FR2486933A1 - Procede de preparation d'un carburant a haute energie, l'exo-tetra-hydrodicyclopentadiene - Google Patents
Procede de preparation d'un carburant a haute energie, l'exo-tetra-hydrodicyclopentadiene Download PDFInfo
- Publication number
- FR2486933A1 FR2486933A1 FR8015839A FR8015839A FR2486933A1 FR 2486933 A1 FR2486933 A1 FR 2486933A1 FR 8015839 A FR8015839 A FR 8015839A FR 8015839 A FR8015839 A FR 8015839A FR 2486933 A1 FR2486933 A1 FR 2486933A1
- Authority
- FR
- France
- Prior art keywords
- sep
- endo
- hydrogenation
- exo
- dicyclopentadiene
- 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.)
- Granted
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims abstract description 18
- 238000006317 isomerization reaction Methods 0.000 title claims description 17
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 title claims description 6
- 239000000446 fuel Substances 0.000 title abstract description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims abstract description 28
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- 239000010802 sludge Substances 0.000 claims abstract description 6
- 239000012442 inert solvent Substances 0.000 claims abstract description 5
- LPSXSORODABQKT-YNFQOJQRSA-N (3ar,4r,7s,7as)-rel-octahydro-1h-4,7-methanoindene Chemical compound C([C@H]1C2)C[C@H]2[C@@H]2[C@H]1CCC2 LPSXSORODABQKT-YNFQOJQRSA-N 0.000 claims abstract 6
- 238000000034 method Methods 0.000 claims description 9
- LPSXSORODABQKT-FIRGSJFUSA-N exo-trimethylenenorbornane Chemical compound C([C@@H]1C2)C[C@@H]2[C@@H]2[C@H]1CCC2 LPSXSORODABQKT-FIRGSJFUSA-N 0.000 claims description 7
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000000539 dimer Substances 0.000 claims 2
- 239000012043 crude product Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 12
- HECLRDQVFMWTQS-SGIHWFKDSA-N (1R,2R,6R,7S)-tricyclo[5.2.1.02,6]deca-3,8-diene Chemical compound C1[C@@H]2[C@H]3CC=C[C@@H]3[C@H]1C=C2 HECLRDQVFMWTQS-SGIHWFKDSA-N 0.000 abstract 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 238000011068 loading method Methods 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000002841 Lewis acid Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 238000007710 freezing Methods 0.000 description 2
- 230000008014 freezing Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000007517 lewis acids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000005499 meniscus Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- LPSXSORODABQKT-UHFFFAOYSA-N tetrahydrodicyclopentadiene Chemical compound C1C2CCC1C1C2CCC1 LPSXSORODABQKT-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 1
- NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-decalin Chemical compound C1CCC[C@@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-MGCOHNPYSA-N 0.000 description 1
Classifications
-
- 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
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- 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
- C07C5/2206—Catalytic processes not covered by C07C5/23 - C07C5/31
- C07C5/2226—Catalytic processes not covered by C07C5/23 - C07C5/31 with inorganic acids; with salt or anhydrides of acids
- C07C5/2246—Acids of halogen; Salts thereof
- C07C5/2253—Metal halides; Complexes thereof with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2523/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00
- C07C2523/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group C07C2521/00 of the iron group metals or copper
- C07C2523/74—Iron group metals
- C07C2523/755—Nickel
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
-
- 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)
- Inorganic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8015839A FR2486933A1 (fr) | 1980-07-17 | 1980-07-17 | Procede de preparation d'un carburant a haute energie, l'exo-tetra-hydrodicyclopentadiene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8015839A FR2486933A1 (fr) | 1980-07-17 | 1980-07-17 | Procede de preparation d'un carburant a haute energie, l'exo-tetra-hydrodicyclopentadiene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2486933A1 true FR2486933A1 (fr) | 1982-01-22 |
| FR2486933B1 FR2486933B1 (member.php) | 1983-12-02 |
Family
ID=9244255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8015839A Granted FR2486933A1 (fr) | 1980-07-17 | 1980-07-17 | Procede de preparation d'un carburant a haute energie, l'exo-tetra-hydrodicyclopentadiene |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2486933A1 (member.php) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2752508C1 (ru) * | 2020-10-21 | 2021-07-28 | Федеральное государственное бюджетное учреждение науки Ордена Трудового Красного Знамени Институт нефтехимического синтеза им. А.В. Топчиева Российской академии наук (ИНХС РАН) | Способ получения катализатора и способ получения экзо-тетрагидродициклопентадиена в его присутствии |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011418B (de) * | 1953-05-07 | 1957-07-04 | Ruhrchemie Ag | Verfahren zur Herstellung von reinstem Tricyclodekan aus Dicyclopentadien |
| FR1537241A (fr) * | 1966-08-15 | 1968-08-23 | Exxon Research Engineering Co | Préparation de carburants possédant un potentiel d'énergie élevé |
| US4086284A (en) * | 1976-09-03 | 1978-04-25 | Suntech, Inc. | Isomerization of endo-tetrahydrodicyclopentadiene to a missile fuel diluent |
| US4177217A (en) * | 1977-09-28 | 1979-12-04 | Suntech, Inc. | Continuous process for conversion of dimethyldicyclopentadiene to endo-dimethyldicyclopentadiene, a missile fuel |
-
1980
- 1980-07-17 FR FR8015839A patent/FR2486933A1/fr active Granted
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1011418B (de) * | 1953-05-07 | 1957-07-04 | Ruhrchemie Ag | Verfahren zur Herstellung von reinstem Tricyclodekan aus Dicyclopentadien |
| FR1537241A (fr) * | 1966-08-15 | 1968-08-23 | Exxon Research Engineering Co | Préparation de carburants possédant un potentiel d'énergie élevé |
| US4086284A (en) * | 1976-09-03 | 1978-04-25 | Suntech, Inc. | Isomerization of endo-tetrahydrodicyclopentadiene to a missile fuel diluent |
| US4177217A (en) * | 1977-09-28 | 1979-12-04 | Suntech, Inc. | Continuous process for conversion of dimethyldicyclopentadiene to endo-dimethyldicyclopentadiene, a missile fuel |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2486933B1 (member.php) | 1983-12-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |