DE1230023B - Verfahren zur Herstellung von cis, cis-Cyclodecadien-(1, 6) - Google Patents
Verfahren zur Herstellung von cis, cis-Cyclodecadien-(1, 6)Info
- Publication number
- DE1230023B DE1230023B DEST20502A DEST020502A DE1230023B DE 1230023 B DE1230023 B DE 1230023B DE ST20502 A DEST20502 A DE ST20502A DE ST020502 A DEST020502 A DE ST020502A DE 1230023 B DE1230023 B DE 1230023B
- Authority
- DE
- Germany
- Prior art keywords
- cis
- cyclodecadiene
- trans
- metals
- preparation
- 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 11
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 6
- 150000002739 metals Chemical class 0.000 claims description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 3
- 230000000737 periodic effect Effects 0.000 claims description 3
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- MZJCFRKLOXHQIL-UHFFFAOYSA-N (1Z,3E)-cyclodeca-1,3-diene Chemical compound C/1=CC=C/CCCCCC1 MZJCFRKLOXHQIL-UHFFFAOYSA-N 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- MZJCFRKLOXHQIL-WZNPJAPVSA-N (3e)-cyclodeca-1,3-diene Chemical compound C1CCC\C=C\C=CCC1 MZJCFRKLOXHQIL-WZNPJAPVSA-N 0.000 description 11
- 229930195733 hydrocarbon Natural products 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000004215 Carbon black (E152) Substances 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- MZJCFRKLOXHQIL-CCAGOZQPSA-N (1Z,3Z)-cyclodeca-1,3-diene Chemical compound C1CCC\C=C/C=C\CC1 MZJCFRKLOXHQIL-CCAGOZQPSA-N 0.000 description 4
- ZWUBFMWIQJSEQS-UHFFFAOYSA-N 1,1-bis(ethenyl)cyclohexane Chemical compound C=CC1(C=C)CCCCC1 ZWUBFMWIQJSEQS-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- GCPCLEKQVMKXJM-UHFFFAOYSA-N ethoxy(diethyl)alumane Chemical compound CCO[Al](CC)CC GCPCLEKQVMKXJM-UHFFFAOYSA-N 0.000 description 3
- 238000006317 isomerization reaction Methods 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 238000003756 stirring 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
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008707 rearrangement Effects 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- ARKHCBWJALMQJO-UHFFFAOYSA-N 1,2-bis(ethenyl)cyclohexane Chemical compound C=CC1CCCCC1C=C ARKHCBWJALMQJO-UHFFFAOYSA-N 0.000 description 1
- 238000005952 Cope rearrangement reaction Methods 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- JUPWRUDTZGBNEX-UHFFFAOYSA-N cobalt;pentane-2,4-dione Chemical compound [Co].CC(=O)CC(C)=O.CC(=O)CC(C)=O.CC(=O)CC(C)=O JUPWRUDTZGBNEX-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 125000002534 ethynyl group Chemical class [H]C#C* 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- -1 transition metal acetylacetonate Chemical class 0.000 description 1
- 150000003623 transition metal compounds Chemical class 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/40—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals
- C07C15/42—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic
- C07C15/44—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts substituted by unsaturated carbon radicals monocyclic the hydrocarbon substituent containing a carbon-to-carbon double bond
-
- 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
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C11/00—Aliphatic unsaturated hydrocarbons
- C07C11/21—Alkatrienes; Alkatetraenes; Other alkapolyenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/271—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a nine- to ten- membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
-
