JPH0148318B2 - - Google Patents
Info
- Publication number
- JPH0148318B2 JPH0148318B2 JP56062709A JP6270981A JPH0148318B2 JP H0148318 B2 JPH0148318 B2 JP H0148318B2 JP 56062709 A JP56062709 A JP 56062709A JP 6270981 A JP6270981 A JP 6270981A JP H0148318 B2 JPH0148318 B2 JP H0148318B2
- Authority
- JP
- Japan
- Prior art keywords
- fraction
- acetylenes
- sulfur
- dienes
- hydrocarbons
- 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
Links
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 46
- 229930195733 hydrocarbon Natural products 0.000 claims description 31
- 150000002430 hydrocarbons Chemical class 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 24
- 229910052763 palladium Inorganic materials 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 239000003054 catalyst Substances 0.000 claims description 20
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 150000001993 dienes Chemical class 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 238000004230 steam cracking Methods 0.000 claims description 7
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 15
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 238000005406 washing Methods 0.000 description 13
- -1 ethylene, propylene, butadiene Chemical class 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000098 polyolefin Polymers 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- MWWATHDPGQKSAR-UHFFFAOYSA-N propyne Chemical group CC#C MWWATHDPGQKSAR-UHFFFAOYSA-N 0.000 description 2
- 150000003464 sulfur compounds Chemical class 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 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
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical compound CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 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
- 230000003197 catalytic effect Effects 0.000 description 1
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Landscapes
- Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6270981A JPS57177090A (en) | 1981-04-24 | 1981-04-24 | Hydrogenation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6270981A JPS57177090A (en) | 1981-04-24 | 1981-04-24 | Hydrogenation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57177090A JPS57177090A (en) | 1982-10-30 |
| JPH0148318B2 true JPH0148318B2 (xx) | 1989-10-18 |
Family
ID=13208112
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6270981A Granted JPS57177090A (en) | 1981-04-24 | 1981-04-24 | Hydrogenation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57177090A (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0696709B2 (ja) * | 1987-10-23 | 1994-11-30 | 日本石油株式会社 | 炭化水素類の選択的水素化方法 |
| DE102009027406A1 (de) * | 2009-07-01 | 2011-01-05 | Evonik Oxeno Gmbh | Verfahren zur Herstellung von geruchsarmen n-Butan |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4878204A (xx) * | 1972-01-20 | 1973-10-20 | ||
| JPS4911901A (xx) * | 1972-05-15 | 1974-02-01 | ||
| JPS506004A (xx) * | 1973-05-22 | 1975-01-22 | ||
| JPS5021483A (xx) * | 1973-06-30 | 1975-03-07 | ||
| JPS5030643A (xx) * | 1973-04-02 | 1975-03-26 | ||
| JPS5523165A (en) * | 1978-08-09 | 1980-02-19 | Nippon Oil Co Ltd | Hydrogenation purification of cracked gasoline |
| JPS5560591A (en) * | 1978-10-31 | 1980-05-07 | Nippon Steel Chem Co Ltd | Hydrogenation purification of gas-oil |
-
1981
- 1981-04-24 JP JP6270981A patent/JPS57177090A/ja active Granted
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4878204A (xx) * | 1972-01-20 | 1973-10-20 | ||
| JPS4911901A (xx) * | 1972-05-15 | 1974-02-01 | ||
| JPS5030643A (xx) * | 1973-04-02 | 1975-03-26 | ||
| JPS506004A (xx) * | 1973-05-22 | 1975-01-22 | ||
| JPS5021483A (xx) * | 1973-06-30 | 1975-03-07 | ||
| JPS5523165A (en) * | 1978-08-09 | 1980-02-19 | Nippon Oil Co Ltd | Hydrogenation purification of cracked gasoline |
| JPS5560591A (en) * | 1978-10-31 | 1980-05-07 | Nippon Steel Chem Co Ltd | Hydrogenation purification of gas-oil |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57177090A (en) | 1982-10-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4132745A (en) | Process for isomerizing 1-butene to 2-butene | |
| Molnár et al. | Hydrogenation of carbon–carbon multiple bonds: chemo-, regio-and stereo-selectivity | |
| EP0733030B1 (en) | Selective hydrogenation of highly unsaturated compounds in hydrocarbon streams | |
| JP3199848B2 (ja) | ブタジエンの選択的水素化法 | |
| JP4606521B2 (ja) | 炭化水素流れ中のアセチレンと１，２―ブタジエンを同時的に選択的水素化する方法 | |
| US7045670B2 (en) | Process for liquid phase hydrogenation | |
| US4277313A (en) | Recovery of 1,3-butadiene | |
| US3485887A (en) | Process for the treatment by hydrogenation of c4-hydrocarbons containing butadiene and n-but-1-ene | |
| KR19980033193A (ko) | 4개의 탄소 원자를 포함하는 탄화수소 분급물로부터 이소부텐및 프로필렌을 제조하는 신규한 방법 | |
| JP5774100B2 (ja) | 多重不飽和炭化水素をオレフィン含有炭化水素混合物において選択的に水素化するための方法 | |
| TWI841660B (zh) | 在硫醇類、二硫化物類及c5烴類存在下從c4烴類流中除去多不飽和烴類的方法 | |
| US3662015A (en) | Method of preventing double bond migration of mono-olefinic hydrocarbons in selective hydrogenation | |
| US4230897A (en) | Process for selectively hydrogenating a hydrocarbon cut containing at least one diolefinic hydrocarbon and at least one acetylenic hydrocarbon using a palladium catalyst with crystallites of at least 50 angstroms | |
| JPS633851B2 (xx) | ||
| US4247725A (en) | Method of removing acetylenes from C4 -hydrocarbon mixture containing butadiene | |
| TWI835968B (zh) | 由烴類流中移除硫醇類的催化劑及方法 | |
| CA1083612A (en) | Method of reducing the alpha-acetylene content of hydrocarbon | |
| JP2593334B2 (ja) | ブタジエンおよび硫黄化合物を含むｃ４炭化水素留分における１−ブテンの２−ブテンへの異性化方法 | |
| US4174355A (en) | Process for removing α-acetylenes from diolefins | |
| JPH0148318B2 (xx) | ||
| JPS639496B2 (xx) | ||
| JPH0148317B2 (xx) | ||
| JPS6325566B2 (xx) | ||
| KR20050029201A (ko) | 탄화수소 크래킹에 의해 수득되는 크래킹된 가스로부터에틸렌 및 프로필렌 함유 스트림의 회수 방법 | |
| CA1142506A (en) | Hydrogenation catalyst |