种润滑油加氢补充精制工艺 |
| FR2770421B1 (fr) * | 1997-10-31 | 1999-12-10 | Inst Francais Du Petrole | Procede de preparation de catalyseurs utilisables dans les reactions de transformation de composes organiques |
| FR2770521B1 (fr) * | 1997-10-31 | 1999-12-10 | Inst Francais Du Petrole | Procede de deshydrogenation d'hydrocarbures aliphatiques satures en hydrocarbures olefiniques |
| FR2770520B1 (fr) * | 1997-10-31 | 1999-12-10 | Inst Francais Du Petrole | Procede d'hydrogenation selective des composes insatures |
| US6368496B1 (en) * | 1998-02-03 | 2002-04-09 | Exxonmobil Oil Corporation | Decreasing bi-reactive contaminants |
| FR2785833B1 (fr) * | 1998-11-18 | 2000-12-08 | Inst Francais Du Petrole | Catalyseur comprenant du nickel et son utilisation dans un procede d'hydrodesulfuration de charges hydrocarbonees |
| US6977317B1 (en) * | 2002-06-25 | 2005-12-20 | Uop Llc | Process for the selective hydrogenation of olefins |
| US6740788B1 (en) | 2002-12-19 | 2004-05-25 | Uop Llc | Integrated process for aromatics production |
| FR2854335B1 (fr) * | 2003-04-30 | 2009-03-20 | Eurecat Sa | Traitement hors site de catalyseurs d'hydrogenation |
| US7179434B1 (en) | 2004-09-08 | 2007-02-20 | Uop Llc | Integrated apparatus for aromatics production |
| US7169368B1 (en) | 2004-09-08 | 2007-01-30 | Uop Llc | Integrated apparatus for aromatics production |
| CN101300213B (zh) * | 2005-11-10 | 2011-05-11 | 环球油品公司 | 烯烃的选择性加氢方法 |
| US7517824B2 (en) * | 2005-12-06 | 2009-04-14 | Exxonmobil Chemical Company | Process for steam stripping hydrocarbons from a bromine index reduction catalyst |
| US7268263B1 (en) | 2006-05-18 | 2007-09-11 | Uop Llc | Integrated process for aromatics production |
| US7304193B1 (en) | 2006-05-18 | 2007-12-04 | Uop Llc | Integrated process for aromatics production |
| US7288687B1 (en) | 2006-05-18 | 2007-10-30 | Uop Llc | Integrated process for aromatics production |
| US7687674B2 (en) | 2006-12-28 | 2010-03-30 | Uop Llc | Low temperature process for recovering and producing para-xylene and heat exchange network therefore |
| FR2936962B1 (fr) * | 2008-10-10 | 2011-05-06 | Eurecat Sa | Procede de regeneration de catalyseurs de traitement d'hydrocarbures. |
| WO2010072836A1 (en) * | 2008-12-24 | 2010-07-01 | Shell Internationale Research Maatschappij B.V. | Process for selectively sulfiding a supported nickel catalyst |
| WO2010123694A2 (en) * | 2009-04-22 | 2010-10-28 | Exxonmobil Chemical Patents Inc. | Start up procedure in a process for purifying aromatic streams |
| US8329971B2 (en) * | 2009-04-22 | 2012-12-11 | Exxonmobil Chemical Patents Inc. | Regeneration of catalyst used in purification of aromatic streams |
| FR2949077B1 (fr) | 2009-08-17 | 2011-07-22 | Inst Francais Du Petrole | Procede de preparation d'un catalyseur supporte a base de ni et d'un metal du groupe ib pour l'hydrogenation selective d'hydrocarbures polyinsatures |
| FR2949078B1 (fr) | 2009-08-17 | 2011-07-22 | Inst Francais Du Petrole | Procede de preparation d'un catalyseur supporte ni/sn pour l'hydrogenation selective d'hydrocarbures polyinsatures |
| FR2963344B1 (fr) | 2010-07-29 | 2012-07-27 | IFP Energies Nouvelles | Procede d'hydrogenation selective en presence d'un catalyseur a base d'un metal du groupe viii prepare au moyen d'au moins un oligosaccharide cyclique |
| CN102618328B (zh) * | 2011-01-31 | 2015-02-11 | 北京安耐吉能源工程技术有限公司 | 一种汽油加工方法 |