- 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
- C07C5/2556—Catalytic processes with metals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
- C07C2601/20—Systems containing only non-condensed rings with a ring being at least seven-membered the ring being twelve-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE646244D BE646244A (enExample) | 1963-04-10 | ||
| DENDAT1288087D DE1288087B (de) | 1963-04-10 | Verfahren zur Mischoligomerisation unter Verwendung von 1,3-Diolefinen in Gegenwart eines kohlenoxydfreien Organo-Metallkoinplexkatalysators der Übergangsmetalle der VIII. Nebengruppe | |
| FR929149A FR1351938A (fr) | 1963-03-25 | 1963-03-25 | Procédé pour la co-oligomérisation de dioléfines |
| DEST20502A DE1230023B (de) | 1963-04-10 | 1963-04-10 | Verfahren zur Herstellung von cis, cis-Cyclodecadien-(1, 6) |
| FR969884A FR1386991A (fr) | 1963-04-10 | 1964-04-06 | Procédé de préparation de cis, cis-cyclodécadiène-(1, 6) à partir de trans, cis-ciclo-décadiène-(1, 5) |
| CH445164A CH446312A (de) | 1963-04-10 | 1964-04-08 | Verfahren zur Herstellung von cis,cis-Cyclodecadien-(1,6) |
| NL646403826A NL139294B (nl) | 1963-04-10 | 1964-04-09 | Werkwijze voor het stabiliseren van trans,cis-cyclo-decadieen-1,5. |
| US358457A US3317620A (en) | 1963-04-10 | 1964-04-09 | Cis, cis-cyclodecadiene-(1, 6) and its manufacture |
| GB14467/62A GB1022875A (en) | 1963-04-10 | 1964-04-10 | Cis, cis-cyclodecadiene-(1.6) and its manufacture |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEST20502A DE1230023B (de) | 1963-04-10 | 1963-04-10 | Verfahren zur Herstellung von cis, cis-Cyclodecadien-(1, 6) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1230023B true DE1230023B (de) | 1966-12-08 |
Family
ID=7458598
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1288087D Pending DE1288087B (de) | 1963-04-10 | Verfahren zur Mischoligomerisation unter Verwendung von 1,3-Diolefinen in Gegenwart eines kohlenoxydfreien Organo-Metallkoinplexkatalysators der Übergangsmetalle der VIII. Nebengruppe | |
| DEST20502A Pending DE1230023B (de) | 1963-03-25 | 1963-04-10 | Verfahren zur Herstellung von cis, cis-Cyclodecadien-(1, 6) |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1288087D Pending DE1288087B (de) | 1963-04-10 | Verfahren zur Mischoligomerisation unter Verwendung von 1,3-Diolefinen in Gegenwart eines kohlenoxydfreien Organo-Metallkoinplexkatalysators der Übergangsmetalle der VIII. Nebengruppe |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3317620A (enExample) |
| BE (1) | BE646244A (enExample) |
| CH (1) | CH446312A (enExample) |
| DE (2) | DE1230023B (enExample) |
| GB (1) | GB1022875A (enExample) |
| NL (1) | NL139294B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010086314A1 (de) | 2009-01-28 | 2010-08-05 | Basf Se | Verfahren zur herstellung von reinem cyclododecanon |
| WO2010086313A1 (de) | 2009-01-28 | 2010-08-05 | Basf Se | Verfahren zur isolierung von dodecatrienal und seine verwendung als aromastoff |
| DE102014212602A1 (de) | 2013-07-02 | 2015-01-08 | Basf Se | Verfahren zur Herstellung eines Ketons aus einem Olefin |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3407238A (en) * | 1965-09-13 | 1968-10-22 | Montedison Spa | Process for the preparation of cyclododecadienes |
| US5076460A (en) * | 1991-02-13 | 1991-12-31 | Hussell Donald E | Three ball snap hinge box |
-
0
- BE BE646244D patent/BE646244A/xx unknown
- DE DENDAT1288087D patent/DE1288087B/de active Pending
-
1963
- 1963-04-10 DE DEST20502A patent/DE1230023B/de active Pending
-
