DE2425289C3 - Verfahren zur Herstellung von Cyclopenten aus Dicyclopentadien durch thermische Spaltung in flüssiger Phase und Hydrierung - Google Patents
Verfahren zur Herstellung von Cyclopenten aus Dicyclopentadien durch thermische Spaltung in flüssiger Phase und HydrierungInfo
- Publication number
- DE2425289C3 DE2425289C3 DE2425289A DE2425289A DE2425289C3 DE 2425289 C3 DE2425289 C3 DE 2425289C3 DE 2425289 A DE2425289 A DE 2425289A DE 2425289 A DE2425289 A DE 2425289A DE 2425289 C3 DE2425289 C3 DE 2425289C3
- Authority
- DE
- Germany
- Prior art keywords
- cyclopentene
- dicyclopentadiene
- cleavage
- cyclopentadiene
- weight
- 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
Links
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title claims description 86
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims description 63
- 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 53
- 238000003776 cleavage reaction Methods 0.000 title claims description 34
- 230000007017 scission Effects 0.000 title claims description 34
- 238000000034 method Methods 0.000 title claims description 29
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 13
- 239000007791 liquid phase Substances 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 57
- 238000009835 boiling Methods 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 11
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 238000005194 fractionation Methods 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 7
- KXYDGGNWZUHESZ-UHFFFAOYSA-N 4-(2,2,4-trimethyl-3h-chromen-4-yl)phenol Chemical compound C12=CC=CC=C2OC(C)(C)CC1(C)C1=CC=C(O)C=C1 KXYDGGNWZUHESZ-UHFFFAOYSA-N 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- HSQZKZLSYKJDJR-UHFFFAOYSA-N cyclopentane cyclopentene Chemical compound C1CCCC1.C1CC=CC1 HSQZKZLSYKJDJR-UHFFFAOYSA-N 0.000 claims description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052744 lithium Inorganic materials 0.000 claims description 3
- 229910052596 spinel Inorganic materials 0.000 claims description 3
- 239000011029 spinel Substances 0.000 claims description 3
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 230000007423 decrease Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 description 15
- 150000002430 hydrocarbons Chemical class 0.000 description 14
- 239000000203 mixture Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- 239000007789 gas Substances 0.000 description 6
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 238000004939 coking Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000011144 upstream manufacturing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 125000002015 acyclic group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000002826 coolant Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 238000000895 extractive distillation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- -1 steam Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 238000007669 thermal treatment Methods 0.000 description 1
- 230000007704 transition Effects 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
- C07C13/02—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/08—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring
- C07C13/12—Monocyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with a five-membered ring with a cyclopentene ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C4/00—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms
- C07C4/22—Preparation of hydrocarbons from hydrocarbons containing a larger number of carbon atoms by depolymerisation to the original monomer, e.g. dicyclopentadiene to cyclopentadiene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S585/00—Chemistry of hydrocarbon compounds
- Y10S585/8995—Catalyst and recycle considerations
- Y10S585/901—Catalyst and recycle considerations with recycle, rehabilitation, or preservation of solvent, diluent, or mass action agent
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2425289A DE2425289C3 (de) | 1974-05-24 | 1974-05-24 | Verfahren zur Herstellung von Cyclopenten aus Dicyclopentadien durch thermische Spaltung in flüssiger Phase und Hydrierung |
| US05/575,661 US4048242A (en) | 1974-05-24 | 1975-05-08 | Process for the production of cyclopentene from dicyclopentadiene |
