DE2728218C2 - Verfahren zur Isomerisierung von 1-Buten in 2-Buten - Google Patents
Verfahren zur Isomerisierung von 1-Buten in 2-ButenInfo
- Publication number
- DE2728218C2 DE2728218C2 DE19772728218 DE2728218A DE2728218C2 DE 2728218 C2 DE2728218 C2 DE 2728218C2 DE 19772728218 DE19772728218 DE 19772728218 DE 2728218 A DE2728218 A DE 2728218A DE 2728218 C2 DE2728218 C2 DE 2728218C2
- Authority
- DE
- Germany
- Prior art keywords
- butene
- catalyst
- hydrogen
- temperature
- isomerization
- 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
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 title claims description 47
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 title claims description 31
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 title claims description 16
- 238000006317 isomerization reaction Methods 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 14
- 239000003054 catalyst Substances 0.000 claims description 45
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 22
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- 229930195733 hydrocarbon Natural products 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000005984 hydrogenation reaction Methods 0.000 description 6
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 229910000510 noble metal Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000009849 deactivation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000001282 iso-butane Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- -1 sulphur compound 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
- 238000004448 titration Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/22—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by isomerisation
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/226—Catalytic processes not covered by C07C5/23 - C07C5/31 with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2521/00—Catalysts comprising the elements, oxides or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium or hafnium
- C07C2521/02—Boron or aluminium; Oxides or hydroxides thereof
- C07C2521/04—Alumina
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals
- C07C2523/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of noble metals of the platinum group metals
- C07C2523/44—Palladium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7619661A FR2355792A1 (fr) | 1976-06-25 | 1976-06-25 | Procede d'isomerisation du 1-butene en 2-butene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2728218A1 DE2728218A1 (de) | 1978-01-05 |
| DE2728218C2 true DE2728218C2 (de) | 1987-03-05 |
Family
ID=9174949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772728218 Expired DE2728218C2 (de) | 1976-06-25 | 1977-06-23 | Verfahren zur Isomerisierung von 1-Buten in 2-Buten |
Country Status (8)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2436176A1 (fr) * | 1978-09-14 | 1980-04-11 | Inst Francais Du Petrole | Procede de production d'essence a haut indice d'octane et en particulier d'essence utilisable sans plomb |
| JPS55126350A (en) * | 1979-03-23 | 1980-09-30 | Nippon Mining Co Ltd | Copper wire |
| DE10152842A1 (de) | 2001-10-25 | 2003-05-08 | Oxeno Olefinchemie Gmbh | Hydroisomerisierung von Olefinen mit 4-6 Kohlenstoffatomen |
| JP5784037B2 (ja) * | 2009-12-22 | 2015-09-24 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 直鎖アルファ−オレフィンの異性化 |
| EP2702017A4 (en) * | 2011-04-28 | 2015-02-25 | Basf Se | ISOMERIZATION LIGHT ALPHA OLEFINE TO LIGHT INTERNAL OLEFINS |
| US20150141605A1 (en) * | 2012-05-03 | 2015-05-21 | David Bradin | Production of polypropylene from renewable resources |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5229999B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-03-01 | 1977-08-05 |
-
1976
- 1976-06-25 FR FR7619661A patent/FR2355792A1/fr active Granted
-
1977
- 1977-06-20 BE BE1008204A patent/BE855857A/xx not_active IP Right Cessation
- 1977-06-22 NL NL7706924A patent/NL7706924A/xx not_active Application Discontinuation
- 1977-06-22 IT IT2493077A patent/IT1082109B/it active
- 1977-06-23 DE DE19772728218 patent/DE2728218C2/de not_active Expired
- 1977-06-23 ES ES460084A patent/ES460084A1/es not_active Expired
- 1977-06-24 JP JP52076032A patent/JPS6054934B2/ja not_active Expired
- 1977-06-24 GB GB2663877A patent/GB1535158A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1082109B (it) | 1985-05-21 |
| NL7706924A (nl) | 1977-12-28 |
| DE2728218A1 (de) | 1978-01-05 |
| JPS6054934B2 (ja) | 1985-12-03 |
| JPS532406A (en) | 1978-01-11 |
| BE855857A (fr) | 1977-12-20 |
| ES460084A1 (es) | 1978-05-01 |
| FR2355792A1 (fr) | 1978-01-20 |
| FR2355792B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1980-02-15 |
| GB1535158A (en) | 1978-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |