AT246721B - Process for the preparation of the new cis, cis-cyclodecadiene- (1,6) - Google Patents
Process for the preparation of the new cis, cis-cyclodecadiene- (1,6)Info
- Publication number
- AT246721B AT246721B AT282664A AT282664A AT246721B AT 246721 B AT246721 B AT 246721B AT 282664 A AT282664 A AT 282664A AT 282664 A AT282664 A AT 282664A AT 246721 B AT246721 B AT 246721B
- Authority
- AT
- Austria
- Prior art keywords
- cis
- cyclodecadiene
- preparation
- new
- trans
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 229910052697 platinum Inorganic materials 0.000 claims 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- MZJCFRKLOXHQIL-UHFFFAOYSA-N (1Z,3E)-cyclodeca-1,3-diene Chemical compound C/1=CC=C/CCCCCC1 MZJCFRKLOXHQIL-UHFFFAOYSA-N 0.000 description 1
- MZJCFRKLOXHQIL-CCAGOZQPSA-N (1Z,3Z)-cyclodeca-1,3-diene Chemical compound C1CCC\C=C/C=C\CC1 MZJCFRKLOXHQIL-CCAGOZQPSA-N 0.000 description 1
- MZJCFRKLOXHQIL-WZNPJAPVSA-N (3e)-cyclodeca-1,3-diene Chemical compound C1CCC\C=C\C=CCC1 MZJCFRKLOXHQIL-WZNPJAPVSA-N 0.000 description 1
- 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
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 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
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- -1 transition metal acetylacetonate Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Herstellung des neuen cis, cis-Cyclodecadiens- (1, 6)
EMI1.1
EMI1.2
EMI1.3
EMI1.4
EMI1.5
<Desc/Clms Page number 2>
Durch das erfindungsgemässe Verfahren kann somit das aus Butadien und Äthylen herstellbare, thermisch aber instabil trans, cis-Cyclodecadien- (l, 5) in ein stabiles Isomeres umgewandelt werden. Es empfielt sich, das gemäss Patentschrift Nr. 232495 anfallende Reaktionsprodukt, das das Cyclodecadien- (l, 5) enthält, zunächst einer Isomerisierung zu unterwerfen und dann erst die 10-Ring-Komponente in Form des neuen stabilen Isomeren, z. B. durch Destillation, zu isolieren. Das cis, cis-Cyc1odecadien- (1, 6) ist dann auch Folgereaktionen zugänglich, die bei höheren Temperaturen ablaufen.
Bei dem Verfahren der nachstehenden Beispiele 1 bis 4 wurde wie folgt gearbeitet :
Je 1 g eines Übergangsmetall-acetylacetonates werden in 10 ml Benzol oder einem der vorstehend genannten Lösungsmittel gelöst oder suspendiert und mit 1 Mol Aluminiumtriäthyl pro Äquivalent Metallacetylacetonat reduziert. Nach Zugabe von jeweils 10 g cis, trans-Cyclodecadien- (1, 5) erhitzt man 24 h unter Rühren auf 80-90 C. Nach Abdestillieren vom Katalysator wird die Zusammensetzung des Reaktionsproduktes gaschromatographisch ermittelt.
EMI2.1
:cis, cis-Cyclodecadien- (1, 6) isolieren.
PATENTANSPRÜCHE :
1. Verfahren zur Herstellung des neuen cis, cis-Cyclodecadiens- (1, 6), dadurch gekennzeichnet, dass man auf trans, cis-Cyclodecadien- (l, 5) katalytische Mengen von aktiven Metallen der VIII. Gruppe des Periodensystems bei Temperaturen von 0 bis 1000 C einwirken lässt.
<Desc / Clms Page number 1>
Process for the preparation of the new cis, cis-cyclodecadiene- (1, 6)
EMI1.1
EMI1.2
EMI1.3
EMI1.4
EMI1.5
<Desc / Clms Page number 2>
The process according to the invention can thus convert the thermally but unstable trans, cis-cyclodecadiene- (1.5) which can be prepared from butadiene and ethylene into a stable isomer. It is advisable to first subject the reaction product obtained according to patent specification No. 232495, which contains the cyclodecadiene (l, 5), to an isomerization and only then to subject the 10-ring component in the form of the new stable isomer, e.g. B. by distillation to isolate. The cis, cis-cycodecadiene (1, 6) is then also accessible to subsequent reactions which take place at higher temperatures.
The procedure of Examples 1 to 4 below was carried out as follows:
1 g of a transition metal acetylacetonate is dissolved or suspended in 10 ml of benzene or one of the abovementioned solvents and reduced with 1 mol of aluminum triethyl per equivalent of metal acetylacetonate. After adding 10 g of cis, trans-cyclodecadiene (1, 5) in each case, the mixture is heated to 80-90 ° C. for 24 hours with stirring. After the catalyst has been distilled off, the composition of the reaction product is determined by gas chromatography.
EMI2.1
: isolate cis, cis-cyclodecadiene- (1, 6).
PATENT CLAIMS:
1. A process for the preparation of the new cis, cis-cyclodecadiene (1, 6), characterized in that on trans, cis-cyclodecadiene (l, 5) catalytic amounts of active metals of Group VIII of the Periodic Table at temperatures of From 0 to 1000 C.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE246721X | 1963-04-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT246721B true AT246721B (en) | 1966-05-10 |
Family
ID=5935186
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT282664A AT246721B (en) | 1963-04-10 | 1964-04-01 | Process for the preparation of the new cis, cis-cyclodecadiene- (1,6) |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT246721B (en) |
-
1964
- 1964-04-01 AT AT282664A patent/AT246721B/en active
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