| JP6028875A JPS5550009B2 (enExample) | 1974-05-24 | 1975-05-22 | |
| IT49719/75A IT1035824B (it) | 1974-05-24 | 1975-05-22 | Procedimento per la produzione di ciclopentene a partire da diciclopentadiene |
| BE156588A BE829353A (fr) | 1974-05-24 | 1975-05-22 | Procede de fabrication du cyclopentene a partir de dicyclo- pentadiene |
| GB22191/75A GB1505542A (en) | 1974-05-24 | 1975-05-22 | Process for the production of cyclopentene from dicyclopentadiene |
| NL7506041A NL7506041A (nl) | 1974-05-24 | 1975-05-22 | Werkwijze ter bereiding van cyclopenteen uit dicyclopentadieen. |
| FR7516225A FR2272057B1 (enExample) | 1974-05-24 | 1975-05-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2425289A DE2425289C3 (de) | 1974-05-24 | 1974-05-24 | Verfahren zur Herstellung von Cyclopenten aus Dicyclopentadien durch thermische Spaltung in flüssiger Phase und Hydrierung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2425289A1 DE2425289A1 (de) | 1975-12-04 |
| DE2425289B2 DE2425289B2 (de) | 1978-03-16 |
| DE2425289C3 true DE2425289C3 (de) | 1978-11-30 |
Family
ID=5916427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2425289A Expired DE2425289C3 (de) | 1974-05-24 | 1974-05-24 | Verfahren zur Herstellung von Cyclopenten aus Dicyclopentadien durch thermische Spaltung in flüssiger Phase und Hydrierung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4048242A (enExample) |
| JP (1) | JPS5550009B2 (enExample) |
| BE (1) | BE829353A (enExample) |
| DE (1) | DE2425289C3 (enExample) |
| FR (1) | FR2272057B1 (enExample) |
| GB (1) | GB1505542A (enExample) |
| IT (1) | IT1035824B (enExample) |
| NL (1) | NL7506041A (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4329508A (en) * | 1980-09-29 | 1982-05-11 | Scm Corporation | Process for making alkyl cyclopentenones |
| JPS61227537A (ja) * | 1985-04-01 | 1986-10-09 | Sumitomo Chem Co Ltd | 高純度シクロペンタジエンの製造方法 |
| DE19613617A1 (de) * | 1996-04-04 | 1997-10-09 | Basf Ag | Verfahren zur Gewinnung von Cyclopentan und/oder Cyclopenten aus teilhydriertem Pyrolysebenzin |
| US5998683A (en) * | 1996-08-06 | 1999-12-07 | Exxon Chemicals Patents Inc. | Process for forming cyclopentane from dicyclopentadiene |
| US6620982B1 (en) | 1998-10-07 | 2003-09-16 | Equistar Chemicals, Lp | Method of producing purified cyclopentane |
| WO2010073841A1 (ja) * | 2008-12-26 | 2010-07-01 | 新日本石油株式会社 | ジシクロペンタジエンの精製方法 |
| CN103130630B (zh) * | 2013-03-01 | 2014-07-02 | 张若煜 | 环戊酮绿色合成方法 |
| EP4549617A1 (en) | 2023-10-31 | 2025-05-07 | Basf Se | Preparation of saturated or ethylenically unsaturated (cyclo)aliphatic compounds by hydrogenation of ethylenically or acetylenically unsaturated (cyclo)aliphatic compounds using hydrogen with low deuterium content |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2887517A (en) * | 1953-06-29 | 1959-05-19 | Ruhrchemie Ag | Production of cyclopentene |
| US3565963A (en) * | 1969-12-22 | 1971-02-23 | Phillips Petroleum Co | Process for the manufacture of high purity cyclopentene |
| DE2025411A1 (enExample) * | 1970-05-25 | 1971-12-09 | ||
| US3598877A (en) * | 1970-06-05 | 1971-08-10 | Shell Oil Co | Cyclodiolefin hydrogenation |
| AT314495B (de) * | 1971-12-02 | 1974-04-10 | Bayer Ag | Verfahren zur Gewinnung von technisch reinem Cyclopenten |
-
1974
- 1974-05-24 DE DE2425289A patent/DE2425289C3/de not_active Expired
-
1975
- 1975-05-08 US US05/575,661 patent/US4048242A/en not_active Expired - Lifetime
- 1975-05-22 IT IT49719/75A patent/IT1035824B/it active
- 1975-05-22 GB GB22191/75A patent/GB1505542A/en not_active Expired
- 1975-05-22 BE BE156588A patent/BE829353A/xx unknown
- 1975-05-22 NL NL7506041A patent/NL7506041A/xx not_active Application Discontinuation
- 1975-05-22 JP JP6028875A patent/JPS5550009B2/ja not_active Expired
- 1975-05-23 FR FR7516225A patent/FR2272057B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2425289B2 (de) | 1978-03-16 |
| IT1035824B (it) | 1979-10-20 |
| JPS50160238A (enExample) | 1975-12-25 |
| DE2425289A1 (de) | 1975-12-04 |
| US4048242A (en) | 1977-09-13 |
| BE829353A (fr) | 1975-11-24 |
| FR2272057B1 (enExample) | 1978-10-13 |
| GB1505542A (en) | 1978-03-30 |
| FR2272057A1 (enExample) | 1975-12-19 |
| JPS5550009B2 (enExample) | 1980-12-16 |
| NL7506041A (nl) | 1975-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| EHV | Ceased/renunciation |