| FR2984761B1 (fr) | 2011-12-21 | 2014-12-26 | IFP Energies Nouvelles | Procede de preparation d'un catalyseur a base d'un metal du groupe viii prepare au moyen d'au moins un additif organique et procede d'hydrogenation selective mettant en oeuvre ledit catalyseur |
| FR2990882B1 (fr) | 2012-05-24 | 2015-05-15 | IFP Energies Nouvelles | Procede de preparation d'un catalyseur a base d'un metal du groupe viii et contenant du silicium et procede d'hydrogenation selective mettant en oeuvre ledit catalyseur |
| FR3022160B1 (fr) | 2014-06-13 | 2021-05-07 | Ifp Energies Now | Catalyseur a phase active de nickel comalaxee mesoporeux et macroporeux ayant un diametre median macroporeux compris entre 50 et 300 nm et son utilisation en hydrogenation |
| FR3025728B1 (fr) | 2014-09-11 | 2018-04-20 | IFP Energies Nouvelles | Catalyseur mesoporeux a base de nickel et son utilisation en hydrogenation. |
| EA034710B1 (ru) | 2015-01-29 | 2020-03-10 | Ламмус Текнолоджи Инк. | Производство олефинов c5 из потока углеводородов c5 установки парового крекинга |
| US10010878B2 (en) | 2015-03-03 | 2018-07-03 | Uop Llc | High meso-surface area, low Si/Al ratio pentasil zeolite |
| US9890094B2 (en) | 2015-03-03 | 2018-02-13 | Uop Llc | High meso-surface area and high acid site density pentasil zeolite for use in xylene conversion |
| US10336665B2 (en) | 2015-03-03 | 2019-07-02 | Uop Llc | Yields in xylene isomerization using layer MFI zeolites |
| US9643897B2 (en) | 2015-03-03 | 2017-05-09 | Uop Llc | Enhanced propylene production in OTO process with modified zeolites |
| US9688587B2 (en) | 2015-03-03 | 2017-06-27 | Uop Llc | Process for oxygenate to olefin conversion using 2-D pentasil zeolite |
| FR3061196A1 (fr) * | 2016-12-22 | 2018-06-29 | IFP Energies Nouvelles | Procede d'hydrogenation selective mettant en œuvre un catalyseur a base de nickel prepare au moyen d'un additif comprenant une fonction alcool |
| FR3061195B1 (fr) * | 2016-12-22 | 2019-06-28 | IFP Energies Nouvelles | Procede d'hydrogenation selective mettant en œuvre un catalyseur de nickel prepare au moyen d'un additif comprenant une fonction amine, amide, ou un acide amine |
| FR3061194B1 (fr) | 2016-12-22 | 2019-06-28 | IFP Energies Nouvelles | Procede d'hydrogenation selective mettant en œuvre un catalyseur a base de nickel prepare au moyen d'un additif comprenant une fonction acide carboxylique |
| FR3061197A1 (fr) | 2016-12-22 | 2018-06-29 | IFP Energies Nouvelles | Procede d'hydrogenation selective mettant en œuvre un catalyseur a base de nickel prepare au moyen d'un additif comprenant une fonction ester |
| DE102017130369A1 (de) | 2016-12-22 | 2018-06-28 | IFP Energies Nouvelles | Verfahren zur selektiven hydrierung unter verwendung eines nickel-katalysators, hergestellt mittels eines additivs, umfassend eine amin- oder amid-funktion, oder eine aminosäure |
| FR3064500A1 (fr) | 2017-03-29 | 2018-10-05 | IFP Energies Nouvelles | Catalyseur en multicouches d'hyrogenation selective |
| FR3068985A1 (fr) | 2017-07-13 | 2019-01-18 | IFP Energies Nouvelles | Procede d’hydrogenation des aromatiques mettant en oeuvre un catalyseur obtenu par comalaxage comprenant un support specifique |
| FR3068982A1 (fr) | 2017-07-13 | 2019-01-18 | IFP Energies Nouvelles | Procede d'hydrogenation selective mettant en œuvre un catalyseur obtenu par comalaxage comprenant un support specifique |
| FR3068983B1 (fr) | 2017-07-13 | 2019-07-12 | IFP Energies Nouvelles | Procede d'hydrogenation selective mettant en œuvre un catalyseur obtenu par impregnation comprenant un support specifique |
