DE2449298A1 - Verfahren zur durchfuehrung einer isomerisierung - Google Patents
Verfahren zur durchfuehrung einer isomerisierungInfo
- Publication number
- DE2449298A1 DE2449298A1 DE19742449298 DE2449298A DE2449298A1 DE 2449298 A1 DE2449298 A1 DE 2449298A1 DE 19742449298 DE19742449298 DE 19742449298 DE 2449298 A DE2449298 A DE 2449298A DE 2449298 A1 DE2449298 A1 DE 2449298A1
- Authority
- DE
- Germany
- Prior art keywords
- butene
- olefin
- isomerization
- olefins
- carried out
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 27
- 238000006317 isomerization reaction Methods 0.000 title claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 239000003054 catalyst Substances 0.000 claims description 23
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims description 14
- WWUVJRULCWHUSA-UHFFFAOYSA-N 2-methyl-1-pentene Chemical compound CCCC(C)=C WWUVJRULCWHUSA-UHFFFAOYSA-N 0.000 claims description 14
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 14
- 239000003456 ion exchange resin Substances 0.000 claims description 9
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 9
- 239000007791 liquid phase Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 150000001336 alkenes Chemical class 0.000 claims description 8
- OWWIWYDDISJUMY-UHFFFAOYSA-N 2,3-dimethylbut-1-ene Chemical compound CC(C)C(C)=C OWWIWYDDISJUMY-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 2
- MHNNAWXXUZQSNM-UHFFFAOYSA-N 2-methylbut-1-ene Chemical compound CCC(C)=C MHNNAWXXUZQSNM-UHFFFAOYSA-N 0.000 claims description 2
- RYKZRKKEYSRDNF-UHFFFAOYSA-N 3-methylidenepentane Chemical compound CCC(=C)CC RYKZRKKEYSRDNF-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 238000006277 sulfonation reaction Methods 0.000 claims 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 18
- 229920000642 polymer Polymers 0.000 description 16
- WGLLSSPDPJPLOR-UHFFFAOYSA-N 2,3-dimethylbut-2-ene Chemical compound CC(C)=C(C)C WGLLSSPDPJPLOR-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BEQGRRJLJLVQAQ-UHFFFAOYSA-N 3-methylpent-2-ene Chemical compound CCC(C)=CC BEQGRRJLJLVQAQ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- BKOOMYPCSUNDGP-UHFFFAOYSA-N 2-methylbut-2-ene Chemical compound CC=C(C)C BKOOMYPCSUNDGP-UHFFFAOYSA-N 0.000 description 2
- FRDAATYAJDYRNW-UHFFFAOYSA-N 3-methyl-3-pentanol Chemical compound CCC(C)(O)CC FRDAATYAJDYRNW-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- -1 hydrogen ions Chemical class 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- CHRJZRDFSQHIFI-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;styrene Chemical class C=CC1=CC=CC=C1.C=CC1=CC=CC=C1C=C CHRJZRDFSQHIFI-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 238000003421 catalytic decomposition reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 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
- C07C5/23—Rearrangement of carbon-to-carbon unsaturated bonds
- C07C5/25—Migration of carbon-to-carbon double bonds
- C07C5/2506—Catalytic processes
- C07C5/2562—Catalytic processes with hydrides or organic compounds
- C07C5/2568—Catalytic processes with hydrides or organic compounds with ion-exchange resins
-
- 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
- C07C5/2266—Catalytic processes not covered by C07C5/23 - C07C5/31 with hydrides or organic compounds
- C07C5/2273—Catalytic processes not covered by C07C5/23 - C07C5/31 with hydrides or organic compounds with ion-exchange resins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- C07C2531/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- C07C2531/08—Ion-exchange resins
- C07C2531/10—Ion-exchange resins sulfonated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|---|---|
| US41525973A | 1973-11-12 | 1973-11-12 | |
| US415258A US3920765A (en) | 1973-11-12 | 1973-11-12 | Inhibition of polymerization during the isomerization of olefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2449298A1 true DE2449298A1 (de) | 1975-05-15 |
Family
ID=27022925
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742449298 Pending DE2449298A1 (de) | 1973-11-12 | 1974-10-16 | Verfahren zur durchfuehrung einer isomerisierung |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5077305A (enrdf_load_stackoverflow) |
| BR (1) | BR7409333A (enrdf_load_stackoverflow) |
| DE (1) | DE2449298A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2250729B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1475191A (enrdf_load_stackoverflow) |
| IT (1) | IT1023205B (enrdf_load_stackoverflow) |
| NL (1) | NL7414620A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042537A1 (de) * | 1980-06-19 | 1981-12-30 | Ec Erdölchemie Gmbh | Verfahren zur Stellungsisomerisierung von endständigen Doppelbindungen in Olefinen |
| US5910618A (en) * | 1993-03-04 | 1999-06-08 | Sumitomo Chemical Company, Limited | Process for preparing 2,3-dimethyl-2-butene |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8709648D0 (en) * | 1987-04-23 | 1987-05-28 | Bp Chem Int Ltd | Chemical process |
| EP0334941B1 (en) * | 1987-10-01 | 1995-04-26 | Exxon Chemical Patents Inc. | Increasing the level of 2-methyl-2-butene in isoamylene |
| JPH03232822A (ja) * | 1990-02-05 | 1991-10-16 | Sumitomo Chem Co Ltd | ２，５―ジメチル―２，４―ヘキサジエンの製造方法 |
| DK0648721T3 (da) * | 1993-10-15 | 1999-04-19 | Fina Research | Fremgangsmåde til rensning af middellange alkener |
| JP4505947B2 (ja) * | 1999-05-28 | 2010-07-21 | 住友化学株式会社 | ２，３−ジメチルブテン−１と２，３−ジメチルブテン−２の併産方法 |
-
1974
- 1974-10-11 GB GB4417774A patent/GB1475191A/en not_active Expired
- 1974-10-16 DE DE19742449298 patent/DE2449298A1/de active Pending
- 1974-11-07 FR FR7436914A patent/FR2250729B1/fr not_active Expired
- 1974-11-07 BR BR933374A patent/BR7409333A/pt unknown
- 1974-11-08 NL NL7414620A patent/NL7414620A/xx unknown
- 1974-11-11 IT IT5397074A patent/IT1023205B/it active
- 1974-11-12 JP JP13041974A patent/JPS5077305A/ja active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0042537A1 (de) * | 1980-06-19 | 1981-12-30 | Ec Erdölchemie Gmbh | Verfahren zur Stellungsisomerisierung von endständigen Doppelbindungen in Olefinen |
| US5910618A (en) * | 1993-03-04 | 1999-06-08 | Sumitomo Chemical Company, Limited | Process for preparing 2,3-dimethyl-2-butene |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2250729B1 (enrdf_load_stackoverflow) | 1978-07-07 |
| JPS5077305A (enrdf_load_stackoverflow) | 1975-06-24 |
| GB1475191A (en) | 1977-06-01 |
| BR7409333A (pt) | 1976-05-18 |
| NL7414620A (nl) | 1975-05-14 |
| FR2250729A1 (enrdf_load_stackoverflow) | 1975-06-06 |
| IT1023205B (it) | 1978-05-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |