US3676511A - Polyene hydrocarbons containing two conjugated double bonds and process for obtaining same - Google Patents
Polyene hydrocarbons containing two conjugated double bonds and process for obtaining same Download PDFInfo
- Publication number
- US3676511A US3676511A US109009A US3676511DA US3676511A US 3676511 A US3676511 A US 3676511A US 109009 A US109009 A US 109009A US 3676511D A US3676511D A US 3676511DA US 3676511 A US3676511 A US 3676511A
- Authority
- US
- United States
- Prior art keywords
- double bonds
- conjugated double
- polyene hydrocarbons
- hydrocarbons containing
- obtaining same
- 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 - Lifetime
Links
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 14
- -1 Polyene hydrocarbons Chemical class 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title description 2
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 150000000475 acetylene derivatives Chemical class 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 8
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- MDSPECLCFVWIGQ-UHFFFAOYSA-N 2-bromoprop-2-enal Chemical compound BrC(=C)C=O MDSPECLCFVWIGQ-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- 241000231258 Suillus granulatus Species 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005671 trienes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07C35/28—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 seven carbon atoms
- C07C35/29—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 seven carbon atoms being a (2.2.1) system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
- C07C1/326—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being a magnesium atom
-
- 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
- C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven 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
- C07C13/39—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms
- C07C13/42—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure
- C07C13/43—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings with a bicyclo ring system containing seven carbon atoms with a bicycloheptene ring structure substituted by unsaturated acyclic hydrocarbon
-
- 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
- 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
- C07C2/52—Catalytic processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Definitions
- R is hydrogen or an alkyl radical
- R,, R R R R R R" and R may be hydrogen, alkyl or aryl radicals.
- hydrocarbons are obtained by reacting a substituted or unsubstituted norbornene carbonyl derivative with a Grignard alkenyl derivative, for example according to the fol lowing scheme:
- R R R R R, R', R" and R have the aforesaid meanings and X is a halogen as Br, C1 or I.
- R C C Cal I 1 R! R!!! Its- All the above reactions are carried out at a temperature ranging from 0 to C, and preferably in the presence of a solvent which may be selected from ethers as tetrahydrofuran, dioxane, ethyl ether, butyl ether, and the like, from aromatic hydrocarbons as benzene, toluene, xylenes or mixtures of these solvents.
- a solvent which may be selected from ethers as tetrahydrofuran, dioxane, ethyl ether, butyl ether, and the like, from aromatic hydrocarbons as benzene, toluene, xylenes or mixtures of these solvents.
- Typical unrestrictive examples of triene derivatives according to the present invention are the following ones:
- reaction mass was allowed to reflow for 2 hours: then the magnesium salts were dissolved by an excess of a watery CH COOH (1:1 by volume), the organic phase was washed up to neutrality, dried on Ne so and the tetrahydrofuran was removed by distillation.
- R is hydrogen or an alkyl radical
- R,, R R R R, R" and R' are hydrogen, alkyl or aryl radicals.
- a process for preparing polyene hydrocarbons as claimed in claim 1 characterized in that said hydrocarbons are obtained by reacting a Grignard derivative as:
- R, R R R R R, R", R and X have the aforesaid meanings.
- a process for preparing polyene hydrocarbons as claimed in claim 1 characterized in that cyclopentadiene is allowed to react with an acetylene derivative containing at least a double bond conjugated with the triple 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)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1966070 | 1970-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3676511A true US3676511A (en) | 1972-07-11 |
Family
ID=11160161
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US109009A Expired - Lifetime US3676511A (en) | 1970-01-22 | 1971-01-22 | Polyene hydrocarbons containing two conjugated double bonds and process for obtaining same |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3676511A (enExample) |
| JP (1) | JPS5242792B1 (enExample) |
| AT (3) | AT314496B (enExample) |
| BE (1) | BE761745A (enExample) |
| CA (1) | CA976989A (enExample) |
| CH (1) | CH534645A (enExample) |
| DE (1) | DE2102972A1 (enExample) |
| FR (1) | FR2075697A5 (enExample) |
| GB (1) | GB1337074A (enExample) |
| LU (1) | LU62467A1 (enExample) |
| NL (1) | NL7100918A (enExample) |
| ZA (1) | ZA71424B (enExample) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2966527A (en) * | 1956-10-09 | 1960-12-27 | Universal Oil Prod Co | Preparation of bicycloalkadienes |
| US3347875A (en) * | 1965-02-19 | 1967-10-17 | Union Carbide Corp | Acetylenic epoxides and dienes |
| US3565961A (en) * | 1969-05-15 | 1971-02-23 | Sumitomo Chemical Co | Process for producing 5-(1'-alkenyl)-2-norbornene |
-
1971
- 1971-01-19 BE BE761745A patent/BE761745A/xx unknown
- 1971-01-19 CA CA103,123A patent/CA976989A/en not_active Expired
- 1971-01-19 FR FR7101619A patent/FR2075697A5/fr not_active Expired
- 1971-01-21 LU LU62467D patent/LU62467A1/xx unknown
- 1971-01-22 US US109009A patent/US3676511A/en not_active Expired - Lifetime
- 1971-01-22 NL NL7100918A patent/NL7100918A/xx unknown
- 1971-01-22 JP JP46001664A patent/JPS5242792B1/ja active Pending
- 1971-01-22 AT AT620072A patent/AT314496B/de not_active IP Right Cessation
- 1971-01-22 AT AT54571A patent/AT305969B/de not_active IP Right Cessation
- 1971-01-22 ZA ZA710424A patent/ZA71424B/xx unknown
- 1971-01-22 DE DE19712102972 patent/DE2102972A1/de active Pending
- 1971-01-22 AT AT347672A patent/AT310717B/de not_active IP Right Cessation
- 1971-01-22 CH CH103771A patent/CH534645A/fr not_active IP Right Cessation
- 1971-04-19 GB GB2041771A patent/GB1337074A/en not_active Expired
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2966527A (en) * | 1956-10-09 | 1960-12-27 | Universal Oil Prod Co | Preparation of bicycloalkadienes |
| US3347875A (en) * | 1965-02-19 | 1967-10-17 | Union Carbide Corp | Acetylenic epoxides and dienes |
| US3565961A (en) * | 1969-05-15 | 1971-02-23 | Sumitomo Chemical Co | Process for producing 5-(1'-alkenyl)-2-norbornene |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7100918A (enExample) | 1971-07-26 |
| DE2102972A1 (de) | 1972-02-17 |
| AT314496B (de) | 1974-04-10 |
| AT305969B (de) | 1973-03-26 |
| GB1337074A (en) | 1973-11-14 |
| BE761745A (fr) | 1971-07-01 |
| CH534645A (fr) | 1973-03-15 |
| JPS5242792B1 (enExample) | 1977-10-26 |
| ZA71424B (en) | 1971-10-27 |
| LU62467A1 (enExample) | 1971-09-02 |
| FR2075697A5 (enExample) | 1971-10-08 |
| AT310717B (de) | 1973-10-10 |
| CA976989A (en) | 1975-10-28 |
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