| FR3068984B1 (fr) | 2017-07-13 | 2020-01-17 | IFP Energies Nouvelles | Procede d'hydrogenation des aromatiques mettant en œuvre un catalyseur obtenu par impregnation comprenant un support specifique. |
| FR3076747B1 (fr) | 2018-01-15 | 2022-06-10 | Ifp Energies Now | Procede de preparation d'un catalyseur particulier d'hydrogenation selective et d'hydrogenation des aromatiques par malaxage |
| FR3087787B1 (fr) | 2018-10-25 | 2020-12-18 | Ifp Energies Now | Procede d’hydrogenation comprenant un catalyseur prepare par addition d’un compose organique en phase gazeuse |
| US11459513B2 (en) * | 2021-01-28 | 2022-10-04 | Saudi Arabian Oil Company | Steam cracking process integrating oxidized disulfide oil additive |
| EP4424797A1 (de) * | 2023-03-02 | 2024-09-04 | OMV Downstream GmbH | Verfahren zur reinigung eines synthetischen rohölstroms |
| EP4424796A1 (de) | 2023-03-02 | 2024-09-04 | OMV Downstream GmbH | Verfahren zur reinigung eines synthetischen rohölstroms |
| FR3163283A1 (fr) | 2024-06-18 | 2025-12-19 | IFP Energies Nouvelles | Catalyseur comprenant du cuivre, du nickel et du soufre pour le traitement de reformat |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE623777A (enExample) * | 1961-10-20 | |||
| DE1190127B (de) * | 1963-06-21 | 1965-04-01 | Bayer Ag | Verfahren zur selektiven Hydrierung von Pyrolysebenzin oder dessen Fraktionen |
| OA02047A (fr) * | 1965-02-13 | 1970-05-05 | Inst Francais Du Petrole | Procédé d'hydrogenation selective des diolefines. |
| US3893944A (en) * | 1972-05-16 | 1975-07-08 | Exxon Research Engineering Co | Catalyst for hydrogenation of organic compounds |
| US3919341A (en) * | 1973-02-16 | 1975-11-11 | Universal Oil Prod Co | Olefin isomerization process |
| FR2413127A1 (fr) * | 1978-01-02 | 1979-07-27 | Inst Francais Du Petrole | Procede de preparation d'un catalyseur de metal noble du groupe viii presentant une resistance amelioree au soufre, catalyseur obtenu et son utilisation pour l'hydrogenation d'hydrocarbures aromatiques |
| FR2548205B1 (fr) * | 1983-06-30 | 1985-11-29 | Eurecat Europ Retrait Catalys | Procede de presulfuration de catalyseur de traitement d'hydrocarbures |
| DE3562987D1 (en) * | 1984-10-30 | 1988-07-07 | Eurecat Europ Retrait Catalys | Method for presulfiding a catalyst for the treatment of hydrocarbons |
| US4734540A (en) * | 1986-12-22 | 1988-03-29 | Uop Inc. | Catalyst for the selective hydrogenation of polyunsaturated organics |
| FR2627105B3 (fr) * | 1988-02-16 | 1990-06-08 | Inst Francais Du Petrole | Procede de presulfuration de catalyseur de traitement d'hydrocarbures |
-
1990
- 1990-07-13 FR FR9009079A patent/FR2664610A1/fr active Granted
-
1991
- 1991-07-08 DE DE69100881T patent/DE69100881T2/de not_active Expired - Lifetime
- 1991-07-08 EP EP91401879A patent/EP0466567B1/fr not_active Expired - Lifetime
- 1991-07-08 AT AT91401879T patent/ATE99354T1/de not_active IP Right Cessation
- 1991-07-12 JP JP3172332A patent/JP3002756B2/ja not_active Expired - Lifetime
-
1992
- 1992-11-18 US US07/978,074 patent/US5417844A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US5417844A (en) | 1995-05-23 |
| DE69100881D1 (de) | 1994-02-10 |
| ATE99354T1 (de) | 1994-01-15 |
| EP0466567A1 (fr) | 1992-01-15 |
| FR2664610A1 (fr) | 1992-01-17 |
| EP0466567B1 (fr) | 1993-12-29 |
| JPH04226592A (ja) | 1992-08-17 |
| DE69100881T2 (de) | 1994-07-28 |
| FR2664610B1 (enExample) | 1994-07-13 |
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