DE1668680B1 - Verfahren zur Ausfuehrung einer Dien-Synthese mit in 6-Stellung substituierten Fulven-Kohlenwasserstoffen bei erhoehten Temperaturen und unter erhoehtem Druck - Google Patents
Verfahren zur Ausfuehrung einer Dien-Synthese mit in 6-Stellung substituierten Fulven-Kohlenwasserstoffen bei erhoehten Temperaturen und unter erhoehtem DruckInfo
- Publication number
- DE1668680B1 DE1668680B1 DE19681668680 DE1668680A DE1668680B1 DE 1668680 B1 DE1668680 B1 DE 1668680B1 DE 19681668680 DE19681668680 DE 19681668680 DE 1668680 A DE1668680 A DE 1668680A DE 1668680 B1 DE1668680 B1 DE 1668680B1
- Authority
- DE
- Germany
- Prior art keywords
- fulvene
- reaction
- butadiene
- hydrocarbons
- elevated temperatures
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 8
- 229930195733 hydrocarbon Natural products 0.000 title claims 7
- 230000015572 biosynthetic process Effects 0.000 title claims 3
- 150000001993 dienes Chemical class 0.000 title claims 3
- 238000003786 synthesis reaction Methods 0.000 title claims 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims description 22
- 239000000047 product Substances 0.000 claims description 18
- -1 diene hydrocarbon Chemical class 0.000 claims description 7
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 6
- WXACXMWYHXOSIX-UHFFFAOYSA-N 5-propan-2-ylidenecyclopenta-1,3-diene Chemical compound CC(C)=C1C=CC=C1 WXACXMWYHXOSIX-UHFFFAOYSA-N 0.000 claims description 5
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 4
- 238000005194 fractionation Methods 0.000 claims description 4
- XPFMXIFLVOALLW-UHFFFAOYSA-N 5-(2,6-dimethylheptan-4-ylidene)cyclopenta-1,3-diene Chemical compound CC(C)CC(CC(C)C)=C1C=CC=C1 XPFMXIFLVOALLW-UHFFFAOYSA-N 0.000 claims description 3
- IGSGWPUSCLPKER-UHFFFAOYSA-N cyclopenta-2,4-dien-1-ylidenemethylbenzene Chemical compound C=1C=CC=CC=1C=C1C=CC=C1 IGSGWPUSCLPKER-UHFFFAOYSA-N 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- ACGLURQVVOLIOD-UHFFFAOYSA-N 5-ethylidenecyclopenta-1,3-diene Chemical compound CC=C1C=CC=C1 ACGLURQVVOLIOD-UHFFFAOYSA-N 0.000 claims description 2
- XDCVKINZRQNSTP-UHFFFAOYSA-N 5-pentan-3-ylidenecyclopenta-1,3-diene Chemical compound CCC(CC)=C1C=CC=C1 XDCVKINZRQNSTP-UHFFFAOYSA-N 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- 238000011835 investigation Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 7
- PGTKVMVZBBZCKQ-UHFFFAOYSA-N Fulvene Chemical compound C=C1C=CC=C1 PGTKVMVZBBZCKQ-UHFFFAOYSA-N 0.000 claims 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 150000002234 fulvenes Chemical class 0.000 claims 4
- 238000005698 Diels-Alder reaction Methods 0.000 claims 3
- 238000009833 condensation Methods 0.000 claims 3
- 230000005494 condensation Effects 0.000 claims 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 238000004458 analytical method Methods 0.000 claims 2
- XZKRXPZXQLARHH-UHFFFAOYSA-N buta-1,3-dienylbenzene Chemical compound C=CC=CC1=CC=CC=C1 XZKRXPZXQLARHH-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- WARFUBGCFNEAIP-UHFFFAOYSA-N 1-ethyl-5-methylidenecyclopenta-1,3-diene Chemical compound CCC1=CC=CC1=C WARFUBGCFNEAIP-UHFFFAOYSA-N 0.000 claims 1
- YNFFKFCAFJYGRA-UHFFFAOYSA-N 1-methyl-5-methylidenecyclopenta-1,3-diene Chemical compound CC1=CC=CC1=C YNFFKFCAFJYGRA-UHFFFAOYSA-N 0.000 claims 1
- HRYYXFYLNRICQD-UHFFFAOYSA-N 5-butan-2-ylidenecyclopenta-1,3-diene Chemical compound CCC(C)=C1C=CC=C1 HRYYXFYLNRICQD-UHFFFAOYSA-N 0.000 claims 1
- 235000007487 Calathea allouia Nutrition 0.000 claims 1
- 244000278792 Calathea allouia Species 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 230000007423 decrease Effects 0.000 claims 1
- 238000004817 gas chromatography Methods 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000003367 polycyclic group Chemical group 0.000 claims 1
- 229920000642 polymer Polymers 0.000 claims 1
- 230000007425 progressive decline Effects 0.000 claims 1
- 238000012552 review Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 229910001220 stainless steel Inorganic materials 0.000 claims 1
- 239000010935 stainless steel Substances 0.000 claims 1
- 229920001897 terpolymer Polymers 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/27—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system containing six carbon atoms
-
- 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
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/45—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing nine carbon atoms
- C07C13/465—Indenes; Completely or partially hydrogenated indenes
-
- 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
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/547—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings at least one ring not being six-membered, the other rings being at the most six-membered
-
- 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
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
- C07C13/54—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings
- C07C13/605—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system
- C07C13/61—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with three condensed rings with a bridged ring system with a bridged indene ring, e.g. dicyclopentadiene
-
- 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
- C07C2/50—Diels-Alder conversion
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/24—All rings being cycloaliphatic the ring system containing nine carbon atoms, e.g. perhydroindane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/14—Benz[f]indenes; Hydrogenated benz[f]indenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1363767 | 1967-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1668680B1 true DE1668680B1 (de) | 1972-05-31 |
Family
ID=11144553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681668680 Withdrawn DE1668680B1 (de) | 1967-03-13 | 1968-03-05 | Verfahren zur Ausfuehrung einer Dien-Synthese mit in 6-Stellung substituierten Fulven-Kohlenwasserstoffen bei erhoehten Temperaturen und unter erhoehtem Druck |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3591648A (esLanguage) |
| BE (1) | BE712010A (esLanguage) |
| DE (1) | DE1668680B1 (esLanguage) |
| FR (1) | FR1570533A (esLanguage) |
| LU (1) | LU55651A1 (esLanguage) |
| NL (1) | NL6803536A (esLanguage) |
-
1968
- 1968-03-05 DE DE19681668680 patent/DE1668680B1/de not_active Withdrawn
- 1968-03-07 FR FR1570533D patent/FR1570533A/fr not_active Expired
- 1968-03-09 LU LU55651D patent/LU55651A1/xx unknown
- 1968-03-11 BE BE712010D patent/BE712010A/xx not_active IP Right Cessation
- 1968-03-11 US US711917A patent/US3591648A/en not_active Expired - Lifetime
- 1968-03-13 NL NL6803536A patent/NL6803536A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| None * |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6803536A (esLanguage) | 1968-09-16 |
| BE712010A (esLanguage) | 1968-07-15 |
| US3591648A (en) | 1971-07-06 |
| FR1570533A (esLanguage) | 1969-06-13 |
| LU55651A1 (esLanguage) | 1968-05-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |