DE2848697C2 - Verfahren zur Herstellung von Cyclopenten durch selektive Hydrierung von Cyclopentadien - Google Patents
Verfahren zur Herstellung von Cyclopenten durch selektive Hydrierung von CyclopentadienInfo
- Publication number
- DE2848697C2 DE2848697C2 DE2848697A DE2848697A DE2848697C2 DE 2848697 C2 DE2848697 C2 DE 2848697C2 DE 2848697 A DE2848697 A DE 2848697A DE 2848697 A DE2848697 A DE 2848697A DE 2848697 C2 DE2848697 C2 DE 2848697C2
- Authority
- DE
- Germany
- Prior art keywords
- cyclopentadiene
- nickel
- cyclopentene
- catalyst
- ammonia
- 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
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 title claims description 69
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 title claims description 39
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 16
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 56
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 22
- 229910052759 nickel Inorganic materials 0.000 claims description 19
- 229910021529 ammonia Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 7
- 239000000908 ammonium hydroxide Substances 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 239000007791 liquid phase Substances 0.000 claims 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000007868 Raney catalyst Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 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 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241001442654 Percnon planissimum Species 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- 229910000838 Al alloy Inorganic materials 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
- 229910000545 Nickel–aluminium alloy Inorganic materials 0.000 description 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 238000004230 steam cracking Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J25/00—Catalysts of the Raney type
- B01J25/02—Raney nickel
-
- 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
- C07C5/05—Partial hydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2525/00—Catalysts of the Raney type
- C07C2525/02—Raney nickel
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US05/850,578 US4131627A (en) | 1977-11-11 | 1977-11-11 | Continuous hydrogenation of cyclopentadiene to cyclopentene using a Raney nickel catalyst saturated with ammonia |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2848697A1 DE2848697A1 (de) | 1979-05-17 |
DE2848697C2 true DE2848697C2 (de) | 1987-02-05 |
Family
ID=25308538
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2848697A Expired DE2848697C2 (de) | 1977-11-11 | 1978-11-09 | Verfahren zur Herstellung von Cyclopenten durch selektive Hydrierung von Cyclopentadien |
Country Status (11)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4716256A (en) * | 1985-01-31 | 1987-12-29 | Phillips Petroleum Company | Hydrogenation of dienes |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2360555A (en) * | 1942-03-17 | 1944-10-17 | Shell Dev | Preparation of cyclic mono-olefins |
US3637877A (en) * | 1970-06-03 | 1972-01-25 | Phillips Petroleum Co | Modifiers for selective hydrogenation catalysts for cyclic polyenes |
US3862252A (en) * | 1972-12-28 | 1975-01-21 | Kanegafuchi Chemical Ind | Method of selective hydrogenation of cyclopentadiene |
US3937745A (en) * | 1974-08-29 | 1976-02-10 | The Goodyear Tire & Rubber Company | Selective hydrogenation of cyclopentadiene |
-
1977
- 1977-11-11 US US05/850,578 patent/US4131627A/en not_active Expired - Lifetime
-
1978
- 1978-08-22 CA CA309,796A patent/CA1099297A/en not_active Expired
- 1978-10-23 GB GB7841646A patent/GB2007709B/en not_active Expired
- 1978-10-26 MX MX175393A patent/MX149791A/es unknown
- 1978-11-07 FR FR7831419A patent/FR2408566A1/fr active Granted
- 1978-11-08 BR BR7807331A patent/BR7807331A/pt unknown
- 1978-11-08 JP JP53137769A patent/JPS6041645B2/ja not_active Expired
- 1978-11-09 DE DE2848697A patent/DE2848697C2/de not_active Expired
- 1978-11-10 NL NL7811159A patent/NL7811159A/xx not_active Application Discontinuation
- 1978-11-10 IT IT51866/78A patent/IT1109254B/it active
- 1978-11-10 BE BE191668A patent/BE871928A/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR2408566A1 (fr) | 1979-06-08 |
MX149791A (es) | 1983-12-21 |
JPS5476547A (en) | 1979-06-19 |
US4131627A (en) | 1978-12-26 |
GB2007709A (en) | 1979-05-23 |
CA1099297A (en) | 1981-04-14 |
IT7851866A0 (it) | 1978-11-10 |
GB2007709B (en) | 1982-03-24 |
NL7811159A (nl) | 1979-05-15 |
FR2408566B1 (US06168776-20010102-C00028.png) | 1983-08-12 |
BR7807331A (pt) | 1979-07-24 |
DE2848697A1 (de) | 1979-05-17 |
JPS6041645B2 (ja) | 1985-09-18 |
BE871928A (fr) | 1979-03-01 |
IT1109254B (it) | 1985-12-16 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8110 | Request for examination paragraph 44 | ||
D2 | Grant after examination | ||
8364 | No opposition during term of opposition | ||
8339 | Ceased/non-payment of the annual fee |