DE2604261C2 - Verfahren zur Herstellung von 2,6,10-Trimethylundeca-1,9-dien- und/oder 2,6-Dimethylhepta-1,5-dien - Google Patents
Verfahren zur Herstellung von 2,6,10-Trimethylundeca-1,9-dien- und/oder 2,6-Dimethylhepta-1,5-dienInfo
- Publication number
- DE2604261C2 DE2604261C2 DE19762604261 DE2604261A DE2604261C2 DE 2604261 C2 DE2604261 C2 DE 2604261C2 DE 19762604261 DE19762604261 DE 19762604261 DE 2604261 A DE2604261 A DE 2604261A DE 2604261 C2 DE2604261 C2 DE 2604261C2
- Authority
- DE
- Germany
- Prior art keywords
- diene
- dimethylcycloocta
- trimethylundeca
- dimethylhepta
- disproportionation
- 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
- 238000000034 method Methods 0.000 title claims description 7
- DONSTYDPUORSDN-UHFFFAOYSA-N 2,6-dimethylhepta-1,5-diene Chemical compound CC(C)=CCCC(C)=C DONSTYDPUORSDN-UHFFFAOYSA-N 0.000 title description 8
- 238000002360 preparation method Methods 0.000 title description 3
- ITMDNOFFRHDSDX-UHFFFAOYSA-N 2,6,10-trimethylundeca-1,9-diene Chemical compound CC(=C)CCCC(C)CCC=C(C)C ITMDNOFFRHDSDX-UHFFFAOYSA-N 0.000 title description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 26
- IAQRGUVFOMOMEM-UHFFFAOYSA-N but-2-ene Chemical compound CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 16
- 238000007323 disproportionation reaction Methods 0.000 claims description 15
- -1 cyclic olefin Chemical class 0.000 claims description 10
- XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GMXUKNKDUOKQJY-UHFFFAOYSA-N 1,5,9-trimethylcyclododecene Chemical compound CC1=CCCC(CCCC(CCC1)C)C GMXUKNKDUOKQJY-UHFFFAOYSA-N 0.000 claims description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 21
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- LCRQIJVZGYGHHQ-UHFFFAOYSA-N 1,5-dimethylcyclooctene Chemical compound CC1CCCC(C)=CCC1 LCRQIJVZGYGHHQ-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000009102 absorption Effects 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- WHWDWIHXSPCOKZ-UHFFFAOYSA-N hexahydrofarnesyl acetone Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)=O WHWDWIHXSPCOKZ-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000013638 trimer Substances 0.000 description 2
- AEWDJRWDUMQPQG-UHFFFAOYSA-N 1,4-dimethylcyclooctene Chemical compound CC1CCCCC(C)=CC1 AEWDJRWDUMQPQG-UHFFFAOYSA-N 0.000 description 1
- YZYBDLICKMTFAV-UHFFFAOYSA-N 1,6,10-trimethylcyclododecene Chemical compound CC1=CCCCC(CCCC(CC1)C)C YZYBDLICKMTFAV-UHFFFAOYSA-N 0.000 description 1
- MXCNYKNYSNAEPA-UHFFFAOYSA-N 2,6,10-trimethylundeca-1,5,9-triene Chemical compound CC(C)=CCCC(C)=CCCC(C)=C MXCNYKNYSNAEPA-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- SLQMKNPIYMOEGB-UHFFFAOYSA-N 2-methylhexa-1,5-diene Chemical compound CC(=C)CCC=C SLQMKNPIYMOEGB-UHFFFAOYSA-N 0.000 description 1
- HVYVHTUFWOEQPD-UHFFFAOYSA-N 3,7-dimethyldodeca-2,10-diene Chemical compound CC=CCCC(C)CCCC(C)=CC HVYVHTUFWOEQPD-UHFFFAOYSA-N 0.000 description 1
- DUKHJOXPRLZAMR-UHFFFAOYSA-N 3,7-dimethyldodeca-2,6,10-triene Chemical compound CC=CCCC(C)=CCCC(C)=CC DUKHJOXPRLZAMR-UHFFFAOYSA-N 0.000 description 1
- IHTXRFISZHYPCI-UHFFFAOYSA-N 3-methylocta-2,6-diene Chemical compound CC=CCCC(C)=CC IHTXRFISZHYPCI-UHFFFAOYSA-N 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Diphosphoinositol tetrakisphosphate Chemical compound OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001339 alkali metal compounds 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
