DE1239304B - Verfahren zur Herstellung der Dimeren des Bicyclo-[2, 2, 1]-heptadiens-2, 5 und seiner unterhalb 140 siedenden Alkylderivate - Google Patents
Verfahren zur Herstellung der Dimeren des Bicyclo-[2, 2, 1]-heptadiens-2, 5 und seiner unterhalb 140 siedenden AlkylderivateInfo
- Publication number
- DE1239304B DE1239304B DES100715A DES0100715A DE1239304B DE 1239304 B DE1239304 B DE 1239304B DE S100715 A DES100715 A DE S100715A DE S0100715 A DES0100715 A DE S0100715A DE 1239304 B DE1239304 B DE 1239304B
- Authority
- DE
- Germany
- Prior art keywords
- dimers
- bch
- bicyclo
- heptadiene
- iron
- 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
- 239000000539 dimer Substances 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 22
- 238000009835 boiling Methods 0.000 title claims description 9
- 125000000217 alkyl group Chemical group 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 28
- 239000003054 catalyst Substances 0.000 claims description 21
- 238000006471 dimerization reaction Methods 0.000 claims description 14
- 229910052742 iron Inorganic materials 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 12
- 230000003647 oxidation Effects 0.000 claims description 9
- 238000007254 oxidation reaction Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 6
- 239000003446 ligand Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- 230000000737 periodic effect Effects 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000203 mixture Substances 0.000 description 14
- 238000010924 continuous production Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000007711 solidification Methods 0.000 description 5
- 230000008023 solidification Effects 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 239000003638 chemical reducing agent Substances 0.000 description 4
- 239000000446 fuel Substances 0.000 description 4
- 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 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 3
- 229940087654 iron carbonyl Drugs 0.000 description 3
- -1 metal complex compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 150000002506 iron compounds Chemical class 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- JGUQDUKBUKFFRO-GGWOSOGESA-N (NE)-N-[(3E)-3-hydroxyiminobutan-2-ylidene]hydroxylamine Chemical class O\N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-GGWOSOGESA-N 0.000 description 1
- CDVAIHNNWWJFJW-UHFFFAOYSA-N 3,5-diethoxycarbonyl-1,4-dihydrocollidine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C CDVAIHNNWWJFJW-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000000447 dimerizing effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000004698 iron complex Chemical class 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- BMGNSKKZFQMGDH-FDGPNNRMSA-L nickel(2+);(z)-4-oxopent-2-en-2-olate Chemical compound [Ni+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O BMGNSKKZFQMGDH-FDGPNNRMSA-L 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07C2/42—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons homo- or co-oligomerisation with ring formation, not being a Diels-Alder conversion
-
- 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
-
- 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
- C07C2603/90—Ring systems containing bridged rings containing more than four rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES100715A DE1239304B (de) | 1965-11-29 | 1965-11-29 | Verfahren zur Herstellung der Dimeren des Bicyclo-[2, 2, 1]-heptadiens-2, 5 und seiner unterhalb 140 siedenden Alkylderivate |
| US542739A US3377398A (en) | 1965-11-29 | 1966-04-15 | Dimerization process |
| FR85183A FR1517799A (fr) | 1965-11-29 | 1966-11-28 | Procédé de préparation de dimères du bicyclo-[2, 2, 1]hepta-2, 5-diène et de ses dérivés alcoylés |
| NL6616689A NL6616689A (en:Method) | 1965-11-29 | 1966-11-28 | |
| GB53095/66A GB1108379A (en) | 1965-11-29 | 1966-11-28 | Process for the preparation of dimers of bicyclo-[2,2,1]-hepta-2,5-diene and its alkyl derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES100715A DE1239304B (de) | 1965-11-29 | 1965-11-29 | Verfahren zur Herstellung der Dimeren des Bicyclo-[2, 2, 1]-heptadiens-2, 5 und seiner unterhalb 140 siedenden Alkylderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1239304B true DE1239304B (de) | 1967-04-27 |
Family
ID=7523251
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DES100715A Pending DE1239304B (de) | 1965-11-29 | 1965-11-29 | Verfahren zur Herstellung der Dimeren des Bicyclo-[2, 2, 1]-heptadiens-2, 5 und seiner unterhalb 140 siedenden Alkylderivate |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3377398A (en:Method) |
| DE (1) | DE1239304B (en:Method) |
| FR (1) | FR1517799A (en:Method) |
| GB (1) | GB1108379A (en:Method) |
| NL (1) | NL6616689A (en:Method) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3440294A (en) * | 1967-04-07 | 1969-04-22 | Union Carbide Corp | Oligomers of bicycloheptadiene |
| US3671597A (en) * | 1970-07-17 | 1972-06-20 | Exxon Research Engineering Co | Isomerization process employing a novel heterogeneous catalyst |
| US4031150A (en) * | 1975-11-14 | 1977-06-21 | Suntech, Inc. | Catalytic dimerization of norbornadiene to Binor-S |
| US4087257A (en) * | 1977-03-21 | 1978-05-02 | The United States Of America As Represented By The Secretary Of The Navy | High density-high volumetric heating value liquid ramjet |
| US4401837A (en) * | 1980-06-02 | 1983-08-30 | The United States Of America As Represented By The Secretary Of The Navy | Exo-tetrahydrotricyclopentadiene, a high density liquid fuel |
| KR101616071B1 (ko) | 2015-10-21 | 2016-04-27 | 국방과학연구소 | 불균일계 촉매를 이용한 노르보나디엔 이량체의 제조 방법 |
| KR101976075B1 (ko) | 2018-03-30 | 2019-08-28 | 국방과학연구소 | 고에너지밀도 연료 조성물의 제조방법 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE626407A (en:Method) * |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1197083B (de) * | 1961-12-27 | 1965-07-22 | Shell Int Research | Verfahren zur Herstellung von Dimeren und Trimeren des Bicyclo-[2, 2, 1]-heptadiens-(2, 5) |
-
1965
- 1965-11-29 DE DES100715A patent/DE1239304B/de active Pending
-
1966
- 1966-04-15 US US542739A patent/US3377398A/en not_active Expired - Lifetime
- 1966-11-28 FR FR85183A patent/FR1517799A/fr not_active Expired
- 1966-11-28 GB GB53095/66A patent/GB1108379A/en not_active Expired
- 1966-11-28 NL NL6616689A patent/NL6616689A/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE626407A (en:Method) * |
Also Published As
| Publication number | Publication date |
|---|---|
| FR1517799A (fr) | 1968-03-22 |
| US3377398A (en) | 1968-04-09 |
| NL6616689A (en:Method) | 1967-05-30 |
| GB1108379A (en) | 1968-04-03 |
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