1964
- 1964-04-08 CH CH445164A patent/CH446312A/de unknown
- 1964-04-09 NL NL646403826A patent/NL139294B/xx unknown
- 1964-04-09 US US358457A patent/US3317620A/en not_active Expired - Lifetime
- 1964-04-10 GB GB14467/62A patent/GB1022875A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010086314A1 (de) | 2009-01-28 | 2010-08-05 | Basf Se | Verfahren zur herstellung von reinem cyclododecanon |
| WO2010086313A1 (de) | 2009-01-28 | 2010-08-05 | Basf Se | Verfahren zur isolierung von dodecatrienal und seine verwendung als aromastoff |
| US8188320B2 (en) | 2009-01-28 | 2012-05-29 | Basf Se | Process for preparing pure cyclododecanone |
| DE102014212602A1 (de) | 2013-07-02 | 2015-01-08 | Basf Se | Verfahren zur Herstellung eines Ketons aus einem Olefin |
Also Published As
| Publication number | Publication date |
|---|---|
| CH446312A (de) | 1967-11-15 |
| NL139294B (nl) | 1973-07-16 |
| US3317620A (en) | 1967-05-02 |
| GB1022875A (en) | 1966-03-16 |
| DE1288087B (de) | 1969-01-30 |
| NL6403826A (enExample) | 1964-10-12 |
| BE646244A (enExample) | 1900-01-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2421934C2 (de) | Verfahren zur Hydrierung von ungesättigten Verbindungen | |
| DE2405856B2 (de) | Verfahren zur Cyclodimerisation von Isopren mittels eines Verbindungen des Eisens und des Stickstoffmonoxids und organische Aluminiumverbindungen enthaltenden Mischkalalysatorsystems | |
| DE1244770B (de) | Verfahren zur Herstellung von im wesentlichen Cyclooctadien-(1, 5) und gegebenenfalls Cyclododecatrien-(1, 5, 9) enthaltenden Kohlenwasserstoffgemischen | |
| EP0844994B1 (de) | Verfahren zur herstellung von butyrolactonen | |
| EP0048378B1 (de) | Verfahren zur Herstellung ungesättigter Kohlenwasserstoffe | |
| DE1230023B (de) | Verfahren zur Herstellung von cis, cis-Cyclodecadien-(1, 6) | |
| DE2412191A1 (de) | Verfahren zur reinigung des butadien und des isopren durch selektive hydrierung der darin enthaltenen acetylenischen verunreinigungen | |
| DE2149934C3 (de) | Verfahren zur Herstellung von ungesättigten Kohlenwasserstoffverbindungen | |
| DE1246724B (de) | Verfahren zur Herstellung von Cyclohexen, Methyl- oder Dimethylcyclohexen | |
| DE1235308B (de) | Verfahren zur Herstellung von C-C-Cycloalkenen | |
| DE1518236A1 (de) | Katalytische Verfahren | |
| DE1493221C (enExample) | ||
| DE1493037A1 (de) | Verfahren zur Herstellung polycyclischer Verbindungen | |
| DE1810185B2 (de) | Nickel (0)-katalysatoren, Verfahren zu deren Herstellung und deren Verwendung zur Oligomerisation von Butadien | |
| DE2551586C2 (de) | Verfahren zur Herstellung von 1,5-Dimethylcycloocten | |
| DE1937495B2 (de) | Verfahren zur Disproportionierung von Olefinen | |
| EP0212708B1 (de) | Verfahren zur Hydroborierung von Alkenen und Alkinen | |
| DE1233862B (de) | Verfahren zur Herstellung von teilweise hydrierten Bicycloheptadien-Dimeren | |
| DE69312433T2 (de) | Verfahren zur selektiven Hydrierung von Verbindungen mit endo- und exocyklischen ungesältigten Bindungen | |
| DE2026043A1 (enExample) | ||
| DE1130804B (de) | Verfahren zur selektiven Hydrierung von staerker als ein Monoolefin ungesaettigten alicyclischen Kohlenwasserstoffen | |
| AT246721B (de) | Verfahren zur Herstellung des neuen cis,cis-Cyclodecadiens-(1,6) | |
| DE3001795A1 (de) | Verfahren zur isomerisierung eines gesaettigten hexacyclischen endo-endo- norbornadien-dimeren | |
| DE2221253A1 (de) | Verfahren zur disproportionierung von diallylaminen | |
| DE2028179A1 (de) | Verfahren zur Herstellung von 4-Alkoxy-piperidinen |