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000005675 cyclic monoalkenes Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- HYERJXDYFLQTGF-UHFFFAOYSA-N rhenium Chemical compound [Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re][Re] HYERJXDYFLQTGF-UHFFFAOYSA-N 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/02—Metathesis reactions at an unsaturated carbon-to-carbon bond
- C07C6/04—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond
- C07C6/06—Metathesis reactions at an unsaturated carbon-to-carbon bond at a carbon-to-carbon double bond at a cyclic carbon-to-carbon double bond
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB509175A GB1532981A (en) | 1975-02-06 | 1975-02-06 | Process for preparing olefinic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2604261A1 DE2604261A1 (de) | 1976-08-19 |
| DE2604261C2 true DE2604261C2 (de) | 1986-10-02 |
Family
ID=9789598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762604261 Expired DE2604261C2 (de) | 1975-02-06 | 1976-02-04 | Verfahren zur Herstellung von 2,6,10-Trimethylundeca-1,9-dien- und/oder 2,6-Dimethylhepta-1,5-dien |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS6058729B2 (it) |
| BE (1) | BE838154A (it) |
| CH (1) | CH626315A5 (it) |
| DE (1) | DE2604261C2 (it) |
| FR (1) | FR2300056A1 (it) |
| GB (1) | GB1532981A (it) |
| IT (1) | IT1054836B (it) |
| NL (1) | NL7601107A (it) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1552368A (en) * | 1976-12-09 | 1979-09-12 | Shell Int Research | Preparation of olefinic compounds by disproportionation |
| US4412089A (en) * | 1981-08-24 | 1983-10-25 | Shell Oil Company | Process for the preparation of dienes and/or trienes |
| JPS6082028U (ja) * | 1983-11-11 | 1985-06-06 | 東洋化学株式会社 | 軒樋の取付構造 |
| JPS6288017U (it) * | 1985-11-25 | 1987-06-05 | ||
| FR2652349B1 (fr) * | 1989-09-27 | 1993-02-19 | Elf Aquitaine | Procede de preparation de composes hydroxyles ou carbonyles, a deux ou trois doubles liaisons et plus de 5 atomes de carbone. |
-
1975
- 1975-02-06 GB GB509175A patent/GB1532981A/en not_active Expired
-
1976
- 1976-02-02 BE BE1007177A patent/BE838154A/xx not_active IP Right Cessation
- 1976-02-04 JP JP1045576A patent/JPS6058729B2/ja not_active Expired
- 1976-02-04 DE DE19762604261 patent/DE2604261C2/de not_active Expired
- 1976-02-04 CH CH137876A patent/CH626315A5/de not_active IP Right Cessation
- 1976-02-04 IT IT1989576A patent/IT1054836B/it active
- 1976-02-04 FR FR7603063A patent/FR2300056A1/fr active Granted
- 1976-02-04 NL NL7601107A patent/NL7601107A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7601107A (nl) | 1976-08-10 |
| DE2604261A1 (de) | 1976-08-19 |
| CH626315A5 (en) | 1981-11-13 |
| FR2300056A1 (fr) | 1976-09-03 |
| GB1532981A (en) | 1978-11-22 |
| JPS6058729B2 (ja) | 1985-12-21 |
| FR2300056B1 (it) | 1978-11-10 |
| IT1054836B (it) | 1981-11-30 |
| JPS51101902A (ja) | 1976-09-08 |
| BE838154A (nl) | 1976-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8128 | New person/name/address of the agent |
Representative=s name: JUNG, E., DIPL.-CHEM. DR.PHIL. SCHIRDEWAHN, J., DI |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |